GB867273A - Piperazine derivatives - Google Patents
Piperazine derivativesInfo
- Publication number
- GB867273A GB867273A GB3681/60A GB368160A GB867273A GB 867273 A GB867273 A GB 867273A GB 3681/60 A GB3681/60 A GB 3681/60A GB 368160 A GB368160 A GB 368160A GB 867273 A GB867273 A GB 867273A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- heptylpiperazine
- carbethoxy
- alkanoyl
- 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
- 150000004885 piperazines Chemical class 0.000 title abstract 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- -1 carboalkoxy C 2-9 Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- FQRSEDUADFVZCY-UHFFFAOYSA-N ethyl 4-heptylpiperazine-1-carboxylate Chemical compound C(=O)(OCC)N1CCN(CC1)CCCCCCC FQRSEDUADFVZCY-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- IZFVIZORCOWLJA-UHFFFAOYSA-N 1-(2,5-dimethylpiperazin-1-yl)ethanone Chemical compound CC1CN(C(C)=O)C(C)CN1 IZFVIZORCOWLJA-UHFFFAOYSA-N 0.000 abstract 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 abstract 1
- GFFSNSPNXPELQE-UHFFFAOYSA-N 1-heptylpiperazine Chemical compound CCCCCCCN1CCNCC1 GFFSNSPNXPELQE-UHFFFAOYSA-N 0.000 abstract 1
- QAQPKTNTSMCSPL-UHFFFAOYSA-N 2-(2-nitropiperazin-1-yl)-1,3-thiazole Chemical class [N+](=O)([O-])C1N(CCNC1)C=1SC=CN1 QAQPKTNTSMCSPL-UHFFFAOYSA-N 0.000 abstract 1
- ANIJFZVZXZQFDH-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=C(Br)S1 ANIJFZVZXZQFDH-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000006181 N-acylation Effects 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- 230000002963 trichomonacidal 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
- C07D277/32—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/58—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
867,273. Nitro-thiazolyl-piperazines. WALLA CE & TIERNAN Inc. Feb. 2, 1960 [Feb. 20, 1959; Jan. 13, 1960], No. 3681/60. Class 2 (3). The invention comprises compounds of the formula: wherein R 1 and R 2 are each hydrogen or alkyl C 1 - 8 and R 3 is hydrogen, alkyl C 1-8 , hydroxyalkyl C 1-8 , alkanoyl C 1-8 , phenylalkanoyl C 7-14 , benzoyl, halogeno-alkanoyl C 1-8 , carbamyl, carboalkoxy C 2-9 , alkyl C 1-8 sulphonyl, alkanoyl C 1-8 amino-phenylene-sulphonyl, and acid-addition salts of the compounds in which R 3 is hydrogen, alkyl C 1-8 or hydroxyalkyl C 1-8 , and the preparation thereof by condensing 2-bromo- 5-nitrothiazole with appropriately substituted piperazines or by appropriate N-alkylations or N-acylations or, in the case where R 3 is hydrogen, by hydrolysing corresponding N-acyl derivatives and, if desired, converting basic products into their acid-addition salts. The products have trichomonacidal properties. 1-Carbethoxy-4-heptylpiperazine is prepared by treating N-carbethoxy-piperazine with heptyl bromide. N-Heptylpiperazine is prepared by hydrolysing 1-carbethoxy-4-heptylpiperazine. 1-Acetyl-2, 5-dimethylpiperazine is prepared by appropriate acetylation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US867273XA | 1959-02-20 | 1959-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB867273A true GB867273A (en) | 1961-05-03 |
Family
ID=22200488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3681/60A Expired GB867273A (en) | 1959-02-20 | 1960-02-02 | Piperazine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1136705B (en) |
| GB (1) | GB867273A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006072436A1 (en) * | 2005-01-07 | 2006-07-13 | F. Hoffmann-La Roche Ag | [4-(heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| WO2025085848A1 (en) * | 2023-10-20 | 2025-04-24 | Arrepath, Inc. | Antibacterial compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292141B (en) * | 1966-03-08 | 1969-04-10 | Giulini Gmbh Geb | Trisubstituted acrylic acids, their alkali salts and a process for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2735798A (en) * | 1956-02-21 | Acyl amevo-nitrothiazole compositions | ||
| NL72956C (en) * | 1947-11-12 |
-
1960
- 1960-02-02 GB GB3681/60A patent/GB867273A/en not_active Expired
- 1960-02-15 DE DEW27247A patent/DE1136705B/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006072436A1 (en) * | 2005-01-07 | 2006-07-13 | F. Hoffmann-La Roche Ag | [4-(heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| US7220744B2 (en) | 2005-01-07 | 2007-05-22 | Hoffman-La Roche Inc. | Monocyclic substituted phenyl methanones |
| KR100895752B1 (en) * | 2005-01-07 | 2009-04-30 | 에프. 호프만-라 로슈 아게 | [4-heteroarylpiperazin-1-yl]-2,5-substituted-phenylmethanone derivatives as glycine transporter 1glyt-1 inhibitors for the treatment of neurological and neuropsychiatric disorders |
| CN101137363B (en) * | 2005-01-07 | 2010-09-15 | 弗·哈夫曼-拉罗切有限公司 | [4- (heteroaryl) piperazin-1-yl ] - (2, 5-substituted-phenyl) methanone derivatives as glycine transporter 1(GlyT-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| WO2025085848A1 (en) * | 2023-10-20 | 2025-04-24 | Arrepath, Inc. | Antibacterial compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1136705B (en) | 1962-09-20 |
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