DE2633492A1 - Derivate von substituierten n-alkylimidazolen und deren herstellung und verwendung - Google Patents

Derivate von substituierten n-alkylimidazolen und deren herstellung und verwendung

Info

Publication number: DE2633492A1
Authority: DE; Germany
Prior art keywords: imidazole; acid addition; addition salts; chlorophenyl; formula
Prior art date: 1975-07-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

DE19762633492

Other languages

German (de)

English (en)

Other versions

DE2633492C2 (fr

Inventor

Keith A M Walker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Syntex USA LLC

Original Assignee

Syntex USA LLC

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.)

1975-07-28

Filing date

1976-07-26

Publication date

1977-02-24

1976-07-26 Application filed by Syntex USA LLC filed Critical Syntex USA LLC

1977-02-24 Publication of DE2633492A1 publication Critical patent/DE2633492A1/de

1990-10-25 Application granted granted Critical

1990-10-25 Publication of DE2633492C2 publication Critical patent/DE2633492C2/de

Status Granted legal-status Critical Current

Links

RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 364
-1 3, 4-dichlorobenzylthio Chemical group 0.000 claims description 241
150000001875 compounds Chemical class 0.000 claims description 129
150000003839 salts Chemical class 0.000 claims description 71
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 61
239000002253 acid Substances 0.000 claims description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
238000000034 method Methods 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 26
239000002585 base Substances 0.000 claims description 19
241000233866 Fungi Species 0.000 claims description 16
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
241000894006 Bacteria Species 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000005504 styryl group Chemical group 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
230000000845 anti-microbial effect Effects 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
150000003568 thioethers Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052717 sulfur Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims 4
229940035339 tri-chlor Drugs 0.000 claims 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
239000004599 antimicrobial Substances 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 61
238000002844 melting Methods 0.000 description 40
230000008018 melting Effects 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
239000000243 solution Substances 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 19
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 19
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000003960 organic solvent Substances 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
QSWSKDXFOIOXKW-UHFFFAOYSA-N 1h-imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CNC=N1 QSWSKDXFOIOXKW-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000000047 product Substances 0.000 description 10
239000007787 solid Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 9
WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical compound O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
238000005187 foaming Methods 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000005283 haloketone group Chemical group 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000000463 material Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
150000002823 nitrates Chemical class 0.000 description 6
150000003891 oxalate salts Chemical class 0.000 description 6
235000006408 oxalic acid Nutrition 0.000 description 6
150000004714 phosphonium salts Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
229920001817 Agar Polymers 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000008272 agar Substances 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 4
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
238000006683 Mannich reaction Methods 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
150000002924 oxiranes Chemical group 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
229960005486 vaccine Drugs 0.000 description 4
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000008121 dextrose Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000001630 malic acid Substances 0.000 description 3
235000011090 malic acid Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
CEGBRSQPRQXALB-UHFFFAOYSA-N (3,4-dichlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C(Cl)=C1 CEGBRSQPRQXALB-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
HEKODEISZXHGMQ-UHFFFAOYSA-N 1-(2-chloro-4-phenylbutyl)imidazole;hydrochloride Chemical compound Cl.C1=CN=CN1CC(Cl)CCC1=CC=CC=C1 HEKODEISZXHGMQ-UHFFFAOYSA-N 0.000 description 2
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
CNJYHTOGVWWKJM-UHFFFAOYSA-N 1-imidazol-1-yl-4-phenylbut-3-en-2-ol Chemical compound C=1C=CC=CC=1C=CC(O)CN1C=CN=C1 CNJYHTOGVWWKJM-UHFFFAOYSA-N 0.000 description 2
GPUZWNNASIXLTQ-UHFFFAOYSA-N 1h-imidazole;oxalic acid Chemical compound C1=CNC=N1.OC(=O)C(O)=O GPUZWNNASIXLTQ-UHFFFAOYSA-N 0.000 description 2
JVGAGAVQROERFI-UHFFFAOYSA-N 2-(2-phenylethyl)oxirane Chemical compound C1OC1CCC1=CC=CC=C1 JVGAGAVQROERFI-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
239000004255 Butylated hydroxyanisole Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000222122 Candida albicans Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000019249 food preservative Nutrition 0.000 description 1
239000005452 food preservative Substances 0.000 description 1
238000001640 fractional crystallisation Methods 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
239000011521 glass Substances 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
229960002509 miconazole Drugs 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940051027 pasteurella multocida Drugs 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
206010052366 systemic mycosis Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
238000005406 washing Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (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)

DE19762633492 1975-07-28 1976-07-26 Derivate von substituierten n-alkylimidazolen und deren herstellung und verwendung Granted DE2633492A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US59961875A	1975-07-28	1975-07-28
US66502376A	1976-03-08	1976-03-08

Publications (2)

Publication Number	Publication Date
DE2633492A1 true DE2633492A1 (de)	1977-02-24
DE2633492C2 DE2633492C2 (fr)	1990-10-25

Family

ID=27083399

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19762633492 Granted DE2633492A1 (de)	1975-07-28	1976-07-26	Derivate von substituierten n-alkylimidazolen und deren herstellung und verwendung

Country Status (14)

Country	Link
JP (1)	JPS6028820B2 (fr)
AU (1)	AU505298B2 (fr)
CH (2)	CH621117A5 (fr)
DE (1)	DE2633492A1 (fr)
ES (2)	ES461980A1 (fr)
FR (1)	FR2319348A1 (fr)
GB (1)	GB1522717A (fr)
HK (1)	HK8480A (fr)
IE (1)	IE43409B1 (fr)
MX (1)	MX3866E (fr)
MY (1)	MY8000271A (fr)
NL (1)	NL183760C (fr)
NZ (1)	NZ181567A (fr)
PH (1)	PH14563A (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2800755A1 (de) *	1977-01-10	1978-07-13	Syntex Inc	1-eckige klammer auf 2-(halogenphenylthio)-4-(p-chlor- oder -fluorphenyl)-n-butyl eckige klammer zu -imidazole und ihre herstellung
EP0010287A1 (fr) *	1978-10-18	1980-04-30	BASF Aktiengesellschaft	Composés gamma-azolyliques, régulateurs de croissance, procédé pour leur préparation et méthode de régulation de la croissance des plantes
DE2912288A1 (de) *	1979-03-28	1980-10-09	Bayer Ag	Verfahren zur herstellung von hydroxyethyl-azolen
EP0041673A1 (fr) *	1980-06-06	1981-12-16	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Dérivés d'imidazole, leur préparation et compositions les contenant
EP0105575A1 (fr) *	1982-07-12	1984-04-18	G.D. Searle & Co.	Composés 1-(1H-imidazolyliques), 1-N-morpholinyliques et pyridyliques, leur préparation et compositions pharmaceutiques les contenant
EP0423524A2 (fr) *	1989-09-28	1991-04-24	MARUHO Co., Ltd.	Dérivés de propiophénone et leur préparation et application pharmaceutique

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE2963796D1 (en) *	1979-01-22	1982-11-11	Syntex Inc	Imidazole derivatives, pharmaceutical compositions containing them and their preparation
JPS55160767A (en) *	1979-05-31	1980-12-13	Idota Yutaka	Imidazole derivative
JPS6068220A (ja) *	1983-09-24	1985-04-18	株式会社マキ製作所	フル−ツキヤツプの自動装着方法と装置
JPH0829011B2 (ja) *	1987-11-16	1996-03-27	井関農機株式会社	苗移植機
JP6229896B2 (ja) *	2013-01-21	2017-11-15	国立大学法人大阪大学	フェノキシアルキルアミン化合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1940388A1 (de) *	1968-08-19	1970-02-26	Janssen Pharmaceutica Nv	Neue 1-(beta-Aryl)aethylimidazolderivate,ihre Herstellung und Verwendung
DE2063857A1 (de) *	1970-01-13	1971-07-22	Janssen Pharmaceutica, N.V , Beerse (Belgien)	Imidazoldenvate
DE2041771A1 (de) *	1970-08-22	1972-02-24	Bayer Ag	Neue Phenyl-imidazolyl-alkanyl-Derivate,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel

1976
- 1976-07-16 MX MX761776U patent/MX3866E/es unknown
- 1976-07-22 GB GB30685/76A patent/GB1522717A/en not_active Expired
- 1976-07-26 DE DE19762633492 patent/DE2633492A1/de active Granted
- 1976-07-26 AU AU16222/76A patent/AU505298B2/en not_active Expired
- 1976-07-26 FR FR7622761A patent/FR2319348A1/fr active Granted
- 1976-07-26 NZ NZ181567A patent/NZ181567A/xx unknown
- 1976-07-26 IE IE1651/76A patent/IE43409B1/en unknown
- 1976-07-27 PH PH18726A patent/PH14563A/en unknown
- 1976-07-27 NL NLAANVRAGE7608297,A patent/NL183760C/xx not_active IP Right Cessation
- 1976-07-27 JP JP51089590A patent/JPS6028820B2/ja not_active Expired
- 1976-07-28 CH CH967376A patent/CH621117A5/de not_active IP Right Cessation
1977
- 1977-08-30 ES ES461980A patent/ES461980A1/es not_active Expired
- 1977-08-30 ES ES461979A patent/ES461979A1/es not_active Expired
1980
- 1980-03-06 HK HK84/80A patent/HK8480A/xx unknown
- 1980-05-06 CH CH352280A patent/CH623040A5/de not_active IP Right Cessation
- 1980-12-30 MY MY271/80A patent/MY8000271A/xx unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1940388A1 (de) *	1968-08-19	1970-02-26	Janssen Pharmaceutica Nv	Neue 1-(beta-Aryl)aethylimidazolderivate,ihre Herstellung und Verwendung
DE2063857A1 (de) *	1970-01-13	1971-07-22	Janssen Pharmaceutica, N.V , Beerse (Belgien)	Imidazoldenvate
DE2041771A1 (de) *	1970-08-22	1972-02-24	Bayer Ag	Neue Phenyl-imidazolyl-alkanyl-Derivate,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2800755A1 (de) *	1977-01-10	1978-07-13	Syntex Inc	1-eckige klammer auf 2-(halogenphenylthio)-4-(p-chlor- oder -fluorphenyl)-n-butyl eckige klammer zu -imidazole und ihre herstellung
EP0010287A1 (fr) *	1978-10-18	1980-04-30	BASF Aktiengesellschaft	Composés gamma-azolyliques, régulateurs de croissance, procédé pour leur préparation et méthode de régulation de la croissance des plantes
DE2912288A1 (de) *	1979-03-28	1980-10-09	Bayer Ag	Verfahren zur herstellung von hydroxyethyl-azolen
EP0041673A1 (fr) *	1980-06-06	1981-12-16	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Dérivés d'imidazole, leur préparation et compositions les contenant
EP0105575A1 (fr) *	1982-07-12	1984-04-18	G.D. Searle & Co.	Composés 1-(1H-imidazolyliques), 1-N-morpholinyliques et pyridyliques, leur préparation et compositions pharmaceutiques les contenant
EP0423524A2 (fr) *	1989-09-28	1991-04-24	MARUHO Co., Ltd.	Dérivés de propiophénone et leur préparation et application pharmaceutique
EP0423524A3 (en) *	1989-09-28	1992-07-08	Maruho Co., Ltd.	Propiophenone derivatives and their preparation and pharmaceutical use

Also Published As

Publication number	Publication date
CH621117A5 (en)	1981-01-15
HK8480A (en)	1980-03-14
JPS6028820B2 (ja)	1985-07-06
FR2319348B1 (fr)	1979-07-13
DE2633492C2 (fr)	1990-10-25
FR2319348A1 (fr)	1977-02-25
ES461979A1 (es)	1978-12-01
NL183760B (nl)	1988-08-16
AU505298B2 (en)	1979-11-15
IE43409L (en)	1977-01-28
AU1622276A (en)	1978-02-02
GB1522717A (en)	1978-08-23
NZ181567A (en)	1978-04-28
MY8000271A (en)	1980-12-31
NL7608297A (nl)	1977-02-01
IE43409B1 (en)	1981-02-25
CH623040A5 (en)	1981-05-15
MX3866E (es)	1981-08-26
JPS5217472A (en)	1977-02-09
NL183760C (nl)	1989-01-16
PH14563A (en)	1981-09-24
ES461980A1 (es)	1978-06-01

Legal Events

Date	Code	Title
1983-10-20	8141	Disposal/no request for examination
1983-11-10	8110	Request for examination paragraph 44
1990-10-25	D2	Grant after examination
1991-04-25	8364	No opposition during term of opposition

Publication	Publication Date	Title
EP0043419B1 (fr)	1984-03-14	Composition antimycotique
US4078071A (en)	1978-03-07	Derivatives of substituted N-alkyl imidazoles
DD148219A5 (de)	1981-05-13	Verfahren zur herstellung von hydroxyethyl-azolen
EP0094564A2 (fr)	1983-11-23	Azolylméthyloxirannes, leur préparation et leur application comme médicaments et agents de protection des plantes
DE3237400A1 (de)	1984-04-12	Substituierte 1-hydroxyethyl-triazolyl-derivate
DE2504114A1 (de)	1975-08-07	Imidazoliumsalze
EP0011768A1 (fr)	1980-06-11	Hydroxypropyl triazoles, procédé pour leur préparation et médicaments contenant ces composés
DE2633492A1 (de)	1977-02-24	Derivate von substituierten n-alkylimidazolen und deren herstellung und verwendung
EP0054865A1 (fr)	1982-06-30	1-Azolyl-butan-2-ones substitués, procédé de leur préparation et leur application comme fongicides ainsi que comme intermédiaires
US4045568A (en)	1977-08-30	Derivatives of substituted N-alkyl imidazoles
EP0111234B1 (fr)	1986-10-08	Agents fongicides, leur préparation et utilisation
US4375474A (en)	1983-03-01	Dioxalane containing imidazole compounds, compositions and use
EP0085842A1 (fr)	1983-08-17	Moyens antimycosiques
EP0083750B1 (fr)	1985-08-07	Azolyl butanols antimycosiques
DE2800755C2 (fr)	1989-09-07
EP0105166A1 (fr)	1984-04-11	Dérivés substitués du tert. butanol, procédés pour leur préparation et agents antimycotiques les contenant
EP0090993B1 (fr)	1986-05-07	Azoles hydroxyalkyliques substitués, procédé pour leur préparation et leur utilisation comme antimycotiques
DE2541833C2 (fr)	1989-09-14
EP0370300A2 (fr)	1990-05-30	Azolylméthyl-carbinoles substitués par un groupe cyclopropyle, procédé de préparation et leur application comme médicaments
EP0037049A1 (fr)	1981-10-07	Dérivés de biphénylyl-imidazolyléthane, procédé pour leur préparation et médicaments les contenant
DE3314548A1 (de)	1984-10-25	Antimykotische mittel
EP0313983A2 (fr)	1989-05-03	Utilisation d'alcanols triazolyl pour le traitement de maladies
CA1077493A (fr)	1980-05-13	Derives de n-alkyl-imidazoles substitues
CH650502A5 (de)	1985-07-31	1-phenaethylimidazol-derivate.
EP0313984A1 (fr)	1989-05-03	Azolylméthyl carbinoles et préparations pharmaceutiques les contenant