JP2017513932A5 - - Google Patents
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- JP2017513932A5 JP2017513932A5 JP2017503794A JP2017503794A JP2017513932A5 JP 2017513932 A5 JP2017513932 A5 JP 2017513932A5 JP 2017503794 A JP2017503794 A JP 2017503794A JP 2017503794 A JP2017503794 A JP 2017503794A JP 2017513932 A5 JP2017513932 A5 JP 2017513932A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triazaspiro
- decan
- fluoro
- oxobutan
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 268
- -1 1- (1- (3-fluoro-4-methoxyphenyl) -3-methyl-2,4-dioxo-1,3,8-triazaspiro [4.5] decane -8-yl) -3-methyl-1-oxobutan-2-yl Chemical group 0.000 claims description 188
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 102100021977 Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Human genes 0.000 claims description 6
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 230000004761 fibrosis Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 208000004296 neuralgia Diseases 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 5
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 4
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 206010064190 Cholestatic pruritus Diseases 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- 108010022198 alkylglycerophosphoethanolamine phosphodiesterase Proteins 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 230000006020 chronic inflammation Effects 0.000 claims description 3
- 230000003176 fibrotic effect Effects 0.000 claims description 3
- 210000004698 lymphocyte Anatomy 0.000 claims description 3
- DDLPGTOHZZKQLP-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC(C(F)(F)F)=CC=C1F DDLPGTOHZZKQLP-UHFFFAOYSA-N 0.000 claims description 2
- KFTMKTOJVHOBGJ-HSZRJFAPSA-N 2-fluoro-N-[(2R)-3-methyl-1-[3-methyl-1-(2-methylindazol-5-yl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]-5-(trifluoromethyl)benzamide Chemical compound FC1=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3C3=CC4=CN(N=C4C=C3)C)=O)C)=O)CC2)C(C)C)C=C(C=C1)C(F)(F)F KFTMKTOJVHOBGJ-HSZRJFAPSA-N 0.000 claims description 2
- YGDNQVHIOIWKCP-JOCHJYFZSA-N 2-fluoro-N-[(2R)-3-methyl-1-[3-methyl-1-(3-methyl-2-oxo-1,3-benzoxazol-5-yl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]-5-(trifluoromethyl)benzamide Chemical compound FC1=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3C=3C=CC4=C(N(C(O4)=O)C)C=3)=O)C)=O)CC2)C(C)C)C=C(C=C1)C(F)(F)F YGDNQVHIOIWKCP-JOCHJYFZSA-N 0.000 claims description 2
- CALWUCIHXRLQQU-HSZRJFAPSA-N 2-fluoro-N-[(2R)-3-methyl-1-[3-methyl-1-[(2-methyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)methyl]-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]-5-(trifluoromethyl)benzamide Chemical compound FC1=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3CC3=CC=4N(C=C3)N=C(N=4)C)=O)C)=O)CC2)C(C)C)C=C(C=C1)C(F)(F)F CALWUCIHXRLQQU-HSZRJFAPSA-N 0.000 claims description 2
- ZGWXCVZYJDJXBF-OAQYLSRUSA-N 2-fluoro-N-[(2R)-3-methyl-1-[3-methyl-2,4-dioxo-1-(2-oxo-3H-1,3-benzoxazol-5-yl)-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]-5-(trifluoromethyl)benzamide Chemical compound FC1=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3C=3C=CC4=C(NC(O4)=O)C=3)=O)C)=O)CC2)C(C)C)C=C(C=C1)C(F)(F)F ZGWXCVZYJDJXBF-OAQYLSRUSA-N 0.000 claims description 2
- OJQHZZIHMKRVBA-UHFFFAOYSA-N 2-fluoro-N-[1-[1-(1H-indazol-5-yl)-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]-2-methyl-1-oxopropan-2-yl]-5-(trifluoromethyl)benzamide Chemical compound N1N=CC2=CC(=CC=C12)N1C(N(C(C11CCN(CC1)C(C(C)(C)NC(C1=C(C=CC(=C1)C(F)(F)F)F)=O)=O)=O)C)=O OJQHZZIHMKRVBA-UHFFFAOYSA-N 0.000 claims description 2
- POTURENPSFEWGN-HSZRJFAPSA-N 3-ethyl-N-[(2R)-3-methyl-1-(3-methyl-2,4-dioxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)-1-oxobutan-2-yl]benzamide Chemical compound C(C)C=1C=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3C3=CC=CC=C3)=O)C)=O)CC2)C(C)C)C=CC=1 POTURENPSFEWGN-HSZRJFAPSA-N 0.000 claims description 2
- VJJKTFFNAHQWJT-OAQYLSRUSA-N 4-[8-[(2R)-2-[[2-fluoro-5-(trifluoromethoxy)benzoyl]amino]-3-methylbutanoyl]-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-1-yl]benzoic acid Chemical compound FC1=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(C(N3C3=CC=C(C(=O)O)C=C3)=O)C)=O)CC2)C(C)C)C=C(C=C1)OC(F)(F)F VJJKTFFNAHQWJT-OAQYLSRUSA-N 0.000 claims description 2
- FUGRDPNAIONVQE-JOCHJYFZSA-N 4-[8-[(2R)-2-[[2-fluoro-5-(trifluoromethoxy)benzoyl]amino]-3-methylbutanoyl]-3-methyl-4-oxo-1,3,8-triazaspiro[4.5]decan-1-yl]benzoic acid Chemical compound CC(C)[C@@H](NC(=O)C1=C(F)C=CC(OC(F)(F)F)=C1)C(=O)N1CCC2(CC1)N(CN(C)C2=O)C1=CC=C(C=C1)C(O)=O FUGRDPNAIONVQE-JOCHJYFZSA-N 0.000 claims description 2
- XTHYGPKTTMYUHE-JOCHJYFZSA-N 4-[8-[(2R)-2-[[3-chloro-5-(trifluoromethyl)benzoyl]amino]-3-methylbutanoyl]-3-methyl-4-oxo-1,3,8-triazaspiro[4.5]decan-1-yl]benzoic acid Chemical compound ClC=1C=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(CN3C3=CC=C(C(=O)O)C=C3)C)=O)CC2)C(C)C)C=C(C=1)C(F)(F)F XTHYGPKTTMYUHE-JOCHJYFZSA-N 0.000 claims description 2
- LAAYUKAQBBWYLR-RUZDIDTESA-N 5-ethyl-2-fluoro-N-[(2R)-1-[1-[4-(methanesulfonamido)phenyl]-3-methyl-4-oxo-1,3,8-triazaspiro[4.5]decan-8-yl]-3-methyl-1-oxobutan-2-yl]benzamide Chemical compound C(C)C=1C=CC(=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(CN3C3=CC=C(C=C3)NS(=O)(=O)C)C)=O)CC2)C(C)C)C=1)F LAAYUKAQBBWYLR-RUZDIDTESA-N 0.000 claims description 2
- OGGLMNLWYAICPS-VCUSLETLSA-N 5-ethyl-2-fluoro-N-[(2R)-3-methoxy-1-[1-(4-methoxyphenyl)-3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]benzamide Chemical compound CCC1=CC=C(F)C(=C1)C(=O)N[C@H](C(C)OC)C(=O)N1CCC2(CC1)N(C(=O)N(C)C2=O)C1=CC=C(OC)C=C1 OGGLMNLWYAICPS-VCUSLETLSA-N 0.000 claims description 2
- AISJEVBDBCFJKD-RUZDIDTESA-N 5-ethyl-2-fluoro-N-[(2R)-3-methyl-1-[3-methyl-1-(4-methylsulfonylphenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-8-yl]-1-oxobutan-2-yl]benzamide Chemical compound C(C)C=1C=CC(=C(C(=O)N[C@@H](C(=O)N2CCC3(C(N(CN3C3=CC=C(C=C3)S(=O)(=O)C)C)=O)CC2)C(C)C)C=1)F AISJEVBDBCFJKD-RUZDIDTESA-N 0.000 claims description 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 2
- 206010005949 Bone cancer Diseases 0.000 claims description 2
- 208000018084 Bone neoplasm Diseases 0.000 claims description 2
- GIBOXIQBZGLXHE-HSZRJFAPSA-N BrC1=CC=C(C=C1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=CC(=CC=C2)C)=O)=O)=O)C Chemical compound BrC1=CC=C(C=C1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=CC(=CC=C2)C)=O)=O)=O)C GIBOXIQBZGLXHE-HSZRJFAPSA-N 0.000 claims description 2
- XQWCVMSRUVGIQX-HSZRJFAPSA-N BrC=1C=C(C=CC1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=CC(=CC=C2)C)=O)=O)=O)C Chemical compound BrC=1C=C(C=CC1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=CC(=CC=C2)C)=O)=O)=O)C XQWCVMSRUVGIQX-HSZRJFAPSA-N 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- BVYYDEKYMCUJBZ-XMMPIXPASA-N C(#N)C1=CC=C(C=C1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=C(C(=CC=C2)C)F)=O)=O)=O)C Chemical compound C(#N)C1=CC=C(C=C1)N1CN(C(C12CCN(CC2)C([C@@H](C(C)C)NC(C2=C(C(=CC=C2)C)F)=O)=O)=O)C BVYYDEKYMCUJBZ-XMMPIXPASA-N 0.000 claims description 2
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2015
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- 2015-04-03 JP JP2017503794A patent/JP6616821B2/ja not_active Expired - Fee Related
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- 2015-04-03 EP EP15773254.6A patent/EP3125895A4/en not_active Withdrawn
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- 2015-04-03 KR KR1020167030589A patent/KR20160133004A/ko not_active Withdrawn
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2016
- 2016-09-26 IL IL248050A patent/IL248050A0/en unknown
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- 2016-10-04 CL CL2016002516A patent/CL2016002516A1/es unknown
- 2016-10-26 EC ECIEPI201684293A patent/ECSP16084293A/es unknown
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2018
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2019
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- 2019-11-08 JP JP2019203023A patent/JP2020040960A/ja active Pending
- 2019-11-15 AU AU2019264641A patent/AU2019264641A1/en not_active Abandoned