ES2375132T3 - Dicarboxamidas de arilo. - Google Patents
Dicarboxamidas de arilo. Download PDFInfo
- Publication number
- ES2375132T3 ES2375132T3 ES04742005T ES04742005T ES2375132T3 ES 2375132 T3 ES2375132 T3 ES 2375132T3 ES 04742005 T ES04742005 T ES 04742005T ES 04742005 T ES04742005 T ES 04742005T ES 2375132 T3 ES2375132 T3 ES 2375132T3
- Authority
- ES
- Spain
- Prior art keywords
- amino
- substituted
- unsubstituted
- methyl
- carbonyl
- 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.)
- Expired - Lifetime
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 28
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 28
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 20
- 239000008103 glucose Substances 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 16
- 208000008589 Obesity Diseases 0.000 claims abstract description 14
- 235000020824 obesity Nutrition 0.000 claims abstract description 14
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 7
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 6
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 5
- 125000005418 aryl aryl group Chemical group 0.000 claims abstract description 4
- -1 cyano, hydroxy, mercapto Chemical class 0.000 claims description 184
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 83
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 72
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- WUTVNBPTVYUJJL-UHFFFAOYSA-N 5-[3-cyclopentylpropanoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)CCC2CCCC2)=C1 WUTVNBPTVYUJJL-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000006733 (C6-C15) alkyl group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- APFLCNKRXAFAEF-UHFFFAOYSA-N 2-hydroxy-4-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C=1C=C(O)C(C(O)=O)=CC=1)C(=O)C1=CC=C(C(F)(F)F)C=C1 APFLCNKRXAFAEF-UHFFFAOYSA-N 0.000 claims description 3
- MLLJUCAPOORHDS-UHFFFAOYSA-N 2-hydroxy-5-[(2-phenoxyacetyl)-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)COC=2C=CC=CC=2)=C1 MLLJUCAPOORHDS-UHFFFAOYSA-N 0.000 claims description 3
- SOVZDLBJJPAIHR-UHFFFAOYSA-N 2-hydroxy-5-[3-methylbut-2-enoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]benzoic acid Chemical compound C=1C=C(O)C(C(O)=O)=CC=1N(C(=O)C=C(C)C)CC(C=C1)=CC=C1C(=O)NCC(C=C1)=CC=C1OC1=CC=CC=C1 SOVZDLBJJPAIHR-UHFFFAOYSA-N 0.000 claims description 3
- XDZRTNYGBPNNII-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-(3-phenylpropanoyl)amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C=1C=C(C(O)=CC=1)C(O)=O)C(=O)CCC1=CC=CC=C1 XDZRTNYGBPNNII-UHFFFAOYSA-N 0.000 claims description 3
- RPUZJMCKNCDCCL-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2SC=C(N=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 RPUZJMCKNCDCCL-UHFFFAOYSA-N 0.000 claims description 3
- WWVMZQLVQAQTTO-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 WWVMZQLVQAQTTO-UHFFFAOYSA-N 0.000 claims description 3
- WFCDPJZDVJLUAU-UHFFFAOYSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-(2-phenoxyacetyl)amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 WFCDPJZDVJLUAU-UHFFFAOYSA-N 0.000 claims description 3
- OKPWVHBHJMKTOA-CAPFRKAQSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)\C=C\C=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 OKPWVHBHJMKTOA-CAPFRKAQSA-N 0.000 claims description 3
- ONJDTUVILNQEGM-UHFFFAOYSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(O)C(C(O)=O)=C1 ONJDTUVILNQEGM-UHFFFAOYSA-N 0.000 claims description 3
- KUWSGDRFKSTVEE-UHFFFAOYSA-N 2-hydroxy-5-[[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(O)C(C(O)=O)=C1 KUWSGDRFKSTVEE-UHFFFAOYSA-N 0.000 claims description 3
- WBHZNAQHMWPELK-UHFFFAOYSA-N 4-[3-cyclopentylpropanoyl-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C=1C=C(O)C(C(O)=O)=CC=1)C(=O)CCC1CCCC1 WBHZNAQHMWPELK-UHFFFAOYSA-N 0.000 claims description 3
- GUJCLAIIBPUHNV-UHFFFAOYSA-N 5-[[3-cyclopentylpropanoyl-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl]amino]methyl]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)CCC1CCCC1)CC1=CC=C(O)C(C(O)=O)=C1 GUJCLAIIBPUHNV-UHFFFAOYSA-N 0.000 claims description 3
- SJBHRGLXGLBOBY-UHFFFAOYSA-N 5-[benzoyl-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2N=C(SC=2)C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC=CC=2)=C1 SJBHRGLXGLBOBY-UHFFFAOYSA-N 0.000 claims description 3
- OQIRIDMPHWDPFH-UHFFFAOYSA-N 5-[cyclohexanecarbonyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C2CCCCC2)=C1 OQIRIDMPHWDPFH-UHFFFAOYSA-N 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- NPFIUHQJRZGQPG-UHFFFAOYSA-N 2-[4-[[(2-phenoxyacetyl)-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 NPFIUHQJRZGQPG-UHFFFAOYSA-N 0.000 claims description 2
- VPNTWIBYNXNTNZ-UHFFFAOYSA-N 2-[4-[[[2-[4-(octylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1C1=NC(CN(CC=2C=CC(OCC(O)=O)=CC=2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=CS1 VPNTWIBYNXNTNZ-UHFFFAOYSA-N 0.000 claims description 2
- YIFJGICTMLQRNV-UHFFFAOYSA-N 2-[4-[[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C1 YIFJGICTMLQRNV-UHFFFAOYSA-N 0.000 claims description 2
- QKWWJYFHQBOYSJ-UHFFFAOYSA-N 2-hydroxy-5-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(2-phenoxyacetyl)amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)COC=3C=CC=CC=3)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 QKWWJYFHQBOYSJ-UHFFFAOYSA-N 0.000 claims description 2
- LNEYSWBYZUJJPR-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl-(3-phenylpropanoyl)amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2SC=C(N=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)CCC=2C=CC=CC=2)=C1 LNEYSWBYZUJJPR-UHFFFAOYSA-N 0.000 claims description 2
- CISLRUUVLWUCHA-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-(3-phenylpropanoyl)amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)CCC=2C=CC=CC=2)=C1 CISLRUUVLWUCHA-UHFFFAOYSA-N 0.000 claims description 2
- UKVJDXJZZBQSJY-UHFFFAOYSA-N 2-hydroxy-5-[[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-(2-phenoxyacetyl)amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 UKVJDXJZZBQSJY-UHFFFAOYSA-N 0.000 claims description 2
- OSFADAFKTPSSCV-UHFFFAOYSA-N 5-[(4-cyanobenzoyl)-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)C=3C=CC(=CC=3)C#N)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 OSFADAFKTPSSCV-UHFFFAOYSA-N 0.000 claims description 2
- CUNBWODFBJIRTC-UHFFFAOYSA-N 5-[(4-cyanobenzoyl)-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC(=CC=2)C#N)=C1 CUNBWODFBJIRTC-UHFFFAOYSA-N 0.000 claims description 2
- VUGVHWIYDOTFHG-UHFFFAOYSA-N 5-[acetyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C=1C=C(O)C(C(O)=O)=CC=1N(C(=O)C)CC(C=C1)=CC=C1C(=O)NCC(C=C1)=CC=C1OC1=CC=CC=C1 VUGVHWIYDOTFHG-UHFFFAOYSA-N 0.000 claims description 2
- ANCVOGMIGBIFOS-UHFFFAOYSA-N 5-[benzoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2SC=C(N=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC=CC=2)=C1 ANCVOGMIGBIFOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000003893 regulation of appetite Effects 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- FTJHKZQHQDKPFJ-UHFFFAOYSA-N (carbamoylamino)carbamic acid Chemical compound NC(=O)NNC(O)=O FTJHKZQHQDKPFJ-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- QJUKKIDACQSTIB-UHFFFAOYSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)CCC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 QJUKKIDACQSTIB-UHFFFAOYSA-N 0.000 claims 1
- CKYRYIQTDPFWJP-XQNSMLJCSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)\C=C\C=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 CKYRYIQTDPFWJP-XQNSMLJCSA-N 0.000 claims 1
- FCAHBLZPXKOXRN-UHFFFAOYSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 FCAHBLZPXKOXRN-UHFFFAOYSA-N 0.000 claims 1
- BXEAQJQDKQWBGN-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(CC=3C=CC(OCC(O)=O)=CC=3)C(=O)CCC=3C=CC=CC=3)N=2)C=C1 BXEAQJQDKQWBGN-UHFFFAOYSA-N 0.000 claims 1
- FLAZSTIQEPUNAY-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(CC=3C=CC(OCC(O)=O)=CC=3)C(=O)C=3C=CC(=CC=3)C(F)(F)F)N=2)C=C1 FLAZSTIQEPUNAY-UHFFFAOYSA-N 0.000 claims 1
- YDTQKULHEUEFEF-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)CCC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 YDTQKULHEUEFEF-UHFFFAOYSA-N 0.000 claims 1
- HXHLJIMPJZGDJR-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 HXHLJIMPJZGDJR-UHFFFAOYSA-N 0.000 claims 1
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229920001469 poly(aryloxy)thionylphosphazene Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 148
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- 230000000291 postprandial effect Effects 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003806 protein tyrosine phosphatase inhibitor Substances 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000029892 regulation of protein phosphorylation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- JBMJCQARHLHKRJ-UHFFFAOYSA-N spiro[9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,10-tetraene-3,3'-pyrrolidine]-2,2',5'-trione Chemical compound O=C1NC(=O)CC21C(C=CC=C1OC=C3)=C1N3C2=O JBMJCQARHLHKRJ-UHFFFAOYSA-N 0.000 description 1
- LQQTXLXDYXLCCG-UHFFFAOYSA-N spiro[chromene-4,5'-imidazolidine]-2',4'-dione Chemical compound N1C(=O)NC(=O)C21C1=CC=CC=C1OC=C2 LQQTXLXDYXLCCG-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyamides (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03102236 | 2003-07-21 | ||
| EP03102236 | 2003-07-21 | ||
| US51782403P | 2003-11-06 | 2003-11-06 | |
| US517824P | 2003-11-06 | ||
| PCT/EP2004/051558 WO2005011685A1 (en) | 2003-07-21 | 2004-07-20 | Aryl dicarboxamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2375132T3 true ES2375132T3 (es) | 2012-02-27 |
Family
ID=34924079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04742005T Expired - Lifetime ES2375132T3 (es) | 2003-07-21 | 2004-07-20 | Dicarboxamidas de arilo. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7365225B2 (https=) |
| EP (1) | EP1656139B1 (https=) |
| JP (1) | JP2006528157A (https=) |
| AT (1) | ATE526964T1 (https=) |
| AU (1) | AU2004260831A1 (https=) |
| CA (1) | CA2529662A1 (https=) |
| DK (1) | DK1656139T3 (https=) |
| ES (1) | ES2375132T3 (https=) |
| PL (1) | PL1656139T3 (https=) |
| PT (1) | PT1656139E (https=) |
| SI (1) | SI1656139T1 (https=) |
| WO (1) | WO2005011685A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1654247B1 (en) * | 2003-07-21 | 2010-01-20 | Merck Serono SA | Alkynyl aryl carboxamides |
| EP1841749A1 (en) | 2004-09-02 | 2007-10-10 | Metabasis Therapeutics, Inc. | Derivatives of thiazole and thiadiazole inhibitors of tyrosine phosphatases |
| JP2008007405A (ja) * | 2004-12-07 | 2008-01-17 | Takeda Chem Ind Ltd | カルボキサミド誘導体 |
| US20090176837A1 (en) * | 2005-07-12 | 2009-07-09 | Sony Corporation | Compounds with activity at retinoic acid receptors |
| ITRM20050390A1 (it) * | 2005-07-22 | 2007-01-23 | Giuliani Spa | Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico. |
| KR20080066938A (ko) * | 2005-10-07 | 2008-07-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 복소환 화합물 및 그것을 함유하는 의약 조성물 |
| TWI580356B (zh) | 2007-08-13 | 2017-05-01 | 孟山都科技有限責任公司 | 控制植物寄生性線蟲的化合物及方法以及被覆有該化合物之種子 |
| DE102007061764A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
| DE202011110963U1 (de) * | 2010-11-05 | 2017-11-07 | Senomyx, Inc. | Verbindungen, die als Modulatoren von TRPM8 nützlich sind |
| MX389514B (es) | 2015-10-01 | 2025-03-20 | Firmenich Incorporated | Compuestos útiles como moduladores de canal receptor 8 de potencial transitorio de melastatina (trpm8). |
| CA3002416C (en) | 2015-10-23 | 2023-10-24 | Vifor (International) Ag | Benzimidazolyl derivatives for use as ferroportin inhibitors |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000069810A1 (en) * | 1999-05-17 | 2000-11-23 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| PL359619A1 (en) * | 2000-06-23 | 2004-08-23 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| US6972340B2 (en) * | 2000-08-29 | 2005-12-06 | Abbott Laboratories | Selective protein tyrosine phosphatatase inhibitors |
| DE10044792A1 (de) * | 2000-09-11 | 2002-04-04 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäureamide und ihre Verwendung |
| JP2004513935A (ja) * | 2000-11-17 | 2004-05-13 | ノボ ノルディスク アクティーゼルスカブ | グルカゴンアンタゴニスト／逆アゴニスト |
| AU2002223501A1 (en) * | 2000-11-17 | 2002-05-27 | Agouron Pharmaceuticals, Inc. | Glucagon antagonists/inverse agonists |
| US6878743B2 (en) * | 2001-09-18 | 2005-04-12 | Sunesis Pharmaceuticals, Inc. | Small molecule inhibitors of caspases |
| CN100410236C (zh) * | 2002-01-29 | 2008-08-13 | 雪兰诺实验室有限公司 | 作为蛋白酪氨酸磷酸酶调节剂的取代亚甲基酰胺衍生物 |
| EP1654247B1 (en) * | 2003-07-21 | 2010-01-20 | Merck Serono SA | Alkynyl aryl carboxamides |
-
2004
- 2004-07-20 SI SI200431770T patent/SI1656139T1/sl unknown
- 2004-07-20 JP JP2006520836A patent/JP2006528157A/ja not_active Withdrawn
- 2004-07-20 AU AU2004260831A patent/AU2004260831A1/en not_active Abandoned
- 2004-07-20 PT PT04742005T patent/PT1656139E/pt unknown
- 2004-07-20 ES ES04742005T patent/ES2375132T3/es not_active Expired - Lifetime
- 2004-07-20 CA CA002529662A patent/CA2529662A1/en not_active Abandoned
- 2004-07-20 AT AT04742005T patent/ATE526964T1/de active
- 2004-07-20 US US10/565,557 patent/US7365225B2/en not_active Expired - Fee Related
- 2004-07-20 DK DK04742005.4T patent/DK1656139T3/da active
- 2004-07-20 PL PL04742005T patent/PL1656139T3/pl unknown
- 2004-07-20 EP EP04742005A patent/EP1656139B1/en not_active Expired - Lifetime
- 2004-07-20 WO PCT/EP2004/051558 patent/WO2005011685A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| SI1656139T1 (sl) | 2011-12-30 |
| DK1656139T3 (da) | 2012-01-30 |
| ATE526964T1 (de) | 2011-10-15 |
| AU2004260831A1 (en) | 2005-02-10 |
| JP2006528157A (ja) | 2006-12-14 |
| EP1656139B1 (en) | 2011-10-05 |
| US20060189583A1 (en) | 2006-08-24 |
| WO2005011685A1 (en) | 2005-02-10 |
| CA2529662A1 (en) | 2005-02-10 |
| EP1656139A1 (en) | 2006-05-17 |
| PL1656139T3 (pl) | 2012-03-30 |
| PT1656139E (pt) | 2011-11-04 |
| US7365225B2 (en) | 2008-04-29 |
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