CA1214784A - P-oxybenzoic acid derivatives, processes for their production and their use as drugs - Google Patents
P-oxybenzoic acid derivatives, processes for their production and their use as drugsInfo
- Publication number
- CA1214784A CA1214784A CA000454746A CA454746A CA1214784A CA 1214784 A CA1214784 A CA 1214784A CA 000454746 A CA000454746 A CA 000454746A CA 454746 A CA454746 A CA 454746A CA 1214784 A CA1214784 A CA 1214784A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- chemical equivalent
- obvious chemical
- tert
- whenever prepared
- 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
Links
- 239000002253 acid Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 24
- 239000003814 drug Substances 0.000 title description 6
- 229940079593 drug Drugs 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 12
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 12
- -1 halide compounds Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- 235000010233 benzoic acid Nutrition 0.000 claims description 14
- 239000005711 Benzoic acid Substances 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims description 4
- 239000004247 glycine and its sodium salt Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229940029258 sodium glycinate Drugs 0.000 claims description 4
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- PCJOMFVVBWTYEN-UHFFFAOYSA-N 2-[[4-(2-hydroxy-4-phenylbutoxy)benzoyl]amino]acetic acid Chemical compound C=1C=C(C(=O)NCC(O)=O)C=CC=1OCC(O)CCC1=CC=CC=C1 PCJOMFVVBWTYEN-UHFFFAOYSA-N 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 101150041968 CDC13 gene Proteins 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 5
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- 239000008120 corn starch Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229930006000 Sucrose Chemical class 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
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- BFBUCSBWVCNMCW-UHFFFAOYSA-N 2-[2-(4-tert-butylphenyl)ethyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1CCC1OC1 BFBUCSBWVCNMCW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3326164A DE3326164A1 (de) | 1983-07-20 | 1983-07-20 | Neue p-oxibenzoesaeure-derivate, sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DEP3326164.4 | 1983-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1214784A true CA1214784A (en) | 1986-12-02 |
Family
ID=6204458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000454746A Expired CA1214784A (en) | 1983-07-20 | 1984-05-18 | P-oxybenzoic acid derivatives, processes for their production and their use as drugs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4582857B1 (en, 2012) |
| EP (1) | EP0133935B1 (en, 2012) |
| JP (1) | JPS6025953A (en, 2012) |
| AT (1) | ATE31527T1 (en, 2012) |
| AU (1) | AU560643B2 (en, 2012) |
| CA (1) | CA1214784A (en, 2012) |
| DE (2) | DE3326164A1 (en, 2012) |
| IE (1) | IE57702B1 (en, 2012) |
| MX (1) | MX9203752A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4717736A (en) * | 1984-01-23 | 1988-01-05 | Merck Frosst Canada, Inc. | Antagonists of slow reacting substances of anaphylaxis |
| US4778925A (en) * | 1985-12-30 | 1988-10-18 | Klinge Pharma Gmbh | New benzoic acid derivatives, as well as processes for their production and their use as pharmaceuticals |
| AU601739B2 (en) * | 1987-05-19 | 1990-09-20 | Klinge Pharma Gmbh | Para-substituted benzoic acid derivatives and methods of manufacture |
| DE3903988A1 (de) * | 1989-02-10 | 1990-08-30 | Basf Ag | Oxidierte diphenylheteroalkane, ihre herstellung und verwendung |
| DE4032037A1 (de) * | 1990-10-09 | 1992-04-16 | Klinge Co Chem Pharm Fab | Neue p-oxibenzoesaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE4119055A1 (de) * | 1991-06-10 | 1992-12-17 | Klinge Co Chem Pharm Fab | Verfahren zur herstellung der reinen enantiomere des lifibrol und seiner alkylester |
| DE4127800A1 (de) * | 1991-08-22 | 1993-02-25 | Klinge Co Chem Pharm Fab | Neue p-oxibenzoesaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE4314175C2 (de) * | 1993-04-29 | 1995-03-30 | Klinge Co Chem Pharm Fab | Modifikation II von Lifibrol |
| DE4414538A1 (de) * | 1994-04-26 | 1995-11-02 | Klinge Co Chem Pharm Fab | Präparate zur Therapie der kombinierten Hyperlipidämie mit einem Gehalt an einem p-Oxybenzoesäurederivat und einem Fibrat |
| DE4414537A1 (de) * | 1994-04-26 | 1995-11-02 | Klinge Co Chem Pharm Fab | Kombinationspräparate mit einem Gehalt an einem p-Oxybenzoesäurederivat und einem HMG-CoA-Reduktase-Hemmer |
| GB9417532D0 (en) * | 1994-08-31 | 1994-10-19 | Zeneca Ltd | Aromatic compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE689347A (en, 2012) * | 1965-12-09 | 1967-04-14 | Madan Ag | |
| BE795722A (fr) * | 1972-02-24 | 1973-06-18 | Fabre Sa Pierre | Nouveaux derives a activite anti-inflammatoire et antalgique |
| DE2342118C2 (de) * | 1973-08-21 | 1982-09-23 | Merck Patent Gmbh, 6100 Darmstadt | Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
| US4098816A (en) * | 1973-08-23 | 1978-07-04 | Beecham Group Limited | Polycyclic oxy-aromatic acid |
| DE2460689C3 (de) * | 1974-12-20 | 1980-06-26 | Klinge Pharma Gmbh & Co, 8000 Muenchen | 13-disubstituierte Propanol-(2)-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US4151302A (en) * | 1975-06-28 | 1979-04-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Araliphatic dihalogen compounds composition and method of use |
| GB1551416A (en) * | 1976-08-27 | 1979-08-30 | Beecham Group Ltd | Long chain dioxy hypolipidaemics |
| DE2735856A1 (de) * | 1977-08-09 | 1979-02-22 | Klinge Co Chem Pharm Fab | Neue 1,3-diphenoxypropan-2-on-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| FR2420522A1 (fr) * | 1978-03-20 | 1979-10-19 | Unicler | Derives de l'acide (m-benzoyl-phenoxy)-2 propionique et leurs applications comme medicaments |
| EP0056172B1 (en) * | 1981-01-09 | 1985-04-03 | FISONS plc | Phenoxy- and thiophenoxy compounds, methods for their preparation and pharmaceutical formulations containing them |
-
1983
- 1983-07-20 DE DE3326164A patent/DE3326164A1/de not_active Withdrawn
-
1984
- 1984-05-18 CA CA000454746A patent/CA1214784A/en not_active Expired
- 1984-06-11 JP JP59119735A patent/JPS6025953A/ja active Granted
- 1984-06-25 AU AU29851/84A patent/AU560643B2/en not_active Ceased
- 1984-07-17 DE DE8484108419T patent/DE3468209D1/de not_active Expired
- 1984-07-17 AT AT84108419T patent/ATE31527T1/de not_active IP Right Cessation
- 1984-07-17 EP EP84108419A patent/EP0133935B1/de not_active Expired
- 1984-07-19 IE IE1866/84A patent/IE57702B1/en not_active IP Right Cessation
- 1984-07-20 US US90/003103A patent/US4582857B1/en not_active Expired - Lifetime
-
1992
- 1992-06-29 MX MX9203752A patent/MX9203752A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0133935B1 (de) | 1987-12-23 |
| US4582857B1 (en) | 1994-02-15 |
| IE57702B1 (en) | 1993-03-10 |
| EP0133935A3 (en) | 1985-05-15 |
| AU560643B2 (en) | 1987-04-09 |
| DE3468209D1 (en) | 1988-02-04 |
| DE3326164A1 (de) | 1985-01-31 |
| US4582857A (en) | 1986-04-15 |
| JPH0114898B2 (en, 2012) | 1989-03-14 |
| AU2985184A (en) | 1985-01-24 |
| JPS6025953A (ja) | 1985-02-08 |
| MX9203752A (es) | 1992-09-01 |
| EP0133935A2 (de) | 1985-03-13 |
| ATE31527T1 (de) | 1988-01-15 |
| IE841866L (en) | 1985-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |