NO136576B - - Google Patents
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- Publication number
- NO136576B NO136576B NO2482/73A NO248273A NO136576B NO 136576 B NO136576 B NO 136576B NO 2482/73 A NO2482/73 A NO 2482/73A NO 248273 A NO248273 A NO 248273A NO 136576 B NO136576 B NO 136576B
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- phenyl
- dimethylphenyl
- formula
- methyl
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- FBAOVPVVMDOHPK-UHFFFAOYSA-N 2-(1h-imidazol-2-ylsulfinyl)-1h-imidazole Chemical compound N=1C=CNC=1S(=O)C1=NC=CN1 FBAOVPVVMDOHPK-UHFFFAOYSA-N 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- -1 (dimethylphenyl-phenyl-pyridyl)-methanols Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000013543 active substance Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000223238 Trichophyton Species 0.000 description 6
- 241001480043 Arthrodermataceae Species 0.000 description 5
- 230000037304 dermatophytes Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MEAXTABTGJJRAA-UHFFFAOYSA-N [4-(2,3-dimethylphenyl)-3-phenylpyridin-2-yl]methanol Chemical compound CC1=CC=CC(C=2C(=C(CO)N=CC=2)C=2C=CC=CC=2)=C1C MEAXTABTGJJRAA-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
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- ZBTGAUFOYLWRDH-UHFFFAOYSA-N [4-(3,4-dimethylphenyl)-3-phenylpyridin-2-yl]methanol Chemical compound C1=C(C)C(C)=CC=C1C1=CC=NC(CO)=C1C1=CC=CC=C1 ZBTGAUFOYLWRDH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WLPXNBYWDDYJTN-UHFFFAOYSA-N 1-bromo-2,3-dimethylbenzene Chemical group CC1=CC=CC(Br)=C1C WLPXNBYWDDYJTN-UHFFFAOYSA-N 0.000 description 1
- SHXFVLKSZCLZHF-UHFFFAOYSA-N 2-(chloromethyl)-4-(2,3-dimethylphenyl)-3-phenylpyridine Chemical compound CC1=CC=CC(C=2C(=C(CCl)N=CC=2)C=2C=CC=CC=2)=C1C SHXFVLKSZCLZHF-UHFFFAOYSA-N 0.000 description 1
- RFOXFGYCEBQABW-UHFFFAOYSA-N 2-[chloro-(3,4-dimethylphenyl)-phenylmethyl]pyridine Chemical compound C1=C(C)C(C)=CC=C1C(Cl)(C=1N=CC=CC=1)C1=CC=CC=C1 RFOXFGYCEBQABW-UHFFFAOYSA-N 0.000 description 1
- OVNQZEBNUOZSAU-UHFFFAOYSA-N 4-(2,3-dimethylphenyl)-2-(2-methylimidazol-1-yl)-3-phenylpyridine Chemical compound CC1=NC=CN1C1=NC=CC(C=2C(=C(C)C=CC=2)C)=C1C1=CC=CC=C1 OVNQZEBNUOZSAU-UHFFFAOYSA-N 0.000 description 1
- WPGXALXWADSWMG-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-2-(2-methylimidazol-1-yl)-3-phenylpyridine Chemical compound CC1=NC=CN1C1=NC=CC(C=2C=C(C)C(C)=CC=2)=C1C1=CC=CC=C1 WPGXALXWADSWMG-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000223203 Coccidioides Species 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
- 241001480035 Epidermophyton Species 0.000 description 1
- 241001480036 Epidermophyton floccosum Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000250507 Gigaspora candida Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241000228402 Histoplasma Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical class OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- MRUHVZDUDMOXJP-UHFFFAOYSA-M magnesium;1,2-dimethylbenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1C MRUHVZDUDMOXJP-UHFFFAOYSA-M 0.000 description 1
- PJYPCKZZTIAODG-UHFFFAOYSA-M magnesium;1,2-dimethylbenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=C[C-]=C1C PJYPCKZZTIAODG-UHFFFAOYSA-M 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
- 239000011976 maleic acid Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2229128A DE2229128C2 (de) | 1972-06-15 | 1972-06-15 | 1-(Dialkylphenyl-phenyl-pyridyl-)methyl-imidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136576B true NO136576B (hu) | 1977-06-20 |
| NO136576C NO136576C (no) | 1977-09-28 |
Family
ID=5847811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2482/73A NO136576C (no) | 1972-06-15 | 1973-06-14 | Analogifremgangsm}te til fremstilling av antimykotisk virksomme 1-(dimetylfenyl-fenyl-2 (eller 4)-pyridyl)-metyl-imidazoler og terapeutisk anvendelige salter |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3910936A (hu) |
| JP (2) | JPS4961175A (hu) |
| AR (2) | AR198669A1 (hu) |
| AT (1) | AT327192B (hu) |
| AU (1) | AU473104B2 (hu) |
| BE (1) | BE800914A (hu) |
| CA (1) | CA1006162A (hu) |
| CH (1) | CH579074A5 (hu) |
| DD (1) | DD107042A5 (hu) |
| DE (1) | DE2229128C2 (hu) |
| DK (1) | DK131780C (hu) |
| ES (2) | ES415904A1 (hu) |
| FI (1) | FI57946C (hu) |
| FR (1) | FR2189041B1 (hu) |
| GB (1) | GB1382755A (hu) |
| HU (1) | HU167707B (hu) |
| IL (1) | IL42494A (hu) |
| NL (1) | NL7308151A (hu) |
| NO (1) | NO136576C (hu) |
| PL (2) | PL90862B1 (hu) |
| SE (1) | SE403110B (hu) |
| SU (2) | SU488413A3 (hu) |
| ZA (1) | ZA734028B (hu) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA767103B (en) * | 1975-11-28 | 1977-10-26 | Scherico Ltd | Picolinic acid derivatives and processes for their preparation |
| US4755526A (en) * | 1984-06-18 | 1988-07-05 | Eli Lilly And Company | Method of inhibiting aromatase |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629273A (en) * | 1968-07-20 | 1971-12-21 | Bayer Ag | N-diaryl-pyridyl-methyl-imidazoles salts thereof |
| CH513893A (de) * | 1968-07-20 | 1971-10-15 | Bayer Ag | Verfahren zur Herstellung von N-Diaryl-pyridylmethyl-imidazolen und deren Salzen |
| DE1908991B2 (de) * | 1969-02-22 | 1977-05-26 | Bayer Ag, 5090 Leverkusen | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
| DE2009020C3 (de) * | 1970-02-26 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen |
| DE2016839C3 (de) * | 1970-04-09 | 1979-03-22 | Bayer Ag, 5090 Leverkusen | PhenyM4-phenoxyphenyi)-imidazol-1-yl-methane, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel |
-
1972
- 1972-06-15 DE DE2229128A patent/DE2229128C2/de not_active Expired
-
1973
- 1973-05-29 SU SU1926946A patent/SU488413A3/ru active
- 1973-06-07 US US367849A patent/US3910936A/en not_active Expired - Lifetime
- 1973-06-11 CA CA173,778A patent/CA1006162A/en not_active Expired
- 1973-06-12 JP JP48065486A patent/JPS4961175A/ja active Pending
- 1973-06-12 JP JP6548773A patent/JPS5643449B2/ja not_active Expired
- 1973-06-12 NL NL7308151A patent/NL7308151A/xx not_active Application Discontinuation
- 1973-06-12 AU AU56796/73A patent/AU473104B2/en not_active Expired
- 1973-06-13 PL PL1973163310A patent/PL90862B1/pl unknown
- 1973-06-13 FI FI1913/73A patent/FI57946C/fi active
- 1973-06-13 IL IL42494A patent/IL42494A/en unknown
- 1973-06-13 HU HUBA2939A patent/HU167707B/hu unknown
- 1973-06-13 PL PL1973187535A patent/PL94004B1/pl unknown
- 1973-06-13 CH CH853473A patent/CH579074A5/xx not_active IP Right Cessation
- 1973-06-13 DD DD171519A patent/DD107042A5/xx unknown
- 1973-06-14 DK DK330773A patent/DK131780C/da active
- 1973-06-14 ES ES0415904A patent/ES415904A1/es not_active Expired
- 1973-06-14 NO NO2482/73A patent/NO136576C/no unknown
- 1973-06-14 SE SE7308403A patent/SE403110B/xx unknown
- 1973-06-14 AR AR249583A patent/AR198669A1/es active
- 1973-06-14 GB GB2834173A patent/GB1382755A/en not_active Expired
- 1973-06-14 ZA ZA734028A patent/ZA734028B/xx unknown
- 1973-06-14 BE BE132269A patent/BE800914A/xx unknown
- 1973-06-15 FR FR7321892A patent/FR2189041B1/fr not_active Expired
- 1973-06-15 AT AT527673A patent/AT327192B/de not_active IP Right Cessation
-
1974
- 1974-06-18 AR AR254256A patent/AR202303A1/es active
- 1974-08-05 SU SU2048532A patent/SU509224A3/ru active
-
1975
- 1975-09-16 ES ES440991A patent/ES440991A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU473104B2 (en) | 1976-06-10 |
| AR198669A1 (es) | 1974-07-15 |
| DD107042A5 (hu) | 1974-07-12 |
| SE403110B (sv) | 1978-07-31 |
| AT327192B (de) | 1976-01-26 |
| PL90862B1 (hu) | 1977-02-28 |
| ES415904A1 (es) | 1976-06-01 |
| DK131780C (da) | 1976-02-09 |
| AU5679673A (en) | 1974-12-12 |
| ZA734028B (en) | 1974-05-29 |
| CH579074A5 (hu) | 1976-08-31 |
| CA1006162A (en) | 1977-03-01 |
| HU167707B (hu) | 1975-12-25 |
| SU509224A3 (ru) | 1976-03-30 |
| SU488413A3 (ru) | 1975-10-15 |
| JPS4961175A (hu) | 1974-06-13 |
| ATA527673A (de) | 1975-04-15 |
| NL7308151A (hu) | 1973-12-18 |
| ES440991A1 (es) | 1977-03-16 |
| DE2229128A1 (de) | 1974-01-03 |
| DE2229128C2 (de) | 1983-02-10 |
| US3910936A (en) | 1975-10-07 |
| IL42494A0 (en) | 1973-08-29 |
| AR202303A1 (es) | 1975-05-30 |
| FR2189041B1 (hu) | 1977-07-15 |
| FR2189041A1 (hu) | 1974-01-25 |
| JPS4961318A (hu) | 1974-06-14 |
| GB1382755A (en) | 1975-02-05 |
| PL94004B1 (hu) | 1977-07-30 |
| DK131780B (da) | 1975-09-01 |
| NO136576C (no) | 1977-09-28 |
| FI57946B (fi) | 1980-07-31 |
| JPS5643449B2 (hu) | 1981-10-13 |
| IL42494A (en) | 1976-04-30 |
| FI57946C (fi) | 1980-11-10 |
| BE800914A (fr) | 1973-12-14 |
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