NO327957B1 - Substituert fenylpropansyrederivater som agonister for human peroksisom proliferantaktivert reseptor (PPAR)<alfa> - Google Patents
Substituert fenylpropansyrederivater som agonister for human peroksisom proliferantaktivert reseptor (PPAR)<alfa> Download PDFInfo
- Publication number
- NO327957B1 NO327957B1 NO20016001A NO20016001A NO327957B1 NO 327957 B1 NO327957 B1 NO 327957B1 NO 20016001 A NO20016001 A NO 20016001A NO 20016001 A NO20016001 A NO 20016001A NO 327957 B1 NO327957 B1 NO 327957B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- carbon atoms
- phenyl
- lower alkyl
- lower alkoxy
- Prior art date
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- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000000556 agonist Substances 0.000 title claims description 5
- 210000002824 peroxisome Anatomy 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 150000004677 hydrates Chemical class 0.000 claims abstract description 40
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 22
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 232
- 150000001875 compounds Chemical class 0.000 claims description 198
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 125000003545 alkoxy group Chemical group 0.000 claims description 110
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 75
- -1 benzylthio group Chemical group 0.000 claims description 74
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 19
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- YSFRXMSOTXOZQZ-UHFFFAOYSA-N 2-[[4-methoxy-3-[[4-(trifluoromethyl)phenyl]methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)=C1 YSFRXMSOTXOZQZ-UHFFFAOYSA-N 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 3
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims 2
- VRHOBXXCNBZJRX-IBGZPJMESA-N (2s)-2-[[3-[[4-(4-fluorophenoxy)phenyl]methylcarbamoyl]-4-methoxyphenyl]methyl]butanoic acid Chemical compound CC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=C1 VRHOBXXCNBZJRX-IBGZPJMESA-N 0.000 claims 1
- VNHMVXOBDJSGEX-FQEVSTJZSA-N (2s)-2-[[3-[[4-(4-fluorophenoxy)phenyl]methylcarbamoyl]-4-methoxyphenyl]methyl]pentanoic acid Chemical compound CCC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=C1 VNHMVXOBDJSGEX-FQEVSTJZSA-N 0.000 claims 1
- VYRQBJZRNPNASW-FQEVSTJZSA-N (2s)-2-[[4-methoxy-3-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 VYRQBJZRNPNASW-FQEVSTJZSA-N 0.000 claims 1
- PJFGOJGZLXDMHN-NRFANRHFSA-N (2s)-2-[[4-methoxy-3-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 PJFGOJGZLXDMHN-NRFANRHFSA-N 0.000 claims 1
- JBSCFQSTJBXELR-FQEVSTJZSA-N (2s)-2-[[4-methoxy-3-[[4-(2-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C(=CC=CC=3)OC)=CC=2)=C1 JBSCFQSTJBXELR-FQEVSTJZSA-N 0.000 claims 1
- RVWJJVSPXYDXAK-NRFANRHFSA-N (2s)-2-[[4-methoxy-3-[[4-(2-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C(=CC=CC=3)OC)=CC=2)=C1 RVWJJVSPXYDXAK-NRFANRHFSA-N 0.000 claims 1
- YOGGBUXVHLTHST-NRFANRHFSA-N (2s)-2-[[4-methoxy-3-[[4-(3-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=C(OC)C=CC=3)=CC=2)=C1 YOGGBUXVHLTHST-NRFANRHFSA-N 0.000 claims 1
- YSFRXMSOTXOZQZ-HNNXBMFYSA-N (2s)-2-[[4-methoxy-3-[[4-(trifluoromethyl)phenyl]methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)=C1 YSFRXMSOTXOZQZ-HNNXBMFYSA-N 0.000 claims 1
- VRHOBXXCNBZJRX-UHFFFAOYSA-N 2-[[3-[[4-(4-fluorophenoxy)phenyl]methylcarbamoyl]-4-methoxyphenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=C1 VRHOBXXCNBZJRX-UHFFFAOYSA-N 0.000 claims 1
- VNHMVXOBDJSGEX-UHFFFAOYSA-N 2-[[3-[[4-(4-fluorophenoxy)phenyl]methylcarbamoyl]-4-methoxyphenyl]methyl]pentanoic acid Chemical compound CCCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=C1 VNHMVXOBDJSGEX-UHFFFAOYSA-N 0.000 claims 1
- PJFGOJGZLXDMHN-UHFFFAOYSA-N 2-[[4-methoxy-3-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 PJFGOJGZLXDMHN-UHFFFAOYSA-N 0.000 claims 1
- JBSCFQSTJBXELR-UHFFFAOYSA-N 2-[[4-methoxy-3-[[4-(2-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C(=CC=CC=3)OC)=CC=2)=C1 JBSCFQSTJBXELR-UHFFFAOYSA-N 0.000 claims 1
- RVWJJVSPXYDXAK-UHFFFAOYSA-N 2-[[4-methoxy-3-[[4-(2-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C(=CC=CC=3)OC)=CC=2)=C1 RVWJJVSPXYDXAK-UHFFFAOYSA-N 0.000 claims 1
- TXQGVEHOJCJYPV-UHFFFAOYSA-N 2-[[4-methoxy-3-[[4-(3-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=C(OC)C=CC=3)=CC=2)=C1 TXQGVEHOJCJYPV-UHFFFAOYSA-N 0.000 claims 1
- YOGGBUXVHLTHST-UHFFFAOYSA-N 2-[[4-methoxy-3-[[4-(3-methoxyphenoxy)phenyl]methylcarbamoyl]phenyl]methyl]pentanoic acid Chemical compound CCCC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=C(OC)C=CC=3)=CC=2)=C1 YOGGBUXVHLTHST-UHFFFAOYSA-N 0.000 claims 1
- MQSZYPGPYYEKHH-UHFFFAOYSA-N 2-methoxy-3-[4-methoxy-3-[[4-(trifluoromethyl)phenyl]methylcarbamoyl]phenyl]propanoic acid Chemical compound COC(C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)=C1 MQSZYPGPYYEKHH-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 230000027455 binding Effects 0.000 abstract description 10
- 239000003446 ligand Substances 0.000 abstract description 6
- 102000005962 receptors Human genes 0.000 abstract description 3
- 108020003175 receptors Proteins 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- 238000006243 chemical reaction Methods 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 31
- 238000003756 stirring Methods 0.000 description 31
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 20
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16223599 | 1999-06-09 | ||
| JP2000157600A JP4618845B2 (ja) | 1999-06-09 | 2000-05-29 | ヒトペルオキシゾーム増殖薬活性化受容体（ＰＰＡＲ）αアゴニストとしての置換フェニルプロピオン酸誘導体 |
| PCT/JP2000/003707 WO2000075103A1 (fr) | 1999-06-09 | 2000-06-08 | DERIVES D'ACIDE PHENYLPROPIONIQUE SUBSTITUES COMME AGONISTES DU RECEPTEUR HUMAIN ACTIVE DE LA PROLIFERATION DES PEROXYSOMES (PPAR) $g(a) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20016001D0 NO20016001D0 (no) | 2001-12-07 |
| NO20016001L NO20016001L (no) | 2002-02-11 |
| NO327957B1 true NO327957B1 (no) | 2009-10-26 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20016001A NO327957B1 (no) | 1999-06-09 | 2001-12-07 | Substituert fenylpropansyrederivater som agonister for human peroksisom proliferantaktivert reseptor (PPAR)<alfa> |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6506797B1 (ja) |
| EP (1) | EP1184366B1 (ja) |
| JP (1) | JP4618845B2 (ja) |
| KR (1) | KR100704142B1 (ja) |
| CN (1) | CN1157368C (ja) |
| AT (1) | ATE288887T1 (ja) |
| AU (1) | AU773445B2 (ja) |
| BR (1) | BR0011734A (ja) |
| CA (1) | CA2376094C (ja) |
| DE (1) | DE60018064T2 (ja) |
| DK (1) | DK1184366T3 (ja) |
| ES (1) | ES2235886T3 (ja) |
| HU (1) | HUP0201654A3 (ja) |
| NO (1) | NO327957B1 (ja) |
| NZ (1) | NZ515705A (ja) |
| PT (1) | PT1184366E (ja) |
| WO (1) | WO2000075103A1 (ja) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0202731A3 (en) * | 1999-09-17 | 2003-10-28 | Kyorin Seiyaku Kk | O-anisamide derivatives, process for their preparation and pharmaceutical compositions containing them |
| TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| US6768008B2 (en) * | 2000-04-24 | 2004-07-27 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| US7049342B2 (en) * | 2000-05-29 | 2006-05-23 | Kyorin Pharmaceutical Co., Ltd. | Substituted phenylpropionic acid derivatives |
| CA2410647C (en) * | 2000-05-29 | 2010-02-09 | Kyorin Pharmaceutical Co., Ltd. | Substituted phenylpropanoic acid derivatives |
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|---|---|---|---|---|
| DK148576A (da) * | 1975-04-18 | 1976-10-19 | Boehringer Mannheim Gmbh | Fenylalkankarbonsyrederivater og fremgangsmade til deres fremstilling |
| GB9600464D0 (en) | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| GB9606805D0 (en) * | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
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- 2000-06-08 NZ NZ515705A patent/NZ515705A/xx not_active IP Right Cessation
- 2000-06-08 CN CNB008086869A patent/CN1157368C/zh not_active Expired - Fee Related
- 2000-06-08 BR BR0011734-0A patent/BR0011734A/pt not_active IP Right Cessation
- 2000-06-08 CA CA002376094A patent/CA2376094C/en not_active Expired - Fee Related
- 2000-06-08 US US10/009,175 patent/US6506797B1/en not_active Expired - Fee Related
- 2000-06-08 KR KR1020017015777A patent/KR100704142B1/ko not_active IP Right Cessation
- 2000-06-08 AU AU51067/00A patent/AU773445B2/en not_active Ceased
- 2000-06-08 HU HU0201654A patent/HUP0201654A3/hu unknown
- 2000-06-08 DK DK00935582T patent/DK1184366T3/da active
- 2000-06-08 ES ES00935582T patent/ES2235886T3/es not_active Expired - Lifetime
- 2000-06-08 DE DE60018064T patent/DE60018064T2/de not_active Expired - Lifetime
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- 2000-06-08 PT PT00935582T patent/PT1184366E/pt unknown
- 2000-06-08 AT AT00935582T patent/ATE288887T1/de active
- 2000-06-08 EP EP00935582A patent/EP1184366B1/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| AU5106700A (en) | 2000-12-28 |
| NO20016001D0 (no) | 2001-12-07 |
| CN1354742A (zh) | 2002-06-19 |
| EP1184366A1 (en) | 2002-03-06 |
| CN1157368C (zh) | 2004-07-14 |
| CA2376094A1 (en) | 2000-12-04 |
| ES2235886T3 (es) | 2005-07-16 |
| KR100704142B1 (ko) | 2007-04-09 |
| PT1184366E (pt) | 2005-06-30 |
| NO20016001L (no) | 2002-02-11 |
| JP2001055367A (ja) | 2001-02-27 |
| BR0011734A (pt) | 2002-03-05 |
| HUP0201654A3 (en) | 2004-03-01 |
| KR20020008221A (ko) | 2002-01-29 |
| HUP0201654A2 (en) | 2002-09-28 |
| DE60018064T2 (de) | 2006-01-12 |
| DK1184366T3 (da) | 2005-05-23 |
| US6506797B1 (en) | 2003-01-14 |
| DE60018064D1 (de) | 2005-03-17 |
| EP1184366B1 (en) | 2005-02-09 |
| ATE288887T1 (de) | 2005-02-15 |
| JP4618845B2 (ja) | 2011-01-26 |
| NZ515705A (en) | 2003-02-28 |
| CA2376094C (en) | 2007-06-05 |
| AU773445B2 (en) | 2004-05-27 |
| EP1184366A4 (en) | 2002-10-31 |
| WO2000075103A1 (fr) | 2000-12-14 |
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