DE2809794C2 - - Google Patents
Info
- Publication number
- DE2809794C2 DE2809794C2 DE2809794A DE2809794A DE2809794C2 DE 2809794 C2 DE2809794 C2 DE 2809794C2 DE 2809794 A DE2809794 A DE 2809794A DE 2809794 A DE2809794 A DE 2809794A DE 2809794 C2 DE2809794 C2 DE 2809794C2
- Authority
- DE
- Germany
- Prior art keywords
- salt
- ethylamine
- acid
- diluent
- enantiomer
- 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
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical class FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 15
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- -1 α- monosubstituted ethylamine Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- VENQOHAPVLVQKV-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC=C1C(C)N VENQOHAPVLVQKV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- RJPLGQTZHLRZGX-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanamine Chemical compound CC(N)C1=CC=CC=C1Cl RJPLGQTZHLRZGX-UHFFFAOYSA-N 0.000 claims description 3
- DIWHJJUFVGEXGS-UHFFFAOYSA-N 1-(2-fluorophenyl)ethanamine Chemical compound CC(N)C1=CC=CC=C1F DIWHJJUFVGEXGS-UHFFFAOYSA-N 0.000 claims description 3
- DQEYVZASLGNODG-UHFFFAOYSA-N 1-(3-chlorophenyl)ethanamine Chemical compound CC(N)C1=CC=CC(Cl)=C1 DQEYVZASLGNODG-UHFFFAOYSA-N 0.000 claims description 3
- ASNVMKIDRJZXQZ-UHFFFAOYSA-N 1-(3-fluorophenyl)ethanamine Chemical compound CC(N)C1=CC=CC(F)=C1 ASNVMKIDRJZXQZ-UHFFFAOYSA-N 0.000 claims description 3
- QGCLEUGNYRXBMZ-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanamine Chemical compound CC(N)C1=CC=C(F)C=C1 QGCLEUGNYRXBMZ-UHFFFAOYSA-N 0.000 claims description 3
- UHAQMLODFYUKOM-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)ethanamine Chemical compound CC(C)C1=CC=C(C(C)N)C=C1 UHAQMLODFYUKOM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- CNVQKQRUQRLPQS-UHFFFAOYSA-N 2-(3-hydroxy-4-phenylphenyl)propanoic acid Chemical class OC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 CNVQKQRUQRLPQS-UHFFFAOYSA-N 0.000 claims description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical class C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- SQHQOKQJDYQTLB-UHFFFAOYSA-N 2-[4-(2,4-difluorophenyl)-3-fluorophenyl]propanoic acid Chemical class FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=C(F)C=C1F SQHQOKQJDYQTLB-UHFFFAOYSA-N 0.000 claims description 2
- GIADVXDSQWLFSJ-UHFFFAOYSA-N 2-[4-(2-fluorophenoxy)phenyl]propanoic acid Chemical class C1=CC(C(C(O)=O)C)=CC=C1OC1=CC=CC=C1F GIADVXDSQWLFSJ-UHFFFAOYSA-N 0.000 claims description 2
- MSUHIIYPJIGYBH-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)phenyl]propanoic acid Chemical class C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1F MSUHIIYPJIGYBH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 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
- 150000007513 acids Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229960002390 flurbiprofen Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XBWOPGDJMAJJDG-UHFFFAOYSA-N 1-cyclohexylethanamine Chemical compound CC(N)C1CCCCC1 XBWOPGDJMAJJDG-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 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 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N myrcene group Chemical group CC(=CCCC(C=C)=C)C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- 229930006720 (-)-alpha-pinene Natural products 0.000 description 1
- LXTFHNHLQMVBTK-UHFFFAOYSA-N 1-(2,6-dimethoxyphenyl)ethanamine Chemical compound COC1=CC=CC(OC)=C1C(C)N LXTFHNHLQMVBTK-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000005366 cycloalkylthio group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9697/77A GB1596032A (en) | 1977-03-08 | 1977-03-08 | Resolution of optically active 2-arylpropionic acids |
| GB194678 | 1978-01-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2809794A1 DE2809794A1 (de) | 1978-09-21 |
| DE2809794C2 true DE2809794C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-08-03 |
Family
ID=26237091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782809794 Granted DE2809794A1 (de) | 1977-03-08 | 1978-03-07 | Verfahren zur erhoehung des anteils an einem gewuenschten enantiomeren einer 2-arylpropionsaeure |
Country Status (29)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2826952A1 (de) * | 1978-06-20 | 1980-01-10 | Bayer Ag | Enantiomerentrennung von chiralen carbonsaeuren |
| PH15674A (en) * | 1979-07-06 | 1983-03-11 | Syntex Corp | Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid |
| JPS57145830A (en) * | 1981-03-06 | 1982-09-09 | Hiroyuki Nohira | Optical resolution of 2-(4-chlorophenyl)-3-methylbutanoic acid |
| JPH01126425U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-02-23 | 1989-08-29 | ||
| DE3824353A1 (de) * | 1988-07-19 | 1990-01-25 | Paz Arzneimittelentwicklung | Verfahren zur trennung von gemischen enantiomerer arylpropionsaeuren |
| DE4028906A1 (de) * | 1990-09-12 | 1992-03-19 | Paz Arzneimittelentwicklung | Arzneimittel sowie deren herstellung und deren verwendung bei der bekaempfung von schmerzen und/oder entzuendungen und/oder fieber an tieren und menschen |
| DE4319438C1 (de) * | 1993-06-11 | 1994-06-01 | Gerd Dr Dr Geislinger | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren |
| JP3782834B2 (ja) | 1994-10-26 | 2006-06-07 | 株式会社トクホン | 鎮痛抗炎症貼付剤 |
| DE19717429A1 (de) * | 1997-04-25 | 1998-12-24 | Bayer Ag | Herstellung enantiomerenreiner Biarylketocarbonsäuren |
| US20120029226A1 (en) | 2009-02-06 | 2012-02-02 | Bernardus Kaptein | Method for the synthesis of chiral alpha-aryl propionic acid derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL23268A (en) * | 1964-05-07 | 1969-02-27 | Merck & Co Inc | Anti-inflammatory preparations containing the 4-phenyl-alpha-methyl acid acetic phenyl acid |
| FR2015728A1 (en) * | 1968-04-18 | 1970-04-30 | Lilly Co Eli | Anti-inflammatory substd-phenylalkanoic acids and - derivs |
| US3686183A (en) * | 1969-03-24 | 1972-08-22 | Syntex Corp | Preparation of optical isomers of arylalkylacetic acids |
-
1978
- 1978-03-06 CS CS781413A patent/CS222255B2/cs unknown
- 1978-03-06 PT PT67743A patent/PT67743A/pt unknown
- 1978-03-06 GR GR55617A patent/GR64816B/el unknown
- 1978-03-07 YU YU540/78A patent/YU41472B/xx unknown
- 1978-03-07 FI FI780738A patent/FI66828C/fi not_active IP Right Cessation
- 1978-03-07 DK DK100878A patent/DK154418C/da not_active IP Right Cessation
- 1978-03-07 HU HU78BO1703A patent/HU178810B/hu unknown
- 1978-03-07 ES ES467606A patent/ES467606A1/es not_active Expired
- 1978-03-07 IN IN241/CAL/78A patent/IN147834B/en unknown
- 1978-03-07 IE IE467/81A patent/IE46476B1/en not_active IP Right Cessation
- 1978-03-07 CA CA298,426A patent/CA1105942A/en not_active Expired
- 1978-03-07 BG BG038943A patent/BG28567A3/xx unknown
- 1978-03-07 CH CH249378A patent/CH638482A5/de not_active IP Right Cessation
- 1978-03-07 NO NO780785A patent/NO146197C/no unknown
- 1978-03-07 IT IT48320/78A patent/IT1202818B/it active
- 1978-03-07 SU SU782588501A patent/SU784759A3/ru active
- 1978-03-07 SE SE7802603A patent/SE436422B/sv not_active IP Right Cessation
- 1978-03-07 DE DE19782809794 patent/DE2809794A1/de active Granted
- 1978-03-07 AT AT163478A patent/AT360508B/de not_active IP Right Cessation
- 1978-03-08 NL NLAANVRAGE7802520,A patent/NL189126C/xx not_active IP Right Cessation
- 1978-03-08 LU LU79186A patent/LU79186A1/xx unknown
- 1978-03-08 PL PL1978205161A patent/PL110888B1/pl unknown
- 1978-03-08 NZ NZ186644A patent/NZ186644A/xx unknown
- 1978-03-08 JP JP2644878A patent/JPS53112841A/ja active Granted
- 1978-03-08 FR FR7806692A patent/FR2383155A1/fr active Granted
- 1978-03-08 AU AU33977/78A patent/AU521708B2/en not_active Expired
- 1978-03-08 DD DD78204036A patent/DD136261A5/xx unknown
- 1978-03-11 EG EG161/78A patent/EG13345A/xx active
- 1978-03-13 PH PH20873A patent/PH13333A/en unknown
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