JP2002541139A5 - - Google Patents
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- JP2002541139A5 JP2002541139A5 JP2000609388A JP2000609388A JP2002541139A5 JP 2002541139 A5 JP2002541139 A5 JP 2002541139A5 JP 2000609388 A JP2000609388 A JP 2000609388A JP 2000609388 A JP2000609388 A JP 2000609388A JP 2002541139 A5 JP2002541139 A5 JP 2002541139A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- phenoxyisobutyric
- compound
- carbon atoms
- phenoxyisobutyric 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 40
- 125000004432 carbon atom Chemical group C* 0.000 description 35
- 238000000034 method Methods 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 10
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 9
- -1 4-chlorobenzamidophenoxyisobutyryl Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- HYNQTSZBTIOFKH-UHFFFAOYSA-N 2-Amino-5-hydroxybenzoic acid Chemical compound NC1=CC=C(O)C=C1C(O)=O HYNQTSZBTIOFKH-UHFFFAOYSA-N 0.000 description 6
- HJVAVGOPTDJYOJ-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzoic acid Chemical compound COC1=CC(N)=C(C(O)=O)C=C1OC HJVAVGOPTDJYOJ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- VXHGLXRUDKQAEK-UHFFFAOYSA-N 2-[4-[(3,4-dimethoxyphenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC=C(OC(C)(C)C(O)=O)C=C1 VXHGLXRUDKQAEK-UHFFFAOYSA-N 0.000 description 4
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- LDRYOEIGQCIMEK-UHFFFAOYSA-N 2-(2,5-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC(Cl)=CC=C1Cl LDRYOEIGQCIMEK-UHFFFAOYSA-N 0.000 description 3
- LYJCGBYEVXKOST-UHFFFAOYSA-N 2-(4-acetamidophenoxy)acetic acid Chemical compound CC(=O)NC1=CC=C(OCC(O)=O)C=C1 LYJCGBYEVXKOST-UHFFFAOYSA-N 0.000 description 3
- JTARICLTMYASES-UHFFFAOYSA-N 2-(4-aminophenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(N)C=C1 JTARICLTMYASES-UHFFFAOYSA-N 0.000 description 3
- GEQWCUVIQMRCAZ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(O)C=C1 GEQWCUVIQMRCAZ-UHFFFAOYSA-N 0.000 description 3
- JPEIOHFXYPONEI-UHFFFAOYSA-N 2-[(2-carboxyphenyl)iminomethylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC=NC1=CC=CC=C1C(O)=O JPEIOHFXYPONEI-UHFFFAOYSA-N 0.000 description 3
- OUPPDRXKAQXQRE-UHFFFAOYSA-N 2-acetamido-5-acetyloxybenzoic acid Chemical compound CC(=O)NC1=CC=C(OC(C)=O)C=C1C(O)=O OUPPDRXKAQXQRE-UHFFFAOYSA-N 0.000 description 3
- XWHGTQGLZJRYNB-UHFFFAOYSA-N 2-acetamidoterephthalic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC=C1C(O)=O XWHGTQGLZJRYNB-UHFFFAOYSA-N 0.000 description 3
- CNWHHQWYXIPHGY-UHFFFAOYSA-N 2-acetyloxy-5-chlorobenzoic acid Chemical compound CC(=O)OC1=CC=C(Cl)C=C1C(O)=O CNWHHQWYXIPHGY-UHFFFAOYSA-N 0.000 description 3
- GWHXAZLLZVWMNI-UHFFFAOYSA-N 2-acetyloxy-5-hydroxybenzoic acid Chemical compound CC(=O)OC1=CC=C(O)C=C1C(O)=O GWHXAZLLZVWMNI-UHFFFAOYSA-N 0.000 description 3
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 3
- BQGFRFCKVQNHEC-UHFFFAOYSA-N 2-methylquinoline-3,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C)=NC2=C1 BQGFRFCKVQNHEC-UHFFFAOYSA-N 0.000 description 3
- UIDHNPTVQFNWOJ-UHFFFAOYSA-N 2-methylquinoline-4-carboxylic acid Chemical compound C1=CC=CC2=NC(C)=CC(C(O)=O)=C21 UIDHNPTVQFNWOJ-UHFFFAOYSA-N 0.000 description 3
- KJQWSJOVJCOZBD-UHFFFAOYSA-N 2-quinolin-8-yloxypropanoic acid Chemical compound C1=CN=C2C(OC(C)C(O)=O)=CC=CC2=C1 KJQWSJOVJCOZBD-UHFFFAOYSA-N 0.000 description 3
- LTMSNTFHWIQHMQ-UHFFFAOYSA-N 3-[(3-chloro-4-nitrophenyl)carbamoylamino]-2-methyl-2-phenoxypropanoic acid Chemical compound ClC=1C=C(C=CC=1[N+](=O)[O-])NC(NCC(C(=O)O)(C)OC1=CC=CC=C1)=O LTMSNTFHWIQHMQ-UHFFFAOYSA-N 0.000 description 3
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 3
- QBKPZNKYNSTQBG-UHFFFAOYSA-N 4-[(4-carboxy-2-chlorophenyl)iminomethylamino]-3-chlorobenzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1NC=NC1=CC=C(C(O)=O)C=C1Cl QBKPZNKYNSTQBG-UHFFFAOYSA-N 0.000 description 3
- TZXJLFBEXYSTJG-UHFFFAOYSA-N 4-acetamido-2-chlorobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C(Cl)=C1 TZXJLFBEXYSTJG-UHFFFAOYSA-N 0.000 description 3
- HTYBTJJSQMJKSN-UHFFFAOYSA-N 6-bromo-2-methylquinoline-3,4-dicarboxylic acid Chemical compound C1=C(Br)C=C2C(C(O)=O)=C(C(O)=O)C(C)=NC2=C1 HTYBTJJSQMJKSN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QEVZJOOFVAMXKO-AWEZNQCLSA-N (2s)-2-[(4-chlorobenzoyl)amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 QEVZJOOFVAMXKO-AWEZNQCLSA-N 0.000 description 2
- XPDYCERBAXPFRF-UHFFFAOYSA-N 2-[2-(carbamoylamino)phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1NC(N)=O XPDYCERBAXPFRF-UHFFFAOYSA-N 0.000 description 2
- PUTPVINKPFRXHI-UHFFFAOYSA-N 2-[4-(benzylsulfonylamino)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 PUTPVINKPFRXHI-UHFFFAOYSA-N 0.000 description 2
- LCXIRCSISOUPFN-UHFFFAOYSA-N 2-[4-(cyclohexylcarbamoylamino)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1CCCCC1 LCXIRCSISOUPFN-UHFFFAOYSA-N 0.000 description 2
- YTMJKMWJTGDFHX-UHFFFAOYSA-N 2-[4-(phenylcarbamoylamino)phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC(=O)NC1=CC=CC=C1 YTMJKMWJTGDFHX-UHFFFAOYSA-N 0.000 description 2
- OYJPTSMWFKGZJM-UHFFFAOYSA-N 2-[4-({[(3,5-dichlorophenyl)amino]carbonyl}amino)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 OYJPTSMWFKGZJM-UHFFFAOYSA-N 0.000 description 2
- HTKLQJLDMYYLLW-UHFFFAOYSA-N 2-[4-[(2,3-dichlorophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl HTKLQJLDMYYLLW-UHFFFAOYSA-N 0.000 description 2
- LGTIGCKCLFWDLC-UHFFFAOYSA-N 2-[4-[(2-chloro-4-nitrophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl LGTIGCKCLFWDLC-UHFFFAOYSA-N 0.000 description 2
- XIOPROXUSNJVKX-UHFFFAOYSA-N 2-[4-[(2-chloro-5-nitrophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC([N+]([O-])=O)=CC=C1Cl XIOPROXUSNJVKX-UHFFFAOYSA-N 0.000 description 2
- KBLJQBLVEDGLEM-UHFFFAOYSA-N 2-[4-[(3,4-dichlorophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 KBLJQBLVEDGLEM-UHFFFAOYSA-N 0.000 description 2
- XMUWUUJCQZMPKV-UHFFFAOYSA-N 2-[4-[(3,5-difluorophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC(F)=CC(F)=C1 XMUWUUJCQZMPKV-UHFFFAOYSA-N 0.000 description 2
- CUGWZRPGXORGST-UHFFFAOYSA-N 2-[4-[(3-chloro-4-fluorophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 CUGWZRPGXORGST-UHFFFAOYSA-N 0.000 description 2
- FAFDOCGWBXOXEM-UHFFFAOYSA-N 2-[4-[(3-chlorophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 FAFDOCGWBXOXEM-UHFFFAOYSA-N 0.000 description 2
- QVJVMOOBARCPNP-UHFFFAOYSA-N 2-[4-[(4-chloro-3-nitrophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(Cl)C([N+]([O-])=O)=C1 QVJVMOOBARCPNP-UHFFFAOYSA-N 0.000 description 2
- VMSPYYDQVSGVTI-UHFFFAOYSA-N 2-[4-[(4-iodophenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(I)C=C1 VMSPYYDQVSGVTI-UHFFFAOYSA-N 0.000 description 2
- WZEKUXIXSRNHEL-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(OC(C)(C)C(O)=O)C=C1 WZEKUXIXSRNHEL-UHFFFAOYSA-N 0.000 description 2
- JWESYXWOLAVEQI-UHFFFAOYSA-N 2-[4-[2-[(3,5-dichlorobenzoyl)amino]ethyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC(Cl)=CC(Cl)=C1 JWESYXWOLAVEQI-UHFFFAOYSA-N 0.000 description 2
- KMZLKBIRGRUPCR-UHFFFAOYSA-N 2-[4-[[(2-chlorophenyl)-[(3,4-dichlorophenyl)methyl]carbamoyl]amino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)N(C=1C(=CC=CC=1)Cl)CC1=CC=C(Cl)C(Cl)=C1 KMZLKBIRGRUPCR-UHFFFAOYSA-N 0.000 description 2
- PIXYYXYWQPLJAN-UHFFFAOYSA-N 2-[4-[[2-(2,4-dichlorophenyl)-2-oxoethyl]amino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NCC(=O)C1=CC=C(Cl)C=C1Cl PIXYYXYWQPLJAN-UHFFFAOYSA-N 0.000 description 2
- JVMMFUWNIJQCRA-UHFFFAOYSA-N 2-[4-[[2-(3,4-dichlorophenyl)acetyl]amino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)CC1=CC=C(Cl)C(Cl)=C1 JVMMFUWNIJQCRA-UHFFFAOYSA-N 0.000 description 2
- BHPUABPRUDWQJV-UHFFFAOYSA-N 2-[4-[[2-(4-chlorophenoxy)acetyl]amino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1 BHPUABPRUDWQJV-UHFFFAOYSA-N 0.000 description 2
- YBHPNGIDEUUFHE-UHFFFAOYSA-N 2-[4-[[4-(dimethylamino)phenyl]carbamoylamino]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NC1=CC=C(OC(C)(C)C(O)=O)C=C1 YBHPNGIDEUUFHE-UHFFFAOYSA-N 0.000 description 2
- KUVBUGMRSPUHHK-UHFFFAOYSA-N 2-methyl-2-(5-methyl-2-propan-2-ylphenoxy)propanoic acid Chemical compound CC(C)C1=CC=C(C)C=C1OC(C)(C)C(O)=O KUVBUGMRSPUHHK-UHFFFAOYSA-N 0.000 description 2
- OAJSOBONUUZHJH-UHFFFAOYSA-N 2-methyl-2-[4-(phenylcarbamoylamino)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=CC=C1 OAJSOBONUUZHJH-UHFFFAOYSA-N 0.000 description 2
- MKJVKAXNXSUKTP-UHFFFAOYSA-N 2-methyl-2-[4-(pyridin-3-ylcarbamoylamino)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=CN=C1 MKJVKAXNXSUKTP-UHFFFAOYSA-N 0.000 description 2
- QSKUODCURHWVAD-UHFFFAOYSA-N 2-methyl-2-[4-(pyridin-4-ylcarbamoylamino)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=NC=C1 QSKUODCURHWVAD-UHFFFAOYSA-N 0.000 description 2
- BJINMEROLLOVGH-UHFFFAOYSA-N 2-methyl-2-[4-[(2,4,6-trichlorophenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl BJINMEROLLOVGH-UHFFFAOYSA-N 0.000 description 2
- DGBYWLCXRVZKNY-UHFFFAOYSA-N 2-methyl-2-[4-[(2,4,6-trimethylphenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound CC1=CC(C)=CC(C)=C1NC(=O)NC1=CC=C(OC(C)(C)C(O)=O)C=C1 DGBYWLCXRVZKNY-UHFFFAOYSA-N 0.000 description 2
- RETXRBKBFDJBQS-UHFFFAOYSA-N 2-methyl-2-[4-[(3,4,5-trichlorophenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC(Cl)=C(Cl)C(Cl)=C1 RETXRBKBFDJBQS-UHFFFAOYSA-N 0.000 description 2
- XJZGJZWKWJEXMD-UHFFFAOYSA-N 2-methyl-2-[4-[(3,4,5-trimethoxyphenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)NC=2C=CC(OC(C)(C)C(O)=O)=CC=2)=C1 XJZGJZWKWJEXMD-UHFFFAOYSA-N 0.000 description 2
- ZCVGQNIPTZZNQX-UHFFFAOYSA-N 2-methyl-2-[4-[(4-methylphenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(OC(C)(C)C(O)=O)C=C1 ZCVGQNIPTZZNQX-UHFFFAOYSA-N 0.000 description 2
- UQLRIJZZPPDKMV-UHFFFAOYSA-N 2-methyl-2-[4-[(4-morpholin-4-ylsulfonylphenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(S(=O)(=O)N2CCOCC2)C=C1 UQLRIJZZPPDKMV-UHFFFAOYSA-N 0.000 description 2
- KXFLCVDKEJVSAB-UHFFFAOYSA-N 2-methyl-2-[4-[(4-nitrophenyl)carbamoylamino]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 KXFLCVDKEJVSAB-UHFFFAOYSA-N 0.000 description 2
- ARAZWXGQPYMGHA-UHFFFAOYSA-N 4-(2-carboxypropan-2-yloxy)benzoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(C(O)=O)C=C1 ARAZWXGQPYMGHA-UHFFFAOYSA-N 0.000 description 2
- OHQJGYXODUWXTD-UHFFFAOYSA-N 4-[[4-(2-carboxypropan-2-yloxy)phenyl]carbamoylamino]benzoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NC1=CC=C(C(O)=O)C=C1 OHQJGYXODUWXTD-UHFFFAOYSA-N 0.000 description 2
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- IGWJEWGQUFOVDP-UHFFFAOYSA-N 6-chloro-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=CC(Cl)=CC=C21 IGWJEWGQUFOVDP-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000037157 Azotemia Diseases 0.000 description 2
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 2
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 2
- HSMNQINEKMPTIC-UHFFFAOYSA-N N-(4-aminobenzoyl)glycine Chemical compound NC1=CC=C(C(=O)NCC(O)=O)C=C1 HSMNQINEKMPTIC-UHFFFAOYSA-N 0.000 description 2
- 206010029350 Neurotoxicity Diseases 0.000 description 2
- 206010044221 Toxic encephalopathy Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 2
- 229960003067 cystine Drugs 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 230000036252 glycation Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 2
- 230000007135 neurotoxicity Effects 0.000 description 2
- 231100000228 neurotoxicity Toxicity 0.000 description 2
- UCAGLBKTLXCODC-UHFFFAOYSA-N p-Aminosulfonyl-benzoic Acid Natural products NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 208000009852 uremia Diseases 0.000 description 2
- ZWRYXFHYNUGZBT-UHFFFAOYSA-N 2-[4-(benzylcarbamoylamino)phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1NC(=O)NCC1=CC=CC=C1 ZWRYXFHYNUGZBT-UHFFFAOYSA-N 0.000 description 1
- VDODZNGFOUDNJK-UHFFFAOYSA-N 2-[4-[[(3,5-dichlorobenzoyl)amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CNC(=O)C1=CC(Cl)=CC(Cl)=C1 VDODZNGFOUDNJK-UHFFFAOYSA-N 0.000 description 1
- 0 C**(*)(*)OC(C=C1)=C*(C)C=C1NC(NC1=CI(C)=CC(C)(*)C=*1C)=O Chemical compound C**(*)(*)OC(C=C1)=C*(C)C=C1NC(NC1=CI(C)=CC(C)(*)C=*1C)=O 0.000 description 1
- RYGYOKMYKLLJQB-UHFFFAOYSA-N CC(CNC(NCC1=CC=CC=C1)=O)(C(O)=O)OC1=CC=CC=C1 Chemical compound CC(CNC(NCC1=CC=CC=C1)=O)(C(O)=O)OC1=CC=CC=C1 RYGYOKMYKLLJQB-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| PCT/US2000/008938 WO2000059875A2 (en) | 1999-04-05 | 2000-04-05 | Novel inhibitors of formation of advanced glycation endproducts (age's) |
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| CA (1) | CA2368688C (enExample) |
| DE (1) | DE60008509T2 (enExample) |
| WO (1) | WO2000059875A2 (enExample) |
Families Citing this family (46)
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| US7030133B2 (en) * | 1999-04-05 | 2006-04-18 | City Of Hope | Inhibitors of formation of advanced glycation endproducts (AGEs) |
| US6589944B1 (en) * | 1999-04-05 | 2003-07-08 | City Of Hope | Breakers of advanced glycation endproducts |
| US6605642B2 (en) | 1999-04-05 | 2003-08-12 | City Of Hope | Inhibitors of formation of advanced glycation endproducts (AGES) |
| US6787566B2 (en) | 1999-04-05 | 2004-09-07 | City Of Hope | Breakers of advanced glycation endproducts |
| US20030199574A1 (en) | 2000-03-02 | 2003-10-23 | Vitreo-Retinal Technologies, Inc. | Treatment of ophthalmic disorders using urea and urea derivatives |
| DE10158076B4 (de) * | 2001-11-27 | 2005-09-01 | Beiersdorf Ag | Kosmetische und/oder dermatologische Zubereitungen mit einem Gehalt an Aryl-Ureido-Verbindungen und ihre Verwendung |
| EP1480678B1 (en) * | 2002-02-13 | 2009-04-15 | Vitreo-Retinal Technologies, Inc. | Treatment of ophthalmic disorders using urea and urea derivatives |
| US20040057949A1 (en) * | 2002-09-23 | 2004-03-25 | Depaolis Potito U. | Hemodialysis method for improving immune system function |
| WO2004058289A1 (en) * | 2002-12-20 | 2004-07-15 | Chakshu Research, Inc. | Ophthalmic formulation for the prevention and treatment of ocular conditions |
| US20060177430A1 (en) * | 2002-12-20 | 2006-08-10 | Chakshu Research Inc | Treatment of ocular disorders with ophthalmic formulations containing methylsulfonylmethane as a transport enhancer |
| US20060166879A1 (en) * | 2002-12-20 | 2006-07-27 | Chakshu Research Inc | Treatment of conditions associated with the presence of macromolecular aggregates, particularly ophthalmic disorders |
| US20060172972A1 (en) * | 2002-12-20 | 2006-08-03 | Chakshu Research Inc | Formulation and method for administration of ophthalmologically active agents |
| DE60329831D1 (de) * | 2003-06-10 | 2009-12-10 | Biondi Ricardo Miguel | Verwendung einer Verbingung gemäss Formel I zur Herstellung einer pharmazeutischen Zubereitung |
| EP1682114A2 (en) * | 2003-10-27 | 2006-07-26 | City of Hope | Methods of lowering lipid levels in a mammal |
| US9737511B2 (en) * | 2004-05-24 | 2017-08-22 | Geoffrey C. GURTNER | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| WO2005115379A2 (en) * | 2004-05-24 | 2005-12-08 | New York University | Method of treating or preventing pathologic effects of acute increases in hyperglycemia and/or acute increases of free fatty acid flux |
| FR2883873B1 (fr) * | 2005-03-31 | 2009-07-10 | Pharmamens Sarl | Inhibiteurs d'age |
| CA2615231A1 (en) * | 2005-07-15 | 2007-01-25 | Chakshu Research Inc. | Prevention and treatment of ophthalmic complications of diabetes |
| US8053449B2 (en) * | 2005-10-05 | 2011-11-08 | Cell Viable Corporation | Method for inhibiting AGE complex formation |
| US8048896B2 (en) * | 2005-10-05 | 2011-11-01 | Cell Viable Corporation | Methods for inhibiting and breaking AGE complex formation |
| US8580854B2 (en) * | 2005-11-09 | 2013-11-12 | City Of Hope | Methods of suppression of rage gene expression and rage triggered inflammatory genes by selected age-inhibitors |
| DE102007041232A1 (de) | 2007-08-30 | 2009-03-05 | Henkel Ag & Co. Kgaa | Verwendung von Sulfonylharnstoffen zur Spaltung von AGEs |
| US20090023731A1 (en) * | 2007-03-22 | 2009-01-22 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
| US8124655B2 (en) * | 2007-06-15 | 2012-02-28 | City Of Hope | Use of LR-90 and LR-102 to overcome insulin resistance |
| FR2918570B1 (fr) * | 2007-07-09 | 2012-10-05 | Engelhard Lyon | DIGLYCATION DES AGEs. |
| DE102007054653A1 (de) | 2007-11-14 | 2009-05-20 | Henkel Ag & Co. Kgaa | Verwendung von Thioharnstoff-Derivaten zur Spaltung von AGEs |
| US10098857B2 (en) | 2008-10-10 | 2018-10-16 | The Board Of Trustees Of The Leland Stanford Junior University | Topical and transdermal delivery of HIF-1 modulators to prevent and treat chronic wounds |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| HRP20230248T1 (hr) | 2009-06-12 | 2023-04-14 | Abivax | Spojevi korisni za liječenje preranog starenja, te naročito progerije |
| EP2261214A1 (en) * | 2009-06-12 | 2010-12-15 | Splicos Sas | Compounds useful to treat premature aging and in particular progeria |
| EP2465502A1 (en) | 2010-12-15 | 2012-06-20 | Société Splicos | Compounds useful for treating AIDS |
| US9808434B2 (en) | 2011-01-27 | 2017-11-07 | City Of Hope | Compound for treating cancer and diabetes |
| WO2012103523A2 (en) | 2011-01-27 | 2012-08-02 | Samuel Rahbar | Novel modulators of development of adipocyte and cancer cells |
| CN102718727B (zh) * | 2011-03-31 | 2016-04-20 | 中国医学科学院药物研究所 | Gk和ppar双重激动活性的芳基脲类衍生物 |
| CN102718703B (zh) * | 2011-03-31 | 2016-09-14 | 中国医学科学院药物研究所 | Gk和ppar双重激动活性的含有二甲基的芳基脲类衍生物 |
| US20140371316A1 (en) * | 2011-11-23 | 2014-12-18 | Jill S. Fabricant | Derivatives of phenoxyisobutyric acid |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| HRP20211839T1 (hr) | 2013-07-05 | 2022-03-04 | Abivax | Biciklički spojevi korisni za liječenje bolesti uzrokovanih retrovirusima |
| US9827236B2 (en) * | 2014-05-11 | 2017-11-28 | Mythri Ambatipudi | Method of inhibiting the glycation of nutrient and endogenous proteins and peroxidation of nutrient and endogenous lipids |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| CN104961645A (zh) * | 2015-07-22 | 2015-10-07 | 中国药科大学 | 苯氧乙酸类衍生物、其制备方法及其作为药物的用途 |
| US11331288B2 (en) | 2017-09-14 | 2022-05-17 | The Board Of Trustees Of The Leland Stanford Junior University | Conditioning irradiated tissue for increasing vascularity |
| JP2019214546A (ja) * | 2018-06-11 | 2019-12-19 | 学校法人福岡大学 | 終末糖化産物生成抑制剤及び医薬組成物 |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
| EP4069252B1 (en) * | 2019-12-02 | 2025-12-10 | Academia Sinica | Pdia4 inhibitors and use thereof for inhibiting ss-cell pathogenesis and treating diabetes |
| WO2021123419A1 (en) * | 2019-12-20 | 2021-06-24 | Basf Se | Composition for the treatment of amyloid-beta associated diseases |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5272176A (en) * | 1984-03-19 | 1993-12-21 | The Rockefeller University | Advanced glycation inhibitors containing amino-benzoic acids and derivatives, and methods of use |
| DE3410927A1 (de) | 1984-03-24 | 1985-10-03 | Hoechst Ag, 6230 Frankfurt | Vollaromatische polyester, verfahren zu ihrer herstellung und entsprechende formkoerper |
| JPS619227A (ja) * | 1984-06-22 | 1986-01-16 | 生体機能利用化学品新製造技術研究組合 | キンポウゲ科植物の組織培養方法 |
| JPS6222517A (ja) * | 1985-07-23 | 1987-01-30 | 株式会社ツムラ | ウリ科植物不定根の培養方法 |
| JPS6232880A (ja) * | 1985-08-06 | 1987-02-12 | Seitai Kinou Riyou Kagakuhin Shinseizou Gijutsu Kenkyu Kumiai | キンポウゲ科植物の組織培養方法 |
| US5268500A (en) | 1987-06-15 | 1993-12-07 | Montefiore Medical Center | Compound, composition and method for the reduction of lipids the modification of the affinity of hemoblogin for oxygen and the prevention of platelet aggregation |
| US5093367A (en) | 1988-06-15 | 1992-03-03 | Montefiore Medical Center | Method of synthesis and novel compounds for pharmaceutical uses |
| US4921997A (en) | 1988-06-15 | 1990-05-01 | Montefiore Medical Center | Method of synthesis and novel compounds for pharmaceutical uses |
| US5677330A (en) * | 1990-02-12 | 1997-10-14 | The Center For Innovative Technology | Medical uses of allosteric hemoglobin modifier compounds in patient care |
| WO1995031192A1 (en) * | 1994-05-16 | 1995-11-23 | Thomas Jefferson University | Method and use of agents to inhibit protein polymerization and methods of identifying these agents |
| US5962651A (en) * | 1995-01-27 | 1999-10-05 | Montefiore Medical Center | Modified hemoglobin and its use as a component of an artificial blood substitute |
| US5602277A (en) | 1995-03-30 | 1997-02-11 | Biocryst Pharmaceuticals, Inc. | Substituted benzene derivatives useful as neuraminidase inhibitors |
| US5716987A (en) | 1996-06-21 | 1998-02-10 | Bristol-Myers Squibb Company | Prophylactic and therapeutic treatment of skin sensitization and irritation |
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2000
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- 2000-04-05 AT AT00920121T patent/ATE260099T1/de not_active IP Right Cessation
- 2000-04-05 US US09/543,703 patent/US6337350B1/en not_active Expired - Lifetime
- 2000-04-05 JP JP2000609388A patent/JP5209832B2/ja not_active Expired - Lifetime
- 2000-04-05 WO PCT/US2000/008938 patent/WO2000059875A2/en not_active Ceased
- 2000-04-05 AU AU40707/00A patent/AU763750B2/en not_active Expired
- 2000-04-05 EP EP00920121A patent/EP1165064B1/en not_active Expired - Lifetime
- 2000-04-05 DE DE60008509T patent/DE60008509T2/de not_active Expired - Lifetime
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