JP2018534326A5 - - Google Patents
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- JP2018534326A5 JP2018534326A5 JP2018526160A JP2018526160A JP2018534326A5 JP 2018534326 A5 JP2018534326 A5 JP 2018534326A5 JP 2018526160 A JP2018526160 A JP 2018526160A JP 2018526160 A JP2018526160 A JP 2018526160A JP 2018534326 A5 JP2018534326 A5 JP 2018534326A5
- Authority
- JP
- Japan
- Prior art keywords
- ethylsulfonyl
- carboxamide
- benzyl
- tetrahydroisoquinoline
- trifluoromethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 8
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 8
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
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- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 206010046851 Uveitis Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 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 4
- 201000001981 dermatomyositis Diseases 0.000 claims description 4
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 201000002859 sleep apnea Diseases 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 206010003805 Autism Diseases 0.000 claims description 2
- 208000020706 Autistic disease Diseases 0.000 claims description 2
- 208000023328 Basedow disease Diseases 0.000 claims description 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000015943 Coeliac disease Diseases 0.000 claims description 2
- 206010011668 Cutaneous leishmaniasis Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 2
- 206010013774 Dry eye Diseases 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 208000015023 Graves' disease Diseases 0.000 claims description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
- 208000001204 Hashimoto Disease Diseases 0.000 claims description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 2
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000003435 Optic Neuritis Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 206010036072 Polyglandular autoimmune syndrome type I Diseases 0.000 claims description 2
- 206010036073 Polyglandular autoimmune syndrome type II Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 206010039705 Scleritis Diseases 0.000 claims description 2
- 210000000577 adipose tissue Anatomy 0.000 claims description 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 230000027288 circadian rhythm Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 208000030533 eye disease Diseases 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 208000024714 major depressive disease Diseases 0.000 claims description 2
- 206010028417 myasthenia gravis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 208000005987 polymyositis Diseases 0.000 claims description 2
- 208000015768 polyposis Diseases 0.000 claims description 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 2
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 201000000306 sarcoidosis Diseases 0.000 claims description 2
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
- 208000012672 seasonal affective disease Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- -1 1- (4- (ethylsulfonyl) phenyl) -2-hydroxyethyl Chemical group 0.000 claims 63
- MBJVWMQHKCGMLZ-UHFFFAOYSA-N isoquinoline-6-carboxamide Chemical compound C1=NC=CC2=CC(C(=O)N)=CC=C21 MBJVWMQHKCGMLZ-UHFFFAOYSA-N 0.000 claims 18
- 238000006467 substitution reaction Methods 0.000 claims 6
- IVLADIVNHDZNSK-UHFFFAOYSA-N 4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-2-[4-(trifluoromethyl)cyclohexyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC)C1CCC(CC1)C(F)(F)F IVLADIVNHDZNSK-UHFFFAOYSA-N 0.000 claims 4
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims 4
- CJYKFLZCVMUMCI-UHFFFAOYSA-N 1-ethyl-N-[1-(5-ethylsulfonylpyridin-2-yl)-2-hydroxyethyl]-2-[[4-(trifluoromethyl)cyclohexyl]methyl]-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound C(C)C1N(CCC2=CC(=CC=C12)C(=O)NC(CO)C1=NC=C(C=C1)S(=O)(=O)CC)CC1CCC(CC1)C(F)(F)F CJYKFLZCVMUMCI-UHFFFAOYSA-N 0.000 claims 3
- WEDJMRANDLLTPD-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound ClC1=CC=C(CN2C(C3=CC=C(C=C3CC2)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CC)C(C)C)C=C1 WEDJMRANDLLTPD-UHFFFAOYSA-N 0.000 claims 3
- UKUTWJYGMWVNQO-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound C(#N)C1=CC=C(CN2C(C3=CC=C(C=C3CC2)C(=O)NCC2=CC=C(C=C2)S(=O)(=O)CC)C(C)C)C=C1 UKUTWJYGMWVNQO-UHFFFAOYSA-N 0.000 claims 3
- CLDTZFVVMPBAMV-UHFFFAOYSA-N 4-ethyl-N-[1-(5-ethylsulfonylpyridin-2-yl)-2-hydroxyethyl]-2-[5-(trifluoromethyl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NC(CO)C1=NC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C(F)(F)F CLDTZFVVMPBAMV-UHFFFAOYSA-N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- RNEFHZGWJCBGEI-UHFFFAOYSA-N 1-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-2-[[4-(trifluoromethyl)cyclohexyl]methyl]-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound C(C)C1N(CCC2=CC(=CC=C12)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC)CC1CCC(CC1)C(F)(F)F RNEFHZGWJCBGEI-UHFFFAOYSA-N 0.000 claims 2
- RCYICNGPHXCHGD-UHFFFAOYSA-N 2-(4,4-difluorocyclohexyl)-4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound FC1(CCC(CC1)N1CC2=CC(=CC=C2C(C1)CC)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC)F RCYICNGPHXCHGD-UHFFFAOYSA-N 0.000 claims 2
- XVPRRDDTOFEXRK-UHFFFAOYSA-N 2-(5-chloropyrimidin-2-yl)-4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound ClC=1C=NC(=NC=1)N1CC2=CC(=CC=C2C(C1)CC)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC XVPRRDDTOFEXRK-UHFFFAOYSA-N 0.000 claims 2
- AWVVEMXVNREPGP-UHFFFAOYSA-N 2-(5-chloropyrimidin-2-yl)-N-[(4-ethylsulfonylphenyl)methyl]-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound ClC=1C=NC(=NC=1)N1CC2=CC(=CC=C2C(C1)C(C)C)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC AWVVEMXVNREPGP-UHFFFAOYSA-N 0.000 claims 2
- BEYLQFIGQFZJLD-UHFFFAOYSA-N 2-(5-cyanopyrimidin-2-yl)-N-[(4-ethylsulfonylphenyl)methyl]-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(#N)C=1C=NC(=NC=1)N1CC2=CC(=CC=C2C(C1)C(C)C)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC BEYLQFIGQFZJLD-UHFFFAOYSA-N 0.000 claims 2
- ITXMNRZJKHDZOF-UHFFFAOYSA-N 2-(5-cyclopropylpyrimidin-2-yl)-4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C1(CC1)C=1C=NC(=NC=1)N1CC2=CC(=CC=C2C(C1)CC)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC ITXMNRZJKHDZOF-UHFFFAOYSA-N 0.000 claims 2
- VKNGBSYGEPDFLV-UHFFFAOYSA-N 2-(5-cyclopropylpyrimidin-2-yl)-N-[(4-ethylsulfonylphenyl)methyl]-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C1(CC1)C=1C=NC(=NC=1)N1CC2=CC(=CC=C2C(C1)C(C)C)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC VKNGBSYGEPDFLV-UHFFFAOYSA-N 0.000 claims 2
- UHPDVSVBQDAZDQ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound CCS(=O)(=O)c1ccc(CNC(=O)c2ccc3C(CN(Cc4ccc(Cl)cc4)Cc3c2)C(C)C)cc1 UHPDVSVBQDAZDQ-UHFFFAOYSA-N 0.000 claims 2
- QQNXIQDFHNYFTO-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-4,4-dimethyl-1-propan-2-yl-1,3-dihydroisoquinoline-6-carboxamide Chemical compound CCS(=O)(=O)C1=CC=C(CNC(=O)C2=CC3=C(C=C2)C(C(C)C)N(CC2=CC=C(C=C2)C#N)CC3(C)C)C=C1 QQNXIQDFHNYFTO-UHFFFAOYSA-N 0.000 claims 2
- XZAULSFNTSZVON-UHFFFAOYSA-N 2-[(4-cyanophenyl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound CCS(=O)(=O)c1ccc(CNC(=O)c2ccc3C(CN(Cc4ccc(cc4)C#N)Cc3c2)C(C)C)cc1 XZAULSFNTSZVON-UHFFFAOYSA-N 0.000 claims 2
- MFFYSSFEMZLWKB-UHFFFAOYSA-N 2-[(5-bromopyrimidin-2-yl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound BrC=1C=NC(=NC=1)CN1C(C2=CC=C(C=C2CC1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C(C)C MFFYSSFEMZLWKB-UHFFFAOYSA-N 0.000 claims 2
- YHEXPNXWAVAZDE-UHFFFAOYSA-N 2-[(6-cyanopyridin-3-yl)methyl]-N-[(4-ethylsulfonylphenyl)methyl]-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound C(#N)C1=CC=C(C=N1)CN1C(C2=CC=C(C=C2CC1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C(C)C YHEXPNXWAVAZDE-UHFFFAOYSA-N 0.000 claims 2
- DYLGIWPZBHWZAH-UHFFFAOYSA-N 2-[3-cyano-5-(trifluoromethyl)pyridin-2-yl]-4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(#N)C=1C(=NC=C(C=1)C(F)(F)F)N1CC2=CC(=CC=C2C(C1)CC)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC DYLGIWPZBHWZAH-UHFFFAOYSA-N 0.000 claims 2
- LLTIDKVXHPASOE-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-1-oxo-2-[4-(trifluoromethyl)phenyl]-3,4-dihydroisoquinoline-7-carboxamide Chemical compound C(C)C1CN(C(C2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)=O)C1=CC=C(C=C1)C(F)(F)F LLTIDKVXHPASOE-UHFFFAOYSA-N 0.000 claims 2
- WKASUUIZRUKDKJ-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[3-methyl-5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=C1C)C(F)(F)F WKASUUIZRUKDKJ-UHFFFAOYSA-N 0.000 claims 2
- OCELEDGSQFIGNF-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=CC=C(C=C1)C(F)(F)F OCELEDGSQFIGNF-UHFFFAOYSA-N 0.000 claims 2
- ZFELUJFSKIJDFR-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[5-(1,3-oxazol-2-yl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C=1OC=CN=1 ZFELUJFSKIJDFR-UHFFFAOYSA-N 0.000 claims 2
- WSLJMNIONMUQAI-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[5-(6-methoxypyridin-2-yl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C1=NC(=CC=C1)OC WSLJMNIONMUQAI-UHFFFAOYSA-N 0.000 claims 2
- YDKUBJNYCMXMQK-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=C1)C(F)(F)F YDKUBJNYCMXMQK-UHFFFAOYSA-N 0.000 claims 2
- CDRVSRKDPZGRMG-UHFFFAOYSA-N 4-ethyl-N-[(4-ethylsulfonylphenyl)methyl]-2-[5-(trifluoromethyl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C(F)(F)F CDRVSRKDPZGRMG-UHFFFAOYSA-N 0.000 claims 2
- IHNLYKIRZZHIGX-UHFFFAOYSA-N 4-ethyl-N-[(5-ethylsulfonylpyridin-2-yl)methyl]-2-[5-(trifluoromethyl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NCC1=NC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C(F)(F)F IHNLYKIRZZHIGX-UHFFFAOYSA-N 0.000 claims 2
- HCPWMOUGFUFZLD-UHFFFAOYSA-N 4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-2-[3-methyl-5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=C1C)C(F)(F)F HCPWMOUGFUFZLD-UHFFFAOYSA-N 0.000 claims 2
- XXYURANIAKOSRM-UHFFFAOYSA-N 4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-2-[5-(1,3-oxazol-2-yl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)C1CN(CC2=CC(=CC=C12)C(=O)NC(CO)C1=CC=C(C=C1)S(=O)(=O)CC)C1=NC=C(C=N1)C=1OC=CN=1 XXYURANIAKOSRM-UHFFFAOYSA-N 0.000 claims 2
- HWPHCHQXRUBKQX-UHFFFAOYSA-N 4-ethyl-N-[1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-2-[5-(trifluoromethyl)pyrimidin-2-yl]-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound CCC1CN(Cc2cc(ccc12)C(=O)NC(CO)c1ccc(cc1)S(=O)(=O)CC)c1ncc(cn1)C(F)(F)F HWPHCHQXRUBKQX-UHFFFAOYSA-N 0.000 claims 2
- IJYFGHNGDSESCT-UHFFFAOYSA-N 7-(5-chloropyrimidin-2-yl)-N-[(4-ethylsulfonylphenyl)methyl]-8-propan-2-yl-6,8-dihydro-5H-1,7-naphthyridine-3-carboxamide Chemical compound ClC=1C=NC(=NC=1)N1CCC=2C=C(C=NC=2C1C(C)C)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)CC IJYFGHNGDSESCT-UHFFFAOYSA-N 0.000 claims 2
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- JEOFWLXRHNLPPF-UHFFFAOYSA-N N-[(4-ethylsulfonylphenyl)methyl]-2-(5-morpholin-4-ylpyrimidin-2-yl)-4-propan-2-yl-3,4-dihydro-1H-isoquinoline-7-carboxamide Chemical compound C(C)S(=O)(=O)C1=CC=C(CNC(=O)C2=CC=C3C(CN(CC3=C2)C2=NC=C(C=N2)N2CCOCC2)C(C)C)C=C1 JEOFWLXRHNLPPF-UHFFFAOYSA-N 0.000 claims 2
- NSSNUBJVGDXDDX-UHFFFAOYSA-N N-[(4-ethylsulfonylphenyl)methyl]-2-[(5-methylpyrimidin-2-yl)methyl]-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-6-carboxamide Chemical compound C(C)S(=O)(=O)C1=CC=C(CNC(=O)C=2C=C3CCN(C(C3=CC=2)C(C)C)CC2=NC=C(C=N2)C)C=C1 NSSNUBJVGDXDDX-UHFFFAOYSA-N 0.000 claims 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
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- RLUJEBLBTUVHBM-WFHLNLCJSA-N N-[(1R)-1-(4-ethylsulfonylphenyl)-2-hydroxyethyl]-1-methyl-7-[[4-(trifluoromethyl)cyclohexyl]methoxy]pyrrolo[2,3-c]pyridine-3-carboxamide Chemical compound C(C)S(=O)(=O)C1=CC=C(C=C1)[C@H](CO)NC(=O)C1=CN(C2=C(N=CC=C21)OCC1CCC(CC1)C(F)(F)F)C RLUJEBLBTUVHBM-WFHLNLCJSA-N 0.000 claims 1
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| DK3294713T5 (da) | 2015-05-15 | 2021-05-31 | Aurigene Discovery Tech Ltd | Substituerede tetrahydroquinolinonforbindelser som ror-gamma-modulatorer |
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| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| KR20200053481A (ko) | 2017-07-24 | 2020-05-18 | 비타이 파마슈티컬즈, 엘엘씨 | RORγ의 억제제 |
| CN109593068B (zh) * | 2017-09-30 | 2022-12-27 | 广东东阳光药业有限公司 | 一种RORγ抑制剂的中间体及其制备方法 |
| JPWO2019088057A1 (ja) * | 2017-10-31 | 2020-09-24 | 東レ株式会社 | アニリド誘導体及びその医薬用途 |
| CN111868036A (zh) | 2018-02-09 | 2020-10-30 | 美国政府健康与人类服务部 | 杂环p2y14受体拮抗剂 |
| WO2019167982A1 (ja) | 2018-02-28 | 2019-09-06 | 日本たばこ産業株式会社 | 飽和環縮合ジヒドロピリミジノン又はジヒドロトリアジノン化合物及びその医薬用途 |
| CN112601745B (zh) * | 2018-10-24 | 2023-06-27 | 上海和誉生物医药科技有限公司 | 一种氮杂芳基酰胺衍生物及其制备方法和应用 |
| MX2021005314A (es) | 2018-11-09 | 2021-08-24 | Vivace Therapeutics Inc | Compuestos biciclicos. |
| CN117800904A (zh) * | 2018-11-27 | 2024-04-02 | 正大天晴药业集团股份有限公司 | 含有磺酰基结构的RORγ抑制剂 |
| CN111484505B (zh) * | 2019-01-28 | 2022-11-15 | 正大天晴药业集团股份有限公司 | 一种双环RORγ抑制剂的盐酸盐结晶型 |
| PL3956033T3 (pl) * | 2019-04-16 | 2025-06-09 | Vivace Therapeutics, Inc. | Związki bicykliczne |
| AU2020290049A1 (en) * | 2019-06-12 | 2022-02-03 | Tmem16A Limited | Compounds for treating respiratory disease |
| WO2021047406A1 (zh) * | 2019-09-10 | 2021-03-18 | 四川科伦博泰生物医药股份有限公司 | 一种三并环类化合物，包含其的药物组合物，其制备方法及其用途 |
| CN112745268B (zh) * | 2019-10-31 | 2022-09-16 | 江苏恒瑞医药股份有限公司 | 苯并咪唑衍生物的晶型及制备方法 |
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