IE37581L - Piperazine derivatives. - Google Patents
Piperazine derivatives.Info
- Publication number
- IE37581L IE37581L IE730673A IE67373A IE37581L IE 37581 L IE37581 L IE 37581L IE 730673 A IE730673 A IE 730673A IE 67373 A IE67373 A IE 67373A IE 37581 L IE37581 L IE 37581L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- reaction
- reacting
- piperazine
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title abstract 4
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- XXLTUFBJFUFWJQ-UHFFFAOYSA-N 1-[3-(trifluoromethylsulfanyl)phenyl]piperazine Chemical compound FC(F)(F)SC1=CC=CC(N2CCNCC2)=C1 XXLTUFBJFUFWJQ-UHFFFAOYSA-N 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- -1 halogeno compound Chemical class 0.000 abstract 2
- 239000011630 iodine Chemical group 0.000 abstract 2
- 229910052740 iodine Chemical group 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1382536 Piperazine derivatives SYNTHELABO 26 April 1973 [3 May 1972] 19850/73 Heading C2C The invention comprises piperazine derivatives of the formula in which A is -(CH 2 ) n -COOR where n is an integer from 1 to 6 and R is a straight or branched alkyl radical of 1 to 6 carbon atoms, or A is -CH 2 -(CH 2 ) n -R 1 in which n is as above and R 1 is CN or COOH, and their pharmaceutically acceptable acid addition salts and, where R 1 is COOH, their pharmaceutically acceptable salts with bases. The piperazine derivatives may be prepared by (a) reacting N-(m-trifluoromethylthiophenyl)-piperazine with a halogeno compound of the formula A-X in which X is chlorine, bromine or iodine and A is as above. The reaction may be carried out by heating the two starting materials together in an inert organic solvent in the presence of an acceptor for the hydrohalic acid liberated; (b) reacting a compound of formula with a compound of formula in which one of Y and Z is CH 2 -CH 2 -X and the other is hydrogen and A and X are as above. The reaction may be carried out in an inert organic solvent in the presence of an acceptor for the hydrohalic acid liberated; (c) and in which A is -CH 2 CH 2 CN or -CH 2 -CH 2 COOR reacting together N - (m - trifluoromethylthiophenyl)-piperazine and an acrylic compound of formula CH 2 =CH-T in which T is CN or COOR. The reaction may be carried out with or without a solvent and preferably in the presence of a condensation catalyst such as benzyltrimethylammonium hydroxide. A still further method of making the compounds in which A is CH 2 -(CH 2 ) n -CN comprises reacting a compound of formula with a metallic cyanide. The compound of formula above wherein X is chlorine, bromine or iodine and n is an integer of from 1 to 6 is also claimed per se and may be prepared by the reaction of a halogenation agent with an alcohol of the formula
[GB1382536A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7215642A FR2186237B1 (en) | 1972-05-03 | 1972-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37581L true IE37581L (en) | 1973-11-03 |
| IE37581B1 IE37581B1 (en) | 1977-08-31 |
Family
ID=9097886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE673/73A IE37581B1 (en) | 1972-05-03 | 1973-04-30 | New piperazine derivatives |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS526996B2 (en) |
| BE (1) | BE798872A (en) |
| DE (1) | DE2322070A1 (en) |
| DK (1) | DK138423B (en) |
| ES (1) | ES414340A1 (en) |
| FR (1) | FR2186237B1 (en) |
| GB (1) | GB1382536A (en) |
| IE (1) | IE37581B1 (en) |
| NL (1) | NL149800B (en) |
| SE (1) | SE388198B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57137766A (en) * | 1981-02-17 | 1982-08-25 | Toyota Motor Corp | Lubricating structure of differential device |
| TW201033181A (en) | 2009-02-17 | 2010-09-16 | Lundbeck & Co As H | Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
-
1972
- 1972-05-03 FR FR7215642A patent/FR2186237B1/fr not_active Expired
-
1973
- 1973-04-26 GB GB1985073A patent/GB1382536A/en not_active Expired
- 1973-04-26 SE SE7305884A patent/SE388198B/en unknown
- 1973-04-27 BE BE130550A patent/BE798872A/en unknown
- 1973-04-30 IE IE673/73A patent/IE37581B1/en unknown
- 1973-05-02 DK DK240673AA patent/DK138423B/en unknown
- 1973-05-02 DE DE2322070A patent/DE2322070A1/en active Pending
- 1973-05-03 NL NL737306171A patent/NL149800B/en not_active IP Right Cessation
- 1973-05-03 ES ES414340A patent/ES414340A1/en not_active Expired
- 1973-05-04 JP JP48050174A patent/JPS526996B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2186237B1 (en) | 1975-10-31 |
| JPS526996B2 (en) | 1977-02-26 |
| FR2186237A1 (en) | 1974-01-11 |
| DE2322070A1 (en) | 1973-11-15 |
| NL149800B (en) | 1976-06-15 |
| NL7306171A (en) | 1973-11-06 |
| SE388198B (en) | 1976-09-27 |
| ES414340A1 (en) | 1976-05-16 |
| GB1382536A (en) | 1975-02-05 |
| BE798872A (en) | 1973-10-29 |
| JPS4947381A (en) | 1974-05-08 |
| DK138423B (en) | 1978-09-04 |
| DK138423C (en) | 1979-02-12 |
| IE37581B1 (en) | 1977-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4948892A (en) | Sulfonamid compound useful for treating cardiovascular disorders | |
| GB1513320A (en) | N-propargyl-2-phenylamino-2-imidazolines | |
| IE37581L (en) | Piperazine derivatives. | |
| ES537633A0 (en) | A PROCEDURE FOR PREPARING A CEPHEMIC COMPOUND | |
| GB1457038A (en) | Amino derivatives of 1,4-benzodioxan | |
| KR840001974A (en) | Preparation of 1- [3- (6-Fluoro-1,2-benzisoxazol-3-yl) propyl] -4- (substituted) -piperazine and -pyriridine | |
| GB1173312A (en) | Heterocyclic Compounds | |
| GB1489332A (en) | Reduced bicyclic pyridone derivatives | |
| GB1412546A (en) | Morpholine derivatives | |
| US3988371A (en) | Meta-[2-(benzylamino)-ethyl] benzoic acid amides | |
| US3972926A (en) | Substituted trifluoromethanesulfonanilides | |
| US3995046A (en) | Esters of 5-n-butylpyridine-2 carboxylic acid and pharmaceutical compositions containing these compounds | |
| US3980689A (en) | N-(2,5-dichloro-4-thiocyanatophenyl)-β-alanine | |
| GB1295040A (en) | ||
| ES419319A1 (en) | Amide derivatives of 3-benzoylphenyl-alkanoic acids | |
| EP0330910A1 (en) | Propane derivatives | |
| GB1446833A (en) | Hydroxamic acid derivatives of substituted a-aminooxycarboxylic acids and a process for the preparation thereof | |
| ES449427A1 (en) | Dithiocarbamic acid esters | |
| IE41900L (en) | TETRAHYDROFURO [3, 4-b] FURAN -2,4-DIONES | |
| GB1386038A (en) | Thiazolopyrimidine derivatives and pharmaceutical compositions containing them | |
| ES481298A1 (en) | Benzothiazocine and benzothiazonine derivatives and use | |
| JPS57106663A (en) | 1,4-disubstituted piperazine derivative and its preparation | |
| JPS5735575A (en) | Quinoxaline derivative and herbicide for agricultural and horticultural purpose | |
| IE34536L (en) | Acylaminopenicillanic acids | |
| ES502668A0 (en) | PROCEDURE FOR PREPARING A HYDROCARBON SOLUTION OF AN ALKYL SODIUM COMPOUND |