JP2008519761A5 - - Google Patents
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- Publication number
- JP2008519761A5 JP2008519761A5 JP2007540066A JP2007540066A JP2008519761A5 JP 2008519761 A5 JP2008519761 A5 JP 2008519761A5 JP 2007540066 A JP2007540066 A JP 2007540066A JP 2007540066 A JP2007540066 A JP 2007540066A JP 2008519761 A5 JP2008519761 A5 JP 2008519761A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- carbonyl
- trimethylphenyl
- cyclohexyl
- naphthalenyl
- 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.)
- Pending
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- -1 monoalkylamino Chemical group 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 206010012601 diabetes mellitus Diseases 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 239000011593 sulfur Substances 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229960000583 acetic acid Drugs 0.000 claims 5
- 235000011054 acetic acid Nutrition 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 208000031225 myocardial ischemia Diseases 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 239000012071 phase Substances 0.000 claims 3
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims 3
- 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 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 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
- LIZOXYKWJKVDDH-DCFJUCRTSA-N (2s)-2-[(1s)-3-(2,2,2-trifluoroacetyl)oxycyclohexyl]-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(OC(=O)C(F)(F)F)CCC1 LIZOXYKWJKVDDH-DCFJUCRTSA-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
- RKNQDZDZMOLAKM-VWLOTQADSA-N (2s)-2-[[2-[(2,6-dimethyl-4-propylphenyl)carbamoylamino]-4-(4-methoxyphenyl)benzoyl]amino]butanedioic 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)=O)C(O)=O RKNQDZDZMOLAKM-VWLOTQADSA-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
- 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 1
- 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 1
- GMSCZYHVBGWKON-QFIPXVFZSA-N (2s)-2-[[4-(3,4-difluorophenyl)-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(F)=CC=2)=CC=C1C(=O)N[C@@H](CC(O)=O)C(O)=O GMSCZYHVBGWKON-QFIPXVFZSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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
- 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 1
- KVTBKJCDPJYANX-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[2-[(2,6-dimethylphenyl)carbamoylamino]-4-(4-methoxyphenyl)benzoyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 KVTBKJCDPJYANX-NDEPHWFRSA-N 0.000 claims 1
- 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 1
- 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 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
- SYEKIFOUPHJXCG-QFIPXVFZSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dichlorophenyl)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=CC=C1Cl SYEKIFOUPHJXCG-QFIPXVFZSA-N 0.000 claims 1
- XONCYHAPPIBUKH-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[3-[(2,6-dimethyl-4-prop-2-ynylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]acetic acid Chemical compound CC1=CC(CC#C)=CC(C)=C1NC(=O)NC1=CC2=CC=CC=C2C=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 XONCYHAPPIBUKH-NDEPHWFRSA-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
- 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 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
- 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 1
- ITUVUCREFUHNBJ-PMERELPUSA-N (2s)-2-cyclohexyl-2-[[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=C3OCCOC3=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 ITUVUCREFUHNBJ-PMERELPUSA-N 0.000 claims 1
- MCWGNZNJWXNKDV-LJAQVGFWSA-N (2s)-2-cyclohexyl-2-[[4-(2-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound COC1=CC=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 MCWGNZNJWXNKDV-LJAQVGFWSA-N 0.000 claims 1
- 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 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
- BMJZYZUKEQVVEN-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(3,5-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=C(F)C=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 BMJZYZUKEQVVEN-NDEPHWFRSA-N 0.000 claims 1
- UJXZWSAODAPADZ-LJAQVGFWSA-N (2s)-2-cyclohexyl-2-[[4-(3-fluoro-4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1=C(F)C(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 UJXZWSAODAPADZ-LJAQVGFWSA-N 0.000 claims 1
- ONOSOIBRVHMGLZ-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(3-fluorophenyl)-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=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 ONOSOIBRVHMGLZ-NDEPHWFRSA-N 0.000 claims 1
- HRRGFUVVUDNBSU-PMERELPUSA-N (2s)-2-cyclohexyl-2-[[4-(4-ethoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1=CC(OCC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 HRRGFUVVUDNBSU-PMERELPUSA-N 0.000 claims 1
- DALZSBPUIWECHY-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(4-fluorophenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(F)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 DALZSBPUIWECHY-NDEPHWFRSA-N 0.000 claims 1
- CYBPMXLZLWLVFL-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(4-hydroxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC(C=2C=CC(O)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 CYBPMXLZLWLVFL-NDEPHWFRSA-N 0.000 claims 1
- MGZSKJCXSQIRJH-LJAQVGFWSA-N (2s)-2-cyclohexyl-2-[[4-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 MGZSKJCXSQIRJH-LJAQVGFWSA-N 0.000 claims 1
- CFLWXFAONAHSJO-NDEPHWFRSA-N (2s)-2-cyclohexyl-2-[[4-(4-nitrophenyl)-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)[N+]([O-])=O)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 CFLWXFAONAHSJO-NDEPHWFRSA-N 0.000 claims 1
- 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 1
- 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 1
- GZKWEHNDMLXCBL-XIFFEERXSA-N (2s)-2-cyclohexyl-2-[[4-[4-(morpholin-4-ylmethyl)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(CN3CCOCC3)=CC=2)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 GZKWEHNDMLXCBL-XIFFEERXSA-N 0.000 claims 1
- 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 1
- KNBGXIUPPHHIEL-SANMLTNESA-N (2s)-2-cyclohexyl-2-[[5-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]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(C)C=C(C)C=C1C KNBGXIUPPHHIEL-SANMLTNESA-N 0.000 claims 1
- IQXVKKFYLNUKKT-MHZLTWQESA-N (2s)-2-cyclohexyl-2-[[5-(4-methoxyphenyl)-3-[(2,4,6-trimethylphenyl)carbamoylamino]pyridine-2-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CN=C1C(=O)N[C@H](C(O)=O)C1CCCCC1 IQXVKKFYLNUKKT-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
- DITODIXMFAWTSZ-NDEPHWFRSA-N (2s)-2-cyclopentyl-2-[[4-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)N[C@H](C(O)=O)C1CCCC1 DITODIXMFAWTSZ-NDEPHWFRSA-N 0.000 claims 1
- 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 1
- 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 1
- GQUSZXYYGWDYMM-DEOSSOPVSA-N (2s)-3-butoxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]propanoic acid Chemical compound CCCCOC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C GQUSZXYYGWDYMM-DEOSSOPVSA-N 0.000 claims 1
- 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 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
- 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 1
- QTDVWQHIDOETGM-QHCPKHFHSA-N (2s)-3-propan-2-yloxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]propanoic acid Chemical compound CC(C)OC[C@@H](C(O)=O)NC(=O)C1=CC2=CC=CC=C2C=C1NC(=O)NC1=C(C)C=C(C)C=C1C QTDVWQHIDOETGM-QHCPKHFHSA-N 0.000 claims 1
- 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 1
- 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 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
- XBFMTTUCRNKMFV-QHCPKHFHSA-N (2s)-5,5-dimethyl-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](CCC(C)(C)C)C(O)=O XBFMTTUCRNKMFV-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
- 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 1
- 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 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
- HZMNQIFWFLFAFN-PIKZIKFNSA-N (2s,3r)-2-[[4-(2-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(=O)N[C@@H]([C@@H](C)OC(C)(C)C)C(O)=O)C(NC(=O)NC=2C(=CC(C)=CC=2C)C)=C1 HZMNQIFWFLFAFN-PIKZIKFNSA-N 0.000 claims 1
- 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 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
- WUFIMPRWQDXAMW-HRFSGMKKSA-N (2s,3r)-2-[[4-(3-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=C(F)C=CC=2)C=C1NC(=O)NC1=C(C)C=C(C)C=C1C WUFIMPRWQDXAMW-HRFSGMKKSA-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
- ZYAQEXLNQYIHNU-PIKZIKFNSA-N (2s,3r)-2-[[4-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]-3-[(2-methylpropan-2-yl)oxy]butanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)N[C@@H]([C@@H](C)OC(C)(C)C)C(O)=O)C(NC(=O)NC=2C(=CC(C)=CC=2C)C)=C1 ZYAQEXLNQYIHNU-PIKZIKFNSA-N 0.000 claims 1
- RIGBHLHCQZPKQJ-ZBLYBZFDSA-N (2s,3r)-3-(1-methylcyclopentyl)oxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanoic acid Chemical compound O([C@H](C)[C@H](NC(=O)C=1C(=CC2=CC=CC=C2C=1)NC(=O)NC=1C(=CC(C)=CC=1C)C)C(O)=O)C1(C)CCCC1 RIGBHLHCQZPKQJ-ZBLYBZFDSA-N 0.000 claims 1
- SIVVDUDKHBTSKI-CLOONOSVSA-N (2s,3r)-3-[(2-methylpropan-2-yl)oxy]-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]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)NC1=C(C)C=C(C)C=C1C SIVVDUDKHBTSKI-CLOONOSVSA-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
- LKBNLSFEFYTSCW-ZBLYBZFDSA-N (2s,3r)-3-[(2-methylpropan-2-yl)oxy]-2-[[4-phenyl-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]butanoic acid Chemical compound CC(C)(C)O[C@H](C)[C@@H](C(O)=O)NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1NC(=O)NC1=C(C)C=C(C)C=C1C LKBNLSFEFYTSCW-ZBLYBZFDSA-N 0.000 claims 1
- VFXCDESXOOWVLU-BCHFMIIMSA-N (2s,3r)-3-cyclobutyloxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]butanoic acid Chemical compound O([C@H](C)[C@H](NC(=O)C=1C(=CC2=CC=CC=C2C=1)NC(=O)NC=1C(=CC(C)=CC=1C)C)C(O)=O)C1CCC1 VFXCDESXOOWVLU-BCHFMIIMSA-N 0.000 claims 1
- 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 1
- BEYABHAZRRWMOS-DGPALRBDSA-N (2s,3r)-3-phenylmethoxy-2-[[3-[(2,4,6-trimethylphenyl)carbamoylamino]naphthalene-2-carbonyl]amino]pentanoic acid Chemical compound O([C@H](CC)[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 BEYABHAZRRWMOS-DGPALRBDSA-N 0.000 claims 1
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- NVAFMKGSIOBCFA-UHFFFAOYSA-N 1-[[4-(4-methoxyphenyl)-2-[(2,4,6-trimethylphenyl)carbamoylamino]benzoyl]amino]cycloheptane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1NC(=O)NC=2C(=CC(C)=CC=2C)C)=CC=C1C(=O)NC1(C(O)=O)CCCCCC1 NVAFMKGSIOBCFA-UHFFFAOYSA-N 0.000 claims 1
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- HXEXKLWLHOSVIT-UHFFFAOYSA-N 1-[[5-(3,4-difluorophenyl)-3-[(2,4,6-trimethylphenyl)carbamoylamino]thiophene-2-carbonyl]amino]cyclohexane-1-carboxylic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=C(C(=O)NC2(CCCCC2)C(O)=O)SC(C=2C=C(F)C(F)=CC=2)=C1 HXEXKLWLHOSVIT-UHFFFAOYSA-N 0.000 claims 1
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- HNFVEDJDVKGSAV-UHFFFAOYSA-N 1-[[5-(4-methoxyphenyl)-3-[(2,4,6-trimethylphenyl)carbamoylamino]thiophene-2-carbonyl]amino]cyclooctane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)NC=2C(=CC(C)=CC=2C)C)=C(C(=O)NC2(CCCCCCC2)C(O)=O)S1 HNFVEDJDVKGSAV-UHFFFAOYSA-N 0.000 claims 1
- XAFDPVZFEUGUAT-UHFFFAOYSA-N 1-[[5-(4-methoxyphenyl)-3-[(2,4,6-trimethylphenyl)carbamoylamino]thiophene-2-carbonyl]amino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)NC=2C(=CC(C)=CC=2C)C)=C(C(=O)NC2(CCCC2)C(O)=O)S1 XAFDPVZFEUGUAT-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
- PXLOSBDARKDVEX-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-8-yl)-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)C1CCC2(OCCO2)CC1 PXLOSBDARKDVEX-UHFFFAOYSA-N 0.000 claims 1
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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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
-
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
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