FR2485009A1 - Thiosalicylate de 2-amino-4-picoline, utile notamment comme analgesique, et son procede de preparation - Google Patents
Thiosalicylate de 2-amino-4-picoline, utile notamment comme analgesique, et son procede de preparation Download PDFInfo
- Publication number
- FR2485009A1 FR2485009A1 FR8024155A FR8024155A FR2485009A1 FR 2485009 A1 FR2485009 A1 FR 2485009A1 FR 8024155 A FR8024155 A FR 8024155A FR 8024155 A FR8024155 A FR 8024155A FR 2485009 A1 FR2485009 A1 FR 2485009A1
- Authority
- FR
- France
- Prior art keywords
- picoline
- amino
- thiosalicylate
- ethanol
- salicylate
- 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- Withdrawn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
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 4
- 230000000699 topical effect Effects 0.000 title abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 title 1
- 229960001860 salicylate Drugs 0.000 title 1
- 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 12
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229950011175 aminopicoline Drugs 0.000 claims abstract description 6
- 239000002674 ointment Substances 0.000 claims abstract description 5
- 239000006071 cream Substances 0.000 claims abstract description 3
- 239000000499 gel Substances 0.000 claims abstract description 3
- 239000006210 lotion Substances 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229940103494 thiosalicylic acid Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000007921 spray Substances 0.000 abstract description 2
- 238000007912 intraperitoneal administration Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- -1 acetylsalicylic acid - dimethylsulfoxide Chemical compound 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000005273 2-acetoxybenzoic acid group Chemical class 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
- 241001465754 Metazoa Species 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
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 206010044074 Torticollis Diseases 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000009535 clinical urine test Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 208000018197 inherited torticollis Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000002211 ultraviolet spectrum 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 |
|---|---|
| FR2485009A1 true FR2485009A1 (fr) | 1981-12-24 |
Family
ID=8479285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024155A Withdrawn FR2485009A1 (fr) | 1979-11-13 | 1980-11-13 | Thiosalicylate de 2-amino-4-picoline, utile notamment comme analgesique, et son procede de preparation |
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) |
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
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 91, no. 15, 8 octobre 1979, page 601, résumé no. 123640v, COLUMBUS, Ohio (US) & ES - A - 475 268 (ESPECIALIDADES LATINAS MEDICAMENTOS UNIVERSALES S.A.) (1er mai 1979) * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3041815A1 (de) | 1981-09-03 |
| BR8007281A (pt) | 1981-05-19 |
| 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 |
|---|---|---|---|
| ER | Errata listed in the french official journal (bopi) |
Free format text: DANS LE BULLETIN NO 52/81 |
|
| RE | Withdrawal of published application |