JP2018135335A5 - - Google Patents
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- JP2018135335A5 JP2018135335A5 JP2018042934A JP2018042934A JP2018135335A5 JP 2018135335 A5 JP2018135335 A5 JP 2018135335A5 JP 2018042934 A JP2018042934 A JP 2018042934A JP 2018042934 A JP2018042934 A JP 2018042934A JP 2018135335 A5 JP2018135335 A5 JP 2018135335A5
- Authority
- JP
- Japan
- Prior art keywords
- tetramethyl
- optionally substituted
- decahydronaphthalen
- carbonyl
- formula
- 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 51
- 150000003839 salts Chemical class 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 25
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- -1 3-methoxy-5-methylphenyl Chemical group 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229960001755 resorcinol Drugs 0.000 claims 2
- QLDWKJIFTFHGHX-IBRRDTTFSA-N (1r,2r,8as)-1-[(3,5-dimethoxyphenyl)sulfonylmethyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(OC)=CC(S(=O)(=O)C[C@@H]2[C@]3(CCCC(C)(C)C3CC[C@]2(O)C)C)=C1 QLDWKJIFTFHGHX-IBRRDTTFSA-N 0.000 claims 1
- BKARYMOMZUJSFB-PABCKOPISA-N (1s,2r,4as,8as)-1-[(3,5-dimethoxyphenoxy)methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(OC)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 BKARYMOMZUJSFB-PABCKOPISA-N 0.000 claims 1
- FNOGLPRPGFTFMV-PABCKOPISA-N (1s,2r,4as,8as)-1-[(3-methoxy-5-methylphenoxy)methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(C)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 FNOGLPRPGFTFMV-PABCKOPISA-N 0.000 claims 1
- ORLLMRPTJQLBAX-XTMUJBCUSA-N (1s,2r,4as,8as)-1-[[3,5-bis(phenylmethoxy)phenoxy]methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound C([C@@H]1[C@@]2(C)CCCC([C@@H]2CC[C@]1(O)C)(C)C)OC(C=C(OCC=1C=CC=CC=1)C=1)=CC=1OCC1=CC=CC=C1 ORLLMRPTJQLBAX-XTMUJBCUSA-N 0.000 claims 1
- CWDHVPLOTPEQSW-AEZNDSDVSA-N (1s,2r,4as,8as)-1-[[3,5-di(propan-2-yloxy)phenoxy]methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound CC(C)OC1=CC(OC(C)C)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 CWDHVPLOTPEQSW-AEZNDSDVSA-N 0.000 claims 1
- QHRUGZSRIZHZSY-QEZVKXNPSA-N (3r,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-3,4,5,6,7,8a-hexahydro-1h-naphthalen-2-one Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC(=O)[C@@H]2C)C)=C1 QHRUGZSRIZHZSY-QEZVKXNPSA-N 0.000 claims 1
- LYBMRSVSQINEPA-JSXJTULDSA-N (3r,4s,4as,8as)-4-(3-methoxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-3,4,5,6,7,8a-hexahydro-1h-naphthalen-2-one Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC(=O)[C@@H]2C)C)=C1 LYBMRSVSQINEPA-JSXJTULDSA-N 0.000 claims 1
- XCCFFIAVOJBCIV-CIHDNBESSA-N (3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalene-2-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC([C@H]1C)C(N)=O)C1=CC(C)=CC(O)=C1 XCCFFIAVOJBCIV-CIHDNBESSA-N 0.000 claims 1
- LJQNJHVERXEDIW-CIHDNBESSA-N (3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalene-2-carboxylic acid Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC([C@H]1C)C(O)=O)C1=CC(C)=CC(O)=C1 LJQNJHVERXEDIW-CIHDNBESSA-N 0.000 claims 1
- VQLJHBMROIASBP-DZVNEVJTSA-N (3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-3,4,5,6,7,8a-hexahydro-1h-naphthalen-2-one Chemical compound O=C([C@H]1[C@@H](C(C[C@H]2C(C)(C)CCC[C@@]21C)=O)C)C1=CC(C)=CC(O)=C1 VQLJHBMROIASBP-DZVNEVJTSA-N 0.000 claims 1
- XAGILEYKSRQVCV-AQLHERBPSA-N (3s,4s,4as,8as)-4-(3-methoxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalene-2-carboxamide Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC([C@H]2C)C(N)=O)C)=C1 XAGILEYKSRQVCV-AQLHERBPSA-N 0.000 claims 1
- JQEOKNVDTBWMSO-AQLHERBPSA-N (3s,4s,4as,8as)-4-(3-methoxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalene-2-carboxylic acid Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC([C@H]2C)C(O)=O)C)=C1 JQEOKNVDTBWMSO-AQLHERBPSA-N 0.000 claims 1
- SQSHQGQQNWXZKJ-CVDCTZTESA-N (4as,8as)-n-(3,5-dimethoxyphenyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxamide Chemical compound COC1=CC(OC)=CC(NC(=O)C=2[C@]3(CCCC(C)(C)[C@@H]3CCC=2C)C)=C1 SQSHQGQQNWXZKJ-CVDCTZTESA-N 0.000 claims 1
- FHRCOOJOOITDEJ-AVRDEDQJSA-N (4as,8as)-n-(3-hydroxy-5-methoxyphenyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxamide Chemical compound COC1=CC(O)=CC(NC(=O)C=2[C@]3(CCCC(C)(C)[C@@H]3CCC=2C)C)=C1 FHRCOOJOOITDEJ-AVRDEDQJSA-N 0.000 claims 1
- NQIZWULAGUBAPT-QNWVGRARSA-N (4as,8s,8as)-8-[(3-methoxy-5-methylphenyl)methyl]-4,4,8a-trimethyl-7-methylidene-2,3,4a,5,6,8-hexahydro-1h-naphthalene Chemical compound COC1=CC(C)=CC(C[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CCC2=C)C)=C1 NQIZWULAGUBAPT-QNWVGRARSA-N 0.000 claims 1
- CESSZOYZTWOWLE-HSWOKNGBSA-N (4s,4as,8as)-4-(3-methoxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalene-2-carbonitrile Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC(C2C)C#N)C)=C1 CESSZOYZTWOWLE-HSWOKNGBSA-N 0.000 claims 1
- NZPVIWLCAQHHTC-SVXRBACFSA-N (4s,4as,8as)-4-[(3-methoxy-5-methylphenoxy)methyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-ol Chemical compound COC1=CC(C)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC(O)C2C)C)=C1 NZPVIWLCAQHHTC-SVXRBACFSA-N 0.000 claims 1
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 claims 1
- UPNUCVIWAOWCGQ-BOIVJVEXSA-N 1-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-ethylurea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)NCC)C1=CC(O)=CC(O)=C1 UPNUCVIWAOWCGQ-BOIVJVEXSA-N 0.000 claims 1
- QTUCEDJHABSION-JGWYQGNSSA-N 1-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-methoxyurea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)NOC)C1=CC(O)=CC(O)=C1 QTUCEDJHABSION-JGWYQGNSSA-N 0.000 claims 1
- ZZMYKJNBAICTFC-JGWYQGNSSA-N 1-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-methylthiourea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=S)NC)C1=CC(O)=CC(O)=C1 ZZMYKJNBAICTFC-JGWYQGNSSA-N 0.000 claims 1
- WMKGYBCAVKFIRL-JGWYQGNSSA-N 1-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-methylurea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)NC)C1=CC(O)=CC(O)=C1 WMKGYBCAVKFIRL-JGWYQGNSSA-N 0.000 claims 1
- NXYBCINETOBEKR-LZITZJIASA-N 1-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-pyridin-3-ylurea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)NC=1C=NC=CC=1)C1=CC(O)=CC(O)=C1 NXYBCINETOBEKR-LZITZJIASA-N 0.000 claims 1
- KSHKBESIKRAVOY-ODFMKGCVSA-N 1-[(2r,3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-pyridin-3-ylurea Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)NC=1C=NC=CC=1)C1=CC(C)=CC(O)=C1 KSHKBESIKRAVOY-ODFMKGCVSA-N 0.000 claims 1
- WMCPGHLETHURJD-OFWOVDFZSA-N 2-[(1s,2r,3r,4as,8ar)-3-bromo-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-n-(3,5-dihydroxyphenyl)-n-methylacetamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@@H](Br)[C@@H]1C)C(=O)N(C)C1=CC(O)=CC(O)=C1 WMCPGHLETHURJD-OFWOVDFZSA-N 0.000 claims 1
- RKVQVNXMJLMUJF-SXWKCWPCSA-N 2-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-n-(3,5-dihydroxyphenyl)-n-methylacetamide Chemical compound C([C@@H]1[C@]2(CCCC(C)(C)[C@@H]2CC=C1C)C)C(=O)N(C)C1=CC(O)=CC(O)=C1 RKVQVNXMJLMUJF-SXWKCWPCSA-N 0.000 claims 1
- UCLQUKNXAJZTGI-JDVRMBDFSA-N 2-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]guanidine Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)N=C(N)N)C1=CC(O)=CC(O)=C1 UCLQUKNXAJZTGI-JDVRMBDFSA-N 0.000 claims 1
- WQMQTYZZMFCUEG-HHLMGXLOSA-N 2-[(2r,3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]guanidine Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)N=C(N)N)C1=CC(C)=CC(O)=C1 WQMQTYZZMFCUEG-HHLMGXLOSA-N 0.000 claims 1
- YNPQNHDRUCNWFT-INJSUYMTSA-N 2-[[2-[[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]amino]-2-oxoethyl]sulfamoyl]benzoic acid Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)CNS(=O)(=O)C=1C(=CC=CC=1)C(O)=O)C1=CC(O)=CC(O)=C1 YNPQNHDRUCNWFT-INJSUYMTSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- MWCNNMDTZBKQHW-JAXLGGSGSA-N 3-[[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methoxy]-5-methylphenol Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC=C1C)OC1=CC(C)=CC(O)=C1 MWCNNMDTZBKQHW-JAXLGGSGSA-N 0.000 claims 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- DJXXVQJIZQQOIV-ANGWPXEHSA-N FC1=CC=C(C(=O)NCC[C@H]2[C@@H]([C@@H](CC3C(CCC[C@]23C)(C)C)N2CCN(CC2)C)C)C=C1 Chemical compound FC1=CC=C(C(=O)NCC[C@H]2[C@@H]([C@@H](CC3C(CCC[C@]23C)(C)C)N2CCN(CC2)C)C)C=C1 DJXXVQJIZQQOIV-ANGWPXEHSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- FCAFUKGBIMGKEZ-VOFXCDAESA-N [(1r,2r,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 FCAFUKGBIMGKEZ-VOFXCDAESA-N 0.000 claims 1
- CMJCENLXPDAELS-VOFXCDAESA-N [(1r,2r,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 CMJCENLXPDAELS-VOFXCDAESA-N 0.000 claims 1
- CFWXECSSWZJSRE-AWWSKVOZSA-N [(1r,3r,4as,8as)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](O)C2=C)C)=C1 CFWXECSSWZJSRE-AWWSKVOZSA-N 0.000 claims 1
- NVWINSLPDRWUTN-AZSTXNOHSA-N [(1s,2r,3r,4as,8as)-3-hydroxy-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](O)[C@@H]2C)C)=C1 NVWINSLPDRWUTN-AZSTXNOHSA-N 0.000 claims 1
- SKOWRUZBSSZIJJ-ZSXCXTCJSA-N [(1s,2r,3r,4as,8as)-3-hydroxy-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](O)[C@@H]2C)C)=C1 SKOWRUZBSSZIJJ-ZSXCXTCJSA-N 0.000 claims 1
- KSEANNCWEPGWEE-YAEZTRJGSA-N [(1s,2r,3s,4as,8as)-2,5,5,8a-tetramethyl-3-(1,2,4-triazol-1-ylmethyl)-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound C([C@@H]1[C@H]([C@@H]([C@@]2(C)CCCC(C)(C)[C@@H]2C1)C(=O)C=1C=C(O)C=C(O)C=1)C)N1C=NC=N1 KSEANNCWEPGWEE-YAEZTRJGSA-N 0.000 claims 1
- SRBVKIRIZZAICT-ZFXXHYCBSA-N [(1s,2r,3s,4as,8as)-3-(imidazol-1-ylmethyl)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound C([C@@H]1[C@H]([C@@H]([C@@]2(C)CCCC(C)(C)[C@@H]2C1)C(=O)C=1C=C(O)C=C(O)C=1)C)N1C=CN=C1 SRBVKIRIZZAICT-ZFXXHYCBSA-N 0.000 claims 1
- XPKAYQJEGNSNHO-AVGXJXSMSA-N [(1s,2s,3r,4as,8as)-2,5,5,8a-tetramethyl-3-(1h-pyrrol-2-ylmethylamino)-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1NC=CC=1)C1=CC(O)=CC(O)=C1 XPKAYQJEGNSNHO-AVGXJXSMSA-N 0.000 claims 1
- JXJWSHHASMLBDV-LEYBTYMMSA-N [(1s,2s,3r,4as,8as)-2,5,5,8a-tetramethyl-3-(pyridin-2-ylmethylamino)-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1N=CC=CC=1)C1=CC(O)=CC(O)=C1 JXJWSHHASMLBDV-LEYBTYMMSA-N 0.000 claims 1
- XGOIENMCXVMVRH-LEYBTYMMSA-N [(1s,2s,3r,4as,8as)-2,5,5,8a-tetramethyl-3-(pyridin-4-ylmethylamino)-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1C=CN=CC=1)C1=CC(O)=CC(O)=C1 XGOIENMCXVMVRH-LEYBTYMMSA-N 0.000 claims 1
- OXKXKLBMTRIPRF-SKUJFBAQSA-N [(1s,2s,3r,4as,8as)-3-(1h-imidazol-2-ylmethylamino)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1NC=CN=1)C1=CC(O)=CC(O)=C1 OXKXKLBMTRIPRF-SKUJFBAQSA-N 0.000 claims 1
- WZOUNMHBDGGWAS-XLHZIAIKSA-N [(1s,2s,3r,4as,8as)-3-(1h-imidazol-5-ylmethylamino)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1NC=NC=1)C1=CC(O)=CC(O)=C1 WZOUNMHBDGGWAS-XLHZIAIKSA-N 0.000 claims 1
- ZWQFVZLPWRFTIH-QZWMETGYSA-N [(1s,2s,3r,4as,8as)-3-(1h-imidazol-5-ylmethylamino)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCC=1NC=NC=1)C1=CC(C)=CC(O)=C1 ZWQFVZLPWRFTIH-QZWMETGYSA-N 0.000 claims 1
- JQAIUZBSLRHLFB-XWXRQGFWSA-N [(1s,2s,3r,4as,8as)-3-(3-aminopropylamino)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NCCCN)C1=CC(O)=CC(O)=C1 JQAIUZBSLRHLFB-XWXRQGFWSA-N 0.000 claims 1
- NLVGYPKDZKLKRV-BYDXQTBQSA-N [(1s,2s,3r,4as,8as)-3-[(4-methoxyphenyl)methylamino]-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1CN[C@H]1[C@@H](C)[C@H](C(=O)C=2C=C(OC)C=C(OC)C=2)[C@@]2(C)CCCC(C)(C)[C@@H]2C1 NLVGYPKDZKLKRV-BYDXQTBQSA-N 0.000 claims 1
- IWKLYPPLZQAXNF-AVDSOWMKSA-N [(1s,2s,3r,4as,8as)-3-amino-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dihydroxyphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@@H](N)[C@H]1C)C1=CC(O)=CC(O)=C1 IWKLYPPLZQAXNF-AVDSOWMKSA-N 0.000 claims 1
- IFFGUYPIGOPPQS-XAWHHARUSA-N [(1s,2s,3r,4as,8as)-3-amino-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](N)[C@H]2C)C)=C1 IFFGUYPIGOPPQS-XAWHHARUSA-N 0.000 claims 1
- YRKKWFNFSFLNGQ-AUJACXKFSA-N [(1s,2s,3r,4as,8as)-3-amino-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](N)[C@H]2C)C)=C1 YRKKWFNFSFLNGQ-AUJACXKFSA-N 0.000 claims 1
- WSAKYOCXDGHENV-JWEPWGPDSA-N [(1s,2s,4as,8as)-3-(3-aminopropylamino)-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC([C@H]2C)NCCCN)C)=C1 WSAKYOCXDGHENV-JWEPWGPDSA-N 0.000 claims 1
- AHSZNASQNYUMNI-DJHDCLNUSA-N [(1s,2s,4as,8as)-3-hydroxy-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC(O)[C@H]1C)C1=CC(C)=CC(O)=C1 AHSZNASQNYUMNI-DJHDCLNUSA-N 0.000 claims 1
- GXSWCVIZHPJIDZ-MZKRTTBSSA-N [(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC=C2C)C)=C1 GXSWCVIZHPJIDZ-MZKRTTBSSA-N 0.000 claims 1
- RHLOMFHVMOYJBK-MZKRTTBSSA-N [(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanone Chemical compound COC1=CC(C)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC=C2C)C)=C1 RHLOMFHVMOYJBK-MZKRTTBSSA-N 0.000 claims 1
- ZLUBYVXMWQDIQY-MHONLFDUSA-N [(1s,4as,8as)-3-amino-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC(N)C1C)C1=CC(C)=CC(O)=C1 ZLUBYVXMWQDIQY-MHONLFDUSA-N 0.000 claims 1
- AHSZNASQNYUMNI-LMQSOCQSSA-N [(2r,3r,4as,8as)-3-hydroxy-2,5,5,8a-tetramethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound C1([C@@]2(C)CCCC(C)(C)[C@@H]2C[C@@H](O)[C@@H]1C)C(=O)C1=CC(C)=CC(O)=C1 AHSZNASQNYUMNI-LMQSOCQSSA-N 0.000 claims 1
- GWZUIDJUWIQYRF-NOAQKIQUSA-N [(4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound C1([C@@]2(C)CCCC(C)(C)[C@@H]2CC=C1C)C(=O)C1=CC(C)=CC(O)=C1 GWZUIDJUWIQYRF-NOAQKIQUSA-N 0.000 claims 1
- HIGMBDZBYNJULQ-AVRDEDQJSA-N [(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-(3-hydroxy-5-methylphenyl)methanone Chemical compound C([C@H]1C(C)(C)CCC[C@@]11C)CC(C)=C1C(=O)C1=CC(C)=CC(O)=C1 HIGMBDZBYNJULQ-AVRDEDQJSA-N 0.000 claims 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- FXKZQMYOBJXFRZ-COXDHOHBSA-N n-[(2r,3s,4s,4ar)-4-[2-(furan-2-carbonylamino)ethyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)CNC(=O)C1=CC=CO1 FXKZQMYOBJXFRZ-COXDHOHBSA-N 0.000 claims 1
- YBUYMYMIDLYYBG-DCKZOCFTSA-N n-[(2r,3s,4s,4as)-3,4a,8,8-tetramethyl-4-(1,2,4-triazol-1-ylmethyl)-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)N1C=NC=N1 YBUYMYMIDLYYBG-DCKZOCFTSA-N 0.000 claims 1
- XAHUFHFNLICIQC-UZXAYIJVSA-N n-[(2r,3s,4s,4as)-3,4a,8,8-tetramethyl-4-[(pyridine-4-carbonylamino)methyl]-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)NC(=O)C1=CC=NC=C1 XAHUFHFNLICIQC-UZXAYIJVSA-N 0.000 claims 1
- RHLXWQZEVKRDEO-RQJXJERJSA-N n-[(2r,3s,4s,4as)-3,4a,8,8-tetramethyl-4-[(pyridine-4-carbonylamino)methyl]-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)NC(=O)C1=CC=NC=C1 RHLXWQZEVKRDEO-RQJXJERJSA-N 0.000 claims 1
- GHYLFRPZLMKBHA-WQSZAJLVSA-N n-[(2r,3s,4s,4as)-3,4a,8,8-tetramethyl-4-[[[4-(trifluoromethyl)benzoyl]amino]methyl]-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)NC(=O)C1=CC=C(C(F)(F)F)C=C1 GHYLFRPZLMKBHA-WQSZAJLVSA-N 0.000 claims 1
- DBFREAQZRPQTRK-HBHCANOMSA-N n-[(2r,3s,4s,4as)-4-(imidazol-1-ylmethyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)N1C=CN=C1 DBFREAQZRPQTRK-HBHCANOMSA-N 0.000 claims 1
- VYYRCVDIRXFGAJ-FLDDEYDQSA-N n-[(2r,3s,4s,4as)-4-[(furan-2-carbonylamino)methyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)NC(=O)C1=CC=CO1 VYYRCVDIRXFGAJ-FLDDEYDQSA-N 0.000 claims 1
- QWTDZGGOZRPXJQ-WEYNBAESSA-N n-[(2r,3s,4s,4as)-4-[(furan-2-carbonylamino)methyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)NC(=O)C1=CC=CO1 QWTDZGGOZRPXJQ-WEYNBAESSA-N 0.000 claims 1
- JMZQHFLWMYOZOM-LREYWEAYSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-2-methylbenzamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C(=CC=CC=1)C)C1=CC(O)=CC(O)=C1 JMZQHFLWMYOZOM-LREYWEAYSA-N 0.000 claims 1
- LQYWOVFFLISPEM-URHPLWOHSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-aminopropanamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)CCN)C1=CC(O)=CC(O)=C1 LQYWOVFFLISPEM-URHPLWOHSA-N 0.000 claims 1
- OFEILIJEANQEGL-LREYWEAYSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-methylbenzamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=C(C)C=CC=1)C1=CC(O)=CC(O)=C1 OFEILIJEANQEGL-LREYWEAYSA-N 0.000 claims 1
- MTLHEMUWNFOZDW-LREYWEAYSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylbenzamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=CC(C)=CC=1)C1=CC(O)=CC(O)=C1 MTLHEMUWNFOZDW-LREYWEAYSA-N 0.000 claims 1
- RXROBVVLADCOLD-VFTFQOQOSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)C1=CC(O)=CC(O)=C1 RXROBVVLADCOLD-VFTFQOQOSA-N 0.000 claims 1
- YDJJYOPQUDBSGG-FRNKLHFDSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-6-aminopyridine-3-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=NC(N)=CC=1)C1=CC(O)=CC(O)=C1 YDJJYOPQUDBSGG-FRNKLHFDSA-N 0.000 claims 1
- PZFBRNMFPKTPFH-HEPYOUEBSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]acetamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(C)=O)C1=CC(O)=CC(O)=C1 PZFBRNMFPKTPFH-HEPYOUEBSA-N 0.000 claims 1
- LBRCLYOZQVUMSX-VROLEJAFSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]benzamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=CC=CC=1)C1=CC(O)=CC(O)=C1 LBRCLYOZQVUMSX-VROLEJAFSA-N 0.000 claims 1
- ANVYWEDOADJWKL-MTLWAPPXSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]naphthalene-2-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=C2C=CC=CC2=CC=1)C1=CC(O)=CC(O)=C1 ANVYWEDOADJWKL-MTLWAPPXSA-N 0.000 claims 1
- CWSQMOMLBCEAHK-LZITZJIASA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]piperidine-4-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C1CCNCC1)C1=CC(O)=CC(O)=C1 CWSQMOMLBCEAHK-LZITZJIASA-N 0.000 claims 1
- YSNUXJCXNYXJSZ-LZITZJIASA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-2-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1N=CC=CC=1)C1=CC(O)=CC(O)=C1 YSNUXJCXNYXJSZ-LZITZJIASA-N 0.000 claims 1
- JBBCDNNDYGLMOE-LZITZJIASA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)C1=CC(O)=CC(O)=C1 JBBCDNNDYGLMOE-LZITZJIASA-N 0.000 claims 1
- AULHQHGCDZKQCZ-HXEJGHFOSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-2-methylbenzamide Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@H]([C@H]2C)NC(=O)C=2C(=CC=CC=2)C)C)=C1 AULHQHGCDZKQCZ-HXEJGHFOSA-N 0.000 claims 1
- HNSXTGZXVKMRIC-HXEJGHFOSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-3-methylbenzamide Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@H]([C@H]2C)NC(=O)C=2C=C(C)C=CC=2)C)=C1 HNSXTGZXVKMRIC-HXEJGHFOSA-N 0.000 claims 1
- XBCJIYSDCMGIGA-HXEJGHFOSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylbenzamide Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@H]([C@H]2C)NC(=O)C=2C=CC(C)=CC=2)C)=C1 XBCJIYSDCMGIGA-HXEJGHFOSA-N 0.000 claims 1
- ZCZGBOSROJUYNW-MXFFVKIZSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]naphthalene-2-carboxamide Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@H]([C@H]2C)NC(=O)C=2C=C3C=CC=CC3=CC=2)C)=C1 ZCZGBOSROJUYNW-MXFFVKIZSA-N 0.000 claims 1
- WJCIWWZEIDKZEP-LREYWEAYSA-N n-[(2r,3s,4s,4as,8as)-4-(3,5-dimethoxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@H]([C@H]2C)NC(=O)C=2C=NC=CC=2)C)=C1 WJCIWWZEIDKZEP-LREYWEAYSA-N 0.000 claims 1
- VFLWFQPOZSXAFG-XWXRQGFWSA-N n-[(2r,3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]acetamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NC(C)=O)C1=CC(C)=CC(O)=C1 VFLWFQPOZSXAFG-XWXRQGFWSA-N 0.000 claims 1
- AMAPWBAMJLDBKN-AUJACXKFSA-N n-[(2r,3s,4s,4as,8as)-4-(3-hydroxy-5-methylbenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]methanesulfonamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H]([C@H]1C)NS(C)(=O)=O)C1=CC(C)=CC(O)=C1 AMAPWBAMJLDBKN-AUJACXKFSA-N 0.000 claims 1
- UZMMSTZCXAAGED-BSUMQHDTSA-N n-[(3s,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyrazine-2-carboxamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC([C@H]1C)NC(=O)C=1N=CC=NC=1)C1=CC(O)=CC(O)=C1 UZMMSTZCXAAGED-BSUMQHDTSA-N 0.000 claims 1
- XAAZYOMOZNNDNI-FSNUSLJUSA-N n-[[(2r,3r,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]methyl]acetamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@@H](CNC(C)=O)[C@H]1C)C1=CC(O)=CC(O)=C1 XAAZYOMOZNNDNI-FSNUSLJUSA-N 0.000 claims 1
- XAAZYOMOZNNDNI-KVTDIYAISA-N n-[[(2s,3r,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]methyl]acetamide Chemical compound O=C([C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2C[C@H](CNC(C)=O)[C@H]1C)C1=CC(O)=CC(O)=C1 XAAZYOMOZNNDNI-KVTDIYAISA-N 0.000 claims 1
- MTJDADMLOILVNS-UNLYMHQNSA-N n-[[(2s,3r,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]methyl]benzamide Chemical compound C([C@@H]1[C@H]([C@@H]([C@@]2(C)CCCC(C)(C)[C@@H]2C1)C(=O)C=1C=C(O)C=C(O)C=1)C)NC(=O)C1=CC=CC=C1 MTJDADMLOILVNS-UNLYMHQNSA-N 0.000 claims 1
- LAFPIJSDFMBDCO-HOCISNMZSA-N n-[[(2s,3r,4s,4as,8as)-4-(3,5-dihydroxybenzoyl)-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]methyl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@H]([C@@H]([C@@]2(C)CCCC(C)(C)[C@@H]2C1)C(=O)C=1C=C(O)C=C(O)C=1)C)NC(=O)C1=CC=CN=C1 LAFPIJSDFMBDCO-HOCISNMZSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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| US201361750695P | 2013-01-09 | 2013-01-09 | |
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| JP2015551836A Division JP2016510320A (ja) | 2013-01-09 | 2014-01-07 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
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| JP2018135335A JP2018135335A (ja) | 2018-08-30 |
| JP2018135335A5 true JP2018135335A5 (https=) | 2018-11-08 |
| JP6526275B2 JP6526275B2 (ja) | 2019-06-05 |
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| JP2015551836A Ceased JP2016510320A (ja) | 2013-01-09 | 2014-01-07 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
| JP2018042934A Expired - Fee Related JP6526275B2 (ja) | 2013-01-09 | 2018-03-09 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
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| US (3) | US9540353B2 (https=) |
| EP (1) | EP2943470A1 (https=) |
| JP (2) | JP2016510320A (https=) |
| KR (1) | KR20150106895A (https=) |
| CN (2) | CN108752236A (https=) |
| AU (2) | AU2014205587B2 (https=) |
| BR (1) | BR112015016206A2 (https=) |
| CA (1) | CA2896559A1 (https=) |
| HK (1) | HK1216886A1 (https=) |
| IL (1) | IL239659A0 (https=) |
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| RU (1) | RU2015133177A (https=) |
| WO (1) | WO2014110036A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014110036A1 (en) | 2013-01-09 | 2014-07-17 | Aquinox Pharmaceuticals Inc. | Ship1 modulators and methods related thereto |
| WO2018126040A1 (en) | 2016-12-28 | 2018-07-05 | Aquinox Pharmaceuticals (Canada) Inc. | Crystalline solid forms of (1s,3s,4r)-4-((3as,4r,5s,7as)-4- (aminomethyl)-7a-methyl-1-methyleneoctahydro-1h-inden-5-yl)-3- (hydroxymethyl)-4-methylcyclohexanol |
| CN107602496B (zh) * | 2017-09-08 | 2020-10-13 | 南京农业大学 | 手性补身烷基杂环类化合物及其作为杀菌剂的用途 |
| WO2019195777A1 (en) | 2018-04-06 | 2019-10-10 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
| WO2019195692A1 (en) | 2018-04-06 | 2019-10-10 | Aquinox Pharmaceuticals (Canada) Inc. | Hexadecahydro-1h-cyclopenta[a]phenanthrene derivatives useful in treating pain and inflammation |
| EP3774746A1 (en) | 2018-04-06 | 2021-02-17 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
| WO2024220556A2 (en) * | 2023-04-20 | 2024-10-24 | Hb Therapeutics, Inc. | Heterocyclic sumo1 small molecule degraders and use thereof |
| CN116554063B (zh) * | 2023-05-23 | 2025-03-07 | 江苏省农用激素工程技术研究中心有限公司 | 氟胺磺隆中间体的制备方法 |
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| JP2002179564A (ja) | 1998-04-14 | 2002-06-26 | Toagosei Co Ltd | 抗真菌剤 |
| JPH11349478A (ja) * | 1998-06-03 | 1999-12-21 | Toagosei Co Ltd | 抗癌剤 |
| JP2001031663A (ja) * | 1999-07-14 | 2001-02-06 | Toagosei Co Ltd | エポキシ化合物およびその誘導体 |
| JP2001048873A (ja) * | 1999-08-10 | 2001-02-20 | Toagosei Co Ltd | エポキシ化合物およびその誘導体 |
| WO2003033517A1 (en) | 2001-10-17 | 2003-04-24 | The University Of British Columbia | Ship 1 modulators |
| WO2004035601A1 (en) | 2002-10-17 | 2004-04-29 | The University Of British Columbia | Ship 1 modulators |
| CA2521883C (en) | 2003-04-15 | 2013-09-17 | Inflazyme Pharmaceuticals Ltd. | Indene derivatives as pharmaceutical agents |
| JP2009541224A (ja) * | 2006-06-21 | 2009-11-26 | ザ・ユニバーシティ・オブ・ブリティッシュ・コロンビア | Ｓｈｉｐ１モジュレーター化合物 |
| RU2385863C2 (ru) | 2008-04-21 | 2010-04-10 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) (статус государственного учреждения) | N-ЗАМЕЩЕННЫЕ (1S,4aR,5S)-МЕТИЛ-5-[2-(2'-ОКСО-2',5'-ДИГИДРО-1Н-ПИРРОЛ-3'-ИЛ)ЭТИЛ]-1,4a-ДИМЕТИЛ-6-МЕТИЛЕНДЕКАГИДРОНАФТАЛИН-1-КАРБОКСИЛАТЫ, ОБЛАДАЮЩИЕ ПРОТИВОСУДОРОЖНОЙ АКТИВНОСТЬЮ |
| US8101605B2 (en) * | 2009-12-04 | 2012-01-24 | Aquinox Pharmaceuticals Inc. | SHIP1 modulators and methods related thereto |
| US9000050B2 (en) | 2010-08-20 | 2015-04-07 | The University Of British Columbia | SHIP1 modulators and related methods |
| WO2014110036A1 (en) | 2013-01-09 | 2014-07-17 | Aquinox Pharmaceuticals Inc. | Ship1 modulators and methods related thereto |
| MX2015012111A (es) | 2013-03-14 | 2016-05-05 | Aquinox Pharmaceuticals Canada Inc | Moduladores de ship1 y métodos relacionados con éstos. |
| US10100056B2 (en) | 2013-03-14 | 2018-10-16 | Aquinox Pharmaceuticals (Canada) Inc. | SHIP1 modulators and methods related thereto |
| US9944590B2 (en) | 2015-06-26 | 2018-04-17 | Aquinox Pharmaceuticals (Canada) Inc. | Crystalline solid forms of the acetate salt of (1S,3S,4R)-4-((3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol |
| US10053415B2 (en) | 2016-01-20 | 2018-08-21 | Aquinox Pharmaceuticals (Canada) Inc. | Synthesis of a substituted indene derivative |
-
2014
- 2014-01-07 WO PCT/US2014/010501 patent/WO2014110036A1/en not_active Ceased
- 2014-01-07 BR BR112015016206A patent/BR112015016206A2/pt not_active Application Discontinuation
- 2014-01-07 HK HK16104760.2A patent/HK1216886A1/zh unknown
- 2014-01-07 US US14/759,622 patent/US9540353B2/en not_active Expired - Fee Related
- 2014-01-07 AU AU2014205587A patent/AU2014205587B2/en not_active Ceased
- 2014-01-07 CN CN201810436062.5A patent/CN108752236A/zh active Pending
- 2014-01-07 CN CN201480013140.0A patent/CN105026375B/zh not_active Expired - Fee Related
- 2014-01-07 EP EP14702673.6A patent/EP2943470A1/en not_active Withdrawn
- 2014-01-07 JP JP2015551836A patent/JP2016510320A/ja not_active Ceased
- 2014-01-07 KR KR1020157021150A patent/KR20150106895A/ko not_active Ceased
- 2014-01-07 RU RU2015133177A patent/RU2015133177A/ru not_active Application Discontinuation
- 2014-01-07 MX MX2015008873A patent/MX2015008873A/es unknown
- 2014-01-07 CA CA2896559A patent/CA2896559A1/en not_active Abandoned
-
2015
- 2015-06-22 ZA ZA2015/04477A patent/ZA201504477B/en unknown
- 2015-06-25 IL IL239659A patent/IL239659A0/en unknown
-
2016
- 2016-12-06 US US15/370,973 patent/US9937167B2/en not_active Expired - Fee Related
-
2018
- 2018-01-30 US US15/884,044 patent/US10272081B2/en not_active Expired - Fee Related
- 2018-03-09 JP JP2018042934A patent/JP6526275B2/ja not_active Expired - Fee Related
- 2018-08-23 AU AU2018220093A patent/AU2018220093A1/en not_active Abandoned
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