CA2592971A1 - Methode de traitement du cancer du cerveau - Google Patents

Methode de traitement du cancer du cerveau Download PDF

Info

Publication number: CA2592971A1
Authority: CA; Canada
Prior art keywords: methyl; quinazolin; alkyl; phenyl; amine
Prior art date: 2005-01-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002592971A

Other languages

English (en)

Inventor

Sui Xiong Cai

Mark B. Anderson

Adam Willardsen

Nilantha Sudath Sirisoma

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Myriad Genetics Inc

Cytovia Therapeutics LLC

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-01-03

Filing date

2006-01-03

Publication date

2006-07-13

2006-01-03 Application filed by Individual filed Critical Individual

2006-07-13 Publication of CA2592971A1 publication Critical patent/CA2592971A1/fr

Status Abandoned legal-status Critical Current

Links

208000003174 Brain Neoplasms Diseases 0.000 title claims abstract description 34
238000000034 method Methods 0.000 title description 83
150000001875 compounds Chemical class 0.000 claims abstract description 255
230000006907 apoptotic process Effects 0.000 claims abstract description 72
108010076667 Caspases Proteins 0.000 claims abstract description 55
102000011727 Caspases Human genes 0.000 claims abstract description 55
238000011282 treatment Methods 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims description 90
150000003839 salts Chemical class 0.000 claims description 57
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 37
125000000623 heterocyclic group Chemical group 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
201000010099 disease Diseases 0.000 claims description 28
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
210000004556 brain Anatomy 0.000 claims description 26
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 25
125000001475 halogen functional group Chemical group 0.000 claims description 23
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 22
125000003710 aryl alkyl group Chemical group 0.000 claims description 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
102000004243 Tubulin Human genes 0.000 claims description 19
108090000704 Tubulin Proteins 0.000 claims description 19
210000003169 central nervous system Anatomy 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 17
CIPVUQSDDVFBPO-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 CIPVUQSDDVFBPO-UHFFFAOYSA-N 0.000 claims description 15
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 15
230000002401 inhibitory effect Effects 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 15
241000124008 Mammalia Species 0.000 claims description 14
210000000133 brain stem Anatomy 0.000 claims description 13
101100054666 Streptomyces halstedii sch3 gene Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
230000003213 activating effect Effects 0.000 claims description 11
230000001939 inductive effect Effects 0.000 claims description 11
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 9
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
VYUWDIKZJLOZJL-UHFFFAOYSA-N n-(4-methoxyphenyl)-n,2-dimethylquinazolin-4-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 VYUWDIKZJLOZJL-UHFFFAOYSA-N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
101710183280 Topoisomerase Proteins 0.000 claims description 6
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
HXFFEQHSYUTPMD-UHFFFAOYSA-N 2,5-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC(Cl)=C12 HXFFEQHSYUTPMD-UHFFFAOYSA-N 0.000 claims description 5
CIINIBVJXMGLHX-UHFFFAOYSA-N 2,6-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=C(Cl)C=C12 CIINIBVJXMGLHX-UHFFFAOYSA-N 0.000 claims description 5
ZWSFLJALKMNMKZ-UHFFFAOYSA-N 2,7-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC(Cl)=CC=C12 ZWSFLJALKMNMKZ-UHFFFAOYSA-N 0.000 claims description 5
JGEQHBFWBZGDSK-UHFFFAOYSA-N 2-(fluoromethyl)-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(CF)=NC2=CC=CC=C12 JGEQHBFWBZGDSK-UHFFFAOYSA-N 0.000 claims description 5
REQTXYJALZRJCF-UHFFFAOYSA-N 2-chloro-n-(3,4-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 REQTXYJALZRJCF-UHFFFAOYSA-N 0.000 claims description 5
UMERRNXQLYCZAW-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,6-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=C(C)C=C12 UMERRNXQLYCZAW-UHFFFAOYSA-N 0.000 claims description 5
WYEXKHFIYNXOOH-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,7-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC(C)=CC=C12 WYEXKHFIYNXOOH-UHFFFAOYSA-N 0.000 claims description 5
RVVQCOFJEZMGFO-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-propoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OCCC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 RVVQCOFJEZMGFO-UHFFFAOYSA-N 0.000 claims description 5
IAMWEFPCABNDRT-UHFFFAOYSA-N 2-chloro-n-methyl-n-phenylquinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=CC=C1 IAMWEFPCABNDRT-UHFFFAOYSA-N 0.000 claims description 5
NZPYZRZUALMAPI-UHFFFAOYSA-N 2-methoxy-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(OC)=NC2=CC=CC=C12 NZPYZRZUALMAPI-UHFFFAOYSA-N 0.000 claims description 5
CNHHZBNXHMZZLR-UHFFFAOYSA-N 4-n-(2-chloroquinazolin-4-yl)-1-n,1-n,4-n-trimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 CNHHZBNXHMZZLR-UHFFFAOYSA-N 0.000 claims description 5
YQXLUXQBCCEIGS-UHFFFAOYSA-N 4-n-(6-methoxypyridin-3-yl)-2-n,4-n-dimethylquinazoline-2,4-diamine Chemical compound C=12C=CC=CC2=NC(NC)=NC=1N(C)C1=CC=C(OC)N=C1 YQXLUXQBCCEIGS-UHFFFAOYSA-N 0.000 claims description 5
UQHOAMFQDFYSBA-UHFFFAOYSA-N 4-n-[4-(dimethylamino)phenyl]-2-n,4-n-dimethylquinazoline-2,4-diamine Chemical compound C=12C=CC=CC2=NC(NC)=NC=1N(C)C1=CC=C(N(C)C)C=C1 UQHOAMFQDFYSBA-UHFFFAOYSA-N 0.000 claims description 5
ILGZWIYSDQMJAY-UHFFFAOYSA-N 5-methoxy-n-(4-methoxyphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC(OC)=C12 ILGZWIYSDQMJAY-UHFFFAOYSA-N 0.000 claims description 5
206010003571 Astrocytoma Diseases 0.000 claims description 5
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
OTIJJBAELVCKPE-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-chloro-n-methylquinazolin-4-amine Chemical compound C1=CC=C2C(N(C=3C=C4OCOC4=CC=3)C)=NC(Cl)=NC2=C1 OTIJJBAELVCKPE-UHFFFAOYSA-N 0.000 claims description 5
JTGWDXMHVGTWEP-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=NC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 JTGWDXMHVGTWEP-UHFFFAOYSA-N 0.000 claims description 5
PSBCEFQRMKLLLK-UHFFFAOYSA-N 1-n,1-n,4-n-trimethyl-4-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 PSBCEFQRMKLLLK-UHFFFAOYSA-N 0.000 claims description 4
HSIGTMCZNXWTHU-UHFFFAOYSA-N 1-n,4-n-dimethyl-4-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 HSIGTMCZNXWTHU-UHFFFAOYSA-N 0.000 claims description 4
MWIVTJPQNXNKGC-UHFFFAOYSA-N 2,8-dichloro-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=C(Cl)C=CC=C12 MWIVTJPQNXNKGC-UHFFFAOYSA-N 0.000 claims description 4
YSYHVEFDFWVFNK-UHFFFAOYSA-N 2-chloro-n-(2,4-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 YSYHVEFDFWVFNK-UHFFFAOYSA-N 0.000 claims description 4
TYNKRAPSWAKMSZ-UHFFFAOYSA-N 2-chloro-n-(3-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1 TYNKRAPSWAKMSZ-UHFFFAOYSA-N 0.000 claims description 4
XYRVBFJQGKLWQK-UHFFFAOYSA-N 2-chloro-n-(4-chlorophenyl)-n-methylquinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(Cl)C=C1 XYRVBFJQGKLWQK-UHFFFAOYSA-N 0.000 claims description 4
YZVGKWIJZRGKHN-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,8-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=C(C)C=CC=C12 YZVGKWIJZRGKHN-UHFFFAOYSA-N 0.000 claims description 4
FSLMXGLQAJMKIZ-UHFFFAOYSA-N 2-chloro-n-ethyl-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(CC)C1=CC=C(OC)C=C1 FSLMXGLQAJMKIZ-UHFFFAOYSA-N 0.000 claims description 4
CKZYZMNGKAKNSW-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-methylphenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(C)C=C1 CKZYZMNGKAKNSW-UHFFFAOYSA-N 0.000 claims description 4
CMANRZWLVWEYKY-UHFFFAOYSA-N 2-ethyl-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(CC)=NC=1N(C)C1=CC=C(OC)C=C1 CMANRZWLVWEYKY-UHFFFAOYSA-N 0.000 claims description 4
AUIIPISVOIPEAT-UHFFFAOYSA-N 4-[(2-chloroquinazolin-4-yl)-methylamino]phenol Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(O)C=C1 AUIIPISVOIPEAT-UHFFFAOYSA-N 0.000 claims description 4
206010061289 metastatic neoplasm Diseases 0.000 claims description 4
QROOVQPEUDNKIB-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound FC1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 QROOVQPEUDNKIB-UHFFFAOYSA-N 0.000 claims description 4
HRQZACPJDFWOCT-UHFFFAOYSA-N n-(4-methoxyphenyl)-n-methyl-2-methylsulfanylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(SC)=NC2=CC=CC=C12 HRQZACPJDFWOCT-UHFFFAOYSA-N 0.000 claims description 4
UUMCDUFWVPLFRA-UHFFFAOYSA-N n-(5-methoxypyridin-2-yl)-n,2-dimethylquinazolin-4-amine Chemical compound N1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 UUMCDUFWVPLFRA-UHFFFAOYSA-N 0.000 claims description 4
GRXFCMYNVMQAGT-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-n,2-dimethylquinazolin-4-amine Chemical compound N=1C(C)=NC2=CC=CC=C2C=1N(C)C1=CC=C(OC(F)F)C=C1 GRXFCMYNVMQAGT-UHFFFAOYSA-N 0.000 claims description 4
KPCLHMGNYZUFKC-UHFFFAOYSA-N 1-n,1-n,4-n-trimethyl-4-n-(2-methyl-6-nitroquinazolin-4-yl)benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1N(C)C1=NC(C)=NC2=CC=C([N+]([O-])=O)C=C12 KPCLHMGNYZUFKC-UHFFFAOYSA-N 0.000 claims description 3
HADKEDUVFJBONA-UHFFFAOYSA-N 2-(chloromethyl)-n-(4-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(CCl)=NC2=CC=CC=C12 HADKEDUVFJBONA-UHFFFAOYSA-N 0.000 claims description 3
BZVWKGZJSRCTMQ-UHFFFAOYSA-N 2-chloro-n-(2-methoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 BZVWKGZJSRCTMQ-UHFFFAOYSA-N 0.000 claims description 3
YMVUPHSSHKJBOE-UHFFFAOYSA-N 2-chloro-n-(4-ethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound C1=CC(OCC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 YMVUPHSSHKJBOE-UHFFFAOYSA-N 0.000 claims description 3
FSVVUPYMZOAIRT-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)-n,5-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC(C)=C12 FSVVUPYMZOAIRT-UHFFFAOYSA-N 0.000 claims description 3
WNVZXGOITGYARK-UHFFFAOYSA-N 2-chloro-n-(6-methoxypyridin-3-yl)-n-methylquinazolin-4-amine Chemical compound C1=NC(OC)=CC=C1N(C)C1=NC(Cl)=NC2=CC=CC=C12 WNVZXGOITGYARK-UHFFFAOYSA-N 0.000 claims description 3
WXELIIFXJNHKGQ-UHFFFAOYSA-N 2-chloro-n-methyl-n-(4-nitrophenyl)quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C([N+]([O-])=O)C=C1 WXELIIFXJNHKGQ-UHFFFAOYSA-N 0.000 claims description 3
SMTHPJLECOJZMZ-UHFFFAOYSA-N 2-chloro-n-methyl-n-[4-(trifluoromethoxy)phenyl]quinazolin-4-amine Chemical compound N=1C(Cl)=NC2=CC=CC=C2C=1N(C)C1=CC=C(OC(F)(F)F)C=C1 SMTHPJLECOJZMZ-UHFFFAOYSA-N 0.000 claims description 3
PDPLAOAALWZBAI-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)-2-n,2-n,4-n-trimethyl-6-nitroquinazoline-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(N(C)C)=NC2=CC=C([N+]([O-])=O)C=C12 PDPLAOAALWZBAI-UHFFFAOYSA-N 0.000 claims description 3
VYMQTHKHFCOTBM-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)-2-n,2-n,4-n-trimethylquinazoline-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(N(C)C)=NC2=CC=CC=C12 VYMQTHKHFCOTBM-UHFFFAOYSA-N 0.000 claims description 3
SDCOQCRGBSAZGF-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)-2-n,4-n-dimethylquinazoline-2,4-diamine Chemical compound C=12C=CC=CC2=NC(NC)=NC=1N(C)C1=CC=C(OC)C=C1 SDCOQCRGBSAZGF-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000001394 metastastic effect Effects 0.000 claims description 3
CBTCQJDVZHVCFX-UHFFFAOYSA-N n,2-dimethyl-n-(3,4,5-trimethoxyphenyl)quinazolin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(N(C)C=2C3=CC=CC=C3N=C(C)N=2)=C1 CBTCQJDVZHVCFX-UHFFFAOYSA-N 0.000 claims description 3
DUEOFWOYVUMCKC-UHFFFAOYSA-N n,2-dimethyl-n-(4-methylsulfanylphenyl)quinazolin-4-amine Chemical compound C1=CC(SC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 DUEOFWOYVUMCKC-UHFFFAOYSA-N 0.000 claims description 3
CYFKGPXUKCEWGW-UHFFFAOYSA-N n,2-dimethyl-n-(4-propan-2-yloxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 CYFKGPXUKCEWGW-UHFFFAOYSA-N 0.000 claims description 3
XIKQWUWGAHSPNN-UHFFFAOYSA-N n-(4-ethoxyphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=CC(OCC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 XIKQWUWGAHSPNN-UHFFFAOYSA-N 0.000 claims description 3
JBGYKZGLDRHLJU-UHFFFAOYSA-N n-[4-(4-methoxy-n-methylanilino)quinazolin-2-yl]hydroxylamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(NO)=NC2=CC=CC=C12 JBGYKZGLDRHLJU-UHFFFAOYSA-N 0.000 claims description 3
FCWVBILVQLPHJJ-UHFFFAOYSA-N 2-chloro-n-(2,3-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=CC(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1OC FCWVBILVQLPHJJ-UHFFFAOYSA-N 0.000 claims description 2
QGDAWZDGEQZCJD-UHFFFAOYSA-N 2-chloro-n-(2,5-dimethoxyphenyl)-n-methylquinazolin-4-amine Chemical compound COC1=CC=C(OC)C(N(C)C=2C3=CC=CC=C3N=C(Cl)N=2)=C1 QGDAWZDGEQZCJD-UHFFFAOYSA-N 0.000 claims description 2
208000025997 central nervous system neoplasm Diseases 0.000 claims description 2
208000005017 glioblastoma Diseases 0.000 claims description 2
206010027191 meningioma Diseases 0.000 claims description 2
201000008806 mesenchymal cell neoplasm Diseases 0.000 claims description 2
NXOZBYBATCYWGY-UHFFFAOYSA-N n-(3-fluoro-4-methoxyphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=C(F)C(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 NXOZBYBATCYWGY-UHFFFAOYSA-N 0.000 claims description 2
ZXKCLECYMVGCNR-UHFFFAOYSA-N n-(4-ethylphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=CC(CC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 ZXKCLECYMVGCNR-UHFFFAOYSA-N 0.000 claims description 2
BYYFLAPFOYIQKP-UHFFFAOYSA-N n-(4-methoxyphenyl)-n-methyl-2-morpholin-4-ylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(N2CCOCC2)=NC2=CC=CC=C12 BYYFLAPFOYIQKP-UHFFFAOYSA-N 0.000 claims description 2
AKFHIQXDZMGKMN-UHFFFAOYSA-N n-(4-methoxyphenyl)-n-methylquinolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=CC=NC2=CC=CC=C12 AKFHIQXDZMGKMN-UHFFFAOYSA-N 0.000 claims 2
YWAGOXUERHPQNE-UHFFFAOYSA-N 2-n,2-n,5-n-trimethyl-5-n-(2-methylquinazolin-4-yl)pyridine-2,5-diamine Chemical compound C1=NC(N(C)C)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 YWAGOXUERHPQNE-UHFFFAOYSA-N 0.000 claims 1
ZQCMMRRRVQRYGL-UHFFFAOYSA-N 2-n-benzyl-4-n-(4-methoxyphenyl)-4-n-methylquinazoline-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(NCC=2C=CC=CC=2)=NC2=CC=CC=C12 ZQCMMRRRVQRYGL-UHFFFAOYSA-N 0.000 claims 1
FXLDTDJVNSDFJE-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)-4-n,6-n,6-n,2-tetramethylquinazoline-4,6-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=C(N(C)C)C=C12 FXLDTDJVNSDFJE-UHFFFAOYSA-N 0.000 claims 1
206010002224 anaplastic astrocytoma Diseases 0.000 claims 1
GZTWCSBJBMYCJV-UHFFFAOYSA-N n-[4-[4-(dimethylamino)-n-methylanilino]quinazolin-2-yl]-n-methylacetamide Chemical compound C1=CC(N(C)C)=CC=C1N(C)C1=NC(N(C)C(C)=O)=NC2=CC=CC=C12 GZTWCSBJBMYCJV-UHFFFAOYSA-N 0.000 claims 1
239000000411 inducer Substances 0.000 abstract description 32
239000012190 activator Substances 0.000 abstract description 30
230000002159 abnormal effect Effects 0.000 abstract description 5
230000004222 uncontrolled growth Effects 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
206010028980 Neoplasm Diseases 0.000 description 72
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 68
101150041968 CDC13 gene Proteins 0.000 description 66
-1 aspartyl residue Chemical group 0.000 description 62
210000004027 cell Anatomy 0.000 description 62
239000000203 mixture Substances 0.000 description 58
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 39
238000005481 NMR spectroscopy Methods 0.000 description 38
201000011510 cancer Diseases 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 34
238000005160 1H NMR spectroscopy Methods 0.000 description 32
239000007787 solid Substances 0.000 description 32
235000019439 ethyl acetate Nutrition 0.000 description 30
239000002246 antineoplastic agent Substances 0.000 description 28
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
229940093499 ethyl acetate Drugs 0.000 description 26
125000005843 halogen group Chemical group 0.000 description 26
239000003112 inhibitor Substances 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
229940002612 prodrug Drugs 0.000 description 22
239000000651 prodrug Substances 0.000 description 22
125000003118 aryl group Chemical group 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
241001465754 Metazoa Species 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
239000000460 chlorine Chemical group 0.000 description 18
230000006870 function Effects 0.000 description 18
MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 16
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 15
TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
229940041181 antineoplastic drug Drugs 0.000 description 13
229940079593 drug Drugs 0.000 description 13
230000009826 neoplastic cell growth Effects 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
239000008280 blood Substances 0.000 description 11
238000002648 combination therapy Methods 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000000725 suspension Substances 0.000 description 11
239000003480 eluent Substances 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
230000003389 potentiating effect Effects 0.000 description 10
102000003952 Caspase 3 Human genes 0.000 description 9
108090000397 Caspase 3 Proteins 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
210000001744 T-lymphocyte Anatomy 0.000 description 9
230000004913 activation Effects 0.000 description 9
230000030833 cell death Effects 0.000 description 9
208000037765 diseases and disorders Diseases 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
238000002560 therapeutic procedure Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
125000005915 C6-C14 aryl group Chemical group 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
102000007537 Type II DNA Topoisomerases Human genes 0.000 description 8
108010046308 Type II DNA Topoisomerases Proteins 0.000 description 8
239000012043 crude product Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000000338 in vitro Methods 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
229930012538 Paclitaxel Natural products 0.000 description 7
201000004681 Psoriasis Diseases 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000002512 chemotherapy Methods 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
230000001419 dependent effect Effects 0.000 description 7
238000001914 filtration Methods 0.000 description 7
125000001072 heteroaryl group Chemical group 0.000 description 7
125000005241 heteroarylamino group Chemical class 0.000 description 7
229960001592 paclitaxel Drugs 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
210000002437 synoviocyte Anatomy 0.000 description 7
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 7
238000012360 testing method Methods 0.000 description 7
JFXDIXYFXDOZIT-UHFFFAOYSA-N 4-methoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C=C1 JFXDIXYFXDOZIT-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
208000023275 Autoimmune disease Diseases 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
108020004414 DNA Proteins 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
230000012010 growth Effects 0.000 description 6
230000007246 mechanism Effects 0.000 description 6
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
208000016691 refractory malignant neoplasm Diseases 0.000 description 6
206010039073 rheumatoid arthritis Diseases 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
102000015212 Fas Ligand Protein Human genes 0.000 description 5
108010039471 Fas Ligand Protein Proteins 0.000 description 5
239000007832 Na2SO4 Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
VEOXVBTXROWDAH-UHFFFAOYSA-N acetic acid;3-[1-(3-aminopropyl)indol-3-yl]-4-(1-methylindol-3-yl)pyrrole-2,5-dione Chemical compound CC(O)=O.C12=CC=CC=C2N(C)C=C1C1=C(C=2C3=CC=CC=C3N(CCCN)C=2)C(=O)NC1=O VEOXVBTXROWDAH-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 5
YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
230000003902 lesion Effects 0.000 description 5
239000012038 nucleophile Substances 0.000 description 5
239000012188 paraffin wax Substances 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
229960004641 rituximab Drugs 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
238000001356 surgical procedure Methods 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 4
UMERIGXDBJFEAT-UHFFFAOYSA-N 4-chloro-2-(fluoromethyl)quinazoline Chemical compound C1=CC=CC2=NC(CF)=NC(Cl)=C21 UMERIGXDBJFEAT-UHFFFAOYSA-N 0.000 description 4
235000019489 Almond oil Nutrition 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
206010006187 Breast cancer Diseases 0.000 description 4
208000026310 Breast neoplasm Diseases 0.000 description 4
102100022595 Broad substrate specificity ATP-binding cassette transporter ABCG2 Human genes 0.000 description 4
201000009030 Carcinoma Diseases 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
206010014967 Ependymoma Diseases 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
241000282412 Homo Species 0.000 description 4
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 4
239000005411 L01XE02 - Gefitinib Substances 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
102000035195 Peptidases Human genes 0.000 description 4
108091005804 Peptidases Proteins 0.000 description 4
239000004365 Protease Substances 0.000 description 4
229940079156 Proteasome inhibitor Drugs 0.000 description 4
102100028662 Sigma intracellular receptor 2 Human genes 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000004442 acylamino group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
239000008168 almond oil Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000001093 anti-cancer Effects 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
210000003719 b-lymphocyte Anatomy 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
230000037396 body weight Effects 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
229940127089 cytotoxic agent Drugs 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
239000008298 dragée Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
230000008030 elimination Effects 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
230000006882 induction of apoptosis Effects 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 4
229960000485 methotrexate Drugs 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
239000001267 polyvinylpyrrolidone Substances 0.000 description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
230000008569 process Effects 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
239000003207 proteasome inhibitor Substances 0.000 description 4
ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
230000000699 topical effect Effects 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
210000004881 tumor cell Anatomy 0.000 description 4
229960003048 vinblastine Drugs 0.000 description 4
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 4
RTAQXMPLDYGGHQ-UHFFFAOYSA-N 2-(fluoromethyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2C(=O)NC(CF)=NC2=C1 RTAQXMPLDYGGHQ-UHFFFAOYSA-N 0.000 description 3
RWZYAGGXGHYGMB-WGGUOBTBSA-N 2-aminobenzoic acid Chemical class NC1=CC=CC=C1[14C](O)=O RWZYAGGXGHYGMB-WGGUOBTBSA-N 0.000 description 3
AKKYWYCANLVLAS-UHFFFAOYSA-N 2-chloro-n-phenylquinazolin-4-amine Chemical class C=12C=CC=CC2=NC(Cl)=NC=1NC1=CC=CC=C1 AKKYWYCANLVLAS-UHFFFAOYSA-N 0.000 description 3
OXVPNGBFUAIXTE-UHFFFAOYSA-N 6-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=CC(C)=CC=C21 OXVPNGBFUAIXTE-UHFFFAOYSA-N 0.000 description 3
108010078791 Carrier Proteins Proteins 0.000 description 3
102000004127 Cytokines Human genes 0.000 description 3
108090000695 Cytokines Proteins 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
101000823298 Homo sapiens Broad substrate specificity ATP-binding cassette transporter ABCG2 Proteins 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
201000010133 Oligodendroglioma Diseases 0.000 description 3
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
101710109012 Sigma intracellular receptor 2 Proteins 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
230000009471 action Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
230000002424 anti-apoptotic effect Effects 0.000 description 3
230000000340 anti-metabolite Effects 0.000 description 3
230000000259 anti-tumor effect Effects 0.000 description 3
229940100197 antimetabolite Drugs 0.000 description 3
239000002256 antimetabolite Substances 0.000 description 3
230000001640 apoptogenic effect Effects 0.000 description 3
125000004104 aryloxy group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
229960004316 cisplatin Drugs 0.000 description 3
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000000576 coating method Methods 0.000 description 3
208000029742 colonic neoplasm Diseases 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940111134 coxibs Drugs 0.000 description 3
239000006071 cream Substances 0.000 description 3
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 3
230000007547 defect Effects 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000012636 effector Substances 0.000 description 3
229960005420 etoposide Drugs 0.000 description 3
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
229960002584 gefitinib Drugs 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229940022353 herceptin Drugs 0.000 description 3
239000004030 hiv protease inhibitor Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
206010020718 hyperplasia Diseases 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000003211 malignant effect Effects 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
230000001613 neoplastic effect Effects 0.000 description 3
208000027831 neuroepithelial neoplasm Diseases 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000004533 oil dispersion Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000002674 ointment Substances 0.000 description 3
229940127084 other anti-cancer agent Drugs 0.000 description 3
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 3
230000035755 proliferation Effects 0.000 description 3
230000001737 promoting effect Effects 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000001959 radiotherapy Methods 0.000 description 3
239000000018 receptor agonist Substances 0.000 description 3
229940044601 receptor agonist Drugs 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000001105 regulatory effect Effects 0.000 description 3
239000000523 sample Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
206010062261 spinal cord neoplasm Diseases 0.000 description 3
125000000547 substituted alkyl group Chemical group 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
210000001685 thyroid gland Anatomy 0.000 description 3
239000003558 transferase inhibitor Substances 0.000 description 3
229960000575 trastuzumab Drugs 0.000 description 3
229960001727 tretinoin Drugs 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
239000003744 tubulin modulator Substances 0.000 description 3
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
229960004528 vincristine Drugs 0.000 description 3
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 3
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 3
YVMTWTZIAIUURI-BCTWRDQXSA-N (1s,5s,8e)-8-benzylidene-5-(3-hydroxyphenyl)-2-methyl-2-azabicyclo[3.3.1]nonan-7-one Chemical compound C1(/[C@@H]2C[C@](CC1=O)(CCN2C)C=1C=C(O)C=CC=1)=C/C1=CC=CC=C1 YVMTWTZIAIUURI-BCTWRDQXSA-N 0.000 description 2
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 2
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
VZDVVLXYAOVNRW-UHFFFAOYSA-N 2,4-dichloro-6-methylquinazoline Chemical compound N1=C(Cl)N=C(Cl)C2=CC(C)=CC=C21 VZDVVLXYAOVNRW-UHFFFAOYSA-N 0.000 description 2
KSLWZHWJFFDMMK-UHFFFAOYSA-N 2-(chloromethyl)-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(CCl)=NC(=O)C2=C1 KSLWZHWJFFDMMK-UHFFFAOYSA-N 0.000 description 2
NBUUUJWWOARGNW-UHFFFAOYSA-N 2-amino-5-methylbenzoic acid Chemical compound CC1=CC=C(N)C(C(O)=O)=C1 NBUUUJWWOARGNW-UHFFFAOYSA-N 0.000 description 2
WMPTYRGXBUYONY-UHFFFAOYSA-N 2-chloroquinazoline Chemical class C1=CC=CC2=NC(Cl)=NC=C21 WMPTYRGXBUYONY-UHFFFAOYSA-N 0.000 description 2
GNFVFPBRMLIKIM-UHFFFAOYSA-N 2-fluoroacetonitrile Chemical compound FCC#N GNFVFPBRMLIKIM-UHFFFAOYSA-N 0.000 description 2
FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical class NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 description 2
AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 2
AKJHMTWEGVYYSE-AIRMAKDCSA-N 4-HPR Chemical compound C=1C=C(O)C=CC=1NC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-AIRMAKDCSA-N 0.000 description 2
SVLWKWGOOHGUNE-UHFFFAOYSA-N 4-chloro-2-methyl-6-nitroquinazoline Chemical compound C1=C([N+]([O-])=O)C=CC2=NC(C)=NC(Cl)=C21 SVLWKWGOOHGUNE-UHFFFAOYSA-N 0.000 description 2
HAAZMOAXEMIBAJ-UHFFFAOYSA-N 4-chloro-2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC(Cl)=C21 HAAZMOAXEMIBAJ-UHFFFAOYSA-N 0.000 description 2
GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
208000000659 Autoimmune lymphoproliferative syndrome Diseases 0.000 description 2
206010005003 Bladder cancer Diseases 0.000 description 2
108010006654 Bleomycin Proteins 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
102100035904 Caspase-1 Human genes 0.000 description 2
108090000426 Caspase-1 Proteins 0.000 description 2
206010007953 Central nervous system lymphoma Diseases 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010009944 Colon cancer Diseases 0.000 description 2
102000003903 Cyclin-dependent kinases Human genes 0.000 description 2
108090000266 Cyclin-dependent kinases Proteins 0.000 description 2
102000005927 Cysteine Proteases Human genes 0.000 description 2
108010005843 Cysteine Proteases Proteins 0.000 description 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
206010059866 Drug resistance Diseases 0.000 description 2
HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
208000030836 Hashimoto thyroiditis Diseases 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
208000007766 Kaposi sarcoma Diseases 0.000 description 2
MLFKVJCWGUZWNV-UHFFFAOYSA-N L-alanosine Natural products OC(=O)C(N)CN(O)N=O MLFKVJCWGUZWNV-UHFFFAOYSA-N 0.000 description 2
239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
DAQAKHDKYAWHCG-UHFFFAOYSA-N Lactacystin Natural products CC(=O)NC(C(O)=O)CSC(=O)C1(C(O)C(C)C)NC(=O)C(C)C1O DAQAKHDKYAWHCG-UHFFFAOYSA-N 0.000 description 2
206010062049 Lymphocytic infiltration Diseases 0.000 description 2
208000000172 Medulloblastoma Diseases 0.000 description 2
108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 2
206010027476 Metastases Diseases 0.000 description 2
206010059282 Metastases to central nervous system Diseases 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
102100021339 Multidrug resistance-associated protein 1 Human genes 0.000 description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 description 2
206010029260 Neuroblastoma Diseases 0.000 description 2
108010016076 Octreotide Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000007641 Pinealoma Diseases 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
206010060862 Prostate cancer Diseases 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
230000018199 S phase Effects 0.000 description 2
208000000453 Skin Neoplasms Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 2
102000004357 Transferases Human genes 0.000 description 2
108090000992 Transferases Proteins 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229950005033 alanosine Drugs 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229950010817 alvocidib Drugs 0.000 description 2
BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 2
230000033115 angiogenesis Effects 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
230000001028 anti-proliverative effect Effects 0.000 description 2
239000003080 antimitotic agent Substances 0.000 description 2
229940034982 antineoplastic agent Drugs 0.000 description 2
238000003782 apoptosis assay Methods 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
125000002102 aryl alkyloxo group Chemical group 0.000 description 2
125000005015 aryl alkynyl group Chemical group 0.000 description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
125000003828 azulenyl group Chemical group 0.000 description 2
108700000707 bcl-2-Associated X Proteins 0.000 description 2
102000055102 bcl-2-Associated X Human genes 0.000 description 2
235000013871 bee wax Nutrition 0.000 description 2
239000012166 beeswax Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000008901 benefit Effects 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
229920002988 biodegradable polymer Polymers 0.000 description 2
239000004621 biodegradable polymer Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
229960001561 bleomycin Drugs 0.000 description 2
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
244000309464 bull Species 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
101150055276 ced-3 gene Proteins 0.000 description 2
230000022131 cell cycle Effects 0.000 description 2
230000032823 cell division Effects 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 2
229960004630 chlorambucil Drugs 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000013068 control sample Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 2
229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000034994 death Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 2
229960001389 doxazosin Drugs 0.000 description 2
229940121647 egfr inhibitor Drugs 0.000 description 2
YZQRAQOSAPWELU-UHFFFAOYSA-O elliptinium Chemical compound C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 YZQRAQOSAPWELU-UHFFFAOYSA-O 0.000 description 2
229950007539 elliptinium Drugs 0.000 description 2
239000003623 enhancer Substances 0.000 description 2
229960001904 epirubicin Drugs 0.000 description 2
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 2
239000003925 fat Substances 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
229950003662 fenretinide Drugs 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
230000036541 health Effects 0.000 description 2
125000005553 heteroaryloxy group Chemical group 0.000 description 2
230000013632 homeostatic process Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000008172 hydrogenated vegetable oil Substances 0.000 description 2
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
229960001101 ifosfamide Drugs 0.000 description 2
229960003685 imatinib mesylate Drugs 0.000 description 2
238000002513 implantation Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
229960001936 indinavir Drugs 0.000 description 2
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229940084651 iressa Drugs 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000002147 killing effect Effects 0.000 description 2
DAQAKHDKYAWHCG-RWTHQLGUSA-N lactacystin Chemical compound CC(=O)N[C@H](C(O)=O)CSC(=O)[C@]1([C@@H](O)C(C)C)NC(=O)[C@H](C)[C@@H]1O DAQAKHDKYAWHCG-RWTHQLGUSA-N 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 2
DHMTURDWPRKSOA-RUZDIDTESA-N lonafarnib Chemical compound C1CN(C(=O)N)CCC1CC(=O)N1CCC([C@@H]2C3=C(Br)C=C(Cl)C=C3CCC3=CC(Br)=CN=C32)CC1 DHMTURDWPRKSOA-RUZDIDTESA-N 0.000 description 2
229960004844 lovastatin Drugs 0.000 description 2
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 2
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
210000004698 lymphocyte Anatomy 0.000 description 2
230000005427 lymphocyte apoptotic process Effects 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 2
229960001924 melphalan Drugs 0.000 description 2
229960001428 mercaptopurine Drugs 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
229960003539 mitoguazone Drugs 0.000 description 2
MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 2
KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 2
229960001156 mitoxantrone Drugs 0.000 description 2
230000036457 multidrug resistance Effects 0.000 description 2
108010066052 multidrug resistance-associated protein 1 Proteins 0.000 description 2
KEAUPBBALQZPOL-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-chloroquinazolin-4-amine Chemical compound C1=CC=CC2=NC(Cl)=NC(NC=3C=C4OCOC4=CC=3)=C21 KEAUPBBALQZPOL-UHFFFAOYSA-N 0.000 description 2
GNEWLLIRDAPRSZ-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-2-methylquinazolin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 GNEWLLIRDAPRSZ-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229960002700 octreotide Drugs 0.000 description 2
244000052769 pathogen Species 0.000 description 2
230000001717 pathogenic effect Effects 0.000 description 2
230000037361 pathway Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
208000016800 primary central nervous system lymphoma Diseases 0.000 description 2
238000012545 processing Methods 0.000 description 2
230000005522 programmed cell death Effects 0.000 description 2
230000000770 proinflammatory effect Effects 0.000 description 2
239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
230000004044 response Effects 0.000 description 2
208000037803 restenosis Diseases 0.000 description 2
229930002330 retinoic acid Natural products 0.000 description 2
150000004492 retinoid derivatives Chemical class 0.000 description 2
229960001852 saquinavir Drugs 0.000 description 2
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 2
201000000849 skin cancer Diseases 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
208000000587 small cell lung carcinoma Diseases 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
229960001603 tamoxifen Drugs 0.000 description 2
229960002613 tamsulosin Drugs 0.000 description 2
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 2
229960001693 terazosin Drugs 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
239000012049 topical pharmaceutical composition Substances 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
JKFZMIQMKFWJAY-RQJQXFIZSA-N (1r,3s,5z)-5-[(2e)-2-[(3as,7as)-1-[(2r)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-3a,5,6,7-tetrahydro-3h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC=C([C@]2(CCC1)C)[C@@H](CC#CC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C JKFZMIQMKFWJAY-RQJQXFIZSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
CUFQBQOBLVLKRF-RZDMPUFOSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 description 1
HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
125000006002 1,1-difluoroethyl group Chemical group 0.000 description 1
XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
HGHPXBLOAQXDCO-UHFFFAOYSA-N 2,4-dichloro-6-nitroquinazoline Chemical compound N1=C(Cl)N=C(Cl)C2=CC([N+](=O)[O-])=CC=C21 HGHPXBLOAQXDCO-UHFFFAOYSA-N 0.000 description 1
KQSQNPFNPDWXSU-UHFFFAOYSA-N 2-(chloromethyl)-1-methyl-n-phenyl-2h-quinazolin-4-amine Chemical compound C12=CC=CC=C2N(C)C(CCl)N=C1NC1=CC=CC=C1 KQSQNPFNPDWXSU-UHFFFAOYSA-N 0.000 description 1
LSKPNPOAEVGRFF-UHFFFAOYSA-N 2-(fluoromethyl)-n-phenylquinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(CF)=NC=1NC1=CC=CC=C1 LSKPNPOAEVGRFF-UHFFFAOYSA-N 0.000 description 1
VRMSFHRAWDJXAS-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-n-phenylquinazolin-4-amine Chemical class C=12C=CC=CC2=NC(CN(C)C)=NC=1NC1=CC=CC=C1 VRMSFHRAWDJXAS-UHFFFAOYSA-N 0.000 description 1
IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 1
DYZDIWNRWSNVPT-UHFFFAOYSA-N 2-amino-6-methoxybenzoic acid Chemical compound COC1=CC=CC(N)=C1C(O)=O DYZDIWNRWSNVPT-UHFFFAOYSA-N 0.000 description 1
REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
JNXQCSFSCDFMOY-UHFFFAOYSA-N 2-chloro-n-(2,3-dimethoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC=CC(NC=2C3=CC=CC=C3N=C(Cl)N=2)=C1OC JNXQCSFSCDFMOY-UHFFFAOYSA-N 0.000 description 1
DQZUXAMIONYCIA-UHFFFAOYSA-N 2-chloro-n-(2,4-dimethoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 DQZUXAMIONYCIA-UHFFFAOYSA-N 0.000 description 1
VYQOQVFRTFZOKI-UHFFFAOYSA-N 2-chloro-n-(3,4-dimethoxyphenyl)quinazolin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 VYQOQVFRTFZOKI-UHFFFAOYSA-N 0.000 description 1
MNBFVXCBROXYLN-UHFFFAOYSA-N 2-chloro-n-(3-methoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC=CC(NC=2C3=CC=CC=C3N=C(Cl)N=2)=C1 MNBFVXCBROXYLN-UHFFFAOYSA-N 0.000 description 1
BYJWDGXGDZTRFX-UHFFFAOYSA-N 2-chloro-n-(4-ethoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 BYJWDGXGDZTRFX-UHFFFAOYSA-N 0.000 description 1
RIZSNWUCMWZSKH-UHFFFAOYSA-N 2-chloro-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 RIZSNWUCMWZSKH-UHFFFAOYSA-N 0.000 description 1
LQECWVZHZNSUAL-UHFFFAOYSA-N 2-chloro-n-(4-propoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OCCC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 LQECWVZHZNSUAL-UHFFFAOYSA-N 0.000 description 1
NFPIHMWCQJLBBI-UHFFFAOYSA-N 2-chloro-n-(6-methoxypyridin-3-yl)quinazolin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC(Cl)=NC2=CC=CC=C12 NFPIHMWCQJLBBI-UHFFFAOYSA-N 0.000 description 1
HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical class C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 1
DRISBNJRWVXOEG-UHFFFAOYSA-N 2-methyl-6-nitro-3,1-benzoxazin-4-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)OC(C)=NC2=C1 DRISBNJRWVXOEG-UHFFFAOYSA-N 0.000 description 1
GGIUORIPCAXHLV-UHFFFAOYSA-N 2-methyl-6-nitro-n-phenylquinazolin-4-amine Chemical class C=12C=C([N+]([O-])=O)C=CC2=NC(C)=NC=1NC1=CC=CC=C1 GGIUORIPCAXHLV-UHFFFAOYSA-N 0.000 description 1
HYXKCDQTUTVHAV-UHFFFAOYSA-N 2-methyl-n-(3,4,5-trimethoxyphenyl)quinazolin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2C3=CC=CC=C3N=C(C)N=2)=C1 HYXKCDQTUTVHAV-UHFFFAOYSA-N 0.000 description 1
KQGDNLGZZAVQLA-UHFFFAOYSA-N 2-methyl-n-(4-methylsulfanylphenyl)quinazolin-4-amine Chemical compound C1=CC(SC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 KQGDNLGZZAVQLA-UHFFFAOYSA-N 0.000 description 1
LRVWJQNNVSNJSX-UHFFFAOYSA-N 2-methyl-n-(4-propan-2-yloxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 LRVWJQNNVSNJSX-UHFFFAOYSA-N 0.000 description 1
UDBUIBPSSKNURG-UHFFFAOYSA-N 2-n,2-n-dimethyl-5-n-(2-methylquinazolin-4-yl)pyridine-2,5-diamine Chemical compound C1=NC(N(C)C)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 UDBUIBPSSKNURG-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NHFDRBXTEDBWCZ-ZROIWOOFSA-N 3-[2,4-dimethyl-5-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=CC=C3NC\2=O)=C1C NHFDRBXTEDBWCZ-ZROIWOOFSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
OZBUFFXESDBEHG-FXILSDISSA-N 4-[[(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OZBUFFXESDBEHG-FXILSDISSA-N 0.000 description 1
PMBABTLGYWFWBZ-UHFFFAOYSA-N 4-chloro-2-(chloromethyl)quinazoline Chemical compound C1=CC=CC2=NC(CCl)=NC(Cl)=C21 PMBABTLGYWFWBZ-UHFFFAOYSA-N 0.000 description 1
XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 1
AKJHMTWEGVYYSE-FXILSDISSA-N 4-hydroxyphenyl retinamide Chemical compound C=1C=C(O)C=CC=1NC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-FXILSDISSA-N 0.000 description 1
DYUKCQKKCVNACX-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)-4-n,2-dimethylquinazoline-4,6-diamine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=C(N)C=C12 DYUKCQKKCVNACX-UHFFFAOYSA-N 0.000 description 1
VJPRMSSYQNPZGF-UHFFFAOYSA-N 4-n-methyl-4-n-(2-methylquinazolin-4-yl)benzene-1,4-diamine Chemical compound N=1C(C)=NC2=CC=CC=C2C=1N(C)C1=CC=C(N)C=C1 VJPRMSSYQNPZGF-UHFFFAOYSA-N 0.000 description 1
UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 1
NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
ASCKCOHWDCSDCN-UHFFFAOYSA-N 5-chloro-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=CC=C2Cl ASCKCOHWDCSDCN-UHFFFAOYSA-N 0.000 description 1
SSYHZDZVRVADQW-UHFFFAOYSA-N 5-methoxy-2-methyl-1h-quinazolin-4-one Chemical compound CC1=NC(O)=C2C(OC)=CC=CC2=N1 SSYHZDZVRVADQW-UHFFFAOYSA-N 0.000 description 1
OVLVVBLYTQYCCS-UHFFFAOYSA-N 5-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=CC=C2C OVLVVBLYTQYCCS-UHFFFAOYSA-N 0.000 description 1
RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 1
IGWJEWGQUFOVDP-UHFFFAOYSA-N 6-chloro-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=CC(Cl)=CC=C21 IGWJEWGQUFOVDP-UHFFFAOYSA-N 0.000 description 1
QEXAYZARVWHJJA-UHFFFAOYSA-N 7-chloro-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C=2C1=CC(Cl)=CC=2 QEXAYZARVWHJJA-UHFFFAOYSA-N 0.000 description 1
PBCZSGKMGDDXIJ-HQCWYSJUSA-N 7-hydroxystaurosporine Chemical compound N([C@H](O)C1=C2C3=CC=CC=C3N3C2=C24)C(=O)C1=C2C1=CC=CC=C1N4[C@H]1C[C@@H](NC)[C@@H](OC)[C@]3(C)O1 PBCZSGKMGDDXIJ-HQCWYSJUSA-N 0.000 description 1
OLOBNXMPLWWBAX-UHFFFAOYSA-N 7-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C=2C1=CC(C)=CC=2 OLOBNXMPLWWBAX-UHFFFAOYSA-N 0.000 description 1
PBCZSGKMGDDXIJ-UHFFFAOYSA-N 7beta-hydroxystaurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3C(O)NC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 PBCZSGKMGDDXIJ-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
AKXWCWNEEZHWFL-UHFFFAOYSA-N 8-chloro-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C(Cl)=CC=C2 AKXWCWNEEZHWFL-UHFFFAOYSA-N 0.000 description 1
WFDHXKXFTSQIMG-UHFFFAOYSA-N 8-methyl-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C(C)=CC=C2 WFDHXKXFTSQIMG-UHFFFAOYSA-N 0.000 description 1
229940027041 8-mop Drugs 0.000 description 1
SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
206010065869 Astrocytoma, low grade Diseases 0.000 description 1
108010019625 Atazanavir Sulfate Proteins 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
102100037904 CD9 antigen Human genes 0.000 description 1
229940126074 CDK kinase inhibitor Drugs 0.000 description 1
108010082830 CEP 2563 Proteins 0.000 description 1
QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
241000244203 Caenorhabditis elegans Species 0.000 description 1
101100351961 Caenorhabditis elegans pgp-1 gene Proteins 0.000 description 1
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
208000017897 Carcinoma of esophagus Diseases 0.000 description 1
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
229940123169 Caspase inhibitor Drugs 0.000 description 1
201000002844 Cerebellar liponeurocytoma Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
201000005690 Chordoid glioma Diseases 0.000 description 1
208000006332 Choriocarcinoma Diseases 0.000 description 1
208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
206010010144 Completed suicide Diseases 0.000 description 1
101000932768 Conus catus Alpha-conotoxin CIC Proteins 0.000 description 1
101150073133 Cpt1a gene Proteins 0.000 description 1
208000009798 Craniopharyngioma Diseases 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
102100034770 Cyclin-dependent kinase inhibitor 3 Human genes 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
230000006820 DNA synthesis Effects 0.000 description 1
229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
108010092160 Dactinomycin Proteins 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
208000021994 Diffuse astrocytoma Diseases 0.000 description 1
206010061818 Disease progression Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
206010014733 Endometrial cancer Diseases 0.000 description 1
206010014759 Endometrial neoplasm Diseases 0.000 description 1
102000010911 Enzyme Precursors Human genes 0.000 description 1
108010062466 Enzyme Precursors Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
208000032027 Essential Thrombocythemia Diseases 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
206010015719 Exsanguination Diseases 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
208000032612 Glial tumor Diseases 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
201000005409 Gliomatosis cerebri Diseases 0.000 description 1
206010068601 Glioneuronal tumour Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
229940122440 HIV protease inhibitor Drugs 0.000 description 1
208000006050 Hemangiopericytoma Diseases 0.000 description 1
208000005176 Hepatitis C Diseases 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
101000945639 Homo sapiens Cyclin-dependent kinase inhibitor 3 Proteins 0.000 description 1
101000969812 Homo sapiens Multidrug resistance-associated protein 1 Proteins 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
208000019758 Hypergammaglobulinemia Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102000005755 Intercellular Signaling Peptides and Proteins Human genes 0.000 description 1
108010070716 Intercellular Signaling Peptides and Proteins Proteins 0.000 description 1
108010002350 Interleukin-2 Proteins 0.000 description 1
108090000978 Interleukin-4 Proteins 0.000 description 1
SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 description 1
239000005517 L01XE01 - Imatinib Substances 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
208000008771 Lymphadenopathy Diseases 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
108010090306 Member 2 Subfamily G ATP Binding Cassette Transporter Proteins 0.000 description 1
208000015021 Meningeal Neoplasms Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
208000034578 Multiple myelomas Diseases 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
108010057466 NF-kappa B Proteins 0.000 description 1
102000003945 NF-kappa B Human genes 0.000 description 1
208000008846 Neurocytoma Diseases 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
206010030155 Oesophageal carcinoma Diseases 0.000 description 1
208000012247 Oligodendroglial tumor Diseases 0.000 description 1
206010033128 Ovarian cancer Diseases 0.000 description 1
239000007990 PIPES buffer Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101150024701 PPH3 gene Proteins 0.000 description 1
241001111421 Pannus Species 0.000 description 1
229910002666 PdCl2 Inorganic materials 0.000 description 1
206010035226 Plasma cell myeloma Diseases 0.000 description 1
201000007288 Pleomorphic xanthoastrocytoma Diseases 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000006265 Renal cell carcinoma Diseases 0.000 description 1
NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
206010041067 Small cell lung cancer Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
208000021712 Soft tissue sarcoma Diseases 0.000 description 1
206010041660 Splenomegaly Diseases 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000001662 Subependymal Glioma Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000033540 T cell apoptotic process Effects 0.000 description 1
DLAQLPWTEPAWGC-UHFFFAOYSA-N TAN-1813 Natural products O=C1NC(=O)C(C(C=C)CCCCC)=C1C(=O)C1C2C(C)CC(C(O)=O)CC2(O)C=CC1C DLAQLPWTEPAWGC-UHFFFAOYSA-N 0.000 description 1
NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000033781 Thyroid carcinoma Diseases 0.000 description 1
208000024770 Thyroid neoplasm Diseases 0.000 description 1
SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 description 1
239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
229940123468 Transferase inhibitor Drugs 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
241000700605 Viruses Species 0.000 description 1
208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
208000008383 Wilms tumor Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
229960004748 abacavir Drugs 0.000 description 1
MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000007960 acetonitrile Chemical class 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 1
229960004176 aclarubicin Drugs 0.000 description 1
208000017733 acquired polycythemia vera Diseases 0.000 description 1
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
230000010398 acute inflammatory response Effects 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
208000020990 adrenal cortex carcinoma Diseases 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
229940040563 agaric acid Drugs 0.000 description 1
230000032683 aging Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229960001445 alitretinoin Drugs 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229960001830 amprenavir Drugs 0.000 description 1
YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 1
208000013938 anaplastic oligoastrocytoma Diseases 0.000 description 1
230000019552 anatomical structure morphogenesis Effects 0.000 description 1
239000004037 angiogenesis inhibitor Substances 0.000 description 1
229940121369 angiogenesis inhibitor Drugs 0.000 description 1
238000002399 angioplasty Methods 0.000 description 1
230000001772 anti-angiogenic effect Effects 0.000 description 1
239000000063 antileukemic agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000005775 apoptotic pathway Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005018 aryl alkenyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
229940120638 avastin Drugs 0.000 description 1
229960002756 azacitidine Drugs 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 1
108700041737 bcl-2 Genes Proteins 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
229960000397 bevacizumab Drugs 0.000 description 1
229960002938 bexarotene Drugs 0.000 description 1
201000001531 bladder carcinoma Diseases 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
229960002092 busulfan Drugs 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
229940127093 camptothecin Drugs 0.000 description 1
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
208000002458 carcinoid tumor Diseases 0.000 description 1
238000012754 cardiac puncture Methods 0.000 description 1
229960005243 carmustine Drugs 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
101150112018 ced-4 gene Proteins 0.000 description 1
229960000590 celecoxib Drugs 0.000 description 1
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
230000036755 cellular response Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
201000007455 central nervous system cancer Diseases 0.000 description 1
229960005110 cerivastatin Drugs 0.000 description 1
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
208000019065 cervical carcinoma Diseases 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
229940061627 chloromethyl methyl ether Drugs 0.000 description 1
229940075419 choline hydroxide Drugs 0.000 description 1
208000013940 chordoid glioma of the third ventricle Diseases 0.000 description 1
210000003161 choroid Anatomy 0.000 description 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
229950009003 cilengitide Drugs 0.000 description 1
AMLYAMJWYAIXIA-VWNVYAMZSA-N cilengitide Chemical compound N1C(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](C(C)C)N(C)C(=O)[C@H]1CC1=CC=CC=C1 AMLYAMJWYAIXIA-VWNVYAMZSA-N 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000011281 clinical therapy Methods 0.000 description 1
229960001338 colchicine Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000139 costimulatory effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000002559 cytogenic effect Effects 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
229960000640 dactinomycin Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000002074 deregulated effect Effects 0.000 description 1
208000030263 desmoplastic infantile astrocytoma Diseases 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
230000005750 disease progression Effects 0.000 description 1
VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
238000004821 distillation Methods 0.000 description 1
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
229960003668 docetaxel Drugs 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
201000004428 dysembryoplastic neuroepithelial tumor Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
206010014599 encephalitis Diseases 0.000 description 1
201000003914 endometrial carcinoma Diseases 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000036566 epidermal hyperplasia Effects 0.000 description 1
229960001433 erlotinib Drugs 0.000 description 1
201000005619 esophageal carcinoma Diseases 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000005284 excitation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 1
239000013604 expression vector Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
201000001169 fibrillary astrocytoma Diseases 0.000 description 1
238000009093 first-line therapy Methods 0.000 description 1
ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
229960000390 fludarabine Drugs 0.000 description 1
GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
208000024386 fungal infectious disease Diseases 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
206010017758 gastric cancer Diseases 0.000 description 1
208000010749 gastric carcinoma Diseases 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
229940045109 genistein Drugs 0.000 description 1
TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
235000006539 genistein Nutrition 0.000 description 1
ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
229940080856 gleevec Drugs 0.000 description 1
238000000227 grinding Methods 0.000 description 1
208000035474 group of disease Diseases 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
201000009277 hairy cell leukemia Diseases 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
210000003128 head Anatomy 0.000 description 1
201000003911 head and neck carcinoma Diseases 0.000 description 1
230000004730 hepatocarcinogenesis Effects 0.000 description 1
125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
239000003906 humectant Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
230000003463 hyperproliferative effect Effects 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
229960002411 imatinib Drugs 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
230000008076 immune mechanism Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000012678 infectious agent Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000016507 interphase Effects 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
229960005280 isotretinoin Drugs 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000011694 lewis rat Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
208000030173 low grade glioma Diseases 0.000 description 1
208000022080 low-grade astrocytoma Diseases 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
201000005296 lung carcinoma Diseases 0.000 description 1
201000000564 macroglobulinemia Diseases 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012092 media component Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
208000014490 mixed neuronal-glial tumor Diseases 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
230000035772 mutation Effects 0.000 description 1
201000005962 mycosis fungoides Diseases 0.000 description 1
QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
HFOHAGDMJREQFE-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-2-methylquinazolin-4-amine Chemical compound FC1=CC(OC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 HFOHAGDMJREQFE-UHFFFAOYSA-N 0.000 description 1
YIIGIBAOCUPZAH-UHFFFAOYSA-N n-(4-ethoxyphenyl)-2-methylquinazolin-4-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 YIIGIBAOCUPZAH-UHFFFAOYSA-N 0.000 description 1
MSJDZQAPAIGAFY-UHFFFAOYSA-N n-(4-ethylphenyl)-2-methylquinazolin-4-amine Chemical compound C1=CC(CC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 MSJDZQAPAIGAFY-UHFFFAOYSA-N 0.000 description 1
SNHCRNMVYDHVDT-UHFFFAOYSA-N n-(4-methoxyphenyl)-n,2-dimethylquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=NC(C)=NC2=CC=CC=C12 SNHCRNMVYDHVDT-UHFFFAOYSA-N 0.000 description 1
UOXZCDRAYWOOTQ-UHFFFAOYSA-N n-(5-methoxypyridin-2-yl)-2-methylquinazolin-4-amine Chemical compound N1=CC(OC)=CC=C1NC1=NC(C)=NC2=CC=CC=C12 UOXZCDRAYWOOTQ-UHFFFAOYSA-N 0.000 description 1
UPSFMJHZUCSEHU-JYGUBCOQSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@H](OC=2C=C3OC(=O)C=C(C)C3=CC=2)O[C@@H]1CO UPSFMJHZUCSEHU-JYGUBCOQSA-N 0.000 description 1
IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 description 1
MGCCWCLGIPNIBP-UHFFFAOYSA-N n-methyl-4-(trifluoromethoxy)aniline Chemical compound CNC1=CC=C(OC(F)(F)F)C=C1 MGCCWCLGIPNIBP-UHFFFAOYSA-N 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000006654 negative regulation of apoptotic process Effects 0.000 description 1
229960000884 nelfinavir Drugs 0.000 description 1
QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
208000007538 neurilemmoma Diseases 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
230000037311 normal skin Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
206010073131 oligoastrocytoma Diseases 0.000 description 1
210000004248 oligodendroglia Anatomy 0.000 description 1
GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
201000008968 osteosarcoma Diseases 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003973 paint Substances 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
208000021255 pancreatic insulinoma Diseases 0.000 description 1
208000003154 papilloma Diseases 0.000 description 1
208000007312 paraganglioma Diseases 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
210000000578 peripheral nerve Anatomy 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
210000001539 phagocyte Anatomy 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
230000009894 physiological stress Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
208000037244 polycythemia vera Diseases 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
208000029340 primitive neuroectodermal tumor Diseases 0.000 description 1
230000000861 pro-apoptotic effect Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000006920 protein precipitation Effects 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
201000009410 rhabdomyosarcoma Diseases 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229960000311 ritonavir Drugs 0.000 description 1
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
229960000371 rofecoxib Drugs 0.000 description 1
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
BTIHMVBBUGXLCJ-OAHLLOKOSA-N seliciclib Chemical compound C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1NCC1=CC=CC=C1 BTIHMVBBUGXLCJ-OAHLLOKOSA-N 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
108010040167 sigma-2 receptor Proteins 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
229960002930 sirolimus Drugs 0.000 description 1
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000012439 solid excipient Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
201000000498 stomach carcinoma Diseases 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
201000004059 subependymal giant cell astrocytoma Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
201000008205 supratentorial primitive neuroectodermal tumor Diseases 0.000 description 1
210000001258 synovial membrane Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
DLAQLPWTEPAWGC-OZDNBXTOSA-N tan-1813 Chemical compound O=C1NC(=O)C([C@H](C=C)CCCCC)=C1C(=O)C1C2[C@@H](C)C[C@@H](C(O)=O)C[C@@]2(O)C=C[C@H]1C DLAQLPWTEPAWGC-OZDNBXTOSA-N 0.000 description 1
229940120982 tarceva Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 description 1
230000002381 testicular Effects 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000000211 third ventricle Anatomy 0.000 description 1
201000002510 thyroid cancer Diseases 0.000 description 1
208000013077 thyroid gland carcinoma Diseases 0.000 description 1
229960003087 tioguanine Drugs 0.000 description 1
229960000838 tipranavir Drugs 0.000 description 1
SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 description 1
230000025366 tissue development Effects 0.000 description 1
230000030968 tissue homeostasis Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229960002004 valdecoxib Drugs 0.000 description 1
LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
238000010200 validation analysis Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
244000052613 viral pathogen Species 0.000 description 1
230000008957 viral persistence Effects 0.000 description 1
210000002845 virion Anatomy 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002592971A 2005-01-03 2006-01-03 Methode de traitement du cancer du cerveau Abandoned CA2592971A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US64126305P	2005-01-03	2005-01-03
US60/641,263		2005-01-03
PCT/US2006/000122 WO2006074187A2 (fr)	2005-01-03	2006-01-03	Methode de traitement du cancer du cerveau

Publications (1)

Publication Number	Publication Date
CA2592971A1 true CA2592971A1 (fr)	2006-07-13

Family

ID=36648123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002592971A Abandoned CA2592971A1 (fr)	2005-01-03	2006-01-03	Methode de traitement du cancer du cerveau

Country Status (7)

Country	Link
EP (1)	EP1833511A4 (fr)
JP (1)	JP2008526776A (fr)
KR (1)	KR20070117547A (fr)
CN (1)	CN101287369A (fr)
AU (1)	AU2006204052A1 (fr)
CA (1)	CA2592971A1 (fr)
WO (1)	WO2006074187A2 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050267182A1 (en)	2003-11-13	2005-12-01	Ambit Biosciences Corporation	Urea derivatives as FLT-3 modulators
EP2144887A4 (fr) *	2007-04-10	2012-10-03	Myrexis Inc	Doses et méthodes de traitement du cancer
KR20100016385A (ko) *	2007-04-10	2010-02-12	미리어드 파마슈티칼스, 인코포레이티드	뇌종양 치료방법
FR2932180B1 (fr) *	2008-06-04	2012-08-10	Centre Nat Rech Scient	Dihydro iso ca-4 et analogues : puissants cytotoxiques, inhibiteurs de la polymerisation de la tubuline
AU2012228334B2 (en)	2011-03-15	2017-03-23	Chiesi Farmaceutici S.P.A.	Isoxazolidine derivatives
AR085816A1 (es)	2011-03-15	2013-10-30	Chiesi Farma Spa	Derivados de isoxazolidina
FR3019819B1 (fr)	2014-04-09	2018-03-23	Centre National De La Recherche Scientifique (Cnrs)	Composes cytotoxiques inhibiteurs de la polymerisation de la tubuline
EP3601267A1 (fr)	2017-03-21	2020-02-05	Bayer Pharma Aktiengesellschaft	2-méthyl-quinazolines
CA3097231A1 (fr)	2018-04-18	2019-10-24	Bayer Pharma Aktiengesellschaft	2-methyl-aza-quinazolines
FR3080620B1 (fr)	2018-04-27	2021-11-12	Univ Paris Sud	Composes a activite inhibitrice de la polymerisation de la tubuline et aux proprietes immunomodulatrices

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL88507A (en) *	1987-12-03	1993-02-21	Smithkline Beckman Intercredit	2,4-diaminoquinazolines, process for their preparation and pharmaceutical compositions comprising them
DE69202243T2 (de) *	1991-02-20	1995-08-31	Pfizer	2,4-Diaminochinazolin-Derivate, um die Antitumorwirkung zu erhöhen.
AU4342997A (en) *	1996-09-13	1998-04-02	Sugen, Inc.	Use of quinazoline derivatives for the manufacture of a medicament in the reatment of hyperproliferative skin disorders
WO1999061428A1 (fr) *	1998-05-28	1999-12-02	Parker Hughes Institute	Utilisation des quinazolines pour le traitement de tumeurs cerebrales
UA71945C2 (en) *	1999-01-27	2005-01-17	Pfizer Prod Inc	Substituted bicyclic derivatives being used as anticancer agents
WO2005003100A2 (fr) *	2003-07-03	2005-01-13	Myriad Genetics, Inc.	Composes et leur utilisation therapeutique
WO2006074147A2 (fr) *	2005-01-03	2006-07-13	Myriad Genetics, Inc.	Composes et utilisation therapeutique associee
US20060025406A1 (en) *	2004-07-06	2006-02-02	Angion Biomedica Corporation	Modulators of hepatocyte growth factor/c- Met activity

2006
- 2006-01-03 CN CNA2006800025252A patent/CN101287369A/zh active Pending
- 2006-01-03 AU AU2006204052A patent/AU2006204052A1/en not_active Abandoned
- 2006-01-03 KR KR1020077017960A patent/KR20070117547A/ko not_active Application Discontinuation
- 2006-01-03 EP EP06717342A patent/EP1833511A4/fr not_active Withdrawn
- 2006-01-03 CA CA002592971A patent/CA2592971A1/fr not_active Abandoned
- 2006-01-03 WO PCT/US2006/000122 patent/WO2006074187A2/fr active Application Filing
- 2006-01-03 JP JP2007549710A patent/JP2008526776A/ja active Pending

Also Published As

Publication number	Publication date
KR20070117547A (ko)	2007-12-12
WO2006074187A3 (fr)	2008-01-10
WO2006074187A2 (fr)	2006-07-13
CN101287369A (zh)	2008-10-15
EP1833511A4 (fr)	2011-01-19
EP1833511A2 (fr)	2007-09-19
JP2008526776A (ja)	2008-07-24
AU2006204052A1 (en)	2006-07-13

Publication	Publication Date	Title
JP5129957B2 (ja)	2013-01-30	カスパーゼの活性化因子およびアポトーシスの誘発因子としての４−アリールアミノ−キナゾリン
US7989462B2 (en)	2011-08-02	4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8309562B2 (en)	2012-11-13	Compounds and therapeutical use thereof
US8258145B2 (en)	2012-09-04	Method of treating brain cancer
US20070099877A1 (en)	2007-05-03	N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US20070213305A1 (en)	2007-09-13	N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
WO2008057402A2 (fr)	2008-05-15	N-aryl-isoxazolopyrimidin-4-amines et composés associés servant d'activateurs de caspases et d'inducteurs d'apoptose et leur utilisation
US7842805B2 (en)	2010-11-30	Pharmaceutical compounds as activators of caspases and inducers of apoptosis and the use thereof
WO2008021456A2 (fr)	2008-02-21	N-aryl-5,7-dihydrofuro[3,4-d]pyrimidin-4-amines et analogues en tant qu'activateurs de caspases et inducteurs d'apoptose, et leurs utilisations
CA2592971A1 (fr)	2006-07-13	Methode de traitement du cancer du cerveau
US20070244114A1 (en)	2007-10-18	Compounds and therapeutical use thereof
WO2009094205A2 (fr)	2009-07-30	3-aryl-6-aryl-7h-[1,2,4]triazolo[3,4-b][1,3,4]thiadazines et analogues en tant qu'activateurs de caspases et inducteurs d'apoptose, et leur utilisation
US20080096848A1 (en)	2008-04-24	Substituted N-Aryl-9-Oxo-9H-Fluorene-1-Carboxamides and Analogs as Activators of Caspases and Inducers of Apoptosis

Legal Events

Date	Code	Title	Description
2012-01-03	FZDE	Discontinued