DE2819372C2 - - Google Patents
Info
- Publication number
- DE2819372C2 DE2819372C2 DE2819372A DE2819372A DE2819372C2 DE 2819372 C2 DE2819372 C2 DE 2819372C2 DE 2819372 A DE2819372 A DE 2819372A DE 2819372 A DE2819372 A DE 2819372A DE 2819372 C2 DE2819372 C2 DE 2819372C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- triazole
- compounds
- compound
- mol
- 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
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 methylenedioxy group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 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 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 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 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims description 3
- RTUMUTCJTDAUBX-UHFFFAOYSA-N 3-(3-ethoxyphenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound CCOC1=CC=CC(C=2N=C(NN=2)C=2C(=CC=CC=2)C)=C1 RTUMUTCJTDAUBX-UHFFFAOYSA-N 0.000 claims description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical class Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical class C(N)(=N)* 0.000 claims 1
- 125000004093 cyano group Chemical class *C#N 0.000 claims 1
- 150000002465 imidoyl halides Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002905 orthoesters Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 11
- 230000035935 pregnancy Effects 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 210000003754 fetus Anatomy 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 6
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002513 implantation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008159 sesame oil Substances 0.000 description 4
- 235000011803 sesame oil Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- BANZVKGLDQDFDV-UHFFFAOYSA-N 2-propan-2-ylbenzoic acid Chemical compound CC(C)C1=CC=CC=C1C(O)=O BANZVKGLDQDFDV-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000016087 ovulation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 241000282520 Papio Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XHYSKFPWUYZGCV-UHFFFAOYSA-N ethyl 4-chlorobenzenecarboximidate Chemical compound CCOC(=N)C1=CC=C(Cl)C=C1 XHYSKFPWUYZGCV-UHFFFAOYSA-N 0.000 description 2
- 230000004720 fertilization Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003054 hormonal effect Effects 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 210000001215 vagina Anatomy 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- JCUSTVVFOVQQLS-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC=C1C1=NNC(C=2C(=CC=CC=2)C)=N1 JCUSTVVFOVQQLS-UHFFFAOYSA-N 0.000 description 1
- AVLDHPNHSUKPDX-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=C(Cl)C=CC=2)=NN1 AVLDHPNHSUKPDX-UHFFFAOYSA-N 0.000 description 1
- IZKOJNOSZADANF-UHFFFAOYSA-N 3-(3-methoxyphenyl)-5-(2-propan-2-ylphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC=CC=2)C(C)C)=C1 IZKOJNOSZADANF-UHFFFAOYSA-N 0.000 description 1
- VWBJOECUNNJENN-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-ethylphenyl)-1h-1,2,4-triazole Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=NN1 VWBJOECUNNJENN-UHFFFAOYSA-N 0.000 description 1
- AOBQVORYICVDOJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)=NN1 AOBQVORYICVDOJ-UHFFFAOYSA-N 0.000 description 1
- YFPAVAXUTBXIAH-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-(2-methylphenyl)-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=CC(F)=CC=2)=NN1 YFPAVAXUTBXIAH-UHFFFAOYSA-N 0.000 description 1
- UZYSRLVDUAGZEI-UHFFFAOYSA-N 3-phenyl-5-(2-propan-2-ylphenyl)-1h-1,2,4-triazole Chemical compound CC(C)C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 UZYSRLVDUAGZEI-UHFFFAOYSA-N 0.000 description 1
- LXVXIEDVPDPIGJ-UHFFFAOYSA-N 5-(2,4-dimethylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 LXVXIEDVPDPIGJ-UHFFFAOYSA-N 0.000 description 1
- DDZKDENUAPJIGC-UHFFFAOYSA-N 5-(2,5-dimethylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC=C(C)C=2)C)=C1 DDZKDENUAPJIGC-UHFFFAOYSA-N 0.000 description 1
- ARXYGSGAEPXPFF-UHFFFAOYSA-N 5-(2,5-dimethylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC=C(C)C(C=2NN=C(N=2)C=2C=CC=CC=2)=C1 ARXYGSGAEPXPFF-UHFFFAOYSA-N 0.000 description 1
- XBYGUXKVAJQXEO-UHFFFAOYSA-N 5-(2-butylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound CCCCC1=CC=CC=C1C1=NC(C=2C=C(OC)C=CC=2)=NN1 XBYGUXKVAJQXEO-UHFFFAOYSA-N 0.000 description 1
- NEEHHGCSOUSERQ-UHFFFAOYSA-N 5-(2-butylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CCCCC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 NEEHHGCSOUSERQ-UHFFFAOYSA-N 0.000 description 1
- ANIGOOQXMDHYSN-UHFFFAOYSA-N 5-(2-ethylphenyl)-3-(3-fluorophenyl)-1h-1,2,4-triazole Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=C(F)C=CC=2)=NN1 ANIGOOQXMDHYSN-UHFFFAOYSA-N 0.000 description 1
- BQKLBSZNFCZZQE-UHFFFAOYSA-N 5-(2-ethylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CCC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 BQKLBSZNFCZZQE-UHFFFAOYSA-N 0.000 description 1
- NEAMVTMFSSBVQY-UHFFFAOYSA-N 5-(2-methylphenyl)-3-(4-phenylphenyl)-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NN1 NEAMVTMFSSBVQY-UHFFFAOYSA-N 0.000 description 1
- DYGMEXLJCFIJME-UHFFFAOYSA-N 5-(2-methylphenyl)-3-[3-(trifluoromethyl)phenyl]-1h-1,2,4-triazole Chemical compound CC1=CC=CC=C1C1=NC(C=2C=C(C=CC=2)C(F)(F)F)=NN1 DYGMEXLJCFIJME-UHFFFAOYSA-N 0.000 description 1
- JQVCKQSNWIUGRF-UHFFFAOYSA-N 5-(4-chloro-2-methylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC(Cl)=CC=2)C)=C1 JQVCKQSNWIUGRF-UHFFFAOYSA-N 0.000 description 1
- LGVUPKLKXKOWAC-UHFFFAOYSA-N 5-(4-chloro-2-methylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 LGVUPKLKXKOWAC-UHFFFAOYSA-N 0.000 description 1
- KBSQCMLMRNIQOF-UHFFFAOYSA-N 5-(4-methoxy-2-methylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC(OC)=CC=2)C)=C1 KBSQCMLMRNIQOF-UHFFFAOYSA-N 0.000 description 1
- ZHGGSRLTWAJZIQ-UHFFFAOYSA-N 5-(4-methoxy-2-methylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=NN1 ZHGGSRLTWAJZIQ-UHFFFAOYSA-N 0.000 description 1
- NLHQVGDLVPMMNP-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-3-(3-methoxyphenyl)-1h-1,2,4-triazole Chemical compound COC1=CC=CC(C=2N=C(NN=2)C=2C(=CC=C(Cl)C=2)C)=C1 NLHQVGDLVPMMNP-UHFFFAOYSA-N 0.000 description 1
- GYURHAXCPUVCIO-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-3-phenyl-1h-1,2,4-triazole Chemical compound CC1=CC=C(Cl)C=C1C1=NC(C=2C=CC=CC=2)=NN1 GYURHAXCPUVCIO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 240000009122 Satureja thymbra Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YDXVOCXVQXQYPX-UHFFFAOYSA-N ethyl 2-chlorobenzenecarboximidate Chemical compound CCOC(=N)C1=CC=CC=C1Cl YDXVOCXVQXQYPX-UHFFFAOYSA-N 0.000 description 1
- JQBFOYUAGSKFCY-UHFFFAOYSA-N ethyl 2-methoxybenzenecarboximidate Chemical compound CCOC(=N)C1=CC=CC=C1OC JQBFOYUAGSKFCY-UHFFFAOYSA-N 0.000 description 1
- JFKWKYOWMWTTHJ-UHFFFAOYSA-N ethyl 4-fluorobenzenecarboximidate Chemical compound CCOC(=N)C1=CC=C(F)C=C1 JFKWKYOWMWTTHJ-UHFFFAOYSA-N 0.000 description 1
- CQBWPUJYGMSGDU-UHFFFAOYSA-N ethyl benzenecarboximidate Chemical class CCOC(=N)C1=CC=CC=C1 CQBWPUJYGMSGDU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004973 motor coordination Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000008925 spontaneous activity Effects 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
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 150000003852 triazoles Chemical class 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
- 238000005303 weighing 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19012/77A GB1579352A (en) | 1977-05-06 | 1977-05-06 | 3,5-disubstituted-1h-1,2,4-triazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2819372A1 DE2819372A1 (de) | 1978-11-16 |
| DE2819372C2 true DE2819372C2 (enEXAMPLES) | 1988-02-25 |
Family
ID=10122292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782819372 Granted DE2819372A1 (de) | 1977-05-06 | 1978-05-03 | 3,5-disubstituierte 1h-1,2,4-triazole und verfahren zu ihrer herstellung |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS53137965A (enEXAMPLES) |
| AT (1) | AT360530B (enEXAMPLES) |
| AU (1) | AU520348B2 (enEXAMPLES) |
| BE (1) | BE866728A (enEXAMPLES) |
| CA (1) | CA1100511A (enEXAMPLES) |
| CH (1) | CH630909A5 (enEXAMPLES) |
| DE (1) | DE2819372A1 (enEXAMPLES) |
| DK (1) | DK149469C (enEXAMPLES) |
| ES (1) | ES469482A1 (enEXAMPLES) |
| FI (1) | FI64150C (enEXAMPLES) |
| FR (1) | FR2389615B1 (enEXAMPLES) |
| GB (1) | GB1579352A (enEXAMPLES) |
| GR (1) | GR66126B (enEXAMPLES) |
| HK (1) | HK26281A (enEXAMPLES) |
| IE (1) | IE46821B1 (enEXAMPLES) |
| IL (1) | IL54517A (enEXAMPLES) |
| IT (1) | IT1158700B (enEXAMPLES) |
| LU (1) | LU79601A1 (enEXAMPLES) |
| NL (1) | NL7804211A (enEXAMPLES) |
| NO (2) | NO148525C (enEXAMPLES) |
| NZ (1) | NZ187181A (enEXAMPLES) |
| PH (1) | PH15364A (enEXAMPLES) |
| PT (1) | PT68005B (enEXAMPLES) |
| SE (1) | SE444316B (enEXAMPLES) |
| YU (1) | YU41311B (enEXAMPLES) |
| ZA (1) | ZA782118B (enEXAMPLES) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2961326D1 (en) * | 1978-10-30 | 1982-01-14 | Lepetit Spa | New 1,2,4-triazole derivatives, a process for their manufacture and pharmaceutical compositions containing them |
| DE3173083D1 (en) * | 1980-03-22 | 1986-01-16 | Fbc Ltd | Pesticidal heterocyclic compounds, processes for preparing them, compositions containing them, and their use |
| AU557034B2 (en) * | 1981-10-20 | 1986-12-04 | Gruppo Lepetit S.P.A. | 3,5-diphenyl-1h-1,2,4-trazoles with contragestational |
| US5017386A (en) * | 1989-10-05 | 1991-05-21 | University Of Kentucky Research Foundation | Method of reducing odor associated with hexanal production in plant products |
| WO1995033732A1 (fr) * | 1994-06-09 | 1995-12-14 | Nippon Soda Co., Ltd. | Compose de triazole, procede de production et pesticide |
| IT1292092B1 (it) * | 1997-06-05 | 1999-01-25 | Geange Ltd | Impiego di derivati eterociclici aromatici azotati nel trattamento topico di affezioni di tessuti epiteliali |
| DE60007697T2 (de) * | 1999-07-21 | 2004-12-09 | F. Hoffmann-La Roche Ag | Triazolderivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU508198A3 (ru) * | 1971-07-22 | 1976-03-25 | Группо Лепетит С.П.А. (Фирма) | Способ получени производных 1,2,4-триазола |
| JPS5241264B2 (enEXAMPLES) * | 1973-05-21 | 1977-10-17 | ||
| JPS5082066A (enEXAMPLES) * | 1973-10-30 | 1975-07-03 | ||
| AU497898B2 (en) * | 1975-01-10 | 1979-01-18 | Commonwealth Scientific And Industrial Research Organisation | Plant growth regulating method and composition for use therein |
-
1977
- 1977-05-06 GB GB19012/77A patent/GB1579352A/en not_active Expired
-
1978
- 1978-04-07 GR GR55921A patent/GR66126B/el unknown
- 1978-04-12 ZA ZA00782118A patent/ZA782118B/xx unknown
- 1978-04-17 AU AU35140/78A patent/AU520348B2/en not_active Expired
- 1978-04-17 IL IL54517A patent/IL54517A/xx unknown
- 1978-04-20 NL NL7804211A patent/NL7804211A/xx not_active Application Discontinuation
- 1978-04-25 DK DK178978A patent/DK149469C/da not_active IP Right Cessation
- 1978-04-26 YU YU1036/78A patent/YU41311B/xx unknown
- 1978-04-28 FI FI781339A patent/FI64150C/fi not_active IP Right Cessation
- 1978-05-02 AT AT315678A patent/AT360530B/de not_active IP Right Cessation
- 1978-05-02 JP JP5324478A patent/JPS53137965A/ja active Granted
- 1978-05-03 CH CH483478A patent/CH630909A5/fr not_active IP Right Cessation
- 1978-05-03 NO NO781560A patent/NO148525C/no unknown
- 1978-05-03 DE DE19782819372 patent/DE2819372A1/de active Granted
- 1978-05-03 IT IT22928/78A patent/IT1158700B/it active
- 1978-05-03 FR FR7813205A patent/FR2389615B1/fr not_active Expired
- 1978-05-05 BE BE187412A patent/BE866728A/xx not_active IP Right Cessation
- 1978-05-05 IE IE918/78A patent/IE46821B1/en unknown
- 1978-05-05 SE SE7805184A patent/SE444316B/sv not_active IP Right Cessation
- 1978-05-05 LU LU79601A patent/LU79601A1/xx unknown
- 1978-05-05 CA CA302,712A patent/CA1100511A/en not_active Expired
- 1978-05-05 NZ NZ187181A patent/NZ187181A/xx unknown
- 1978-05-05 PT PT68005A patent/PT68005B/pt unknown
- 1978-05-05 ES ES469482A patent/ES469482A1/es not_active Expired
-
1979
- 1979-06-01 PH PH22600A patent/PH15364A/en unknown
-
1981
- 1981-06-18 HK HK262/81A patent/HK26281A/xx unknown
-
1982
- 1982-11-03 NO NO823654A patent/NO823654L/no unknown
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