GB683337A - Improvements in or relating to the preparation of antispasmodic compounds - Google Patents
Improvements in or relating to the preparation of antispasmodic compoundsInfo
- Publication number
- GB683337A GB683337A GB23425/50A GB2342550A GB683337A GB 683337 A GB683337 A GB 683337A GB 23425/50 A GB23425/50 A GB 23425/50A GB 2342550 A GB2342550 A GB 2342550A GB 683337 A GB683337 A GB 683337A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thienyl
- cyclopentenylacetate
- cyclohexenyl
- acid
- cyclopentenyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Thiophene esters of the formula <FORM:0683337/IV (b)/1> wherein R1 is cyclopentenyl or cyclohexenyl, R11 and R111 are the same or different C1-C4 alkyl groups or together form a polymethylene chain which may be interrupted by O, S or NH, R1V is hydrogen, C1-C6 alkyl or halogen (same or different) and Alk is a C1-C6 alkylene radical (straight or branched), are prepared by esterification reactions, viz.: <FORM:0683337/IV (b)/2> reacted with the acid halide or ester (alkyl of 1-4 carbon atoms), or <FORM:0683337/IV (b)/3> reacted with the acid or its alkali salt; the reactions are preferably carried out by refluxing in a solvent such as isopropanol. The products form salts with acids, e.g. hydrochloric, hydrobromic, sulphuric, tartaric, citric and succinic. They may be quaternated, e.g. with methyl or benzyl chloride or bromide or thienylmethyl chloride. They have antispasmodic and antihistaminic activity. An example is given of the reaction between 2-thienyl-D 2-cyclopentenylacetic acid and b -diethylaminoethyl chloride to give the ester hydrochloride. Other specified products are b -piperidinoethyl 2-thienyl-D 2-cyclohexenyl- and cyclopentenylacetates, b - diethylaminoethyl 2 - thienylD 2 - cyclohexenyl, 3 - methyl - 2 - thienyl - D 2-cyclopentenyl and 4-chloro-2-thienyl-D 2-cyclohexenylacetates, b - dimethylaminoethyl 2-thienyl - D 1 - cyclopentenylacetate, b - di - isopropylaminoethyl 2 - thienyl - D 2 - cyclohexenylacetate, g - diethylamino - b - methylpropyl 2 - thienyl - D 2 - cyclopentenylacetate, b - morpholinoethyl 2 - thienyl - D 2 - cyclopentenylacetate, b - thiomorpholinomethyl 2-thienyl - D 2 - cyclohexenylacetate and b -piperazinoethyl 2 - thienyl - D 2-cyclopentenylacetate. The starting materials are obtained by reacting diethyl 2-thienylmalonate with a cyclopentenyl or cyclohexenyl halide followed by hydrolysis and decarboxylation of the resulting ester by heating with alcoholic alkali. The preparation of diethyl 2-thienyl-D 2-cyclopentenylmalonate and 2-thienyl-D 2-cyclopentenylacetic acid is described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US870272XA | 1949-10-01 | 1949-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB683337A true GB683337A (en) | 1952-11-26 |
Family
ID=22202617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23425/50A Expired GB683337A (en) | 1949-10-01 | 1950-09-25 | Improvements in or relating to the preparation of antispasmodic compounds |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE870272C (en) |
| FR (1) | FR1055804A (en) |
| GB (1) | GB683337A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2537137B1 (en) * | 1982-12-03 | 1985-07-19 | Roussel Uclaf | PROCESS FOR THE PREPARATION OF ACETIC 2-THIOPHENE ACID DERIVATIVES AND INTERMEDIATE PRODUCTS NECESSARY FOR THEIR PREPARATION |
-
1950
- 1950-09-25 GB GB23425/50A patent/GB683337A/en not_active Expired
- 1950-09-25 FR FR1055804D patent/FR1055804A/en not_active Expired
- 1950-10-01 DE DEW4143A patent/DE870272C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1055804A (en) | 1954-02-22 |
| DE870272C (en) | 1953-03-12 |
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