GB974717A - Derivatives of piperazine and homo-piperazine - Google Patents
Derivatives of piperazine and homo-piperazineInfo
- Publication number
- GB974717A GB974717A GB710763A GB710763A GB974717A GB 974717 A GB974717 A GB 974717A GB 710763 A GB710763 A GB 710763A GB 710763 A GB710763 A GB 710763A GB 974717 A GB974717 A GB 974717A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazine
- methylphenyl
- chloro
- amino
- prepared
- 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
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 title abstract 2
- 150000004885 piperazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- SFLNVAVCCYTHCQ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)piperazine Chemical compound C1=C(C)C(C)=CC=C1N1CCNCC1 SFLNVAVCCYTHCQ-UHFFFAOYSA-N 0.000 abstract 1
- SWYYWGQORQVRBD-UHFFFAOYSA-N 1-(3-bromo-4-methylphenyl)piperazine Chemical compound C1=C(Br)C(C)=CC=C1N1CCNCC1 SWYYWGQORQVRBD-UHFFFAOYSA-N 0.000 abstract 1
- CBSPSOAZDYVVHQ-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-5-methyl-1,4-diazepane Chemical compound C1CNC(C)CCN1C1=CC=C(C)C(Cl)=C1 CBSPSOAZDYVVHQ-UHFFFAOYSA-N 0.000 abstract 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 abstract 1
- FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical group CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 abstract 1
- XGYLSRFSXKAYCR-UHFFFAOYSA-N 2-chloro-4-methylaniline Chemical compound CC1=CC=C(N)C(Cl)=C1 XGYLSRFSXKAYCR-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 150000000994 L-ascorbates Chemical class 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000002814 niacins Chemical class 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003873 salicylate salts Chemical class 0.000 abstract 1
- 239000003198 schistosomicide agent 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
- C07D295/084—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
- C07D295/092—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 with aromatic radicals attached to the chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0974717/C1/1> and non-toxic acid addition salts thereof wherein each X is a halogen atom or a C1-4-alkyl radical; T is a piperazine, methylpiperazine, homopiperazine or methylhomopiperazine residue; Z is a straight or branched alkylene or alkenylene radical; A is an oxygen or a sulphur atom and Y is naphthyl, halonaphthyl, or <FORM:0974717/C1/2> where each R is independently a hydrogen or halogen atom or an amino, nitro, C1-4-alkylamino, di-(C1-4-alkyl) amino, C1-4-alkoxy, alkyl, alkenyl, aralkyl or cyclohexyl group, and the preparation thereof by refluxing equimolar amounts of a compound of the formula <FORM:0974717/C1/3> and a compound hal-Z-A-Y where hal is a chlorine or bromine atom, in an inert solvent and in the presence of a hydrohalide acceptor and, if desired, forming the acid addition salt. Acid addition salts include ascorbates, salicylates and nicotinates. The compounds are anti-schistosomiasis agents. 1-(3-Chloro -4- methylphenyl/piperazine is prepared from diethanolamine, 3-chloro -4- amino-toluene and hydrobromic acid. Similarly are prepared 1-(3, 4-dimethylphenyl)piperazine, 1-(3-bromo-4-methylphenyl)piperazine and 1-(3-chloro -4- methylphenyl) -5- methylhomopiperazine. Halides of the formula hal-Z-A-Y are prepared by reacting an appropriate phenol with an alkylene dibromide. A comprehensive list of such halides is given.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17533662A | 1962-02-23 | 1962-02-23 | |
| US247352A US3270004A (en) | 1962-12-26 | 1962-12-26 | Disubstituted piperazines useful as schistosomiasis agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB974717A true GB974717A (en) | 1964-11-11 |
Family
ID=26871109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB710763A Expired GB974717A (en) | 1962-02-23 | 1963-02-21 | Derivatives of piperazine and homo-piperazine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB974717A (en) |
-
1963
- 1963-02-21 GB GB710763A patent/GB974717A/en not_active Expired
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