GB1062070A - Thienyl glycolic acid derivatives - Google Patents
Thienyl glycolic acid derivativesInfo
- Publication number
- GB1062070A GB1062070A GB53041/64A GB5304164A GB1062070A GB 1062070 A GB1062070 A GB 1062070A GB 53041/64 A GB53041/64 A GB 53041/64A GB 5304164 A GB5304164 A GB 5304164A GB 1062070 A GB1062070 A GB 1062070A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- general formula
- reacting
- compounds
- ester
- 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
- -1 Thienyl glycolic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel compounds of the formula <FORM:1062070/C2/1> wherein R represents a cyclopentyl or cyclohexyl radical, R1 represents a hydrogen atom or a methyl group, n represents 1, 2 or 3 and R11 and R111 are the same or different and are hydrogen, alkyl of 1 to 4 carbon atoms, or together form with the nitrogen atom to which they are attached a heterocyclic nitrogen radical, acid addition salts of said compounds formed with pharmacologically acceptable organic or inorganic acids, and quaternary ammonium salts of said compounds are obtained (a) by condensing an acid of the general formula <FORM:1062070/C2/2> or a salt thereof, with a halo-amino-alkane of the general formula <FORM:1062070/C2/3> (b) by reacting a methyl ester of the general formula <FORM:1062070/C2/4> with an aminoalcohol of the general formula <FORM:1062070/C2/5> in the presence of sodium, (c) by reacting an acid of the general formula (B) with a dibromo-alkane of the formula <FORM:1062070/C2/6> thereby to obtain an omega-brominated ester of the formula <FORM:1062070/C2/7> and reacting said ester with an amine of the formula <FORM:1062070/C2/8> Pharmaceutical compositions having spasmolytic activity and containing the above compounds are administered orally, parenterally or rectally.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR959367A FR1402863A (en) | 1964-01-04 | 1964-01-04 | New derivatives of alpha-thienyl-3 glycolic acid |
| FR969102A FR3409M (en) | 1964-01-04 | 1964-03-27 | Medicinal product based on α-thienyl-3 glycolic acid derivative. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1062070A true GB1062070A (en) | 1967-03-15 |
Family
ID=26205217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53041/64A Expired GB1062070A (en) | 1964-01-04 | 1964-12-31 | Thienyl glycolic acid derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1234229B (en) |
| FR (1) | FR1402863A (en) |
| GB (1) | GB1062070A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4562267A (en) * | 1980-07-28 | 1985-12-31 | Pfizer Inc. | Intermediates of hypoglycemic 5-substituted oxazolidine-2,4-diones |
-
1964
- 1964-01-04 FR FR959367A patent/FR1402863A/en not_active Expired
- 1964-12-31 GB GB53041/64A patent/GB1062070A/en not_active Expired
-
1965
- 1965-01-02 DE DES94911A patent/DE1234229B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1234229B (en) | 1967-02-16 |
| FR1402863A (en) | 1965-06-18 |
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