IL50304A - 2-(4-methyl-1-piperazinyl)-4-tert butylthiazole its preparation and pharmaceutical compositions containing it - Google Patents
2-(4-methyl-1-piperazinyl)-4-tert butylthiazole its preparation and pharmaceutical compositions containing itInfo
- Publication number
- IL50304A IL50304A IL50304A IL5030474A IL50304A IL 50304 A IL50304 A IL 50304A IL 50304 A IL50304 A IL 50304A IL 5030474 A IL5030474 A IL 5030474A IL 50304 A IL50304 A IL 50304A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- tert
- methyl
- piperazinyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- KJWKKFSEVNVWPM-UHFFFAOYSA-N 4-tert-butyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C(C)(C)C)=CS1 KJWKKFSEVNVWPM-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- -1 4-methyl-l-piperazinyl Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- PVIJLUXKGBJNNI-UHFFFAOYSA-N piperazine-1-carbothioamide Chemical compound NC(=S)N1CCNCC1 PVIJLUXKGBJNNI-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- WQFWIVTXNKRNJZ-UHFFFAOYSA-N 2-piperazin-1-yl-1,3-thiazole Chemical class C1CNCCN1C1=NC=CS1 WQFWIVTXNKRNJZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229940125684 antimigraine agent Drugs 0.000 abstract description 2
- 239000002282 antimigraine agent Substances 0.000 abstract description 2
- 239000002830 appetite depressant Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 229940124332 anorexigenic agent Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ULSAJQMHTGKPIY-UHFFFAOYSA-N 1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CCl ULSAJQMHTGKPIY-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002891 anorexigenic effect Effects 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- WPASOZFIBCYNCU-UHFFFAOYSA-N 1-methylpiperazin-1-ium;thiocyanate Chemical compound [S-]C#N.C[NH+]1CCNCC1 WPASOZFIBCYNCU-UHFFFAOYSA-N 0.000 description 1
- CFURXPUTJPGOEI-UHFFFAOYSA-N 2-butyl-1,3-thiazol-3-ium chloride Chemical compound [Cl-].C(CCC)C=1SC=C[NH+]1 CFURXPUTJPGOEI-UHFFFAOYSA-N 0.000 description 1
- QOJMQILDLLFGEE-UHFFFAOYSA-N 2-butyl-1,3-thiazole Chemical compound CCCCC1=NC=CS1 QOJMQILDLLFGEE-UHFFFAOYSA-N 0.000 description 1
- QFACSDPLAUCZBD-UHFFFAOYSA-N 4-methylpiperazine-1-carbothioamide Chemical compound CN1CCN(C(N)=S)CC1 QFACSDPLAUCZBD-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH156373A CH583232A5 (cs) | 1973-02-02 | 1973-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL50304A true IL50304A (en) | 1977-05-31 |
Family
ID=4213345
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL50304A IL50304A (en) | 1973-02-02 | 1974-01-31 | 2-(4-methyl-1-piperazinyl)-4-tert butylthiazole its preparation and pharmaceutical compositions containing it |
| IL44122A IL44122A (en) | 1973-02-02 | 1974-01-31 | 2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing them |
| IL50304A IL50304A0 (en) | 1973-02-02 | 1976-08-19 | A new 2-(1-piperazinyl)-thiazole derivative its preparation and pharmaceutical compositions containing it |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44122A IL44122A (en) | 1973-02-02 | 1974-01-31 | 2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing them |
| IL50304A IL50304A0 (en) | 1973-02-02 | 1976-08-19 | A new 2-(1-piperazinyl)-thiazole derivative its preparation and pharmaceutical compositions containing it |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4064244A (cs) |
| JP (1) | JPS49102682A (cs) |
| AT (1) | AT348531B (cs) |
| BE (1) | BE810467A (cs) |
| CA (1) | CA1018168A (cs) |
| CH (1) | CH583232A5 (cs) |
| DD (1) | DD109390A5 (cs) |
| DE (1) | DE2404050A1 (cs) |
| ES (3) | ES422886A1 (cs) |
| FR (1) | FR2215960B1 (cs) |
| GB (1) | GB1461874A (cs) |
| HU (1) | HU167399B (cs) |
| IE (1) | IE40253B1 (cs) |
| IL (3) | IL50304A (cs) |
| NL (1) | NL7401253A (cs) |
| PH (1) | PH13708A (cs) |
| PL (1) | PL88592B1 (cs) |
| SE (1) | SE404801B (cs) |
| SU (1) | SU513624A3 (cs) |
| ZA (1) | ZA74679B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1518559A (en) * | 1976-04-12 | 1978-07-19 | Science Union & Cie | Naphthyl derivatives processes for their preparation an pharmaceutical compositions containing them |
| YU135378A (en) * | 1977-06-10 | 1982-08-31 | Science Union Et Cie Francis D | Process for the manufacture of new piperazine-dithiocarboxylic acid derivatives |
| EP0094498A3 (en) * | 1982-05-06 | 1985-04-03 | American Cyanamid Company | Antiatherosclerotic 1-piperazine derivatives |
| NL8601494A (nl) * | 1985-06-22 | 1987-01-16 | Sandoz Ag | Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten. |
| IT1191845B (it) * | 1986-01-20 | 1988-03-23 | Dompe Farmaceutici Spa | Alchiloli derivati farmacologicamente attivi |
| FR2612187B1 (fr) * | 1987-03-12 | 1989-07-21 | Sanofi Sa | Derives du thiazole actifs sur le systeme cholinergique, leur procede de preparation et compositions pharmaceutiques en contenant |
| US5232921A (en) * | 1987-03-12 | 1993-08-03 | Sanofi | Thiazole derivatives active on the cholinergic system, process for obtention and pharmaceutical compositions |
| DE4136579A1 (de) * | 1991-11-07 | 1993-05-13 | Rewo Chemische Werke Gmbh | Polyolpolyethersulfosuccinate, verfahren zu ihrer herstelllung und ihre verwendung |
| NZ504465A (en) * | 1997-10-14 | 2001-11-30 | Welfide Corp | 1-Phenylacylamino substituted piperazine derivatives which are 4-substituted by a heteroaryl group |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE485737A (cs) * | 1947-11-12 | |||
| US2606906A (en) * | 1948-10-14 | 1952-08-12 | American Cyanamid Co | 1-(2-pyridyl) piperazine and process of preparing same |
| BE577438A (cs) * | 1958-04-07 | |||
| US2975182A (en) * | 1959-11-16 | 1961-03-14 | Paul A J Janssen | 1-(aroylalkyl)-4-(heterocyclyl) piperazines |
| DE1595923A1 (de) * | 1965-02-20 | 1969-11-27 | Merck Ag E | 1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung |
-
1973
- 1973-02-02 CH CH156373A patent/CH583232A5/xx not_active IP Right Cessation
-
1974
- 1974-01-24 SE SE7400917A patent/SE404801B/xx unknown
- 1974-01-29 DE DE2404050A patent/DE2404050A1/de active Pending
- 1974-01-29 GB GB409074A patent/GB1461874A/en not_active Expired
- 1974-01-30 FR FR7403094A patent/FR2215960B1/fr not_active Expired
- 1974-01-30 NL NL7401253A patent/NL7401253A/xx not_active Application Discontinuation
- 1974-01-31 CA CA191,436A patent/CA1018168A/en not_active Expired
- 1974-01-31 DD DD176293A patent/DD109390A5/xx unknown
- 1974-01-31 IL IL50304A patent/IL50304A/en unknown
- 1974-01-31 IL IL44122A patent/IL44122A/en unknown
- 1974-01-31 JP JP49012296A patent/JPS49102682A/ja active Pending
- 1974-01-31 PH PH15462A patent/PH13708A/en unknown
- 1974-01-31 BE BE140433A patent/BE810467A/xx unknown
- 1974-01-31 IE IE187/74A patent/IE40253B1/xx unknown
- 1974-01-31 PL PL1974168473A patent/PL88592B1/pl unknown
- 1974-02-01 HU HUWA291A patent/HU167399B/hu unknown
- 1974-02-01 ZA ZA00740679A patent/ZA74679B/xx unknown
- 1974-02-01 AT AT80674A patent/AT348531B/de not_active IP Right Cessation
- 1974-02-02 ES ES422886A patent/ES422886A1/es not_active Expired
- 1974-12-12 SU SU2082480A patent/SU513624A3/ru active
-
1975
- 1975-06-18 US US05/588,002 patent/US4064244A/en not_active Expired - Lifetime
-
1976
- 1976-03-16 ES ES446076A patent/ES446076A1/es not_active Expired
- 1976-03-16 ES ES446077A patent/ES446077A1/es not_active Expired
- 1976-08-19 IL IL50304A patent/IL50304A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA74679B (en) | 1975-09-24 |
| IL44122A (en) | 1977-05-31 |
| FR2215960B1 (cs) | 1976-12-03 |
| AT348531B (de) | 1979-02-26 |
| ES446076A1 (es) | 1977-09-01 |
| JPS49102682A (cs) | 1974-09-27 |
| US4064244A (en) | 1977-12-20 |
| PL88592B1 (cs) | 1976-09-30 |
| DE2404050A1 (de) | 1974-08-08 |
| IE40253B1 (en) | 1979-04-25 |
| ATA80674A (de) | 1978-07-15 |
| FR2215960A1 (cs) | 1974-08-30 |
| BE810467A (fr) | 1974-07-31 |
| CH583232A5 (cs) | 1976-12-31 |
| IE40253L (en) | 1974-08-02 |
| ES446077A1 (es) | 1977-10-01 |
| ES422886A1 (es) | 1976-09-16 |
| GB1461874A (en) | 1977-01-19 |
| SU513624A3 (ru) | 1976-05-05 |
| HU167399B (cs) | 1975-09-27 |
| NL7401253A (cs) | 1974-08-06 |
| AU6506574A (en) | 1975-07-31 |
| IL44122A0 (en) | 1974-05-16 |
| IL50304A0 (en) | 1976-10-31 |
| SE404801B (sv) | 1978-10-30 |
| DD109390A5 (cs) | 1974-11-05 |
| PH13708A (en) | 1980-09-08 |
| CA1018168A (en) | 1977-09-27 |
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