HRP20010946A2 - Naphthyridine derivatives, processes for their preparation, their use and pharmaceutical compositions comprising them - Google Patents

Naphthyridine derivatives, processes for their preparation, their use and pharmaceutical compositions comprising them Download PDF

Info

Publication number: HRP20010946A2
Authority: HR; Croatia
Prior art keywords: alkyl; aryl; heteroaryl; zero; cycloalkyl
Prior art date: 1999-07-02

Application number

HR20010946A

Other languages

English (en)

Croatian (hr)

Inventor

Anuschirvan Peyman

Jean-Marie Ruxer

Karlheinz Scheunemann

Jean-Francois Gourvest

Original Assignee

Aventis Pharma Gmbh

Genentech Inc

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.)

1999-07-02

Filing date

2001-12-21

Publication date

2003-02-28

2001-12-21 Application filed by Aventis Pharma Gmbh, Genentech Inc filed Critical Aventis Pharma Gmbh

2003-02-28 Publication of HRP20010946A2 publication Critical patent/HRP20010946A2/hr

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 11
239000008194 pharmaceutical composition Substances 0.000 title description 4
150000005054 naphthyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 195
-1 nitro, hydroxycarbonyl - Chemical class 0.000 claims description 102
229910052739 hydrogen Inorganic materials 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 57
239000003814 drug Substances 0.000 claims description 51
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 50
229940079593 drug Drugs 0.000 claims description 50
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 46
239000000460 chlorine Substances 0.000 claims description 46
229910052801 chlorine Inorganic materials 0.000 claims description 46
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
239000011737 fluorine Substances 0.000 claims description 42
229910052731 fluorine Inorganic materials 0.000 claims description 42
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
125000004093 cyano group Chemical group *C#N 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 34
102100022337 Integrin alpha-V Human genes 0.000 claims description 32
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 31
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
229910052794 bromium Inorganic materials 0.000 claims description 30
108010048673 Vitronectin Receptors Proteins 0.000 claims description 28
125000005842 heteroatom Chemical group 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 25
CIDSGDKXNGKZIH-UHFFFAOYSA-N 4-N-(1-tert-butylsulfonyl-2,3-dihydroindol-6-yl)-2-N-[3-fluoro-4-(1-methylpiperidin-4-yl)phenyl]-5-methylpyrimidine-2,4-diamine Chemical compound C(C)(C)(C)S(=O)(=O)N1CCC2=CC=C(C=C12)NC1=NC(=NC=C1C)NC1=CC(=C(C=C1)C1CCN(CC1)C)F CIDSGDKXNGKZIH-UHFFFAOYSA-N 0.000 claims description 24
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
150000002431 hydrogen Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
HGADNQLEUZSUEJ-OAHLLOKOSA-N o6-(r)-roscovitine, r-2-(6-benzyloxy-9-isopropyl-9h-purin-2-ylamino)-butan-1-ol Chemical compound C=12N=CN(C(C)C)C2=NC(N[C@@H](CO)CC)=NC=1OCC1=CC=CC=C1 HGADNQLEUZSUEJ-OAHLLOKOSA-N 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 21
239000001301 oxygen Substances 0.000 claims description 21
238000011321 prophylaxis Methods 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 20
239000011593 sulfur Substances 0.000 claims description 20
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 18
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 17
239000000825 pharmaceutical preparation Substances 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
125000000524 functional group Chemical group 0.000 claims description 14
239000003112 inhibitor Substances 0.000 claims description 14
208000001132 Osteoporosis Diseases 0.000 claims description 11
125000000732 arylene group Chemical group 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 11
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 10
239000002243 precursor Substances 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
SCNPUDCZXNUNQZ-UHFFFAOYSA-N 4-(furan-2-yl)-1-[(4-methoxyphenyl)methyl]pyrazolo[3,4-d]pyrimidine Chemical group C1=CC(OC)=CC=C1CN1C2=NC=NC(C=3OC=CC=3)=C2C=N1 SCNPUDCZXNUNQZ-UHFFFAOYSA-N 0.000 claims description 9
101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 9
150000001450 anions Chemical class 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
206010027476 Metastases Diseases 0.000 claims description 4
125000000539 amino acid group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
239000002464 receptor antagonist Substances 0.000 claims description 4
229940044551 receptor antagonist Drugs 0.000 claims description 4
208000037803 restenosis Diseases 0.000 claims description 4
230000004614 tumor growth Effects 0.000 claims description 4
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201000004681 Psoriasis Diseases 0.000 claims description 3
206010038923 Retinopathy Diseases 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
230000009401 metastasis Effects 0.000 claims description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
229940078581 Bone resorption inhibitor Drugs 0.000 claims description 2
208000017442 Retinal disease Diseases 0.000 claims description 2
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
239000002260 anti-inflammatory agent Substances 0.000 claims description 2
239000002617 bone density conservation agent Substances 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
208000017169 kidney disease Diseases 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
206010003210 Arteriosclerosis Diseases 0.000 claims 1
208000011775 arteriosclerosis disease Diseases 0.000 claims 1
210000004027 cell Anatomy 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
210000002997 osteoclast Anatomy 0.000 description 19
208000006386 Bone Resorption Diseases 0.000 description 18
230000024279 bone resorption Effects 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000002560 therapeutic procedure Methods 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000004480 active ingredient Substances 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
210000000988 bone and bone Anatomy 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
238000012360 testing method Methods 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
201000010099 disease Diseases 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000005557 antagonist Substances 0.000 description 9
101000803709 Homo sapiens Vitronectin Proteins 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
230000003993 interaction Effects 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
238000003756 stirring Methods 0.000 description 8
ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical group C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 7
229940024606 amino acid Drugs 0.000 description 7
235000001014 amino acid Nutrition 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
125000002619 bicyclic group Chemical group 0.000 description 7
239000000872 buffer Substances 0.000 description 7
239000000969 carrier Substances 0.000 description 7
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
239000002953 phosphate buffered saline Substances 0.000 description 7
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 7
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
230000033115 angiogenesis Effects 0.000 description 6
239000002585 base Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229940011871 estrogen Drugs 0.000 description 6
239000000262 estrogen Substances 0.000 description 6
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000002950 monocyclic group Chemical group 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
239000003826 tablet Substances 0.000 description 6
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 5
IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 5
208000020084 Bone disease Diseases 0.000 description 5
108091003079 Bovine Serum Albumin Proteins 0.000 description 5
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
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238000001914 filtration Methods 0.000 description 5
108010059557 kistrin Proteins 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
ZTYNVDHJNRIRLL-FWZKYCSMSA-N rhodostomin Chemical compound C([C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H]2C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCSC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CSSC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(O)=O)[C@@H](C)O)=O)CSSC[C@H]2C(=O)N[C@H]3CSSC[C@@H](C(NCC(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H]2CCCN2C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H]2NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H]4CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)CN)CSSC2)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N2CCC[C@H]2C(=O)N[C@H](C(N4)=O)CSSC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC3=O)C(=O)N[C@@H](CCCCN)C(=O)N1)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=CC=C1 ZTYNVDHJNRIRLL-FWZKYCSMSA-N 0.000 description 5
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
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125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
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241000283973 Oryctolagus cuniculus Species 0.000 description 3
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RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
102100040949 mRNA cap guanine-N7 methyltransferase Human genes 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
229940097496 nasal spray Drugs 0.000 description 1
230000010807 negative regulation of binding Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
150000007523 nucleic acids Chemical class 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
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000000913 palmityl 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])C([H])([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
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002993 phenylalanine derivatives Chemical class 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
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
229960002429 proline Drugs 0.000 description 1
125000006410 propenylene group Chemical group 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
230000000707 stereoselective effect Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002626 targeted therapy Methods 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
KEGGPKIRWQIHQT-LBPRGKRZSA-N tert-butyl (2s)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate Chemical compound CC(C)(C)OC(=O)[C@H](CO)NC(=O)OCC1=CC=CC=C1 KEGGPKIRWQIHQT-LBPRGKRZSA-N 0.000 description 1
HNVBBNZWMSTMAZ-UHFFFAOYSA-N tert-butyl 4-acetylpiperidine-1-carboxylate Chemical compound CC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 HNVBBNZWMSTMAZ-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
MZCYAJMPNWAUMV-UHFFFAOYSA-N tricyclo[5.4.0.02,9]undecane Chemical compound C1CCCC2C3CC1C2CC3 MZCYAJMPNWAUMV-UHFFFAOYSA-N 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Dermatology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

HR20010946A 1999-07-02 2001-12-21 Naphthyridine derivatives, processes for their preparation, their use and pharmaceutical compositions comprising them HRP20010946A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99112636A EP1065207A1 (fr)	1999-07-02	1999-07-02	Dérivées de la naphthyridine, procédés pour leur preparation, leur utilisation, et compositions pharmaceutique les contenant
PCT/EP2000/005920 WO2001002398A1 (fr)	1999-07-02	2000-06-26	Derives de naphthyridine, procede de preparation, utilisation et compositions pharmaceutiques les renfermant

Publications (1)

Publication Number	Publication Date
HRP20010946A2 true HRP20010946A2 (en)	2003-02-28

Family

ID=8238482

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20010946A HRP20010946A2 (en)	1999-07-02	2001-12-21	Naphthyridine derivatives, processes for their preparation, their use and pharmaceutical compositions comprising them

Country Status (33)

Country	Link
US (2)	US6743800B1 (fr)
EP (2)	EP1065207A1 (fr)
JP (1)	JP2003503496A (fr)
KR (1)	KR20020015996A (fr)
CN (1)	CN1160356C (fr)
AR (1)	AR024622A1 (fr)
AT (1)	ATE305471T1 (fr)
AU (1)	AU775386B2 (fr)
BG (1)	BG106257A (fr)
BR (1)	BR0012129A (fr)
CA (1)	CA2376668C (fr)
CZ (1)	CZ20014605A3 (fr)
DE (2)	DE60022890T4 (fr)
DK (1)	DK1210348T3 (fr)
EA (1)	EA004369B1 (fr)
EE (1)	EE200100711A (fr)
ES (1)	ES2250157T3 (fr)
HK (1)	HK1050003B (fr)
HR (1)	HRP20010946A2 (fr)
HU (1)	HUP0203539A3 (fr)
IL (1)	IL147248A0 (fr)
MX (1)	MXPA01013435A (fr)
MY (1)	MY133246A (fr)
NO (1)	NO20016404L (fr)
NZ (1)	NZ516058A (fr)
PL (1)	PL352280A1 (fr)
SK (1)	SK19132001A3 (fr)
TR (1)	TR200103856T2 (fr)
TW (1)	TW593319B (fr)
UA (1)	UA73133C2 (fr)
WO (1)	WO2001002398A1 (fr)
YU (1)	YU92201A (fr)
ZA (1)	ZA200200016B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1065207A1 (fr) *	1999-07-02	2001-01-03	Aventis Pharma Deutschland GmbH	Dérivées de la naphthyridine, procédés pour leur preparation, leur utilisation, et compositions pharmaceutique les contenant
DE10042655A1 (de)	2000-08-31	2002-03-14	Aventis Pharma Gmbh	Verfahren zur Herstellung von Inhibitoren der Zell-Adhäsion
FR2847254B1 (fr)	2002-11-19	2005-01-28	Aventis Pharma Sa	Nouveaux derives antagonistes du recepteur de la vitronectine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les refermant
JP4866610B2 (ja) *	2003-08-18	2012-02-01	富士フイルムファインケミカルズ株式会社	ピリジルテトラヒドロピリジン類およびピリジルピペリジン類
FR2870541B1 (fr)	2004-05-18	2006-07-14	Proskelia Sas	Derives de pyrimidines antigonistes du recepteur de la vitronectine
US20110237605A1 (en)	2010-03-26	2011-09-29	Eric Phillips	Molecular Crystal of (4-(1,8-Naphthyridin-2-YL)Piperidin-1-YL)Pyrimidine Derivative
CN103665043B (zh)	2012-08-30	2017-11-10	江苏豪森药业集团有限公司	一种替诺福韦前药及其在医药上的应用
SI3929196T1 (sl)	2013-09-24	2023-11-30	Fujifilm Corporation	Farmacevtska sestava spojine, ki vsebuje dušik ali njegovo sol ali njegov kovinski kompleks
US11691963B2 (en)	2020-05-06	2023-07-04	Ajax Therapeutics, Inc.	6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors
TW202241889A (zh)	2020-12-23	2022-11-01	美商雅捷可斯治療公司	作為ｊａｋ２抑制劑之６－雜芳基氧基苯并咪唑及氮雜苯并咪唑
US11970494B2 (en)	2021-11-09	2024-04-30	Ajax Therapeutics, Inc.	6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors

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ATE227567T1 (de) *	1994-05-27	2002-11-15	Merck & Co Inc	Präparate zur hemmung der durch osteoklasten vermittelten knochenresorption
AU3938997A (en)	1996-08-26	1998-03-19	Novo Nordisk A/S	A novel endoglucanase
JP2002511052A (ja) *	1996-08-29	2002-04-09	メルクエンドカンパニーインコーポレーテッド	インテグリンアンタゴニスト
WO1998018461A1 (fr) *	1996-10-30	1998-05-07	Merck & Co., Inc.	Antagonistes de l'integrine
DE19653646A1 (de) *	1996-12-20	1998-06-25	Hoechst Ag	Substituierte Purinderivate, Verfahren zu deren Herstellung, sie enthaltende Mittel und deren Verwendung
AU729869B2 (en) *	1997-01-17	2001-02-15	Merck & Co., Inc.	Integrin antagonists
EP0933367A1 (fr) *	1997-12-19	1999-08-04	Hoechst Marion Roussel Deutschland GmbH	Dérivés d'acylguanidine comme inhibiteurs de résorbtion osseuse et comme antagonistes de récepteur vitronectine
HUP0100520A3 (en) *	1998-01-23	2002-11-28	Genentech Inc	Novel sulfonamide derivatives as inhibitors of bone resorption and as inhibitors of cell adhesion
PA8474101A1 (es) *	1998-06-19	2000-09-29	Pfizer Prod Inc	Compuestos de pirrolo [2,3-d] pirimidina
US6365589B1 (en) *	1998-07-02	2002-04-02	Bristol-Myers Squibb Pharma Company	Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists
EP1065207A1 (fr) *	1999-07-02	2001-01-03	Aventis Pharma Deutschland GmbH	Dérivées de la naphthyridine, procédés pour leur preparation, leur utilisation, et compositions pharmaceutique les contenant
DE10042655A1 (de) *	2000-08-31	2002-03-14	Aventis Pharma Gmbh	Verfahren zur Herstellung von Inhibitoren der Zell-Adhäsion
WO2003059289A2 (fr) *	2002-01-10	2003-07-24	Neurogen Corporation	Ligands recepteurs de l'hormone de concentration de la melanine: analogues de benzoimidazole substitue
JP2008047614A (ja)	2006-08-11	2008-02-28	Showa Shell Sekiyu Kk	吸着材を利用した改良型太陽電池モジュール

1999
- 1999-07-02 EP EP99112636A patent/EP1065207A1/fr not_active Withdrawn
2000
- 2000-06-26 DK DK00945825T patent/DK1210348T3/da active
- 2000-06-26 CN CNB008123365A patent/CN1160356C/zh not_active Expired - Fee Related
- 2000-06-26 CA CA002376668A patent/CA2376668C/fr not_active Expired - Fee Related
- 2000-06-26 EP EP00945825A patent/EP1210348B9/fr not_active Expired - Lifetime
- 2000-06-26 AU AU59787/00A patent/AU775386B2/en not_active Ceased
- 2000-06-26 ES ES00945825T patent/ES2250157T3/es not_active Expired - Lifetime
- 2000-06-26 NZ NZ516058A patent/NZ516058A/xx unknown
- 2000-06-26 YU YU92201A patent/YU92201A/sh unknown
- 2000-06-26 UA UA2002020852A patent/UA73133C2/uk unknown
- 2000-06-26 HU HU0203539A patent/HUP0203539A3/hu unknown
- 2000-06-26 PL PL00352280A patent/PL352280A1/xx not_active Application Discontinuation
- 2000-06-26 DE DE60022890T patent/DE60022890T4/de not_active Expired - Lifetime
- 2000-06-26 EE EEP200100711A patent/EE200100711A/xx unknown
- 2000-06-26 MX MXPA01013435A patent/MXPA01013435A/es active IP Right Grant
- 2000-06-26 TR TR2001/03856T patent/TR200103856T2/xx unknown
- 2000-06-26 DE DE60022890A patent/DE60022890D1/de not_active Expired - Fee Related
- 2000-06-26 WO PCT/EP2000/005920 patent/WO2001002398A1/fr not_active Application Discontinuation
- 2000-06-26 IL IL14724800A patent/IL147248A0/xx unknown
- 2000-06-26 JP JP2001507835A patent/JP2003503496A/ja not_active Withdrawn
- 2000-06-26 EA EA200200122A patent/EA004369B1/ru not_active IP Right Cessation
- 2000-06-26 US US10/030,301 patent/US6743800B1/en not_active Expired - Fee Related
- 2000-06-26 KR KR1020017016961A patent/KR20020015996A/ko not_active Application Discontinuation
- 2000-06-26 AT AT00945825T patent/ATE305471T1/de not_active IP Right Cessation
- 2000-06-26 SK SK1913-2001A patent/SK19132001A3/sk unknown
- 2000-06-26 BR BR0012129-0A patent/BR0012129A/pt not_active IP Right Cessation
- 2000-06-26 CZ CZ20014605A patent/CZ20014605A3/cs unknown
- 2000-06-29 MY MYPI20002962 patent/MY133246A/en unknown
- 2000-06-29 AR ARP000103313A patent/AR024622A1/es active IP Right Grant
- 2000-09-01 TW TW089117925A patent/TW593319B/zh not_active IP Right Cessation
2001
- 2001-12-20 BG BG106257A patent/BG106257A/bg unknown
- 2001-12-21 HR HR20010946A patent/HRP20010946A2/hr not_active Application Discontinuation
- 2001-12-28 NO NO20016404A patent/NO20016404L/no not_active Application Discontinuation
2002
- 2002-01-02 ZA ZA200200016A patent/ZA200200016B/en unknown
2003
- 2003-03-25 HK HK03102163.4A patent/HK1050003B/zh not_active IP Right Cessation
2004
- 2004-03-24 US US10/808,496 patent/US20040198718A1/en not_active Abandoned

Also Published As

Publication number	Publication date
HK1050003B (zh)	2005-04-29
NZ516058A (en)	2003-01-31
US20040198718A1 (en)	2004-10-07
EA200200122A1 (ru)	2002-06-27
AR024622A1 (es)	2002-10-16
EP1210348B1 (fr)	2005-09-28
DK1210348T3 (da)	2006-01-16
JP2003503496A (ja)	2003-01-28
EE200100711A (et)	2003-04-15
DE60022890T2 (de)	2006-06-29
CA2376668C (fr)	2007-01-02
MXPA01013435A (es)	2002-07-22
EA004369B1 (ru)	2004-04-29
HK1050003A1 (en)	2003-06-06
MY133246A (en)	2007-10-31
ZA200200016B (en)	2003-01-02
HUP0203539A2 (hu)	2003-02-28
CA2376668A1 (fr)	2001-01-11
UA73133C2 (en)	2005-06-15
US6743800B1 (en)	2004-06-01
EP1210348B9 (fr)	2006-04-26
BR0012129A (pt)	2002-05-07
ATE305471T1 (de)	2005-10-15
AU5978700A (en)	2001-01-22
IL147248A0 (en)	2002-08-14
SK19132001A3 (sk)	2002-07-02
CN1160356C (zh)	2004-08-04
WO2001002398A1 (fr)	2001-01-11
KR20020015996A (ko)	2002-03-02
EP1065207A1 (fr)	2001-01-03
CZ20014605A3 (cs)	2002-06-12
NO20016404D0 (no)	2001-12-28
NO20016404L (no)	2002-03-01
PL352280A1 (en)	2003-08-11
EP1210348A1 (fr)	2002-06-05
DE60022890D1 (de)	2006-02-09
CN1372559A (zh)	2002-10-02
BG106257A (bg)	2002-10-31
AU775386B2 (en)	2004-07-29
DE60022890T4 (de)	2007-03-29
YU92201A (sh)	2004-07-15
TW593319B (en)	2004-06-21
TR200103856T2 (tr)	2002-06-21
HUP0203539A3 (en)	2005-01-28
ES2250157T3 (es)	2006-04-16

Publication	Publication Date	Title
JP4620190B2 (ja)	2011-01-26	置換プリン誘導体、その製法、その使用およびそれを含有する組成物
HRP20010946A2 (en)	2003-02-28	Naphthyridine derivatives, processes for their preparation, their use and pharmaceutical compositions comprising them
US6747016B1 (en)	2004-06-08	Substituted purine derivatives as inhibitors of cell adhesion
EP1313737B1 (fr)	2009-06-03	Nouveaux derives de la guanidine utilises comme inhibiteurs de l'adhesion cellulaire

Legal Events

Date	Code	Title	Description
2002-04-15	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20020415 Year of fee payment: 3
2003-02-28	A1OB	Publication of a patent application
2003-07-30	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2006-09-11	ODBC	Application rejected