SI9600165A - Process for preparation of biological active derivative of 1,2,4- triazole and intermediates useful in this process - Google Patents
Process for preparation of biological active derivative of 1,2,4- triazole and intermediates useful in this process Download PDFInfo
- Publication number
- SI9600165A SI9600165A SI9600165A SI9600165A SI9600165A SI 9600165 A SI9600165 A SI 9600165A SI 9600165 A SI9600165 A SI 9600165A SI 9600165 A SI9600165 A SI 9600165A SI 9600165 A SI9600165 A SI 9600165A
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- SI
- Slovenia
- Prior art keywords
- formula
- compound
- hydrazine
- reaction
- difluorophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title description 10
- 239000000543 intermediate Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229960004884 fluconazole Drugs 0.000 claims abstract description 33
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 28
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000011541 reaction mixture Substances 0.000 claims description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- -1 hydrazine compound Chemical class 0.000 claims description 21
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 150000003852 triazoles Chemical class 0.000 claims description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 12
- UAWABSHMGXMCRK-UHFFFAOYSA-L samarium(ii) iodide Chemical compound I[Sm]I UAWABSHMGXMCRK-UHFFFAOYSA-L 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002429 hydrazines Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 229910052772 Samarium Inorganic materials 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 5
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- HAPIXNBOBZHNCA-UHFFFAOYSA-N methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C(B2OC(C)(C)C(C)(C)O2)=C1 HAPIXNBOBZHNCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 abstract description 4
- 239000003429 antifungal agent Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 239000008346 aqueous phase Substances 0.000 description 25
- 239000012074 organic phase Substances 0.000 description 25
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 238000001819 mass spectrum Methods 0.000 description 20
- 238000004611 spectroscopical analysis Methods 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000012071 phase Substances 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 235000019253 formic acid Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 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 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- BGNUMRRZDHOIHK-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-hydrazinyl-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(O)(CNN)CN1C=NC=N1 BGNUMRRZDHOIHK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- RHBMIMKPFZLGSE-UHFFFAOYSA-N hydrazine;methanesulfonic acid Chemical compound NN.CS(O)(=O)=O RHBMIMKPFZLGSE-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
- C07C243/16—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C243/18—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9600165A SI9600165A (en) | 1996-05-21 | 1996-05-21 | Process for preparation of biological active derivative of 1,2,4- triazole and intermediates useful in this process |
| AT96941664T ATE242221T1 (de) | 1996-05-21 | 1996-12-20 | Verfahren zur herstellung biologisch aktiver derivate des 1,2,4-triazols und in diesem verfahren nuetzliche zwischenprodukte |
| UA98126691A UA64712C2 (en) | 1996-05-21 | 1996-12-20 | A method for preparing biologically active derivative of 1,2,3-triazole and intermediate compounds used in this method |
| AU10982/97A AU1098297A (en) | 1996-05-21 | 1996-12-20 | Process for preparing biologically active derivatives of 1,2,4-triazol and intermediaries useful in this process |
| DE69628597T DE69628597T2 (de) | 1996-05-21 | 1996-12-20 | Verfahren zur herstellung biologisch aktiver derivate des 1,2,4-triazols und in diesem verfahren nuetzliche zwischenprodukte |
| SI9630619T SI0967210T1 (en) | 1996-05-21 | 1996-12-20 | Process for preparing biologically active derivatives of 1,2,4-triazol and intermediaries useful in this process |
| PCT/ES1996/000245 WO1997044330A1 (es) | 1996-05-21 | 1996-12-20 | Procedimiento para la preparacion de derivados biologicamente activos de 1,2,4-triazol e intermedios utiles en este procedimiento |
| KR1019980709360A KR20000015811A (ko) | 1996-05-21 | 1996-12-20 | 1,2,4-트리아졸의 생물학적 활성 유도체의 제조방법 및 이 방법에 유용한 중간체 |
| EP96941664A EP0967210B1 (en) | 1996-05-21 | 1996-12-20 | Process for preparing biologically active derivatives of 1,2,4-triazol and intermediaries useful in this process |
| HU9903524A HU223570B1 (hu) | 1996-05-21 | 1996-12-20 | Eljárás 1,2,4-triazolszármazékok előállítására, intermedierjeik és előállításuk |
| RU98123117/04A RU2170736C2 (ru) | 1996-05-21 | 1996-12-20 | Способ получения 2-[2,4-дифторфенил]-1,3-бис[1н-1,2,4-триазол-1-ил]пропан-2-ола и его фармацевтически приемлемых солей |
| YU19097A YU19097A (sh) | 1996-05-21 | 1997-05-14 | Postupak za pripremanje biološki aktivnog derivata 1,2,4-triazola i intermedijera koji se koriste u tom postupku |
| HRP-9600165A HRP970271A2 (en) | 1996-05-21 | 1997-05-20 | Process for preparing biologically active derivatives of 1,2,4-triazol and intermediates used in this process |
| NO985408A NO985408L (no) | 1996-05-21 | 1998-11-20 | FremgangsmÕte for fremstilling av biologisk aktive derivater av 1,2,4,-triazol og anvendelige mellomprodukter i fremgangsmÕten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9600165A SI9600165A (en) | 1996-05-21 | 1996-05-21 | Process for preparation of biological active derivative of 1,2,4- triazole and intermediates useful in this process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI9600165A true SI9600165A (en) | 1997-12-31 |
Family
ID=20431850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9600165A SI9600165A (en) | 1996-05-21 | 1996-05-21 | Process for preparation of biological active derivative of 1,2,4- triazole and intermediates useful in this process |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0967210B1 (ru) |
| KR (1) | KR20000015811A (ru) |
| AT (1) | ATE242221T1 (ru) |
| AU (1) | AU1098297A (ru) |
| DE (1) | DE69628597T2 (ru) |
| HR (1) | HRP970271A2 (ru) |
| HU (1) | HU223570B1 (ru) |
| NO (1) | NO985408L (ru) |
| RU (1) | RU2170736C2 (ru) |
| SI (1) | SI9600165A (ru) |
| UA (1) | UA64712C2 (ru) |
| WO (1) | WO1997044330A1 (ru) |
| YU (1) | YU19097A (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100327818B1 (ko) * | 1999-04-16 | 2002-03-09 | 윤재승 | 플루코나졸의 제조방법 |
| KR100341688B1 (ko) * | 1999-04-16 | 2002-06-24 | 윤재승 | 플루코나졸의 제조방법 |
| AU2002328176A1 (en) * | 2002-08-26 | 2004-03-11 | Ranbaxy Laboratories Limited | Azole derivatives as antifungal agents |
| EP2984080B1 (en) | 2013-04-12 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Novel triazolinthione derivatives |
| BR102013027313B1 (pt) * | 2013-10-23 | 2019-06-18 | Iharabras S.A. Indústrias Químicas | Processo para a preparação seletiva de (1h-1,2,4-triazol-1-il) alcanóis, composto hidrazinil alcanol obtido por tal processo e seu uso |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2099818A (en) * | 1981-06-06 | 1982-12-15 | Pfizer Ltd | Triazoles |
| IT1249211B (it) * | 1990-06-08 | 1995-02-20 | Ind Chimica Srl | Processo per la preparazione di triazolil isopropanoli in particolare fluconazolo |
| CA2106032C (en) * | 1993-09-13 | 1995-11-07 | Gamini Weeratunga | Methods for the manufacture of fluconazole and forms thereof, intermediates useful in the manufacture thereof, and combinations comprising fluconazole |
| HU212424B (en) * | 1993-09-23 | 1996-06-28 | Richter Gedeon Vegyeszet | New propan-2-ol derivatives substituted with triazole or imidazole and process for producing them |
| GB9415544D0 (en) * | 1994-08-02 | 1994-09-21 | Zeneca Ltd | Chemical process and intermediates |
| GB9415617D0 (en) * | 1994-08-02 | 1994-09-21 | Zeneca Ltd | Pharmaceutical compound |
-
1996
- 1996-05-21 SI SI9600165A patent/SI9600165A/sl unknown
- 1996-12-20 RU RU98123117/04A patent/RU2170736C2/ru not_active IP Right Cessation
- 1996-12-20 UA UA98126691A patent/UA64712C2/uk unknown
- 1996-12-20 AT AT96941664T patent/ATE242221T1/de not_active IP Right Cessation
- 1996-12-20 DE DE69628597T patent/DE69628597T2/de not_active Expired - Fee Related
- 1996-12-20 AU AU10982/97A patent/AU1098297A/en not_active Abandoned
- 1996-12-20 WO PCT/ES1996/000245 patent/WO1997044330A1/es active IP Right Grant
- 1996-12-20 EP EP96941664A patent/EP0967210B1/en not_active Expired - Lifetime
- 1996-12-20 KR KR1019980709360A patent/KR20000015811A/ko not_active Application Discontinuation
- 1996-12-20 HU HU9903524A patent/HU223570B1/hu not_active IP Right Cessation
-
1997
- 1997-05-14 YU YU19097A patent/YU19097A/sh unknown
- 1997-05-20 HR HRP-9600165A patent/HRP970271A2/xx not_active Application Discontinuation
-
1998
- 1998-11-20 NO NO985408A patent/NO985408L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0967210A1 (en) | 1999-12-29 |
| ATE242221T1 (de) | 2003-06-15 |
| KR20000015811A (ko) | 2000-03-15 |
| HUP9903524A2 (hu) | 2000-02-28 |
| YU19097A (sh) | 1999-09-27 |
| HRP970271A2 (en) | 1998-04-30 |
| HUP9903524A3 (en) | 2001-12-28 |
| DE69628597D1 (de) | 2003-07-10 |
| NO985408L (no) | 1999-01-20 |
| EP0967210B1 (en) | 2003-06-04 |
| HU223570B1 (hu) | 2004-09-28 |
| NO985408D0 (no) | 1998-11-20 |
| UA64712C2 (en) | 2004-03-15 |
| AU1098297A (en) | 1997-12-09 |
| DE69628597T2 (de) | 2004-04-22 |
| RU2170736C2 (ru) | 2001-07-20 |
| WO1997044330A1 (es) | 1997-11-27 |
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