GB1149110A - 1-(thiazolyl-5-alkyl)-4-(pyridyl-2)-piperazines - Google Patents
1-(thiazolyl-5-alkyl)-4-(pyridyl-2)-piperazinesInfo
- Publication number
- GB1149110A GB1149110A GB14989/68A GB1498968A GB1149110A GB 1149110 A GB1149110 A GB 1149110A GB 14989/68 A GB14989/68 A GB 14989/68A GB 1498968 A GB1498968 A GB 1498968A GB 1149110 A GB1149110 A GB 1149110A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- compound
- reacted
- prepared
- reaction
- 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
- 150000001875 compounds Chemical class 0.000 abstract 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- 208000010513 Stupor Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- -1 for example Chemical compound 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,149,110. 1 - (Thiazolyl - 5 - alkyl) - 4- (pyridyl-2)-piperazines. E. MERCK A.G. 28 March, 1968 [20 April, 1967], No. 14989/68. Heading C2C. Novel compounds of the general formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP>, which may be the same or different, are hydrogen atoms or alkyl radicals containing up to 4 carbon atoms and A is a straight or branched chain alkylene radical containing 2-6 carbon atoms, and the acid addition salts thereof, are prepared by numerous methods, examples of which are as follows: (a) a compound of the general Formula II wherein X is chlorine, bromine or iodine, is reacted with a compound of the general Formula (b) a compound of the general Formula IV is reacted with a pyridyl derivative of the general formula (c) a compound of the general Formula VI is reacted with a compound of the general formula wherein X<SP>1</SP> is a halogen atom or wherein the two substitutents X<SP>1</SP> together represent an oxygen or sulphur atom; (d) a compound of the general Formula X is reacted with a dihalo ethane of the formula X-CH 2 -CH 2 -X; (f) a compound with unsaturation in the chain A is hydrogenated to give the corresponding compound wherein A is a saturated chain; or (g) a compound of the general formula wherein B and D represent sulphur or oxygen atoms is reacted with an agent generating sulphur and an agent which strips off the elements of hydrogen sulphide, for example, phosphorus pentasulphide. Halides of the Formula II above are prepared by halogenation of the corresponding omegahydroxy compounds. Intermediates of general Formula IV above are prepared by reaction of the intermediate halides above with a piperazine. Amines of general Formula VI above are prepared by amination of the halides mentioned above. Diamines of general Formula X above are prepared by reaction of an amine mentioned above and ethylene imine followed by reaction with a 2-bromopyridine. Pharmaceutical compositions in conventional forms for oral, parenteral or topical application and having blood pressure lowering, narcosisprolonging, narcosis-potentiating, tranquillizing and/or neuroleptic activities comprise an above novel compound and a suitable medicinal carrier therefor.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0073664 | 1967-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1149110A true GB1149110A (en) | 1969-04-16 |
Family
ID=7315173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14989/68A Expired GB1149110A (en) | 1967-04-20 | 1968-03-28 | 1-(thiazolyl-5-alkyl)-4-(pyridyl-2)-piperazines |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE1695410A1 (en) |
| ES (1) | ES352896A1 (en) |
| FR (1) | FR7405M (en) |
| GB (1) | GB1149110A (en) |
| NL (1) | NL6804594A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP88A (en) * | 1987-02-17 | 1990-06-06 | Pfizer | Arylpiperazinyl-ethyl (orbutyl) - phenyl-heterocyclic compounds. |
| US4935424A (en) * | 1988-05-27 | 1990-06-19 | Warner-Lambert Company | 4 or 5-(substituted piperazinylalkyl)-2-aminothiazoles as antipsychotic agents |
| WO1996002249A1 (en) * | 1994-07-15 | 1996-02-01 | Basf Aktiengesellschaft | Use of thiazole and thiadiazole compounds as d3 dopamine receptor ligands |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4456756A (en) * | 1981-08-03 | 1984-06-26 | Mead Johnson & Company | Spirothiazolidinyl piperazine derivatives |
| US4411901A (en) * | 1981-12-23 | 1983-10-25 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| DE3902316A1 (en) * | 1989-01-26 | 1990-08-02 | Lentia Gmbh | Novel piperazinylalkyl-3(2H)-pyridazinones, process for their preparation and their use as hypotensive agents |
-
1967
- 1967-04-20 DE DE19671695410 patent/DE1695410A1/en active Pending
-
1968
- 1968-03-28 GB GB14989/68A patent/GB1149110A/en not_active Expired
- 1968-04-02 NL NL6804594A patent/NL6804594A/xx unknown
- 1968-04-17 FR FR148295A patent/FR7405M/fr not_active Expired
- 1968-04-19 ES ES352896A patent/ES352896A1/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP88A (en) * | 1987-02-17 | 1990-06-06 | Pfizer | Arylpiperazinyl-ethyl (orbutyl) - phenyl-heterocyclic compounds. |
| US4935424A (en) * | 1988-05-27 | 1990-06-19 | Warner-Lambert Company | 4 or 5-(substituted piperazinylalkyl)-2-aminothiazoles as antipsychotic agents |
| WO1996002249A1 (en) * | 1994-07-15 | 1996-02-01 | Basf Aktiengesellschaft | Use of thiazole and thiadiazole compounds as d3 dopamine receptor ligands |
| US5958923A (en) * | 1994-07-15 | 1999-09-28 | Basf Aktiengesellschaft | Use of thiazole and thiadiazole compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR7405M (en) | 1969-11-03 |
| ES352896A1 (en) | 1969-08-01 |
| DE1695410A1 (en) | 1971-04-08 |
| NL6804594A (en) | 1968-10-21 |
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