NL8501962A - Nieuwe azolen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. - Google Patents

Nieuwe azolen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. Download PDF

Info

Publication number: NL8501962A
Authority: NL; Netherlands
Prior art keywords: compound; formula; salt; metal complex; enantiomer
Prior art date: 1984-07-13

Application number

NL8501962A

Other languages

English (en)

Dutch (nl)

Original Assignee

Sandoz 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.)

1984-07-13

Filing date

1985-07-09

Publication date

1986-02-03

1985-07-09 Application filed by Sandoz Ag filed Critical Sandoz Ag

1986-02-03 Publication of NL8501962A publication Critical patent/NL8501962A/nl

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title description 6
239000000825 pharmaceutical preparation Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 9
150000004696 coordination complex Chemical class 0.000 claims description 8
-1 1-cyclopropyl-1-methylethyl Chemical group 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
229940125758 compound 15 Drugs 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000004665 trialkylsilyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000001857 anti-mycotic effect Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QQCZXHWLXJBWJN-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(2-cyclopropylpropan-2-yl)oxirane Chemical compound C1OC1(C=1C=CC(Cl)=CC=1)C(C)(C)C1CC1 QQCZXHWLXJBWJN-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
239000002543 antimycotic Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
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
239000012071 phase Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
FEVALTJSQBFLEU-UHFFFAOYSA-N 1-methyl-4-methylsulfinylbenzene Chemical compound CC1=CC=C(S(C)=O)C=C1 FEVALTJSQBFLEU-UHFFFAOYSA-N 0.000 description 1
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
240000001436 Antirrhinum majus Species 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
240000007154 Coffea arabica Species 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241001181537 Hemileia Species 0.000 description 1
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
240000006240 Linum usitatissimum Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
244000141359 Malus pumila Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000208181 Pelargonium Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
241001337928 Podosphaera leucotricha Species 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241000221535 Pucciniales Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000510929 Uncinula Species 0.000 description 1
241000221576 Uromyces Species 0.000 description 1
241000221577 Uromyces appendiculatus Species 0.000 description 1
206010046914 Vaginal infection Diseases 0.000 description 1
201000008100 Vaginitis Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 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
- A61P31/10—Antimycotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8501962A 1984-07-13 1985-07-09 Nieuwe azolen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. NL8501962A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3425848		1984-07-13
DE3425848		1984-07-13

Publications (1)

Publication Number	Publication Date
NL8501962A true NL8501962A (nl)	1986-02-03

Family

ID=6240558

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8501962A NL8501962A (nl)	1984-07-13	1985-07-09	Nieuwe azolen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten.

Country Status (17)

Country	Link
JP (1)	JPS6144878A (de)
AU (1)	AU582761B2 (de)
BE (1)	BE902837A (de)
CH (1)	CH668772A5 (de)
DE (1)	DE3524296C2 (de)
DK (1)	DK163058C (de)
FR (1)	FR2567515B1 (de)
GB (1)	GB2161483B (de)
IE (1)	IE58516B1 (de)
IL (1)	IL75774A (de)
IT (1)	IT1200087B (de)
LU (1)	LU86001A1 (de)
NL (1)	NL8501962A (de)
NZ (1)	NZ212718A (de)
PH (1)	PH23287A (de)
SE (1)	SE456679B (de)
ZA (1)	ZA855286B (de)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH647513A5 (de) *	1979-11-13	1985-01-31	Sandoz Ag	Triazol-derivate, deren herstellung und verwendung.
JPS5697276A (en) *	1979-11-13	1981-08-05	Sandoz Ag	Alphaaaryll1hh1244triazolee11ethanols
ZA817473B (en) *	1980-11-19	1982-10-27	Ici Plc	Triazole and imidazole compounds
CH658654A5 (de) *	1983-03-04	1986-11-28	Sandoz Ag	Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten.

1985
- 1985-07-04 CH CH2871/85A patent/CH668772A5/de not_active IP Right Cessation
- 1985-07-06 DE DE3524296A patent/DE3524296C2/de not_active Expired - Lifetime
- 1985-07-08 FR FR8510531A patent/FR2567515B1/fr not_active Expired
- 1985-07-09 BE BE1/011292A patent/BE902837A/fr not_active IP Right Cessation
- 1985-07-09 NL NL8501962A patent/NL8501962A/nl active Search and Examination
- 1985-07-09 IT IT48324/85A patent/IT1200087B/it active
- 1985-07-11 AU AU44779/85A patent/AU582761B2/en not_active Expired
- 1985-07-11 GB GB08517526A patent/GB2161483B/en not_active Expired
- 1985-07-11 DK DK318185A patent/DK163058C/da not_active IP Right Cessation
- 1985-07-11 PH PH32517A patent/PH23287A/en unknown
- 1985-07-11 IL IL75774A patent/IL75774A/xx not_active IP Right Cessation
- 1985-07-11 IE IE174785A patent/IE58516B1/en not_active IP Right Cessation
- 1985-07-11 NZ NZ212718A patent/NZ212718A/xx unknown
- 1985-07-11 SE SE8503443A patent/SE456679B/sv not_active IP Right Cessation
- 1985-07-12 LU LU86001A patent/LU86001A1/fr unknown
- 1985-07-12 ZA ZA855286A patent/ZA855286B/xx unknown
- 1985-07-12 JP JP60155017A patent/JPS6144878A/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IT1200087B (it)	1989-01-05
IL75774A0 (en)	1985-11-29
CH668772A5 (de)	1989-01-31
DK318185D0 (da)	1985-07-11
AU582761B2 (en)	1989-04-13
ZA855286B (en)	1987-02-25
JPS6144878A (ja)	1986-03-04
IT8548324A0 (it)	1985-07-09
IE58516B1 (en)	1993-10-06
GB8517526D0 (en)	1985-08-14
GB2161483B (en)	1988-07-13
SE8503443L (sv)	1986-01-14
PH23287A (en)	1989-06-30
AU4477985A (en)	1986-01-16
NZ212718A (en)	1989-01-27
SE456679B (sv)	1988-10-24
IE851747L (en)	1986-01-13
DE3524296A1 (de)	1986-01-16
DE3524296C2 (de)	1994-08-25
SE8503443D0 (sv)	1985-07-11
GB2161483A (en)	1986-01-15
DK163058C (da)	1992-06-09
DK163058B (da)	1992-01-13
IL75774A (en)	1989-12-15
LU86001A1 (fr)	1986-02-12
BE902837A (fr)	1986-01-09
DK318185A (da)	1986-01-14
FR2567515A1 (fr)	1986-01-17
FR2567515B1 (fr)	1988-09-09

Legal Events

Date	Code	Title	Description
1992-09-01	BA	A request for search or an international-type search has been filed
1992-12-01	BB	A search report has been drawn up
1993-05-03	BC	A request for examination has been filed
1997-11-03	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: NOVARTIS AG
2001-10-01	BN	A decision not to publish the application has become irrevocable

Publication	Publication Date	Title
JPS6019894B2 (ja)	1985-05-18	抗菌剤
CA1215989A (en)	1986-12-30	Substituted 1-hydroxyethyl-triazolyl derivatives
IE840393L (en)	1984-09-08	Anti fungal di(azolyl) propanol derivatives
NZ207453A (en)	1987-09-30	1-phenyl-2-azole-ethylaminocarbonyl derivatives and pharmaceutical compositions
HU179415B (en)	1982-10-28	Process for producing hydroxy-ethyl-asole derivatives and pharmaceutical compositions containing them as active agents
HU179414B (en)	1982-10-28	Process for producing hydroxy-propyl-triasole derivatives and pharmaceutical compositions containing them as active agents
EP0096569A2 (de)	1983-12-21	Triazole mit pilztötender Wirkung
HU187750B (en)	1986-02-28	Process for preparing of imidazolyl-vinyl-ethers and medical preparatives containing these compounds
NL8402548A (nl)	1985-04-01	Nieuwe azoolverbindingen.
JPS611672A (ja)	1986-01-07	トリアゾール抗真菌薬
EP0107392A1 (de)	1984-05-02	Fungizide Triazole
CS221824B2 (en)	1983-04-29	Method of making the 1,1-diphenyl-2-/1,2,4-triazole-1-yl/-1-ethanole
IE56786B1 (en)	1991-12-18	Triazole antifungal agents
JPS59164782A (ja)	1984-09-17	置換１，３−ジアゾリル−２−プロパノ−ル類、その製法および抗糸状菌剤
EP0183494A2 (de)	1986-06-04	Triazol-Antifungal-Mittel
EP0195557A2 (de)	1986-09-24	Antifungale Triazole
NL8501962A (nl)	1986-02-03	Nieuwe azolen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten.
EP0049913A2 (de)	1982-04-21	Äthenylimidazol-Derivate, Verfahren zu deren Herstellung und deren pharmazeutische Zusammensetzungen, bei deren Herstellung verwendbare Zwischenprodukte und Verfahren zu deren Herstellung
EP0165775A1 (de)	1985-12-27	Fungizide Azol-Verbindungen
EP0126581A1 (de)	1984-11-28	Fungizide Triazolen-Derivate
JPH02172978A (ja)	1990-07-04	置換ビスアゾール、その製造方法およびその医薬としての使用
NO830655L (no)	1984-02-06	Diazolylalkanoler, fremgangsmaate til deres fremstilling og deres anvendelse som antimykotisk middel
CA1241961A (en)	1988-09-13	Antifungal triazole compound
EP0113509A2 (de)	1984-07-18	1,3-Bis(triazolyl)-2-Amino-2-Aryl-Propan-Derivate, diese enthaltende pharmazeutische fungizide Zusammenstellungen
IE831843L (en)	1984-02-07	Triazole antifungal agents.