JPS59196839A - フエニル酢酸誘導体 - Google Patents
フエニル酢酸誘導体Info
- Publication number
- JPS59196839A JPS59196839A JP58070794A JP7079483A JPS59196839A JP S59196839 A JPS59196839 A JP S59196839A JP 58070794 A JP58070794 A JP 58070794A JP 7079483 A JP7079483 A JP 7079483A JP S59196839 A JPS59196839 A JP S59196839A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid derivative
- phenylacetic acid
- trans
- reaction
- 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
Links
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical class C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- -1 hydroxycyclohexyl group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AUZUGWXLBGZUPP-UHFFFAOYSA-N 2-[4-[(2-oxocyclohexylidene)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C=C1C(=O)CCCC1 AUZUGWXLBGZUPP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CIJMTDMRJVFJTP-UHFFFAOYSA-N calcium;aluminum Chemical class [Al].[Ca+2] CIJMTDMRJVFJTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58070794A JPS59196839A (ja) | 1983-04-21 | 1983-04-21 | フエニル酢酸誘導体 |
| US06/600,372 US4595699A (en) | 1983-04-21 | 1984-04-16 | Immune system regulation using novel phenylalkanoic acid derivative |
| DK201284A DK162600C (da) | 1983-04-21 | 1984-04-18 | Oe4-(2-hydroxycyklohexylmethyl)phenylaaalkansyrederivater og fremgangsmaade til fremstilling deraf samt farmaceutiske midler indeholdende disse |
| ES531814A ES531814A0 (es) | 1983-04-21 | 1984-04-18 | Procedimiento para la preparacion de nuevos derivados de acidos fenilalcanoicos. |
| FI841594A FI80014C (fi) | 1983-04-21 | 1984-04-19 | Foerfarande foer framstaellning av terapeutiskt anvaendbara (4-/(2-hydroxi-cyklohexyl)metyl/fenyl) -alkansyraderivat. |
| CA000452517A CA1230127A (en) | 1983-04-21 | 1984-04-19 | Phenylalkanoic acid derivatives, their preparation and use |
| EP84302705A EP0123535B1 (en) | 1983-04-21 | 1984-04-19 | New phenylalkanoic acid derivatives, their preparation and use |
| DE8484302705T DE3460335D1 (en) | 1983-04-21 | 1984-04-19 | New phenylalkanoic acid derivatives, their preparation and use |
| US06/798,236 US4622421A (en) | 1983-04-21 | 1985-11-14 | Phenylalkanoic acid derivatives and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58070794A JPS59196839A (ja) | 1983-04-21 | 1983-04-21 | フエニル酢酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196839A true JPS59196839A (ja) | 1984-11-08 |
| JPH0329056B2 JPH0329056B2 (enExample) | 1991-04-23 |
Family
ID=13441797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58070794A Granted JPS59196839A (ja) | 1983-04-21 | 1983-04-21 | フエニル酢酸誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4595699A (enExample) |
| EP (1) | EP0123535B1 (enExample) |
| JP (1) | JPS59196839A (enExample) |
| CA (1) | CA1230127A (enExample) |
| DE (1) | DE3460335D1 (enExample) |
| DK (1) | DK162600C (enExample) |
| ES (1) | ES531814A0 (enExample) |
| FI (1) | FI80014C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993002999A1 (fr) * | 1991-08-10 | 1993-02-18 | Hisamitsu Pharmaceutical Co., Inc. | Derive de l'acide phenylalcanoique, production de ce compose et separation d'isomeres optiques dudit derive |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6038323A (ja) * | 1983-08-10 | 1985-02-27 | Sankyo Co Ltd | 眼科用消炎剤 |
| FR2601670B1 (fr) * | 1986-07-17 | 1988-10-07 | Cird | Nouveaux derives bicycliques aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
| US4748272A (en) * | 1986-08-01 | 1988-05-31 | Rorer Pharmaceutical Corp. | Phenoxyphenylacetates for use as potential modulators of arichidonic acid pathways |
| US5179124A (en) * | 1988-01-25 | 1993-01-12 | University Of Iowa Research Foundation | Anti-inflammatory for use in external and internal eye inflammations |
| US4968718A (en) * | 1988-01-25 | 1990-11-06 | University Of Iowa Research Foundation | Topically effective, nonsteroidal drug for use in external and internal eye inflammations |
| AU2250097A (en) | 1996-02-13 | 1997-09-02 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a leukotriene b4 receptor antagonist |
| ES2169351T3 (es) | 1996-02-13 | 2002-07-01 | Searle & Co | Combinaciones que tienen efectos inmunosupresores, que contienen inhibidores de ciclooxigenasa-2 y 5-lipoxigenasa. |
| JP2001506574A (ja) | 1996-02-13 | 2001-05-22 | ジー．ディー．サール アンド カンパニー | シクロオキシゲナーゼ―２阻害剤およびロイコトリエンａ４ヒドロラーゼ阻害剤を含有する免疫抑制効果をもつ配合物 |
| CA2495537C (en) | 2000-08-29 | 2010-03-30 | Nobex Corporation | Immunoregulatory compounds and derivatives and methods of treating diseases therewith |
| US8048924B2 (en) | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| EP1773767B1 (en) | 2004-07-07 | 2016-03-09 | Biocon Limited | Synthesis of azo bonded immunoregulatory compounds |
| KR100906478B1 (ko) | 2008-01-10 | 2009-07-08 | 강원대학교산학협력단 | 호모알렌일 알코올 유도체와 인듐을 이용한 이의 제조방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53135958A (en) * | 1977-04-05 | 1978-11-28 | Sankyo Co Ltd | Substituted phenylacetic acid derivatives and their preparation |
| JPS54103852A (en) * | 1978-01-27 | 1979-08-15 | Schering Ag | Novel phenyl acetate derivative*its manufacture and inflammation therapeutic medicine containing said derivative |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161538A (en) * | 1977-04-05 | 1979-07-17 | Sankyo Company Limited | Substituted phenylacetic acid derivatives and process for the preparation thereof |
| DE2861078D1 (en) * | 1978-07-21 | 1981-12-03 | Schering Ag | Indan-1-carboxylic acid derivatives,process for their preparation and pharmaceutical preparations containing these compounds |
| AT358018B (de) * | 1978-07-28 | 1980-08-11 | Sankyo Co | Verfahren zur herstellung von neuen substituierten phenylessigsaeuren und deren nied. alkylestern und salzen |
| JPS57106617A (en) * | 1980-12-23 | 1982-07-02 | Sankyo Co Ltd | Analgesic and anti-inflammatory agent |
-
1983
- 1983-04-21 JP JP58070794A patent/JPS59196839A/ja active Granted
-
1984
- 1984-04-16 US US06/600,372 patent/US4595699A/en not_active Expired - Lifetime
- 1984-04-18 ES ES531814A patent/ES531814A0/es active Granted
- 1984-04-18 DK DK201284A patent/DK162600C/da not_active IP Right Cessation
- 1984-04-19 FI FI841594A patent/FI80014C/fi not_active IP Right Cessation
- 1984-04-19 EP EP84302705A patent/EP0123535B1/en not_active Expired
- 1984-04-19 CA CA000452517A patent/CA1230127A/en not_active Expired
- 1984-04-19 DE DE8484302705T patent/DE3460335D1/de not_active Expired
-
1985
- 1985-11-14 US US06/798,236 patent/US4622421A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53135958A (en) * | 1977-04-05 | 1978-11-28 | Sankyo Co Ltd | Substituted phenylacetic acid derivatives and their preparation |
| JPS54103852A (en) * | 1978-01-27 | 1979-08-15 | Schering Ag | Novel phenyl acetate derivative*its manufacture and inflammation therapeutic medicine containing said derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993002999A1 (fr) * | 1991-08-10 | 1993-02-18 | Hisamitsu Pharmaceutical Co., Inc. | Derive de l'acide phenylalcanoique, production de ce compose et separation d'isomeres optiques dudit derive |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8506575A1 (es) | 1985-08-01 |
| JPH0329056B2 (enExample) | 1991-04-23 |
| DK201284A (da) | 1984-10-22 |
| FI80014C (fi) | 1990-04-10 |
| CA1230127A (en) | 1987-12-08 |
| US4622421A (en) | 1986-11-11 |
| EP0123535A1 (en) | 1984-10-31 |
| FI841594L (fi) | 1984-10-22 |
| DK162600C (da) | 1992-04-06 |
| DE3460335D1 (en) | 1986-08-28 |
| DK162600B (da) | 1991-11-18 |
| EP0123535B1 (en) | 1986-07-23 |
| US4595699A (en) | 1986-06-17 |
| FI841594A0 (fi) | 1984-04-19 |
| ES531814A0 (es) | 1985-08-01 |
| FI80014B (fi) | 1989-12-29 |
| DK201284D0 (da) | 1984-04-18 |
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