RU2021133444A - Производные бензимидазола в качестве модуляторов ror-гамма - Google Patents
Производные бензимидазола в качестве модуляторов ror-гамма Download PDFInfo
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- RU2021133444A RU2021133444A RU2021133444A RU2021133444A RU2021133444A RU 2021133444 A RU2021133444 A RU 2021133444A RU 2021133444 A RU2021133444 A RU 2021133444A RU 2021133444 A RU2021133444 A RU 2021133444A RU 2021133444 A RU2021133444 A RU 2021133444A
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- benzyl
- benzo
- ethylsulfonyl
- carboxamide
- imidazole
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 150000001556 benzimidazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- -1 (5 - ((4- (ethylsulfonyl) benzyl) carbamoyl) -2- (trifluoromethyl) -1H-benzo [d] imidazol-1-yl) methyl Chemical group 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 208000031212 Autoimmune polyendocrinopathy Diseases 0.000 claims 2
- 208000015943 Coeliac disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 102000001691 Member 3 Group F Nuclear Receptor Subfamily 1 Human genes 0.000 claims 2
- 108010029279 Member 3 Group F Nuclear Receptor Subfamily 1 Proteins 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000011385 autoimmune polyendocrine syndrome Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- DDWMEFBTXCVJBA-QGZVFWFLSA-N 1-[(1R)-1-(3-cyanophenyl)ethyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)[C@@H](C)N1C(=NC2=C1C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C(F)(F)F DDWMEFBTXCVJBA-QGZVFWFLSA-N 0.000 claims 1
- DDWMEFBTXCVJBA-KRWDZBQOSA-N 1-[(1S)-1-(3-cyanophenyl)ethyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)[C@H](C)N1C(=NC2=C1C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C(F)(F)F DDWMEFBTXCVJBA-KRWDZBQOSA-N 0.000 claims 1
- VHMVOQCYXDEOPI-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound CCS(=O)(=O)C1=CC=C(CNC(=O)C2=CC=C3N(CC4=CC(OC)=CC(OC)=C4)C(=NC3=C2)C(F)(F)F)C=C1 VHMVOQCYXDEOPI-UHFFFAOYSA-N 0.000 claims 1
- ARHBMXMEUHSDNH-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-N-[(5-ethylsulfonylpyridin-2-yl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound CCS(=O)(=O)C1=CN=C(CNC(=O)C2=CC=C3N(CC4=CC(OC)=CC(OC)=C4)C(=NC3=C2)C(F)(F)F)C=C1 ARHBMXMEUHSDNH-UHFFFAOYSA-N 0.000 claims 1
- XIKBHHIANYPGQW-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-N-[[4-(2-hydroxyethylsulfonyl)phenyl]methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN2C3=CC=C(C=C3N=C2C(F)(F)F)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CCO)=C1 XIKBHHIANYPGQW-UHFFFAOYSA-N 0.000 claims 1
- LATRKXNHMMMOGB-UHFFFAOYSA-N 1-[(3-cyano-4-methoxyphenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound CCS(=O)(=O)C1=CC=C(CNC(=O)C2=CC=C3N(CC4=CC(C#N)=C(OC)C=C4)C(=NC3=C2)C(F)(F)F)C=C1 LATRKXNHMMMOGB-UHFFFAOYSA-N 0.000 claims 1
- JHIVSPUFOSIRMF-UHFFFAOYSA-N 1-[(3-cyanophenyl)methyl]-2-cyclopropyl-N-[(4-ethylsulfonylphenyl)methyl]benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=C(CN2C(=NC3=C2C=CC(=C3)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CC)C2CC2)C=CC=1 JHIVSPUFOSIRMF-UHFFFAOYSA-N 0.000 claims 1
- ZCLLGTIHAOOKDY-UHFFFAOYSA-N 1-[(3-cyanophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=C(CN2C(=NC3=C2C=CC(=C3)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CC)C(F)(F)F)C=CC=1 ZCLLGTIHAOOKDY-UHFFFAOYSA-N 0.000 claims 1
- YKAXZFOZDBETME-UHFFFAOYSA-N 1-[(4-cyanophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound CCS(=O)(=O)C1=CC=C(CNC(=O)C2=CC=C3N(CC4=CC=C(C=C4)C#N)C(=NC3=C2)C(F)(F)F)C=C1 YKAXZFOZDBETME-UHFFFAOYSA-N 0.000 claims 1
- WNAQVBSCAMZYPV-UHFFFAOYSA-N 1-[(5-cyano-2-fluorophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=CC(=C(CN2C(=NC3=C2C=CC(=C3)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CC)C(F)(F)F)C=1)F WNAQVBSCAMZYPV-UHFFFAOYSA-N 0.000 claims 1
- NMAARLZCOGRQHC-UHFFFAOYSA-N 1-[1-(3-cyanophenyl)cyclopropyl]-N-[(4-ethylsulfonylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1)C1(CC1)N1C(=NC2=C1C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C(F)(F)F NMAARLZCOGRQHC-UHFFFAOYSA-N 0.000 claims 1
- HTPMRLSJTYXDOB-UHFFFAOYSA-N 1-benzyl-N-[(4-ethylsulfonylphenyl)methyl]-2-methylbenzimidazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=NC2=C1C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C HTPMRLSJTYXDOB-UHFFFAOYSA-N 0.000 claims 1
- CTGRRUBFNUFPDM-UHFFFAOYSA-N 2-cyclopropyl-1-[(2,3-dihydroxyphenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]benzimidazole-5-carboxamide Chemical compound CCS(=O)(=O)c1ccc(CNC(=O)c2ccc3n(Cc4cccc(O)c4O)c(nc3c2)C2CC2)cc1 CTGRRUBFNUFPDM-UHFFFAOYSA-N 0.000 claims 1
- PGYXUXKOYRWSSJ-UHFFFAOYSA-N 2-cyclopropyl-1-[(2,3-dimethoxyphenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1CC1=C(C(=CC=C1)OC)OC)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC PGYXUXKOYRWSSJ-UHFFFAOYSA-N 0.000 claims 1
- TVKSDSIXDXGUAT-UHFFFAOYSA-N 2-cyclopropyl-1-[(3,5-dimethoxyphenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1CC1=CC(=CC(=C1)OC)OC)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC TVKSDSIXDXGUAT-UHFFFAOYSA-N 0.000 claims 1
- QQUWAQNLGQWKIF-UHFFFAOYSA-N 2-cyclopropyl-1-[[3-(difluoromethoxy)phenyl]methyl]-N-[(4-ethylsulfonylphenyl)methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1CC1=CC(=CC=C1)OC(F)F)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC QQUWAQNLGQWKIF-UHFFFAOYSA-N 0.000 claims 1
- IUHSSFCXMNFPOI-OAQYLSRUSA-N 2-cyclopropyl-N-[(4-ethylsulfonylphenyl)methyl]-1-[[(2R)-1-(2,2,2-trifluoroethyl)pyrrolidin-2-yl]methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1C[C@@H]1N(CCC1)CC(F)(F)F)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC IUHSSFCXMNFPOI-OAQYLSRUSA-N 0.000 claims 1
- PXZVYIYYIISSAN-HSZRJFAPSA-N 2-cyclopropyl-N-[(4-ethylsulfonylphenyl)methyl]-1-[[(2R)-1-(5-fluoropyrimidin-2-yl)pyrrolidin-2-yl]methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1C[C@@H]1N(CCC1)C1=NC=C(C=N1)F)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC PXZVYIYYIISSAN-HSZRJFAPSA-N 0.000 claims 1
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- JZVFMUCBDJLMIE-IBGZPJMESA-N 2-cyclopropyl-N-[(4-ethylsulfonylphenyl)methyl]-1-[[(3S)-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]methyl]benzimidazole-5-carboxamide Chemical compound C1(CC1)C1=NC2=C(N1C[C@@H]1CN(CC1)CC(F)(F)F)C=CC(=C2)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC JZVFMUCBDJLMIE-IBGZPJMESA-N 0.000 claims 1
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- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 208000015768 polyposis Diseases 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 208000012672 seasonal affective disease Diseases 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 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 1
Classifications
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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| SMT202100286T1 (it) | 2015-05-15 | 2021-07-12 | Aurigene Discovery Tech Ltd | Composti di tetraidrochinolinone sostituito come modulatori ror-gamma |
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| US11008340B2 (en) | 2015-11-20 | 2021-05-18 | Vitae Pharmaceuticals, Llc | Modulators of ROR-gamma |
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-
2017
- 2017-01-26 TW TW111104096A patent/TW202220968A/zh unknown
- 2017-01-26 TW TW106103216A patent/TWI757266B/zh not_active IP Right Cessation
- 2017-01-27 BR BR112018015273A patent/BR112018015273A2/pt not_active Application Discontinuation
- 2017-01-27 CN CN201780009016.0A patent/CN109071509B/zh not_active Expired - Fee Related
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- 2017-01-27 RU RU2021133444A patent/RU2021133444A/ru unknown
- 2017-01-27 AU AU2017212577A patent/AU2017212577B2/en not_active Ceased
- 2017-01-27 WO PCT/US2017/015220 patent/WO2017132432A1/en not_active Ceased
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2018
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2020
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2021
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| MX381313B (es) | 2025-03-12 |
| CN109071509B (zh) | 2021-11-30 |
| TWI757266B (zh) | 2022-03-11 |
| JP6948333B2 (ja) | 2021-10-13 |
| US20190352286A1 (en) | 2019-11-21 |
| JP2021193131A (ja) | 2021-12-23 |
| WO2017132432A8 (en) | 2017-08-31 |
| UY37098A (es) | 2017-08-31 |
| AU2017212577B2 (en) | 2021-05-13 |
| AU2017212577A1 (en) | 2018-08-02 |
| US10829481B2 (en) | 2020-11-10 |
| WO2017132432A1 (en) | 2017-08-03 |
| EP3408268A1 (en) | 2018-12-05 |
| MA55328A (fr) | 2022-01-19 |
| TW202220968A (zh) | 2022-06-01 |
| KR20180100697A (ko) | 2018-09-11 |
| RU2760366C2 (ru) | 2021-11-24 |
| MA45646A (fr) | 2021-03-24 |
| MX2018009257A (es) | 2018-11-09 |
| US20210094940A1 (en) | 2021-04-01 |
| CN114230523A (zh) | 2022-03-25 |
| SA518392101B1 (ar) | 2022-03-16 |
| EP3408268B1 (en) | 2021-08-04 |
| EP3408268B8 (en) | 2023-12-06 |
| TW201734001A (zh) | 2017-10-01 |
| RU2018127360A (ru) | 2020-03-02 |
| CA3011838A1 (en) | 2017-08-03 |
| EP3939974A1 (en) | 2022-01-19 |
| RU2018127360A3 (https=) | 2020-04-06 |
| CN109071509A (zh) | 2018-12-21 |
| JP2019503385A (ja) | 2019-02-07 |
| BR112018015273A2 (pt) | 2018-12-18 |
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