NO135363B - - Google Patents
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- Publication number
- NO135363B NO135363B NO75750727A NO750727A NO135363B NO 135363 B NO135363 B NO 135363B NO 75750727 A NO75750727 A NO 75750727A NO 750727 A NO750727 A NO 750727A NO 135363 B NO135363 B NO 135363B
- Authority
- NO
- Norway
- Prior art keywords
- group
- infection
- phenyl
- acid
- diphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- -1 phenyl-imidazolyl Chemical class 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 208000015181 infectious disease Diseases 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000037396 body weight Effects 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241001480043 Arthrodermataceae Species 0.000 description 4
- 208000007163 Dermatomycoses Diseases 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 241000799767 Scutula Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000037304 dermatophytes Effects 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- PTKAGHMFWYFHBU-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)C1=NC=CN1 PTKAGHMFWYFHBU-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 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
- 201000003929 dermatomycosis Diseases 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 241000700199 Cavia porcellus Species 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
- 208000031888 Mycoses Diseases 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- 241001609979 Trichophyton quinckeanum Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 244000053095 fungal pathogen Species 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OMLSYNQYPRJYAR-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 OMLSYNQYPRJYAR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 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
- XQYVDDAXTYTKDB-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)N)C1=CC=CC=C1 XQYVDDAXTYTKDB-UHFFFAOYSA-N 0.000 description 1
- RLBXCQGSVGQNJA-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)(Cl)C1=CC=CC=C1 RLBXCQGSVGQNJA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000222122 Candida albicans Species 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
- 241000250507 Gigaspora candida Species 0.000 description 1
- 241000228402 Histoplasma Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000371966 Penicillus <bivalve> Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 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
- 208000002474 Tinea Diseases 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 206010067409 Trichophytosis Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 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
- 229940095731 candida albicans Drugs 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000002775 capsule Substances 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006210 lotion 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- SXDQVXFVMMLCCV-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)acetate Chemical compound COC(=O)CC1=NC=CN1 SXDQVXFVMMLCCV-UHFFFAOYSA-N 0.000 description 1
- ILVSUJHMWHCKOI-UHFFFAOYSA-N methyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ILVSUJHMWHCKOI-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment 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
- 239000006072 paste Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2041771A DE2041771C3 (de) | 1970-08-22 | 1970-08-22 | derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO750727L NO750727L (bg) | 1972-02-23 |
| NO135363B true NO135363B (bg) | 1976-12-20 |
| NO135363C NO135363C (no) | 1977-03-30 |
Family
ID=5780483
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3118/71A NO133402C (bg) | 1970-08-22 | 1971-08-20 | |
| NO750727A NO135363C (no) | 1970-08-22 | 1975-03-04 | Analogifremgangsm}te til fremstilling av fenyl-imidazolyl-alkanylderivater med antimykotisk virkning. |
| NO75750726A NO135787C (bg) | 1970-08-22 | 1975-03-04 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3118/71A NO133402C (bg) | 1970-08-22 | 1971-08-20 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO75750726A NO135787C (bg) | 1970-08-22 | 1975-03-04 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US3796704A (bg) |
| JP (3) | JPS5640716B1 (bg) |
| AR (1) | AR193119A1 (bg) |
| AT (3) | AT315836B (bg) |
| AU (1) | AU462239B2 (bg) |
| BE (1) | BE771584A (bg) |
| BG (3) | BG19802A3 (bg) |
| CA (1) | CA923898A (bg) |
| CH (3) | CH567486A5 (bg) |
| DD (1) | DD94821A5 (bg) |
| DE (1) | DE2041771C3 (bg) |
| EG (1) | EG10169A (bg) |
| ES (2) | ES394421A1 (bg) |
| FI (1) | FI55500C (bg) |
| FR (1) | FR2103452B1 (bg) |
| GB (1) | GB1354909A (bg) |
| HU (1) | HU163071B (bg) |
| IE (1) | IE35547B1 (bg) |
| IL (1) | IL37537A (bg) |
| LU (1) | LU63699A1 (bg) |
| NL (1) | NL7111537A (bg) |
| NO (3) | NO133402C (bg) |
| PH (1) | PH10341A (bg) |
| PL (5) | PL99299B1 (bg) |
| RO (3) | RO64158A (bg) |
| SE (3) | SE387342B (bg) |
| SU (3) | SU451244A3 (bg) |
| YU (1) | YU34679B (bg) |
| ZA (1) | ZA715635B (bg) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892764A (en) * | 1970-08-22 | 1975-07-01 | Bayer Ag | Phenyl-imidazolyl-alkanyl derivatives, their production and use |
| DE2242454A1 (de) * | 1972-08-29 | 1974-03-07 | Bayer Ag | 1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US3928374A (en) * | 1973-06-22 | 1975-12-23 | Janssen Pharmaceutica Nv | Nitroimidazole derivatives |
| DE2348663A1 (de) * | 1973-09-27 | 1975-04-03 | Bayer Ag | Verfahren zur herstellung von neuen 1-aethyl-azolylderivaten |
| DE2350123C2 (de) * | 1973-10-05 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | 1-Propyl-imidazol-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| IL47885A (en) * | 1974-09-23 | 1979-01-31 | Syntex Inc | Imidazole derivatives,their preparation and antifungal and antibacterial compositions containing them |
| EG11928A (en) * | 1974-12-16 | 1979-03-31 | Hoechst Ag | Process for preparing of 1-alkyl-2-(phenoxy-methyl)-5-nitro-imidazoles |
| CA1065873A (en) * | 1975-01-27 | 1979-11-06 | Janssen Pharmaceutica Naamloze Vennootschap | Imidazole derivatives |
| US4085209A (en) * | 1975-02-05 | 1978-04-18 | Rohm And Haas Company | Preparation and safening effect of 1-substituted imidazole metal salt complexes |
| US4055652A (en) * | 1975-07-07 | 1977-10-25 | Syntex (U.S.A.) Inc. | 1-[β(R-thio)phenethyl]imidazoles and derivatives thereof |
| EG12284A (en) * | 1975-07-12 | 1978-09-30 | Hoechst Ag | Process for the preparation of 1-methyl-2-(phenyl 6 oxymethyl)-5-nitro-imidazoles |
| US4045568A (en) * | 1975-07-28 | 1977-08-30 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
| US4078071A (en) * | 1976-03-08 | 1978-03-07 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
| MX3866E (es) * | 1975-07-28 | 1981-08-26 | Syntex Inc | Metodo mejorado para preparar derivados de imidazoles n-alquil sustituidos |
| DE2604761A1 (de) * | 1976-02-07 | 1977-08-11 | Bayer Ag | Acylierte imidazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US4172141A (en) * | 1976-03-17 | 1979-10-23 | Syntex (U.S.A.) Inc. | N-(naphthylethyl)imidazole derivatives |
| DE2635666A1 (de) * | 1976-08-07 | 1978-02-09 | Bayer Ag | 1-azolyl-4-hydroxy-butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und bakterizide |
| DE2635665A1 (de) * | 1976-08-07 | 1978-02-09 | Bayer Ag | Antimikrobielle mittel |
| US4123542A (en) * | 1977-01-19 | 1978-10-31 | Syntex (U.S.A.) Inc. | Derivatives of N-alkyl imidazoles |
| US4213991A (en) * | 1978-05-30 | 1980-07-22 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles and compositions and methods containing the same |
| US4215220A (en) * | 1978-09-11 | 1980-07-29 | Cilag-Chemie A.G. | 1-(2-Oxysubstituted-3-anilinopropyl)-imidazoles |
| US4439441A (en) * | 1979-01-11 | 1984-03-27 | Syntex (U.S.A.) Inc. | Contraceptive compositions and methods employing 1-substituted imidazole derivatives |
| US4430445A (en) | 1979-07-19 | 1984-02-07 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel basic imidazolylmethylstyrene compound, its polymer, a process for the preparation thereof and a use as ion exchange resin |
| US4458079A (en) * | 1980-08-08 | 1984-07-03 | Bristol-Myers Company | Sulfur-containing imidazoles |
| DE3045055A1 (de) * | 1980-11-29 | 1982-07-01 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Heterocyclische verbindungen |
| DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| DE3644616A1 (de) * | 1986-12-29 | 1988-07-07 | Lentia Gmbh | Imidazolderivate, verfahren zur herstellung und deren verwendung |
| DE3707151A1 (de) * | 1987-03-06 | 1988-09-15 | Hoechst Ag | 1-(1-aryl-2-hydroxy-ethyl)-imidazole und deren salze, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| GB9127304D0 (en) * | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| GB9312893D0 (en) * | 1993-06-22 | 1993-08-04 | Boots Co Plc | Therapeutic agents |
| GB9409882D0 (en) * | 1994-05-18 | 1994-07-06 | Sandoz Ltd | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
-
1970
- 1970-08-22 DE DE2041771A patent/DE2041771C3/de not_active Expired
-
1971
- 1971-08-11 EG EG358/71A patent/EG10169A/xx active
- 1971-08-11 LU LU63699D patent/LU63699A1/xx unknown
- 1971-08-16 US US00172201A patent/US3796704A/en not_active Expired - Lifetime
- 1971-08-17 BG BG019805A patent/BG19802A3/bg unknown
- 1971-08-17 CA CA120737A patent/CA923898A/en not_active Expired
- 1971-08-17 BG BG018370A patent/BG20589A3/bg unknown
- 1971-08-17 BG BG019804A patent/BG19162A3/bg unknown
- 1971-08-18 HU HUBA2631A patent/HU163071B/hu unknown
- 1971-08-18 AU AU32467/71A patent/AU462239B2/en not_active Expired
- 1971-08-19 RO RO7100067999A patent/RO64158A/ro unknown
- 1971-08-19 SU SU1861747A patent/SU451244A3/ru active
- 1971-08-19 YU YU2137/71A patent/YU34679B/xx unknown
- 1971-08-19 IE IE1048/71A patent/IE35547B1/xx unknown
- 1971-08-19 RO RO7170518A patent/RO67637A/ro unknown
- 1971-08-19 SU SU1693076A patent/SU415875A3/ru active
- 1971-08-19 RO RO7170519A patent/RO64454A/ro unknown
- 1971-08-20 NL NL7111537A patent/NL7111537A/xx not_active Application Discontinuation
- 1971-08-20 AT AT1007072A patent/AT315836B/de not_active IP Right Cessation
- 1971-08-20 DD DD157236A patent/DD94821A5/xx unknown
- 1971-08-20 AT AT730071A patent/AT310739B/de not_active IP Right Cessation
- 1971-08-20 GB GB3919671A patent/GB1354909A/en not_active Expired
- 1971-08-20 IL IL37537A patent/IL37537A/xx unknown
- 1971-08-20 NO NO3118/71A patent/NO133402C/no unknown
- 1971-08-20 CH CH251375A patent/CH567486A5/xx not_active IP Right Cessation
- 1971-08-20 FR FR7130448A patent/FR2103452B1/fr not_active Expired
- 1971-08-20 BE BE771584A patent/BE771584A/xx unknown
- 1971-08-20 CH CH251275A patent/CH580594A5/xx not_active IP Right Cessation
- 1971-08-20 CH CH1228471A patent/CH568981A5/xx not_active IP Right Cessation
- 1971-08-20 FI FI2333/71A patent/FI55500C/fi active
- 1971-08-20 PH PH12767A patent/PH10341A/en unknown
- 1971-08-20 AT AT1006972A patent/AT315835B/de not_active IP Right Cessation
- 1971-08-21 PL PL1971187174A patent/PL99299B1/pl unknown
- 1971-08-21 PL PL1971187173A patent/PL98624B1/pl unknown
- 1971-08-21 JP JP6337671A patent/JPS5640716B1/ja active Pending
- 1971-08-21 PL PL1971150130A patent/PL81801B1/pl unknown
- 1971-08-21 ES ES394421A patent/ES394421A1/es not_active Expired
- 1971-08-21 PL PL1971176733A patent/PL96369B1/pl unknown
- 1971-08-21 PL PL1971176730A patent/PL95241B1/pl unknown
- 1971-08-23 ZA ZA715635A patent/ZA715635B/xx unknown
- 1971-08-23 SE SE7110671A patent/SE387342B/xx unknown
- 1971-09-23 SE SE7404140A patent/SE387941B/xx unknown
-
1972
- 1972-06-07 ES ES72403583A patent/ES403583A1/es not_active Expired
- 1972-07-26 AR AR243281A patent/AR193119A1/es active
- 1972-12-22 SU SU1861748A patent/SU552025A3/ru active
-
1974
- 1974-03-27 SE SE7404139A patent/SE405115B/xx unknown
-
1975
- 1975-03-04 NO NO750727A patent/NO135363C/no unknown
- 1975-03-04 NO NO75750726A patent/NO135787C/no unknown
-
1981
- 1981-03-16 JP JP3667481A patent/JPS56156266A/ja active Pending
- 1981-03-16 JP JP3667381A patent/JPS56156265A/ja active Pending
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