DD146824A5 - Verfahren zur herstellung von hydroxypropyl-triazolen - Google Patents

Verfahren zur herstellung von hydroxypropyl-triazolen Download PDF

Info

Publication number: DD146824A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; triazole; optionally substituted; compounds; phenyl
Prior art date: 1978-11-25

Application number

DD79217019A

Other languages

German (de)

English (en)

Inventor

Erik Regel

Karl H Buechel

Ingo Haller

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.)

1978-11-25

Filing date

1979-11-20

Publication date

1981-03-04

1979-11-20 Application filed by Bayer Ag filed Critical Bayer Ag

1981-03-04 Publication of DD146824A5 publication Critical patent/DD146824A5/de

Links

-1 HYDROXYPROPYL-TRIAZOLENE Chemical compound 0.000 title description 45
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
ICGHHKXZWABEBX-UHFFFAOYSA-N 3-(2h-triazol-4-yl)propan-1-ol Chemical class OCCCC1=CNN=N1 ICGHHKXZWABEBX-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
150000003852 triazoles Chemical class 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 4
239000000460 chlorine Substances 0.000 claims description 41
238000000034 method Methods 0.000 claims description 25
229910052801 chlorine Inorganic materials 0.000 claims description 15
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
150000002576 ketones Chemical class 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
239000011230 binding agent Substances 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 2
101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 2
101150109310 msrAB1 gene Proteins 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
125000001309 chloro group Chemical group Cl* 0.000 description 15
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 12
239000013543 active substance Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
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239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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238000006243 chemical reaction Methods 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
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230000000843 anti-fungal effect Effects 0.000 description 5
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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239000008298 dragée Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
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229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
229910052783 alkali metal Inorganic materials 0.000 description 3
235000012216 bentonite Nutrition 0.000 description 3
239000013078 crystal Substances 0.000 description 3
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150000003254 radicals Chemical class 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
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235000012222 talc Nutrition 0.000 description 3
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PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
CNAHQWRKXSWOST-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)propan-2-ol Chemical compound CC(O)CC1=CC=C(Cl)C=C1Cl CNAHQWRKXSWOST-UHFFFAOYSA-N 0.000 description 2
MUGXHBORJBOPIB-UHFFFAOYSA-N 1-chloro-3-phenyl-2-(4-phenylphenyl)propan-2-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CCl)(O)CC1=CC=CC=C1 MUGXHBORJBOPIB-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
IQEIGQFNDLINOT-UHFFFAOYSA-N 2-chloro-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CCl)=CC=C1C1=CC=CC=C1 IQEIGQFNDLINOT-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000416162 Astragalus gummifer 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
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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208000031888 Mycoses Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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229920001615 Tragacanth Polymers 0.000 description 2
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XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000001857 anti-mycotic effect Effects 0.000 description 2
229940121375 antifungal agent Drugs 0.000 description 2
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239000000440 bentonite Substances 0.000 description 2
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SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
GVNSCNGKEXNKBU-UHFFFAOYSA-M magnesium;1-chloro-4-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(Cl)C=C1 GVNSCNGKEXNKBU-UHFFFAOYSA-M 0.000 description 2
GVZMYROGYRWDEM-UHFFFAOYSA-M magnesium;2,4-dichloro-1-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=C(Cl)C=C1Cl GVZMYROGYRWDEM-UHFFFAOYSA-M 0.000 description 2
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XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
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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 1
229930195725 Mannitol Natural products 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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241000228143 Penicillium Species 0.000 description 1
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239000004952 Polyamide Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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244000299461 Theobroma cacao Species 0.000 description 1
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238000010521 absorption reaction Methods 0.000 description 1
VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
231100000360 alopecia Toxicity 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
150000003974 aralkylamines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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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
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229910052791 calcium Inorganic materials 0.000 description 1
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239000000378 calcium silicate Substances 0.000 description 1
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235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
229940095731 candida albicans Drugs 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
150000001735 carboxylic acids Chemical class 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
230000007547 defect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
239000010642 eucalyptus oil Substances 0.000 description 1
229940044949 eucalyptus oil Drugs 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
210000001035 gastrointestinal tract 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
235000001727 glucose Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000003906 humectant Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 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
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
PHSLYQFWLCWIBU-UHFFFAOYSA-M magnesium;1-chloro-2-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1Cl PHSLYQFWLCWIBU-UHFFFAOYSA-M 0.000 description 1
OKSMQYZDGFBKPL-UHFFFAOYSA-M magnesium;1-chloro-3-fluoro-2-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=C(F)C=CC=C1Cl OKSMQYZDGFBKPL-UHFFFAOYSA-M 0.000 description 1
BQNQIHYLDYHYQP-UHFFFAOYSA-M magnesium;1-chloro-3-methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC(Cl)=C1 BQNQIHYLDYHYQP-UHFFFAOYSA-M 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
- 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)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD79217019A 1978-11-25 1979-11-20 Verfahren zur herstellung von hydroxypropyl-triazolen DD146824A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782851086 DE2851086A1 (de)	1978-11-25	1978-11-25	Hydroxypropyl-triazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD146824A5 true DD146824A5 (de)	1981-03-04

Family

ID=6055560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79217019A DD146824A5 (de)	1978-11-25	1979-11-20	Verfahren zur herstellung von hydroxypropyl-triazolen

Country Status (18)

Country	Link
US (1)	US4381306A (fr)
EP (1)	EP0011768B1 (fr)
JP (1)	JPS55108860A (fr)
AT (1)	ATE324T1 (fr)
AU (1)	AU536920B2 (fr)
CA (1)	CA1130296A (fr)
DD (1)	DD146824A5 (fr)
DE (2)	DE2851086A1 (fr)
DK (1)	DK152493C (fr)
ES (1)	ES486279A1 (fr)
FI (1)	FI65992C (fr)
HU (1)	HU179414B (fr)
IE (1)	IE48880B1 (fr)
IL (1)	IL58782A (fr)
NO (1)	NO793673L (fr)
NZ (1)	NZ192195A (fr)
PH (1)	PH16119A (fr)
ZA (1)	ZA796356B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0105166A1 (fr) *	1982-09-02	1984-04-11	Bayer Ag	Dérivés substitués du tert. butanol, procédés pour leur préparation et agents antimycotiques les contenant

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4654332A (en) *	1979-03-07	1987-03-31	Imperial Chemical Industries Plc	Heterocyclic compounds
US4927839A (en) *	1979-03-07	1990-05-22	Imperial Chemical Industries Plc	Method of preventing fungal attack on wood, hides, leather or paint films using a triazole
US4551469A (en) *	1979-03-07	1985-11-05	Imperial Chemical Industries Plc	Antifungal triazole ethanol derivatives
DE3018865A1 (de) *	1980-05-16	1981-11-26	Bayer Ag, 5090 Leverkusen	Antimikrobielle mittel
AU542623B2 (en) *	1980-05-16	1985-02-28	Bayer Aktiengesellschaft	1-hydroxyethyl-azole derivatives
EP0131684B1 (fr) *	1980-08-18	1992-03-11	Imperial Chemical Industries Plc	Utilization des dérivés de triazolyléthanols et leurs compositions comme fongicides en dehors de l'agriculture
EP0046337A3 (fr) *	1980-08-20	1982-09-15	Imperial Chemical Industries Plc	Composés de triazole, leur procédé de préparation, leur application comme fongicides pour plantes, comme fongicides à activité pharmaceutique et comme régulateurs de la croissance de plantes et compositions les contenant
ZA815700B (en) *	1980-08-28	1982-08-25	Ici Ltd	Pharmaceutical compositions
AT375359B (de) *	1980-09-02	1984-07-25	Ici Plc	Verfahren zur herstellung von neuen verbindungen
AU8314482A (en) *	1981-05-19	1982-11-25	Imperial Chemical Industries Plc	3-triazolyl(imidazolyl)-2,2 bis phenyl-propionamides
DE3245504A1 (de) *	1982-12-09	1984-06-14	Bayer Ag, 5090 Leverkusen	Fungizide mittel, deren herstellung und verwendung
DE3461637D1 (en) *	1983-02-16	1987-01-22	Pfizer Ltd	Triazole antifungal agents
US5096889A (en) *	1987-11-09	1992-03-17	Bayer Ag	Antimycotic compositions of nikkomycin compounds and azole antimycotics
US5006513A (en) *	1987-11-09	1991-04-09	Miles Inc.	Antimycotic compositions of nikkomycin compounds and azole antimycotica
US5194427A (en) *	1987-11-09	1993-03-16	Bayer Ag	Antimycotic compositions of nikkomycin compounds and azole antimycotics
ATE72119T1 (de) *	1987-11-09	1992-02-15	Bayer Ag	Antimycotische zusammensetzungen aus nikkomycin- verbindungen und antimycotischem azol.
EP0321211A1 (fr) *	1987-12-17	1989-06-21	E.I. Du Pont De Nemours And Company	Carbinols antifongiques
US4914087A (en) *	1988-02-29	1990-04-03	Bayer Ag	Nikkomycin derivatives, antimycotic compositions of nikkomycin derivatives and azole antimycotics
US5098920A (en) *	1990-05-04	1992-03-24	G. D. Searle & Co.	1h-substituted-1,2,4-triazole compounds and methods of use thereof for treatment of cardiovascular disorders
US5155117A (en) *	1991-04-12	1992-10-13	G. D. Searle & Co.	1-arylheteroarylalkyl substituted-1h-1,2,4-triazole compounds for treatment of circulatory disorders

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4002763A (en) *	1972-09-26	1977-01-11	Bayer Aktiengesellschaft	1,2,4-Triazole antimycotic compositions and use thereof
DE2324424A1 (de) *	1973-05-15	1974-12-05	Bayer Ag	Antimikrobielle mittel
DE2431407C2 (de) *	1974-06-29	1982-12-02	Bayer Ag, 5090 Leverkusen	1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
GB1569267A (en) *	1975-12-16	1980-06-11	Ici Ltd	Substituted propiophenones and herbicidal and fungicidal compositions containing them
DE2623129C3 (de) *	1976-05-22	1980-04-10	Nordmark-Werke Gmbh, 2000 Hamburg	U-Diphenyl-3-(imidazol-l-yl) -propan-2-ole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2705679A1 (de) *	1977-02-11	1978-08-17	Bayer Ag	Antimikrobielle mittel

1978
- 1978-11-25 DE DE19782851086 patent/DE2851086A1/de not_active Withdrawn
1979
- 1979-11-09 US US06/092,805 patent/US4381306A/en not_active Expired - Lifetime
- 1979-11-13 NO NO793673A patent/NO793673L/no unknown
- 1979-11-14 AT AT79104483T patent/ATE324T1/de not_active IP Right Cessation
- 1979-11-14 DE DE7979104483T patent/DE2961083D1/de not_active Expired
- 1979-11-14 EP EP79104483A patent/EP0011768B1/fr not_active Expired
- 1979-11-20 DD DD79217019A patent/DD146824A5/de unknown
- 1979-11-22 JP JP15080079A patent/JPS55108860A/ja active Granted
- 1979-11-22 IL IL58782A patent/IL58782A/xx unknown
- 1979-11-22 NZ NZ192195A patent/NZ192195A/xx unknown
- 1979-11-23 ES ES486279A patent/ES486279A1/es not_active Expired
- 1979-11-23 FI FI793688A patent/FI65992C/fi not_active IP Right Cessation
- 1979-11-23 DK DK499679A patent/DK152493C/da not_active IP Right Cessation
- 1979-11-23 ZA ZA00796356A patent/ZA796356B/xx unknown
- 1979-11-23 CA CA340,546A patent/CA1130296A/fr not_active Expired
- 1979-11-23 PH PH23326A patent/PH16119A/en unknown
- 1979-11-23 HU HU79BA3891A patent/HU179414B/hu not_active IP Right Cessation
- 1979-11-23 IE IE2241/79A patent/IE48880B1/en unknown
- 1979-11-26 AU AU53172/79A patent/AU536920B2/en not_active Ceased

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0105166A1 (fr) *	1982-09-02	1984-04-11	Bayer Ag	Dérivés substitués du tert. butanol, procédés pour leur préparation et agents antimycotiques les contenant

Also Published As

Publication number	Publication date
IE48880B1 (en)	1985-06-12
EP0011768A1 (fr)	1980-06-11
ES486279A1 (es)	1980-05-16
DK152493B (da)	1988-03-07
HU179414B (en)	1982-10-28
NO793673L (no)	1980-05-28
DE2851086A1 (de)	1980-06-04
AU536920B2 (en)	1984-05-31
AU5317279A (en)	1980-05-29
DK152493C (da)	1988-07-25
FI793688A7 (fi)	1980-05-26
IL58782A0 (en)	1980-02-29
FI65992C (fi)	1984-08-10
CA1130296A (fr)	1982-08-24
ATE324T1 (de)	1981-11-15
IE792241L (en)	1980-05-25
DK499679A (da)	1980-05-26
US4381306A (en)	1983-04-26
NZ192195A (en)	1981-10-19
PH16119A (en)	1983-06-30
DE2961083D1 (en)	1981-12-24
JPS6258355B2 (fr)	1987-12-05
ZA796356B (en)	1980-12-31
FI65992B (fi)	1984-04-30
IL58782A (en)	1984-02-29
EP0011768B1 (fr)	1981-10-21
JPS55108860A (en)	1980-08-21

Publication	Publication Date	Title
EP0011769B1 (fr)	1982-04-14	Hydroxyéthyl azoles, procédé pour leur préparation ainsi que leur utilisation dans des médicaments
EP0011768B1 (fr)	1981-10-21	Hydroxypropyl triazoles, procédé pour leur préparation et médicaments contenant ces composés
DE3018865A1 (de)	1981-11-26	Antimikrobielle mittel
EP0005250B1 (fr)	1981-08-12	Hydroxypropyl-imidazoles, procédé pour leur préparation et médicaments les contenant
EP0120276A1 (fr)	1984-10-03	Diazolylalkyl ou triazolylalkyl carbinols substitués, leur procédé de préparation et leur application comme agents antimycosiques
DE2720868A1 (de)	1978-11-23	Antimikrobielle mittel
EP0003796B1 (fr)	1980-10-15	Diphényl-imidazolyl-méthanes substitués, leur procédé de préparation et médicaments les contenant
EP0180835B1 (fr)	1989-09-06	Dérivés d'azolylcyclopropylcarbinals à activité antimycotique
EP0180850A2 (fr)	1986-05-14	Dérivés d'azolylméthyl-cyclopropyl-carbinols antimycotiques
EP0088874B1 (fr)	1986-04-09	Azolyl-phénoxy-tétrahydrofuran-2-yliden-méthanes, leur procédé de préparation ainsi que les microbicides les contenant
EP0118070B1 (fr)	1986-10-08	1,3-Diazolyl-2-propanols substitués, leur procédé de préparation et leur application comme antimycosiques
EP0370300B1 (fr)	1994-04-06	Azolylméthyl-carbinoles substitués par un groupe cyclopropyle, procédé de préparation et leur application comme médicaments
EP0104300B1 (fr)	1986-03-26	Diazolyl-alcanoles, procédé pour leur préparation et leur utilisation comme agents antimycotiques
EP0011770B1 (fr)	1981-10-14	Fluorényl-azolylméthyl-carbinols, procédé pour leur préparation médicaments contenant ces composés et procédé pour la préparation de ces médicaments
EP0057863B1 (fr)	1984-06-13	Agent antimicrobien
EP0022969B1 (fr)	1983-05-25	Compositions antimycotiques contenant des azolylalcénols et leur préparation
EP0367069A2 (fr)	1990-05-09	Bisazoles substitués, procédé de préparation et leur application comme médicaments
EP0083750A1 (fr)	1983-07-20	Azolyl butanols antimycosiques
DE2832677A1 (de)	1980-02-07	Hydroxypropyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2705677A1 (de)	1978-08-17	2,4-dichlorphenyl-imidazolyl-aethanone(ole), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2820489A1 (de)	1979-11-15	Hydroxypropyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE3732387A1 (de)	1989-04-06	Azolylmethylcyclopropyl-derivate enthaltende antimykotische mittel
DE3019028A1 (de)	1981-11-26	Antimikrobielle mittel
EP0031883A1 (fr)	1981-07-15	Agent antimicrobien contenant des dérivés hydroxybutyl imidazoliques
DE2931756A1 (de)	1981-02-19	Antimikrobielle mittel

DD146824A5 - Verfahren zur herstellung von hydroxypropyl-triazolen - Google Patents

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