HRP20100272T2 - Piridinaminosulfonil supstituirani benzamidi kao inhibitori citokroma p450 3a4 (cyp3a4) - Google Patents
Piridinaminosulfonil supstituirani benzamidi kao inhibitori citokroma p450 3a4 (cyp3a4) Download PDFInfo
- Publication number
- HRP20100272T2 HRP20100272T2 HR20100272T HRP20100272T HRP20100272T2 HR P20100272 T2 HRP20100272 T2 HR P20100272T2 HR 20100272 T HR20100272 T HR 20100272T HR P20100272 T HRP20100272 T HR P20100272T HR P20100272 T2 HRP20100272 T2 HR P20100272T2
- Authority
- HR
- Croatia
- Prior art keywords
- cr12ar12b
- alkyl
- hydrogen
- amino
- sulfonyl
- Prior art date
Links
- 102000004328 Cytochrome P-450 CYP3A Human genes 0.000 title 2
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 title 2
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 150000003936 benzamides Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 27
- 239000001257 hydrogen Substances 0.000 claims abstract 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 13
- 125000006694 (C2-C10) heterocyclyl group Chemical group 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 12
- 239000012453 solvate Substances 0.000 claims abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 125000004429 atom Chemical group 0.000 claims abstract 3
- -1 C 1 -C 6 alkyl Inorganic materials 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 150000002431 hydrogen Chemical group 0.000 claims 8
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims 6
- 108010019625 Atazanavir Sulfate Proteins 0.000 claims 5
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims 5
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims 5
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 claims 5
- HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 claims 4
- BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 claims 4
- AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims 3
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 3
- SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 claims 3
- 229960001830 amprenavir Drugs 0.000 claims 3
- 230000036436 anti-hiv Effects 0.000 claims 3
- 229960003277 atazanavir Drugs 0.000 claims 3
- 229950009079 brecanavir Drugs 0.000 claims 3
- JORVRJNILJXMMG-OLNQLETPSA-N brecanavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2OCOC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C(C=C1)=CC=C1OCC1=CSC(C)=N1 JORVRJNILJXMMG-OLNQLETPSA-N 0.000 claims 3
- PMDQGYMGQKTCSX-HQROKSDRSA-L calcium;[(2r,3s)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3s)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphate Chemical compound [Ca+2].C([C@@H]([C@H](OP([O-])([O-])=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 PMDQGYMGQKTCSX-HQROKSDRSA-L 0.000 claims 3
- 229960005107 darunavir Drugs 0.000 claims 3
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims 3
- 229960002933 fosamprenavir calcium Drugs 0.000 claims 3
- 229960001936 indinavir Drugs 0.000 claims 3
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims 3
- 229940088976 invirase Drugs 0.000 claims 3
- 229960004525 lopinavir Drugs 0.000 claims 3
- 229960000884 nelfinavir Drugs 0.000 claims 3
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims 3
- 229950006460 palinavir Drugs 0.000 claims 3
- RXBWRFDZXRAEJT-SZNOJMITSA-N palinavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)[C@H](O)CN1[C@@H](C[C@@H](CC1)OCC=1C=CN=CC=1)C(=O)NC(C)(C)C)C1=CC=CC=C1 RXBWRFDZXRAEJT-SZNOJMITSA-N 0.000 claims 3
- 229960000311 ritonavir Drugs 0.000 claims 3
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims 3
- 229960001852 saquinavir Drugs 0.000 claims 3
- 229960000838 tipranavir Drugs 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- IXZYCIFRVZKVRJ-RKKDRKJOSA-N (2s)-n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-[[2-[(3-fluorophenyl)methylamino]acetyl]amino]-3,3-dimethylbutanamide Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)[C@@H](NC(=O)CNCC=1C=C(F)C=CC=1)C(C)(C)C)C1=CC=CC=C1 IXZYCIFRVZKVRJ-RKKDRKJOSA-N 0.000 claims 2
- CUFQBQOBLVLKRF-RZDMPUFOSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 108010075606 kynostatin 272 Proteins 0.000 claims 2
- NYGRNTSORGSTJK-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[(4-ethoxypyridin-3-yl)sulfamoyl]-n-methylbenzamide Chemical compound CCOC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)N(C)CC1=CC=C(F)C(F)=C1 NYGRNTSORGSTJK-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- ZOCLBCDMJXZMHF-UHFFFAOYSA-N 2-[(4-ethoxypyridin-3-yl)sulfamoyl]-n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound CCOC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)NCC1=CC=C(F)C(C(F)(F)F)=C1 ZOCLBCDMJXZMHF-UHFFFAOYSA-N 0.000 claims 1
- HCKHZGMYCRMGNN-UHFFFAOYSA-N 2-[(5-ethoxypyridin-3-yl)sulfamoyl]-n-[2-(2-methylphenyl)ethyl]benzamide Chemical compound CCOC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCCC=2C(=CC=CC=2)C)=C1 HCKHZGMYCRMGNN-UHFFFAOYSA-N 0.000 claims 1
- CNXACKFWYRYUCW-UHFFFAOYSA-N 2-[(5-ethoxypyridin-3-yl)sulfamoyl]-n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound CCOC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(C(F)=CC=2)C(F)(F)F)=C1 CNXACKFWYRYUCW-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- RIEHXZKHLIMPRG-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-[(5-ethoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound CCOC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)=C1 RIEHXZKHLIMPRG-UHFFFAOYSA-N 0.000 claims 1
- ZWRFIJHLXJKXTN-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2-[(5-methylpyridin-3-yl)sulfamoyl]benzamide Chemical compound CC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)=C1 ZWRFIJHLXJKXTN-UHFFFAOYSA-N 0.000 claims 1
- WZPOEIYGBPZWFU-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[(4-ethoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound CCOC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)NCC1=CC=C(F)C(F)=C1 WZPOEIYGBPZWFU-UHFFFAOYSA-N 0.000 claims 1
- KVPBBXNZIREVEW-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[(4-methoxypyridin-3-yl)sulfamoyl]-n-methylbenzamide Chemical compound COC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)N(C)CC1=CC=C(F)C(F)=C1 KVPBBXNZIREVEW-UHFFFAOYSA-N 0.000 claims 1
- AIXZEHAFOAWCBI-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[(4-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)NCC1=CC=C(F)C(F)=C1 AIXZEHAFOAWCBI-UHFFFAOYSA-N 0.000 claims 1
- BKNCIMAPPAXVNR-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-[(5-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(F)C(F)=CC=2)=C1 BKNCIMAPPAXVNR-UHFFFAOYSA-N 0.000 claims 1
- QVOWRNNWQKOAJN-UHFFFAOYSA-N n-[(3,5-dichlorophenyl)methyl]-2-[(5-methylpyridin-3-yl)sulfamoyl]benzamide Chemical compound CC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(Cl)C=C(Cl)C=2)=C1 QVOWRNNWQKOAJN-UHFFFAOYSA-N 0.000 claims 1
- VKLFHKFXCIIWSR-UHFFFAOYSA-N n-[(3-chloro-2-methylphenyl)methyl]-2-[(5-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C(=C(Cl)C=CC=2)C)=C1 VKLFHKFXCIIWSR-UHFFFAOYSA-N 0.000 claims 1
- TXMAHYZRZXTSDE-UHFFFAOYSA-N n-[(4-chloro-2-methylphenyl)methyl]-2-[(5-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C(=CC(Cl)=CC=2)C)=C1 TXMAHYZRZXTSDE-UHFFFAOYSA-N 0.000 claims 1
- UCEXMYNDLQJYOM-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-2-[(5-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCCC=2C(=CC=CC=2)F)=C1 UCEXMYNDLQJYOM-UHFFFAOYSA-N 0.000 claims 1
- LFXBOBVVGLBSHE-UHFFFAOYSA-N n-[2-(2-methylphenyl)ethyl]-2-[(5-methylpyridin-3-yl)sulfamoyl]benzamide Chemical compound CC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCCC=2C(=CC=CC=2)C)=C1 LFXBOBVVGLBSHE-UHFFFAOYSA-N 0.000 claims 1
- CYFWKTRCWDFGNM-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-[(4-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CC=NC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)NCC1=CC=C(F)C(C(F)(F)F)=C1 CYFWKTRCWDFGNM-UHFFFAOYSA-N 0.000 claims 1
- YFHUJXZHIOMPFO-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-[(5-methoxypyridin-3-yl)sulfamoyl]benzamide Chemical compound COC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(C(F)=CC=2)C(F)(F)F)=C1 YFHUJXZHIOMPFO-UHFFFAOYSA-N 0.000 claims 1
- NKERIASEZLPHHZ-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-2-[(5-methylpyridin-3-yl)sulfamoyl]benzamide Chemical compound CC1=CN=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(=O)NCC=2C=C(C(F)=CC=2)C(F)(F)F)=C1 NKERIASEZLPHHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 102220475869 Keratin, type I cytoskeletal 10_R12A_mutation Human genes 0.000 abstract 2
- 101000596772 Homo sapiens Transcription factor 7-like 1 Proteins 0.000 abstract 1
- 101000666382 Homo sapiens Transcription factor E2-alpha Proteins 0.000 abstract 1
- 102100035097 Transcription factor 7-like 1 Human genes 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Abstract
Spoj formule (I) naznačen time što: R1, R2, R3, R4 su nezavisno izabrani od vodika, C1-C6 alkil, -(CR12aR12b)thalo, -(CR12aR12b)tCN, -(CR12aR12b)tOR12a, -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tCF3, i -(CR12aR12b)tC6-C10 aril; R5 je vodik ili C1-C6 alkil; R6, R7, R8 i R9 su nezavisno izabrani od vodika, C1-C6alkil, -(CR12aR12b)thalo, -(CR12aR12b)tCN, -(CR12aR12b)tCF3,-(CR12aR12b)tOR12a, -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tR12a, -(CR12aR12b)tC3-C11cikloalkil; -(CR12aR12b)tC6-C10 aril, -(CR12aR12b)tC2-C10 heterociklil, -(CR12aR12b)theteroaril, -O(CR12aR12b)tR12a, -O(CR12aR12b)tC3-C11cikloalkil, -O(CR12aR12b)tC6-C10aril, -O(CR12aR12b)tC2-C10 heterociklil, -O(CR12aR12b)theteroaril, -O(CR12aR12b)tR12a i -O(CR12aR12b)tN(R12aR12b), gdje je svaka od spomenutih C1-C6alkil, C3-C11cikloalkil, C6-C10 aril i C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R14.R10 i R11 su nezavisno izabrani od vodika, -(CR12aR12b)tC1-C6 alkil, -(CR12aR12b)tC3-C11 cikloalkil, -(CR12aR12b)tC6-C10 aril, -(CR12aR12b)tC2-C10 heterociklil i -(CR12aR12b)theteroaril, gdje je svaka od spomenutih C1-C6 alkil, C3-C11 cikloalkil, C8-C10 aril, C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R13; iliR10 i R11 , zajedno sa atomom za koji su vezani, grade C2-C10 heterociklil grupu, po izboru supstituiranu sa jednim ili više R13;SVAKI R12A I R12B JE NEZAVISNO ODABRAN OD VODIKA I C1-C6 ALKIL; ILI R12A I R12B , ZAJEDNO SA ATOMOM ZA KOJI SU VEZANI, GRADE C3-C11 CIKLOALKIL ILI C2-C10 HETEROCIKLIL GRUPU; SVAKI OD R13 JE NEZAVISNO ODABRAN OD C1-C6 ALKIL, HALOGEN, -(CR12AR12B)TCN, -(CR12AR12B)TCF3, -(CR12AR12B)TOCF3, -(CR12AR12B)TC3-C11 CIKLOALKIL, -(CR12AR12B)TC6-C10 ARIL, -(CR12AR12B)TC2-C10 HETEROCIKLIL, -(CR12AR12B)THETEROARIL, -O(CR12AR12B)TR12A, -O(CR12AR12B)TC6-C10 ARIL, -O(CR12AR12B)TC2-C10 HETEROCIKLIL, -O(CR12AR12B)THETEROARIL, -(CR12AR12B)TCO2(C1-C6 ALKIL), -(CR12AR12B)TN(R12AR12B), -(CR12AR12B)TC(O)NR12AR12B, -(CR12AR12B)TOR12A, -(CR12AR12B)TS(O)R12A I -(CR12AR12B)TS(O)2R12A, GDJE JE SVAKA OD SPOMENUTIH C1-C6 ALKIL, C3-C11 CIKLOALKIL, C6-C10 ARIL, C2-C10 HETEROCIKLIL, I HETEROARIL GRUPA PO IZBORU SUPSTITUIRANA S JEDNIM ILI VIŠE R14;SVAKI OD R14 JE NEZAVISNO IZABRAN OD C1-C6 ALKIL, HALOGEN, -CN, -CF3, I OR12A; ISVAKI T JE NEZAVISNO IZABRAN OD 0, 1, 2, 3, 4, 5, I 6; ILINJEGOVA FARMACEUTSKI PRIHVATLJIVA SOL ILI SOLVAT. Patent sadrži još 18 patentnih zahtjeva.
Claims (19)
1. Spoj formule (I)
[image]
naznačen time što:
R1, R2, R3, R4 su nezavisno izabrani od vodika, C1-C6 alkil, -(CR12aR12b)thalo, -(CR12aR12b)tCN, -(CR12aR12b)tOR12a, -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tCF3, i -(CR12aR12b)tC6-C10 aril;
R5 je vodik ili C1-C6 alkil;
R6, R7, R8 i R9 su nezavisno izabrani od vodika, C1-C6alkil, -(CR12aR12b)thalo, -(CR12aR12b)tCN, -(CR12aR12b)tCF3,-(CR12aR12b)tOR12a, -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tR12a, -(CR12aR12b)tC3-C11cikloalkil; -(CR12aR12b)tC6-C10 aril, -(CR12aR12b)tC2-C10 heterociklil, -(CR12aR12b)theteroaril, -O(CR12aR12b)tR12a, -O(CR12aR12b)tC3-C11cikloalkil, -O(CR12aR12b)tC6-C10aril, -O(CR12aR12b)tC2-C10 heterociklil, -O(CR12aR12b)theteroaril, -O(CR12aR12b)tR12a i -O(CR12aR12b)tN(R12aR12b), gdje je svaka od spomenutih C1-C6alkil, C3-C11cikloalkil, C6-C10 aril i C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R14.
R10 i R11 su nezavisno izabrani od vodika, -(CR12aR12b)tC1-C6 alkil, -(CR12aR12b)tC3-C11 cikloalkil, -(CR12aR12b)tC6-C10 aril, -(CR12aR12b)tC2-C10 heterociklil i -(CR12aR12b)theteroaril, gdje je svaka od spomenutih C1-C6 alkil, C3-C11 cikloalkil, C8-C10 aril, C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R13; ili
R10 i R11 , zajedno sa atomom za koji su vezani, grade C2-C10 heterociklil grupu, po izboru supstituiranu sa jednim ili više R13;
svaki R12a i R12b je nezavisno odabran od vodika i C1-C6 alkil; ili
R12a i R12b, zajedno sa atomom za koji su vezani, grade C3-C11 cikloalkil ili C2-C10 heterociklil grupu;
svaki od R13 je nezavisno odabran od C1-C6 alkil, halogen, -(CR12aR12b)tCN, -(CR12aR12b)tCF3, -(CR12aR12b)tOCF3, -(CR12aR12b)tC3-C11 cikloalkil, -(CR12aR12b)tC6-C10 aril, -(CR12aR12b)tC2-C10 heterociklil, -(CR12aR12b)theteroaril, -O(CR12aR12b)tR12a, -O(CR12aR12b)tC6-C10 aril, -O(CR12aR12b)tC2-C10 heterociklil, -O(CR12aR12b)theteroaril, -(CR12aR12b)tCO2(C1-C6 alkil), -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tC(O)NR12aR12b, -(CR12aR12b)tOR12a, -(CR12aR12b)tS(O)R12a i -(CR12aR12b)tS(O)2R12a, gdje je svaka od spomenutih C1-C6 alkil, C3-C11 cikloalkil, C6-C10 aril, C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana s jednim ili više R14;
svaki od R14 je nezavisno izabran od C1-C6 alkil, halogen, -CN, -CF3, i OR12a; i
svaki t je nezavisno izabran od 0, 1, 2, 3, 4, 5, i 6; ili
njegova farmaceutski prihvatljiva sol ili solvat.
2. Spoj prema zahtjevu 1, naznačen time, što:
R1, R2, R3, R4 su nezavisno izabrani od vodika, C1-C6 alkil, -(CR12aR12b)thalo, -(CR12aR12b)tCN, -(CR12aR12b)tOR12a, -(CR12aR12b)tN(R12aR12b), -(CR12aR12b)tCF3, i
R10 i R11 su nezavisno izabrani od vodika, -(CR12aR12b)t C1-C6 alkil, -(CR12aR12b)t C3-C11 cikloalkil, -(CR12aR12b)t C6-C10 aril, -(CR12aR12b)t C2-C10 heterociklil i -(CR12aR12b)theteroaril, gdje je svaka od pomenutih C1-C6 alkil, C3-C11 cikloalkil, C6-C10 aril, C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R13; ili
njegova farmaceutski prihvatljiva sol ili solvat.
3. Spoj prema zahtjevu 2, naznačen time, što:
R1, R2, R3, R4 su nezavisno izabrani od vodika, C1-C6 alkil, halo, -CN, -OR12a, i -CF3; i
R5 je vodik; ili
njegova farmaceutski prihvatljiva sol ili solvat.
4. Spoj prema zahtjevu 3, naznačen time, što:
R10 je vodik ili C1-C6 alkil; i
R11 je izabran od -(CR12aR12b)t C1-C6 alkil, -(CR12aR12b)t C3-C11 cikloalkil, -(CR12aR12b)t C6-C10 aril, -(CR12aR12b)t C2-C10 heterociklil i -(CR12aR12b)theteroaril, gdje je svaka od spomenutih C1-C6 alkil, C3-C11 cikloalkil, C6-C10 aril, C2-C10 heterociklil, i heteroaril grupa po izboru supstituirana sa jednim ili više R13; ili
njegova farmaceutski prihvatljiva sol ili solvat.
5. Spoj prema zahtjevu 4, naznačen time, što su R6, R7, R8 i R9 vodik, ili njegova farmaceutski prihvatljiva sol ili solvat.
6. Spoj prema zahtjevu 5, naznačen time, što:
R11 je -(CH2)C6-C10 aril ili -(CH2)2C6-C10 aril, gdje je spomenuta C6-C10 aril grupa po izboru supstituirana sa jednim ili više R13;
R12a je vodik ili C1-C6 alkil; i
svaki od R13 je nezavisno izabran od vodika, C1-C6 alkil, halogen -CN, -CF3; i OCF3; ili
njegova farmaceutski prihvatljiva sol ili solvat.
7. Spoj prema zahtjevu 6, naznačen time, što
R1, R2 i R4 su vodik ̧ i
R3 je C1-C6 alkil, -Cl, -F, -CN, -OCH3, -OCH2CH3, ili -CF3;
R10 je vodik ili -CH3; i
svaki od R13 je nezavisno izabran od, C1-C6 alkil, -Cl, -F, -CN, -CF3; i -OCF3; ili
njegova farmaceutski prihvatljiva sol ili solvat.
8. spoj prema zahtjevu 1, naznačen time, što:
R1, R2, i R4 su vodik,
R3 je -CH3, -OCH3 ili -OCH3CH2
R5 je vodik; i
R6, R7, R8 i R9 su vodik
R10 je vodik ili -CH3, i
R11 je –(CH2)C8-C10aril ili –(CH2)2C6-C10aril gdje je navedeni C6-C10 aril po izboru supstituiran jednim ili više R13; i
svaki se R13neovisno bira od, C1-C6 alkil, -Cl, -F, -CN, -CF3; i -OCF3; ili
njegova farmaceutski prihvatljiva sol ili solvat.
9. spoj prema zahtjevu 1, naznačen time, što:
R1, R2, i R4 su vodik,
R3 je -OCH3 ili -OCH3CH2
R5 je vodik; i
R6, R7, R8 i R9 su vodik
R10 je vodik ili -CH3, i
R11 je –(CH2)C6-C10 aril ili –(CH2)2C6-C10 aril gdje je navedeni C6-C10 aril po izboru supstituiran jednim ili više supstituenata neovisno biranih od –Cl i –F; ili
njegova farmaceutski prihvatljiva sol ili solvat.
10. spoj prema zahtjevu 1, naznačen time, što se odabire od:
N-(3,4-difluorobenzil)-2-{[(5-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-[2-(2-metilfenil)etil]-2-{[(5-metilpiridin-3-il)amino]sulfonil}benzamid;
N-(3,4-diklorobenzil)-2-{[(5-metilpiridin-3-il)amino]sulfonil}benzamid;
N-[4-fluoro-3-(trifluorometil)benzil]-2-{[(5-metilpiridin-3-il)amino]sulfonil}benzamid;
N-[4-fluoro-3-(trifluorometil)benzil]-2-{[(5-metoksipiridin-3 il)amino]sulfonil}benzamid;
2-{[(5-etoksipiridin-3-il)amino]sulfonil}-N-[2-(2-metilfenil)etil]benzamid;
N-(3,4-diklorobenzil)-2-{[(5-etoksipiridin-3-il)amino]sulfonil}benzamid;
N-(3,4-difluorobenzil)-2-{[(5-toksipiridin-3-il)amino]sulfonil}-N-metilbenzamid;
2-{[(4-etoksipiridin-3-il)amino]sulfonil}-N-[4-fluoro-3-(trifluorometil)benzil]benzamid;
2-{[(5-etoksipiridin-3-il)amino]sulfonil}-N-[4-fluoro-3-(trifluorometil)benzil]benzamid;
N-(3,4-difluorobenzil)-2-{[(4-etoksipiridin-3-il)amino]sulfonil}-N-metilbenzamid;
N-(4-kloro-2-metilbenzil)-2-{[(5-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-(3-kloro-2-metilbenzil)-2-{[(5-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-(3,5-diklorobenzil)-2-{[(5-metilpiridin-3-il)amino]sulfonil}benzamid; i
N-(3,4-difluorobenzil)-2-{[(4-metoksipiridin-3-il)amino]sulfonil}-N-metilbenzamid;
ili njegova farmaceutski prihvatljiva sol ili solvate.
11. spoj prema zahtjevu 1, naznačen time, što se odabire od:
N-(3,4-difluorobenzil)-2-{[(4-metoksipiridin-3-il)amino]sulfonil}-Nmetilbenzamid;
N-(3,4-difluorobenzil)-2-{[(4-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-[2-(2-fluorofenil)etil]-2-{[(5-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-[4-fluoro-3-(trifluorometil)benzil]-2-{[(4-metoksipiridin-3-il)amino]sulfonil}benzamid;
N-(3,4-difluorobenzil)-2-{[(4-etoksipiridin-3-il)amino]sulfonil}benzamid; i
N-(3,4-difluorobenzil)-2-{[(4-etoksipiridin-3-il)amino]sulfonil}-N-metilbenzamid; ili
njegova farmaceutski prihvatljiva sol ili solvat.
12. farmaceutska kompozicija, naznačena time, što sadrži efektivnu količinu najmanje jednog spoja prema bilo kome od zahtjeva 1 do 11, i farmaceutski prihvatljiv nosač.
13. Farmaceutska kompozicija prema zahtjevu 12, naznačena time, što dalje sadrži inhibitor HIV proteaze odabranu od amprenavira, nelfinavira, ritonavira, sakvinavira, inviraze, lopinavira, atazanavira, palinavira, indinavira, tipranavira, darunavira, brecanavira, (4R)-N-alil-3-{(2S,3S)-2-hidroksi-3-[(3-hidroksi-2-metilbenzoil)amino]-4-fenilbutanoil}-5,5-dimetil-1,3-tiazolidlne-4-karboksamida, i fosamprenavir kalcija.
14. Primjena prvog spoja i drugog spoja za dobijanje lijeka za liječenje infekcije HIV-om kod sisavaca inficiranih HIV-om, naznačena time, što je prvi spoj odabran od onih prema bilo kojim od zahtjeva 1 do 11, a drugi spoj je anti-HIV spoj.
15. primjena prema zahtjevu 19, gdje je, naznačeni drugi spoj (N-{(1S)-3-[3-izopzopil-5-metil-4H-1,2,4-triazol-4-il]-egzo-8-azadiciklo[3.2.1]okt-8-il}-1-fenilpropil)-4,4-difluorocikloheksan-karboksamid), etil-1-endo-{8-[(3S)-3-(acetilamino)-3-(3-fluorofenil)propil]-8-azadiciklo[3.2.1]okt-3-il}-2-metil-4,5,6,7-tetrahidro-1H-imidazol[4,5-c]piridin-5-karboksilat, ili N-{(1S)-3-[3-endo-(5-izobutiril-2-metil-4,5,6,7-tetrahidro- 1H-imidazo[4.5-c]piridin-1-il)-8-azadiciklo[3.2.1]okt-8-il]-1-(3-fluorofenil)propil}-acetamid).
16. Primjena prema zahtjevu 14, gdje je naznačeni drugi spoj odabran od amprenavira, CGP-73547, CGP-61755, DMP-450, nelfinavira, ritonavira, sakvinavira, inviraze, lopinavira, TCM-126, atazanavira, palinavira, GS-333, KN I-413, KNI-272, LG-71350, CGP-61755, PD 173606, PD 173606, PD 177298, PD 178390, PD 178392, U-140690, ABT-378, DMP-450, AG-1776, MK-944, VX-478, indinavira, tipranavira, darunavira, brecanavira, DCP-681, DPC-684, (4R)-N-alil-3-{(2S,3S)-2-hidroksi-3-[(3-hidroksi-2-metilbenzoil)amino]-4-fenilbutanoil}-5,5-dimetil-1,3-tiazolidin-4-karboksamida, i fosamprenavir kalcija.
17. Primjena prvog spoja i drugog spoja, naznačena time što je za pripravu lijeka za poboljšanje farmakokinetike kod sisavca, gdje je navedeni prvi spoj anti-HIV spoj i navedeni drugi spoj se odabire od onih prema bilo kojem od zahtjeva 1 do 11.
18. Primjena prema zahtjevu 17, naznačena time što je navedeno anti-HIV spoj amprenavir, CGP-73547, CGP-61755, DMP-450, nelfinavir, ritonavir, sakvinavir, inviraza, lopinavir, TCM-126, atazanavir, palinavir, GS-333, KN I-413, KNI-272, LG-71350, CGP-61755, PD 173606, PD 173606, PD 177298, PD 178390, PD 178392, U-140690, ABT-378, DMP-450, AG-1776, MK-944, VX-478, indinavir, tipranavir, darunavir, brecanavir, DCP-681, DPC-684, (4R)-N-alil-3-{(2S,3S)-2-hidroksi-3-[(3-hidroksi-2-metilbenzoil)amino]-4-fenilbutanoil}-5,5-dimetil-1,3-tiazolidin-4-karboksamid, i fosamprenavir kalcij.
19. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time da je za liječenje infekcije HIV-om kod sisavca inficiranog HIV-om.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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US72015105P | 2005-09-23 | 2005-09-23 | |
US72311505P | 2005-10-03 | 2005-10-03 | |
US72546905P | 2005-10-11 | 2005-10-11 | |
US76225606P | 2006-01-25 | 2006-01-25 | |
US82166406P | 2006-08-07 | 2006-08-07 | |
PCT/IB2006/002639 WO2007034312A2 (en) | 2005-09-23 | 2006-09-11 | Pyridinaminosulfonyl substituted benzamides as inhibitors of cytochrome p450 3a4 (cyp3a4) |
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DE (1) | DE602006012713D1 (hr) |
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Families Citing this family (21)
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MX2009000482A (es) * | 2006-07-05 | 2009-01-27 | Pfizer Prod Inc | Compuestos terapeuticos. |
AU2007343726A1 (en) * | 2006-12-26 | 2008-07-24 | Amgen Inc. | N-cyclohexyl benzamides and benzeneacetamides as inhibitors of 11-beta-hydroxysteroid dehydrogenases |
AU2008226947B2 (en) | 2007-03-08 | 2014-07-17 | The Board Of Trustees Of The Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
ES2460897T3 (es) * | 2007-10-04 | 2014-05-14 | F. Hoffmann-La Roche Ag | Derivados de ciclopropil aril amida y usos de los mismos |
CN102209541B (zh) | 2008-09-08 | 2016-05-18 | 小利兰·斯坦福大学托管委员会 | 醛脱氢酶活性调节剂和其使用方法 |
US8389522B2 (en) | 2008-10-28 | 2013-03-05 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
GEP20135992B (en) | 2009-01-12 | 2013-12-25 | Icagen Inc | Sulfonamide derivatives |
CN102427810A (zh) * | 2009-05-01 | 2012-04-25 | 拉夸里亚创药株式会社 | 作为trpm8拮抗剂的氨磺酰基苯甲酸衍生物 |
EP2590972B1 (en) | 2010-07-09 | 2015-01-21 | Pfizer Limited | N-sulfonylbenzamides as inhibitors of voltage-gated sodium channels |
US10457659B2 (en) | 2011-04-29 | 2019-10-29 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
WO2014000178A1 (en) * | 2012-06-27 | 2014-01-03 | Merck Sharp & Dohme Corp. | Sulfonamide derivatives and methods of use thereof for improving the pharmacokinetics of a drug |
CN104540813A (zh) * | 2012-06-27 | 2015-04-22 | 默沙东公司 | 磺酰胺衍生物以及使用它们用于改善药物的药物动力学的方法 |
JP6410790B2 (ja) | 2013-03-14 | 2018-10-24 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | ミトコンドリアアルデヒドデヒドロゲナーゼ−2調節因子およびその使用方法 |
TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
WO2014194519A1 (en) | 2013-06-07 | 2014-12-11 | Merck Sharp & Dohme Corp. | Imidazole derivatives and methods of use thereof for improving pharmacokinetics of drug |
WO2015070366A1 (en) | 2013-11-12 | 2015-05-21 | Merck Sharp & Dohme Corp. | Aryl linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug |
WO2015070367A1 (en) | 2013-11-12 | 2015-05-21 | Merck Sharp & Dohme Corp. | Piperidine or piperazine linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug |
MA39792B1 (fr) | 2014-03-26 | 2019-12-31 | Hoffmann La Roche | Composés bicycliques en tant qu'inhibiteurs de production d'autotaxine (atx) et d'acide lysophosphatidique (lpa) |
WO2016101118A1 (en) * | 2014-12-23 | 2016-06-30 | Merck Sharp & Dohme Corp. | Amidoethyl azole orexin receptor antagonists |
UA123362C2 (uk) | 2015-09-04 | 2021-03-24 | Ф. Хоффманн-Ля Рош Аг | Феноксиметильні похідні |
WO2018167113A1 (en) | 2017-03-16 | 2018-09-20 | F. Hoffmann-La Roche Ag | New bicyclic compounds as atx inhibitors |
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US7169763B2 (en) * | 2002-02-22 | 2007-01-30 | Oliver Yoa-Pu Hu | Cytochrome P450 3A inhibitors and enhancers |
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