AT235832B - Process for the preparation of new thiophene compounds - Google Patents
Process for the preparation of new thiophene compoundsInfo
- Publication number
- AT235832B AT235832B AT793862A AT793862A AT235832B AT 235832 B AT235832 B AT 235832B AT 793862 A AT793862 A AT 793862A AT 793862 A AT793862 A AT 793862A AT 235832 B AT235832 B AT 235832B
- Authority
- AT
- Austria
- Prior art keywords
- group
- preparation
- carbon atoms
- salts
- compound
- Prior art date
Links
- 150000003577 thiophenes Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- -1 thiophene compound Chemical class 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
EMI1.2
EMI1.3
EMI1.4
EMI1.5
EMI1.6
EMI1.7
<Desc/Clms Page number 2>
worin Alk2, Alk, R , R und R4. die vorstehend angegebene Bedeutung haben, mit einer Verbindung der Formel III :
EMI2.1
umsetzt. Hiebei entsteht unter Anlagerung des Thienylrestes eine Thiophenverbindung der oben angegebenen allgemeinen Formel I.
Die so erhaltenen Basen können mit Hilfe von anorganischen oder organischen Säuren in die entsprechenden Salze übergeführt werden. Man kann auch mit Hilfe von Alkalihalogeniden oder andern Alkylsäurederivaten die entsprechenden quartären Salze gewinnen.'
Die neuen Verbindungen und ihre Salze haben wertvolle zentralstimulierende und coronarerweiternde Eigenschaften.
Beispiel : Eine Lösung von 12, 8 g Butyllithium (0,2 Mol) in 20 ml absolutem Äther wird auf 15 C gekühlt. Dann lässt man 8, 4 g Thiophen (0, 1 Mol) bei dieser Temperatur zutropfen. Nach 1/2 h wird auf 5 C gekühlt und es werden 26, 7 g (0, 1 Mol) 2-{N-[3' Phenyl-3'-oxo-propyl-(1')]}-amino-3-phenyl- - propan in Äther zugegeben. Nach der Zugabe wird noch 1 h lang gerührt und dann unter Kühlung mit wässeriger Ammoniumchloridlösung zersetzt. Die Ätherschicht wird getrennt und in üblicher Weise aufgearbeitet. Das entstandene 2- {N-[3'-Phenyl-3'-thienyl-3'-hydroxy-propyl-(1')]}-amino-3-henyl-propan hat einen Siedepunkt von 235 bis 241 C bei 2 mm Vakuum. Die Base bildet ein Hydrochlorid vom Schmelzpunkt 190 C.
<Desc / Clms Page number 1>
EMI1.1
EMI1.2
EMI1.3
EMI1.4
EMI1.5
EMI1.6
EMI1.7
<Desc / Clms Page number 2>
wherein Alk2, Alk, R, R and R4. have the meaning given above, with a compound of the formula III:
EMI2.1
implements. A thiophene compound of the above general formula I is formed with addition of the thienyl radical.
The bases obtained in this way can be converted into the corresponding salts with the aid of inorganic or organic acids. The corresponding quaternary salts can also be obtained with the aid of alkali halides or other alkyl acid derivatives.
The new compounds and their salts have valuable central stimulating and coronary expanding properties.
Example: A solution of 12.8 g of butyllithium (0.2 mol) in 20 ml of absolute ether is cooled to 15 ° C. Then 8.4 g of thiophene (0.1 mol) are added dropwise at this temperature. After 1/2 h the mixture is cooled to 5 ° C. and 26.7 g (0.1 mol) of 2- {N- [3 'phenyl-3'-oxo-propyl- (1')]} - amino-3 are obtained -phenyl- - propane in ether added. After the addition, the mixture is stirred for a further 1 hour and then decomposed with aqueous ammonium chloride solution while cooling. The ether layer is separated and worked up in the usual way. The resulting 2- {N- [3'-phenyl-3'-thienyl-3'-hydroxypropyl- (1 ')]} - amino-3-henyl-propane has a boiling point of 235 to 241 ° C. at 2 mm Vacuum. The base forms a hydrochloride with a melting point of 190 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE235832T | 1961-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT235832B true AT235832B (en) | 1964-09-25 |
Family
ID=29722429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT793862A AT235832B (en) | 1961-11-10 | 1962-10-08 | Process for the preparation of new thiophene compounds |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT235832B (en) |
-
1962
- 1962-10-08 AT AT793862A patent/AT235832B/en active
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