CA1126277A - Production of novel compound - Google Patents
Production of novel compoundInfo
- Publication number
- CA1126277A CA1126277A CA363,443A CA363443A CA1126277A CA 1126277 A CA1126277 A CA 1126277A CA 363443 A CA363443 A CA 363443A CA 1126277 A CA1126277 A CA 1126277A
- Authority
- CA
- Canada
- Prior art keywords
- picoline
- amino
- thiosalicylate
- chemical equivalent
- obvious chemical
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 6
- 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 claims abstract description 19
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229950011175 aminopicoline Drugs 0.000 claims abstract description 9
- 229940103494 thiosalicylic acid Drugs 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims 1
- 230000000699 topical effect Effects 0.000 abstract description 5
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 150000003873 salicylate salts Chemical class 0.000 abstract description 2
- 150000003870 salicylic acids Chemical class 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229960001860 salicylate Drugs 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 229960001138 acetylsalicylic acid Drugs 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- -1 such as Substances 0.000 description 2
- 239000000725 suspension Substances 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
- 208000034656 Contusions 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
- 238000011887 Necropsy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 230000009519 contusion Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 208000026843 stiff neck Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940068492 thiosalicylate Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 210000002700 urine Anatomy 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 (2)
| 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 |
| ES485.916 | 1979-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126277A true CA1126277A (en) | 1982-06-22 |
Family
ID=8479285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA363,443A Expired CA1126277A (en) | 1979-11-13 | 1980-10-28 | Production of novel compound |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE886013A (ref) |
| BR (1) | BR8007281A (ref) |
| CA (1) | CA1126277A (ref) |
| DE (1) | DE3041815A1 (ref) |
| ES (1) | ES485916A1 (ref) |
| FR (1) | FR2485009A1 (ref) |
| GR (1) | GR72538B (ref) |
| IT (1) | IT1147024B (ref) |
| PT (1) | PT71876B (ref) |
Family Cites Families (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
Also Published As
| Publication number | Publication date |
|---|---|
| DE3041815A1 (de) | 1981-09-03 |
| BR8007281A (pt) | 1981-05-19 |
| FR2485009A1 (fr) | 1981-12-24 |
| PT71876A (en) | 1980-11-01 |
| 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 (ref) | 1983-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |