SU1069625A3 - Способ получени азолов или их кислотно-аддитивных солей их стереоизомеров - Google Patents

Способ получени азолов или их кислотно-аддитивных солей их стереоизомеров Download PDF

Info

Publication number: SU1069625A3
Authority: SU; USSR - Soviet Union
Prior art keywords: phenyl; triazol; weight; ylmethyl; methyl
Prior art date: 1978-06-23

Application number

SU792782151A

Other languages

English (en)

Russian (ru)

Inventor

Херес Ян

Баккс Лео

Original Assignee

Жансен Фармасетика Н.В. (Фирма)

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.)

1978-06-23

Filing date

1979-06-22

Publication date

1984-01-23

1979-06-22 Application filed by Жансен Фармасетика Н.В. (Фирма) filed Critical Жансен Фармасетика Н.В. (Фирма)

1984-01-23 Application granted granted Critical

1984-01-23 Publication of SU1069625A3 publication Critical patent/SU1069625A3/ru

1992-11-09 Priority to LV920188A priority Critical patent/LV5017A3/xx

Links

239000002253 acid Substances 0.000 title claims description 14
150000003839 salts Chemical class 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims 3
150000003851 azoles Chemical class 0.000 title claims 2
125000000217 alkyl group Chemical group 0.000 claims abstract 6
125000003545 alkoxy group Chemical group 0.000 claims abstract 2
125000001544 thienyl group Chemical group 0.000 claims abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
150000002431 hydrogen Chemical group 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
-1 halothienyl Chemical group 0.000 abstract description 77
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 2
UGUAAAKGQBAZBF-UHFFFAOYSA-N 2-(1,3-dioxolan-4-yl)ethanesulfonic acid Chemical class OS(=O)(=O)CCC1COCO1 UGUAAAKGQBAZBF-UHFFFAOYSA-N 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000001188 haloalkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 49
239000000047 product Substances 0.000 description 42
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000003756 stirring Methods 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 18
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 17
239000000243 solution Substances 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
239000000284 extract Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 10
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 10
239000000706 filtrate Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
239000003480 eluent Substances 0.000 description 7
229960003742 phenol Drugs 0.000 description 7
239000001294 propane Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 5
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
239000002002 slurry Substances 0.000 description 5
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
206010018498 Goitre Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000005187 foaming Methods 0.000 description 4
201000003872 goiter Diseases 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000012360 testing method Methods 0.000 description 4
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 3
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000222122 Candida albicans Species 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000011097 chromatography purification Methods 0.000 description 3
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 3
235000013305 food Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 2
YLVPWIKFJKMMLW-UHFFFAOYSA-N 2-(4-nitrophenyl)-3-propyl-1h-1,2,4-triazole-5-thione Chemical compound CCCC1=NC(S)=NN1C1=CC=C([N+]([O-])=O)C=C1 YLVPWIKFJKMMLW-UHFFFAOYSA-N 0.000 description 2
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 2
JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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238000009835 boiling Methods 0.000 description 2
229940095731 candida albicans Drugs 0.000 description 2
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238000004090 dissolution Methods 0.000 description 2
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
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229910000027 potassium carbonate Inorganic materials 0.000 description 2
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239000000932 sedative agent Substances 0.000 description 2
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235000017557 sodium bicarbonate Nutrition 0.000 description 2
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238000011121 vaginal smear Methods 0.000 description 2
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CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
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DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
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UORNTHBBLYBAJJ-UHFFFAOYSA-N 2-piperazin-1-ylphenol Chemical compound OC1=CC=CC=C1N1CCNCC1 UORNTHBBLYBAJJ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
SLZLYALAAOOODU-UHFFFAOYSA-N 3-ethyl-2-(4-nitrophenyl)-1h-1,2,4-triazole-5-thione Chemical compound CCC1=NC(S)=NN1C1=CC=C([N+]([O-])=O)C=C1 SLZLYALAAOOODU-UHFFFAOYSA-N 0.000 description 1
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241000223229 Trichophyton rubrum Species 0.000 description 1
MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
201000003984 candidiasis Diseases 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
244000005706 microflora Species 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VDKZSHONJYADKP-UHFFFAOYSA-N n-phenylpiperazin-1-amine Chemical compound C1CNCCN1NC1=CC=CC=C1 VDKZSHONJYADKP-UHFFFAOYSA-N 0.000 description 1
NVPYANQPAZAYJA-UHFFFAOYSA-N n-phenylpyrazol-1-amine Chemical compound C1=CC=NN1NC1=CC=CC=C1 NVPYANQPAZAYJA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
229910001950 potassium oxide Inorganic materials 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SU792782151A 1978-06-23 1979-06-22 Способ получени азолов или их кислотно-аддитивных солей их стереоизомеров SU1069625A3 (ru)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
LV920188A LV5017A3 (lv)	1978-06-23	1992-11-09	Azolu vai to skabju-aditivo salu vai stereoizomeru iegusanas metode

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US91933378A	1978-06-23	1978-06-23

Publications (1)

Publication Number	Publication Date
SU1069625A3 true SU1069625A3 (ru)	1984-01-23

Family

ID=25441906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU792782151A SU1069625A3 (ru)	1978-06-23	1979-06-22	Способ получени азолов или их кислотно-аддитивных солей их стереоизомеров

Country Status (6)

Country	Link
KR (1)	KR820001889B1 (cs)
CS (1)	CS241468B2 (cs)
LV (1)	LV5017A3 (cs)
PL (1)	PL117988B1 (cs)
SU (1)	SU1069625A3 (cs)
ZA (1)	ZA793128B (cs)

1979
- 1979-06-13 KR KR7901926A patent/KR820001889B1/ko not_active Expired
- 1979-06-13 CS CS794087A patent/CS241468B2/cs unknown
- 1979-06-22 SU SU792782151A patent/SU1069625A3/ru active
- 1979-06-22 ZA ZA793128A patent/ZA793128B/xx unknown
- 1979-06-23 PL PL1979216555A patent/PL117988B1/pl unknown
1992
- 1992-11-09 LV LV920188A patent/LV5017A3/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Вейганд-Хильгетаг. Методы эксперимента в органической химии. М., Хими , 1968, с. 340. *

Also Published As

Publication number	Publication date
PL216555A1 (cs)	1980-03-24
LV5017A3 (lv)	1993-06-10
PL117988B1 (en)	1981-09-30
KR820001889B1 (ko)	1982-10-18
CS241468B2 (en)	1986-03-13
CS408779A2 (en)	1985-08-15
ZA793128B (en)	1981-02-25

Publication	Publication Date	Title
EP0006711B1 (en)	1983-10-26	Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1h-imidazoles and 1h-1,2,4-triazoles, processes for preparing them and compositions containing them
JP2574656B2 (ja)	1997-01-22	置換（４−フエニル−１−ピペラジニル）フエノール誘導体及びその製造方法
US4916134A (en)	1990-04-10	4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-azolylmethyl)-1,3-dioxolan-4-yl]me]phenyl]-1-piperazinyl]phenyl]triazolones
AU600107B2 (en)	1990-08-02	4-(4-(4-((2-(2,4-difluorophenyl)-2-(1h-azolylmethyl)-1,3- dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl) triazolones
FI62836C (fi)	1983-03-10	Foerfarande foer framstaellning av heterocykliska derivat av bakterier och svampar foerstoerande 1-(1,3-dioxolan-2-ylmetyl)-1h-imidazoler och -1h-1,2,4-triazoler
JPH05246999A (ja)	1993-09-24	置換フエニル誘導体
FI96031C (fi)	1996-04-25	Menetelmä terapeuttisesti aktiivisten 4-/4-/4-/4-/2-(2,4-difluorifenyyli)-2-(1H-atsolyylimetyyli)-1,3-dioksolan-4-yyli/metoksi/fenyyli/-1-piperatsinyyli/fenyylisubstituoitujen triatsolonien ja imidatsolonien valmistamiseksi
AU4361599A (en)	1999-11-29	Water soluble azoles as broad-spectrum antifungals
US4368200A (en)	1983-01-11	Heterocyclic derivatives of (4-phenyl-piperazine-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4490530A (en)	1984-12-25	Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1H-imidazoles and 1H-1,2,4-triazoles
SU1069625A3 (ru)	1984-01-23	Способ получени азолов или их кислотно-аддитивных солей их стереоизомеров
US4229460A (en)	1980-10-21	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazoles having antifungal and antibacterial properties
JP2000507275A (ja)	2000-06-13	真菌感染の治療剤としての新規なトリアゾール類
BG60430B2 (bg)	1995-03-31	Хетероциклични производни на (4-фенилпиперазин-1-ил-арилокси- метил-1,3-диоксолан-2-ил)-метил-1н-имидазоли и 1н-1,2,4-триа- золи,методи за тяхното получаване и състави,които ги съдържат
US4232034A (en)	1980-11-04	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
KR810000676B1 (ko)	1981-06-20	디옥소란의 헤테로 고리치환체 제조방법
JPH01211561A (ja)	1989-08-24	含窒素複素環基置換フエニルピペラジニルフエノール及びその製造方法
HU184845B (en)	1984-10-29	Process for producing 1-bracket-1,3-dioxol-2-nyl-methyl-bracket closed-1h-1,2,4-triazole derivatives