CA2689945A1 - 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors - Google Patents
1-cyanocyclopropyl-derivatives as cathepsin k inhibitors Download PDFInfo
- 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
- 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
- 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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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D—HETEROCYCLIC COMPOUNDS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94617807P | 2007-06-26 | 2007-06-26 | |
| US60/946,178 | 2007-06-26 | ||
| US4284008P | 2008-04-07 | 2008-04-07 | |
| US61/042,840 | 2008-04-07 | ||
| PCT/GB2008/050486 WO2009001129A1 (en) | 2007-06-26 | 2008-06-24 | 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2689945A1 true CA2689945A1 (en) | 2008-12-31 |
Family
ID=39761131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2689945A Abandoned CA2689945A1 (en) | 2007-06-26 | 2008-06-24 | 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors |
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| US (1) | US8008279B2 (enExample) |
| EP (1) | EP2170879B1 (enExample) |
| JP (1) | JP2010531344A (enExample) |
| KR (1) | KR20100039862A (enExample) |
| CN (1) | CN101687864A (enExample) |
| AR (1) | AR067156A1 (enExample) |
| AU (1) | AU2008269513B2 (enExample) |
| BR (1) | BRPI0813306A2 (enExample) |
| CA (1) | CA2689945A1 (enExample) |
| CL (1) | CL2008001899A1 (enExample) |
| CO (1) | CO6251264A2 (enExample) |
| EC (1) | ECSP109882A (enExample) |
| IL (1) | IL202519A0 (enExample) |
| NZ (1) | NZ581719A (enExample) |
| PE (1) | PE20090841A1 (enExample) |
| RU (1) | RU2470023C2 (enExample) |
| TW (1) | TW200911806A (enExample) |
| UY (1) | UY31180A1 (enExample) |
| WO (1) | WO2009001129A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2476680B1 (en) | 2008-01-11 | 2014-08-27 | Albany Molecular Research, Inc. | (1-Azinone)-Substituted Pyridoindoles |
| RU2544856C2 (ru) * | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| JP5666036B2 (ja) * | 2008-01-25 | 2015-02-04 | メディベイション テクノロジーズ， インコーポレイテッド | 新規２，３，４，５−テトラヒドロ−１Ｈ−ピリド［４，３−ｂ］インドール化合物およびその使用方法 |
| TW201018694A (en) | 2008-09-29 | 2010-05-16 | Abbott Lab | Indole and indoline derivatives and methods of use thereof |
| US9625475B2 (en) | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| JP2012512871A (ja) * | 2008-12-18 | 2012-06-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 三環式アザインドール |
| US7893099B2 (en) * | 2009-06-11 | 2011-02-22 | Hoffman-La Roche Inc. | Cyclopentane derivatives |
| US9073925B2 (en) * | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003007A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| US8618299B2 (en) * | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| WO2011049917A1 (en) * | 2009-10-21 | 2011-04-28 | Boehringer Ingelheim International Gmbh | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| US8927550B2 (en) | 2009-10-27 | 2015-01-06 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds as CCR1 receptor antagonists |
| CN104592233A (zh) | 2009-12-17 | 2015-05-06 | Abbvie公司 | 用于治疗神经变性和神经精神紊乱的桥头胺环稠合吲哚和二氢吲哚 |
| WO2011084433A2 (en) | 2009-12-17 | 2011-07-14 | Abbott Laboratories | Aza-bridged ring-fused indoles and indolines |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| IN2013MN01699A (enExample) | 2011-02-18 | 2015-06-12 | Medivation Technologies Inc | |
| EP2802591B1 (en) * | 2012-01-11 | 2016-03-16 | F.Hoffmann-La Roche Ag | Macrocyclic amides as protease inhibitors |
| CN103086923B (zh) * | 2013-01-21 | 2014-04-23 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在治疗骨质疏松症方面的应用 |
| CA2923272A1 (en) * | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Cathepsin cysteine protease inhibitors |
| WO2016027285A2 (en) * | 2014-08-22 | 2016-02-25 | Alkem Laboratories Ltd. | Bicyclic heteroaryl amides as cathepsin cysteine protease inhibitors |
| CN105837479B (zh) * | 2016-04-05 | 2017-10-27 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在制备治疗骨关节炎药物中的应用 |
| EP3600451A4 (en) * | 2017-03-29 | 2021-04-14 | Minerva Biotechnologies Corporation | MEANS FOR STEM CELL DIFFERENTIATION AND CANCER TREATMENT |
| EP4467544A1 (en) * | 2022-01-21 | 2024-11-27 | Shandong New Time Pharmaceutical Co., Ltd. | Cathepsin k inhibitor, and preparation method therefor and use thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2264937T3 (es) * | 1999-07-30 | 2007-02-01 | Boehringer Ingelheim Pharmaceuticals Inc. | Nuevos compuestos derivados de succinato, utiles como inhibidores de cisteina-proteasa. |
| CA2396257A1 (en) * | 2000-01-06 | 2001-07-12 | Merck Frosst Canada & Co./Merck Frosst Canada & Cie | Novel compounds and compositions as protease inhibitors |
| WO2001068645A2 (en) | 2000-03-15 | 2001-09-20 | Axys Pharmaceuticals, Inc. | N-cyanomethylcarboxamides and their use as protease inhibitors |
| WO2002069901A2 (en) | 2001-03-02 | 2002-09-12 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| RU2278863C2 (ru) * | 2001-08-10 | 2006-06-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция и способ ингибирования активности катепсина s |
| KR20050044660A (ko) * | 2001-12-04 | 2005-05-12 | 에프. 호프만-라 로슈 아게 | 치환된 2-아미노-사이클로알칸카복스아마이드 및 시스테인프로테아제 저해제로서의 이의 용도 |
| SE0201977D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| SE0203712D0 (sv) | 2002-12-13 | 2002-12-13 | Astrazeneca Ab | Novel compounds |
| US7109339B2 (en) | 2002-12-19 | 2006-09-19 | Bristol-Myers Squibb Company | Substituted tricyclic gamma-carbolines as serotonin receptor agonists and antagonists |
-
2008
- 2008-06-24 JP JP2010514135A patent/JP2010531344A/ja active Pending
- 2008-06-24 KR KR1020107001848A patent/KR20100039862A/ko not_active Withdrawn
- 2008-06-24 CN CN200880021955A patent/CN101687864A/zh active Pending
- 2008-06-24 EP EP08776161A patent/EP2170879B1/en active Active
- 2008-06-24 NZ NZ581719A patent/NZ581719A/en not_active IP Right Cessation
- 2008-06-24 WO PCT/GB2008/050486 patent/WO2009001129A1/en not_active Ceased
- 2008-06-24 AU AU2008269513A patent/AU2008269513B2/en not_active Ceased
- 2008-06-24 BR BRPI0813306A patent/BRPI0813306A2/pt not_active IP Right Cessation
- 2008-06-24 RU RU2010101279/04A patent/RU2470023C2/ru not_active IP Right Cessation
- 2008-06-24 CA CA2689945A patent/CA2689945A1/en not_active Abandoned
- 2008-06-25 TW TW097123686A patent/TW200911806A/zh unknown
- 2008-06-25 US US12/145,855 patent/US8008279B2/en not_active Expired - Fee Related
- 2008-06-25 UY UY31180A patent/UY31180A1/es not_active Application Discontinuation
- 2008-06-25 AR ARP080102722A patent/AR067156A1/es not_active Application Discontinuation
- 2008-06-26 CL CL2008001899A patent/CL2008001899A1/es unknown
- 2008-06-26 PE PE2008001087A patent/PE20090841A1/es not_active Application Discontinuation
-
2009
- 2009-12-03 IL IL202519A patent/IL202519A0/en unknown
- 2009-12-22 CO CO09146663A patent/CO6251264A2/es not_active Application Discontinuation
-
2010
- 2010-01-15 EC EC2010009882A patent/ECSP109882A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20090012077A1 (en) | 2009-01-08 |
| NZ581719A (en) | 2011-08-26 |
| JP2010531344A (ja) | 2010-09-24 |
| AU2008269513A1 (en) | 2008-12-31 |
| WO2009001129A9 (en) | 2010-02-04 |
| EP2170879A1 (en) | 2010-04-07 |
| IL202519A0 (en) | 2010-06-30 |
| WO2009001129A1 (en) | 2008-12-31 |
| RU2010101279A (ru) | 2011-08-10 |
| UY31180A1 (es) | 2009-01-30 |
| CN101687864A (zh) | 2010-03-31 |
| CL2008001899A1 (es) | 2009-07-17 |
| RU2470023C2 (ru) | 2012-12-20 |
| AR067156A1 (es) | 2009-09-30 |
| KR20100039862A (ko) | 2010-04-16 |
| ECSP109882A (es) | 2010-02-26 |
| EP2170879B1 (en) | 2013-01-16 |
| BRPI0813306A2 (pt) | 2017-05-16 |
| PE20090841A1 (es) | 2009-08-02 |
| TW200911806A (en) | 2009-03-16 |
| CO6251264A2 (es) | 2011-02-21 |
| AU2008269513B2 (en) | 2011-06-16 |
| US8008279B2 (en) | 2011-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140625 |