CS250579B1 - Imidazole derivatives and method of their preparation - Google Patents
Imidazole derivatives and method of their preparation Download PDFInfo
- Publication number
- CS250579B1 CS250579B1 CS858664A CS866485A CS250579B1 CS 250579 B1 CS250579 B1 CS 250579B1 CS 858664 A CS858664 A CS 858664A CS 866485 A CS866485 A CS 866485A CS 250579 B1 CS250579 B1 CS 250579B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- imidazole
- chloroform
- formula
- reaction
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 150000002460 imidazoles Chemical class 0.000 title claims description 13
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 229910052801 chlorine Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 150000003333 secondary alcohols Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- -1 arylsulphonyl chloride Chemical compound 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- CNJBTSUNQWPABV-UHFFFAOYSA-N 1-imidazol-1-ylsulfinylimidazole Chemical group C1=CN=CN1S(=O)N1C=CN=C1 CNJBTSUNQWPABV-UHFFFAOYSA-N 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 7
- 208000031888 Mycoses Diseases 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- DWSJLOMKKVCTPJ-UHFFFAOYSA-N 5,10-dihydrothieno[2,3-c][2]benzothiepin-10-ol Chemical compound S1CC2=CC=CC=C2C(O)C2=C1SC=C2 DWSJLOMKKVCTPJ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 3
- 238000000338 in vitro Methods 0.000 abstract description 2
- 238000001727 in vivo Methods 0.000 abstract description 2
- UBNRYQRJBJFNIV-UHFFFAOYSA-N 2-thieno[2,3-i][1]benzothiepin-2-yl-1h-imidazole Chemical class S1C(C=2C=CSC=2C=C2)=C2C=CC=C1C1=NC=CN1 UBNRYQRJBJFNIV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Chemical group 0.000 abstract 1
- 230000001857 anti-mycotic effect Effects 0.000 abstract 1
- 230000002500 effect on skin Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241000222122 Candida albicans Species 0.000 description 5
- 229940095731 candida albicans Drugs 0.000 description 5
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 5
- 229960004022 clotrimazole Drugs 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 241001123227 Saccharomyces pastorianus Species 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 241000228245 Aspergillus niger Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960002509 miconazole Drugs 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229960004125 ketoconazole Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- CDGWCZUDUGLOLJ-UHFFFAOYSA-N 8-chloro-5,10-dihydrothieno[2,3-c][2]benzothiepin-10-ol Chemical compound S1CC2=CC=C(Cl)C=C2C(O)C2=C1SC=C2 CDGWCZUDUGLOLJ-UHFFFAOYSA-N 0.000 description 1
- YDOFTCHBMBLVOJ-UHFFFAOYSA-N 8-chloro-5h-thieno[2,3-c][2]benzothiepin-10-one Chemical compound O=C1C2=CC(Cl)=CC=C2CSC2=C1C=CS2 YDOFTCHBMBLVOJ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 206010064899 Vulvovaginal mycotic infection Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS858664A CS250579B1 (en) | 1985-11-29 | 1985-11-29 | Imidazole derivatives and method of their preparation |
| AT86308622T ATE57186T1 (de) | 1985-11-29 | 1986-11-05 | Imidazolylthienobenzothiepin-derivate und verfahren zu ihrer herstellung. |
| CA000522256A CA1278297C (en) | 1985-11-29 | 1986-11-05 | Imidazolyl thieno-benzothiepin derivatives and processes for theirpreparation |
| EP86308622A EP0226320B1 (de) | 1985-11-29 | 1986-11-05 | Imidazolylthienobenzothiepin-Derivate und Verfahren zu ihrer Herstellung |
| DE8686308622T DE3674741D1 (de) | 1985-11-29 | 1986-11-05 | Imidazolylthienobenzothiepin-derivate und verfahren zu ihrer herstellung. |
| JP61282172A JPS62132885A (ja) | 1985-11-29 | 1986-11-28 | イミダゾリルチエノ−ベンゾチエピン誘導体 |
| US06/936,540 US4730054A (en) | 1985-11-29 | 1986-12-01 | Imidazole thieno-benzothiepins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS858664A CS250579B1 (en) | 1985-11-29 | 1985-11-29 | Imidazole derivatives and method of their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS250579B1 true CS250579B1 (en) | 1987-04-16 |
Family
ID=5437511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS858664A CS250579B1 (en) | 1985-11-29 | 1985-11-29 | Imidazole derivatives and method of their preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4730054A (de) |
| EP (1) | EP0226320B1 (de) |
| JP (1) | JPS62132885A (de) |
| AT (1) | ATE57186T1 (de) |
| CA (1) | CA1278297C (de) |
| CS (1) | CS250579B1 (de) |
| DE (1) | DE3674741D1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5631210A (en) * | 1996-06-14 | 1997-05-20 | E. I. Du Pont De Nemours And Company | Herbicidal thiophene ketones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1081360A (en) * | 1965-08-25 | 1967-08-31 | Spofa Vereinigte Pharma Werke | Novel 4-substituted-4,5-dihydrothieno-(2,3-b)-benzo(f)thiepines and process for the preparation thereof |
| US4169205A (en) * | 1978-10-25 | 1979-09-25 | E. R. Squibb & Sons, Inc. | Imidazole derivatives of 6,11-dihydrodibenz[b,e]oxepines and 6,11-dihydrodibenz[b,e]thiepines |
-
1985
- 1985-11-29 CS CS858664A patent/CS250579B1/cs unknown
-
1986
- 1986-11-05 DE DE8686308622T patent/DE3674741D1/de not_active Expired - Fee Related
- 1986-11-05 EP EP86308622A patent/EP0226320B1/de not_active Expired - Lifetime
- 1986-11-05 AT AT86308622T patent/ATE57186T1/de active
- 1986-11-05 CA CA000522256A patent/CA1278297C/en not_active Expired - Fee Related
- 1986-11-28 JP JP61282172A patent/JPS62132885A/ja active Pending
- 1986-12-01 US US06/936,540 patent/US4730054A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3674741D1 (de) | 1990-11-08 |
| EP0226320A1 (de) | 1987-06-24 |
| CA1278297C (en) | 1990-12-27 |
| US4730054A (en) | 1988-03-08 |
| JPS62132885A (ja) | 1987-06-16 |
| ATE57186T1 (de) | 1990-10-15 |
| EP0226320B1 (de) | 1990-10-03 |
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