DE2126597A1 - Aminothiophencarbonsäureester und Verfahren zu ihrer Herstellung - Google Patents
Aminothiophencarbonsäureester und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2126597A1 DE2126597A1 DE19712126597 DE2126597A DE2126597A1 DE 2126597 A1 DE2126597 A1 DE 2126597A1 DE 19712126597 DE19712126597 DE 19712126597 DE 2126597 A DE2126597 A DE 2126597A DE 2126597 A1 DE2126597 A1 DE 2126597A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- low molecular
- aminothiophenecarboxylic
- molecular weight
- acid
- 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.)
- Pending
Links
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical class NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 Aminothiophenecarboxylic acid ester Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 230000001754 anti-pyretic effect Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002221 antipyretic Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001760 anti-analgesic effect Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OLCZWOSYXWFUPO-UHFFFAOYSA-N 1-(1-chloroethoxy)-2-methylbenzene Chemical compound CC(Cl)OC1=CC=CC=C1C OLCZWOSYXWFUPO-UHFFFAOYSA-N 0.000 description 1
- ZZQNKNVQFOOMEW-UHFFFAOYSA-N 1-chlorobutyl acetate Chemical compound CCCC(Cl)OC(C)=O ZZQNKNVQFOOMEW-UHFFFAOYSA-N 0.000 description 1
- CGKKDGMMKSOGLM-UHFFFAOYSA-N 1-chloroethyl acetate Chemical compound CC(Cl)OC(C)=O CGKKDGMMKSOGLM-UHFFFAOYSA-N 0.000 description 1
- ATXWGWHZGZFBHI-UHFFFAOYSA-N 1-chloroethyl benzoate Chemical compound CC(Cl)OC(=O)C1=CC=CC=C1 ATXWGWHZGZFBHI-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- GMKYKFZCOYXIIS-UHFFFAOYSA-N 4-(2-chloro-3-methylanilino)thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(NC=2C(=CSC=2)C(O)=O)=C1Cl GMKYKFZCOYXIIS-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- LFFQVKIZDBSRCI-UHFFFAOYSA-N bromomethyl pyridine-3-carboxylate Chemical compound C(C1=CN=CC=C1)(=O)OCBr LFFQVKIZDBSRCI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- BDPZFQLKFUONAG-UHFFFAOYSA-N chloromethyl butanoate Chemical compound CCCC(=O)OCCl BDPZFQLKFUONAG-UHFFFAOYSA-N 0.000 description 1
- BTBBPNVBJSIADI-UHFFFAOYSA-N chloromethyl propanoate Chemical compound CCC(=O)OCCl BTBBPNVBJSIADI-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 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 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126597 DE2126597A1 (de) | 1971-05-28 | 1971-05-28 | Aminothiophencarbonsäureester und Verfahren zu ihrer Herstellung |
| CA143,066A CA983038A (en) | 1971-05-28 | 1972-05-19 | Aminothiophene-carboxylic acid esters and process for their preparation |
| ES403080A ES403080A1 (es) | 1971-05-28 | 1972-05-23 | Procedimiento para la preparacion de un ester de acido ami-notiofencarboxilico. |
| NL7206924A NL7206924A (enExample) | 1971-05-28 | 1972-05-23 | |
| GB2464072A GB1386664A (en) | 1971-05-28 | 1972-05-25 | Aminothiophene-carboxylic acid esters and process for their preparation |
| US00257180A US3795681A (en) | 1971-05-28 | 1972-05-26 | Aminothiophene-carboxylic acid esters |
| IL39546A IL39546A0 (en) | 1971-05-28 | 1972-05-26 | Aminothiophene-carboxylic acid esters and process for their preparation |
| ZA723614A ZA723614B (en) | 1971-05-28 | 1972-05-26 | Aminothiophene-carboxylic acid esters and process for their preparation |
| AT459972A AT321904B (de) | 1971-05-28 | 1972-05-26 | Verfahren zur herstellung von neuen aminothiophencarbonsäureestern |
| AU42786/72A AU4278672A (en) | 1971-05-28 | 1972-05-26 | Aminothiophene-carboxylic acid esters |
| DD163228A DD101406A5 (enExample) | 1971-05-28 | 1972-05-26 | |
| FR7218875A FR2139960B1 (enExample) | 1971-05-28 | 1972-05-26 | |
| AR242190A AR197680A1 (es) | 1971-05-28 | 1972-05-26 | Procedimiento para la preparacion de un ester de acido aminotiofencarboxilico |
| DD172612*A DD105991A5 (enExample) | 1971-05-28 | 1972-05-26 | |
| HUHO1488A HU165931B (enExample) | 1971-05-28 | 1972-05-27 | |
| BE784121A BE784121A (fr) | 1971-05-28 | 1972-05-29 | Esters d'acides aminothiophene-carboxyliques doues de proprietes anti-inflammatoires |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126597 DE2126597A1 (de) | 1971-05-28 | 1971-05-28 | Aminothiophencarbonsäureester und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2126597A1 true DE2126597A1 (de) | 1972-12-14 |
Family
ID=5809209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126597 Pending DE2126597A1 (de) | 1971-05-28 | 1971-05-28 | Aminothiophencarbonsäureester und Verfahren zu ihrer Herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3795681A (enExample) |
| AR (1) | AR197680A1 (enExample) |
| AT (1) | AT321904B (enExample) |
| AU (1) | AU4278672A (enExample) |
| BE (1) | BE784121A (enExample) |
| CA (1) | CA983038A (enExample) |
| DD (2) | DD105991A5 (enExample) |
| DE (1) | DE2126597A1 (enExample) |
| ES (1) | ES403080A1 (enExample) |
| FR (1) | FR2139960B1 (enExample) |
| GB (1) | GB1386664A (enExample) |
| HU (1) | HU165931B (enExample) |
| IL (1) | IL39546A0 (enExample) |
| NL (1) | NL7206924A (enExample) |
| ZA (1) | ZA723614B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507763A1 (de) * | 1991-04-04 | 1992-10-07 | Laevosan-Gesellschaft m.b.H. | Neue Thiophen-2-carbonsäurederivate und Verfahren zu deren Herstellung |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4032647A (en) * | 1975-06-16 | 1977-06-28 | Richardson-Merrell Inc. | Substituted thenoylacetic acid and esters |
| US4360681A (en) * | 1973-12-03 | 1982-11-23 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
| US4299968A (en) * | 1973-12-03 | 1981-11-10 | Hoffmann-La Roche Inc. | Novel thiophene compounds |
| US4317915A (en) * | 1976-08-23 | 1982-03-02 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
| US4428963A (en) | 1976-08-23 | 1984-01-31 | Hoffmann-La Roche Inc. | Novel thiophene derivatives |
-
1971
- 1971-05-28 DE DE19712126597 patent/DE2126597A1/de active Pending
-
1972
- 1972-05-19 CA CA143,066A patent/CA983038A/en not_active Expired
- 1972-05-23 ES ES403080A patent/ES403080A1/es not_active Expired
- 1972-05-23 NL NL7206924A patent/NL7206924A/xx unknown
- 1972-05-25 GB GB2464072A patent/GB1386664A/en not_active Expired
- 1972-05-26 AU AU42786/72A patent/AU4278672A/en not_active Expired
- 1972-05-26 ZA ZA723614A patent/ZA723614B/xx unknown
- 1972-05-26 DD DD172612*A patent/DD105991A5/xx unknown
- 1972-05-26 US US00257180A patent/US3795681A/en not_active Expired - Lifetime
- 1972-05-26 AR AR242190A patent/AR197680A1/es active
- 1972-05-26 IL IL39546A patent/IL39546A0/xx unknown
- 1972-05-26 AT AT459972A patent/AT321904B/de not_active IP Right Cessation
- 1972-05-26 FR FR7218875A patent/FR2139960B1/fr not_active Expired
- 1972-05-26 DD DD163228A patent/DD101406A5/xx unknown
- 1972-05-27 HU HUHO1488A patent/HU165931B/hu unknown
- 1972-05-29 BE BE784121A patent/BE784121A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0507763A1 (de) * | 1991-04-04 | 1992-10-07 | Laevosan-Gesellschaft m.b.H. | Neue Thiophen-2-carbonsäurederivate und Verfahren zu deren Herstellung |
| WO1992017472A1 (de) * | 1991-04-04 | 1992-10-15 | Laevosan Gesellschaft M.B.H. | Neue thiophen-2-carbonsäurederivate und verfahren zu deren herstellung |
| US5352692A (en) * | 1991-04-04 | 1994-10-04 | Laevosan Gesellschaft M. B. H. | Thiophene-2-carboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| AR197680A1 (es) | 1974-04-30 |
| CA983038A (en) | 1976-02-03 |
| IL39546A0 (en) | 1972-07-26 |
| GB1386664A (en) | 1975-03-12 |
| DD105991A5 (enExample) | 1974-05-20 |
| AT321904B (de) | 1975-04-25 |
| FR2139960A1 (enExample) | 1973-01-12 |
| BE784121A (fr) | 1972-11-29 |
| DD101406A5 (enExample) | 1973-11-05 |
| US3795681A (en) | 1974-03-05 |
| ES403080A1 (es) | 1975-04-16 |
| HU165931B (enExample) | 1974-12-28 |
| ZA723614B (en) | 1973-03-28 |
| AU4278672A (en) | 1973-11-29 |
| FR2139960B1 (enExample) | 1975-04-25 |
| NL7206924A (enExample) | 1972-11-30 |
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