FR2500830A1 - Diaryl as-triazines fonctionnalisees en 2, leur procede de preparation et leur utilisation comme medicaments - Google Patents
Diaryl as-triazines fonctionnalisees en 2, leur procede de preparation et leur utilisation comme medicaments Download PDFInfo
- Publication number
- FR2500830A1 FR2500830A1 FR8104260A FR8104260A FR2500830A1 FR 2500830 A1 FR2500830 A1 FR 2500830A1 FR 8104260 A FR8104260 A FR 8104260A FR 8104260 A FR8104260 A FR 8104260A FR 2500830 A1 FR2500830 A1 FR 2500830A1
- Authority
- FR
- France
- Prior art keywords
- oxo
- triazine
- sep
- group
- alcenoxy
- 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.)
- Granted
Links
- 230000000202 analgesic effect Effects 0.000 title claims description 4
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 title 1
- 230000002152 alkylating effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- -1 DIMETHYLAMINO ETHYL Chemical class 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 15
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000003918 triazines Chemical class 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims 1
- 208000037656 Respiratory Sounds Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 206010037833 rales Diseases 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 abstract description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical class C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 abstract 1
- 241001237754 Algia Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 208000019695 Migraine disease Diseases 0.000 abstract 1
- 230000000146 antalgic effect Effects 0.000 abstract 1
- 230000002744 anti-aggregatory effect Effects 0.000 abstract 1
- 206010027599 migraine Diseases 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- 238000004809 thin layer chromatography Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 5
- 0 CC=C(C=CC(*)=C)C(C(c1ccc(*)cc1)=*=C)=C Chemical compound CC=C(C=CC(*)=C)C(C(c1ccc(*)cc1)=*=C)=C 0.000 description 4
- LZLOFGMGFADIKQ-UHFFFAOYSA-N benzene;1,4-dioxane Chemical compound C1COCCO1.C1=CC=CC=C1 LZLOFGMGFADIKQ-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GICIECWTEWJCRE-UHFFFAOYSA-N 3,4,4,7-tetramethyl-2,3-dihydro-1h-naphthalene Chemical compound CC1=CC=C2C(C)(C)C(C)CCC2=C1 GICIECWTEWJCRE-UHFFFAOYSA-N 0.000 description 1
- BMVWDUVNSGNUJC-KHOGLYSOSA-N CNC(/N=C(\C(c(cc1)ccc1N(C)C)=N)/c(cc1)ccc1N(C)C)=O Chemical compound CNC(/N=C(\C(c(cc1)ccc1N(C)C)=N)/c(cc1)ccc1N(C)C)=O BMVWDUVNSGNUJC-KHOGLYSOSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 230000001618 algogenic effect Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8104260A FR2500830A1 (fr) | 1981-03-02 | 1981-03-02 | Diaryl as-triazines fonctionnalisees en 2, leur procede de preparation et leur utilisation comme medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8104260A FR2500830A1 (fr) | 1981-03-02 | 1981-03-02 | Diaryl as-triazines fonctionnalisees en 2, leur procede de preparation et leur utilisation comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2500830A1 true FR2500830A1 (fr) | 1982-09-03 |
| FR2500830B1 FR2500830B1 (enExample) | 1984-02-10 |
Family
ID=9255836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8104260A Granted FR2500830A1 (fr) | 1981-03-02 | 1981-03-02 | Diaryl as-triazines fonctionnalisees en 2, leur procede de preparation et leur utilisation comme medicaments |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2500830A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2544313A1 (fr) * | 1983-04-14 | 1984-10-19 | Fabre Sa Pierre | Les n-cycloalcoyl methyl-2 oxo-3 diaryl 5-6 as triazines, leur procede de fabrication et leur utilisation en tant que medicament |
| FR2576899A1 (fr) * | 1985-02-04 | 1986-08-08 | Pf Medicament | N-carboxyalcoyl-2 oxo-3 diaryl 5-6 triazines utiles en therapeutique |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2368278A1 (fr) * | 1976-10-25 | 1978-05-19 | Fabre Sa Pierre | Nouveaux medicaments antalgiques contenant des triazines 1-2-4 |
| FR2383176A1 (fr) * | 1977-03-09 | 1978-10-06 | Fabre Sa Pierre | Amino aryl triazines 1-2-4 utilisables dans le traitement d'algies diverses |
-
1981
- 1981-03-02 FR FR8104260A patent/FR2500830A1/fr active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2368278A1 (fr) * | 1976-10-25 | 1978-05-19 | Fabre Sa Pierre | Nouveaux medicaments antalgiques contenant des triazines 1-2-4 |
| FR2383176A1 (fr) * | 1977-03-09 | 1978-10-06 | Fabre Sa Pierre | Amino aryl triazines 1-2-4 utilisables dans le traitement d'algies diverses |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/70 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2544313A1 (fr) * | 1983-04-14 | 1984-10-19 | Fabre Sa Pierre | Les n-cycloalcoyl methyl-2 oxo-3 diaryl 5-6 as triazines, leur procede de fabrication et leur utilisation en tant que medicament |
| EP0123605A1 (fr) * | 1983-04-14 | 1984-10-31 | Pierre Fabre S.A. | N-Cyclopropylméthyl-2 oxo-3 diparaméthoxyphenyl 5-6 as triazine, son procédé de fabrication et son utilisation en tant que médicament |
| US4511566A (en) * | 1983-04-14 | 1985-04-16 | Pierre Fabre S.A. | 2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines |
| FR2576899A1 (fr) * | 1985-02-04 | 1986-08-08 | Pf Medicament | N-carboxyalcoyl-2 oxo-3 diaryl 5-6 triazines utiles en therapeutique |
| EP0194164A3 (en) * | 1985-02-04 | 1987-06-16 | P.F. Medicament | N-carboxyalcoyl-2-oxo-3-diaryl-5,6-triazines useful as therapeutic agents |
| US4677105A (en) * | 1985-02-04 | 1987-06-30 | Pf Medicament | 2-alkoxycarbonylalkyl-3-oxo-5,6-diaryl-as-triazines having utility as therapeutics |
| AU568967B2 (en) * | 1985-02-04 | 1988-01-14 | P.F. Medicament ( Societe Anonyme) | 2-alkoxycarbonyl alkyl-3-oxo-5,6-diaryl-1,2,4-triazines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2500830B1 (enExample) | 1984-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |