PL208713B1 - Związek stanowiący pochodną tiofenu, kompozycja farmaceutyczna zawierająca taki związek i jego zastosowanie - Google Patents

Info

Publication number

PL208713B1

PL208713B1 PL367080A PL36708002A PL208713B1 PL 208713 B1 PL208713 B1 PL 208713B1 PL 367080 A PL367080 A PL 367080A PL 36708002 A PL36708002 A PL 36708002A PL 208713 B1 PL208713 B1 PL 208713B1

Authority

PL

Poland

Prior art keywords

thiophene

phenyl

compound

carboxylic

amino

Prior art date

2001-06-11

Links

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• 150000003577 thiophenes Chemical class 0.000 title claims description 3
• 239000003443 antiviral agent Substances 0.000 title description 6
• 206010054261 Flavivirus infection Diseases 0.000 title 1
• -1 cyano, azido, amidino Chemical group 0.000 claims description 1123
• 239000002253 acid Substances 0.000 claims description 669
• 150000001875 compounds Chemical class 0.000 claims description 616
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 110
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 103
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 98
• 125000001544 thienyl group Chemical group 0.000 claims description 74
• 125000004076 pyridyl group Chemical group 0.000 claims description 72
• 125000002541 furyl group Chemical group 0.000 claims description 62
• 125000000335 thiazolyl group Chemical group 0.000 claims description 62
• 125000000623 heterocyclic group Chemical group 0.000 claims description 61
• 125000004193 piperazinyl group Chemical group 0.000 claims description 61
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 59
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 59
• 125000003725 azepanyl group Chemical group 0.000 claims description 58
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 58
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 58
• 125000003386 piperidinyl group Chemical group 0.000 claims description 58
• 229910052736 halogen Inorganic materials 0.000 claims description 56
• 150000002367 halogens Chemical class 0.000 claims description 56
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 54
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 52
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 52
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 52
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 47
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 47
• 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 46
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 46
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 45
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 45
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 44
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 40
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 241000711549 Hepacivirus C Species 0.000 claims description 33
• 125000001041 indolyl group Chemical group 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000000532 dioxanyl group Chemical group 0.000 claims description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 230000003612 virological effect Effects 0.000 claims description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 108060004795 Methyltransferase Proteins 0.000 claims description 16
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 9
• 241000710831 Flavivirus Species 0.000 claims description 9
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
• 208000015181 infectious disease Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 8
• 125000006491 4-t-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 229910052738 indium Inorganic materials 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 7
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 150000001409 amidines Chemical class 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000004494 ethyl ester group Chemical group 0.000 claims description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 125000005936 piperidyl group Chemical group 0.000 claims description 6
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 6
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
• ORGXXKHNNJNAPB-UHFFFAOYSA-N 3-[(4-chlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)C1=CC=C(Cl)C=C1 ORGXXKHNNJNAPB-UHFFFAOYSA-N 0.000 claims description 5
• 208000036142 Viral infection Diseases 0.000 claims description 5
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 230000009385 viral infection Effects 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• NYYKDALOYDQKPA-UHFFFAOYSA-N 3-(n-(2,4-dichlorobenzoyl)anilino)-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C=C1Cl NYYKDALOYDQKPA-UHFFFAOYSA-N 0.000 claims description 4
• GZNQIZXDGFRFOT-UHFFFAOYSA-N 3-[(2-chloro-4-cyanophenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(=CC=2)C#N)Cl)=C(C(O)=O)S1 GZNQIZXDGFRFOT-UHFFFAOYSA-N 0.000 claims description 4
• CORJOVCCNWIHJE-UHFFFAOYSA-N 3-[(2-chlorophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC=C1Cl CORJOVCCNWIHJE-UHFFFAOYSA-N 0.000 claims description 4
• BACMTCNFHNDMIM-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 BACMTCNFHNDMIM-UHFFFAOYSA-N 0.000 claims description 4
• CDEZPEKCNFPDPF-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-5-(4-chlorophenyl)thiophene-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC2=C(SC(=C2)C=2C=CC(Cl)=CC=2)C(O)=O)=C1C CDEZPEKCNFPDPF-UHFFFAOYSA-N 0.000 claims description 4
• NXUAAIVUPKHHNC-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=C(C(O)=O)S1 NXUAAIVUPKHHNC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 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 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 229910052705 radium Inorganic materials 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 150000003536 tetrazoles Chemical class 0.000 claims description 4
• 125000003944 tolyl group Chemical group 0.000 claims description 4
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims description 3
• NSTBKJQXCZFJQD-UHFFFAOYSA-N 3-(benzenesulfonamido)-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC=C1 NSTBKJQXCZFJQD-UHFFFAOYSA-N 0.000 claims description 3
• WRAGVVOJOWAXNX-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-(1-phenylethyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C=CC=CC=1C(C)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=C(Cl)C=C1Cl WRAGVVOJOWAXNX-UHFFFAOYSA-N 0.000 claims description 3
• JOAHXELYGZYEKF-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-(1-piperidin-4-ylethyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(C)C1CCNCC1 JOAHXELYGZYEKF-UHFFFAOYSA-N 0.000 claims description 3
• ZDEYYXQNNKHDQW-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-piperidin-4-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1N(C(=O)C=1C(=CC(Cl)=CC=1)Cl)C1CCNCC1 ZDEYYXQNNKHDQW-UHFFFAOYSA-N 0.000 claims description 3
• HRSASDAMXLSXNA-UHFFFAOYSA-N 3-[(4-bromo-2-methylphenyl)sulfonylamino]-5-[4-(2-methylpropyl)phenyl]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=C(C(O)=O)S1 HRSASDAMXLSXNA-UHFFFAOYSA-N 0.000 claims description 3
• BMWYCRYHUCPJQB-UHFFFAOYSA-N 3-[(4-chloro-2,5-dimethylphenyl)sulfonyl-[(3-iodophenyl)methyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)N(CC=2C=C(I)C=CC=2)C2=C(SC(=C2)C=2C=CC=CC=2)C(O)=O)=C1C BMWYCRYHUCPJQB-UHFFFAOYSA-N 0.000 claims description 3
• CEYROHUHAOEQKA-UHFFFAOYSA-N 3-[(4-methylphenyl)methyl-(2-methylpropanoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(=O)C(C)C)CC1=CC=C(C)C=C1 CEYROHUHAOEQKA-UHFFFAOYSA-N 0.000 claims description 3
• NJYCOGNPAOHBPY-UHFFFAOYSA-N 3-[(4-methylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 NJYCOGNPAOHBPY-UHFFFAOYSA-N 0.000 claims description 3
• HCWAVDVJWSEPGB-UHFFFAOYSA-N 3-[(4-nitrophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 HCWAVDVJWSEPGB-UHFFFAOYSA-N 0.000 claims description 3
• INSHPAQZHIADPY-UHFFFAOYSA-N 3-[[4-(2-chlorophenyl)piperazine-1-carbonyl]amino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NC(=O)N(CC1)CCN1C1=CC=CC=C1Cl INSHPAQZHIADPY-UHFFFAOYSA-N 0.000 claims description 3
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 3
• RCLMWXCWXOTDLV-UHFFFAOYSA-N 5-(2-methoxyphenyl)-3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound COC1=CC=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC=CC=2)C)=C(C(O)=O)S1 RCLMWXCWXOTDLV-UHFFFAOYSA-N 0.000 claims description 3
• HTZLXJVFYOWLRB-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=C(Cl)C=CC=2)=C1 HTZLXJVFYOWLRB-UHFFFAOYSA-N 0.000 claims description 3
• XAHFETWNXTYUNL-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-[methyl-(4-methylbenzoyl)amino]thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(Cl)C=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(C)C=C1 XAHFETWNXTYUNL-UHFFFAOYSA-N 0.000 claims description 3
• ZFZJJUVWTSSAKV-UHFFFAOYSA-N 5-(3-methylphenyl)-3-[(2-methylphenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC(C=2SC(=C(NS(=O)(=O)C=3C(=CC=CC=3)C)C=2)C(O)=O)=C1 ZFZJJUVWTSSAKV-UHFFFAOYSA-N 0.000 claims description 3
• ILSVCOAMNUHJHS-UHFFFAOYSA-N 5-(4-cyanophenyl)-3-[methyl-(4-methylbenzoyl)amino]thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC(=CC=2)C#N)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(C)C=C1 ILSVCOAMNUHJHS-UHFFFAOYSA-N 0.000 claims description 3
• UJFMCKASZXENEG-UHFFFAOYSA-N 5-[4-(2-methylpropyl)phenyl]-3-[(2,3,4-trifluorophenyl)sulfonylamino]thiophene-2-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=C(F)C(F)=CC=2)F)=C(C(O)=O)S1 UJFMCKASZXENEG-UHFFFAOYSA-N 0.000 claims description 3
• YVZWGWVMODRXBK-UHFFFAOYSA-N 5-phenyl-3-[[2-(trifluoromethyl)phenyl]sulfonylamino]thiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC=C1C(F)(F)F YVZWGWVMODRXBK-UHFFFAOYSA-N 0.000 claims description 3
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 claims description 3
• 241001024304 Mino Species 0.000 claims description 3
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 claims description 3
• 229940126179 compound 72 Drugs 0.000 claims description 3
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 claims description 3
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
• 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
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• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
• VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 claims 1
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• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 1
• PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 claims 1
• FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims 1
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims 1
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
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• DWQUAPIEHOIEQQ-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-(1,3-dihydroxypropan-2-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(CO)CO)C(=O)C1=CC=C(Cl)C=C1Cl DWQUAPIEHOIEQQ-UHFFFAOYSA-N 0.000 claims 1
• XKOSCJAUHRVOPI-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-propan-2-ylamino]-5-(3-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=C(C=2C=C(C)C=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1Cl XKOSCJAUHRVOPI-UHFFFAOYSA-N 0.000 claims 1
• LUUIBUPKEZXBPP-UHFFFAOYSA-N 3-[(2,4-dichlorobenzoyl)-propan-2-ylamino]-5-piperidin-4-ylthiophene-2-carboxylic acid Chemical compound C1=C(C2CCNCC2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1Cl LUUIBUPKEZXBPP-UHFFFAOYSA-N 0.000 claims 1
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• HQFLWMORIZZXHF-UHFFFAOYSA-N 3-[(2,4-difluorophenyl)sulfonylamino]-5-(4-fluorophenyl)thiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC(F)=CC=2)=CC=1NS(=O)(=O)C1=CC=C(F)C=C1F HQFLWMORIZZXHF-UHFFFAOYSA-N 0.000 claims 1
• DSUMSXCFDTVNNF-UHFFFAOYSA-N 3-[(2,4-dimethylbenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(C)C=C1C DSUMSXCFDTVNNF-UHFFFAOYSA-N 0.000 claims 1
• YIKVXZJXLVDZIZ-UHFFFAOYSA-N 3-[(2,4-dimethylphenyl)sulfonylamino]-5-(4-methylsulfonylphenyl)thiophene-2-carboxylic acid Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 YIKVXZJXLVDZIZ-UHFFFAOYSA-N 0.000 claims 1
• RTIMLZXIJBOCGN-UHFFFAOYSA-N 3-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C=1C=C(Cl)SC=1Cl RTIMLZXIJBOCGN-UHFFFAOYSA-N 0.000 claims 1
• UOJWDCADFJVARK-UHFFFAOYSA-N 3-[(2,5-dimethylphenyl)sulfonylamino]-5-(4-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC(NS(=O)(=O)C=2C(=CC=C(C)C=2)C)=C(C(O)=O)S1 UOJWDCADFJVARK-UHFFFAOYSA-N 0.000 claims 1
• VBCJTECWBMOYCO-UHFFFAOYSA-N 3-[(2-amino-4-chlorobenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1N VBCJTECWBMOYCO-UHFFFAOYSA-N 0.000 claims 1
• BZAQHGRGVAQDPH-UHFFFAOYSA-N 3-[(2-bromo-4-chlorobenzoyl)-methylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(Cl)C=C1Br BZAQHGRGVAQDPH-UHFFFAOYSA-N 0.000 claims 1
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• JDGZCKCRTKXERS-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]-5-(1,3-thiazol-2-yl)thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2SC=CN=2)=C1 JDGZCKCRTKXERS-UHFFFAOYSA-N 0.000 claims 1
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• DQDZZXKMHJAUQM-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]-5-(4-methylsulfonylphenyl)thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 DQDZZXKMHJAUQM-UHFFFAOYSA-N 0.000 claims 1
• MYINBAPRIZCUIV-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfonylamino]-5-[2-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C(=CC=CC=2)C(F)(F)F)=C1 MYINBAPRIZCUIV-UHFFFAOYSA-N 0.000 claims 1
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• RCTWLZKPLKYHAX-UHFFFAOYSA-N 3-[(3,5-dichlorobenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC(Cl)=CC(Cl)=C1 RCTWLZKPLKYHAX-UHFFFAOYSA-N 0.000 claims 1
• WGHSOYCMWSFBLO-UHFFFAOYSA-N 3-[(3-carboxycyclopentyl)-(2,4-dichlorobenzoyl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1C(C(=O)O)CCC1N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=C(Cl)C=C1Cl WGHSOYCMWSFBLO-UHFFFAOYSA-N 0.000 claims 1
• SBOHZVRRASXAJB-UHFFFAOYSA-N 3-[(3-fluorophenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 SBOHZVRRASXAJB-UHFFFAOYSA-N 0.000 claims 1
• ISEQPBXIOKXRGA-UHFFFAOYSA-N 3-[(4-chloro-2-fluorobenzoyl)-propan-2-ylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C(C)C)C(=O)C1=CC=C(Cl)C=C1F ISEQPBXIOKXRGA-UHFFFAOYSA-N 0.000 claims 1
• MNHXBYXMXSZEQV-UHFFFAOYSA-N 3-[(4-chloro-2-methylphenyl)sulfonylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound CC1=CC(Cl)=CC=C1S(=O)(=O)NC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 MNHXBYXMXSZEQV-UHFFFAOYSA-N 0.000 claims 1
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• RBSSXGJWFHIKDF-UHFFFAOYSA-N 3-[(4-methylcyclohexanecarbonyl)-(oxan-4-yl)amino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C(O)=O)C1CCOCC1 RBSSXGJWFHIKDF-UHFFFAOYSA-N 0.000 claims 1
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• DGBFOKFOXSKYJJ-UHFFFAOYSA-N 3-[[3-fluoro-4-(trifluoromethyl)benzoyl]-methylamino]-5-phenylthiophene-2-carboxylic acid Chemical compound C1=C(C=2C=CC=CC=2)SC(C(O)=O)=C1N(C)C(=O)C1=CC=C(C(F)(F)F)C(F)=C1 DGBFOKFOXSKYJJ-UHFFFAOYSA-N 0.000 claims 1
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