SK283055B6 - Farmaceutický prostriedok obsahujúci 4-oxobutánové kyseliny - Google Patents
Farmaceutický prostriedok obsahujúci 4-oxobutánové kyseliny Download PDFInfo
- Publication number
- SK283055B6 SK283055B6 SK180-99A SK18099A SK283055B6 SK 283055 B6 SK283055 B6 SK 283055B6 SK 18099 A SK18099 A SK 18099A SK 283055 B6 SK283055 B6 SK 283055B6
- Authority
- SK
- Slovakia
- Prior art keywords
- oxobutanoic
- benzyl
- group
- acid
- aryl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- GFXJNGOOVZVTSF-UHFFFAOYSA-N 4-oxobut-2-ynoic acid Chemical class OC(=O)C#CC=O GFXJNGOOVZVTSF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 20
- -1 tetrahydropyrranyl Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002541 furyl group Chemical group 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- TVLYZHRGSUXOQF-UHFFFAOYSA-N 2-benzyl-4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)CC(C(O)=O)CC1=CC=CC=C1 TVLYZHRGSUXOQF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- NYCYMQAQDZTLJC-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)CC(C(O)=O)CC1=CC=C(Cl)C=C1 NYCYMQAQDZTLJC-UHFFFAOYSA-N 0.000 claims description 2
- STDPGSJNESFTQC-UHFFFAOYSA-N 2-benzyl-4-(4-methylphenyl)-4-oxobutanoic acid Chemical compound C1=CC(C)=CC=C1C(=O)CC(C(O)=O)CC1=CC=CC=C1 STDPGSJNESFTQC-UHFFFAOYSA-N 0.000 claims description 2
- DSZFVARAOPNLQT-UHFFFAOYSA-N 4-oxo-2-(oxolan-2-ylmethyl)-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(=O)CC(C(=O)O)CC1CCCO1 DSZFVARAOPNLQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical class OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- MWQJJBARZUVYQD-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-[(4-methoxyphenyl)methyl]-4-oxobutanoic acid Chemical compound FC1=CC=C(C=C1)C(C(=O)O)(CC=O)CC1=CC=C(C=C1)OC MWQJJBARZUVYQD-UHFFFAOYSA-N 0.000 claims 1
- QPORTTBGWVROJY-UHFFFAOYSA-N 2-benzyl-4-oxo-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C1=CC=CC=C1 QPORTTBGWVROJY-UHFFFAOYSA-N 0.000 claims 1
- XBDRBCMSMYDPAS-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-benzyl-4-oxobutanoic acid Chemical compound C=1C=C2OCOC2=CC=1C(=O)CC(C(=O)O)CC1=CC=CC=C1 XBDRBCMSMYDPAS-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 206010012601 diabetes mellitus Diseases 0.000 description 13
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- DZRBTTWGDHUKDS-UHFFFAOYSA-N 2-benzyl-4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CC(=O)C1=CC=C(F)C=C1 DZRBTTWGDHUKDS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- BBKNXOBFZKUGSU-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)-2-oxoethyl]propanedioic acid Chemical compound COc1ccc(cc1)C(=O)CC(C(O)=O)C(O)=O BBKNXOBFZKUGSU-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 102000051325 Glucagon Human genes 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- QIXYGJBDJCMKHU-UHFFFAOYSA-N diethyl 2-benzyl-2-[2-(4-methoxyphenyl)-2-oxoethyl]propanedioate Chemical compound C=1C=CC=CC=1CC(C(=O)OCC)(C(=O)OCC)CC(=O)C1=CC=C(OC)C=C1 QIXYGJBDJCMKHU-UHFFFAOYSA-N 0.000 description 2
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- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal 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)
- Hematology (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9610254A FR2752422B1 (fr) | 1996-08-16 | 1996-08-16 | Composition pharmaceutique contenant des acides 4-oxo-butanoiques |
| PCT/EP1997/004252 WO1998007681A1 (fr) | 1996-08-16 | 1997-08-05 | Compositions pharmaceutiques contenant des acides 4-oxo-butanoiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK18099A3 SK18099A3 (en) | 2000-03-13 |
| SK283055B6 true SK283055B6 (sk) | 2003-02-04 |
Family
ID=9495089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK180-99A SK283055B6 (sk) | 1996-08-16 | 1997-08-05 | Farmaceutický prostriedok obsahujúci 4-oxobutánové kyseliny |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6143787A (cs) |
| EP (1) | EP0925273B1 (cs) |
| JP (1) | JP3105545B2 (cs) |
| KR (1) | KR100488430B1 (cs) |
| CN (1) | CN1082370C (cs) |
| AR (1) | AR009251A1 (cs) |
| AT (1) | ATE208364T1 (cs) |
| AU (1) | AU725440B2 (cs) |
| BR (1) | BR9711315A (cs) |
| CA (1) | CA2263348C (cs) |
| CY (1) | CY2298B1 (cs) |
| CZ (1) | CZ294165B6 (cs) |
| DE (1) | DE69708130T2 (cs) |
| DK (1) | DK0925273T3 (cs) |
| ES (1) | ES2166098T3 (cs) |
| FR (1) | FR2752422B1 (cs) |
| HU (1) | HUP0004223A3 (cs) |
| ID (1) | ID17875A (cs) |
| NO (1) | NO312290B1 (cs) |
| PL (1) | PL187371B1 (cs) |
| PT (1) | PT925273E (cs) |
| RU (1) | RU2175966C2 (cs) |
| SI (1) | SI0925273T1 (cs) |
| SK (1) | SK283055B6 (cs) |
| TR (1) | TR199900329T2 (cs) |
| TW (1) | TW438764B (cs) |
| UA (1) | UA57031C2 (cs) |
| WO (1) | WO1998007681A1 (cs) |
| ZA (1) | ZA977327B (cs) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04318852A (ja) * | 1991-04-18 | 1992-11-10 | Fujitsu Ltd | レジスト・パターン形成方法 |
| CN102151262A (zh) | 2001-06-12 | 2011-08-17 | 维尔斯达医疗公司 | 用于治疗代谢失调的化合物 |
| FR2832633B1 (fr) * | 2001-11-28 | 2004-09-24 | Lipha | Composition pharmaceutique comprenant une association metformine et un acide 4-oxo-butanoique et son utilisation pour traiter le diabete |
| FR2832925B1 (fr) * | 2001-12-03 | 2006-07-14 | Lipha | Utilisation de derives de l'acide 4-oxobutanoique dans le traitement de l'inflammation |
| FR2834214B1 (fr) * | 2001-12-28 | 2004-09-24 | Lipha | Composition pharmaceutique comprenant un inhibiteur d'alpha-glucosidase et un acide 4-oxo-butanoique et son utilisation pour traiter le diabete |
| FR2834640B1 (fr) * | 2002-01-11 | 2004-09-24 | Lipha | Composition pharmaceutique comprenant une glitazone et un acide 4-oxobutanoique et son utilisation pour traiter le diabete |
| EP1556085A4 (en) * | 2002-11-01 | 2012-08-22 | Wellstat Therapeutics Corp | COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS |
| JP2006514101A (ja) * | 2002-11-08 | 2006-04-27 | ノボ・ノルデイスク・エー／エス | 肥満症の治療のための安全な化学的脱共役剤 |
| FR2849599B1 (fr) * | 2003-01-07 | 2006-12-29 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete |
| FR2849598B1 (fr) * | 2003-01-07 | 2006-09-22 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete, par augmentation du nombre de cellules des ilots de langerhans |
| ATE487474T1 (de) * | 2003-04-15 | 2010-11-15 | Wellstat Therapeutics Corp | Verbindungen zur behandlung von stoffwechselstörungen |
| ES2368692T3 (es) | 2007-12-03 | 2011-11-21 | Merck Patent Gmbh | Utilización de derivados del ácido 4-oxobutanoico en el tratamiento de patologías asociadas con trastornos inmunológicos. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190340B (it) * | 1986-06-06 | 1988-02-16 | Roussel Maestretti Spa | Derivati dell'acido 4-fenil 4-osso 2-butenoico,loro procedimento di preparazione e loro impiego come prodotti medicinali |
| DK523288A (da) * | 1987-10-06 | 1989-04-07 | Hoffmann La Roche | Aminosyrederivater |
| US5250517A (en) * | 1987-10-06 | 1993-10-05 | Hoffmann-La Roche Inc. | Renin inhibiting compounds |
| US5055466A (en) * | 1987-11-23 | 1991-10-08 | E. R. Squibb & Sons, Inc. | N-morpholino derivatives and their use as anti-hypertensive agents |
| CA1329680C (en) * | 1987-11-23 | 1994-05-17 | Harold Norris Weller, Iii | N-heterocyclic alcohol derivatives |
| FR2733750B1 (fr) | 1995-05-03 | 1997-06-13 | Synthelabo | Derives de l'acide gamma-oxo-alpha-(phenylmethyl)-5,6- dihydro-4h-thieno(3,4-c)pyrrole-5-butanoique, leur preparation et leur application en therapeutique |
-
1996
- 1996-08-16 FR FR9610254A patent/FR2752422B1/fr not_active Expired - Fee Related
-
1997
- 1997-05-08 UA UA99031301A patent/UA57031C2/uk unknown
- 1997-08-05 AT AT97936682T patent/ATE208364T1/de not_active IP Right Cessation
- 1997-08-05 EP EP97936682A patent/EP0925273B1/fr not_active Expired - Lifetime
- 1997-08-05 SK SK180-99A patent/SK283055B6/sk not_active IP Right Cessation
- 1997-08-05 CZ CZ1999498A patent/CZ294165B6/cs not_active IP Right Cessation
- 1997-08-05 WO PCT/EP1997/004252 patent/WO1998007681A1/fr not_active Ceased
- 1997-08-05 TR TR1999/00329T patent/TR199900329T2/xx unknown
- 1997-08-05 JP JP10510330A patent/JP3105545B2/ja not_active Expired - Fee Related
- 1997-08-05 SI SI9730237T patent/SI0925273T1/xx unknown
- 1997-08-05 US US09/230,849 patent/US6143787A/en not_active Expired - Fee Related
- 1997-08-05 CA CA002263348A patent/CA2263348C/en not_active Expired - Fee Related
- 1997-08-05 DK DK97936682T patent/DK0925273T3/da active
- 1997-08-05 KR KR10-1999-7001122A patent/KR100488430B1/ko not_active Expired - Fee Related
- 1997-08-05 ES ES97936682T patent/ES2166098T3/es not_active Expired - Lifetime
- 1997-08-05 CN CN97197180A patent/CN1082370C/zh not_active Expired - Fee Related
- 1997-08-05 AU AU39422/97A patent/AU725440B2/en not_active Ceased
- 1997-08-05 RU RU99105208/04A patent/RU2175966C2/ru not_active IP Right Cessation
- 1997-08-05 PT PT97936682T patent/PT925273E/pt unknown
- 1997-08-05 BR BR9711315A patent/BR9711315A/pt not_active IP Right Cessation
- 1997-08-05 DE DE69708130T patent/DE69708130T2/de not_active Expired - Lifetime
- 1997-08-05 HU HU0004223A patent/HUP0004223A3/hu unknown
- 1997-08-14 ID IDP972848A patent/ID17875A/id unknown
- 1997-08-14 ZA ZA9707327A patent/ZA977327B/xx unknown
- 1997-08-15 AR ARP970103720A patent/AR009251A1/es active IP Right Grant
- 1997-10-23 TW TW086115700A patent/TW438764B/zh active
-
1999
- 1999-02-12 PL PL97331645A patent/PL187371B1/pl not_active IP Right Cessation
- 1999-02-15 NO NO19990707A patent/NO312290B1/no not_active IP Right Cessation
-
2002
- 2002-09-24 CY CY0200057A patent/CY2298B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100805 |