NO853859L - Triazolikinazolin-forbindelser. - Google Patents

Triazolikinazolin-forbindelser.

Info

Publication number: NO853859L
Authority: NO; Norway
Prior art keywords: lower alkyl; formula; compound; stands; acid
Prior art date: 1984-10-01

Application number

NO853859A

Other languages

English (en)

Norwegian (no)

Inventor

John E Francis

Karl O Gelotte

Original Assignee

Ciba Geigy Ag

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.)

1984-10-01

Filing date

1985-09-30

Publication date

1986-04-02

1985-09-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1986-04-02 Publication of NO853859L publication Critical patent/NO853859L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 72
125000000217 alkyl group Chemical group 0.000 claims description 68
229910052757 nitrogen Inorganic materials 0.000 claims description 60
-1 hydroxy, amino Chemical group 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
150000001721 carbon Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
239000007800 oxidant agent Substances 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
WOOIBJWFHSHPJN-UHFFFAOYSA-N 2h-triazolo[4,5-h]quinazoline Chemical group C1=CC2=NNN=C2C2=NC=NC=C21 WOOIBJWFHSHPJN-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
150000002540 isothiocyanates Chemical class 0.000 claims description 3
125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 2
238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 98
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
238000002844 melting Methods 0.000 description 68
230000008018 melting Effects 0.000 description 68
239000000203 mixture Substances 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
239000007787 solid Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 26
238000010992 reflux Methods 0.000 description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000001953 recrystallisation Methods 0.000 description 16
239000007858 starting material Substances 0.000 description 16
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 11
239000002585 base Substances 0.000 description 11
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
150000003852 triazoles Chemical class 0.000 description 10
238000001816 cooling Methods 0.000 description 9
239000000463 material Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
229940098779 methanesulfonic acid Drugs 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000000725 suspension Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 6
239000011343 solid material Substances 0.000 description 6
229910001220 stainless steel Inorganic materials 0.000 description 6
239000010935 stainless steel Substances 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 5
SKTSVWWOAIAIKI-UHFFFAOYSA-N furan-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CO1 SKTSVWWOAIAIKI-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 5
GDHYPPBFBJXNRE-UHFFFAOYSA-N 2-isothiocyanatobenzonitrile Chemical compound S=C=NC1=CC=CC=C1C#N GDHYPPBFBJXNRE-UHFFFAOYSA-N 0.000 description 4
HGZKGYSDLSMMKA-UHFFFAOYSA-N 5-chloro-2-isocyanatobenzonitrile Chemical compound ClC1=CC=C(N=C=O)C(C#N)=C1 HGZKGYSDLSMMKA-UHFFFAOYSA-N 0.000 description 4
MSJODEOZODDVGW-UHFFFAOYSA-N 9-chloro-2-(2-furanyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 MSJODEOZODDVGW-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
LJWMIJROWBUNJV-UHFFFAOYSA-N N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 Chemical compound N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 LJWMIJROWBUNJV-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
AXPGZURVLRWNBR-UHFFFAOYSA-N chembl330116 Chemical compound N=1N2C(O)=NC3=CC=CC=C3C2=NC=1C1=CC=CC=C1 AXPGZURVLRWNBR-UHFFFAOYSA-N 0.000 description 4
XEVZWKHGVYHGAM-UHFFFAOYSA-N chembl414023 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1=CC=CO1 XEVZWKHGVYHGAM-UHFFFAOYSA-N 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000012458 free base Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000004533 oil dispersion Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
CYDGREISJRDSDE-UHFFFAOYSA-N 2-amino-5-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC(Cl)=CC=C1N CYDGREISJRDSDE-UHFFFAOYSA-N 0.000 description 3
YJCCKQQVXNNAAR-UHFFFAOYSA-N 2-fluorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1F YJCCKQQVXNNAAR-UHFFFAOYSA-N 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
FQLNVWAFXQUXGW-UHFFFAOYSA-N 2-isocyanatobenzonitrile Chemical compound O=C=NC1=CC=CC=C1C#N FQLNVWAFXQUXGW-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
108010010803 Gelatin Proteins 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
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 3
239000002202 Polyethylene glycol Substances 0.000 description 3
239000004202 carbamide Substances 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
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 3
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000001475 halogen functional group Chemical group 0.000 description 3
239000008101 lactose Substances 0.000 description 3
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
UUSJUENFEGZBBT-UHFFFAOYSA-N 2-(furan-2-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N=1N2C(SC)=NC3=CC=CC=C3C2=NC=1C1=CC=CO1 UUSJUENFEGZBBT-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 2
HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
ACGJIIRRFHEHAB-UHFFFAOYSA-N 4-chloro-2-[5-(furan-2-yl)-1h-1,2,4-triazol-3-yl]aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C=2OC=CC=2)=N1 ACGJIIRRFHEHAB-UHFFFAOYSA-N 0.000 description 2
XJVKXLHNCRNMAV-UHFFFAOYSA-N 5-chloro-2-isothiocyanatobenzonitrile Chemical compound ClC1=CC=C(N=C=S)C(C#N)=C1 XJVKXLHNCRNMAV-UHFFFAOYSA-N 0.000 description 2
MYQFJMYJVJRSGP-UHFFFAOYSA-N 6-chloro-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C2=CC(Cl)=CC=C21 MYQFJMYJVJRSGP-UHFFFAOYSA-N 0.000 description 2
QZUJVRFMFGQENA-UHFFFAOYSA-N 9-chloro-2-(furan-2-yl)-5-methylsulfanyl-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N=1N2C(SC)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 QZUJVRFMFGQENA-UHFFFAOYSA-N 0.000 description 2
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 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
PLMWDZWWSBWCGW-UHFFFAOYSA-N N=1N2C(S)=NC3=CC=CC=C3C2=NC=1C1=CC=CO1 Chemical compound N=1N2C(S)=NC3=CC=CC=C3C2=NC=1C1=CC=CO1 PLMWDZWWSBWCGW-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000005708 Sodium hypochlorite Substances 0.000 description 2
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
ZBIAFNABYZOHCJ-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]quinazoline Chemical compound C12=CC=CC=C2N=CN2C1=NC=N2 ZBIAFNABYZOHCJ-UHFFFAOYSA-N 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 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
125000004432 carbon atom Chemical group C* 0.000 description 2
NYQXVKFKGJZIOC-UHFFFAOYSA-N chembl329502 Chemical compound FC1=CC=CC=C1C1=NN2C(=O)NC3=CC=C(Cl)C=C3C2=N1 NYQXVKFKGJZIOC-UHFFFAOYSA-N 0.000 description 2
ZVJKSWIXUYGBQO-UHFFFAOYSA-N chembl329504 Chemical compound C1=CC(Cl)=CC=C1C1=NN2C(=O)NC3=CC=CC=C3C2=N1 ZVJKSWIXUYGBQO-UHFFFAOYSA-N 0.000 description 2
YYDZNOUMWKJXMG-UHFFFAOYSA-N chloro(phenyl)phosphane Chemical compound ClPC1=CC=CC=C1 YYDZNOUMWKJXMG-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
239000008187 granular material Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
CASBPSROMSMGJE-UHFFFAOYSA-N n-methylpiperidine-2-carbohydrazide Chemical compound CN(N)C(=O)C1CCCCN1 CASBPSROMSMGJE-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
238000000746 purification Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
FQIAWPZQJCAPSW-UHFFFAOYSA-N 1h-pyrrole-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CN1 FQIAWPZQJCAPSW-UHFFFAOYSA-N 0.000 description 1
AUUVWPPAZWJXGE-UHFFFAOYSA-N 2,4-dichloro-6-(3-phenyl-1h-1,2,4-triazol-5-yl)aniline Chemical compound NC1=C(Cl)C=C(Cl)C=C1C1=NNC(C=2C=CC=CC=2)=N1 AUUVWPPAZWJXGE-UHFFFAOYSA-N 0.000 description 1
DUDRAKXAVJKRHA-UHFFFAOYSA-N 2,4-disulfido-1,3,2,4-dithiadiphosphetane-2,4-diium Chemical compound S=P1SP(=S)S1 DUDRAKXAVJKRHA-UHFFFAOYSA-N 0.000 description 1
IWNHTCBFRSCBQK-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanol Chemical compound OCCC1=CC=CC=C1Cl IWNHTCBFRSCBQK-UHFFFAOYSA-N 0.000 description 1
HYEMXWLUMWMIQU-UHFFFAOYSA-N 2-(2-fluorophenyl)-9-nitro-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Chemical compound N1=C2C3=CC([N+](=O)[O-])=CC=C3NC(=O)N2N=C1C1=CC=CC=C1F HYEMXWLUMWMIQU-UHFFFAOYSA-N 0.000 description 1
SBRCVHBLAZOQNB-UHFFFAOYSA-N 2-(3-phenyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=NNC(C=2C=CC=CC=2)=N1 SBRCVHBLAZOQNB-UHFFFAOYSA-N 0.000 description 1
QNLUDZFCJHWJBU-UHFFFAOYSA-N 2-(3-pyridin-3-yl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=NNC(C=2C=NC=CC=2)=N1 QNLUDZFCJHWJBU-UHFFFAOYSA-N 0.000 description 1
YMKDZEDXFIXGNK-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-(2-iodophenyl)propanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NC(C(=O)O)CC1=CC=CC=C1I YMKDZEDXFIXGNK-UHFFFAOYSA-N 0.000 description 1
ANOCUVGOAQCHOV-UHFFFAOYSA-N 2-(furan-2-yl)-6-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-imine;methanesulfonic acid Chemical compound CS(O)(=O)=O.N=1N2C(=N)N(C)C3=CC=CC=C3C2=NC=1C1=CC=CO1 ANOCUVGOAQCHOV-UHFFFAOYSA-N 0.000 description 1
HAFXJDONHISOCP-UHFFFAOYSA-N 2-(furan-2-yl)-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Chemical compound N=1N2C(=O)NC3=CC=CC=C3C2=NC=1C1=CC=CO1 HAFXJDONHISOCP-UHFFFAOYSA-N 0.000 description 1
WTQTWLIUVOLCCQ-UHFFFAOYSA-N 2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC3=CC=CC=C3C2=NC=1C1=CC=CO1 WTQTWLIUVOLCCQ-UHFFFAOYSA-N 0.000 description 1
UCHXUKWQWGPOFL-UHFFFAOYSA-N 2-(furan-2-yl)-n-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(=NC)NC3=CC=CC=C3C2=NC=1C1=CC=CO1 UCHXUKWQWGPOFL-UHFFFAOYSA-N 0.000 description 1
QODRFAYDFCMGQK-UHFFFAOYSA-N 2-(methylamino)benzohydrazide Chemical compound CNC1=CC=CC=C1C(=O)NN QODRFAYDFCMGQK-UHFFFAOYSA-N 0.000 description 1
AXRHHLWRTQOJLN-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1h-1,2,4-triazol-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=NNC(C=2C=CC(Cl)=CC=2)=N1 AXRHHLWRTQOJLN-UHFFFAOYSA-N 0.000 description 1
HQXYGMCUJXWRFN-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1h-1,2,4-triazol-5-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1C1=NNC(C=2C(=CC=CC=2)C#N)=N1 HQXYGMCUJXWRFN-UHFFFAOYSA-N 0.000 description 1
NDMGUUWNHBBFSZ-UHFFFAOYSA-N 2-[5-(furan-2-yl)-1h-1,2,4-triazol-3-yl]-n-methylaniline Chemical compound CNC1=CC=CC=C1C1=NNC(C=2OC=CC=2)=N1 NDMGUUWNHBBFSZ-UHFFFAOYSA-N 0.000 description 1
WHJVJQUJYOIRNW-UHFFFAOYSA-N 2-[[9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl]amino]ethanol Chemical compound N=1N2C(NCCO)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 WHJVJQUJYOIRNW-UHFFFAOYSA-N 0.000 description 1
YVSLPKPNHFWHSX-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzohydrazide Chemical compound NNC(=O)C1=CC(Cl)=CC(Cl)=C1N YVSLPKPNHFWHSX-UHFFFAOYSA-N 0.000 description 1
NQQKJMGWDPRSMT-UHFFFAOYSA-N 2-amino-n-[[amino(pyridin-4-yl)methylidene]amino]benzamide Chemical compound NC1=CC=CC=C1C(=O)NNC(=N)C1=CC=NC=C1 NQQKJMGWDPRSMT-UHFFFAOYSA-N 0.000 description 1
GRWMSCBKWMQPON-UHFFFAOYSA-N 2-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1N GRWMSCBKWMQPON-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 1
UODCTVIFRDBTOF-UHFFFAOYSA-N 2-methoxyethanol;hydrate Chemical compound O.COCCO UODCTVIFRDBTOF-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
SGTXILTYXULEQD-UHFFFAOYSA-N 2H-triazolo[4,5-f]phthalazine Chemical compound N1=NC=C2C3=NNN=C3C=CC2=C1 SGTXILTYXULEQD-UHFFFAOYSA-N 0.000 description 1
KCQZWVHRHGDYRT-UHFFFAOYSA-N 3-(4-chloro-2-cyanophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1C#N KCQZWVHRHGDYRT-UHFFFAOYSA-N 0.000 description 1
ZLJNICWEXVCBKL-UHFFFAOYSA-N 3-(4-chlorophenyl)-[1,2,4]triazolo[3,4-a]phthalazine Chemical compound C1=CC(Cl)=CC=C1C1=NN=C2N1N=CC1=CC=CC=C12 ZLJNICWEXVCBKL-UHFFFAOYSA-N 0.000 description 1
PHRDZSRVSVNQRN-UHFFFAOYSA-N 3-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC(Cl)=C1 PHRDZSRVSVNQRN-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
GINLWLVGYWBOOP-UHFFFAOYSA-N 3-pyridin-3-yl-[1,2,4]triazolo[3,4-a]phthalazine Chemical compound N12N=CC3=CC=CC=C3C2=NN=C1C1=CC=CN=C1 GINLWLVGYWBOOP-UHFFFAOYSA-N 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
HVDNECJRVKOPKV-UHFFFAOYSA-N 4-chloro-2-(3-phenyl-1h-1,2,4-triazol-5-yl)aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C=2C=CC=CC=2)=N1 HVDNECJRVKOPKV-UHFFFAOYSA-N 0.000 description 1
HRHTXVKAXFMKOR-UHFFFAOYSA-N 4-chloro-2-(3-pyridin-2-yl-1,2-dihydro-1,2,4-triazol-3-yl)aniline Chemical compound NC1=CC=C(Cl)C=C1C1(C=2N=CC=CC=2)N=CNN1 HRHTXVKAXFMKOR-UHFFFAOYSA-N 0.000 description 1
AOGUKZHIPJICMC-UHFFFAOYSA-N 4-chloro-2-(5-pyridin-2-yl-1h-1,2,4-triazol-3-yl)aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C=2N=CC=CC=2)=N1 AOGUKZHIPJICMC-UHFFFAOYSA-N 0.000 description 1
WNYBHJUZZNWVBC-UHFFFAOYSA-N 4-chloro-2-[3-(furan-3-yl)-1h-1,2,4-triazol-5-yl]aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C2=COC=C2)=N1 WNYBHJUZZNWVBC-UHFFFAOYSA-N 0.000 description 1
QJIDHSRYINTNFI-UHFFFAOYSA-N 4-chloro-2-[5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NN=C(C=2C(=CC=CC=2)F)O1 QJIDHSRYINTNFI-UHFFFAOYSA-N 0.000 description 1
AXLRJXIJGJFSSP-UHFFFAOYSA-N 4-chloro-2-[5-(2-fluorophenyl)-1h-1,2,4-triazol-3-yl]aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NNC(C=2C(=CC=CC=2)F)=N1 AXLRJXIJGJFSSP-UHFFFAOYSA-N 0.000 description 1
QLNOAPPALUOHMD-UHFFFAOYSA-N 4-chloro-2-isothiocyanatobenzonitrile Chemical compound ClC1=CC=C(C#N)C(N=C=S)=C1 QLNOAPPALUOHMD-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
ZMZGIVVRBMFZSG-UHFFFAOYSA-N 4-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C=C1 ZMZGIVVRBMFZSG-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
YWQFREQIXMZYEP-UHFFFAOYSA-N 4-methylbenzenesulfonic acid 2-pyridin-3-yl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.N1=CC(=CC=C1)C1=NN2C(NC=3C=CC=CC3C2=N1)=O YWQFREQIXMZYEP-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
XCKDILPIYXHOQN-UHFFFAOYSA-N 5,9-dichloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N1=C2C3=CC(Cl)=CC=C3N=C(Cl)N2N=C1C1=CC=CO1 XCKDILPIYXHOQN-UHFFFAOYSA-N 0.000 description 1
GTHSFZHYNMITKZ-UHFFFAOYSA-N 5,9-dichloro-2-(oxolan-2-yl)-[1,2,4]triazolo[1,5-c]quinazoline Chemical compound N1=C2C3=CC(Cl)=CC=C3N=C(Cl)N2N=C1C1CCCO1 GTHSFZHYNMITKZ-UHFFFAOYSA-N 0.000 description 1
AKANWSCBFOMJNS-UHFFFAOYSA-N 5-bromofuran-2-carbohydrazide Chemical compound NNC(=O)C1=CC=C(Br)O1 AKANWSCBFOMJNS-UHFFFAOYSA-N 0.000 description 1
LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
VQZRVPWIZFFSQD-UHFFFAOYSA-N 6h-quinazolin-5-one Chemical compound C1=NC=C2C(=O)CC=CC2=N1 VQZRVPWIZFFSQD-UHFFFAOYSA-N 0.000 description 1
COQOWPZNCVPUER-UHFFFAOYSA-N 9-chloro-2-(3-chlorophenyl)-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Chemical compound ClC1=CC=CC(C2=NN3C(=O)NC4=CC=C(Cl)C=C4C3=N2)=C1 COQOWPZNCVPUER-UHFFFAOYSA-N 0.000 description 1
VCXJUUAJJHBHKG-UHFFFAOYSA-N 9-chloro-2-(furan-2-yl)-n-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(NC)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 VCXJUUAJJHBHKG-UHFFFAOYSA-N 0.000 description 1
XKQKDMLQVSGDIN-UHFFFAOYSA-N 9-chloro-2-(furan-2-yl)-n-propan-2-yl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(NC(C)C)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CO1 XKQKDMLQVSGDIN-UHFFFAOYSA-N 0.000 description 1
MQNCTZYKXLETQP-UHFFFAOYSA-N 9-chloro-2-(furan-3-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=N)N2N=C1C=1C=COC=1 MQNCTZYKXLETQP-UHFFFAOYSA-N 0.000 description 1
BVFLWFQFKAPQFY-UHFFFAOYSA-N 9-chloro-2-(oxolan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=N)N2N=C1C1CCCO1 BVFLWFQFKAPQFY-UHFFFAOYSA-N 0.000 description 1
XSTFTZCBWDZMKH-UHFFFAOYSA-N 9-chloro-2-pyridin-2-yl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine methanesulfonic acid Chemical compound CS(O)(=O)=O.N=1N2C(N)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=CC=N1 XSTFTZCBWDZMKH-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 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
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
238000006105 Hofmann reaction Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
DJFAQJHRDNUZKH-UHFFFAOYSA-N N'-amino-1-(2-amino-5-chlorobenzoyl)-2H-pyridine-2-carboximidamide Chemical compound NNC(=N)C1C=CC=CN1C(=O)C1=CC(Cl)=CC=C1N DJFAQJHRDNUZKH-UHFFFAOYSA-N 0.000 description 1
YBOZAXFRLLWBFF-UHFFFAOYSA-N N-methyl-2-(1H-pyrrol-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(=NC)NC3=CC=CC=C3C2=NC=1C1=CC=CN1 YBOZAXFRLLWBFF-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
ACWRHBDMPYWYDK-UHFFFAOYSA-N N=1N2C(=S)NC3=CC=CC=C3C2=NC=1C1=CC=CN1 Chemical compound N=1N2C(=S)NC3=CC=CC=C3C2=NC=1C1=CC=CN1 ACWRHBDMPYWYDK-UHFFFAOYSA-N 0.000 description 1
FJAIOTHJFYXXEI-UHFFFAOYSA-N N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=C(Br)O1 Chemical compound N=1N2C(S)=NC3=CC=C(Cl)C=C3C2=NC=1C1=CC=C(Br)O1 FJAIOTHJFYXXEI-UHFFFAOYSA-N 0.000 description 1
SLMYUKRDBHQNEF-UHFFFAOYSA-N N=1N2C(S)=NC3=CC=CC=C3C2=NC=1C=1C=COC=1 Chemical compound N=1N2C(S)=NC3=CC=CC=C3C2=NC=1C=1C=COC=1 SLMYUKRDBHQNEF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 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
229920001615 Tragacanth Polymers 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
RUROFEVDCUGKHD-QPJJXVBHSA-N [(e)-3-bromoprop-1-enyl]benzene Chemical compound BrC\C=C\C1=CC=CC=C1 RUROFEVDCUGKHD-QPJJXVBHSA-N 0.000 description 1
ATSBOHGDBMFDQC-UHFFFAOYSA-N [2-(5-bromofuran-2-yl)-9-chloro-[1,2,4]triazolo[1,5-c]quinazolin-5-yl] thiocyanate Chemical compound N1=C2C3=CC(Cl)=CC=C3N=C(SC#N)N2N=C1C1=CC=C(Br)O1 ATSBOHGDBMFDQC-UHFFFAOYSA-N 0.000 description 1
NEJATMAGGJCOSP-UHFFFAOYSA-N [9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl] thiocyanate Chemical compound N1=C2C3=CC(Cl)=CC=C3N=C(SC#N)N2N=C1C1=CC=CO1 NEJATMAGGJCOSP-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
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 1
229940081735 acetylcellulose Drugs 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
239000005456 alcohol based solvent 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
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
125000005427 anthranyl group Chemical group 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Natural products OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000000872 buffer Substances 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
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
GBYVBYNWLQCWMU-UHFFFAOYSA-N chembl100101 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C=1C=COC=1 GBYVBYNWLQCWMU-UHFFFAOYSA-N 0.000 description 1
MZVWOOJKIFXNDI-UHFFFAOYSA-N chembl317375 Chemical compound N=1N2C(=O)NC3=CC=CC=C3C2=NC=1C1=CC=CN=C1 MZVWOOJKIFXNDI-UHFFFAOYSA-N 0.000 description 1
MAKPSBBZLHQMKS-UHFFFAOYSA-N chembl318199 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1=CC=CC=C1 MAKPSBBZLHQMKS-UHFFFAOYSA-N 0.000 description 1
OGZOTYWWPNCPEE-UHFFFAOYSA-N chembl318552 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1=CC=CN=C1 OGZOTYWWPNCPEE-UHFFFAOYSA-N 0.000 description 1
YIMMEIRULOZLFI-UHFFFAOYSA-N chembl329300 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1=CC=CC=N1 YIMMEIRULOZLFI-UHFFFAOYSA-N 0.000 description 1
LHOMBPYUYAHXIV-UHFFFAOYSA-N chembl330209 Chemical compound N1=C2C3=CC(Cl)=CC(Cl)=C3NC(=O)N2N=C1C1=CC=CC=C1 LHOMBPYUYAHXIV-UHFFFAOYSA-N 0.000 description 1
FQNUUSRLNIBTES-UHFFFAOYSA-N chembl420457 Chemical compound N1=C2C3=CC(Cl)=CC=C3NC(=O)N2N=C1C1CCCO1 FQNUUSRLNIBTES-UHFFFAOYSA-N 0.000 description 1
FQPNNOSGYJAGAX-UHFFFAOYSA-N chembl430494 Chemical compound FC1=CC=CC=C1C1=NN2C(=O)NC3=CC=CC=C3C2=N1 FQPNNOSGYJAGAX-UHFFFAOYSA-N 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
FBHBPOILPLAOMZ-UHFFFAOYSA-N chlorobenzene;cyclohexane Chemical compound C1CCCCC1.ClC1=CC=CC=C1 FBHBPOILPLAOMZ-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
230000003930 cognitive ability Effects 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 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
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
238000000354 decomposition reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
RJPYCQIROWUTHA-UHFFFAOYSA-N ethyl n-(2-cyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC=C1C#N RJPYCQIROWUTHA-UHFFFAOYSA-N 0.000 description 1
XCMLPBNNBDPVDU-UHFFFAOYSA-N ethyl n-(4-chloro-2-cyanophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1C#N XCMLPBNNBDPVDU-UHFFFAOYSA-N 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
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000006870 function Effects 0.000 description 1
TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 1
FDKYTUTUYYBJDC-UHFFFAOYSA-N furan-3-carbohydrazide Chemical compound NNC(=O)C=1C=COC=1 FDKYTUTUYYBJDC-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
ZUXNZUWOTSUBMN-UHFFFAOYSA-N hydralazine hydrochloride Chemical compound Cl.C1=CC=C2C(NN)=NN=CC2=C1 ZUXNZUWOTSUBMN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000012907 medicinal substance Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
WUKQWYDGYGGOMJ-UHFFFAOYSA-N methanol;2-methoxyethanol Chemical compound OC.COCCO WUKQWYDGYGGOMJ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
FGDYAAXXBPMZDU-UHFFFAOYSA-N n,n-dimethylacetamide;ethanol Chemical compound CCO.CN(C)C(C)=O FGDYAAXXBPMZDU-UHFFFAOYSA-N 0.000 description 1
RAYLUPYCGGKXQO-UHFFFAOYSA-N n,n-dimethylacetamide;hydrate Chemical compound O.CN(C)C(C)=O RAYLUPYCGGKXQO-UHFFFAOYSA-N 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
OPHDQDXGXHXWON-UHFFFAOYSA-N n-ethyl-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(=NCC)NC3=CC=CC=C3C2=NC=1C1=CC=CO1 OPHDQDXGXHXWON-UHFFFAOYSA-N 0.000 description 1
KAEYIUQFNVTXGK-UHFFFAOYSA-N n-methyl-1h-pyrrole-2-carbohydrazide Chemical compound CN(N)C(=O)C1=CC=CN1 KAEYIUQFNVTXGK-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 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
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
IUJBLZNOFNHTEQ-UHFFFAOYSA-N o-ethyl n-(2-cyanophenyl)carbamothioate Chemical compound CCOC(=S)NC1=CC=CC=C1C#N IUJBLZNOFNHTEQ-UHFFFAOYSA-N 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000005968 oxazolinyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
LLGRORFWHFVNIK-UHFFFAOYSA-N oxolane-2-carbohydrazide Chemical compound NNC(=O)C1CCCO1 LLGRORFWHFVNIK-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012713 reactive precursor Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
RYXNTTXRPACDJA-UHFFFAOYSA-N sulfanyl carbonochloridate Chemical compound SOC(Cl)=O RYXNTTXRPACDJA-UHFFFAOYSA-N 0.000 description 1
GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical class S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 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
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000005881 triazolinyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO853859A 1984-10-01 1985-09-30 Triazolikinazolin-forbindelser. NO853859L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US65583184A	1984-10-01	1984-10-01

Publications (1)

Publication Number	Publication Date
NO853859L true NO853859L (no)	1986-04-02

Family

ID=24630556

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO853859A NO853859L (no)	1984-10-01	1985-09-30	Triazolikinazolin-forbindelser.

Country Status (13)

Country	Link
EP (1)	EP0181282A1 (fi)
JP (1)	JPS61165386A (fi)
AU (1)	AU4813285A (fi)
DD (1)	DD236931A5 (fi)
DK (1)	DK442385A (fi)
ES (4)	ES8801277A1 (fi)
FI (1)	FI853736L (fi)
GR (1)	GR852343B (fi)
HU (1)	HU194566B (fi)
IL (1)	IL76528A0 (fi)
NO (1)	NO853859L (fi)
PT (1)	PT81225B (fi)
ZA (1)	ZA857529B (fi)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3677445D1 (de) *	1985-09-30	1991-03-14	Ciba Geigy Ag	2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung.
US4831013A (en) *	1986-03-20	1989-05-16	Ciba-Geigy Corporation	2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof
EP0263071B1 (en) *	1986-09-30	1992-08-12	Ciba-Geigy Ag	2-Substituted-e-fused-[1,2,4]-triazolo[1,5-c] pyrimidines, pharmaceutical compositions, and uses thereof
HU198484B (en) *	1986-11-05	1989-10-30	Egyt Gyogyszervegyeszeti Gyar	Process for producing new condensed cyclic triazolo/1,5-a/pyrimidine derivatives
US4780464A (en) *	1986-12-08	1988-10-25	Warner-Lambert Company	(1,2,4)triazolo(4,3-a)quinoxaline-4-amines
CA1331178C (en) *	1988-02-05	1994-08-02	James J. Wade	Triazolo ¬1,5-c\| pyrimido ¬1,4\| azines as bronchodilators
US5338743A (en) *	1988-06-06	1994-08-16	Fujisawa Pharmaceutical Co., Ltd.	New use of the adenosine antagonist
US5095015A (en) *	1990-07-24	1992-03-10	Neurogen Corporation	Certain azacycloalkyl imidazopyrimidines; a new class of gaba brain receptor ligands
US5185446A (en) *	1990-09-04	1993-02-09	Neurogen Corporation	Certain cycloalkyl imidazopyrimidines; a new class of gaba brainreceptor ligands
US5744602A (en) *	1990-10-31	1998-04-28	Neurogen Corporation	Certain imidazoquinoxalines; a new class of GABA brain receptor ligands
US5130430A (en) *	1990-10-31	1992-07-14	Neurogen Corporation	2-substituted imidazoquinoxaline diones, a new class of gaba brain receptor ligands
US5182386A (en) *	1991-08-27	1993-01-26	Neurogen Corporation	Certain imidazoquinoxalinones; a new class of gaba brain receptor ligands
US5182290A (en) *	1991-08-27	1993-01-26	Neurogen Corporation	Certain oxazoloquinolinones; a new class of GABA brain receptor ligands
US5243049A (en) *	1992-01-22	1993-09-07	Neurogen Corporation	Certain pyrroloquinolinones: a new class of GABA brain receptor ligands
US5266698A (en) *	1992-04-30	1993-11-30	Neurogen Corporation	Certain aryl and cycloalkyl fused imidazopyrazinediones; a new class of GABA brain receptor ligands
US5306819A (en) *	1992-08-27	1994-04-26	Neurogen Corporation	Certain aryl a cycloalkyl fused imidazopyrazinols; and new class of GABA brain receptor ligands
DE4241564A1 (de) *	1992-12-10	1994-06-16	Basf Ag	Triazolochinazoline zur Behandlung zentralnervöser Erkrankungen
US5565460A (en) *	1993-07-27	1996-10-15	Kyowa Hakko Koygo Co., Ltd.	Therapeutic purine agents for parkinson's disease
US5792766A (en)	1996-03-13	1998-08-11	Neurogen Corporation	Imidazo 1,5-c! quinazolines; a new class of GABA brain receptor ligands
US5955465A (en) *	1996-03-22	1999-09-21	Neurogen Corporation	1,2,4-triazolo 4,3-c!quinazolin-3-ones and 1,2,4-triazolo 4,3-c!quinazolin-3-thiones
US5677309A (en) *	1996-03-22	1997-10-14	Neurogen Corporation	1,2,4-triazolo 4,3-c! quinazolin-3-ones and 1,2,4-triazolo 4,3-c!quinazolin-3-thiones; a new class of GABA brain receptor ligands
ES2200566T3 (es) *	1998-10-23	2004-03-01	Dow Agrosciences Llc	3-(piridilo sustituido)-1,2,4-triazoles insecticidas.
DK2861603T3 (en)	2012-06-18	2019-03-04	Dart Neuroscience Cayman Ltd	6-benzyl-6H-pyrido [3,2-e] [1,2,4] triazolo [1,5-c] pyrimidin-5-one and 6-benzyl- [1,2,4] triazolo [1, 5-c] pteridine-5 (6H) -one derivatives as PDE1 inhibitors for the treatment of, e.g., neurological disorders
WO2014101113A1 (en) *	2012-12-28	2014-07-03	Merck Sharp & Dohme Corp.	Piperazine-substituted 7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties
WO2014101120A1 (en) *	2012-12-28	2014-07-03	Merck Sharp & Dohme Corp.	Heterobicyclo-substituted-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties
WO2017008205A1 (en) *	2015-07-10	2017-01-19	Merck Sharp & Dohme Corp.	Substituted aminoquinazoline compounds as a2a antagonist
JP6420400B2 (ja) *	2017-04-12	2018-11-07	ダート・ニューロサイエンス・（ケイマン）・リミテッド	置換ピリジンアゾロピリミジン−５−（６ｈ）−オン化合物
GB2575490A (en) *	2018-07-12	2020-01-15	Recordati Ind Chimica E Farmaceutica Spa	P2X3 receptor antagonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4252945A (en) *	1979-07-11	1981-02-24	E. R. Squibb & Sons, Inc.	Process for preparing pyrazolo[1,5-c]-quinazoline derivatives and novel intermediates
DE3146599A1 (de) *	1981-11-25	1983-07-07	Basf Ag, 6700 Ludwigshafen	Neue triazolochinazoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen

1985
- 1985-09-25 EP EP85810438A patent/EP0181282A1/de active Pending
- 1985-09-26 GR GR852343A patent/GR852343B/el unknown
- 1985-09-27 FI FI853736A patent/FI853736L/fi not_active Application Discontinuation
- 1985-09-27 IL IL76528A patent/IL76528A0/xx unknown
- 1985-09-27 HU HU853741A patent/HU194566B/hu unknown
- 1985-09-30 DK DK442385A patent/DK442385A/da not_active Application Discontinuation
- 1985-09-30 PT PT81225A patent/PT81225B/pt unknown
- 1985-09-30 DD DD85281220A patent/DD236931A5/de unknown
- 1985-09-30 AU AU48132/85A patent/AU4813285A/en not_active Abandoned
- 1985-09-30 NO NO853859A patent/NO853859L/no unknown
- 1985-09-30 ZA ZA857529A patent/ZA857529B/xx unknown
- 1985-10-01 JP JP60216280A patent/JPS61165386A/ja active Pending
1986
- 1986-10-01 ES ES557118A patent/ES8801277A1/es not_active Expired
- 1986-10-01 ES ES557120A patent/ES8802387A1/es not_active Expired
- 1986-10-01 ES ES557119A patent/ES8802386A1/es not_active Expired
- 1986-10-01 ES ES557117A patent/ES8707732A1/es not_active Expired

Also Published As

Publication number	Publication date
ES557118A0 (es)	1988-01-01
AU4813285A (en)	1986-04-10
IL76528A0 (en)	1986-01-31
DD236931A5 (de)	1986-06-25
PT81225A (en)	1985-10-01
ES557117A0 (es)	1987-08-16
EP0181282A1 (de)	1986-05-14
HUT38941A (en)	1986-07-28
FI853736L (fi)	1986-04-02
ES8802387A1 (es)	1988-05-16
ES8707732A1 (es)	1987-08-16
DK442385A (da)	1986-04-02
ZA857529B (en)	1986-05-28
ES8801277A1 (es)	1988-01-01
DK442385D0 (da)	1985-09-30
GR852343B (fi)	1986-01-28
HU194566B (en)	1988-02-29
JPS61165386A (ja)	1986-07-26
ES8802386A1 (es)	1988-05-16
PT81225B (en)	1987-07-15
ES557119A0 (es)	1988-05-16
FI853736A0 (fi)	1985-09-27
ES557120A0 (es)	1988-05-16

Publication	Publication Date	Title
NO853859L (no)	1986-04-02	Triazolikinazolin-forbindelser.
US4713383A (en)	1987-12-15	Triazoloquinazoline compounds, and their methods of preparation, pharmaceutical compositions, and uses
EP1507780B1 (en)	2012-08-22	Pyrazolo-pyrimidine aniline compounds useful as kinase inhibitors
CN101952294B (zh)	2014-11-26	吡咯并吡嗪激酶抑制剂
RU2229299C2 (ru)	2004-05-27	Применение диазепинов для приготовления лекарственных средств, предназначенных для лечения патологических состояний или заболеваний, связанных с действием одного из рецепторов соматостатина
AU2004235907B2 (en)	2007-08-30	Fused pyrimidine derivatives with CRF activity
CA2288910C (en)	2003-06-24	Pyrazolopyrimidinones for sexual dysfunction
US7741332B2 (en)	2010-06-22	Fused ring heterocycles as potassium channel modulators
CA1288097C (en)	1991-08-27	2-substituted-e-fused-¬1,2,4\|triazolo-¬1,5- c\|pyrimidines pharmaceutical compositions and uses thereof
WO1988002370A1 (en)	1988-04-07	2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines pharmaceutical compositions and uses thereof
US20050143398A1 (en)	2005-06-30	Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors
US20080269238A1 (en)	2008-10-30	Thiazolopyrimidine Derivative
AU2005321946A1 (en)	2006-07-06	Enzyme modulators and treatments
SK281077B6 (sk)	2000-11-07	Heterocyklické zlúčeniny, spôsob ich prípravy, farmaceutický prostriedok a použitie
AU2012296529A1 (en)	2014-02-20	Heteroaryl sodium channel inhibitors
BR122017002951A2 (pt)	2020-01-28	amidas heterocíclicas como inibidores de quinases
EP2083816A2 (en)	2009-08-05	Heterocyclic amide compounds useful as kinase inhibitors
EP4117784B1 (en)	2024-08-28	Gpr52 modulator compounds
CA3122623A1 (en)	2020-07-16	Halo-allylamine compounds and use thereof
JP5324785B2 (ja)	2013-10-23	複素環アミド化合物及びその用途
AU689468B2 (en)	1998-04-02	Imidazopyridine
US4831013A (en)	1989-05-16	2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof
JPS63258881A (ja)	1988-10-26	３Ｈ―１，２，３―トリアゾロ〔４，５―ｄ〕ピリミジン
WO2001044250A1 (en)	2001-06-21	SUBSTITUTED 1,2,3-TRIAZOLO[1,5-a]QUINAZOLINES FOR ENHANCING COGNITION
JPS62135475A (ja)	1987-06-18	２−置換−ｅ−融合−〔１，２，４〕トリアゾロ−〔１，５−Ｃ〕ピリミジン