DK176599B1 - Antifungalt middel, forbindelse til dette, fremgangsmåde til fremstilling af denne og metode til dets anvendelse - Google Patents

Antifungalt middel, forbindelse til dette, fremgangsmåde til fremstilling af denne og metode til dets anvendelse Download PDF

Info

Publication number: DK176599B1
Authority: DK; Denmark
Prior art keywords: compound; preparation; parts; formula; dichlorophenyl
Prior art date: 1995-07-08

Application number

DK199800013A

Other languages

Danish (da)

English (en)

Other versions

DK1398A (da

Inventor

Hiroki Kodama

Yoshimi Niwano

Kazuo Kanai

Mananori Yoshida

Original Assignee

Nihon Nohyaku Co 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.)

1995-07-08

Filing date

1998-01-07

Publication date

2008-10-27

1998-01-07 Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd

1998-01-07 Publication of DK1398A publication Critical patent/DK1398A/da

2008-10-27 Application granted granted Critical

2008-10-27 Publication of DK176599B1 publication Critical patent/DK176599B1/da

Links

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238000010189 synthetic method Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
229960002722 terbinafine Drugs 0.000 description 1
229930188428 trichomycin Natural products 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
210000005253 yeast cell Anatomy 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- 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
- 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

Landscapes

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

DK199800013A 1995-07-08 1998-01-07 Antifungalt middel, forbindelse til dette, fremgangsmåde til fremstilling af denne og metode til dets anvendelse DK176599B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP19617495		1995-07-08
JP19617495		1995-07-08
JP9601872		1996-07-05
PCT/JP1996/001872 WO1997002821A2 (fr)	1995-07-08	1996-07-05	Agent antifongique, son compose, son procede de production

Publications (2)

Publication Number	Publication Date
DK1398A DK1398A (da)	1998-01-07
DK176599B1 true DK176599B1 (da)	2008-10-27

Family

ID=16353435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK199800013A DK176599B1 (da)	1995-07-08	1998-01-07	Antifungalt middel, forbindelse til dette, fremgangsmåde til fremstilling af denne og metode til dets anvendelse

Country Status (21)

Country	Link
US (1)	US5900488A (fr)
EP (1)	EP0839035B1 (fr)
KR (1)	KR100386491B1 (fr)
CN (1)	CN1091596C (fr)
AT (1)	AT407832B (fr)
CA (1)	CA2226214C (fr)
CH (1)	CH692045A5 (fr)
DE (1)	DE19681478B4 (fr)
DK (1)	DK176599B1 (fr)
ES (1)	ES2137888B1 (fr)
FI (1)	FI119357B (fr)
GB (1)	GB2317615B (fr)
IL (1)	IL122618A (fr)
IN (1)	IN185384B (fr)
LU (1)	LU90190B1 (fr)
NO (1)	NO980055L (fr)
NZ (1)	NZ311796A (fr)
SE (1)	SE9800016L (fr)
TW (1)	TW450969B (fr)
WO (1)	WO1997002821A2 (fr)
ZA (1)	ZA965745B (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6127397A (en) *	1996-12-10	2000-10-03	Nihon Nohyaku Co., Ltd.	Optically active (R)-(E)-(4-substituted-phenyl-1,3-dithiolan-2-ylidene)-1-imidazolylaceto nitrile derivative, antifungal composition comprising the same, and method for producing the same
AU2003242235A1 (en) *	2002-06-18	2003-12-31	Pola Chemical Industries Inc.	Antifungal medicinal composition
CA2489854A1 (fr) *	2002-06-18	2003-12-24	Pola Chemical Industries Inc.	Composition medicinale fongicide
AU2006339842B2 (en) *	2006-03-08	2012-06-07	Nihon Nohyaku Co., Ltd.	Pharmaceutical composition for external use
NZ571818A (en) *	2006-03-08	2011-10-28	Nihon Nohyaku Co Ltd	External pharmaceutical composition comprising luliconazole and an alpha-hydroxycarboxylic acid such as lactic acid, glycolic acid or malic acid.
EP2005959B1 (fr) *	2006-03-08	2015-01-21	Nihon Nohyaku Co., Ltd.	Composition pharmaceutique pour l'usage externe
HUE029707T2 (en) *	2007-08-27	2017-03-28	Nihon Nohyaku Co Ltd	Anti-fungal dermatitis
CN101808638B (zh)	2007-09-05	2012-07-25	宝丽制药股份有限公司	抗真菌组合物
PL2191828T3 (pl)	2007-09-05	2017-02-28	Pola Pharma Inc.	Przeciwgrzybicza kompozycja farmaceutyczna
US20100204293A1 (en) *	2007-09-05	2010-08-12	Pola Pharma Inc.	Pharmaceutical composition
JP5654497B2 (ja)	2009-02-13	2015-01-14	トピカファーマシューティカルズ，インコーポレイテッド	抗真菌製剤
KR101409792B1 (ko)	2009-04-09	2014-06-19	니혼노야쿠가부시키가이샤	항진균성 약제학적 조성물
WO2010117089A2 (fr)	2009-04-09	2010-10-14	Pola Pharma Inc.	Composition pharmaceutique antimycotique
US8952044B2 (en) *	2009-08-25	2015-02-10	Pola Pharma Inc.	Antimycotic pharmaceutical composition
EP2579847A1 (fr) *	2010-06-11	2013-04-17	Pola Pharma Inc.	Composition pharmaceutique antimycosique
CN103012385B (zh) *	2012-02-17	2015-07-08	山东威智医药工业有限公司	卢立康唑的晶型及其制备方法
JP5460797B1 (ja)	2012-09-14	2014-04-02	株式会社ポーラファルマ	アミド誘導体及び安定性指標としてのその使用
CN104619703A (zh) *	2012-09-14	2015-05-13	宝丽制药股份有限公司	具有结晶习性的晶体以及通过对所述晶体进行加工获得的药物组合物
EP2895165B1 (fr) *	2012-09-14	2016-12-14	Pola Pharma Inc.	Cristal et préparation pharmaceutique le contenant
CN104619704B (zh) *	2012-09-14	2017-12-05	宝丽制药股份有限公司	表面自由能用于分化评价晶体的用途，基于表面自由能作为指标评价的晶体，以及通过包含所述晶体制备的药物组合物
WO2014115488A1 (fr) *	2013-01-28	2014-07-31	Pola Pharma Inc.	Composition pharmaceutique pour des maladies causées par des micro-organismes pathogènes tels que candida
EP2948145A1 (fr) *	2013-01-28	2015-12-02	Pola Pharma Inc.	Composition pharmaceutique destinées à des maladies provoquées par des microorganismes pathogènes tels qu'aspergillus
JP5589110B1 (ja)	2013-03-08	2014-09-10	株式会社ポーラファルマ	晶癖を有する結晶及び該結晶を有効成分として含有する医薬組成物
JP5680161B1 (ja)	2013-09-06	2015-03-04	株式会社ポーラファルマ	晶癖を有する結晶及び該結晶を有効成分として含有する医薬組成物
JP5587488B1 (ja)	2013-12-12	2014-09-10	株式会社ポーラファルマ	ルリコナゾールを含有する製剤の評価方法及び指標物質
WO2015162271A1 (fr) *	2014-04-25	2015-10-29	Syngenta Participations Ag	Dérivés imidazoliques microbicides
WO2016092478A1 (fr)	2014-12-12	2016-06-16	Glenmark Pharmaceuticals Limited	Procédé de préparation de luliconazole
WO2017108972A1 (fr)	2015-12-21	2017-06-29	Laboratorios Lesvi, S.L.	Composés de r-(-)-(e)-[4-(2,4-dichlorophényl)-1,3-dithiolan-2-ylidène]-1-imidazolylacétonitrile-ha (luliconazole-ha) à titre d'antifongiques
CN106008166B (zh) *	2016-05-17	2018-09-25	上海福乐医药科技有限公司	一种手性2-氯-1-(2,4-二氯苯基)乙醇的工业化生产方法
WO2018115319A2 (fr)	2016-12-23	2018-06-28	Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH)	Inhibiteurs de l'élément 1 de la sous-famille b de la famille 7 du cytochrome p450 (cyp7b1) destinés à être utilisés dans le traitement de maladies
TR201714882A2 (tr)	2017-10-03	2019-04-22	Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi	Luli̇konazolün topi̇kal farmasöti̇k kompozi̇syonlari
US10898470B1 (en)	2019-08-13	2021-01-26	Sato Pharmaceutical Co., Ltd.	Pharmaceutical composition containing antifungal agent as active ingredient
WO2023131969A1 (fr) *	2022-01-09	2023-07-13	Kimia Biosciences Limited	Procédé amélioré pour la préparation de luliconazole

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0218736B1 (fr) *	1985-10-10	1993-04-07	Nihon Nohyaku Co., Ltd.	Dérivé de cétène-S,S-acétal, procédé pour sa préparation et méthode pour guérir la mycose utilisant ce dérivé
DE3587252T2 (de) *	1985-10-09	1993-07-15	Nihon Nohyaku Co Ltd	Keten-s,s,-acetalderivate, verfahren zu ihrer herstellung und methode zur heilung von mykose unter verwendung dieser derivate.
JP3030780B2 (ja) *	1988-12-29	2000-04-10	日本農薬株式会社	光学活性なケテンジチオアセタール誘導体及びその製造方法
JPH0386337A (ja) *	1989-08-28	1991-04-11	Maeda Seisakusho:Kk	エクスパンディングチャックを用いた多重巻締め機および多重巻締め方法
CN1038247C (zh) *	1990-05-16	1998-05-06	云南省建筑材料科学研究设计院	一种新型磷石膏胶结料
JP3038519B2 (ja) *	1992-01-28	2000-05-08	日本農薬株式会社	創傷治癒促進剤

1996
- 1996-07-05 EP EP96922243A patent/EP0839035B1/fr not_active Expired - Lifetime
- 1996-07-05 CN CN96196659A patent/CN1091596C/zh not_active Expired - Lifetime
- 1996-07-05 AT AT0906196A patent/AT407832B/de not_active IP Right Cessation
- 1996-07-05 US US08/981,420 patent/US5900488A/en not_active Expired - Lifetime
- 1996-07-05 CA CA002226214A patent/CA2226214C/fr not_active Expired - Lifetime
- 1996-07-05 CH CH00023/98A patent/CH692045A5/de not_active IP Right Cessation
- 1996-07-05 ES ES009750013A patent/ES2137888B1/es not_active Expired - Fee Related
- 1996-07-05 WO PCT/JP1996/001872 patent/WO1997002821A2/fr not_active Ceased
- 1996-07-05 IL IL12261896A patent/IL122618A/en not_active IP Right Cessation
- 1996-07-05 IN IN1499DE1996 patent/IN185384B/en unknown
- 1996-07-05 NZ NZ311796A patent/NZ311796A/xx not_active IP Right Cessation
- 1996-07-05 KR KR10-1998-0700071A patent/KR100386491B1/ko not_active Expired - Lifetime
- 1996-07-05 DE DE19681478T patent/DE19681478B4/de not_active Expired - Lifetime
- 1996-07-05 GB GB9726766A patent/GB2317615B/en not_active Expired - Lifetime
- 1996-07-05 ZA ZA965745A patent/ZA965745B/xx unknown
- 1996-07-06 TW TW085108169A patent/TW450969B/zh not_active IP Right Cessation
1997
- 1997-12-31 LU LU90190A patent/LU90190B1/de active
1998
- 1998-01-06 NO NO980055A patent/NO980055L/no not_active Application Discontinuation
- 1998-01-07 DK DK199800013A patent/DK176599B1/da not_active IP Right Cessation
- 1998-01-07 SE SE9800016A patent/SE9800016L/xx not_active Application Discontinuation
- 1998-01-07 FI FI980023A patent/FI119357B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO980055D0 (no)	1998-01-06
EP0839035A2 (fr)	1998-05-06
CA2226214C (fr)	2007-04-17
FI980023A0 (fi)	1998-01-07
US5900488A (en)	1999-05-04
AU6319296A (en)	1997-02-10
WO1997002821A2 (fr)	1997-01-30
EP0839035B1 (fr)	2002-10-02
HK1009751A1 (en)	1999-06-11
ATA906196A (de)	2000-11-15
FI119357B (fi)	2008-10-31
ZA965745B (en)	1997-01-27
IL122618A0 (en)	1998-08-16
SE9800016D0 (sv)	1998-01-07
DE19681478B4 (de)	2006-09-21
GB2317615A (en)	1998-04-01
GB2317615B (en)	1998-09-02
FI980023L (fi)	1998-01-07
SE9800016L (sv)	1998-01-07
ES2137888B1 (es)	2001-01-01
NO980055L (no)	1998-03-06
KR19990028772A (ko)	1999-04-15
CN1091596C (zh)	2002-10-02
MX9710401A (es)	1998-07-31
WO1997002821A3 (fr)	1997-02-20
KR100386491B1 (ko)	2003-08-21
CA2226214A1 (fr)	1997-01-30
NZ311796A (en)	1999-06-29
CH692045A5 (de)	2002-01-15
ES2137888A1 (es)	1999-12-16
DE19681478T1 (de)	1998-07-02
CN1194582A (zh)	1998-09-30
AT407832B (de)	2001-06-25
IN185384B (fr)	2001-01-13
GB9726766D0 (en)	1998-02-18
LU90190B1 (de)	1998-03-02
TW450969B (en)	2001-08-21
IL122618A (en)	2002-07-25
AU697571B2 (en)	1998-10-08
DK1398A (da)	1998-01-07

Legal Events

Date	Code	Title	Description
2016-07-11	PUP	Patent expired	Expiry date: 20180107

Publication	Publication Date	Title
KR100386491B1 (ko)	2003-08-21	항진균제,이를위한화합물및이의제조방법
JP3278738B2 (ja)	2002-04-30	抗真菌剤
NO793674L (no)	1980-05-28	Hydroksyetyl-azoler, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel
SK48894A3 (en)	1995-02-08	Fungicidal trisubstituted tetrahydrofurans
PT100942B (pt)	1999-07-30	Agentes antifungicos de triazole, processo para a sua preparacao e composicoes farmaceuticas que os contem
NO793673L (no)	1980-05-28	Hydroksypropyl-triazoler, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel
HU188943B (en)	1986-05-28	Process for producing trizaole derivatives and o-esters or o-ethers thereof
HU195647B (en)	1988-06-28	Fungicide composition containing triazol derivatives and process for producing the active agents
CA2269617A1 (fr)	1998-05-22	Derives de 2r,4s,r,s et 2s,4r,r,s-hydroxyitraconazole et hydroxysaperconazole
WO1994014447A1 (fr)	1994-07-07	Procedes et compositions de (-) cetoconazole pour le traitement des champignons d'infections dues a des dermatophytes, des levures et des champignons
HU180630B (en)	1983-03-28	Process for preparing 1,1-diphenyl-2-/1,2,4-triazol-1-yl/-ethan-1-ols
US4554286A (en)	1985-11-19	Antifungal 1-triazolyl-2-aryl-3-(5-trifluoromethylimidazol-1-yl)propan-2-ol derivatives
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
US5135943A (en)	1992-08-04	1H-imidazole derivative compounds and pharmaceutical compositions containing the same
EP0370300A2 (fr)	1990-05-30	Azolylméthyl-carbinoles substitués par un groupe cyclopropyle, procédé de préparation et leur application comme médicaments
SK281688B6 (sk)	2001-06-11	Regioselektívny spôsob prípravy derivátov 1-(1,2,4-triazol-1-yl)-propan-2-olu
AU697571C (en)	1999-08-26	Antifungal agent, compound therefor, process for producing the same
HU186677B (en)	1985-09-30	Process for preparing substituted hydroxy-alkyl-imidazole and -triazole derivatives
MXPA97010401A (en)	1998-11-09	Antifungic agent, composed for the same, procedure for its production and method for suutilizac
DE3617190A1 (de)	1986-11-27	Neue azolderivate, verfahren zu ihrer herstellung und ihre verwendung
EP0848003B1 (fr)	2003-03-05	Dérivés de (R)-(E)-(4-substitué phenyl-1,3-dithiolan-2-ylidène)-1-imidazolylacetonitrile optiquement actifs et leur utilisation comme fongicides
US5051439A (en)	1991-09-24	Allylaminoethyltnazoles as fungicides and antimycotic agents
CN114736164B (zh)	2024-05-28	1，2，4-三氮唑苯甲酮类化合物或其可药用的盐及其应用
HU194215B (en)	1988-01-28	Process for preparing 2-/azolyl-methyl/-3-/difluor-benzyloxy/-2,3-dihydro-fluor-benzo /b/ thiophenes and pharmaceuticals comprising the same
JP2002179677A (ja)	2002-06-26	光学活性イミダゾリルアセトニトリル誘導体及びその製造方法