NO326366B1 - Imidazolderivater, farmasoytiske preparater inneholdende slike samt deres fremstilling - Google Patents

Imidazolderivater, farmasoytiske preparater inneholdende slike samt deres fremstilling Download PDF

Info

Publication number: NO326366B1
Authority: NO; Norway
Prior art keywords: group; compound; formula; salt; pyrrolo
Prior art date: 2000-11-17

Application number

NO20032234A

Other languages

English (en)

Norwegian (no)

Other versions

NO20032234L (no

NO20032234D0 (no

Inventor

Takenori Hitaka

Akihiro Tasaka

Isao Aoki

Nobuyuki Matsunaga

Masami Kusaka

Mari Adachi

Akio Ojida

Original Assignee

Takeda Pharmaceutical

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.)

2000-11-17

Filing date

2003-05-16

Publication date

2008-11-17

2003-05-16 Application filed by Takeda Pharmaceutical filed Critical Takeda Pharmaceutical

2003-05-16 Publication of NO20032234D0 publication Critical patent/NO20032234D0/no

2003-07-16 Publication of NO20032234L publication Critical patent/NO20032234L/no

2008-11-17 Publication of NO326366B1 publication Critical patent/NO326366B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 78
239000000825 pharmaceutical preparation Substances 0.000 title claims description 25
150000002460 imidazoles Chemical class 0.000 title description 4
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 266
150000003839 salts Chemical class 0.000 claims description 114
239000000203 mixture Substances 0.000 claims description 113
239000002253 acid Substances 0.000 claims description 45
238000000034 method Methods 0.000 claims description 41
125000005843 halogen group Chemical group 0.000 claims description 31
OZPFIJIOIVJZMN-UHFFFAOYSA-N 6-(7-hydroxy-5,6-dihydropyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthalenecarboxamide Chemical compound C1=CC2=CC(C(=O)NC)=CC=C2C=C1C1(O)C2=CN=CN2CC1 OZPFIJIOIVJZMN-UHFFFAOYSA-N 0.000 claims description 27
230000003287 optical effect Effects 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 16
239000003098 androgen Substances 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
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GIYVJBCEIATHSN-UHFFFAOYSA-N 7-[4-(4-fluorophenyl)phenyl]-5,6-dihydropyrrolo[1,2-c]imidazol-7-ol Chemical compound C1CN2C=NC=C2C1(O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 GIYVJBCEIATHSN-UHFFFAOYSA-N 0.000 claims description 10
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XPDAYTAXTQFSDQ-UHFFFAOYSA-N 6-(7-hydroxy-5,6-dihydropyrrolo[1,2-c]imidazol-7-yl)naphthalene-2-carboxamide Chemical compound C1=CC2=CC(C(=O)N)=CC=C2C=C1C1(O)C2=CN=CN2CC1 XPDAYTAXTQFSDQ-UHFFFAOYSA-N 0.000 claims description 8
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239000003446 ligand Substances 0.000 claims description 8
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238000007363 ring formation reaction Methods 0.000 claims description 3
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125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims 3
230000000259 anti-tumor effect Effects 0.000 claims 1
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MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 14
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Classifications

- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

NO20032234A 2000-11-17 2003-05-16 Imidazolderivater, farmasoytiske preparater inneholdende slike samt deres fremstilling NO326366B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2000351780		2000-11-17
JP2001247618		2001-08-17
JP2001336880		2001-11-01
PCT/JP2001/010002 WO2002040484A2 (en)	2000-11-17	2001-11-16	Novel imidazole derivatives, production method thereof and use thereof

Publications (3)

Publication Number	Publication Date
NO20032234D0 NO20032234D0 (no)	2003-05-16
NO20032234L NO20032234L (no)	2003-07-16
NO326366B1 true NO326366B1 (no)	2008-11-17

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Application Number	Title	Priority Date	Filing Date
NO20032234A NO326366B1 (no)	2000-11-17	2003-05-16	Imidazolderivater, farmasoytiske preparater inneholdende slike samt deres fremstilling

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US (1)	US7141598B2 (es)
EP (2)	EP1681290B9 (es)
JP (2)	JP3753971B2 (es)
KR (3)	KR20080002929A (es)
CN (3)	CN1900079A (es)
AR (1)	AR034854A1 (es)
AT (2)	ATE533768T1 (es)
AU (3)	AU1429602A (es)
BR (1)	BR0115306B1 (es)
CA (1)	CA2429133C (es)
CY (1)	CY1105423T1 (es)
DE (1)	DE60119963T2 (es)
DK (1)	DK1334106T3 (es)
ES (1)	ES2260303T3 (es)
HU (1)	HU229408B1 (es)
IL (2)	IL155624A0 (es)
MX (1)	MXPA03004347A (es)
MY (1)	MY134929A (es)
NO (1)	NO326366B1 (es)
NZ (1)	NZ526387A (es)
PE (1)	PE20020596A1 (es)
PL (1)	PL204934B1 (es)
PT (1)	PT1334106E (es)
SI (1)	SI1334106T1 (es)
TW (1)	TWI306099B (es)
WO (1)	WO2002040484A2 (es)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7662974B2 (en) *	2002-01-10	2010-02-16	Takeda Pharmaceutical Company Limited	Process for producing fused imidazole compound, reformatsky reagent in stable form, and process for producing the same
JP4745616B2 (ja) *	2003-02-26	2011-08-10	武田薬品工業株式会社	安定化されたイミダゾール誘導体含有医薬組成物、イミダゾール誘導体の安定化方法
WO2004075890A1 (ja) *	2003-02-26	2004-09-10	Takeda Pharmaceutical Company	安定化されたイミダゾール誘導体含有医薬組成物、イミダゾ－ル誘導体の安定化方法
EP1607092A4 (en) *	2003-03-17	2010-12-15	Takeda Pharmaceutical	COMPOSITIONS WITH CONTROLLED RELEASE
JP4837895B2 (ja) *	2003-03-17	2011-12-14	武田薬品工業株式会社	放出制御組成物
JP5070042B2 (ja) *	2004-05-03	2012-11-07	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	選択的アンドローゲン受容体モジュレーター（ｓａｒｍｓ）としての新規インドール化合物
JP5179174B2 (ja) *	2004-05-28	2013-04-10	ノバルティスファーマアーゲー	アルドステロンシンターゼ阻害剤としてのテトラヒドロ−イミダゾ［１，５−ａ］ピリジン誘導体
EP1854463A4 (en) *	2005-03-03	2011-03-23	Takeda Pharmaceutical	COMPOSITION WITH CONTROLLED RELEASE
GT200600381A (es)	2005-08-25	2007-03-28		Compuestos organicos
TW200804378A (en) *	2005-12-09	2008-01-16	Speedel Experimenta Ag	Organic compounds
EP1991223B1 (en) *	2006-02-10	2010-07-14	Janssen Pharmaceutica, N.V.	Novel imidazolopyrazole derivatives useful as selective androgen receptor modulators
AR060225A1 (es) *	2006-03-31	2008-06-04	Speedel Experimenta Ag	Proceso para preparar 6,7- dihidro-5h-imidazo (1,5-a) piridin -8- ona
PE20090931A1 (es) *	2007-10-29	2009-08-03	Takeda Pharmaceutical	Composicion farmaceutica que contiene un inhibidor de esteroide c17,20 liasa
TWI720517B (zh) *	2009-01-15	2021-03-01	美商英塞特公司	製造ｊａｋ抑制劑之方法及相關中間化合物
UY33740A (es) *	2010-11-18	2012-05-31	Takeda Pharmaceutical	Método para tratar el cáncer de mama y cáncer de ovarios
AR085743A1 (es)	2011-04-01	2013-10-23	Takeda Pharmaceutical	Preparacion solida
JP6082353B2 (ja)	2011-06-15	2017-02-15	武田薬品工業株式会社	イミダゾール誘導体の製造方法

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4728645A (en) *	1982-12-21	1988-03-01	Ciba-Geigy Corporation	Substituted imidazo[1,5-A]pyridine derivatives and other substituted bicyclic derivatives, useful as aromatase inhibitors
NZ221729A (en)	1986-09-15	1989-07-27	Janssen Pharmaceutica Nv	Imidazolyl methyl-substituted benzimidazole derivatives and pharmaceutical compositions
ZA882717B (en)	1987-04-22	1988-10-17	Merrell Dow Pharmaceuticals Inc.	17beta-(cyclopropylamino)-androst-5-eb-3beta-ol and related compounds useful as c17-20 lyase inhibitors
US5057521A (en) *	1988-10-26	1991-10-15	Ciba-Geigy Corporation	Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism
US4966898A (en)	1989-08-15	1990-10-30	Merrell Dow Pharmaceuticals Inc.	4-substituted 17β-(cyclopropylamino)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors
CA2104234A1 (en)	1991-03-01	1993-07-22	Denis R. Mckay	Powder coating method for producing circuit board laminae and the like
CA2127689A1 (en) *	1992-01-27	1993-08-05	Marcel A. C. Janssen	Pyrroloimidazolyl and imidazopyridinyl substituted 1h-benzimidazole derivatives as aromatase inhibitors
US5457102A (en) *	1994-07-07	1995-10-10	Janssen Pharmaceutica, N.V.	Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives
CA2132449C (en)	1992-03-31	2002-09-10	Susan E. Barrie	17 - substituted steroids useful in cancer treatment
GB9310635D0 (en)	1993-05-21	1993-07-07	Glaxo Group Ltd	Chemical compounds
WO1995009157A1 (en)	1993-09-30	1995-04-06	Yamanouchi Pharmaceutical Co., Ltd.	Azole derivative and pharmaceutical composition thereof
AU3846395A (en)	1994-11-07	1996-05-31	Janssen Pharmaceutica N.V.	Compositions comprising carbazoles and cyclodextrins
WO1997000257A1 (en)	1995-06-14	1997-01-03	Yamanouchi Pharmaceutical Co., Ltd.	Fused imidazole derivatives and medicinal composition thereof
WO1998037070A1 (en)	1997-02-21	1998-08-27	Takeda Chemical Industries, Ltd.	Fused ring compounds, process for producing the same and use thereof
DE69823222T2 (de)	1997-10-02	2005-04-14	Daiichi Pharmaceutical Co., Ltd.	Dihydronaphthalinderivate und verfahren zur herstellung derselben
EP1073640B1 (en)	1998-04-23	2005-04-13	Takeda Pharmaceutical Company Limited	Naphthalene derivatives, their production and use
PE20010781A1 (es) *	1999-10-22	2001-08-08	Takeda Chemical Industries Ltd	Compuestos 1-(1h-imidazol-4-il)-1-(naftil-2-sustituido)etanol, su produccion y utilizacion

2001
- 2001-11-16 PE PE2001001147A patent/PE20020596A1/es active IP Right Grant
- 2001-11-16 JP JP2001351035A patent/JP3753971B2/ja not_active Expired - Fee Related
- 2001-11-16 KR KR1020077025704A patent/KR20080002929A/ko not_active Withdrawn
- 2001-11-16 MX MXPA03004347A patent/MXPA03004347A/es active IP Right Grant
- 2001-11-16 CN CNA200610100666XA patent/CN1900079A/zh active Pending
- 2001-11-16 BR BRPI0115306-4B1A patent/BR0115306B1/pt not_active IP Right Cessation
- 2001-11-16 AT AT05077705T patent/ATE533768T1/de active
- 2001-11-16 DK DK01982800T patent/DK1334106T3/da active
- 2001-11-16 HU HU0400549A patent/HU229408B1/hu not_active IP Right Cessation
- 2001-11-16 WO PCT/JP2001/010002 patent/WO2002040484A2/en not_active Ceased
- 2001-11-16 KR KR1020057018247A patent/KR100809899B1/ko not_active Expired - Fee Related
- 2001-11-16 EP EP05077705.1A patent/EP1681290B9/en not_active Expired - Lifetime
- 2001-11-16 EP EP01982800A patent/EP1334106B1/en not_active Expired - Lifetime
- 2001-11-16 KR KR1020037006727A patent/KR100725442B1/ko not_active Expired - Fee Related
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- 2001-11-16 AU AU2002214296A patent/AU2002214296C1/en not_active Ceased
- 2001-11-16 ES ES01982800T patent/ES2260303T3/es not_active Expired - Lifetime
- 2001-11-16 PT PT01982800T patent/PT1334106E/pt unknown
2003
- 2003-04-28 IL IL155624A patent/IL155624A/en not_active IP Right Cessation
- 2003-05-16 NO NO20032234A patent/NO326366B1/no not_active IP Right Cessation
2005
- 2005-08-31 JP JP2005252651A patent/JP4427496B2/ja not_active Expired - Fee Related
- 2005-10-18 AU AU2005225035A patent/AU2005225035B2/en not_active Ceased
2006
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Also Published As

Publication number	Publication date
TWI306099B (en)	2009-02-11
PL204934B1 (pl)	2010-02-26
US7141598B2 (en)	2006-11-28
ATE533768T1 (de)	2011-12-15
JP2006045239A (ja)	2006-02-16
CN100572363C (zh)	2009-12-23
EP1334106B1 (en)	2006-05-24
HK1056168A1 (en)	2004-02-06
CN1329394C (zh)	2007-08-01
AR034854A1 (es)	2004-03-24
AU2002214296C1 (en)	2006-04-13
EP1681290B9 (en)	2013-06-19
CN1900079A (zh)	2007-01-24
SI1334106T1 (sl)	2006-10-31
JP2003201282A (ja)	2003-07-18
JP4427496B2 (ja)	2010-03-10
DE60119963T2 (de)	2006-10-05
BR0115306B1 (pt)	2013-12-24
HUP0400549A3 (en)	2004-09-28
AU1429602A (en)	2002-05-27
ES2260303T3 (es)	2006-11-01
EP1681290B1 (en)	2011-11-16
KR20050105287A (ko)	2005-11-03
PL362766A1 (en)	2004-11-02
CN1680336A (zh)	2005-10-12
EP1681290A2 (en)	2006-07-19
CY1105423T1 (el)	2010-04-28
US20040033935A1 (en)	2004-02-19
CN1474819A (zh)	2004-02-11
MXPA03004347A (es)	2004-05-04
DK1334106T3 (da)	2006-09-18
KR100725442B1 (ko)	2007-06-07
WO2002040484A2 (en)	2002-05-23
PE20020596A1 (es)	2002-08-13
AU2005225035A1 (en)	2005-11-10
CA2429133A1 (en)	2002-05-23
JP3753971B2 (ja)	2006-03-08
WO2002040484A3 (en)	2002-09-26
IL155624A (en)	2006-12-31
HUP0400549A2 (hu)	2004-06-28
ATE327237T1 (de)	2006-06-15
AU2002214296B2 (en)	2005-09-29
BR0115306A (pt)	2004-02-10
KR20030048156A (ko)	2003-06-18
KR100809899B1 (ko)	2008-03-10
CA2429133C (en)	2009-08-18
NO20032234L (no)	2003-07-16
NO20032234D0 (no)	2003-05-16
HU229408B1 (hu)	2013-12-30
EP1681290A3 (en)	2006-07-26
KR20080002929A (ko)	2008-01-04
AU2005225035B2 (en)	2007-02-22
IL155624A0 (en)	2003-11-23
MY134929A (en)	2008-01-31
NZ526387A (en)	2004-02-27
EP1334106A2 (en)	2003-08-13
PT1334106E (pt)	2006-08-31
DE60119963D1 (de)	2006-06-29

Legal Events

Date	Code	Title	Description
2020-06-22	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO326366B1 (no)	2008-11-17	Imidazolderivater, farmasoytiske preparater inneholdende slike samt deres fremstilling
EP2118111B1 (en)	2011-03-23	2-amin0-5, 7-dihydr0-6h- pyrrolo [3, 4-d] pyrimidine derivatives as hsp-90 inhibitors for treating cancer
EP1222174B1 (en)	2009-05-27	Imidazol-4-ylmethanols used as inhibitors of steroid c17-20 lyase
AU2002214296A1 (en)	2002-08-01	Novel imidazole derivatives, production method thereof and use thereof
HUP0300028A2 (en)	2003-05-28	Thienopyridine derivatives, their production and use and pharmaceutical compositions containing them
CA2429437A1 (en)	2002-05-23	Imidazole derivatives, process for their preparation and their use
JP2000007658A (ja)	2000-01-11	ナフタレン誘導体
HK1095589A (en)	2007-05-11	Imidazole derivatives, production method thereof and use thereof
JP2002080458A (ja)	2002-03-19	１−置換−１−（１ｈ−イミダゾール−４−イル）メタノール類
HK1056168B (en)	2006-12-08	Imidazole derivatives, production method thereof and use thereof
JP4121268B2 (ja)	2008-07-23	イミダゾール誘導体、その製造法および用途