IE58516B1 - A 1,2,4-triazole derivative, its preparation and use as an anti-fungal - Google Patents

A 1,2,4-triazole derivative, its preparation and use as an anti-fungal

Info

Publication number: IE58516B1
Authority: IE; Ireland
Prior art keywords: compound; salt; compound according; metal; free form
Prior art date: 1984-07-13

Application number

IE174785A

Other languages

English (en)

Other versions

IE851747L (en

Original Assignee

Sandoy Ltd

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

1985-07-11

Publication date

1993-10-06

1985-07-11 Application filed by Sandoy Ltd filed Critical Sandoy Ltd

1986-01-13 Publication of IE851747L publication Critical patent/IE851747L/en

1993-10-06 Publication of IE58516B1 publication Critical patent/IE58516B1/en

Links

238000002360 preparation method Methods 0.000 title description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title description 2
230000000843 anti-fungal effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 23
230000001857 anti-mycotic effect Effects 0.000 claims abstract description 7
239000002543 antimycotic Substances 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims description 11
150000004696 coordination complex Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
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
239000008194 pharmaceutical composition Substances 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
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
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
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
239000012043 crude product Substances 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000012458 free base Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
241000233866 Fungi Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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 1
240000001436 Antirrhinum majus Species 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
241000895502 Blumeria graminis f. sp. tritici 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
241000221785 Erysiphales Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241001181537 Hemileia Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 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
241000220225 Malus Species 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 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
241000208181 Pelargonium Species 0.000 description 1
244000045930 Phaseolus coccineus Species 0.000 description 1
235000010632 Phaseolus coccineus 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
240000004808 Saccharomyces cerevisiae Species 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
239000004480 active ingredient Substances 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
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 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
239000003814 drug Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000000855 fungicidal effect Effects 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
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
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000012730 sustained-release form Substances 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

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)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IE174785A 1984-07-13 1985-07-11 A 1,2,4-triazole derivative, its preparation and use as an anti-fungal IE58516B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
IE851747L IE851747L (en)	1986-01-13
IE58516B1 true IE58516B1 (en)	1993-10-06

Family

ID=6240558

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE174785A IE58516B1 (en)	1984-07-13	1985-07-11	A 1,2,4-triazole derivative, its preparation and use as an anti-fungal

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
KR840001109B1 (ko) *	1979-11-13	1984-08-06	산도즈 리미티드	α-아릴-1H-1,2,4-트리아졸-1-에탄올의제조방법
CH647513A5 (de) *	1979-11-13	1985-01-31	Sandoz Ag	Triazol-derivate, deren herstellung und verwendung.
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 GB GB08517526A patent/GB2161483B/en not_active Expired
- 1985-07-11 SE SE8503443A patent/SE456679B/sv not_active IP Right Cessation
- 1985-07-11 IL IL75774A patent/IL75774A/xx not_active IP Right Cessation
- 1985-07-11 PH PH32517A patent/PH23287A/en unknown
- 1985-07-11 AU AU44779/85A patent/AU582761B2/en not_active Expired
- 1985-07-11 NZ NZ212718A patent/NZ212718A/xx unknown
- 1985-07-11 DK DK318185A patent/DK163058C/da not_active IP Right Cessation
- 1985-07-11 IE IE174785A patent/IE58516B1/en not_active IP Right Cessation
- 1985-07-12 LU LU86001A patent/LU86001A1/fr unknown
- 1985-07-12 JP JP60155017A patent/JPS6144878A/ja not_active Expired - Lifetime
- 1985-07-12 ZA ZA855286A patent/ZA855286B/xx unknown

Also Published As

Publication number	Publication date
DK163058C (da)	1992-06-09
DE3524296A1 (de)	1986-01-16
AU582761B2 (en)	1989-04-13
GB2161483B (en)	1988-07-13
NL8501962A (nl)	1986-02-03
IE851747L (en)	1986-01-13
NZ212718A (en)	1989-01-27
SE8503443L (sv)	1986-01-14
PH23287A (en)	1989-06-30
SE456679B (sv)	1988-10-24
IT8548324A0 (it)	1985-07-09
SE8503443D0 (sv)	1985-07-11
FR2567515A1 (fr)	1986-01-17
JPS6144878A (ja)	1986-03-04
DE3524296C2 (de)	1994-08-25
IL75774A (en)	1989-12-15
IL75774A0 (en)	1985-11-29
DK318185A (da)	1986-01-14
FR2567515B1 (fr)	1988-09-09
GB2161483A (en)	1986-01-15
IT1200087B (it)	1989-01-05
DK163058B (da)	1992-01-13
DK318185D0 (da)	1985-07-11
BE902837A (fr)	1986-01-09
AU4477985A (en)	1986-01-16
CH668772A5 (de)	1989-01-31
LU86001A1 (fr)	1986-02-12
GB8517526D0 (en)	1985-08-14
ZA855286B (en)	1987-02-25

Publication	Publication Date	Title
CA2285891C (en)	2004-01-06	Triazole antifungal agents
CA1128528A (en)	1982-07-27	Hydroxyethyl-azole compounds, their production and their medicinal use
CA1242723A (en)	1988-10-04	Azoles, processes for their preparation and their use
JPH0222731B2 (de)	1990-05-21
JPH10512599A (ja)	1998-12-02	治療において有用なトリアゾール誘導体
IE840393L (en)	1984-09-08	Anti fungal di(azolyl) propanol derivatives
FI71310C (fi)	1986-12-19	Foerfarande foer framstaellning av som laekemedel anvaenda imidazolylvinyletrar med baktericid och fungicid verkan
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
US4742077A (en)	1988-05-03	Bicyclic allylether derivatives, processes for their production and their use
JPH01250356A (ja)	1989-10-05	抗糸菌剤
IE58516B1 (en)	1993-10-06	A 1,2,4-triazole derivative, its preparation and use as an anti-fungal
US4783538A (en)	1988-11-08	Process for the preparation of optically active azolyl-carbinol derivatives, optically active 2-(4chloro-phenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol, prepared by this process and its use as an antimycotic
EP0113509B1 (de)	1987-03-04	1,3-Bis(triazolyl)-2-Amino-2-Aryl-Propan-Derivate, diese enthaltende pharmazeutische fungizide Zusammenstellungen
CA1232909A (en)	1988-02-16	1,2,4-triazolylpropanols, and their production and use
JP2987339B2 (ja)	1999-12-06	トリアゾール抗真菌性薬
JPS61271280A (ja)	1986-12-01	新規アゾ−ル誘導体、その製造方法と用途
US4461774A (en)	1984-07-24	Antifungal imidazolylcarboxylic acids and their derivatives
GB2175899A (en)	1986-12-10	Azole derivatives
JPS635390B2 (de)	1988-02-03
JPS6346075B2 (de)	1988-09-13
CZ291790B6 (cs)	2003-05-14	Azolová sloučenina, způsob výroby a farmaceutický prostředek
JPS5823396B2 (ja)	1983-05-14	１−エチル−アゾ−ル化合物の製造方法
KR830002278B1 (ko)	1983-10-21	하이드록시프로필-트리아졸 화합물의 제조방법
KR100248676B1 (ko)	2000-04-01	1-(아릴알킬-아미노알킬) 이미다졸 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물

Legal Events

Date	Code	Title	Description
2005-08-24	MK9A	Patent expired