GB1567378A - Acetylsalicylic acid derivative process for its preparation and pharmaceutical compositions containing it - Google Patents
Acetylsalicylic acid derivative process for its preparation and pharmaceutical compositions containing it Download PDFInfo
- Publication number
- GB1567378A GB1567378A GB1531077A GB1531077A GB1567378A GB 1567378 A GB1567378 A GB 1567378A GB 1531077 A GB1531077 A GB 1531077A GB 1531077 A GB1531077 A GB 1531077A GB 1567378 A GB1567378 A GB 1567378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coagulation
- acetyl
- ynylamine
- dimethylprop
- compound
- 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
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 238000005345 coagulation Methods 0.000 claims description 26
- 230000015271 coagulation Effects 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 16
- QLODIQZORRWPLI-UHFFFAOYSA-N 2-acetyloxybenzoic acid;2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C.CC(=O)OC1=CC=CC=C1C(O)=O QLODIQZORRWPLI-UHFFFAOYSA-N 0.000 claims description 15
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 230000010100 anticoagulation Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 claims description 6
- 102000008186 Collagen Human genes 0.000 claims description 6
- 108010035532 Collagen Proteins 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 claims description 6
- 229920001436 collagen Polymers 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 241000699670 Mus sp. Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 241001237754 Algia Species 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- JJBCTCGUOQYZHK-UHFFFAOYSA-N 2-acetyloxybenzoate;(5-amino-1-carboxypentyl)azanium Chemical compound OC(=O)C(N)CCCC[NH3+].CC(=O)OC1=CC=CC=C1C([O-])=O JJBCTCGUOQYZHK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 206010013710 Drug interaction Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 239000002221 antipyretic Substances 0.000 claims description 2
- 230000000740 bleeding effect Effects 0.000 claims description 2
- 238000007705 chemical test Methods 0.000 claims description 2
- 230000007665 chronic toxicity Effects 0.000 claims description 2
- 231100000160 chronic toxicity Toxicity 0.000 claims description 2
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 claims description 2
- 210000003743 erythrocyte Anatomy 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
- 238000002575 gastroscopy Methods 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 210000002381 plasma Anatomy 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- 231100000456 subacute toxicity Toxicity 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 2
- 229940038773 trisodium citrate Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229940068372 acetyl salicylate Drugs 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection 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
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical class CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 206010053155 Epigastric discomfort Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/23—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton containing carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7702958A FR2378522A2 (fr) | 1977-01-31 | 1977-01-31 | Obtention d'une nouvelle forme d'aspirine injectable |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1567378A true GB1567378A (en) | 1980-05-14 |
Family
ID=9186226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1531077A Expired GB1567378A (en) | 1977-01-31 | 1977-04-13 | Acetylsalicylic acid derivative process for its preparation and pharmaceutical compositions containing it |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE853626A (en, 2012) |
| CH (1) | CH601170A5 (en, 2012) |
| ES (1) | ES457810A1 (en, 2012) |
| FR (1) | FR2378522A2 (en, 2012) |
| GB (1) | GB1567378A (en, 2012) |
-
1977
- 1977-01-31 FR FR7702958A patent/FR2378522A2/fr active Granted
- 1977-04-13 GB GB1531077A patent/GB1567378A/en not_active Expired
- 1977-04-14 BE BE176745A patent/BE853626A/xx unknown
- 1977-04-14 CH CH465877A patent/CH601170A5/xx not_active IP Right Cessation
- 1977-04-14 ES ES457810A patent/ES457810A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2378522A2 (fr) | 1978-08-25 |
| CH601170A5 (en, 2012) | 1978-06-30 |
| BE853626A (fr) | 1977-08-01 |
| ES457810A1 (es) | 1978-03-01 |
| FR2378522B2 (en, 2012) | 1980-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |