GB1331505A - Derivatives of thiophene acetic acid and processes for preparing them - Google Patents
Derivatives of thiophene acetic acid and processes for preparing themInfo
- Publication number
- GB1331505A GB1331505A GB5356170A GB5356170A GB1331505A GB 1331505 A GB1331505 A GB 1331505A GB 5356170 A GB5356170 A GB 5356170A GB 5356170 A GB5356170 A GB 5356170A GB 1331505 A GB1331505 A GB 1331505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- methyl
- thiophen
- acetic acid
- 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.)
- Expired
Links
- WBMKDDSMYHLQTN-UHFFFAOYSA-N acetic acid;thiophene Chemical class CC(O)=O.C=1C=CSC=1 WBMKDDSMYHLQTN-UHFFFAOYSA-N 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- KMFYTBJSQZPFLA-UHFFFAOYSA-N 2-(3-methylthiophen-2-yl)propanoic acid Chemical compound OC(=O)C(C)C=1SC=CC=1C KMFYTBJSQZPFLA-UHFFFAOYSA-N 0.000 abstract 1
- GGTJWZPIMZYFNP-UHFFFAOYSA-N 2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(CC(O)=O)=C1 GGTJWZPIMZYFNP-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- CGBXKKNMNCKKPS-UHFFFAOYSA-N 2-hydroxy-2-(3-methylthiophen-2-yl)propanoic acid Chemical compound CC=1C=CSC=1C(C)(O)C(O)=O CGBXKKNMNCKKPS-UHFFFAOYSA-N 0.000 abstract 1
- GIWRVUADKUVEGU-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetic acid Chemical compound OC(=O)C(=O)C1=CC=CS1 GIWRVUADKUVEGU-UHFFFAOYSA-N 0.000 abstract 1
- SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical class OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 abstract 1
- LUEKBBMZPLXIQR-UHFFFAOYSA-N 4-methylthiophene-2-carbonyl chloride Chemical compound CC1=CSC(C(Cl)=O)=C1 LUEKBBMZPLXIQR-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 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 abstract 1
- 125000005131 dialkylammonium group Chemical group 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- JBOFPOVURUQQAZ-UHFFFAOYSA-N ethyl 2-(4-methylthiophen-2-yl)acetate Chemical compound CCOC(=O)CC1=CC(C)=CS1 JBOFPOVURUQQAZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—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
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR696938734A FR2068425B1 (enrdf_load_stackoverflow) | 1969-11-12 | 1969-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1331505A true GB1331505A (en) | 1973-09-26 |
Family
ID=9042907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5356170A Expired GB1331505A (en) | 1969-11-12 | 1970-11-11 | Derivatives of thiophene acetic acid and processes for preparing them |
Country Status (12)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2139215A (en) * | 1983-04-28 | 1984-11-07 | Roussel Uclaf | Production of thiophene acetic acid compounds |
| US5561151A (en) * | 1992-03-13 | 1996-10-01 | Sepracor Inc. | Antipyretic and analgesic methods of using optically pure R-etodolac |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2203625A1 (en) * | 1972-10-24 | 1974-05-17 | Roussel Uclaf | 2-Benzoyl-5-thiazolyl alkanoic acids - as anti-inflammatories and analgesics prepdfrom a phenyl thio glyoxylamide and a 3-bromo 3-benzoyl alkanoic ester |
| FR2319340A1 (fr) * | 1975-07-28 | 1977-02-25 | Roussel Uclaf | Nouveau sel de l'acide a-methyl benzoyl-5 thiophene-2 acetique, procede de preparation et application a titre de medicament |
| GB8525716D0 (en) * | 1985-10-18 | 1985-11-20 | Roussel Lab Ltd | Chemical compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1139164A (en) * | 1966-12-05 | 1969-01-08 | Parke Davis & Co | New heterocyclic acetic acid compounds and methods for their production |
| ES356485A1 (es) * | 1967-07-26 | 1970-01-16 | Mcneilab Inc | Un procedimiento para la preparacion de nuevos acidos 5- aroilpirrol-2-carboxilicos y derivados de acido carboxilico. |
-
1969
- 1969-11-12 FR FR696938734A patent/FR2068425B1/fr not_active Expired
-
1970
- 1970-10-19 IL IL35485A patent/IL35485A/xx unknown
- 1970-11-06 DK DK564770AA patent/DK126203B/da not_active IP Right Cessation
- 1970-11-09 CH CH1659570A patent/CH534172A/fr not_active IP Right Cessation
- 1970-11-09 CH CH1514172A patent/CH533635A/fr not_active IP Right Cessation
- 1970-11-10 OA OA54083A patent/OA03518A/xx unknown
- 1970-11-10 BE BE758741A patent/BE758741A/fr not_active IP Right Cessation
- 1970-11-10 NL NLAANVRAGE7016412,A patent/NL168837C/xx not_active IP Right Cessation
- 1970-11-10 AT AT1012470A patent/AT298480B/de active
- 1970-11-11 ES ES385419A patent/ES385419A1/es not_active Expired
- 1970-11-11 GB GB5356170A patent/GB1331505A/en not_active Expired
- 1970-11-12 SE SE7015318A patent/SE377570B/xx unknown
- 1970-11-12 ZA ZA707669A patent/ZA707669B/xx unknown
-
1971
- 1971-10-29 ES ES396495A patent/ES396495A2/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2139215A (en) * | 1983-04-28 | 1984-11-07 | Roussel Uclaf | Production of thiophene acetic acid compounds |
| US5561151A (en) * | 1992-03-13 | 1996-10-01 | Sepracor Inc. | Antipyretic and analgesic methods of using optically pure R-etodolac |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AT298480B (de) | 1972-05-10 |
| FR2068425A1 (enrdf_load_stackoverflow) | 1971-08-27 |
| FR2068425B1 (enrdf_load_stackoverflow) | 1973-01-12 |
| BE758741A (fr) | 1971-05-10 |
| ES385419A1 (es) | 1973-04-16 |
| DE2055264A1 (de) | 1971-05-19 |
| DK126203B (da) | 1973-06-18 |
| CH533635A (fr) | 1973-02-15 |
| IL35485A0 (en) | 1970-12-24 |
| ZA707669B (en) | 1971-12-29 |
| ES396495A2 (es) | 1974-05-16 |
| OA03518A (fr) | 1971-03-30 |
| SE377570B (enrdf_load_stackoverflow) | 1975-07-14 |
| DE2055264B2 (de) | 1975-09-25 |
| CH534172A (fr) | 1973-02-28 |
| NL7016412A (enrdf_load_stackoverflow) | 1971-05-14 |
| NL168837C (nl) | 1982-05-17 |
| IL35485A (en) | 1974-03-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| PE20 | Patent expired after termination of 20 years |