DE2156806C2 - Argininacetylsalicylate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen - Google Patents
Argininacetylsalicylate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische ZubereitungenInfo
- Publication number
- DE2156806C2 DE2156806C2 DE19712156806 DE2156806A DE2156806C2 DE 2156806 C2 DE2156806 C2 DE 2156806C2 DE 19712156806 DE19712156806 DE 19712156806 DE 2156806 A DE2156806 A DE 2156806A DE 2156806 C2 DE2156806 C2 DE 2156806C2
- Authority
- DE
- Germany
- Prior art keywords
- arginine
- acetylsalicylic acid
- acetylsalicylates
- acetyl salicylate
- pharmaceutical preparations
- 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
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 title claims description 13
- 239000004475 Arginine Substances 0.000 title claims description 9
- -1 Arginine acetylsalicylates Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 18
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 17
- FXXXGQLMXDIPQA-VWMHFEHESA-N 2-acetyloxybenzoic acid;(2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N.CC(=O)OC1=CC=CC=C1C(O)=O FXXXGQLMXDIPQA-VWMHFEHESA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 235000009697 arginine Nutrition 0.000 claims description 8
- 229960003121 arginine Drugs 0.000 claims description 8
- 229930064664 L-arginine Natural products 0.000 claims description 3
- 235000014852 L-arginine Nutrition 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229940110377 dl- arginine Drugs 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 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 description 4
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical class CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 239000007928 intraperitoneal injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYJDNPSQBGFFSF-WCCKRBBISA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;carbonic acid Chemical compound OC(O)=O.OC(=O)[C@@H](N)CCCNC(N)=N RYJDNPSQBGFFSF-WCCKRBBISA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| FR7042535A FR2115059B1 (show.php) | 1970-11-26 | 1970-11-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2156806A1 DE2156806A1 (de) | 1972-05-31 |
| DE2156806C2 true DE2156806C2 (de) | 1983-04-28 |
Family
ID=9064777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712156806 Expired DE2156806C2 (de) | 1970-11-26 | 1971-11-16 | Argininacetylsalicylate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2156806C2 (show.php) |
| FR (1) | FR2115059B1 (show.php) |
| GB (1) | GB1350309A (show.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2258780A1 (en) * | 1996-06-27 | 1998-03-19 | Chune Sang | Cosmetic compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1295304A (fr) * | 1956-05-07 | 1962-06-08 | Equilibre Biolog L | Nouveau sel de l'acide acétyl-salicylique et son procédé de préparation |
| GB883331A (en) * | 1959-08-28 | 1961-11-29 | Mead Johnson & Co | Stable water-soluble acetylsalicylic acid derivative |
-
1970
- 1970-11-26 FR FR7042535A patent/FR2115059B1/fr not_active Expired
-
1971
- 1971-10-29 GB GB5035671A patent/GB1350309A/en not_active Expired
- 1971-11-16 DE DE19712156806 patent/DE2156806C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2115059A1 (show.php) | 1972-07-07 |
| GB1350309A (en) | 1974-04-18 |
| FR2115059B1 (show.php) | 1974-08-30 |
| DE2156806A1 (de) | 1972-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |