DE3041815A1 - 2-amino-4-picolinthiosalicylat, verfahren zu dessen herstellung und dieses enthaltende arzneimittel - Google Patents
2-amino-4-picolinthiosalicylat, verfahren zu dessen herstellung und dieses enthaltende arzneimittelInfo
- Publication number
- DE3041815A1 DE3041815A1 DE19803041815 DE3041815A DE3041815A1 DE 3041815 A1 DE3041815 A1 DE 3041815A1 DE 19803041815 DE19803041815 DE 19803041815 DE 3041815 A DE3041815 A DE 3041815A DE 3041815 A1 DE3041815 A1 DE 3041815A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- picolinthiosalicylate
- picoline
- precipitate
- production
- 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.)
- Withdrawn
Links
- -1 2-AMINO-4-PICOLINTHIOSALICYLATE Chemical compound 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940103494 thiosalicylic acid Drugs 0.000 claims description 7
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims description 5
- 229950011175 aminopicoline Drugs 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 description 6
- FRLFYILRHPWIEA-UHFFFAOYSA-N 2-hydroxybenzoic acid;pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1.OC(=O)C1=CC=CC=C1O FRLFYILRHPWIEA-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- RBYZFFBHIPDOKO-UHFFFAOYSA-N C(C=1C(S)=CC=CC1)(=O)O.NC1=NC=CC(=C1)C Chemical compound C(C=1C(S)=CC=CC1)(=O)O.NC1=NC=CC(=C1)C RBYZFFBHIPDOKO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 208000010040 Sprains and Strains Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000007912 intraperitoneal administration Methods 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
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003873 salicylate salts Chemical class 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 231100000229 OECD 452 Chronic Toxicity Study Toxicity 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000011129 pharmaceutical packaging material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 208000026843 stiff neck Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000002562 urinalysis Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES485916A ES485916A1 (es) | 1979-11-13 | 1979-11-13 | Procedimiento de obtencion de tiosalicilato de 2-amino-4-pi-colina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3041815A1 true DE3041815A1 (de) | 1981-09-03 |
Family
ID=8479285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803041815 Withdrawn DE3041815A1 (de) | 1979-11-13 | 1980-11-06 | 2-amino-4-picolinthiosalicylat, verfahren zu dessen herstellung und dieses enthaltende arzneimittel |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE886013A (enExample) |
| BR (1) | BR8007281A (enExample) |
| CA (1) | CA1126277A (enExample) |
| DE (1) | DE3041815A1 (enExample) |
| ES (1) | ES485916A1 (enExample) |
| FR (1) | FR2485009A1 (enExample) |
| GR (1) | GR72538B (enExample) |
| IT (1) | IT1147024B (enExample) |
| PT (1) | PT71876B (enExample) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085646A1 (en) * | 1970-04-22 | 1971-12-31 | Rabot Ets David | Salicylates of aminopyridines - with analgesic and antiinflammatory activity |
-
1979
- 1979-11-13 ES ES485916A patent/ES485916A1/es not_active Expired
-
1980
- 1980-10-06 PT PT71876A patent/PT71876B/pt unknown
- 1980-10-28 CA CA363,443A patent/CA1126277A/en not_active Expired
- 1980-11-03 BE BE0/202689A patent/BE886013A/fr not_active IP Right Cessation
- 1980-11-06 DE DE19803041815 patent/DE3041815A1/de not_active Withdrawn
- 1980-11-07 BR BR8007281A patent/BR8007281A/pt unknown
- 1980-11-11 GR GR63329A patent/GR72538B/el unknown
- 1980-11-12 IT IT50139/80A patent/IT1147024B/it active
- 1980-11-13 FR FR8024155A patent/FR2485009A1/fr not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085646A1 (en) * | 1970-04-22 | 1971-12-31 | Rabot Ets David | Salicylates of aminopyridines - with analgesic and antiinflammatory activity |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8007281A (pt) | 1981-05-19 |
| FR2485009A1 (fr) | 1981-12-24 |
| PT71876A (en) | 1980-11-01 |
| CA1126277A (en) | 1982-06-22 |
| PT71876B (en) | 1981-08-31 |
| ES485916A1 (es) | 1980-08-01 |
| IT8050139A0 (it) | 1980-11-12 |
| BE886013A (fr) | 1981-03-02 |
| IT1147024B (it) | 1986-11-19 |
| GR72538B (enExample) | 1983-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8101 | Request for examination as to novelty | ||
| 8105 | Search report available | ||
| 8139 | Disposal/non-payment of the annual fee |