CA1130296A - Hydroxypropyl-triazole compounds, their production and their medicinal use - Google Patents
Hydroxypropyl-triazole compounds, their production and their medicinal useInfo
- Publication number
- CA1130296A CA1130296A CA340,546A CA340546A CA1130296A CA 1130296 A CA1130296 A CA 1130296A CA 340546 A CA340546 A CA 340546A CA 1130296 A CA1130296 A CA 1130296A
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- triazol
- propan
- radical
- phenyl
- 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
- ICGHHKXZWABEBX-UHFFFAOYSA-N 3-(2h-triazol-4-yl)propan-1-ol Chemical class OCCCC1=CNN=N1 ICGHHKXZWABEBX-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 49
- -1 triazole radical Chemical class 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 21
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- QEVQDUARWQPGIH-UHFFFAOYSA-N 1-chloro-3-(2,4-dichlorophenyl)-2-(4-phenylphenyl)propan-2-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CCl)(O)CC1=CC=C(Cl)C=C1Cl QEVQDUARWQPGIH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- MUGXHBORJBOPIB-UHFFFAOYSA-N 1-chloro-3-phenyl-2-(4-phenylphenyl)propan-2-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CCl)(O)CC1=CC=CC=C1 MUGXHBORJBOPIB-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 claims 3
- DGWHDIYEULVUTH-UHFFFAOYSA-N 1-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound CC(O)CN1C=NC=N1 DGWHDIYEULVUTH-UHFFFAOYSA-N 0.000 claims 1
- XKSIZEKYPGPNCI-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-phenylphenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C1=NC=NN1CC(C=1C=CC(=CC=1)C=1C=CC=CC=1)(O)CC1=CC=C(Cl)C=C1 XKSIZEKYPGPNCI-UHFFFAOYSA-N 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- XUPANCKBBOYIKC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=C=CC=C[CH]1 XUPANCKBBOYIKC-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 13
- HPRNDOZJRIKYCR-UHFFFAOYSA-N 4-propyl-1,2-dihydrotriazol-5-one Chemical class CCCC=1N=NNC=1O HPRNDOZJRIKYCR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003429 antifungal agent Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000003814 drug Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- CAGSFWGURSSRMS-UHFFFAOYSA-N 1,3-bis(1,2,4-triazol-4-yl)propan-2-one Chemical compound C1=NN=CN1CC(=O)CN1C=NN=C1 CAGSFWGURSSRMS-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 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 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000001857 anti-mycotic effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000001427 coherent effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001480043 Arthrodermataceae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension 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
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IQEIGQFNDLINOT-UHFFFAOYSA-N 2-chloro-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CCl)=CC=C1C1=CC=CC=C1 IQEIGQFNDLINOT-UHFFFAOYSA-N 0.000 description 2
- QKMSCHYQWAVTRZ-UHFFFAOYSA-N 3-(1h-pyrrol-2-yl)propan-1-ol Chemical class OCCCC1=CC=CN1 QKMSCHYQWAVTRZ-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- 239000000443 aerosol Substances 0.000 description 2
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- 150000003973 alkyl amines Chemical group 0.000 description 2
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- WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 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
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- PHSLYQFWLCWIBU-UHFFFAOYSA-M magnesium;1-chloro-2-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1Cl PHSLYQFWLCWIBU-UHFFFAOYSA-M 0.000 description 1
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- BQNQIHYLDYHYQP-UHFFFAOYSA-M magnesium;1-chloro-3-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC(Cl)=C1 BQNQIHYLDYHYQP-UHFFFAOYSA-M 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- NVMNEWNGLGACBB-UHFFFAOYSA-N sodium;1,2-diaza-4-azanidacyclopenta-2,5-diene Chemical compound [Na+].C=1N=C[N-]N=1 NVMNEWNGLGACBB-UHFFFAOYSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2851086.3 | 1978-11-25 | ||
| DE19782851086 DE2851086A1 (de) | 1978-11-25 | 1978-11-25 | Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1130296A true CA1130296A (en) | 1982-08-24 |
Family
ID=6055560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA340,546A Expired CA1130296A (en) | 1978-11-25 | 1979-11-23 | Hydroxypropyl-triazole compounds, their production and their medicinal use |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4381306A (en, 2012) |
| EP (1) | EP0011768B1 (en, 2012) |
| JP (1) | JPS55108860A (en, 2012) |
| AT (1) | ATE324T1 (en, 2012) |
| AU (1) | AU536920B2 (en, 2012) |
| CA (1) | CA1130296A (en, 2012) |
| DD (1) | DD146824A5 (en, 2012) |
| DE (2) | DE2851086A1 (en, 2012) |
| DK (1) | DK152493C (en, 2012) |
| ES (1) | ES486279A1 (en, 2012) |
| FI (1) | FI65992C (en, 2012) |
| HU (1) | HU179414B (en, 2012) |
| IE (1) | IE48880B1 (en, 2012) |
| IL (1) | IL58782A (en, 2012) |
| NO (1) | NO793673L (en, 2012) |
| NZ (1) | NZ192195A (en, 2012) |
| PH (1) | PH16119A (en, 2012) |
| ZA (1) | ZA796356B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4927839A (en) * | 1979-03-07 | 1990-05-22 | Imperial Chemical Industries Plc | Method of preventing fungal attack on wood, hides, leather or paint films using a triazole |
| US4551469A (en) * | 1979-03-07 | 1985-11-05 | Imperial Chemical Industries Plc | Antifungal triazole ethanol derivatives |
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| DE3018865A1 (de) * | 1980-05-16 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Antimikrobielle mittel |
| AU542623B2 (en) * | 1980-05-16 | 1985-02-28 | Bayer Aktiengesellschaft | 1-hydroxyethyl-azole derivatives |
| DE3177292T2 (de) * | 1980-08-18 | 1993-03-11 | Ici Plc | Triazol-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als fungizide und pflanzenwachstumsregulatoren. |
| EP0046337A3 (en) * | 1980-08-20 | 1982-09-15 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them |
| EP0048548B1 (en) * | 1980-08-28 | 1984-11-14 | Imperial Chemical Industries Plc | Pharmaceutical compositions of fungicidal triazole derivatives |
| AT375359B (de) * | 1980-09-02 | 1984-07-25 | Ici Plc | Verfahren zur herstellung von neuen verbindungen |
| AU8314482A (en) * | 1981-05-19 | 1982-11-25 | Imperial Chemical Industries Plc | 3-triazolyl(imidazolyl)-2,2 bis phenyl-propionamides |
| DE3232647A1 (de) * | 1982-09-02 | 1984-03-08 | Bayer Ag, 5090 Leverkusen | Substituierte tert.-butanol-derivate, verfahren zu ihrer herstellung und diese enthaltende antimykotische mittel |
| DE3245504A1 (de) * | 1982-12-09 | 1984-06-14 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, deren herstellung und verwendung |
| EP0117100B1 (en) * | 1983-02-16 | 1986-12-10 | Pfizer Limited | Triazole antifungal agents |
| EP0315861B1 (de) * | 1987-11-09 | 1992-01-29 | Bayer Ag | Antimycotische Zusammensetzungen aus Nikkomycin-Verbindungen und antimycotischem Azol |
| US5006513A (en) * | 1987-11-09 | 1991-04-09 | Miles Inc. | Antimycotic compositions of nikkomycin compounds and azole antimycotica |
| US5096889A (en) * | 1987-11-09 | 1992-03-17 | Bayer Ag | Antimycotic compositions of nikkomycin compounds and azole antimycotics |
| US5194427A (en) * | 1987-11-09 | 1993-03-16 | Bayer Ag | Antimycotic compositions of nikkomycin compounds and azole antimycotics |
| EP0321211A1 (en) * | 1987-12-17 | 1989-06-21 | E.I. Du Pont De Nemours And Company | Antifungal carbinols |
| US4914087A (en) * | 1988-02-29 | 1990-04-03 | Bayer Ag | Nikkomycin derivatives, antimycotic compositions of nikkomycin derivatives and azole antimycotics |
| US5098920A (en) * | 1990-05-04 | 1992-03-24 | G. D. Searle & Co. | 1h-substituted-1,2,4-triazole compounds and methods of use thereof for treatment of cardiovascular disorders |
| US5155117A (en) * | 1991-04-12 | 1992-10-13 | G. D. Searle & Co. | 1-arylheteroarylalkyl substituted-1h-1,2,4-triazole compounds for treatment of circulatory disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002763A (en) * | 1972-09-26 | 1977-01-11 | Bayer Aktiengesellschaft | 1,2,4-Triazole antimycotic compositions and use thereof |
| DE2324424A1 (de) * | 1973-05-15 | 1974-12-05 | Bayer Ag | Antimikrobielle mittel |
| DE2431407C2 (de) * | 1974-06-29 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | 1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| GB1569267A (en) * | 1975-12-16 | 1980-06-11 | Ici Ltd | Substituted propiophenones and herbicidal and fungicidal compositions containing them |
| DE2623129C3 (de) * | 1976-05-22 | 1980-04-10 | Nordmark-Werke Gmbh, 2000 Hamburg | U-Diphenyl-3-(imidazol-l-yl) -propan-2-ole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE2705679A1 (de) * | 1977-02-11 | 1978-08-17 | Bayer Ag | Antimikrobielle mittel |
-
1978
- 1978-11-25 DE DE19782851086 patent/DE2851086A1/de not_active Withdrawn
-
1979
- 1979-11-09 US US06/092,805 patent/US4381306A/en not_active Expired - Lifetime
- 1979-11-13 NO NO793673A patent/NO793673L/no unknown
- 1979-11-14 EP EP79104483A patent/EP0011768B1/de not_active Expired
- 1979-11-14 AT AT79104483T patent/ATE324T1/de not_active IP Right Cessation
- 1979-11-14 DE DE7979104483T patent/DE2961083D1/de not_active Expired
- 1979-11-20 DD DD79217019A patent/DD146824A5/de unknown
- 1979-11-22 JP JP15080079A patent/JPS55108860A/ja active Granted
- 1979-11-22 IL IL58782A patent/IL58782A/xx unknown
- 1979-11-22 NZ NZ192195A patent/NZ192195A/xx unknown
- 1979-11-23 ES ES486279A patent/ES486279A1/es not_active Expired
- 1979-11-23 HU HU79BA3891A patent/HU179414B/hu not_active IP Right Cessation
- 1979-11-23 PH PH23326A patent/PH16119A/en unknown
- 1979-11-23 IE IE2241/79A patent/IE48880B1/en unknown
- 1979-11-23 DK DK499679A patent/DK152493C/da not_active IP Right Cessation
- 1979-11-23 FI FI793688A patent/FI65992C/fi not_active IP Right Cessation
- 1979-11-23 CA CA340,546A patent/CA1130296A/en not_active Expired
- 1979-11-23 ZA ZA00796356A patent/ZA796356B/xx unknown
- 1979-11-26 AU AU53172/79A patent/AU536920B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE2851086A1 (de) | 1980-06-04 |
| JPS55108860A (en) | 1980-08-21 |
| IL58782A0 (en) | 1980-02-29 |
| FI65992B (fi) | 1984-04-30 |
| EP0011768A1 (de) | 1980-06-11 |
| US4381306A (en) | 1983-04-26 |
| PH16119A (en) | 1983-06-30 |
| DK152493C (da) | 1988-07-25 |
| DK499679A (da) | 1980-05-26 |
| EP0011768B1 (de) | 1981-10-21 |
| JPS6258355B2 (en, 2012) | 1987-12-05 |
| ES486279A1 (es) | 1980-05-16 |
| FI793688A7 (fi) | 1980-05-26 |
| HU179414B (en) | 1982-10-28 |
| IE48880B1 (en) | 1985-06-12 |
| FI65992C (fi) | 1984-08-10 |
| AU5317279A (en) | 1980-05-29 |
| AU536920B2 (en) | 1984-05-31 |
| DE2961083D1 (en) | 1981-12-24 |
| DK152493B (da) | 1988-03-07 |
| ATE324T1 (de) | 1981-11-15 |
| NZ192195A (en) | 1981-10-19 |
| NO793673L (no) | 1980-05-28 |
| ZA796356B (en) | 1980-12-31 |
| IE792241L (en) | 1980-05-25 |
| DD146824A5 (de) | 1981-03-04 |
| IL58782A (en) | 1984-02-29 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |