NO126623B - - Google Patents

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Info

Publication number: NO126623B
Authority: NO; Norway
Prior art keywords: radical; halogen; lower alkyl; alkyl; formula
Prior art date: 1969-03-07

Application number

NO00780/70*[A

Other languages

English (en)

Norwegian (no)

Inventor

Wilfried Draber

Erik Regel

Karl-Heinz Buechel

Manfred Plempel

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1969-03-07

Filing date

1970-03-05

Publication date

1973-03-05

1969-03-07 Priority claimed from DE19691911646 external-priority patent/DE1911646C3/de

1970-03-05 Application filed by Bayer Ag filed Critical Bayer Ag

1973-03-05 Publication of NO126623B publication Critical patent/NO126623B/no

Links

150000001875 compounds Chemical class 0.000 claims description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
-1 pyridyl radical Chemical class 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical class C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
238000009835 boiling Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
241000233866 Fungi Species 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
239000000654 additive Substances 0.000 description 3
229940121375 antifungal agent Drugs 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 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
239000013078 crystal Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
241001480043 Arthrodermataceae 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
208000007163 Dermatomycoses Diseases 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000013543 active substance Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000037304 dermatophytes Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
229960000448 lactic acid Drugs 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229960004889 salicylic acid Drugs 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000003826 tablet Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
LLRFBQIIPSPPIS-UHFFFAOYSA-N 2-[diphenyl(thiophen-2-yl)methyl]-1H-imidazole Chemical compound C1(=CC=CC=C1)C(C=1NC=CN1)(C=1SC=CC1)C1=CC=CC=C1 LLRFBQIIPSPPIS-UHFFFAOYSA-N 0.000 description 1
APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
241000224432 Entamoeba histolytica Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
241000228402 Histoplasma Species 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 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
241001502500 Trichomonadida Species 0.000 description 1
GJEAMHAFPYZYDE-UHFFFAOYSA-N [C].[S] Chemical compound [C].[S] GJEAMHAFPYZYDE-UHFFFAOYSA-N 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
229960003942 amphotericin b Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036765 blood level Effects 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
FKPBWSNNHLBCQG-UHFFFAOYSA-N diphenyl(thiophen-2-yl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CS1 FKPBWSNNHLBCQG-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940007078 entamoeba histolytica Drugs 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000945 filler Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
244000000008 fungal human pathogen Species 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
229960002867 griseofulvin Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229960000443 hydrochloric acid Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
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241000894007 species Species 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO00780/70*[A 1969-03-07 1970-03-05 NO126623B (ro)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19691911646 DE1911646C3 (de)		1969-03-07	Heterocyclisch substituierte N-Diphenylmethylimidazole

Publications (1)

Publication Number	Publication Date
NO126623B true NO126623B (ro)	1973-03-05

Family

ID=5727440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00780/70*[A NO126623B (ro)	1969-03-07	1970-03-05

Country Status (20)

Country	Link
US (2)	US3709901A (ro)
AT (1)	AT293381B (ro)
BE (1)	BE746983A (ro)
BG (1)	BG17583A3 (ro)
BR (1)	BR6915465D0 (ro)
CH (1)	CH535239A (ro)
CS (1)	CS167278B2 (ro)
DK (1)	DK138795B (ro)
ES (1)	ES377249A1 (ro)
FI (1)	FI55193C (ro)
FR (1)	FR2034744B1 (ro)
GB (1)	GB1268745A (ro)
IE (1)	IE34037B1 (ro)
IL (1)	IL33918A (ro)
LU (1)	LU60444A1 (ro)
NL (1)	NL166022C (ro)
NO (1)	NO126623B (ro)
PL (1)	PL80468B1 (ro)
RO (1)	RO56152A (ro)
SE (1)	SE377802B (ro)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1964995A1 (de) *	1969-12-24	1971-07-01	Bayer Ag	N-Benzyltriazole,Verfahren zu ihrer Herstellung und ihre Verwendung zur Regulierung des Pflanzenwachstums
DE2013793C2 (de) *	1970-03-23	1983-02-03	Bayer Ag, 5090 Leverkusen	N-Methyl-imidazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2128700C2 (de) *	1971-06-09	1985-04-25	Bayer Ag, 5090 Leverkusen	Fungitoxische Mittel
DK157860C (da) *	1979-06-07	1990-07-30	Shionogi & Co	Analogifremgangsmaade til fremstilling af benzylimidazolderivater samt farmaceutisk acceptable syreadditionssalte deraf
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
US4717732A (en) *	1982-08-13	1988-01-05	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4701463A (en) *	1982-08-13	1987-10-20	The Dow Chemical Company	Pyridyl (pyridyloxy or pyriolylthio) azolomethanes
US4717734A (en) *	1982-08-13	1988-01-05	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4636514A (en) *	1982-08-13	1987-01-13	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes
US4716174A (en) *	1982-08-13	1987-12-29	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4728657A (en) *	1982-08-13	1988-03-01	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes
US4701207A (en) *	1982-08-13	1987-10-20	The Dow Chemical Company	Phenyl (phenoxy or phenylthio) azolomethanes
US4731372A (en) *	1982-08-13	1988-03-15	The Dow Chemical Company	Aryl(aryloxy or arylthio) azolomethanes, and their use as pesticides
US4720502A (en) *	1982-08-13	1988-01-19	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717733A (en) *	1982-08-13	1988-01-05	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4735960A (en) *	1984-06-18	1988-04-05	Eli Lilly And Company	Aromatase inhibitors
US4609666A (en) *	1984-06-18	1986-09-02	Eli Lilly And Company	Aromatase inhibiting derivatives of α,α-bis(4-halophenyl)methyltetrazoles and triazoles
US4560695A (en) *	1984-06-18	1985-12-24	Eli Lilly And Company	Isoxazolyl and isothiazolyl aromatase inhibitors
US4755526A (en) *	1984-06-18	1988-07-05	Eli Lilly And Company	Method of inhibiting aromatase
US4602025A (en) *	1984-06-18	1986-07-22	Eli Lilly And Company	Aromatase inhibitors
US4937250A (en) *	1988-03-07	1990-06-26	Ciba-Geigy Corporation	Alpha-heterocycle substituted tolunitriles
US4978672A (en) *	1986-03-07	1990-12-18	Ciba-Geigy Corporation	Alpha-heterocyclc substituted tolunitriles
US4749713A (en) *	1986-03-07	1988-06-07	Ciba-Geigy Corporation	Alpha-heterocycle substituted tolunitriles
IT1216256B (it) *	1986-08-13	1990-02-22	Menarini Sas	(benzofuran-2-il) imidazoli, con attivita' farmacologica,loro sali e procedimenti di fabbricazione relativi.
US4767867A (en) *	1987-04-10	1988-08-30	Pennwalt Corporation	5-(alkoxyalkyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4831154A (en) *	1987-04-10	1989-05-16	Pennwalt Corporation	5-alkyl(or alkenyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4767868A (en) *	1987-04-10	1988-08-30	Pennwalt Corporation	3-Phenyl-3-(1H-imidazol-1-ylmethyl)-2-methyl-5-[(phenylamino)methyl]isoxazolidines
US4769471A (en) *	1987-04-10	1988-09-06	Pennwalt Corporation	Substituted 3,5-diphenyl-3-(1H-1,2,4-triazol-1-yl-methyl)-2-methylisoxazolidines
US4767866A (en) *	1987-04-10	1988-08-30	Pennwalt Corporation	3-Phenyl-3-(1H-1,2,4-triazol-1-ylmethyl)-2-methyl-5-alkylisoxazolidines
US4769468A (en) *	1987-04-10	1988-09-06	Penwalt Corporation	5-(acyloxyalkyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4769470A (en) *	1987-10-02	1988-09-06	Pennwalt Corporation	5-(phenyl or phenoxyalkyl)-3-(2-thienyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4769469A (en) *	1987-04-10	1988-09-06	Pennwalt Corporation	5-(phenyl or phenoxyalkyl)-3-(2-furanyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4777262A (en) *	1987-10-02	1988-10-11	Pennwalt Corporation	5-(substituted thiomethyl)-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine derivatives
US4777264A (en) *	1987-10-02	1988-10-11	Pennwalt Corporation	5-carbonyl derivatives of 3-phenyl-3-(1H-imadazol-1-ylmethyl)-2-methylisoxazolidines and related compounds thereof
US4777263A (en) *	1987-10-02	1988-10-11	Pennwalt Corporation	5-substituted-3-(2-naphthalenyl)-3-((1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl))-2-methylisoxazolidines
US4749793A (en) *	1987-10-02	1988-06-07	Pennwalt Corporation	5-substituted-3-phenyl-3-[1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl]-2-benzylisoxazolidines (ir 3011)
US4754042A (en) *	1987-10-02	1988-06-28	Pennwalt Corporation	5-{[naphthyl(or 2-oxo-1,3-benzoxathiol-6-yl)oxy]methyl}-3-phenyl-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidines
US4785117A (en) *	1987-10-02	1988-11-15	Pennwalt Corporation	5,5-disubstituted-3-phenyl-3-phenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2-methylisoxazolidine derivatives (IR 3012)
US4835283A (en) *	1988-03-07	1989-05-30	Pennwalt Corporation	3,5-diphenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2
US5650533A (en) *	1989-09-11	1997-07-22	Rhone-Poulenc Agriculture Ltd.	Intermediates to herbicidal 4-substituted isoxazoles
US5747424A (en) *	1989-09-11	1998-05-05	Rhone-Poulenc Agriculture Ltd.	Herbicidal 4-substituted isoxazol
US5656573A (en) *	1989-09-11	1997-08-12	Rhone-Poulenc Agriculture Ltd.	Herbicidal 4-substituted isoxazoles
GB9017539D0 (en) *	1990-08-10	1990-09-26	Rhone Poulenc Agriculture	New compositions of matter

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3321366A (en) *	1965-11-15	1967-05-23	Dow Chemical Co	Fungicidal methods and compositions

1969
- 1969-12-19 BR BR215465/69A patent/BR6915465D0/pt unknown
1970
- 1970-02-06 CH CH172170A patent/CH535239A/de not_active IP Right Cessation
- 1970-02-17 IL IL33918A patent/IL33918A/en unknown
- 1970-02-25 RO RO62553A patent/RO56152A/ro unknown
- 1970-02-25 BG BG014048A patent/BG17583A3/xx unknown
- 1970-02-26 IE IE252/70A patent/IE34037B1/xx unknown
- 1970-02-27 FI FI544/70A patent/FI55193C/fi active
- 1970-03-03 AT AT195370A patent/AT293381B/de not_active IP Right Cessation
- 1970-03-03 LU LU60444D patent/LU60444A1/xx unknown
- 1970-03-03 GB GB00130/70A patent/GB1268745A/en not_active Expired
- 1970-03-04 US US00016219A patent/US3709901A/en not_active Expired - Lifetime
- 1970-03-04 CS CS1456A patent/CS167278B2/cs unknown
- 1970-03-05 NO NO00780/70*[A patent/NO126623B/no unknown
- 1970-03-06 DK DK113870AA patent/DK138795B/da unknown
- 1970-03-06 BE BE746983D patent/BE746983A/xx unknown
- 1970-03-06 SE SE7003021A patent/SE377802B/xx unknown
- 1970-03-06 NL NL7003260.A patent/NL166022C/xx not_active IP Right Cessation
- 1970-03-06 FR FR7008229A patent/FR2034744B1/fr not_active Expired
- 1970-03-06 PL PL1970139208A patent/PL80468B1/pl unknown
- 1970-03-07 ES ES377249A patent/ES377249A1/es not_active Expired
1972
- 1972-01-05 US US00215676A patent/US3794653A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US3794653A (en)	1974-02-26
SE377802B (ro)	1975-07-28
NL166022B (nl)	1981-01-15
IE34037B1 (en)	1975-01-08
FI55193B (fi)	1979-02-28
RO56152A (ro)	1974-04-29
DE1911646A1 (de)	1970-09-24
AT293381B (de)	1971-10-11
IL33918A0 (en)	1970-04-20
BG17583A3 (bg)	1973-11-10
CS167278B2 (ro)	1976-04-29
ES377249A1 (es)	1972-06-16
IE34037L (en)	1970-09-07
FI55193C (fi)	1979-06-11
NL166022C (nl)	1981-06-15
DK138795B (da)	1978-10-30
DE1911646B2 (de)	1977-05-18
DK138795C (ro)	1979-04-09
US3709901A (en)	1973-01-09
NL7003260A (ro)	1970-09-09
BR6915465D0 (pt)	1973-01-04
FR2034744B1 (ro)	1974-08-09
PL80468B1 (ro)	1975-08-30
IL33918A (en)	1973-05-31
LU60444A1 (ro)	1970-05-04
CH535239A (de)	1973-03-31
GB1268745A (en)	1972-03-29
BE746983A (fr)	1970-09-07
FR2034744A1 (ro)	1970-12-11

Publication	Publication Date	Title
NO126623B (ro)	1973-03-05
US3660576A (en)	1972-05-02	N-trityl-imidazoles for treating fungal infections
US3826836A (en)	1974-07-30	Phenyl-imidazolyl-fatty acid derivatives for treating mycotic infections
NO135787B (ro)	1977-02-21
US4171365A (en)	1979-10-16	Antiviral aryloxyalkylpyrazoles
US4021556A (en)	1977-05-03	Xanthine oxidase inhibitors
US4232161A (en)	1980-11-04	4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1-(2-pyridinyl)-1H-pyrazole
US4234725A (en)	1980-11-18	4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1-[4-(4-morpholinyl)-1-oxobutyl]-1H-pyrazole
US4261928A (en)	1981-04-14	2-Benzoyl-8-(2-chloro-4-methoxyphenoxy)-1-phenyl-1-octanone
US3764690A (en)	1973-10-09	Substituted n-benzylimidazoles as antimycotic agents
PL80618B1 (ro)	1975-08-30
NO742361L (ro)	1975-01-27
US4209526A (en)	1980-06-24	Antiviral arylenedioxyalkyl substituted pyrazoles
US4359475A (en)	1982-11-16	Thioketal substituted N-alkyl imidazoles
NO132395B (ro)	1975-07-28
US3787415A (en)	1974-01-22	N-methyl-imidazole derivatives and their production
US3629273A (en)	1971-12-21	N-diaryl-pyridyl-methyl-imidazoles salts thereof
US3818030A (en)	1974-06-18	1-imidazoyl-methanephosphonic acid esters
US3790594A (en)	1974-02-05	Thienyl-imidazolyl alkanoic acids
US3980796A (en)	1976-09-14	Substituted 2-alkoxycarbonylamine-5-(6)-phenylmercapto-benzimidazoles
US3978069A (en)	1976-08-31	Phenyl-imidazolyl-fatty acid derivatives
US3737531A (en)	1973-06-05	N-diaryl-pyridyl-methyl-imidazoles,salts thereof as antifungal agents
JPS63284186A (ja)	1988-11-21	４−トリアルキルシリルベンジルアミン誘導体、その製造法及び用途
NO161102B (no)	1989-03-28	Lokkemat for gnagere omfattende foede og en gift.
NO157214B (no)	1987-11-02	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolcarboxylsyrederivater.