DE2320945A1 - Neue ester der acetylsalicylsaeure - Google Patents
Neue ester der acetylsalicylsaeureInfo
- Publication number
- DE2320945A1 DE2320945A1 DE19732320945 DE2320945A DE2320945A1 DE 2320945 A1 DE2320945 A1 DE 2320945A1 DE 19732320945 DE19732320945 DE 19732320945 DE 2320945 A DE2320945 A DE 2320945A DE 2320945 A1 DE2320945 A1 DE 2320945A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- general formula
- carbon atoms
- straight
- branched chain
- 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
- 229960001138 acetylsalicylic acid Drugs 0.000 title claims description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003902 salicylic acid esters Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 Acetylsalicyloylglycolamide Chemical compound 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 229940125890 compound Ia Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
- OYQDZGQOZBTWHB-UHFFFAOYSA-N 2-oxopropyl 2-acetyloxybenzoate Chemical compound CC(=O)COC(=O)C1=CC=CC=C1OC(C)=O OYQDZGQOZBTWHB-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7214545A FR2181449B1 (enrdf_load_html_response) | 1972-04-25 | 1972-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2320945A1 true DE2320945A1 (de) | 1973-11-08 |
Family
ID=9097445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732320945 Pending DE2320945A1 (de) | 1972-04-25 | 1973-04-25 | Neue ester der acetylsalicylsaeure |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4966645A (enrdf_load_html_response) |
| BE (1) | BE798557A (enrdf_load_html_response) |
| DE (1) | DE2320945A1 (enrdf_load_html_response) |
| ES (1) | ES414056A1 (enrdf_load_html_response) |
| FR (1) | FR2181449B1 (enrdf_load_html_response) |
| GB (1) | GB1379009A (enrdf_load_html_response) |
| IE (1) | IE37558B1 (enrdf_load_html_response) |
| NL (1) | NL7305780A (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284069B1 (en) * | 1987-03-27 | 1993-12-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyranopyridineacetic acid ester compounds and their pharmaceutical uses |
| WO2003004451A1 (en) * | 2001-07-06 | 2003-01-16 | Centrum Chemii Polimerów Polskiej Akademii Nauk | Hydroxybuttersäureester von acetylsalicylic acid, their methods of production and application as well as drugs containing them |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199576A (en) | 1976-12-15 | 1980-04-22 | The Procter & Gamble Company | Analgesic and anti-inflammatory compositions for topical application |
| DE3520786A1 (de) * | 1985-06-10 | 1986-12-11 | Puma-Sportschuhfabriken Rudolf Dassler Kg, 8522 Herzogenaurach | Schuh fuer rehabilitationszwecke |
| AU2005203988B2 (en) * | 2004-01-07 | 2010-11-11 | Seikagaku Corporation | Hyaluronic acid derivative and drug containing the same |
| US11958808B2 (en) | 2018-12-29 | 2024-04-16 | Zhejiang Hanmai Pharmaceutical Technology Co., Ltd. | Acetylsalicylic acid derivative and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1220447A (en) * | 1967-04-19 | 1971-01-27 | Wyeth John & Brother Ltd | Salicylic acid derivatives |
-
1972
- 1972-04-25 FR FR7214545A patent/FR2181449B1/fr not_active Expired
-
1973
- 1973-04-20 BE BE130287A patent/BE798557A/xx unknown
- 1973-04-25 GB GB1970773A patent/GB1379009A/en not_active Expired
- 1973-04-25 ES ES414056A patent/ES414056A1/es not_active Expired
- 1973-04-25 IE IE64173A patent/IE37558B1/xx unknown
- 1973-04-25 DE DE19732320945 patent/DE2320945A1/de active Pending
- 1973-04-25 NL NL7305780A patent/NL7305780A/xx unknown
- 1973-04-25 JP JP4634573A patent/JPS4966645A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0284069B1 (en) * | 1987-03-27 | 1993-12-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyranopyridineacetic acid ester compounds and their pharmaceutical uses |
| WO2003004451A1 (en) * | 2001-07-06 | 2003-01-16 | Centrum Chemii Polimerów Polskiej Akademii Nauk | Hydroxybuttersäureester von acetylsalicylic acid, their methods of production and application as well as drugs containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4966645A (enrdf_load_html_response) | 1974-06-27 |
| ES414056A1 (es) | 1976-02-01 |
| IE37558B1 (en) | 1977-08-17 |
| BE798557A (fr) | 1973-08-16 |
| NL7305780A (enrdf_load_html_response) | 1973-10-29 |
| GB1379009A (en) | 1975-01-02 |
| FR2181449B1 (enrdf_load_html_response) | 1975-11-28 |
| IE37558L (en) | 1973-10-25 |
| FR2181449A1 (enrdf_load_html_response) | 1973-12-07 |
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