SK286156B6 - Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát - Google Patents

Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát Download PDF

Info

Publication number: SK286156B6
Authority: SK; Slovakia
Prior art keywords: formula; alkyl; group; radical; carbon atoms
Prior art date: 1998-05-14

Application number

SK1681-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK16812000A3 (sk

Inventor

Lieven Meerpoel

Leo Jacobus Jozef Backx

Der Veken Louis Jozef Elisabeth Van

Original Assignee

Janssen Pharmaceutica N. V.

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.)

1998-05-14

Filing date

1999-05-06

Publication date

2008-04-07

1999-05-06 Application filed by Janssen Pharmaceutica N. V. filed Critical Janssen Pharmaceutica N. V.

2001-08-06 Publication of SK16812000A3 publication Critical patent/SK16812000A3/sk

2008-04-07 Publication of SK286156B6 publication Critical patent/SK286156B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 52
239000003814 drug Substances 0.000 title claims abstract description 11
230000008569 process Effects 0.000 title claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
150000003851 azoles Chemical class 0.000 title abstract description 3
-1 1,2,3,4-tetrahydro-naphthalenyl Chemical group 0.000 claims abstract description 156
125000003118 aryl group Chemical group 0.000 claims abstract description 36
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
239000001257 hydrogen Substances 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 8
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000005940 1,4-dioxanyl group Chemical group 0.000 claims abstract description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 116
125000004432 carbon atom Chemical group C* 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 34
125000002883 imidazolyl group Chemical group 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 21
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239000002253 acid Substances 0.000 claims description 13
150000007980 azole derivatives Chemical class 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
206010017533 Fungal infection Diseases 0.000 claims description 10
208000031888 Mycoses Diseases 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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239000012442 inert solvent Substances 0.000 claims description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
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125000006239 protecting group Chemical group 0.000 claims description 5
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
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150000003335 secondary amines Chemical class 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
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125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
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125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
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125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000004306 triazinyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims 1
125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 15
150000002431 hydrogen Chemical group 0.000 abstract description 7
125000000815 N-oxide group Chemical group 0.000 abstract description 4
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 92
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150000003254 radicals Chemical class 0.000 description 33
239000002904 solvent Substances 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
229940121375 antifungal agent Drugs 0.000 description 27
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239000003480 eluent Substances 0.000 description 13
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125000004356 hydroxy functional group Chemical group O* 0.000 description 10
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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108010037444 diisopropylglutathione ester Proteins 0.000 description 9
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150000001721 carbon Chemical group 0.000 description 8
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238000003756 stirring Methods 0.000 description 7
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150000002170 ethers Chemical class 0.000 description 5
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Classifications

- 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
- 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
- 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
- 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
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Agricultural Chemicals And Associated Chemicals (AREA)

SK1681-2000A 1998-05-14 1999-05-06 Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát SK286156B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98201588A EP0957101A1 (en)	1998-05-14	1998-05-14	Water soluble azoles as broad-spectrum antifungals
PCT/EP1999/003242 WO1999058529A1 (en)	1998-05-14	1999-05-06	Water soluble azoles as broad-spectrum antifungals

Publications (2)

Publication Number	Publication Date
SK16812000A3 SK16812000A3 (sk)	2001-08-06
SK286156B6 true SK286156B6 (sk)	2008-04-07

Family

ID=8233724

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SK1681-2000A SK286156B6 (sk)	1998-05-14	1999-05-06	Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát
SK1682-2000A SK285763B6 (sk)	1998-05-14	1999-05-06	Azol, spôsob jeho prípravy a medziprodukt na jehoprípravu, jeho použitie a farmaceutický prostriedok s jeho obsahom

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SK1682-2000A SK285763B6 (sk)	1998-05-14	1999-05-06	Azol, spôsob jeho prípravy a medziprodukt na jehoprípravu, jeho použitie a farmaceutický prostriedok s jeho obsahom

Country Status (31)

Country	Link
US (2)	US6384030B1 (pl)
EP (3)	EP0957101A1 (pl)
JP (2)	JP2002514645A (pl)
KR (2)	KR100575147B1 (pl)
CN (2)	CN1137118C (pl)
AR (2)	AR016480A1 (pl)
AT (2)	ATE221884T1 (pl)
AU (2)	AU758876B2 (pl)
BG (2)	BG64388B1 (pl)
BR (2)	BR9911057A (pl)
CA (2)	CA2331187C (pl)
CO (1)	CO5021227A1 (pl)
CZ (2)	CZ298702B6 (pl)
DE (2)	DE69907171T2 (pl)
DK (1)	DK1077976T3 (pl)
EE (2)	EE04311B1 (pl)
ES (2)	ES2198915T3 (pl)
HR (2)	HRP20000741B1 (pl)
HU (2)	HUP0102031A3 (pl)
IL (2)	IL139647A0 (pl)
MY (2)	MY120248A (pl)
NO (2)	NO319851B1 (pl)
NZ (2)	NZ507965A (pl)
PL (2)	PL194086B1 (pl)
PT (1)	PT1077976E (pl)
SI (1)	SI1077976T1 (pl)
SK (2)	SK286156B6 (pl)
TR (2)	TR200003322T2 (pl)
TW (2)	TWI259835B (pl)
WO (2)	WO1999058529A1 (pl)
ZA (2)	ZA200007173B (pl)

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EP0957101A1 (en) *	1998-05-14	1999-11-17	Janssen Pharmaceutica N.V.	Water soluble azoles as broad-spectrum antifungals
NZ521241A (en) *	2000-03-07	2004-02-27	Ranbaxy Lab Ltd	Azole compounds as therapeutic agents for fungal infections
EP1413301A1 (fr) *	2002-10-24	2004-04-28	Bayer CropScience SA	Médicaments antifongiques à base de dérivés d'arylamidine
ITMI20032020A1 (it)	2003-10-17	2005-04-18	Italfarmaco Spa	Nuovi agenti antifungini azolici con diminuita interazione con i citocromi metabolici
AR052342A1 (es) *	2004-12-21	2007-03-14	Janssen Pharmaceutica Nv	Derivados sustituidos de triazolona,tetrazolona e imidazolona con actividad selectiva antagonista de alfa2c-adenoreceptores
BR112012029227B1 (pt) *	2010-05-19	2020-01-07	Sandoz Ag	Processo para a preparação de um composto quiral, composto quiral e uso de um composto
US9346791B2 (en)	2011-09-07	2016-05-24	The Johns Hopkins University	Itraconazole analogs and use thereof
US11028078B2 (en)	2011-09-07	2021-06-08	The Johns Hopkins University	Itraconazole analogs and use thereof
CA2913634C (en) *	2013-06-07	2022-08-09	The California Institute For Biomedical Research	Small molecule inhibitors of fibrosis
JP6669751B2 (ja)	2014-12-05	2020-03-18	プルモシデリミテド	抗真菌化合物
CA2968874C (en) *	2014-12-10	2024-06-18	The California Institute For Biomedical Research	Small molecule inhibitors of fibrosis
WO2016185225A1 (en) *	2015-05-21	2016-11-24	Pulmocide Limited	Antifungal 4-(4-(4-(((3r,5r)-5-((1 h -1,2,4-triazol-1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)- 3-methylphenyl)piperazin-1 -yl )-n -(2-h yd roxycyc lo h exyl) b e nzam i d e, or a pharmaceutically acceptable salt thereof.
CN105237392B (zh) *	2015-11-24	2017-12-12	辽宁渤大化工有限公司	芳烷基水杨酸及其衍生物的制备方法
WO2019040363A1 (en) *	2017-08-20	2019-02-28	University Of Connecticut	Azole analogues and methods of use thereof
WO2021030174A1 (en)	2019-08-09	2021-02-18	University Of Connecticut	Truncated itraconazole analogues and methods of use thereof
GB201917867D0 (en)	2019-12-06	2020-01-22	Pulmocide Ltd	Polymorphs
CN111138421A (zh) *	2019-12-26	2020-05-12	上海英诺富成生物科技有限公司	抗真菌水溶性化合物及其制备方法与应用

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US4267179A (en) *	1978-06-23	1981-05-12	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
DK0631578T3 (da) *	1992-03-18	2001-08-27	Janssen Pharmaceutica Nv	Itraconazol- og saperconazol-stereoisomerer
HU225062B1 (en) *	1993-12-21	2006-05-29	Schering Corp	Tetrahydrofuran derivatives with antifungal- effect, pharmaceutical compositions containing them and process for their preparation
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CZ59497A3 (en) *	1995-06-02	1997-08-13	Schering Corp	Tetrahydrofuran derivative and pharmaceutical composition containing thereof
ES2203707T3 (es) *	1995-06-19	2004-04-16	Schering Corporation	Antifungicos de tetrahidrofurano.
ATE270290T1 (de) *	1997-02-11	2004-07-15	Janssen Pharmaceutica Nv	Azole enthaltende antifungale aminosäure-ester
EP0957101A1 (en) *	1998-05-14	1999-11-17	Janssen Pharmaceutica N.V.	Water soluble azoles as broad-spectrum antifungals

1998
- 1998-05-14 EP EP98201588A patent/EP0957101A1/en not_active Withdrawn
1999
- 1999-05-06 NZ NZ507965A patent/NZ507965A/en not_active IP Right Cessation
- 1999-05-06 HR HR20000741A patent/HRP20000741B1/xx not_active IP Right Cessation
- 1999-05-06 TR TR2000/03322T patent/TR200003322T2/xx unknown
- 1999-05-06 ES ES99924942T patent/ES2198915T3/es not_active Expired - Lifetime
- 1999-05-06 TR TR2000/03323T patent/TR200003323T2/xx unknown
- 1999-05-06 DE DE69907171T patent/DE69907171T2/de not_active Expired - Lifetime
- 1999-05-06 CA CA002331187A patent/CA2331187C/en not_active Expired - Fee Related
- 1999-05-06 CN CNB998059560A patent/CN1137118C/zh not_active Expired - Fee Related
- 1999-05-06 KR KR1020007011624A patent/KR100575147B1/ko not_active Expired - Fee Related
- 1999-05-06 DE DE69902461T patent/DE69902461T2/de not_active Expired - Lifetime
- 1999-05-06 PT PT99926304T patent/PT1077976E/pt unknown
- 1999-05-06 BR BR9911057-1A patent/BR9911057A/pt not_active Application Discontinuation
- 1999-05-06 AU AU43615/99A patent/AU758876B2/en not_active Ceased
- 1999-05-06 AT AT99926304T patent/ATE221884T1/de active
- 1999-05-06 HU HU0102031A patent/HUP0102031A3/hu unknown
- 1999-05-06 US US09/700,251 patent/US6384030B1/en not_active Expired - Lifetime
- 1999-05-06 NZ NZ507966A patent/NZ507966A/xx not_active IP Right Cessation
- 1999-05-06 PL PL99344037A patent/PL194086B1/pl unknown
- 1999-05-06 IL IL13964799A patent/IL139647A0/xx not_active IP Right Cessation
- 1999-05-06 PL PL99344047A patent/PL194085B1/pl unknown
- 1999-05-06 SK SK1681-2000A patent/SK286156B6/sk not_active IP Right Cessation
- 1999-05-06 KR KR1020007009640A patent/KR100593395B1/ko not_active Expired - Fee Related
- 1999-05-06 HU HU0103536A patent/HUP0103536A3/hu unknown
- 1999-05-06 CZ CZ20004109A patent/CZ298702B6/cs not_active IP Right Cessation
- 1999-05-06 CN CNB998060690A patent/CN1135229C/zh not_active Expired - Fee Related
- 1999-05-06 AT AT99924942T patent/ATE238296T1/de not_active IP Right Cessation
- 1999-05-06 CA CA002331141A patent/CA2331141C/en not_active Expired - Fee Related
- 1999-05-06 EP EP99924942A patent/EP1077975B1/en not_active Expired - Lifetime
- 1999-05-06 BR BR9910448-2A patent/BR9910448A/pt not_active Application Discontinuation
- 1999-05-06 WO PCT/EP1999/003242 patent/WO1999058529A1/en not_active Ceased
- 1999-05-06 HR HR20000740A patent/HRP20000740B1/xx not_active IP Right Cessation
- 1999-05-06 EE EEP200000657A patent/EE04311B1/xx not_active IP Right Cessation
- 1999-05-06 JP JP2000548333A patent/JP2002514645A/ja active Pending
- 1999-05-06 CZ CZ20004108A patent/CZ299481B6/cs not_active IP Right Cessation
- 1999-05-06 DK DK99926304T patent/DK1077976T3/da active
- 1999-05-06 WO PCT/EP1999/003243 patent/WO1999058530A1/en not_active Ceased
- 1999-05-06 US US09/700,166 patent/US6448244B1/en not_active Expired - Lifetime
- 1999-05-06 SK SK1682-2000A patent/SK285763B6/sk not_active IP Right Cessation
- 1999-05-06 AU AU41417/99A patent/AU751135B2/en not_active Ceased
- 1999-05-06 JP JP2000548334A patent/JP2002514646A/ja active Pending
- 1999-05-06 EE EEP200000651A patent/EE04346B1/xx not_active IP Right Cessation
- 1999-05-06 ES ES99926304T patent/ES2182531T3/es not_active Expired - Lifetime
- 1999-05-06 IL IL13964999A patent/IL139649A/en not_active IP Right Cessation
- 1999-05-06 SI SI9930131T patent/SI1077976T1/xx unknown
- 1999-05-06 EP EP99926304A patent/EP1077976B1/en not_active Expired - Lifetime
- 1999-05-10 TW TW088107505A patent/TWI259835B/zh not_active IP Right Cessation
- 1999-05-10 TW TW088107504A patent/TW572899B/zh not_active IP Right Cessation
- 1999-05-11 MY MYPI99001861A patent/MY120248A/en unknown
- 1999-05-11 MY MYPI99001862A patent/MY122147A/en unknown
- 1999-05-13 CO CO99029778A patent/CO5021227A1/es unknown
- 1999-05-13 AR ARP990102270A patent/AR016480A1/es active IP Right Grant
- 1999-05-13 AR ARP990102276A patent/AR016482A1/es active IP Right Grant
2000
- 2000-08-28 BG BG104717A patent/BG64388B1/bg unknown
- 2000-11-09 BG BG104933A patent/BG64954B1/bg unknown
- 2000-11-13 NO NO20005712A patent/NO319851B1/no not_active IP Right Cessation
- 2000-11-13 NO NO20005713A patent/NO319760B1/no not_active IP Right Cessation
- 2000-12-04 ZA ZA200007173A patent/ZA200007173B/en unknown
- 2000-12-13 ZA ZA200007459A patent/ZA200007459B/xx unknown

Also Published As

Publication number	Publication date
SK16812000A3 (sk)	2001-08-06
CZ299481B6 (cs)	2008-08-13
NO20005712L (no)	2000-12-07
HRP20000741B1 (hr)	2009-02-28
BG104717A (en)	2001-07-31
PL194086B1 (pl)	2007-04-30
IL139649A (en)	2004-09-27
ZA200007459B (en)	2002-09-13
KR20010042852A (ko)	2001-05-25
PL344047A1 (en)	2001-09-24
NZ507966A (en)	2002-10-25
CZ20004108A3 (en)	2001-05-16
PL194085B1 (pl)	2007-04-30
HK1032781A1 (en)	2001-08-03
CN1137118C (zh)	2004-02-04
MY122147A (en)	2006-03-31
PT1077976E (pt)	2002-12-31
NO20005712D0 (no)	2000-11-13
AU751135B2 (en)	2002-08-08
NO20005713D0 (no)	2000-11-13
MY120248A (en)	2005-09-30
JP2002514645A (ja)	2002-05-21
HUP0103536A3 (en)	2002-08-28
CZ20004109A3 (en)	2001-05-16
HRP20000740A2 (en)	2001-10-31
CN1300288A (zh)	2001-06-20
NZ507965A (en)	2002-05-31
BG104933A (en)	2001-10-31
DK1077976T3 (da)	2002-12-02
TR200003322T2 (tr)	2001-02-21
HRP20000740B1 (en)	2003-12-31
CA2331141C (en)	2008-10-28
KR100593395B1 (ko)	2006-06-28
SK16822000A3 (sk)	2001-07-10
TW572899B (en)	2004-01-21
BG64954B1 (bg)	2006-10-31
JP2002514646A (ja)	2002-05-21
WO1999058530A1 (en)	1999-11-18
AR016482A1 (es)	2001-07-04
EP1077976B1 (en)	2002-08-07
IL139647A0 (en)	2002-02-10
EP1077975B1 (en)	2003-04-23
EE04311B1 (et)	2004-06-15
ES2182531T3 (es)	2003-03-01
WO1999058529A1 (en)	1999-11-18
US6384030B1 (en)	2002-05-07
CN1300287A (zh)	2001-06-20
AR016480A1 (es)	2001-07-04
NO319760B1 (no)	2005-09-12
BR9910448A (pt)	2001-01-02
HUP0102031A3 (en)	2002-10-28
BR9911057A (pt)	2001-02-06
KR100575147B1 (ko)	2006-05-03
TWI259835B (en)	2006-08-11
DE69907171D1 (de)	2003-05-28
HK1033312A1 (en)	2001-08-24
HUP0102031A2 (hu)	2002-05-29
AU4141799A (en)	1999-11-29
HRP20000741A2 (en)	2001-06-30
DE69902461T2 (de)	2003-04-10
AU4361599A (en)	1999-11-29
TR200003323T2 (tr)	2001-02-21
EP0957101A1 (en)	1999-11-17
ZA200007173B (en)	2002-03-04
DE69907171T2 (de)	2004-02-05
IL139649A0 (en)	2002-02-10
NO20005713L (no)	2001-01-11
KR20010041480A (ko)	2001-05-25
SI1077976T1 (en)	2003-02-28
EP1077975A1 (en)	2001-02-28
PL344037A1 (en)	2001-09-24
EP1077976A1 (en)	2001-02-28
HUP0103536A2 (hu)	2002-07-29
DE69902461D1 (de)	2002-09-12
ES2198915T3 (es)	2004-02-01
EE200000657A (et)	2002-04-15
CZ298702B6 (cs)	2007-12-27
ATE221884T1 (de)	2002-08-15
CA2331187C (en)	2008-11-18
US6448244B1 (en)	2002-09-10
ATE238296T1 (de)	2003-05-15
CO5021227A1 (es)	2001-03-27
NO319851B1 (no)	2005-09-19
CA2331187A1 (en)	1999-11-18
EE200000651A (et)	2002-04-15
BG64388B1 (bg)	2004-12-30
CN1135229C (zh)	2004-01-21
EE04346B1 (et)	2004-08-16
SK285763B6 (sk)	2007-07-06
CA2331141A1 (en)	1999-11-18
AU758876B2 (en)	2003-04-03

Publication	Publication Date	Title
SK286156B6 (sk)	2008-04-07	Azolový derivát, spôsob prípravy tohto azolového derivátu, použitie tohto azolového derivátu na výrobu liečiva a farmaceutická kompozícia obsahujúca tento azolový derivát
EP1177192B1 (en)	2003-03-19	Antifungal ethers
HK1033312B (en)	2003-02-21	Water soluble azoles as broad-spectrum antifungals
MXPA00011155A (es)	2001-07-31	Azoles solubles en agua como antifungicos de amplio espectro
HK1032781B (en)	2003-08-15	Water soluble azoles as broad-spectrum antifungals
MXPA00011152A (en)	2001-07-31	Water soluble azoles as broad-spectrum antifungals

Legal Events

Date	Code	Title	Description
2010-02-08	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20090506