RU2007119427A - Соединения, являющиеся ингибиторами гликогенфосфорилазы, и фармацевтические композиции на их основе - Google Patents
Соединения, являющиеся ингибиторами гликогенфосфорилазы, и фармацевтические композиции на их основе Download PDFInfo
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- RU2007119427A RU2007119427A RU2007119427/04A RU2007119427A RU2007119427A RU 2007119427 A RU2007119427 A RU 2007119427A RU 2007119427/04 A RU2007119427/04 A RU 2007119427/04A RU 2007119427 A RU2007119427 A RU 2007119427A RU 2007119427 A RU2007119427 A RU 2007119427A
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- RU
- Russia
- Prior art keywords
- amino
- carbonyl
- trimethylphenyl
- cyclohexyl
- naphthalenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 239000003112 inhibitor Substances 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 12
- 239000001301 oxygen Chemical group 0.000 claims abstract 12
- 229910052717 sulfur Chemical group 0.000 claims abstract 12
- 239000011593 sulfur Chemical group 0.000 claims abstract 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 239000012453 solvate Substances 0.000 claims abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- 239000001257 hydrogen Substances 0.000 claims abstract 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 188
- -1 {[(2,6-dimethylphenyl) amino] carbonyl} amino Chemical group 0.000 claims 109
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 94
- 229960000583 acetic acid Drugs 0.000 claims 34
- 235000011054 acetic acid Nutrition 0.000 claims 34
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 15
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 10
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 8
- 206010012601 diabetes mellitus Diseases 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 239000004473 Threonine Substances 0.000 claims 4
- 229960005261 aspartic acid Drugs 0.000 claims 4
- URAXDCBRCGSGAT-UHFFFAOYSA-N cyclooctanecarboxylic acid Chemical compound OC(=O)C1CCCCCCC1 URAXDCBRCGSGAT-UHFFFAOYSA-N 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 208000031225 myocardial ischemia Diseases 0.000 claims 4
- 229960002898 threonine Drugs 0.000 claims 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 239000007791 liquid phase Substances 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims 2
- YBGWAVYJXCJCBQ-HXUWFJFHSA-N (2r)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanedioic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](CC(O)=O)C(O)=O YBGWAVYJXCJCBQ-HXUWFJFHSA-N 0.000 claims 1
- PNZJUXCYWXNOJS-MUUNZHRXSA-N (2r)-2-cyclohexyl-2-[[2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]propanoic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@@](C)(C(O)=O)C1CCCCC1 PNZJUXCYWXNOJS-MUUNZHRXSA-N 0.000 claims 1
- KMJGFTATOAQJQV-VWLOTQADSA-N (2s)-2-(4,4-difluorocyclohexyl)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCC(F)(F)CC1 KMJGFTATOAQJQV-VWLOTQADSA-N 0.000 claims 1
- VMRQQMMYBLNPPN-ZWNWOPDOSA-N (2s)-2-(4-hydroxycyclohexyl)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCC(O)CC1 VMRQQMMYBLNPPN-ZWNWOPDOSA-N 0.000 claims 1
- PGXXUARYUOJTPS-ITWBZBEWSA-N (2s)-2-(4-methylcyclohexyl)-2-[[3-[(2,4,6-trichlorophenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound C1CC(C)CCC1[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl PGXXUARYUOJTPS-ITWBZBEWSA-N 0.000 claims 1
- DSHWUCACJTVPNS-DCFJUCRTSA-N (2s)-2-[(1s)-3-hydroxycyclohexyl]-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)[C@@H]1CC(O)CCC1 DSHWUCACJTVPNS-DCFJUCRTSA-N 0.000 claims 1
- MOUYIWPAGWNTNV-LVXARBLLSA-N (2s)-2-[(1s)-3-oxocyclohexyl]-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)[C@@H]1CC(=O)CCC1 MOUYIWPAGWNTNV-LVXARBLLSA-N 0.000 claims 1
- XNPFMIJBGWLWLO-MHZLTWQESA-N (2s)-2-[[2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]-4-(4-methoxyphenyl)benzoyl]amino]-4-ethoxy-4-oxobutanoic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(OC)=CC=2)=CC=C1C(=O)N[C@@H](CC(=O)OCC)C(O)=O XNPFMIJBGWLWLO-MHZLTWQESA-N 0.000 claims 1
- RQXYHVJAIRBCJV-VWLOTQADSA-N (2s)-2-[[2-[(4-butyl-2,6-dimethylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]-2-cyclohexylacetic acid Chemical compound CC1=CC(CCCC)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 RQXYHVJAIRBCJV-VWLOTQADSA-N 0.000 claims 1
- YBGWAVYJXCJCBQ-FQEVSTJZSA-N (2s)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanedioic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@@H](CC(O)=O)C(O)=O YBGWAVYJXCJCBQ-FQEVSTJZSA-N 0.000 claims 1
- FZTWCIHSJDWTMS-NRFANRHFSA-N (2s)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]pentanoic acid Chemical compound CCC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C FZTWCIHSJDWTMS-NRFANRHFSA-N 0.000 claims 1
- OAPUWSORURBZQJ-KRWDZBQOSA-N (2s)-2-[[3-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]naphthalene-2-carbonyl]amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl OAPUWSORURBZQJ-KRWDZBQOSA-N 0.000 claims 1
- JGTFEPCCEWXOGA-QFIPXVFZSA-N (2s)-2-[[3-[[2-chloro-6-(trifluoromethyl)phenyl]carbamoylamino]naphthalene-2-carbonyl]amino]-2-cyclohexylacetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=CC=C1C(F)(F)F JGTFEPCCEWXOGA-QFIPXVFZSA-N 0.000 claims 1
- DPAGGBMMEPPLEA-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethyl-4-pentylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]acetic acid Chemical compound CC1=CC(CCCCC)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DPAGGBMMEPPLEA-SANMLTNESA-N 0.000 claims 1
- CRLOMSZZRCXMCE-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethyl-4-prop-2-enylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]acetic acid Chemical compound CC1=CC(CC=C)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 CRLOMSZZRCXMCE-DEOSSOPVSA-N 0.000 claims 1
- DVLYGIYYRPEEQN-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]acetic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DVLYGIYYRPEEQN-DEOSSOPVSA-N 0.000 claims 1
- WHMNOQMNAGTIDC-QHCPKHFHSA-N (2s)-2-cyclohexyl-2-[[2-[(4-ethyl-2,6-dimethylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]acetic acid Chemical compound CC1=CC(CC)=CC(C)=C1NC(=O)NC1=CC(F)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 WHMNOQMNAGTIDC-QHCPKHFHSA-N 0.000 claims 1
- OWSCCUAACVREGG-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[2-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-4-(3,4-difluorophenyl)benzoyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC=C(C=2C=C(F)C(F)=CC=2)C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl OWSCCUAACVREGG-DEOSSOPVSA-N 0.000 claims 1
- XIFDZADJAILVIQ-VWLOTQADSA-N (2s)-2-cyclohexyl-2-[[2-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-4-(4-methoxyphenyl)benzoyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(OC(F)(F)F)=CC=2Cl)Cl)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 XIFDZADJAILVIQ-VWLOTQADSA-N 0.000 claims 1
- BHPFSCAPXQVGGX-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[2-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-4-phenylbenzoyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl BHPFSCAPXQVGGX-DEOSSOPVSA-N 0.000 claims 1
- HGHDQMKDKKPUMU-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[2-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-5-(4-methoxyphenyl)thiophene-3-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(S1)=CC(C(=O)N[C@@H](C2CCCCC2)C(O)=O)=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl HGHDQMKDKKPUMU-QFIPXVFZSA-N 0.000 claims 1
- JFLOUFQZSGVQOB-NRFANRHFSA-N (2s)-2-cyclohexyl-2-[[2-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-5-[4-(trifluoromethoxy)phenyl]thiophene-3-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C=1C=C(C=2C=CC(OC(F)(F)F)=CC=2)SC=1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl JFLOUFQZSGVQOB-NRFANRHFSA-N 0.000 claims 1
- XUJLFPBPUYFSHU-VWLOTQADSA-N (2s)-2-cyclohexyl-2-[[2-[[4-(cyclopropylmethyl)-2,6-dimethylphenyl]carbamoylamino]-4-fluorobenzoyl]amino]acetic acid Chemical compound C=1C(C)=C(NC(=O)NC=2C(=CC=C(F)C=2)C(=O)N[C@@H](C2CCCCC2)C(O)=O)C(C)=CC=1CC1CC1 XUJLFPBPUYFSHU-VWLOTQADSA-N 0.000 claims 1
- CTDGLQDIWIHFIA-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[(2,4,6-trichlorophenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl CTDGLQDIWIHFIA-QFIPXVFZSA-N 0.000 claims 1
- LZSPMCXLIBZRHM-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 LZSPMCXLIBZRHM-SANMLTNESA-N 0.000 claims 1
- MBOPBZURDPABRJ-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]quinoline-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2N=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 MBOPBZURDPABRJ-DEOSSOPVSA-N 0.000 claims 1
- OQKRNCQAWNRSFF-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dichloro-4-fluorophenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(F)C=C1Cl OQKRNCQAWNRSFF-QFIPXVFZSA-N 0.000 claims 1
- MGXCJXJUUJQRHZ-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dichlorophenyl)carbamoylamino]-5-(4-methoxyphenyl)thiophene-2-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)NC=2C(=CC=CC=2Cl)Cl)=C(C(=O)N[C@@H](C2CCCCC2)C(O)=O)S1 MGXCJXJUUJQRHZ-QFIPXVFZSA-N 0.000 claims 1
- LVUXSMQZOPUYNC-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dimethyl-4-propoxyphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(OCCC)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 LVUXSMQZOPUYNC-NDEPHWFRSA-N 0.000 claims 1
- ODYYARSQQUMXPX-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 ODYYARSQQUMXPX-NDEPHWFRSA-N 0.000 claims 1
- SKFIKECGWBTQKZ-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[3-[(4-cyclopropylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC(C=C1)=CC=C1C1CC1 SKFIKECGWBTQKZ-SANMLTNESA-N 0.000 claims 1
- PTEMBXDMBFKQOP-MHZLTWQESA-N (2s)-2-cyclohexyl-2-[[3-[(4-ethyl-2,6-dimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(CC)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 PTEMBXDMBFKQOP-MHZLTWQESA-N 0.000 claims 1
- XSZWFPQMSJZOSA-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]-5-(4-methoxyphenyl)thiophene-2-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)NC=2C(=CC(OC(F)(F)F)=CC=2Cl)Cl)=C(C(=O)N[C@@H](C2CCCCC2)C(O)=O)S1 XSZWFPQMSJZOSA-QFIPXVFZSA-N 0.000 claims 1
- VELSBWPCKDKOGF-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl VELSBWPCKDKOGF-QFIPXVFZSA-N 0.000 claims 1
- OZAQAMQVCWOOLF-VWLOTQADSA-N (2s)-2-cyclohexyl-2-[[3-[[2-(2,4,6-trichlorophenyl)acetyl]amino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)CC1=C(Cl)C=C(Cl)C=C1Cl OZAQAMQVCWOOLF-VWLOTQADSA-N 0.000 claims 1
- TVZUJCFOEBDZNF-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[3-[[2-(2,4,6-trimethylphenyl)acetyl]amino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1CC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 TVZUJCFOEBDZNF-NDEPHWFRSA-N 0.000 claims 1
- BOYKKVWANATAGN-SFHVURJKSA-N (2s)-2-cyclohexyl-2-[[4,5-dichloro-2-[(2,6-dichlorophenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC(Cl)=C(Cl)C=C1NC(=O)NC1=C(Cl)C=CC=C1Cl BOYKKVWANATAGN-SFHVURJKSA-N 0.000 claims 1
- DTIYMAKLXWWZPR-NRFANRHFSA-N (2s)-2-cyclohexyl-2-[[4,5-dichloro-2-[(2,6-dimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(Cl)=C(Cl)C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DTIYMAKLXWWZPR-NRFANRHFSA-N 0.000 claims 1
- WRPMIMJTJQWMER-MHZLTWQESA-N (2s)-2-cyclohexyl-2-[[4-(3,4-difluorophenyl)-2-[(2,6-dimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C(F)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 WRPMIMJTJQWMER-MHZLTWQESA-N 0.000 claims 1
- PTLMRHVAGWFRJQ-VWLOTQADSA-N (2s)-2-cyclopentyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCC1 PTLMRHVAGWFRJQ-VWLOTQADSA-N 0.000 claims 1
- JQJBEMLZNXOIQY-SANMLTNESA-N (2s)-3-phenyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]propanoic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 JQJBEMLZNXOIQY-SANMLTNESA-N 0.000 claims 1
- XGDKLKWSGQTMTH-QHCPKHFHSA-N (2s)-4-methyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]pentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C XGDKLKWSGQTMTH-QHCPKHFHSA-N 0.000 claims 1
- YCAVDJDBHPHXEP-QHCPKHFHSA-N (2s)-5-methyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]hexanoic acid Chemical compound CC(C)CC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C YCAVDJDBHPHXEP-QHCPKHFHSA-N 0.000 claims 1
- BJQXMDVHQGMWFX-DFXYEROKSA-N (2s,3r)-2-[[2-[[4-(cyclopropylmethyl)-2,6-dimethylphenyl]carbamoylamino]-4-(3-fluorophenyl)benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound CC(C)(C)O[C@H](C)[C@@H](C(O)=O)NC(=O)C1=CC=C(C=2C=C(F)C=CC=2)C=C1NC(=O)NC(C(=C1)C)=C(C)C=C1CC1CC1 BJQXMDVHQGMWFX-DFXYEROKSA-N 0.000 claims 1
- QVYCWEMVWQKRJH-OLILMLBXSA-N (2s,3r)-2-[[4-(3,4-difluorophenyl)-2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C(F)=CC=2)=CC=C1C(=O)N[C@@H]([C@@H](C)OC(C)(C)C)C(O)=O QVYCWEMVWQKRJH-OLILMLBXSA-N 0.000 claims 1
- XGTWUMJDHFUSBH-HRFSGMKKSA-N (2s,3r)-2-[[4-(4-fluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound CC(C)(C)O[C@H](C)[C@@H](C(O)=O)NC(=O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1NC(=O)NC1=C(C)C=C(C)C=C1C XGTWUMJDHFUSBH-HRFSGMKKSA-N 0.000 claims 1
- NFEHTHYGFWCOJE-HRFSGMKKSA-N (2s,3r)-3-[(2-methylpropan-2-yl)oxy]-2-[[3-[[2-(2,4,6-trimethylphenyl)acetyl]amino]naphthalene-2-carbonyl]amino]butanoic acid Chemical compound CC(C)(C)O[C@H](C)[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)CC1=C(C)C=C(C)C=C1C NFEHTHYGFWCOJE-HRFSGMKKSA-N 0.000 claims 1
- QJRLNLGIDHDESH-BHYZAODMSA-N (2s,3r)-5-methyl-3-phenylmethoxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]hexanoic acid Chemical compound O([C@H](CC(C)C)[C@H](NC(=O)C=1C(=CC2=CC=CC=C2C=1)NC(=O)NC=1C(=CC(C)=CC=1C)C)C(O)=O)CC1=CC=CC=C1 QJRLNLGIDHDESH-BHYZAODMSA-N 0.000 claims 1
- JEBJURUMASJIAQ-FYSMJZIKSA-N (2s,3s)-3-methyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]pentanoic acid Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C JEBJURUMASJIAQ-FYSMJZIKSA-N 0.000 claims 1
- JDTCKUHUGNMDMO-UHFFFAOYSA-N 1-[[3-[(2,4,6-trichlorophenyl)carbamoylamino]naphthalene-2-carbonyl]amino]cyclooctane-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C=C(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)Cl)C=1C(=O)NC1(C(=O)O)CCCCCCC1 JDTCKUHUGNMDMO-UHFFFAOYSA-N 0.000 claims 1
- MPLHHHQTYRDVCF-UHFFFAOYSA-N 1-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]cyclodecane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CCCCCCCCC1 MPLHHHQTYRDVCF-UHFFFAOYSA-N 0.000 claims 1
- VAJWMCGTGCHONC-UHFFFAOYSA-N 1-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]cycloheptane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CCCCCC1 VAJWMCGTGCHONC-UHFFFAOYSA-N 0.000 claims 1
- DRZBABLGPAMBFG-UHFFFAOYSA-N 1-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]cyclooctane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CCCCCCC1 DRZBABLGPAMBFG-UHFFFAOYSA-N 0.000 claims 1
- UJRUBHPTIIEYNO-UHFFFAOYSA-N 1-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]quinoline-2-carbonyl]amino]cycloheptane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2N=C1C(=O)NC1(C(O)=O)CCCCCC1 UJRUBHPTIIEYNO-UHFFFAOYSA-N 0.000 claims 1
- KWXSUGFRTXJSHR-UHFFFAOYSA-N 1-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]quinoline-2-carbonyl]amino]cyclooctane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2N=C1C(=O)NC1(C(O)=O)CCCCCCC1 KWXSUGFRTXJSHR-UHFFFAOYSA-N 0.000 claims 1
- ZWXILRKUZVGKGP-UHFFFAOYSA-N 1-[[3-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]cycloheptane-1-carboxylic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CCCCCC1 ZWXILRKUZVGKGP-UHFFFAOYSA-N 0.000 claims 1
- HTXTYVPZVFGFOJ-UHFFFAOYSA-N 1-[[4-phenyl-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]cyclooctane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1C(=O)NC1(C(O)=O)CCCCCCC1 HTXTYVPZVFGFOJ-UHFFFAOYSA-N 0.000 claims 1
- DCWCUNDOMWOEAM-UHFFFAOYSA-N 1-[[5-chloro-3-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]pyridine-2-carbonyl]amino]cyclooctane-1-carboxylic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(Cl)=CN=C1C(=O)NC1(C(O)=O)CCCCCCC1 DCWCUNDOMWOEAM-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- XAXCGSHRQAWXRM-UHFFFAOYSA-N 2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 XAXCGSHRQAWXRM-UHFFFAOYSA-N 0.000 claims 1
- ZWWWJKRNSRHDLG-UHFFFAOYSA-N 2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]-3,4-dihydro-1h-naphthalene-2-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2CC1 ZWWWJKRNSRHDLG-UHFFFAOYSA-N 0.000 claims 1
- LAAFMIUORMZKHU-UHFFFAOYSA-N 2-[[3-[[2,6-dichloro-4-(trifluoromethoxy)phenyl]carbamoylamino]naphthalene-2-carbonyl]amino]-2-(oxan-4-yl)acetic acid Chemical compound C1COCCC1C(C(=O)O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl LAAFMIUORMZKHU-UHFFFAOYSA-N 0.000 claims 1
- OPJGZTIWGHVQER-UHFFFAOYSA-N 2-phenyl-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)NC(C(O)=O)C1=CC=CC=C1 OPJGZTIWGHVQER-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 1
- SIUMSPJCTRJOLO-DJZALBQRSA-N OC(=O)C([C@@H]1CC[C@@H](CC1)C(F)(F)F)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl Chemical compound OC(=O)C([C@@H]1CC[C@@H](CC1)C(F)(F)F)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl SIUMSPJCTRJOLO-DJZALBQRSA-N 0.000 claims 1
- SIUMSPJCTRJOLO-XIDRFSJUSA-N OC(=O)C([C@@H]1CC[C@H](CC1)C(F)(F)F)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl Chemical compound OC(=O)C([C@@H]1CC[C@H](CC1)C(F)(F)F)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(Cl)C=C(OC(F)(F)F)C=C1Cl SIUMSPJCTRJOLO-XIDRFSJUSA-N 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960002989 glutamic acid Drugs 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US62638904P | 2004-11-09 | 2004-11-09 | |
| US60/626,389 | 2004-11-09 | ||
| PCT/US2005/039956 WO2006052722A1 (en) | 2004-11-09 | 2005-11-04 | Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof |
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| Publication Number | Publication Date |
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| RU2007119427A true RU2007119427A (ru) | 2008-12-20 |
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Family Applications (1)
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| RU2007119427/04A RU2007119427A (ru) | 2004-11-09 | 2005-11-04 | Соединения, являющиеся ингибиторами гликогенфосфорилазы, и фармацевтические композиции на их основе |
Country Status (16)
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| US (1) | US20070249670A1 (https=) |
| EP (1) | EP1812383A1 (https=) |
| JP (1) | JP2008519761A (https=) |
| KR (1) | KR20070086044A (https=) |
| CN (1) | CN101098852A (https=) |
| AU (2) | AU2005304962B2 (https=) |
| BR (1) | BRPI0517567A (https=) |
| CA (1) | CA2586446A1 (https=) |
| IL (1) | IL182863A0 (https=) |
| MA (1) | MA29090B1 (https=) |
| MX (1) | MX2007005590A (https=) |
| NO (1) | NO20072223L (https=) |
| RU (1) | RU2007119427A (https=) |
| SG (1) | SG155229A1 (https=) |
| WO (1) | WO2006052722A1 (https=) |
| ZA (1) | ZA200703713B (https=) |
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| JP4770213B2 (ja) * | 2004-03-22 | 2011-09-14 | 住友化学株式会社 | (2−ホルミル−1−アルケニル)シクロプロパン化合物の製造方法 |
| EP1676834A1 (en) | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| JP5352454B2 (ja) | 2006-06-28 | 2013-11-27 | サノフイ | Cxcr2アンンタゴニスト |
| EP2040690B1 (en) | 2006-06-28 | 2014-08-06 | Sanofi | Inhibitors of cxcr2 |
| CA2656150A1 (en) | 2006-06-28 | 2008-01-03 | Sanofi-Aventis | New cxcr2 inhibitors |
| JP5352455B2 (ja) * | 2006-06-30 | 2013-11-27 | サノフイ | Cxcr2阻害剤 |
| GB0619611D0 (en) * | 2006-10-04 | 2006-11-15 | Ark Therapeutics Ltd | Compounds and their use |
| DE102007012284A1 (de) | 2007-03-16 | 2008-09-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| DE102007035333A1 (de) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| DE102007035334A1 (de) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| KR20100087300A (ko) * | 2007-09-28 | 2010-08-04 | 글락소스미스클라인 엘엘씨 | 글리코겐 포스포릴라아제 억제제 화합물 및 이의 약학적 조성물 |
| CN101861303A (zh) * | 2007-09-28 | 2010-10-13 | 葛兰素史密丝克莱恩有限责任公司 | 糖原磷酸化酶抑制剂化合物和其药物组合物 |
| PT2303270T (pt) * | 2008-05-05 | 2017-08-25 | Sanofi Sa | Derivados fundidos do ácido ciclopentanocarboxílico substituídos por acilamino e sua utilização como produtos farmacêuticos |
| EP2299816B1 (en) * | 2008-06-18 | 2013-11-13 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| WO2010092440A1 (en) * | 2009-02-16 | 2010-08-19 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Cxcr2 receptor antagonists for the treatment or the prevention of insulin resistance |
| AR079022A1 (es) * | 2009-11-02 | 2011-12-21 | Sanofi Aventis | Derivados de acido carboxilico ciclico sustituidos con acilamino, su uso como productos farmaceuticos, composicion farmaceutica y metodo de preparacion |
| US8729114B2 (en) | 2010-03-05 | 2014-05-20 | Boehringer Ingelheim International Gmbh | Heteroaryl nitrile compounds useful as inhibitors of Cathepsin-S |
| WO2011159781A2 (en) * | 2010-06-17 | 2011-12-22 | Senomyx, Inc. | Bitter taste modulators |
| GB201211309D0 (en) * | 2012-06-26 | 2012-08-08 | Fujifilm Mfg Europe Bv | Process for preparing membranes |
| HUE032306T2 (en) | 2012-06-26 | 2017-09-28 | Bayer Pharma AG | N- [4- (quinolin-4-yloxy) cyclohexyl (methyl)] (hetero) arylcarboxamides as androgen receptor antagonists, their production and use as pharmaceutical products |
| MX388871B (es) | 2014-06-27 | 2025-03-20 | Nogra Pharma Ltd | Moduladores del receptor arilo y metodos para elaborar y usar los mismos. |
| EP3426674A4 (en) | 2016-03-09 | 2019-08-14 | Blade Therapeutics, Inc. | CYCLIC KETO AMID COMPOUNDS AS CALPAIN MODULATORS AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| AU2017292646A1 (en) | 2016-07-05 | 2019-02-07 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| WO2018064119A1 (en) | 2016-09-28 | 2018-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| EP3762379A1 (en) | 2018-03-07 | 2021-01-13 | Bayer Aktiengesellschaft | Identification and use of erk5 inhibitors |
| SG11202106444WA (en) | 2018-12-19 | 2021-07-29 | Leo Pharma As | Amino-acid anilides as small molecule modulators of il-17 |
| WO2020234103A1 (en) | 2019-05-21 | 2020-11-26 | Bayer Aktiengesellschaft | Identification and use of kras inhibitors |
| WO2021152113A1 (en) | 2020-01-31 | 2021-08-05 | Bayer Aktiengesellschaft | Substituted 2,3-benzodiazepines derivatives |
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| JPS59181257A (ja) * | 1983-03-31 | 1984-10-15 | Chugai Pharmaceut Co Ltd | ウレイドベンズアミド誘導体 |
| JPS61268678A (ja) * | 1985-05-17 | 1986-11-28 | バイエル・アクチエンゲゼルシヤフト | 生産増進剤 |
| US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
| BR9611820A (pt) * | 1995-11-24 | 1999-07-13 | Smithkline Beecham Spa | Derivados de quinolina |
| CA2255858C (en) * | 1996-05-24 | 2007-09-11 | Neurosearch A/S | Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers |
| DE69826695T2 (de) * | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
| US6093742A (en) * | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| US7125875B2 (en) * | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| ES2288871T3 (es) * | 1999-09-24 | 2008-02-01 | Genentech, Inc. | Derivados de tirosina. |
| GB0008264D0 (en) * | 2000-04-04 | 2000-05-24 | Smithkline Beecham Plc | Novel method and compounds |
| US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| AU2003265398A1 (en) * | 2002-08-09 | 2004-02-25 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| AU2003258491A1 (en) * | 2002-09-05 | 2004-03-29 | Neurosearch A/S | Amide derivatives and their use as chloride channel blockers |
| PT1565429E (pt) * | 2002-11-21 | 2009-07-23 | Neurosearch As | Derivados de diaril-ureído e sua utilização médica |
| WO2005023818A2 (en) * | 2003-09-10 | 2005-03-17 | Gpc Biotech Ag | Heterobicyclic compounds as pharmaceutically active agents |
| US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| CA2563432A1 (en) * | 2004-04-16 | 2005-12-01 | Genentech, Inc. | Method for augmenting b cell depletion |
-
2005
- 2005-11-04 SG SG200905516-1A patent/SG155229A1/en unknown
- 2005-11-04 JP JP2007540066A patent/JP2008519761A/ja active Pending
- 2005-11-04 RU RU2007119427/04A patent/RU2007119427A/ru not_active Application Discontinuation
- 2005-11-04 CA CA002586446A patent/CA2586446A1/en not_active Abandoned
- 2005-11-04 WO PCT/US2005/039956 patent/WO2006052722A1/en not_active Ceased
- 2005-11-04 KR KR1020077013158A patent/KR20070086044A/ko not_active Withdrawn
- 2005-11-04 BR BRPI0517567-4A patent/BRPI0517567A/pt not_active IP Right Cessation
- 2005-11-04 CN CNA2005800462669A patent/CN101098852A/zh active Pending
- 2005-11-04 EP EP05839433A patent/EP1812383A1/en not_active Withdrawn
- 2005-11-04 MX MX2007005590A patent/MX2007005590A/es not_active Application Discontinuation
- 2005-11-04 US US11/718,804 patent/US20070249670A1/en not_active Abandoned
- 2005-11-04 AU AU2005304962A patent/AU2005304962B2/en not_active Ceased
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2007
- 2007-04-30 IL IL182863A patent/IL182863A0/en unknown
- 2007-04-30 NO NO20072223A patent/NO20072223L/no not_active Application Discontinuation
- 2007-05-08 ZA ZA200703713A patent/ZA200703713B/xx unknown
- 2007-06-08 MA MA29978A patent/MA29090B1/fr unknown
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2010
- 2010-02-12 AU AU2010200531A patent/AU2010200531A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070086044A (ko) | 2007-08-27 |
| AU2010200531A1 (en) | 2010-03-04 |
| AU2005304962B2 (en) | 2009-11-19 |
| CA2586446A1 (en) | 2006-05-18 |
| WO2006052722A1 (en) | 2006-05-18 |
| CN101098852A (zh) | 2008-01-02 |
| IL182863A0 (en) | 2007-08-19 |
| BRPI0517567A (pt) | 2008-06-17 |
| JP2008519761A (ja) | 2008-06-12 |
| AU2005304962A1 (en) | 2006-05-18 |
| SG155229A1 (en) | 2009-09-30 |
| EP1812383A1 (en) | 2007-08-01 |
| ZA200703713B (en) | 2008-10-29 |
| NO20072223L (no) | 2007-06-25 |
| US20070249670A1 (en) | 2007-10-25 |
| MX2007005590A (es) | 2007-05-24 |
| MA29090B1 (fr) | 2007-12-03 |
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