GB1157277A - Cyclopropylpiperazinoalkyl-Phenothiazines and process for preparing the same - Google Patents
Cyclopropylpiperazinoalkyl-Phenothiazines and process for preparing the sameInfo
- Publication number
- GB1157277A GB1157277A GB3755866A GB3755866A GB1157277A GB 1157277 A GB1157277 A GB 1157277A GB 3755866 A GB3755866 A GB 3755866A GB 3755866 A GB3755866 A GB 3755866A GB 1157277 A GB1157277 A GB 1157277A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenothiazine
- cyclopropyl
- general formula
- cyclopropylamine
- trifluoromethyl
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
1,157,277. Phenothiazine derivatives. ELI LILLY & CO. 22 Aug., 1966, No. 37558/66. Heading C2C. Novel phenothiazine derivatives of the general formula wherein R is hydrogen or methyl and R<SP>1</SP> is chloro, trifluoromethyl, methoxy or methylthio, and pharmaceutically acceptable acid addition salts thereof are prepared (a) by heating a phenothiazine derivative of the general formula wherein X is chlorine or bromine, with N-cyclopropyl-piperazine; (b) by reacting a phenothiazine having a chlorine atom or a trifluoromethyl, methoxy or methylthio group in the 2-position with a N-cyclopropyl-piperazine derivative of the general formula wherein X is chlorine or bromine; (c) by heating a 10 - [3 - (N,N - bis - 2 - chloroethyl) - amino - propyl or - 2 - methylpropyl] - phenothiazine having a chlorine atom or a trifluoromethyl, methoxy or methylthio group in the 2-position with cyclopropylamine; or (d) by reacting a phenothiazinyl-10-carbonyl chloride having a chlorine atom or a trifluoromethyl, methoxy or methylthio group in the 2-position with 3-(4- cyclopropylpiperazino) - 1 - propanol or - 2 - methyl - 1 - propanol and heating the carbamate thus formed, followed optionally by conversion of the product to a pharmaceutically acceptable acid addition salt thereof. Pharmaceutical compositions having tranquillizing and anti-emetic properties comprise as active ingredient a phenothiazine of the first general formula above or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical carrier. N-Cyclopropyl-piperazine derivatives of the general formula wherein R<SP>2</SP> is hydrogen or -CH 2 CHRCH 2 -X and X is chloro or hydroxy, are prepared (a) by hydrolysis of 1-cyclopropyl-4-p-toluenesulphonylpiperazine, obtained by reaction of N,N-bis-(#- chloroethyl) - p - toluenesulphonamide and cyclopropylamine, to yield N-cyclopropyl-piperazine; (b) by reaction of cyclopropylamine with ethylene oxide, conversion of the N,N-bis-(#- hydroxyethyl)-cyclopropylamine thus obtained to the corresponding #-chloroethyl derivative by reaction with a chlorinating agent, followed by cyclization of the N,N-bis-(#-chloroethyl)-cyclopropylamine with an amine of the formula R<SP>2</SP>NH 2 ; or (c) by chlorination of a N-cyclopropyl-piperazine derivative of the fourth general formula above wherein R<SP>2</SP> is -CH 2 - CHR-CH 2 OH to give the corresponding derivative wherein R is -CH 2 -CHR-CH 2 -Cl. 10-(3- Chloropropyl) - 2 - trifluoromethyl - phenothiazine is prepared by reacting 2-trifluoromethylphenothiazine with 1-chloro-3-bromo-propane. Reference has been directed by the Comptroller to Specification 833,473.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR73685A FR5681M (en) | 1966-08-22 | 1966-08-22 | |
BE685833D BE685833A (en) | 1966-08-22 | 1966-08-22 | |
NL6611786A NL6611786A (en) | 1966-08-22 | 1966-08-22 | |
GB3755866A GB1157277A (en) | 1966-08-22 | 1966-08-22 | Cyclopropylpiperazinoalkyl-Phenothiazines and process for preparing the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR73685A FR5681M (en) | 1966-08-22 | 1966-08-22 | |
NL6611786A NL6611786A (en) | 1966-08-22 | 1966-08-22 | |
BE685833 | 1966-08-22 | ||
GB3755866A GB1157277A (en) | 1966-08-22 | 1966-08-22 | Cyclopropylpiperazinoalkyl-Phenothiazines and process for preparing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1157277A true GB1157277A (en) | 1969-07-02 |
Family
ID=27424860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3755866A Expired GB1157277A (en) | 1966-08-22 | 1966-08-22 | Cyclopropylpiperazinoalkyl-Phenothiazines and process for preparing the same |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE685833A (en) |
FR (1) | FR5681M (en) |
GB (1) | GB1157277A (en) |
NL (1) | NL6611786A (en) |
-
1966
- 1966-08-22 BE BE685833D patent/BE685833A/xx unknown
- 1966-08-22 GB GB3755866A patent/GB1157277A/en not_active Expired
- 1966-08-22 NL NL6611786A patent/NL6611786A/xx unknown
- 1966-08-22 FR FR73685A patent/FR5681M/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE685833A (en) | 1967-02-22 |
FR5681M (en) | 1968-01-08 |
NL6611786A (en) | 1968-02-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |