LU86001A1 - Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide - Google Patents

Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide Download PDF

Info

Publication number: LU86001A1
Authority: LU; Luxembourg
Prior art keywords: compound; salt; free form; pharmaceutically acceptable; antifungal
Prior art date: 1984-07-13

Application number

LU86001A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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

1985-07-12

Publication date

1986-02-12

1985-07-12 Application filed by Sandoz Sa filed Critical Sandoz Sa

1986-02-12 Publication of LU86001A1 publication Critical patent/LU86001A1/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 27
230000000843 anti-fungal effect Effects 0.000 title claims description 8
229940121375 antifungal agent Drugs 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
230000000855 fungicidal effect Effects 0.000 title description 3
239000000417 fungicide Substances 0.000 title description 2
150000003839 salts Chemical class 0.000 claims description 22
238000000034 method Methods 0.000 claims description 8
150000004696 coordination complex Chemical class 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 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
ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 2-pyrrol-1-ylethanol Chemical compound OCCN1C=CC=C1 ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000126 substance 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
239000000203 mixture Substances 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
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 5
-1 propyl-1-methylethyl Chemical group 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
239000002253 acid Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
241000222122 Candida albicans Species 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
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
241000221577 Uromyces appendiculatus Species 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229940095731 candida albicans Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
UYXAHRLPUPVSNJ-UHFFFAOYSA-N sodium;2h-triazole Chemical compound [Na].C=1C=NNN=1 UYXAHRLPUPVSNJ-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
241000207875 Antirrhinum Species 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
241000895502 Blumeria graminis f. sp. tritici 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
206010017533 Fungal infection Diseases 0.000 description 1
241000208152 Geranium Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241001181537 Hemileia Species 0.000 description 1
241000282412 Homo Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 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
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 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
241000510929 Uncinula Species 0.000 description 1
206010046914 Vaginal infection Diseases 0.000 description 1
201000008100 Vaginitis Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000000699 topical effect Effects 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
150000003852 triazoles Chemical class 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)

LU86001A 1984-07-13 1985-07-12 Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide LU86001A1 (fr)

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
LU86001A1 true LU86001A1 (fr)	1986-02-12

Family

ID=6240558

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86001A LU86001A1 (fr)	1984-07-13	1985-07-12	Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide

Country Status (17)

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

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
NL8501962A (nl)	1986-02-03
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
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
1985-07-12	DT	Application date
1991-06-28	TA	Annual fee

Publication	Publication Date	Title
LU85066A1 (fr)	1984-05-10	Nouveaux derives de ethanol,leur preparation et leur utilisation comme fongicides
FR2542000A1 (fr)	1984-09-07	Nouveaux derives de l'ethanol, leur preparation et leur utilisation comme fongicides
LU85551A1 (fr)	1985-04-29	Nouveaux composes azoliques,leur preparation et leur utilisation comme antifongiques et fongicides
BE851310A (fr)	1977-08-10	Nouveaux derives de la tetrahydro-equinocandine b
KR880002275B1 (ko)	1988-10-21	트리아졸 유도체의 제조방법
CA2346562A1 (fr)	2000-04-06	Roue deformable non pneumatique
FR2496103A1 (fr)	1982-06-18	Nouveaux derives du benzopyranne et du benzothiopyranne, leur preparation et leur application comme medicaments
CA2474627C (en)	2009-09-22	R-(-)-1-[2-(7-chlorobenzo[b]thiophen-3-yl-methoxy)-2-(2,4-dichlorophenyl)-ethyl]-1h-imidazole
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
JPS6030673B2 (ja)	1985-07-17	抗かび活性を有するエテニルイミダゾ−ル誘導体、その製造法、およびそれを含む製薬組成物その製造に有用な中間物、およびこの中間物の製造法
EP1272485A1 (fr)	2003-01-08	Nouveaux derives de la 1,2,3,4-tetrahydroisoquinoleine, leur procede de preparation et leur application comme fongicides
LU86001A1 (fr)	1986-02-12	Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide
FR2587333A1 (fr)	1987-03-20	Nouveaux ethers allyliques bicycliques, leur preparation et leur utilisation comme anti-fongiques et fongicides
CH639075A5 (fr)	1983-10-31	Ethers dibenzyliques substitues actifs sur le plan therapeutique.
CA2346563C (fr)	2009-12-22	Nouveaux derives de la 2-[3-phenyl-2-propenyl]-1,2,3,4-tetrahydroisoquinoleine, leur procede de preparation et leur application comme fongicides
FR2582305A1 (fr)	1986-11-28	Nouveaux composes azoliques, leur preparation et leur utilisation comme antifongiques et fongicides
BE883665A (fr)	1980-10-01	Nouveaux derives du benzymidazole
FR2473041A1 (fr)	1981-07-10	2,3-dihydro-2-((1h-imidazol-1-yl)-methylene)-1h-inden-1-ones, a action antifongique et antibacterienne
WO1994000442A1 (fr)	1994-01-06	Aryl-1 (o-alcoxyphenyl-4 piperazinyl-1)-2, -3 ou -4 alcanols, leur procede de preparation et leur utilisation pour la preparation de medicaments
LU85451A1 (fr)	1985-04-17	Nouveaux derives de l'ethanol,leur preparation et leur utilisation comme fongicides
FR2462426A1 (fr)	1981-02-13	Nouveau derive de la 2-(1-naphtyl)piperidine, sa preparation et son application comme medicament
HU212458B (en)	1996-06-28	New silyloxypropane derivatives substituted with triazole or imidazole pharmaceutical compositions containing them and process for producing them
FR2460948A1 (fr)	1981-01-30	Nouveaux derives imidazolylethoxymethyliques du thiazole, utiles comme medicaments, leur procede de preparation et compositions therapeutiques les contenant
FR2473521A1 (fr)	1981-07-17	2,3-dihydro-3-(1h-imidazol-1-ylmethylene)-4h-1-benzo-thiopyran-4-ones, a action antifongique et antibacterienne
FR2797873A1 (fr)	2001-03-02	Nouveaux derives de la 2-(3-phenyl-2-propenyl)-1,2,3,4-tetra hydro-isoquinoleine, leur procede de preparation et leur application comme fongicides