NO322386B1 - Interleukin-5-hemmende 6-azauracilderivater, sammensetninger inneholdende disse og fremgangsmater for deres fremstilling. - Google Patents

Interleukin-5-hemmende 6-azauracilderivater, sammensetninger inneholdende disse og fremgangsmater for deres fremstilling. Download PDF

Info

Publication number: NO322386B1
Authority: NO; Norway
Prior art keywords: mol; formula; solvent; evaporated; filtered
Prior art date: 1999-08-06

Application number

NO20020565A

Other languages

English (en)

Norwegian (no)

Other versions

NO20020565L (no

NO20020565D0 (no

Inventor

Eddy Jean Edgard Freyne

Jean Fernand Armand Lacrampe

Frederik Dirk Deroose

Jerome Michel Claude Fortin

Erwin Coesemans

Original Assignee

Janssen Pharmaceutica Nv

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.)

1999-08-06

Filing date

2002-02-05

Publication date

2006-09-25

2002-02-05 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2002-02-05 Publication of NO20020565D0 publication Critical patent/NO20020565D0/no

2002-03-26 Publication of NO20020565L publication Critical patent/NO20020565L/no

2006-09-25 Publication of NO322386B1 publication Critical patent/NO322386B1/no

Links

239000000203 mixture Substances 0.000 title claims description 232
238000000034 method Methods 0.000 title claims description 28
SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical class O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 14
108010002616 Interleukin-5 Proteins 0.000 title description 11
229940100602 interleukin-5 Drugs 0.000 title description 10
230000002401 inhibitory effect Effects 0.000 title description 3
102000000743 Interleukin-5 Human genes 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 178
239000000460 chlorine Substances 0.000 claims description 100
-1 hydroxy, mercapto Chemical class 0.000 claims description 84
125000000217 alkyl group Chemical group 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 17
239000002585 base Substances 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 14
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239000002253 acid Substances 0.000 claims description 13
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Health & Medical Sciences (AREA)
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Life Sciences & Earth Sciences (AREA)
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Animal Behavior & Ethology (AREA)
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Gynecology & Obstetrics (AREA)
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Ophthalmology & Optometry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Peptides Or Proteins (AREA)

NO20020565A 1999-08-06 2002-02-05 Interleukin-5-hemmende 6-azauracilderivater, sammensetninger inneholdende disse og fremgangsmater for deres fremstilling. NO322386B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP99870170		1999-08-06
EP99126035		1999-12-27
PCT/EP2000/007358 WO2001010866A1 (en)	1999-08-06	2000-07-31	Interleukin-5 inhibiting 6-azauracil derivatives

Publications (3)

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NO20020565D0 NO20020565D0 (no)	2002-02-05
NO20020565L NO20020565L (no)	2002-03-26
NO322386B1 true NO322386B1 (no)	2006-09-25

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NO20020565A NO322386B1 (no)	1999-08-06	2002-02-05	Interleukin-5-hemmende 6-azauracilderivater, sammensetninger inneholdende disse og fremgangsmater for deres fremstilling.

Country Status (30)

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US (1)	US6911444B2 (pl)
EP (1)	EP1206471B1 (pl)
JP (1)	JP2003506451A (pl)
KR (1)	KR100795484B1 (pl)
CN (1)	CN1188410C (pl)
AR (1)	AR025046A1 (pl)
AT (1)	ATE318811T1 (pl)
AU (1)	AU780047B2 (pl)
BG (1)	BG106367A (pl)
BR (1)	BR0013014A (pl)
CA (1)	CA2380759A1 (pl)
CO (1)	CO5050264A1 (pl)
CZ (1)	CZ2002356A3 (pl)
DE (1)	DE60026312T2 (pl)
EA (1)	EA004740B1 (pl)
EE (1)	EE200200057A (pl)
ES (1)	ES2260031T3 (pl)
HK (1)	HK1048634B (pl)
HR (1)	HRP20020096A2 (pl)
HU (1)	HUP0202692A3 (pl)
IL (1)	IL147976A0 (pl)
MX (1)	MXPA02001343A (pl)
MY (1)	MY133512A (pl)
NO (1)	NO322386B1 (pl)
NZ (1)	NZ516506A (pl)
PL (1)	PL353475A1 (pl)
SK (1)	SK1642002A3 (pl)
TR (1)	TR200200310T2 (pl)
TW (1)	TWI271404B (pl)
WO (1)	WO2001010866A1 (pl)

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Publication number	Priority date	Publication date	Assignee	Title
US7186855B2 (en)	2001-06-11	2007-03-06	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en)	2005-04-06	2011-11-01	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US6818787B2 (en)	2001-06-11	2004-11-16	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7183276B2 (en)	2002-02-28	2007-02-27	Takeda Pharmaceutical Company Limited	Azole compounds
WO2005116001A1 (en) *	2004-05-29	2005-12-08	7Tm Pharma A/S	Substituted thiazoleacetic as crth2 ligands
WO2010027762A1 (en)	2008-09-04	2010-03-11	Boehringer Ingelheim International Gmbh	Indolizine inhibitors of leukotriene production
JP4743340B1 (ja)	2009-10-28	2011-08-10	セントラル硝子株式会社	保護膜形成用薬液
EP2509975B1 (en)	2009-12-04	2014-04-23	Boehringer Ingelheim International GmbH	Benzimidazole inhibitors of leukotriene production
EP2606045B1 (en)	2010-08-16	2016-01-06	Boehringer Ingelheim International GmbH	Oxadiazole inhibitors of leukotriene production
EP2609092B1 (en)	2010-08-26	2015-04-01	Boehringer Ingelheim International GmbH	Oxadiazole inhibitors of leukotriene production
CA2812449A1 (en)	2010-09-23	2012-03-29	Boehringer Ingelheim International Gmbh	Oxadiazole inhibitors of leukotriene production
WO2012040137A1 (en)	2010-09-23	2012-03-29	Boehringer Ingelheim International Gmbh	Oxadiazole inhibitors of leukotriene production
WO2012058254A1 (en)	2010-10-29	2012-05-03	Boehringer Ingelheim International Gmbh	Benzimidazole inhibitors of leukotriene production
JP5789888B2 (ja)	2010-11-01	2015-10-07	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ロイコトリエン生成のベンゾイミダゾールインヒビター
US9073895B2 (en)	2010-12-16	2015-07-07	Boehringer Ingelheim International Gmbh	Biarylamide inhibitors of leukotriene production
AR089853A1 (es)	2012-02-01	2014-09-24	Boehringer Ingelheim Int	Inhibidores de oxadiazol de la produccion de leucotrienos para terapia de combinacion, composicion farmaceutica, uso

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US42416A (en) *		1864-04-19		Improvement in harvesters
US10177A (en) *		1853-11-01		Improved pen and pencil case
FR2476087A1 (fr) *	1980-02-18	1981-08-21	Roussel Uclaf	Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
CA1244024A (en)	1984-08-01	1988-11-01	Gustaaf M. Boeckx	.alpha.- ARYL-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN- 2(3H)-YL)BENZENEACETONITRILES
US4631278A (en)	1984-08-01	1986-12-23	Janssen Pharmaceutica N.V.	Anti-protozoal α-aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetonitrile derivatives, pharmaceutical compositions, and method of use therefor
GB8602342D0 (en)	1986-01-30	1986-03-05	Janssen Pharmaceutica Nv	5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones
PL337875A1 (en) *	1997-07-10	2000-09-11	Janssen Pharmaceutica Nv	Derivatives of 6-azauracil as il-5 inhibitors
ID24390A (id) *	1997-07-10	2000-07-13	Janssen Pharmaceutica Nv	Turunan-turunan 6-azaurasil penghambat il-5
EP0987265A1 (en)	1998-09-18	2000-03-22	Janssen Pharmaceutica N.V.	Interleukin-5 inhibiting 6-azauracil derivatives

2000
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- 2000-07-31 KR KR1020027000704A patent/KR100795484B1/ko not_active IP Right Cessation
- 2000-07-31 AU AU61609/00A patent/AU780047B2/en not_active Ceased
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2002
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Also Published As

Publication number	Publication date
HK1048634B (zh)	2005-09-30
HUP0202692A3 (en)	2003-01-28
HK1048634A1 (en)	2003-04-11
MXPA02001343A (es)	2002-07-22
CN1188410C (zh)	2005-02-09
CA2380759A1 (en)	2001-02-15
HRP20020096A2 (en)	2005-10-31
JP2003506451A (ja)	2003-02-18
DE60026312T2 (de)	2006-12-21
AR025046A1 (es)	2002-11-06
CN1368972A (zh)	2002-09-11
US6911444B2 (en)	2005-06-28
AU6160900A (en)	2001-03-05
KR100795484B1 (ko)	2008-01-16
EP1206471A1 (en)	2002-05-22
NZ516506A (en)	2004-02-27
EP1206471B1 (en)	2006-03-01
ES2260031T3 (es)	2006-11-01
IL147976A0 (en)	2002-09-12
KR20020012317A (ko)	2002-02-15
EE200200057A (et)	2003-04-15
NO20020565L (no)	2002-03-26
MY133512A (en)	2007-11-30
PL353475A1 (pl)	2003-11-17
BR0013014A (pt)	2002-04-16
US20030114453A1 (en)	2003-06-19
CZ2002356A3 (cs)	2002-06-12
AU780047B2 (en)	2005-02-24
DE60026312D1 (de)	2006-04-27
CO5050264A1 (es)	2001-06-27
BG106367A (bg)	2002-09-30
TWI271404B (en)	2007-01-21
EA200200232A1 (ru)	2002-08-29
SK1642002A3 (en)	2003-03-04
TR200200310T2 (tr)	2002-08-21
HUP0202692A2 (hu)	2002-12-28
WO2001010866A1 (en)	2001-02-15
ATE318811T1 (de)	2006-03-15
NO20020565D0 (no)	2002-02-05
EA004740B1 (ru)	2004-08-26

Legal Events

Date	Code	Title	Description
2010-03-01	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO322386B1 (no)	2006-09-25	Interleukin-5-hemmende 6-azauracilderivater, sammensetninger inneholdende disse og fremgangsmater for deres fremstilling.
AU769133B2 (en)	2004-01-15	Interleukin-5 inhibiting 6-azauracil derivatives
US6498158B1 (en)	2002-12-24	Il-5 inhibiting 6-azauracil derivatives
US6743792B2 (en)	2004-06-01	6-azauracil derivatives as IL-5 inhibitors
US6803364B1 (en)	2004-10-12	Il-5 inhibiting 6-azauracil derivatives
US6469001B1 (en)	2002-10-22	IL-5 inhibiting 6-azauracil derivatives
CZ457699A3 (cs)	2000-09-13	Deriváty 6-azauracilii jako IL-5 inhibitory, způsob jejich přípravy a farmaceutické prostředky
MXPA01006154A (en)	2001-12-13	Il-5 inhibiting 6-azauracil derivatives
MXPA00000362A (en)	2001-12-04	6-azauracil derivatives as il-5 inhibitors