JP4931794B2 - 縮合環アザデカリン糖質コルチコイド受容体モジュレーター - Google Patents

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Publication number

JP4931794B2

JP4931794B2 JP2007503030A JP2007503030A JP4931794B2 JP 4931794 B2 JP4931794 B2 JP 4931794B2 JP 2007503030 A JP2007503030 A JP 2007503030A JP 2007503030 A JP2007503030 A JP 2007503030A JP 4931794 B2 JP4931794 B2 JP 4931794B2

Authority

JP

Japan

Prior art keywords

fluoro

phenyl

hexahydro

cyclopenta

triaza

Prior art date

2004-03-09

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.)

Expired - Fee Related

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• 229940117965 Glucocorticoid receptor modulator Drugs 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 362
• -1 2-methoxy-ethoxymethyl Chemical group 0.000 claims description 185
• 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 167
• 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 166
• 125000000217 alkyl group Chemical group 0.000 claims description 110
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 102
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 94
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 93
• 229910052739 hydrogen Inorganic materials 0.000 claims description 77
• 239000001257 hydrogen Substances 0.000 claims description 77
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
• 150000002431 hydrogen Chemical class 0.000 claims description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 59
• 239000000203 mixture Substances 0.000 claims description 53
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 208000028017 Psychotic disease Diseases 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 208000024714 major depressive disease Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 206010012218 Delirium Diseases 0.000 claims description 3
• 206010012289 Dementia Diseases 0.000 claims description 3
• 208000013200 Stress disease Diseases 0.000 claims description 3
• 230000003042 antagnostic effect Effects 0.000 claims description 3
• 230000000561 anti-psychotic effect Effects 0.000 claims description 3
• 230000004584 weight gain Effects 0.000 claims description 3
• 235000019786 weight gain Nutrition 0.000 claims description 3
• RROWGHHVPJSOMA-HHHXNRCGSA-N (4ar)-1-(4-fluorophenyl)-4a-(2-methoxyethoxymethyl)-6-(4-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COCCOC)N(S(=O)(=O)C=3C=CC(C)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 RROWGHHVPJSOMA-HHHXNRCGSA-N 0.000 claims description 2
• RGLSTIMKKNKDQQ-RUZDIDTESA-N (4ar)-1-(4-fluorophenyl)-4a-(methoxymethyl)-6-(4-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COC)N(S(=O)(=O)C=3C=CC(C)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 RGLSTIMKKNKDQQ-RUZDIDTESA-N 0.000 claims description 2
• IQSFLWKMHDHZDX-AREMUKBSSA-N (4ar)-1-(4-fluorophenyl)-6-(4-fluorophenyl)sulfonyl-4a-(2-methoxyethoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COCCOC)N(S(=O)(=O)C=3C=CC(F)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 IQSFLWKMHDHZDX-AREMUKBSSA-N 0.000 claims description 2
• FYVABXFXVMYQBW-XMMPIXPASA-N (4ar)-1-(4-fluorophenyl)-6-(4-fluorophenyl)sulfonyl-4a-(methoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COC)N(S(=O)(=O)C=3C=CC(F)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 FYVABXFXVMYQBW-XMMPIXPASA-N 0.000 claims description 2
• OMKDFVUMRKROMY-SSEXGKCCSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(2-methoxyethoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COCCOC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 OMKDFVUMRKROMY-SSEXGKCCSA-N 0.000 claims description 2
• AKWLCDVWCXYOIV-GDLZYMKVSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(2-methoxyethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)CCOC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 AKWLCDVWCXYOIV-GDLZYMKVSA-N 0.000 claims description 2
• KIQOZAVETWJRMW-JGCGQSQUSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(2-pyrrolidin-1-ylethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@]2(CCN3CCCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 KIQOZAVETWJRMW-JGCGQSQUSA-N 0.000 claims description 2
• BIEOWMRLZMSLDE-WJOKGBTCSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(3-methoxypropoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COCCCOC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 BIEOWMRLZMSLDE-WJOKGBTCSA-N 0.000 claims description 2
• MQLYVQIGSYLRLH-MUUNZHRXSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(methoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 MQLYVQIGSYLRLH-MUUNZHRXSA-N 0.000 claims description 2
• QNUVKFNORIMQDH-LJAQVGFWSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-n,n-dimethyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline-4a-carboxamide Chemical compound C([C@]1(C2)C(=O)N(C)C)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 QNUVKFNORIMQDH-LJAQVGFWSA-N 0.000 claims description 2
• KEWIBZFESTXMFD-GDLZYMKVSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-4a-(ethoxymethyl)-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COCC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 KEWIBZFESTXMFD-GDLZYMKVSA-N 0.000 claims description 2
• WFEKSVMEAMADBH-LJAQVGFWSA-N (4ar)-6-(4-tert-butylphenyl)sulfonyl-n-ethyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline-4a-carboxamide Chemical compound C([C@]1(C2)C(=O)NCC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 WFEKSVMEAMADBH-LJAQVGFWSA-N 0.000 claims description 2
• IKRBNDCVQKJNNL-XMMPIXPASA-N (4ar)-6-(benzenesulfonyl)-1-(4-fluorophenyl)-4a-(methoxymethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)COC)N(S(=O)(=O)C=3C=CC=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 IKRBNDCVQKJNNL-XMMPIXPASA-N 0.000 claims description 2
• ZSXZJDQSKIQKLR-XMMPIXPASA-N (4as)-1-(4-fluorophenyl)-4a-methyl-6-(2-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C[C@@]2(C)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 ZSXZJDQSKIQKLR-XMMPIXPASA-N 0.000 claims description 2
• DVDKEBCTGVWNBS-XMMPIXPASA-N (4as)-1-(4-fluorophenyl)-4a-methyl-6-(4-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C[C@@]2(C)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 DVDKEBCTGVWNBS-XMMPIXPASA-N 0.000 claims description 2
• KOSPKCVWAQOJPK-HSZRJFAPSA-N (4as)-1-(4-fluorophenyl)-6-(2-fluorophenyl)sulfonyl-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)C)N(S(=O)(=O)C=3C(=CC=CC=3)F)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 KOSPKCVWAQOJPK-HSZRJFAPSA-N 0.000 claims description 2
• OBJXJRIGGFJBSZ-HSZRJFAPSA-N (4as)-1-(4-fluorophenyl)-6-(4-fluorophenyl)sulfonyl-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C([C@]1(C2)C)N(S(=O)(=O)C=3C=CC(F)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 OBJXJRIGGFJBSZ-HSZRJFAPSA-N 0.000 claims description 2
• SWPDABSIHZBYLE-LJAQVGFWSA-N (4as)-1-(4-fluorophenyl)-6-(4-methoxyphenyl)sulfonyl-4a-(piperidin-1-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCCCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 SWPDABSIHZBYLE-LJAQVGFWSA-N 0.000 claims description 2
• PYLUBHUVEXFGDV-XMMPIXPASA-N (4as)-1-(4-fluorophenyl)-6-(4-methoxyphenyl)sulfonyl-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C[C@@]2(C)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 PYLUBHUVEXFGDV-XMMPIXPASA-N 0.000 claims description 2
• VVDJUYIKTOCGCI-NDEPHWFRSA-N (4as)-1-(4-fluorophenyl)-6-(4-methylphenyl)sulfonyl-4a-(pyrrolidin-1-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 VVDJUYIKTOCGCI-NDEPHWFRSA-N 0.000 claims description 2
• XUHSVEXCUONJNQ-PMERELPUSA-N (4as)-4a-(azetidin-1-ylmethyl)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 XUHSVEXCUONJNQ-PMERELPUSA-N 0.000 claims description 2
• DOLSDPWCNNSYNQ-YTTGMZPUSA-N (4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-(piperidin-1-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCCCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 DOLSDPWCNNSYNQ-YTTGMZPUSA-N 0.000 claims description 2
• CRNBLUOPQLCADK-YTTGMZPUSA-N (4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-[(4-methylpiperazin-1-yl)methyl]-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1CN(C)CCN1C[C@@]1(CN(CC2)S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)C2=CC(N(N=C2)C=3C=CC(F)=CC=3)=C2C1 CRNBLUOPQLCADK-YTTGMZPUSA-N 0.000 claims description 2
• OIKFLZJCOASDMC-HHHXNRCGSA-N (4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@]2(C)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 OIKFLZJCOASDMC-HHHXNRCGSA-N 0.000 claims description 2
• MXCCVPFKPUFGLO-NDEPHWFRSA-N (4as)-6-(benzenesulfonyl)-1-(4-fluorophenyl)-4a-(piperidin-1-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(F)=CC=C1N1C(C=C2CCN(C[C@@]2(CN2CCCCC2)C2)S(=O)(=O)C=3C=CC=CC=3)=C2C=N1 MXCCVPFKPUFGLO-NDEPHWFRSA-N 0.000 claims description 2
• JUBJYIBDDUCCTO-MHZLTWQESA-N (4as)-6-(benzenesulfonyl)-1-(4-fluorophenyl)-4a-(pyrrolidin-1-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinoline Chemical compound C1=CC(F)=CC=C1N1C(C=C2CCN(C[C@@]2(CN2CCCC2)C2)S(=O)(=O)C=3C=CC=CC=3)=C2C=N1 JUBJYIBDDUCCTO-MHZLTWQESA-N 0.000 claims description 2
• YCMIKRUICRPTTI-ACEFPKFPSA-N 1-[(4ar)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]propan-1-ol Chemical compound C([C@]1(C2)C(O)CC)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 YCMIKRUICRPTTI-ACEFPKFPSA-N 0.000 claims description 2
• IUXAJJWCPLUGKF-VWLOTQADSA-N 1-[(4as)-1-(4-fluorophenyl)-6-(4-fluorophenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]-n,n-dimethylmethanamine Chemical compound C([C@]1(C2)CN(C)C)N(S(=O)(=O)C=3C=CC(F)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 IUXAJJWCPLUGKF-VWLOTQADSA-N 0.000 claims description 2
• HPMBUGNAXNQIFW-SANMLTNESA-N 1-[(4as)-1-(4-fluorophenyl)-6-(4-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]-n,n-dimethylmethanamine Chemical compound C([C@]1(C2)CN(C)C)N(S(=O)(=O)C=3C=CC(C)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 HPMBUGNAXNQIFW-SANMLTNESA-N 0.000 claims description 2
• WCIYRUISLVKIKJ-LJAQVGFWSA-N 1-[(4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]-n,n-dimethylmethanamine Chemical compound C([C@]1(C2)CN(C)C)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 WCIYRUISLVKIKJ-LJAQVGFWSA-N 0.000 claims description 2
• IJBNOVDOGMDLHU-PMERELPUSA-N 2-[[(4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]methyl-methylamino]ethanol Chemical compound C([C@]1(C2)CN(CCO)C)N(S(=O)(=O)C=3C=CC(=CC=3)C(C)(C)C)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 IJBNOVDOGMDLHU-PMERELPUSA-N 0.000 claims description 2
• OHDRZPOIXFZQQK-HHHXNRCGSA-N 4-[4-[[(4as)-1-(4-fluorophenyl)-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-6-yl]sulfonyl]phenyl]morpholine Chemical compound C([C@]1(C2)C)N(S(=O)(=O)C=3C=CC(=CC=3)N3CCOCC3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 OHDRZPOIXFZQQK-HHHXNRCGSA-N 0.000 claims description 2
• CITOSWBMTRNWJZ-NDEPHWFRSA-N 4-[[(4as)-1-(4-fluorophenyl)-4a-(morpholin-4-ylmethyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-6-yl]sulfonyl]benzonitrile Chemical compound C1=CC(F)=CC=C1N1C(C=C2CCN(C[C@@]2(CN2CCOCC2)C2)S(=O)(=O)C=3C=CC(=CC=3)C#N)=C2C=N1 CITOSWBMTRNWJZ-NDEPHWFRSA-N 0.000 claims description 2
• JRONILRFTYPGNQ-HSZRJFAPSA-N 4-[[(4as)-1-(4-fluorophenyl)-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-6-yl]sulfonyl]aniline Chemical compound C([C@]1(C2)C)N(S(=O)(=O)C=3C=CC(N)=CC=3)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 JRONILRFTYPGNQ-HSZRJFAPSA-N 0.000 claims description 2
• ZGAMRUITCKEAIH-XMMPIXPASA-N 4-[[(4as)-1-(4-fluorophenyl)-4a-methyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-6-yl]sulfonyl]benzonitrile Chemical compound C([C@]1(C2)C)N(S(=O)(=O)C=3C=CC(=CC=3)C#N)CCC1=CC1=C2C=NN1C1=CC=C(F)C=C1 ZGAMRUITCKEAIH-XMMPIXPASA-N 0.000 claims description 2
• ZTMKXTDUQBGLBN-MHZLTWQESA-N 4-[[(4as)-1-(4-fluorophenyl)-6-(2-fluorophenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]methyl]morpholine Chemical compound C1=CC(F)=CC=C1N1C(C=C2CCN(C[C@@]2(CN2CCOCC2)C2)S(=O)(=O)C=3C(=CC=CC=3)F)=C2C=N1 ZTMKXTDUQBGLBN-MHZLTWQESA-N 0.000 claims description 2
• YNLHNMHDKAZISS-NDEPHWFRSA-N 4-[[(4as)-1-(4-fluorophenyl)-6-(2-methylphenyl)sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]methyl]morpholine Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCOCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 YNLHNMHDKAZISS-NDEPHWFRSA-N 0.000 claims description 2
• IWSLNGSSRFNXNI-MHZLTWQESA-N 4-[[(4as)-1-(4-fluorophenyl)-6-[4-(trifluoromethyl)phenyl]sulfonyl-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]methyl]morpholine Chemical compound C1=CC(F)=CC=C1N1C(C=C2CCN(C[C@@]2(CN2CCOCC2)C2)S(=O)(=O)C=3C=CC(=CC=3)C(F)(F)F)=C2C=N1 IWSLNGSSRFNXNI-MHZLTWQESA-N 0.000 claims description 2
• GGJJEBNVSUSMAO-HKBQPEDESA-N 4-[[(4as)-6-(4-tert-butylphenyl)sulfonyl-1-(4-fluorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-g]isoquinolin-4a-yl]methyl]morpholine Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C[C@@]2(CN3CCOCC3)CC(C=NN3C=4C=CC(F)=CC=4)=C3C=C2CC1 GGJJEBNVSUSMAO-HKBQPEDESA-N 0.000 claims description 2
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