LU81832A1 - Nouveaux derives d'acyl-1h-1,2,4-triazoles et leur procede de preparation - Google Patents
Nouveaux derives d'acyl-1h-1,2,4-triazoles et leur procede de preparation Download PDFInfo
- Publication number
- LU81832A1 LU81832A1 LU81832A LU81832A LU81832A1 LU 81832 A1 LU81832 A1 LU 81832A1 LU 81832 A LU81832 A LU 81832A LU 81832 A LU81832 A LU 81832A LU 81832 A1 LU81832 A1 LU 81832A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- group
- carbon atoms
- group containing
- alkyl
- phenyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 176
- -1 methylene-dioxy group Chemical group 0.000 claims description 142
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 35
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005336 allyloxy group Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000002254 contraceptive effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 239000003433 contraceptive agent Substances 0.000 claims 2
- DYZNMUGQXBJYEQ-UHFFFAOYSA-N 1-[5-(2-ethylphenyl)-3-(3-methoxyphenyl)-1,2,4-triazol-1-yl]ethanone Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=C(OC)C=CC=2)=NN1C(C)=O DYZNMUGQXBJYEQ-UHFFFAOYSA-N 0.000 claims 1
- YMBDJZXDDKXBKT-UHFFFAOYSA-N 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-n-(4-methylphenyl)-1,2,4-triazole-1-carboxamide Chemical compound CCC1=CC=CC=C1C1=NN(C(=O)NC=2C=CC(C)=CC=2)C(C=2C=C(OC)C=CC=2)=N1 YMBDJZXDDKXBKT-UHFFFAOYSA-N 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 229940124558 contraceptive agent Drugs 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 150000003852 triazoles Chemical class 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 210000003754 fetus Anatomy 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- GXCZZAKPGMYPDJ-UHFFFAOYSA-N 5-(2-ethylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=C(OC)C=CC=2)=NN1 GXCZZAKPGMYPDJ-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 238000002513 implantation Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000035935 pregnancy Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JWAMHAADNHBVOK-UHFFFAOYSA-N 3-(3-methoxyphenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC=CC=2)C)=C1 JWAMHAADNHBVOK-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000699800 Cricetinae Species 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 229960002903 benzyl benzoate Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- 210000004291 uterus Anatomy 0.000 description 4
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 3
- BAMLSZBEANVJGS-UHFFFAOYSA-N 5-(2-ethylphenyl)-3-(3-methoxyphenyl)-n-(4-methylphenyl)-1,2,4-triazole-1-carboxamide Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=C(OC)C=CC=2)=NN1C(=O)NC1=CC=C(C)C=C1 BAMLSZBEANVJGS-UHFFFAOYSA-N 0.000 description 3
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Chemical group CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7842417 | 1978-10-30 | ||
| GB7842417 | 1978-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU81832A1 true LU81832A1 (fr) | 1980-05-07 |
Family
ID=10500683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU81832A LU81832A1 (fr) | 1978-10-30 | 1979-10-29 | Nouveaux derives d'acyl-1h-1,2,4-triazoles et leur procede de preparation |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4459302A (is") |
| JP (1) | JPS5562075A (is") |
| KR (1) | KR830002837B1 (is") |
| AT (1) | AT368754B (is") |
| AU (1) | AU533727B2 (is") |
| BE (1) | BE879732A (is") |
| CA (1) | CA1116610A (is") |
| CH (1) | CH642953A5 (is") |
| DE (1) | DE2943326A1 (is") |
| DK (1) | DK149470C (is") |
| ES (1) | ES485492A1 (is") |
| FI (1) | FI64151C (is") |
| FR (1) | FR2440364A1 (is") |
| GB (1) | GB2039887B (is") |
| GR (1) | GR69857B (is") |
| HK (1) | HK37183A (is") |
| IE (1) | IE49626B1 (is") |
| IL (1) | IL58520A (is") |
| IT (1) | IT1196401B (is") |
| LU (1) | LU81832A1 (is") |
| NL (1) | NL7907913A (is") |
| NO (1) | NO155134C (is") |
| NZ (1) | NZ191959A (is") |
| PH (1) | PH15419A (is") |
| PT (1) | PT70387A (is") |
| SE (1) | SE445453B (is") |
| YU (1) | YU265079A (is") |
| ZA (1) | ZA795798B (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4888350A (en) * | 1978-10-30 | 1989-12-19 | Gruppo Lepetit S.P.A. | New acyl-1H-1,2,4-triazole derivatives |
| AU557034B2 (en) * | 1981-10-20 | 1986-12-04 | Gruppo Lepetit S.P.A. | 3,5-diphenyl-1h-1,2,4-trazoles with contragestational |
| IT1292092B1 (it) * | 1997-06-05 | 1999-01-25 | Geange Ltd | Impiego di derivati eterociclici aromatici azotati nel trattamento topico di affezioni di tessuti epiteliali |
| IT1292091B1 (it) * | 1997-06-05 | 1999-01-25 | Geange Ltd | Derivati eterociclici aromatici azotati,procedimento per la loro preparazione e loro impiego come antigestativi,immunosoppressori e |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308131A (en) * | 1962-12-06 | 1967-03-07 | Du Pont | Tertiary carbamyl triazoles |
| SU508198A3 (ru) * | 1971-07-22 | 1976-03-25 | Группо Лепетит С.П.А. (Фирма) | Способ получени производных 1,2,4-триазола |
| US4154841A (en) * | 1977-08-18 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Antiinflammatory 1-acyl-3(5)-alkyl-5(3)-phenyl-1,2,4-triazoles |
-
1979
- 1979-10-16 FI FI793216A patent/FI64151C/fi not_active IP Right Cessation
- 1979-10-22 GR GR60317A patent/GR69857B/el unknown
- 1979-10-22 IL IL58520A patent/IL58520A/xx unknown
- 1979-10-23 US US06/087,375 patent/US4459302A/en not_active Expired - Lifetime
- 1979-10-23 AU AU52053/79A patent/AU533727B2/en not_active Ceased
- 1979-10-26 IE IE2068/79A patent/IE49626B1/en unknown
- 1979-10-26 DE DE19792943326 patent/DE2943326A1/de active Granted
- 1979-10-26 PH PH23219A patent/PH15419A/en unknown
- 1979-10-29 NO NO793477A patent/NO155134C/no unknown
- 1979-10-29 CH CH967379A patent/CH642953A5/fr not_active IP Right Cessation
- 1979-10-29 SE SE7908940A patent/SE445453B/sv not_active IP Right Cessation
- 1979-10-29 ZA ZA00795798A patent/ZA795798B/xx unknown
- 1979-10-29 ES ES485492A patent/ES485492A1/es not_active Expired
- 1979-10-29 NL NL7907913A patent/NL7907913A/nl not_active Application Discontinuation
- 1979-10-29 JP JP13971179A patent/JPS5562075A/ja active Granted
- 1979-10-29 DK DK456779A patent/DK149470C/da not_active IP Right Cessation
- 1979-10-29 IT IT26867/79A patent/IT1196401B/it active
- 1979-10-29 PT PT70387A patent/PT70387A/pt unknown
- 1979-10-29 LU LU81832A patent/LU81832A1/fr unknown
- 1979-10-29 NZ NZ191959A patent/NZ191959A/xx unknown
- 1979-10-29 AT AT0697279A patent/AT368754B/de not_active IP Right Cessation
- 1979-10-29 GB GB7937385A patent/GB2039887B/en not_active Expired
- 1979-10-30 CA CA000338699A patent/CA1116610A/en not_active Expired
- 1979-10-30 KR KR1019790003796A patent/KR830002837B1/ko not_active Expired
- 1979-10-30 BE BE0/197897A patent/BE879732A/fr not_active IP Right Cessation
- 1979-10-30 FR FR7926903A patent/FR2440364A1/fr active Granted
- 1979-10-30 YU YU02650/79A patent/YU265079A/xx unknown
-
1983
- 1983-09-21 HK HK371/83A patent/HK37183A/xx unknown
Also Published As
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