FR2488891A1 - Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament - Google Patents
Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament Download PDFInfo
- Publication number
- FR2488891A1 FR2488891A1 FR8018354A FR8018354A FR2488891A1 FR 2488891 A1 FR2488891 A1 FR 2488891A1 FR 8018354 A FR8018354 A FR 8018354A FR 8018354 A FR8018354 A FR 8018354A FR 2488891 A1 FR2488891 A1 FR 2488891A1
- Authority
- FR
- France
- Prior art keywords
- radical
- formula
- compounds
- compound
- acids
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 229940126601 medicinal product Drugs 0.000 title abstract description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 239000002253 acid Substances 0.000 claims abstract description 38
- -1 RADICAL METHYLENE DIOXY Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 150000007513 acids Chemical class 0.000 claims abstract description 22
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims description 39
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 241001331845 Equus asinus x caballus Species 0.000 claims description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- 101150058891 alc1 gene Proteins 0.000 claims description 2
- 101150117093 alc2 gene Proteins 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 101150035983 str1 gene Proteins 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 claims 12
- 150000001768 cations Chemical class 0.000 claims 3
- 241000282320 Panthera leo Species 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 150000002367 halogens Chemical group 0.000 abstract description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 7
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 7
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- JIXYFZKFYITQCJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-phenyl-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NN=CN1C1=CC=CC=C1 JIXYFZKFYITQCJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- IBTPJHCFQPCGQI-UHFFFAOYSA-N 3-ethyl-4,5-bis(4-methoxyphenyl)-1,2,4-triazole Chemical compound C=1C=C(OC)C=CC=1N1C(CC)=NN=C1C1=CC=C(OC)C=C1 IBTPJHCFQPCGQI-UHFFFAOYSA-N 0.000 description 1
- APLVQYGMVMOAHG-UHFFFAOYSA-N 3-ethyl-4,5-bis(4-methoxyphenyl)-1,2,4-triazole;hydrochloride Chemical compound Cl.C=1C=C(OC)C=CC=1N1C(CC)=NN=C1C1=CC=C(OC)C=C1 APLVQYGMVMOAHG-UHFFFAOYSA-N 0.000 description 1
- GWUAVJDVIUWNOG-UHFFFAOYSA-N 3-ethyl-5-(4-methoxyphenyl)-4-(4-nitrophenyl)-1,2,4-triazole Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N1C(CC)=NN=C1C1=CC=C(OC)C=C1 GWUAVJDVIUWNOG-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- XXXYWQZSDNKISR-UHFFFAOYSA-N 4-methoxy-n'-(4-nitrophenyl)-n-(propanoylamino)benzenecarboximidamide Chemical compound C=1C=C(OC)C=CC=1C(=NNC(=O)CC)NC1=CC=C([N+]([O-])=O)C=C1 XXXYWQZSDNKISR-UHFFFAOYSA-N 0.000 description 1
- CQKUZIGWFLMWIR-UHFFFAOYSA-N 4-methoxy-n'-propanoylbenzohydrazide Chemical compound CCC(=O)NNC(=O)C1=CC=C(OC)C=C1 CQKUZIGWFLMWIR-UHFFFAOYSA-N 0.000 description 1
- REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- MGLHJRBKHQHAMT-UHFFFAOYSA-N n-(4-nitrophenyl)benzenecarbothioamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=S)C1=CC=CC=C1 MGLHJRBKHQHAMT-UHFFFAOYSA-N 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
- YSBTYBCMWUBKGK-UHFFFAOYSA-N n-[(4-methoxybenzoyl)amino]formamide Chemical compound COC1=CC=C(C(=O)NNC=O)C=C1 YSBTYBCMWUBKGK-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8018354A FR2488891A1 (fr) | 1980-08-22 | 1980-08-22 | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| SE8104515A SE454173B (sv) | 1980-08-22 | 1981-07-23 | 4h-1,2,4-triazolderivat till anvendning som terapeutikum, farmaceutiska kompositioner innehallande nemnda derivat, nya 4h-1,2,4-triazolderivat samt forfarande for deras framstellning |
| HU812391A HU185647B (en) | 1980-08-22 | 1981-08-17 | Process for producing new 4h-1,2,4-triazole derivatives |
| PH26054A PH19890A (en) | 1980-08-22 | 1981-08-17 | Novel 4h 1,2,4 triazole derivatives and analgesic use |
| ZA815689A ZA815689B (en) | 1980-08-22 | 1981-08-18 | Derivatives of 4h-1,2,4-triazole,their preparation,their use as medicaments,the compositions containing them and the intermediates obtained |
| PT73544A PT73544B (fr) | 1980-08-22 | 1981-08-20 | Procede de preparation de nouveaux derives du 4h-1,2,4-triazole |
| GR65834A GR75329B (en17) | 1980-08-22 | 1981-08-20 | |
| DE19813133185 DE3133185A1 (de) | 1980-08-22 | 1981-08-21 | "4h-1,2,4-triazolderivate, verfahren zu deren herstellung und deren verwendung" |
| IE1923/81A IE51510B1 (en) | 1980-08-22 | 1981-08-21 | 4h-1,2,4-triazole derivatives |
| NL8103903A NL8103903A (nl) | 1980-08-22 | 1981-08-21 | Nieuwe derivaten van 4h-1,2,4-triazool, het bereiden van deze derivaten en hun toepassing als geneesmiddel, farmaceutische preparaten die ze bevatten en de verkregen tussenprodukten. |
| JP56130408A JPS5770875A (en) | 1980-08-22 | 1981-08-21 | Novel derivatives of 4h-1,2,4-triazole, manufacture, use as drug, composition containing them and intermediate product |
| AU74426/81A AU543946B2 (en) | 1980-08-22 | 1981-08-21 | Derivatives of 4h-1,2,4-triazole |
| BE0/205731A BE890035A (fr) | 1980-08-22 | 1981-08-21 | Nouveaux derives du 4h-1,2,4-triazole, leur preparation, leur application comme medicament, les compositions les renfermant et les intermediaires obtenus |
| CH5409/81A CH649994A5 (fr) | 1980-08-22 | 1981-08-21 | Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant. |
| FI812585A FI72971C (fi) | 1980-08-22 | 1981-08-21 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4h-1,2,4-triazolderivat. |
| IT49147/81A IT1171477B (it) | 1980-08-22 | 1981-08-21 | Derivati del 4h-1,2,4-triazolo procedimento per la loro preparazione, loro impiego in quanto farmaci, composizioni che li contengono e prodotti intermedi ottenuti |
| LU83576A LU83576A1 (fr) | 1980-08-22 | 1981-08-21 | Nouveaux derives du 4h-1,2,4-triazole,leur preparation,leur application comme medicament,les compositions les renfermant et les intermediaires obtenus |
| CA000384388A CA1208226A (fr) | 1980-08-22 | 1981-08-21 | Procede de preparation de nouveaux derives du 4h-1,2, 4-triazole |
| GB8125631A GB2082581B (en) | 1980-08-22 | 1981-08-21 | 4h-1,2,4-triazole derivatives |
| DK370781A DK370781A (da) | 1980-08-22 | 1981-08-21 | Fremgangsmaade til fremstilling af 3,4-bis-phenyl-1,2,4-triazoler |
| ES504887A ES504887A0 (es) | 1980-08-22 | 1981-08-21 | Un procedimiento de preparacion de nuevos derivados de 4h-1,2,4-triazol |
| OA57482A OA06889A (fr) | 1980-08-22 | 1981-08-22 | Nouveaux dérivés du 4H-1,2,4-triazole, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires obtenus. |
| AT0368281A AT378957B (de) | 1980-08-22 | 1981-08-24 | Verfahren zur herstellung von neuen triazolderivaten |
| FR8116439A FR2512022A2 (fr) | 1980-08-22 | 1981-08-28 | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| ES515419A ES8307227A1 (es) | 1980-08-22 | 1982-09-01 | Un procedimiento de preparacion de nuevos derivados de 4h-1,2,4-triazol. |
| OA58106A OA07537A (fr) | 1980-08-22 | 1983-09-22 | Nouveaux dérivés du 4 H-1,2,4-triazole, leur préparation, leur application comme médicamment, les compositions les renfermant et les intermediaires obtenus. |
| US06/552,747 US4512997A (en) | 1980-08-22 | 1983-11-17 | 4,5-Bis(aryl)-4H-1,2,4-triazole derivatives and analgesic use |
| US06/582,051 US4659729A (en) | 1980-08-22 | 1984-02-21 | Novel 4H-1,2,4-triazole derivatives |
| PH31425A PH21567A (en) | 1980-08-22 | 1984-11-08 | Novel 4h-1,2,4 triazole derivatives |
| US06/896,858 US4727084A (en) | 1980-08-22 | 1986-08-14 | Novel 4H-1,2,4-triazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8018354A FR2488891A1 (fr) | 1980-08-22 | 1980-08-22 | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2488891A1 true FR2488891A1 (fr) | 1982-02-26 |
| FR2488891B1 FR2488891B1 (en17) | 1983-06-17 |
Family
ID=9245357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018354A Granted FR2488891A1 (fr) | 1980-08-22 | 1980-08-22 | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US4512997A (en17) |
| JP (1) | JPS5770875A (en17) |
| AT (1) | AT378957B (en17) |
| AU (1) | AU543946B2 (en17) |
| BE (1) | BE890035A (en17) |
| CA (1) | CA1208226A (en17) |
| CH (1) | CH649994A5 (en17) |
| DE (1) | DE3133185A1 (en17) |
| DK (1) | DK370781A (en17) |
| ES (2) | ES504887A0 (en17) |
| FI (1) | FI72971C (en17) |
| FR (1) | FR2488891A1 (en17) |
| GB (1) | GB2082581B (en17) |
| GR (1) | GR75329B (en17) |
| HU (1) | HU185647B (en17) |
| IE (1) | IE51510B1 (en17) |
| IT (1) | IT1171477B (en17) |
| LU (1) | LU83576A1 (en17) |
| NL (1) | NL8103903A (en17) |
| OA (2) | OA06889A (en17) |
| PH (2) | PH19890A (en17) |
| PT (1) | PT73544B (en17) |
| SE (1) | SE454173B (en17) |
| ZA (1) | ZA815689B (en17) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2488891A1 (fr) * | 1980-08-22 | 1982-02-26 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| FR2539127B1 (fr) * | 1983-01-10 | 1985-08-23 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicaments |
| FR2570699B1 (fr) * | 1984-09-24 | 1987-08-28 | Roussel Uclaf | Nouveau procede de preparation de derives du 4h-1,2,4-triazole, nouveaux triazoles ainsi obtenus, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| US5278180A (en) * | 1984-09-24 | 1994-01-11 | Roussel Uclaf | 4,5-bis(aryl) 4H-1,2,4-triazoles derivatives and analgesic use |
| RU2124010C1 (ru) * | 1991-09-02 | 1998-12-27 | Яманучи Фармасетикал Ко., Лтд. | Триазолилзамещенное соединение третичного амина и фармацевтическая композиция |
| US5922751A (en) * | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| RU2131411C1 (ru) * | 1997-11-20 | 1999-06-10 | Институт химической физики РАН в Черноголовке | Способ получения смеси олиготрифениламинов, способ получения 3-(4-бифенилил)-4- (4-трет-бутилфенил)-5-(4-диметиламинофенил)-1,2,4-триазола и электролюминесцентное устройство |
| US6362342B1 (en) * | 1999-06-29 | 2002-03-26 | Lion Bioscience Ag | Triazole compounds and methods of making same |
| US6770621B2 (en) | 2000-05-02 | 2004-08-03 | Theravance, Inc. | Polyacid glycopeptide derivatives |
| AU2003210916B9 (en) * | 2002-02-07 | 2008-12-18 | The Curators Of The University Of Missouri | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
| KR102780240B1 (ko) | 2017-04-26 | 2025-03-14 | 오티아이 루미오닉스 인크. | 표면의 코팅을 패턴화하는 방법 및 패턴화된 코팅을 포함하는 장치 |
| US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| US11730012B2 (en) | 2019-03-07 | 2023-08-15 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| US12101987B2 (en) | 2019-04-18 | 2024-09-24 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| JP7576337B2 (ja) | 2019-05-08 | 2024-11-01 | オーティーアイ ルミオニクス インコーポレーテッド | 核生成抑制コーティングを形成するための材料およびそれを組み込んだデバイス |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1796403A (en) * | 1931-03-17 | Schaft | ||
| US3681374A (en) * | 1970-08-11 | 1972-08-01 | Asahi Chemical Ind | Synthetic nacreous triazole crystals and method for production thereof |
| SU508198A3 (ru) * | 1971-07-22 | 1976-03-25 | Группо Лепетит С.П.А. (Фирма) | Способ получени производных 1,2,4-триазола |
| AU7528974A (en) * | 1973-11-13 | 1976-06-10 | Commonwealth Scientific And Industrial Research Organization | Triazoles |
| FR2269938A2 (en) * | 1974-05-08 | 1975-12-05 | Delalande Sa | 5-Hydroxymethyl-3,4-diphenyl-1,2,4-triazoles - with anticholinergic, bronchodilator, antidepressant, analgesic, vasodilator activity, etc. |
| JPS56125376A (en) * | 1980-03-07 | 1981-10-01 | Mitsubishi Chem Ind Ltd | Triazole derivative |
| FR2488891A1 (fr) * | 1980-08-22 | 1982-02-26 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
-
1980
- 1980-08-22 FR FR8018354A patent/FR2488891A1/fr active Granted
-
1981
- 1981-07-23 SE SE8104515A patent/SE454173B/sv not_active IP Right Cessation
- 1981-08-17 PH PH26054A patent/PH19890A/en unknown
- 1981-08-17 HU HU812391A patent/HU185647B/hu not_active IP Right Cessation
- 1981-08-18 ZA ZA815689A patent/ZA815689B/xx unknown
- 1981-08-20 GR GR65834A patent/GR75329B/el unknown
- 1981-08-20 PT PT73544A patent/PT73544B/pt unknown
- 1981-08-21 BE BE0/205731A patent/BE890035A/fr not_active IP Right Cessation
- 1981-08-21 LU LU83576A patent/LU83576A1/fr unknown
- 1981-08-21 IE IE1923/81A patent/IE51510B1/en unknown
- 1981-08-21 NL NL8103903A patent/NL8103903A/nl not_active Application Discontinuation
- 1981-08-21 JP JP56130408A patent/JPS5770875A/ja active Granted
- 1981-08-21 AU AU74426/81A patent/AU543946B2/en not_active Ceased
- 1981-08-21 GB GB8125631A patent/GB2082581B/en not_active Expired
- 1981-08-21 ES ES504887A patent/ES504887A0/es active Granted
- 1981-08-21 DE DE19813133185 patent/DE3133185A1/de not_active Ceased
- 1981-08-21 CA CA000384388A patent/CA1208226A/fr not_active Expired
- 1981-08-21 CH CH5409/81A patent/CH649994A5/fr not_active IP Right Cessation
- 1981-08-21 DK DK370781A patent/DK370781A/da not_active Application Discontinuation
- 1981-08-21 FI FI812585A patent/FI72971C/fi not_active IP Right Cessation
- 1981-08-21 IT IT49147/81A patent/IT1171477B/it active
- 1981-08-22 OA OA57482A patent/OA06889A/xx unknown
- 1981-08-24 AT AT0368281A patent/AT378957B/de not_active IP Right Cessation
-
1982
- 1982-09-01 ES ES515419A patent/ES8307227A1/es not_active Expired
-
1983
- 1983-09-22 OA OA58106A patent/OA07537A/xx unknown
- 1983-11-17 US US06/552,747 patent/US4512997A/en not_active Expired - Fee Related
-
1984
- 1984-02-21 US US06/582,051 patent/US4659729A/en not_active Expired - Fee Related
- 1984-11-08 PH PH31425A patent/PH21567A/en unknown
-
1986
- 1986-08-14 US US06/896,858 patent/US4727084A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| CA1970 * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2488891A1 (fr) | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament | |
| EP0012639B1 (fr) | Nouveaux dérivés de l'acide 3-quinoléine carboxylique, leur procédé de préparation, leur application comme médicament et les compositions pharmaceutiques les renfermant | |
| EP0227539B1 (fr) | Nouvelles 4H-triazolo /4,3-a/ /1,4/ benzodiazépines, leur procédé de préparation leur application comme médicaments et les compositions les renfermant | |
| CH628344A5 (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. | |
| EP0112191A1 (fr) | Nouveaux dérivés du 4-(1H-indol-3-yl) alpha-méthylpipéridine 1-éthanol, leurs sels, le procédé de préparation, l'application à titre de médicaments et les compositions les renfermant | |
| EP0040573B1 (fr) | Dérivés de l'acide 4-hydroxy 3-quinoléine carboxylique substitués en 2, leur préparation, leur application comme médicament, les compositions les renfermant et les intermédiaires nouveaux obtenus | |
| CA1204116A (fr) | Procede de preparation de nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 | |
| CH675245A5 (en17) | ||
| CA1100968A (fr) | Procedes de preparation de nouvelles piperazines disubstituees | |
| EP0214004B1 (fr) | Dérivés de l'acide 4-OH quinoléine carboxylique substitué en 2 par un groupement dihydroxylé éventuellement éthérifié ou estérifié, procédé et inter-médiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| CA1082716A (fr) | Procede de preparation de nouveaux derives de 5- thiazole methane amine | |
| CA1256113A (fr) | Procede de preparation de derives du 4h-1,2,4- triazole | |
| FR2641534A1 (fr) | Nouveaux derives de glycine utiles comme medicaments antagonistes du thromboxane a2 et procede pour leur preparation | |
| CA1105022A (fr) | Procede de preparation de nouveaux derives de la benzophenone | |
| FR2636327A1 (fr) | Derives de quinoleine, leurs procedes de preparation et les medicaments les contenant | |
| FR2539127A1 (fr) | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicaments | |
| CA1093077A (fr) | Procede de preparation de nouvelles quinoleines substituees | |
| CH636350A5 (fr) | Derives de l'acide 2-/(4-quinoleinyl) amino/ 5-fluorobenzoique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant. | |
| FR2617478A1 (fr) | Nouveaux derives d'aryl-heteroaryl cetones, leur procede de preparation ainsi que leur application a titre de medicament | |
| FR2572404A2 (fr) | Nouveaux derives de l'acide 4-oh-3-quinoleine carboxylique substitues en 2, leur procede de preparation, leur application comme medicaments et les compositions les renfermant | |
| FR2512022A2 (fr) | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament | |
| FR2611712A1 (fr) | Nouveaux derives n-substitues de l'alpha-mercaptomethyl benzene propanamide, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant | |
| FR2636329A2 (fr) | Nouveaux derives de la pyridine, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant | |
| FR2558467A2 (fr) | Nouveau produit derive de l'acide 3-amino 2-oxo azetidine 1-sulfamique, son procede de preparation, son application comme medicament et un produit intermediaire necessaire a sa preparation | |
| FR2532314A1 (fr) | Nouveau procede de preparation de derives de l'acide 3-quinoleine carboxylique, nouveaux derives halogenes de l'acide 3-quinoleine carboxylique, leur application comme medicaments, les compositions pharmaceutiques les renfermant et les intermediaires nouveaux obtenus |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |