DE1620728B2 - Methylsubstituierte 1,4-bis(2- phenyl-2-hydroxyaethyl)-piperazine - Google Patents
Methylsubstituierte 1,4-bis(2- phenyl-2-hydroxyaethyl)-piperazineInfo
- Publication number
- DE1620728B2 DE1620728B2 DE1965W0041788 DEW0041788A DE1620728B2 DE 1620728 B2 DE1620728 B2 DE 1620728B2 DE 1965W0041788 DE1965W0041788 DE 1965W0041788 DE W0041788 A DEW0041788 A DE W0041788A DE 1620728 B2 DE1620728 B2 DE 1620728B2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- bis
- hydroxyethyl
- piperazine
- piperazines
- 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.)
- Granted
Links
- -1 Methyl-substituted 1,4-bis (2-phenyl-2-hydroxyethyl) piperazines Chemical class 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 241000416162 Astragalus gummifer Species 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 229920001615 Tragacanth Polymers 0.000 description 8
- 229940116362 tragacanth Drugs 0.000 description 8
- 235000010487 tragacanth Nutrition 0.000 description 8
- 239000000196 tragacanth Substances 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 210000003097 mucus Anatomy 0.000 description 7
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- PIPSFCNGSZZJDI-UHFFFAOYSA-N CC1N(CC(C2=CC=CC=C2)O)C(C)C(C)N(CC(C2=CC=CC=C2)O)C1C Chemical compound CC1N(CC(C2=CC=CC=C2)O)C(C)C(C)N(CC(C2=CC=CC=C2)O)C1C PIPSFCNGSZZJDI-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- JYEFDAROPDILPN-OTXOEQGISA-N C[C@H]1N(CC(C2=CC=CC=C2)O)C[C@H](C)N(CC(C2=CC=CC=C2)O)C1 Chemical compound C[C@H]1N(CC(C2=CC=CC=C2)O)C[C@H](C)N(CC(C2=CC=CC=C2)O)C1 JYEFDAROPDILPN-OTXOEQGISA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- GMLNJYOWJZGSQF-UHFFFAOYSA-N 2-(2,5-dimethylpiperazin-1-yl)-1-phenylethanol Chemical compound CC1CNC(C)CN1CC(O)C1=CC=CC=C1 GMLNJYOWJZGSQF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- NSMWYRLQHIXVAP-OLQVQODUSA-N (2r,5s)-2,5-dimethylpiperazine Chemical compound C[C@H]1CN[C@H](C)CN1 NSMWYRLQHIXVAP-OLQVQODUSA-N 0.000 description 1
- NSMWYRLQHIXVAP-WDSKDSINSA-N (2s,5s)-2,5-dimethylpiperazine Chemical compound C[C@H]1CN[C@@H](C)CN1 NSMWYRLQHIXVAP-WDSKDSINSA-N 0.000 description 1
- ICGDKKACLISIAM-UHFFFAOYSA-N 2,3,5,6-tetramethylpiperazine Chemical compound CC1NC(C)C(C)NC1C ICGDKKACLISIAM-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- BNZPXQWIYCIDMF-UHFFFAOYSA-N 4-[dimethylamino(phenyl)methyl]-5-methylpyrazol-3-one Chemical compound CN(C)C(C=1C(N=NC=1C)=O)C1=CC=CC=C1 BNZPXQWIYCIDMF-UHFFFAOYSA-N 0.000 description 1
- NWTQPIWMYKASPX-UHFFFAOYSA-N CC(C1)NCC(C)N1C(C(C1=CC=CC=C1)OC(C)=O)=O Chemical compound CC(C1)NCC(C)N1C(C(C1=CC=CC=C1)OC(C)=O)=O NWTQPIWMYKASPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QMQBBUPJKANITL-MYXGOWFTSA-N dextropropoxyphene hydrochloride Chemical compound [H+].[Cl-].C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 QMQBBUPJKANITL-MYXGOWFTSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US432016A US3378553A (en) | 1965-02-11 | 1965-02-11 | Substituted 1, 4-bis(beta-phenyl-beta-acyloxyethyl)piperazines and their pharmaceutically acceptable acid addition salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1620728A1 DE1620728A1 (de) | 1970-08-20 |
| DE1620728B2 true DE1620728B2 (de) | 1976-12-02 |
Family
ID=23714396
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651620719 Pending DE1620719A1 (de) | 1965-02-11 | 1965-11-24 | Verfahren zur Herstellung von 1,4-Bis-(ss-phenyl-ss-acyloxyaethyl)piperazinen |
| DE1965W0041788 Granted DE1620728B2 (de) | 1965-02-11 | 1965-11-24 | Methylsubstituierte 1,4-bis(2- phenyl-2-hydroxyaethyl)-piperazine |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651620719 Pending DE1620719A1 (de) | 1965-02-11 | 1965-11-24 | Verfahren zur Herstellung von 1,4-Bis-(ss-phenyl-ss-acyloxyaethyl)piperazinen |
Country Status (5)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2081557B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-03-02 | 1973-08-10 | Cerm Cent Europ Rech Mauvernay | |
| US5190946A (en) * | 1990-02-23 | 1993-03-02 | Hoffmann-La Roche Inc. | Methods and compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995554A (en) * | 1958-09-08 | 1961-08-08 | Lakeside Lab Inc | Substituted glycolic acid esters of 1, 4-bis-(hydroxyalkyl)-piperazines |
-
1965
- 1965-02-11 US US432016A patent/US3378553A/en not_active Expired - Lifetime
- 1965-11-24 DE DE19651620719 patent/DE1620719A1/de active Pending
- 1965-11-24 DE DE1965W0041788 patent/DE1620728B2/de active Granted
-
1966
- 1966-01-24 GB GB3184/66A patent/GB1089811A/en not_active Expired
- 1966-02-10 FR FR49071A patent/FR5170M/fr not_active Expired
- 1966-02-11 DK DK72166AA patent/DK116215B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK116215B (da) | 1969-12-22 |
| FR5170M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-06-19 |
| US3378553A (en) | 1968-04-16 |
| GB1089811A (en) | 1967-11-08 |
| DE1620728A1 (de) | 1970-08-20 |
| DE1620719A1 (de) | 1970-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |