GB1047860A - 4-(piperazinoalkyl)-pyrazoles and their preparation - Google Patents
4-(piperazinoalkyl)-pyrazoles and their preparationInfo
- Publication number
- GB1047860A GB1047860A GB43998/65A GB4399865A GB1047860A GB 1047860 A GB1047860 A GB 1047860A GB 43998/65 A GB43998/65 A GB 43998/65A GB 4399865 A GB4399865 A GB 4399865A GB 1047860 A GB1047860 A GB 1047860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- pyrazole
- carbon atoms
- compound
- 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 14
- 125000004432 carbon atom Chemical group C* 0.000 abstract 13
- 238000006243 chemical reaction Methods 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- -1 methylene dioxy group Chemical group 0.000 abstract 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- WOXHPHOZJMLUFE-UHFFFAOYSA-N 1-benzylpyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CC1=CC=CC=C1 WOXHPHOZJMLUFE-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 150000003388 sodium compounds Chemical class 0.000 abstract 2
- CWBMBPVEJCZCAP-UHFFFAOYSA-N 1-(1-benzylpyrazol-4-yl)-N'-phenylpropane-1,3-diamine Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C(N)CCNC1=CC=CC=C1 CWBMBPVEJCZCAP-UHFFFAOYSA-N 0.000 abstract 1
- PQLGYAJXYGHIEC-UHFFFAOYSA-N 1-benzyl-4-(3-chloropropyl)pyrazole Chemical compound C1=C(CCCCl)C=NN1CC1=CC=CC=C1 PQLGYAJXYGHIEC-UHFFFAOYSA-N 0.000 abstract 1
- ZOULZSYHBBKFHR-UHFFFAOYSA-N 1-benzyl-4-(4-chlorobutyl)pyrazole Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CCCCCl ZOULZSYHBBKFHR-UHFFFAOYSA-N 0.000 abstract 1
- OKPKXEIAUSZYCE-UHFFFAOYSA-N 1-benzyl-4-(7-chloroheptyl)pyrazole Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CCCCCCCCl OKPKXEIAUSZYCE-UHFFFAOYSA-N 0.000 abstract 1
- LICUQKXVLVPMBL-UHFFFAOYSA-N 1-benzyl-4-(9-chlorononyl)pyrazole Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CCCCCCCCCCl LICUQKXVLVPMBL-UHFFFAOYSA-N 0.000 abstract 1
- AKQAJYLKBCWJBV-UHFFFAOYSA-N 1-benzylpyrazole Chemical compound C1=CC=NN1CC1=CC=CC=C1 AKQAJYLKBCWJBV-UHFFFAOYSA-N 0.000 abstract 1
- UFYZSPYVYKTZCA-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)propan-1-amine Chemical compound CN1C=C(CCCN)C=N1 UFYZSPYVYKTZCA-UHFFFAOYSA-N 0.000 abstract 1
- AOUBDFGPEIUYNH-UHFFFAOYSA-N 4-(1-benzylpyrazol-4-yl)butan-1-ol Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CCCCO AOUBDFGPEIUYNH-UHFFFAOYSA-N 0.000 abstract 1
- LCYSTYZPJMVSPB-UHFFFAOYSA-N 4-(1-benzylpyrazol-4-yl)butanenitrile Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CCCC#N LCYSTYZPJMVSPB-UHFFFAOYSA-N 0.000 abstract 1
- XIMONARFMMNQBQ-UHFFFAOYSA-N 4-(3-chloropropyl)-1-methylpyrazole Chemical compound CN1C=C(CCCCl)C=N1 XIMONARFMMNQBQ-UHFFFAOYSA-N 0.000 abstract 1
- XNSHLJIISAVOIT-UHFFFAOYSA-N 4-(3-chloropropyl)-3,5-dimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1CCCCl XNSHLJIISAVOIT-UHFFFAOYSA-N 0.000 abstract 1
- VCMHOHLJDLZRFS-UHFFFAOYSA-N 4-(5-chloropentyl)-1H-pyrazole Chemical compound ClCCCCCC=1C=NNC1 VCMHOHLJDLZRFS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- ARSNVPCIQCVDOS-UHFFFAOYSA-N N-[3-(1-benzylpyrazol-4-yl)-3-iminopropyl]aniline Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C(=N)CCNC1=CC=CC=C1 ARSNVPCIQCVDOS-UHFFFAOYSA-N 0.000 abstract 1
- HYVSAFOIFXUGHL-UHFFFAOYSA-N NN.[Li] Chemical compound NN.[Li] HYVSAFOIFXUGHL-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000003950 cyclic amides Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000007943 implant Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM62985A DE1296637B (de) | 1964-11-04 | 1964-11-04 | 4-(3-Piperazinopropyl)-pyrazole, ihre Salze und Verfahren zu ihrer Herstellung |
| DE1595920A DE1595920B2 (de) | 1964-11-04 | 1965-02-09 | 4-(co-Piperazinoalkyl)-pyrazole, ihre Salze und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1047860A true GB1047860A (en) | 1966-11-09 |
Family
ID=25987625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43998/65A Expired GB1047860A (en) | 1964-11-04 | 1965-10-18 | 4-(piperazinoalkyl)-pyrazoles and their preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3367936A (cg-RX-API-DMAC10.html) |
| CH (3) | CH467280A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1595920B2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR4837M (cg-RX-API-DMAC10.html) |
| GB (1) | GB1047860A (cg-RX-API-DMAC10.html) |
| NL (1) | NL145142B (cg-RX-API-DMAC10.html) |
| SE (1) | SE337592B (cg-RX-API-DMAC10.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE663344A (cg-RX-API-DMAC10.html) * | 1964-05-04 | |||
| DE1595923A1 (de) * | 1965-02-20 | 1969-11-27 | Merck Ag E | 1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung |
| FR1510206A (fr) * | 1965-12-23 | 1968-01-19 | Ciba Geigy | Procédé de préparation de diaza-cyclo-alcanes substitués |
| FR1510315A (fr) * | 1966-02-03 | 1968-01-19 | Ciba Geigy | Procédé pour la préparation de 4-diaza-cyclo-alcano-pyrazoles substitués en position 1 par des restes hétérocycliques bicycliques |
| DE1620016C3 (de) * | 1966-07-02 | 1979-08-30 | Merck Patent Gmbh, 6100 Darmstadt | 3-{Piperazinoalkyl)-pyrazole und Verfahren zu ihrer Herstellung |
| US3491098A (en) * | 1967-05-29 | 1970-01-20 | Sterling Drug Inc | 1-((imidazolyl)-lower-alkyl)-4-substituted-piperazines |
| DE2110568A1 (de) * | 1971-03-05 | 1972-09-07 | Merck Patent Gmbh | Neue N-Acyl-(piperazinoalkyl)-pyrazole |
| HU175471B (hu) * | 1977-06-13 | 1980-08-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh proizvodnykh 3-skobka-1-pirazolil-skobka zakryta-piridazina |
| DE2906252A1 (de) * | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4411901A (en) * | 1981-12-23 | 1983-10-25 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| US4452799A (en) * | 1981-12-23 | 1984-06-05 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| US5496918A (en) * | 1991-09-23 | 1996-03-05 | Alliedsignal Inc. | Process for improving the properties of polymers |
| EP2520567A3 (en) * | 2006-02-23 | 2012-12-12 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle derivatives substituted with cyclic group |
-
1965
- 1965-02-09 DE DE1595920A patent/DE1595920B2/de not_active Withdrawn
- 1965-09-07 CH CH1133068A patent/CH467280A/de unknown
- 1965-09-07 CH CH1245665A patent/CH467278A/de unknown
- 1965-09-07 CH CH1132968A patent/CH467279A/de unknown
- 1965-10-18 GB GB43998/65A patent/GB1047860A/en not_active Expired
- 1965-10-21 SE SE13642/65A patent/SE337592B/xx unknown
- 1965-11-03 FR FR37054A patent/FR4837M/fr not_active Expired
- 1965-11-03 NL NL656514242A patent/NL145142B/xx unknown
- 1965-11-03 US US506260A patent/US3367936A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6514242A (cg-RX-API-DMAC10.html) | 1966-05-05 |
| FR4837M (cg-RX-API-DMAC10.html) | 1967-02-13 |
| CH467279A (de) | 1969-01-15 |
| NL145142B (nl) | 1975-03-17 |
| CH467280A (de) | 1969-01-15 |
| SE337592B (cg-RX-API-DMAC10.html) | 1971-08-16 |
| DE1595920A1 (de) | 1970-02-12 |
| CH467278A (de) | 1969-01-15 |
| DE1595920B2 (de) | 1978-08-10 |
| US3367936A (en) | 1968-02-06 |
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