CA2689945A1 - 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors - Google Patents

Info

Publication number

CA2689945A1

CA2689945A1 CA2689945A CA2689945A CA2689945A1 CA 2689945 A1 CA2689945 A1 CA 2689945A1 CA 2689945 A CA2689945 A CA 2689945A CA 2689945 A CA2689945 A CA 2689945A CA 2689945 A1 CA2689945 A1 CA 2689945A1

Authority

CA

Canada

Prior art keywords

tetrahydro

pyrido

carbonyl

cyanocyclopropyl

cyclohexanecarboxamide

Prior art date

2007-06-26

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000003112 inhibitor Substances 0.000 title abstract description 34
• 102000005600 Cathepsins Human genes 0.000 title abstract description 5
• 108010084457 Cathepsins Proteins 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 167
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 108090000625 Cathepsin K Proteins 0.000 claims abstract description 12
• 102000004171 Cathepsin K Human genes 0.000 claims abstract description 12
• 102000005927 Cysteine Proteases Human genes 0.000 claims abstract description 9
• 108010005843 Cysteine Proteases Proteins 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• -1 OR3 Chemical group 0.000 claims description 111
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000002950 monocyclic group Chemical group 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 125000004122 cyclic group Chemical group 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 12
• 125000004169 (C1-C6) alkyl group Chemical group 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 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• HGEJGPHBRGISQP-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-hydroxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)O)NC1(C#N)CC1 HGEJGPHBRGISQP-HZPDHXFCSA-N 0.000 claims description 5
• 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 5
• 125000001931 aliphatic group Chemical group 0.000 claims description 5
• 210000000988 bone and bone Anatomy 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• JOLKNDYTTKAYRJ-DHIUTWEWSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-phenylmethoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(OCC=4C=CC=CC=4)=C3NC=2CC1)NC1(C#N)CC1 JOLKNDYTTKAYRJ-DHIUTWEWSA-N 0.000 claims description 4
• IJKUEXZNTYMXCX-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(9-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC=3C=CC=C(C=3C=2C1)S(=O)(=O)C)NC1(C#N)CC1 IJKUEXZNTYMXCX-HZPDHXFCSA-N 0.000 claims description 4
• UIVATUPCWVUVIM-UHFFFAOYSA-N 1-aminocyclopropane-1-carbonitrile Chemical compound N#CC1(N)CC1 UIVATUPCWVUVIM-UHFFFAOYSA-N 0.000 claims description 4
• 208000037848 Metastatic bone disease Diseases 0.000 claims description 4
• 208000001132 Osteoporosis Diseases 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• NZTAEEASJFTQGV-RTBURBONSA-N methyl 2-[2-[(1r,2r)-2-[(1-cyanocyclopropyl)carbamoyl]cyclohexanecarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetate Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2N(C3=CC=CC=C3C=2C1)CC(=O)OC)NC1(C#N)CC1 NZTAEEASJFTQGV-RTBURBONSA-N 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 230000000010 osteolytic effect Effects 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• FQEMSYXTXARKNW-HUUCEWRRSA-N (1R,2R)-N-(1-cyanocyclopropyl)-2-(4,4-difluoro-3,5-dioxa-12,16-diazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),2(6),7,10(15)-tetraene-12-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C3=CC=C4OC(OC4=C3NC=2CC1)(F)F)NC1(C#N)CC1 FQEMSYXTXARKNW-HUUCEWRRSA-N 0.000 claims description 3
• AQGUNNOFRISWLL-HZPDHXFCSA-N (1r,2r)-2-(6-bromo-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)-n-(1-cyanocyclopropyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)Br)NC1(C#N)CC1 AQGUNNOFRISWLL-HZPDHXFCSA-N 0.000 claims description 3
• GPRFWQGDRLPCOZ-HZPDHXFCSA-N (1r,2r)-2-(6-chloro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)-n-(1-cyanocyclopropyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)Cl)NC1(C#N)CC1 GPRFWQGDRLPCOZ-HZPDHXFCSA-N 0.000 claims description 3
• QYWIVCDSXQMNBT-HZPDHXFCSA-N (1r,2r)-2-(8-bromo-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)-n-(1-cyanocyclopropyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)Br)NC1(C#N)CC1 QYWIVCDSXQMNBT-HZPDHXFCSA-N 0.000 claims description 3
• XQUAGZLGGXLBJT-HZPDHXFCSA-N (1r,2r)-2-(8-chloro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)-n-(1-cyanocyclopropyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)Cl)NC1(C#N)CC1 XQUAGZLGGXLBJT-HZPDHXFCSA-N 0.000 claims description 3
• YOIFKTNHQMFUDH-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC=C3NC=2CC1)NC1(C#N)CC1 YOIFKTNHQMFUDH-IAGOWNOFSA-N 0.000 claims description 3
• HGJTURTZFKNELD-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)F)NC1(C#N)CC1 HGJTURTZFKNELD-HZPDHXFCSA-N 0.000 claims description 3
• XHSHPTAZQWFHLY-HUUCEWRRSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(9-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC=3C=CC=C(C=3C=2C1)F)NC1(C#N)CC1 XHSHPTAZQWFHLY-HUUCEWRRSA-N 0.000 claims description 3
• IBDSXHJUHUEWTN-WOJBJXKFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(spiro[1,3-dihydroisoquinoline-4,4'-piperidine]-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC2(CCNCC2)C2=CC=CC=C2C1)NC1(C#N)CC1 IBDSXHJUHUEWTN-WOJBJXKFSA-N 0.000 claims description 3
• YNQAAPNVYJAGJR-FGZHOGPDSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(2-morpholin-4-ylethoxy)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(OCCN4CCOCC4)=C3NC=2CC1)NC1(C#N)CC1 YNQAAPNVYJAGJR-FGZHOGPDSA-N 0.000 claims description 3
• XOHQNJVRFSPSEX-DHIUTWEWSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(2-piperidin-1-ylethoxy)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(OCCN4CCCCC4)=C3NC=2CC1)NC1(C#N)CC1 XOHQNJVRFSPSEX-DHIUTWEWSA-N 0.000 claims description 3
• JJVUOOITSZUPDJ-FGZHOGPDSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(2-pyrrolidin-1-ylethoxy)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(OCCN4CCCC4)=C3NC=2CC1)NC1(C#N)CC1 JJVUOOITSZUPDJ-FGZHOGPDSA-N 0.000 claims description 3
• LXMQSMICDCQAKZ-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(cyanomethoxy)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(OCC#N)=C3NC=2CC1)NC1(C#N)CC1 LXMQSMICDCQAKZ-QZTJIDSGSA-N 0.000 claims description 3
• QPRVCPZCVJWSIU-RTBURBONSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[8-[(dimethylamino)methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)CN(C)C)NC1(C#N)CC1 QPRVCPZCVJWSIU-RTBURBONSA-N 0.000 claims description 3
• VOEFTWPWXLUDTE-QZTJIDSGSA-N 2-[2-[(1r,2r)-2-[(1-cyanocyclopropyl)carbamoyl]cyclohexanecarbonyl]-3,4-dihydro-1h-pyrido[4,3-b]indol-5-yl]acetic acid Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2N(C3=CC=CC=C3C=2C1)CC(=O)O)NC1(C#N)CC1 VOEFTWPWXLUDTE-QZTJIDSGSA-N 0.000 claims description 3
• 208000020084 Bone disease Diseases 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• NFZALYIQHZXGAO-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(5-methylsulfonyl-3,4-dihydro-1h-pyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2N(C3=CC=CC=C3C=2C1)S(=O)(=O)C)NC1(C#N)CC1 NFZALYIQHZXGAO-QZTJIDSGSA-N 0.000 claims description 2
• GGFOMXPLOGYLIO-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-cyano-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC=2C3=CC=CC(=C3NC=2CC1)C#N)NC1(C#N)CC1 GGFOMXPLOGYLIO-QZTJIDSGSA-N 0.000 claims description 2
• DFWBUMFMCGXLEW-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)F)NC1(C#N)CC1 DFWBUMFMCGXLEW-HZPDHXFCSA-N 0.000 claims description 2
• ZJIQEAXGKFPTII-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-methoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OC)NC1(C#N)CC1 ZJIQEAXGKFPTII-IAGOWNOFSA-N 0.000 claims description 2
• DKGVOSFCHAMVHO-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)C)NC1(C#N)CC1 DKGVOSFCHAMVHO-QZTJIDSGSA-N 0.000 claims description 2
• IAKLMYSRERBHEH-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-methylsulfanyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)SC)NC1(C#N)CC1 IAKLMYSRERBHEH-IAGOWNOFSA-N 0.000 claims description 2
• ZASVBBCQLDAKGY-RTBURBONSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-propoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OCCC)NC1(C#N)CC1 ZASVBBCQLDAKGY-RTBURBONSA-N 0.000 claims description 2
• MIOKYZZTPMKVEG-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(7-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C3=CC=C(C=C3NC=2CC1)F)NC1(C#N)CC1 MIOKYZZTPMKVEG-IAGOWNOFSA-N 0.000 claims description 2
• YXSHPPFCJPOWHN-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(7-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C3=CC=C(C=C3NC=2CC1)S(=O)(=O)C)NC1(C#N)CC1 YXSHPPFCJPOWHN-QZTJIDSGSA-N 0.000 claims description 2
• IJZUBELGOVKMGO-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-fluoro-5-methyl-3,4-dihydro-1h-pyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2N(C3=CC=C(F)C=C3C=2C1)C)NC1(C#N)CC1 IJZUBELGOVKMGO-IAGOWNOFSA-N 0.000 claims description 2
• XPLAGGUHSFDLGW-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-fluoro-6-methoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=C(F)C=C(C=3NC=2CC1)OC)NC1(C#N)CC1 XPLAGGUHSFDLGW-HZPDHXFCSA-N 0.000 claims description 2
• LOXUZEQLPYVKQR-IAGOWNOFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)S(=O)(=O)C)NC1(C#N)CC1 LOXUZEQLPYVKQR-IAGOWNOFSA-N 0.000 claims description 2
• GXGPSYNIHMEZMU-RTBURBONSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-propan-2-yl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)C(C)C)NC1(C#N)CC1 GXGPSYNIHMEZMU-RTBURBONSA-N 0.000 claims description 2
• FTYBMFHPMPOHMA-WOJBJXKFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[5-(2-methoxyethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2N(C3=CC=CC=C3C=2C1)CCOC)NC1(C#N)CC1 FTYBMFHPMPOHMA-WOJBJXKFSA-N 0.000 claims description 2
• CVBJFMGLNXIPCO-NHCUHLMSSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[5-(cyclopropylmethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](CCCC1)C(=O)N1CC2=C(N(C3=CC=CC=C32)CC2CC2)CC1)NC1(C#N)CC1 CVBJFMGLNXIPCO-NHCUHLMSSA-N 0.000 claims description 2
• VGFYFZDIJPOBAY-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(trifluoromethoxy)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OC(F)(F)F)NC1(C#N)CC1 VGFYFZDIJPOBAY-HZPDHXFCSA-N 0.000 claims description 2
• YRLSAGVJGNJNON-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-(trifluoromethyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)C(F)(F)F)NC1(C#N)CC1 YRLSAGVJGNJNON-HZPDHXFCSA-N 0.000 claims description 2
• ACVZLIMCUJMGLB-WOJBJXKFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-[2-(dimethylamino)ethoxy]-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OCCN(C)C)NC1(C#N)CC1 ACVZLIMCUJMGLB-WOJBJXKFSA-N 0.000 claims description 2
• DQIAQOULNLHSCO-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[8-(trifluoromethyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)C(F)(F)F)NC1(C#N)CC1 DQIAQOULNLHSCO-HZPDHXFCSA-N 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
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