DE2135523A1 - Piperazinium mono (acetylsalicylat), Verfahren zu seiner Herstellung und Arznei praparate - Google Patents
Piperazinium mono (acetylsalicylat), Verfahren zu seiner Herstellung und Arznei praparateInfo
- Publication number
- DE2135523A1 DE2135523A1 DE19712135523 DE2135523A DE2135523A1 DE 2135523 A1 DE2135523 A1 DE 2135523A1 DE 19712135523 DE19712135523 DE 19712135523 DE 2135523 A DE2135523 A DE 2135523A DE 2135523 A1 DE2135523 A1 DE 2135523A1
- Authority
- DE
- Germany
- Prior art keywords
- piperazinium
- mono
- acetylsalicylic acid
- diethyl ether
- manufacture
- 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.)
- Pending
Links
- REZBKSNVLLJTRH-UHFFFAOYSA-N 2-acetyloxybenzoic acid;piperazine Chemical compound C1CNCCN1.CC(=O)OC1=CC=CC=C1C(O)=O REZBKSNVLLJTRH-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 26
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 21
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229940068372 acetyl salicylate Drugs 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- -1 acetylsalicyl Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 229960001860 salicylate Drugs 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- YOAMPPADXGVWIC-UHFFFAOYSA-N C(C)(=O)OC=1C(C(=O)[O-])=CC=CC1.C(C)(=O)OC=1C(C(=O)[O-])=CC=CC1.[NH2+]1CCNCC1.[NH2+]1CCNCC1 Chemical compound C(C)(=O)OC=1C(C(=O)[O-])=CC=CC1.C(C)(=O)OC=1C(C(=O)[O-])=CC=CC1.[NH2+]1CCNCC1.[NH2+]1CCNCC1 YOAMPPADXGVWIC-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010070840 Gastrointestinal tract irritation Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000001780 epistaxis Diseases 0.000 description 1
- 208000019754 hemorrhagic gastroenteritis Diseases 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000000122 hyperventilation Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
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 |
|---|---|---|---|
| US5526970A | 1970-07-15 | 1970-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2135523A1 true DE2135523A1 (de) | 1972-01-20 |
Family
ID=21996783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712135523 Pending DE2135523A1 (de) | 1970-07-15 | 1971-07-15 | Piperazinium mono (acetylsalicylat), Verfahren zu seiner Herstellung und Arznei praparate |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3703519A (cg-RX-API-DMAC10.html) |
| AU (1) | AU3120871A (cg-RX-API-DMAC10.html) |
| BE (1) | BE769981A (cg-RX-API-DMAC10.html) |
| CA (1) | CA968801A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2135523A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK125468B (cg-RX-API-DMAC10.html) |
| FR (1) | FR2104788B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1351853A (cg-RX-API-DMAC10.html) |
| NL (1) | NL7109752A (cg-RX-API-DMAC10.html) |
| SE (1) | SE359836B (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA714606B (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505862A (en) * | 1981-04-14 | 1985-03-19 | Bristol-Myers Company | Diphenydramine dihydrogencitrate |
| US4401665A (en) * | 1981-04-14 | 1983-08-30 | Bristol-Myers Company | Sleep-aid composition containing an analgesic and diphenhydramine dihydrogencitrate, and method of use |
| US5961732A (en) * | 1997-06-11 | 1999-10-05 | Fsi International, Inc | Treating substrates by producing and controlling a cryogenic aerosol |
| US8470805B2 (en) * | 2009-04-30 | 2013-06-25 | Kaohsiung Medical University | Processes for preparing piperazinium salts of KMUP and use thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543570A (cg-RX-API-DMAC10.html) * | ||||
| DE591808C (de) * | 1931-04-24 | 1934-01-27 | Chem Fab Tempelhof Akt Ges | Verfahren zur Herstellung einer fuer Injektionen geeigneten Loesung von salicylsaurem Piperazin |
-
1970
- 1970-07-15 US US55269A patent/US3703519A/en not_active Expired - Lifetime
-
1971
- 1971-04-19 GB GB2586571*A patent/GB1351853A/en not_active Expired
- 1971-07-13 ZA ZA714606A patent/ZA714606B/xx unknown
- 1971-07-13 CA CA118,029A patent/CA968801A/en not_active Expired
- 1971-07-14 SE SE09133/71A patent/SE359836B/xx unknown
- 1971-07-14 AU AU31208/71A patent/AU3120871A/en not_active Expired
- 1971-07-14 BE BE769981A patent/BE769981A/xx unknown
- 1971-07-14 NL NL7109752A patent/NL7109752A/xx unknown
- 1971-07-15 DK DK350371AA patent/DK125468B/da unknown
- 1971-07-15 FR FR7125892A patent/FR2104788B1/fr not_active Expired
- 1971-07-15 DE DE19712135523 patent/DE2135523A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU3120871A (en) | 1973-01-18 |
| NL7109752A (cg-RX-API-DMAC10.html) | 1972-01-18 |
| CA968801A (en) | 1975-06-03 |
| ZA714606B (en) | 1972-07-26 |
| BE769981A (fr) | 1971-11-16 |
| DK125468B (da) | 1973-02-26 |
| GB1351853A (en) | 1974-05-01 |
| FR2104788B1 (cg-RX-API-DMAC10.html) | 1975-03-14 |
| FR2104788A1 (cg-RX-API-DMAC10.html) | 1972-04-21 |
| SE359836B (cg-RX-API-DMAC10.html) | 1973-09-10 |
| US3703519A (en) | 1972-11-21 |
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