KR20070086044A - 글리코겐 포스포릴라제 억제제 화합물 및 이의 약제학적조성물 - Google Patents
글리코겐 포스포릴라제 억제제 화합물 및 이의 약제학적조성물 Download PDFInfo
- Publication number
- KR20070086044A KR20070086044A KR1020077013158A KR20077013158A KR20070086044A KR 20070086044 A KR20070086044 A KR 20070086044A KR 1020077013158 A KR1020077013158 A KR 1020077013158A KR 20077013158 A KR20077013158 A KR 20077013158A KR 20070086044 A KR20070086044 A KR 20070086044A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- carbonyl
- trimethylphenyl
- cyclohexyl
- acid
- 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.)
- Withdrawn
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 29
- ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical class CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 207
- 238000000034 method Methods 0.000 claims abstract description 91
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 208000028867 ischemia Diseases 0.000 claims abstract description 9
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 9
- -1 (2S) -cyclohexyl [(3-{[(methylamino) carbonyl] amino} -2-naphthoyl) amino] ethanoic acid Chemical compound 0.000 claims description 194
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 192
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 71
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 71
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
- 239000011593 sulfur Substances 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 235000011054 acetic acid Nutrition 0.000 claims description 26
- 229960000583 acetic acid Drugs 0.000 claims description 26
- 229960005261 aspartic acid Drugs 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 241000124008 Mammalia Species 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 15
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 14
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 229960003767 alanine Drugs 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229960004295 valine Drugs 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 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 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 238000010532 solid phase synthesis reaction Methods 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims description 6
- 229960001153 serine Drugs 0.000 claims description 6
- LFBWDMNWTUNNBD-SFHVURJKSA-N (2s)-2-[[4-chloro-2-[(2,6-dichlorophenyl)carbamoylamino]benzoyl]amino]-2-cyclohexylacetic acid Chemical compound N([C@H](C(=O)O)C1CCCCC1)C(=O)C1=CC=C(Cl)C=C1NC(=O)NC1=C(Cl)C=CC=C1Cl LFBWDMNWTUNNBD-SFHVURJKSA-N 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229960004717 insulin aspart Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 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 description 4
- 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 description 4
- GDLZHARWVNMOAT-LJAQVGFWSA-N (2s)-2-cyclohexyl-2-[[4-[4-(hydroxymethyl)phenyl]-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(CO)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 GDLZHARWVNMOAT-LJAQVGFWSA-N 0.000 claims description 4
- 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 description 4
- 239000012071 phase Substances 0.000 claims description 4
- 229960002429 proline Drugs 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- KIWJETGZXOFSTF-NDEPHWFRSA-N (2s)-2-[[4-(4-aminophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-2-cyclohexylacetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(N)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 KIWJETGZXOFSTF-NDEPHWFRSA-N 0.000 claims description 3
- PGYQCNLAPKDSQL-MHZLTWQESA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-(4-hydroxyphenyl)benzoyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(O)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 PGYQCNLAPKDSQL-MHZLTWQESA-N 0.000 claims description 3
- 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 description 3
- FRUWRBBENKXVAY-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[3-[(2-ethyl-6-methylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CCC1=CC=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 FRUWRBBENKXVAY-SANMLTNESA-N 0.000 claims description 3
- 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 description 3
- RANVARGNLMCBAO-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-phenyl-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 RANVARGNLMCBAO-NDEPHWFRSA-N 0.000 claims description 3
- 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 description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 239000004474 valine Substances 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XPIDIBFCJYTFNR-QFIPXVFZSA-N (2s)-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]hexanoic acid Chemical compound CCCC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C XPIDIBFCJYTFNR-QFIPXVFZSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- QYXHHWFPIGFUQX-LJAQVGFWSA-N (2s)-2-[[4-(1,3-benzodioxol-5-yl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-2-cyclohexylacetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C3OCOC3=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 QYXHHWFPIGFUQX-LJAQVGFWSA-N 0.000 claims description 2
- CUCNQGCEFVZELP-LJAQVGFWSA-N (2s)-2-[[4-(3,4-difluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-3-phenylmethoxypropanoic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C(F)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)COCC1=CC=CC=C1 CUCNQGCEFVZELP-LJAQVGFWSA-N 0.000 claims description 2
- SASYKTGXXUGBSV-QFIPXVFZSA-N (2s)-2-[[4-(3,4-difluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]pentanedioic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C(F)=CC=2)=CC=C1C(=O)N[C@@H](CCC(O)=O)C(O)=O SASYKTGXXUGBSV-QFIPXVFZSA-N 0.000 claims description 2
- LFKHAUUIVVVVKJ-QFIPXVFZSA-N (2s)-2-[[4-(3-fluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]butanedioic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C=CC=2)=CC=C1C(=O)N[C@@H](CC(O)=O)C(O)=O LFKHAUUIVVVVKJ-QFIPXVFZSA-N 0.000 claims description 2
- CFPVNZFFYYCHRF-QFIPXVFZSA-N (2s)-2-[[4-chloro-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-2-cyclohexylacetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(Cl)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 CFPVNZFFYYCHRF-QFIPXVFZSA-N 0.000 claims description 2
- SFHQXACIYMBHFX-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[2-(3,5-difluorophenyl)-6-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC=CC(C=2C=C(F)C=C(F)C=2)=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 SFHQXACIYMBHFX-NDEPHWFRSA-N 0.000 claims description 2
- IQADTMZJCRQGCR-DEOSSOPVSA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dichlorophenyl)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=CC=C1Cl IQADTMZJCRQGCR-DEOSSOPVSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- HICPAGRDRIYRQS-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-pyridin-3-ylbenzoyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(C=2C=NC=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 HICPAGRDRIYRQS-SANMLTNESA-N 0.000 claims description 2
- DIEDGCBBMJVTTQ-VWLOTQADSA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-thiophen-2-ylbenzoyl]amino]acetic acid Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(C=2SC=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DIEDGCBBMJVTTQ-VWLOTQADSA-N 0.000 claims description 2
- 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 description 2
- MUCCBKDQNOJJGB-XIFFEERXSA-N (2s)-2-cyclohexyl-2-[[2-[4-(morpholin-4-ylmethyl)phenyl]-6-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC=CC(C=2C=CC(CN3CCOCC3)=CC=2)=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 MUCCBKDQNOJJGB-XIFFEERXSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
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- ITMPBHYELVUTFU-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[4,5-difluoro-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(F)=C(F)C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 ITMPBHYELVUTFU-QFIPXVFZSA-N 0.000 claims description 2
- DMOWCCDOITZYJJ-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(3,4-difluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C(F)C(F)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DMOWCCDOITZYJJ-NDEPHWFRSA-N 0.000 claims description 2
- RPXKOHXBOMZWAY-PMERELPUSA-N (2s)-2-cyclohexyl-2-[[4-(3,4-dimethoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 RPXKOHXBOMZWAY-PMERELPUSA-N 0.000 claims description 2
- RPXAYTMEEUZRSD-QHCPKHFHSA-N (2s)-2-cyclohexyl-2-[[4-(methylcarbamoylamino)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1([C@H](NC(=O)C2=CC=C(C=C2NC(=O)NC=2C(=CC(C)=CC=2C)C)NC(=O)NC)C(O)=O)CCCCC1 RPXAYTMEEUZRSD-QHCPKHFHSA-N 0.000 claims description 2
- 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 description 2
- QVJHMRWWDUKACM-DEOSSOPVSA-N (2s)-3-(2,2-dimethylpropoxy)-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](COCC(C)(C)C)C(O)=O QVJHMRWWDUKACM-DEOSSOPVSA-N 0.000 claims description 2
- AXPIVZSOTIKADO-QHCPKHFHSA-N (2s)-3-[(2-methylpropan-2-yl)oxy]-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](COC(C)(C)C)C(O)=O AXPIVZSOTIKADO-QHCPKHFHSA-N 0.000 claims description 2
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- SAKQSQBEWSFYSX-QFIPXVFZSA-N (2s)-3-ethoxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]propanoic acid Chemical compound CCOC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C SAKQSQBEWSFYSX-QFIPXVFZSA-N 0.000 claims description 2
- 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 description 2
- FAGQAOSDDQAHTM-MHZLTWQESA-N (2s)-3-phenylmethoxy-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)COCC1=CC=CC=C1 FAGQAOSDDQAHTM-MHZLTWQESA-N 0.000 claims description 2
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- NJOWKXJPMUAHSG-QHCPKHFHSA-N (2s)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanoic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@@H](CCNC(=O)OC(C)(C)C)C(O)=O NJOWKXJPMUAHSG-QHCPKHFHSA-N 0.000 claims description 2
- CMHSYKMWGNHXKV-QHCPKHFHSA-N (2s)-4-amino-2-[[4-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-4-oxobutanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)N[C@@H](CC(N)=O)C(O)=O)C(NC(=O)NC=2C(=CC(C)=CC=2C)C)=C1 CMHSYKMWGNHXKV-QHCPKHFHSA-N 0.000 claims description 2
- 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 description 2
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- LKYWLZDWXVGLMW-NRFANRHFSA-N (2s)-6,6,6-trifluoro-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]hexanoic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@@H](CCCC(F)(F)F)C(O)=O LKYWLZDWXVGLMW-NRFANRHFSA-N 0.000 claims description 2
- PFGYDXPDGSRGMN-RCRUUEGKSA-N (2s,3r)-2-[[2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]-4-(4-methoxyphenyl)benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound CC1=CC(CCC)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(OC)=CC=2)=CC=C1C(=O)N[C@@H]([C@@H](C)OC(C)(C)C)C(O)=O PFGYDXPDGSRGMN-RCRUUEGKSA-N 0.000 claims description 2
- 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 description 2
- IVTWTRKNKDMKHF-WINIVTDRSA-N (2s,3r)-2-[[4-(3,4-difluorophenyl)-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=C(F)C(F)=CC=2)C=C1NC(=O)NC1=C(C)C=C(C)C=C1C IVTWTRKNKDMKHF-WINIVTDRSA-N 0.000 claims description 2
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- KNXPXTCHVCTQBO-GDJIYFAZSA-N (2s,3r)-3-cyclobutyloxy-2-[[4-(3,4-difluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]butanoic acid Chemical compound O([C@H](C)[C@H](NC(=O)C=1C(=CC(=CC=1)C=1C=C(F)C(F)=CC=1)NC(=O)NC=1C(=CC(C)=CC=1C)C)C(O)=O)C1CCC1 KNXPXTCHVCTQBO-GDJIYFAZSA-N 0.000 claims description 2
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- IIDMMNYHKOGXAY-NDEPHWFRSA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-(4-hydroxyphenyl)benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C=2C=CC(O)=CC=2)C=C1NC(=O)NC1=C(C)C=CC=C1C IIDMMNYHKOGXAY-NDEPHWFRSA-N 0.000 description 1
- IHYXOFKBQZAFLE-QFIPXVFZSA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-fluorobenzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(F)C=C1NC(=O)NC1=C(C)C=CC=C1C IHYXOFKBQZAFLE-QFIPXVFZSA-N 0.000 description 1
- NROQPRHPPPFNAK-MHZLTWQESA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-pyridin-3-ylbenzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C=2C=NC=CC=2)C=C1NC(=O)NC1=C(C)C=CC=C1C NROQPRHPPPFNAK-MHZLTWQESA-N 0.000 description 1
- DNTPPIWQXLYHQU-SANMLTNESA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-thiophen-2-ylbenzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C=2SC=CC=2)C=C1NC(=O)NC1=C(C)C=CC=C1C DNTPPIWQXLYHQU-SANMLTNESA-N 0.000 description 1
- GZADQZFQWBWLSQ-SANMLTNESA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-thiophen-3-ylbenzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C2=CSC=C2)C=C1NC(=O)NC1=C(C)C=CC=C1C GZADQZFQWBWLSQ-SANMLTNESA-N 0.000 description 1
- VESUHRLCUXSHLL-QHCPKHFHSA-N methyl (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-5-methylbenzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC(C)=CC=C1NC(=O)NC1=C(C)C=CC=C1C VESUHRLCUXSHLL-QHCPKHFHSA-N 0.000 description 1
- NJUOOWAJUKDSGG-SANMLTNESA-N methyl (2s)-2-cyclohexyl-2-[[3-[[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]acetyl]amino]naphthalene-2-carbonyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC2=CC=CC=C2C=C1NC(=O)CC1=C(Cl)C=C(C(F)(F)F)C=C1Cl NJUOOWAJUKDSGG-SANMLTNESA-N 0.000 description 1
- XMABVAIVYKXXII-IBGZPJMESA-N methyl (2s)-2-cyclohexyl-2-[[4,5-dichloro-2-[(2,6-dichlorophenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC(Cl)=C(Cl)C=C1NC(=O)NC1=C(Cl)C=CC=C1Cl XMABVAIVYKXXII-IBGZPJMESA-N 0.000 description 1
- SUWUXLREXZJMSI-QFIPXVFZSA-N methyl (2s)-2-cyclohexyl-2-[[4,5-dichloro-2-[(2,6-dimethylphenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC(Cl)=C(Cl)C=C1NC(=O)NC1=C(C)C=CC=C1C SUWUXLREXZJMSI-QFIPXVFZSA-N 0.000 description 1
- FCGJLIFGMWUZDF-NDEPHWFRSA-N methyl (2s)-2-cyclohexyl-2-[[4-(3,4-difluorophenyl)-2-[(2,6-dimethylphenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C=2C=C(F)C(F)=CC=2)C=C1NC(=O)NC1=C(C)C=CC=C1C FCGJLIFGMWUZDF-NDEPHWFRSA-N 0.000 description 1
- PFCWDFCITHNJLE-QHCPKHFHSA-N methyl (2s)-2-cyclohexyl-2-[[4-fluoro-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(F)C=C1NC(=O)NC1=C(C)C=C(C)C=C1C PFCWDFCITHNJLE-QHCPKHFHSA-N 0.000 description 1
- ZPWAYYSXNRMQLM-NDEPHWFRSA-N methyl (2s)-2-cyclohexyl-2-[[4-phenyl-2-[[2-(2,4,6-trichlorophenyl)acetyl]amino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC)C1CCCCC1)C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)CC1=C(Cl)C=C(Cl)C=C1Cl ZPWAYYSXNRMQLM-NDEPHWFRSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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- VJMRKWPMFQGIPI-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide Chemical compound OCC1=C(C(=O)NCCO)C(C)=NN1C1=CC=CC2=C1SC(CC=1C=C(C=CC=1)C(F)(F)F)=C2 VJMRKWPMFQGIPI-UHFFFAOYSA-N 0.000 description 1
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- RAFVKOLBEOKYJW-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Cl)=CN=C1C(=O)NC1=CC=C(F)C([C@@]2(C)N=C(N)COC2)=C1 RAFVKOLBEOKYJW-SFHVURJKSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
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- AZSRSNUQCUDCGG-UHFFFAOYSA-N propan-2-yl 2-[4-[2-(dimethylamino)ethyl-methylamino]-2-methoxy-5-(prop-2-enoylamino)anilino]-4-(1-methylindol-3-yl)pyrimidine-5-carboxylate Chemical compound C(C=C)(=O)NC=1C(=CC(=C(C=1)NC1=NC=C(C(=N1)C1=CN(C2=CC=CC=C12)C)C(=O)OC(C)C)OC)N(C)CCN(C)C AZSRSNUQCUDCGG-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FIKPXCOQUIZNHB-WDEREUQCSA-N repotrectinib Chemical compound C[C@H]1CNC(=O)C2=C3N=C(N[C@H](C)C4=C(O1)C=CC(F)=C4)C=CN3N=C2 FIKPXCOQUIZNHB-WDEREUQCSA-N 0.000 description 1
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- 229940113147 shellac Drugs 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- UJJXKFMLCCUOHE-INIZCTEOSA-N tert-butyl (2s)-2-[(2-amino-4-chlorobenzoyl)amino]-2-cyclohexylacetate Chemical compound N([C@H](C(=O)OC(C)(C)C)C1CCCCC1)C(=O)C1=CC=C(Cl)C=C1N UJJXKFMLCCUOHE-INIZCTEOSA-N 0.000 description 1
- UJJAWDIVYGHFGD-YTTGMZPUSA-N tert-butyl (2s)-2-cyclohexyl-2-[[4-[4-(hydroxymethyl)phenyl]-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(CO)=CC=2)=CC=C1C(=O)N[C@H](C(=O)OC(C)(C)C)C1CCCCC1 UJJAWDIVYGHFGD-YTTGMZPUSA-N 0.000 description 1
- HCBYAENZNFELCN-MHZLTWQESA-N tert-butyl (2s)-2-cyclohexyl-2-[[4-phenyl-2-[(2,4,6-trichlorophenyl)carbamoylamino]benzoyl]amino]acetate Chemical compound N([C@H](C(=O)OC(C)(C)C)C1CCCCC1)C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl HCBYAENZNFELCN-MHZLTWQESA-N 0.000 description 1
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- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
-
- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62638904P | 2004-11-09 | 2004-11-09 | |
| US60/626,389 | 2004-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070086044A true KR20070086044A (ko) | 2007-08-27 |
Family
ID=35976487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077013158A Withdrawn KR20070086044A (ko) | 2004-11-09 | 2005-11-04 | 글리코겐 포스포릴라제 억제제 화합물 및 이의 약제학적조성물 |
Country Status (16)
| Country | Link |
|---|---|
| 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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| JP4765353B2 (ja) * | 2004-03-22 | 2011-09-07 | 住友化学株式会社 | (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 |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| JP5232144B2 (ja) | 2006-06-28 | 2013-07-10 | サノフイ | Cxcr2阻害剤 |
| WO2008000408A1 (en) | 2006-06-28 | 2008-01-03 | Sanofi-Aventis | Cxcr2 antagonists |
| KR20090023645A (ko) | 2006-06-28 | 2009-03-05 | 사노피-아벤티스 | 신규한 cxcr2 억제제 |
| 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 |
| DE102007035334A1 (de) | 2007-07-27 | 2009-01-29 | 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 |
| KR20100087300A (ko) * | 2007-09-28 | 2010-08-04 | 글락소스미스클라인 엘엘씨 | 글리코겐 포스포릴라아제 억제제 화합물 및 이의 약학적 조성물 |
| KR20100075568A (ko) * | 2007-09-28 | 2010-07-02 | 글락소스미스클라인 엘엘씨 | 글리코겐 포스포릴라아제 억제제 화합물 및 이의 약제 조성물 |
| RU2529484C2 (ru) * | 2008-05-05 | 2014-09-27 | Санофи-Авентис | Ациламино-замещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств |
| WO2009155156A1 (en) * | 2008-06-18 | 2009-12-23 | Merck & Co., Inc. | 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 |
| WO2011109470A1 (en) | 2010-03-05 | 2011-09-09 | 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 |
| SI2864291T1 (sl) | 2012-06-26 | 2017-01-31 | Bayer Pharma Aktiengesellschaft | N-(4-(kinolin-4-iloksi)cikloheksil(metil))(hetero)arilkarboksamidi kot antagonisti receptorja androgena, njihova izdelava in uporaba kot medicinski izdelki |
| GB201211309D0 (en) * | 2012-06-26 | 2012-08-08 | Fujifilm Mfg Europe Bv | Process for preparing membranes |
| CN111978319B (zh) | 2014-06-27 | 2023-08-11 | 诺格拉制药有限公司 | 芳基受体调制剂及其制备和使用方法 |
| WO2017156071A1 (en) | 2016-03-09 | 2017-09-14 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| EP3481835A4 (en) | 2016-07-05 | 2020-02-26 | Blade Therapeutics, Inc. | CALPAIN MODULATORS AND THERAPEUTIC USE THEREOF |
| BR112019006110A2 (pt) | 2016-09-28 | 2019-09-10 | Blade Therapeutics Inc | moduladores de calpaína e usos terapêuticos dos mesmos |
| JP2021515767A (ja) | 2018-03-07 | 2021-06-24 | バイエル・アクチエンゲゼルシヤフト | Erk5阻害剤の同定及び使用 |
| BR112021010453A2 (pt) | 2018-12-19 | 2021-08-24 | Leo Pharma A/S | Composto, e, composição farmacêutica |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| EA002124B1 (ru) * | 1995-11-24 | 2001-12-24 | Смитклайн Бичам С.П.А. | Производные хинолина |
| US6417393B1 (en) * | 1996-05-24 | 2002-07-09 | Neurosearch A/S | Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers |
| WO1998052558A1 (en) * | 1997-05-23 | 1998-11-26 | Bayer Corporation | INHIBITION OF p38 KINASE ACTIVITY BY ARYL UREAS |
| 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 |
| CA2385882C (en) * | 1999-09-24 | 2009-11-24 | Genentech, Inc. | Tyrosine derivatives |
| 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 |
| JP2005535710A (ja) * | 2002-08-09 | 2005-11-24 | トランス テック ファーマ,インコーポレイテッド | アリールおよびヘテロアリール化合物ならびに凝固を調節する方法 |
| AU2003258491A1 (en) * | 2002-09-05 | 2004-03-29 | Neurosearch A/S | Amide derivatives and their use as chloride channel blockers |
| JP2006507329A (ja) * | 2002-11-21 | 2006-03-02 | ニューロサーチ、アクティーゼルスカブ | 新規アリールウレイド安息香酸誘導体及びその使用 |
| EP1670804A2 (en) * | 2003-09-10 | 2006-06-21 | 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 |
| BRPI0508762A (pt) * | 2004-04-16 | 2007-08-14 | Genentech Inc | método de aumento do esgotamento de células b em mamìferos, método de aumento da eficácia do esgotamento de células b, método de tratamento de malignidade ou neoplasma de células b, método de alìvio de disfunção autoimunológica regulada por células b, método de esgotamento das células b e composição |
-
2005
- 2005-11-04 AU AU2005304962A patent/AU2005304962B2/en not_active Ceased
- 2005-11-04 KR KR1020077013158A patent/KR20070086044A/ko not_active Withdrawn
- 2005-11-04 CN CNA2005800462669A patent/CN101098852A/zh active Pending
- 2005-11-04 US US11/718,804 patent/US20070249670A1/en not_active Abandoned
- 2005-11-04 JP JP2007540066A patent/JP2008519761A/ja active Pending
- 2005-11-04 BR BRPI0517567-4A patent/BRPI0517567A/pt not_active IP Right Cessation
- 2005-11-04 RU RU2007119427/04A patent/RU2007119427A/ru not_active Application Discontinuation
- 2005-11-04 EP EP05839433A patent/EP1812383A1/en not_active Withdrawn
- 2005-11-04 WO PCT/US2005/039956 patent/WO2006052722A1/en not_active Ceased
- 2005-11-04 SG SG200905516-1A patent/SG155229A1/en unknown
- 2005-11-04 CA CA002586446A patent/CA2586446A1/en not_active Abandoned
- 2005-11-04 MX MX2007005590A patent/MX2007005590A/es not_active Application Discontinuation
-
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
-
2010
- 2010-02-12 AU AU2010200531A patent/AU2010200531A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1812383A1 (en) | 2007-08-01 |
| SG155229A1 (en) | 2009-09-30 |
| US20070249670A1 (en) | 2007-10-25 |
| AU2005304962B2 (en) | 2009-11-19 |
| AU2005304962A1 (en) | 2006-05-18 |
| AU2010200531A1 (en) | 2010-03-04 |
| CN101098852A (zh) | 2008-01-02 |
| MA29090B1 (fr) | 2007-12-03 |
| WO2006052722A1 (en) | 2006-05-18 |
| BRPI0517567A (pt) | 2008-06-17 |
| ZA200703713B (en) | 2008-10-29 |
| IL182863A0 (en) | 2007-08-19 |
| MX2007005590A (es) | 2007-05-24 |
| CA2586446A1 (en) | 2006-05-18 |
| NO20072223L (no) | 2007-06-25 |
| RU2007119427A (ru) | 2008-12-20 |
| JP2008519761A (ja) | 2008-06-12 |
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| PA0105 | International application |
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| PC1203 | Withdrawal of no request for examination | ||
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