NO321334B1 - 5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. - Google Patents

5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. Download PDF

Info

Publication number: NO321334B1
Authority: NO; Norway
Prior art keywords: methyl; phenyl; trifluoromethyl; bis; benzyl
Prior art date: 1999-05-31

Application number

NO20015701A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015701L (no

NO20015701D0 (no

Inventor

Heinz Stadler

Walter Hunkeler

Thierry Godel

Torsten Hoffmann

Patrick Schnider

Michael Boes

Guido Galley

Original Assignee

Hoffmann La Roche

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.)

1999-05-31

Filing date

2001-11-22

Publication date

2006-04-24

2001-11-22 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2001-11-22 Publication of NO20015701L publication Critical patent/NO20015701L/no

2001-11-22 Publication of NO20015701D0 publication Critical patent/NO20015701D0/no

2006-04-24 Publication of NO321334B1 publication Critical patent/NO321334B1/no

Links

208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 8
201000010099 disease Diseases 0.000 title claims abstract 4
239000003814 drug Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 3
LVXOXXGCJHYEOS-UHFFFAOYSA-N 5-phenylpyrimidine Chemical class C1=CC=CC=C1C1=CN=CN=C1 LVXOXXGCJHYEOS-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 69
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
-1 amino, hydroxy Chemical group 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 15
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
102000002002 Neurokinin-1 Receptors Human genes 0.000 claims abstract description 4
108010040718 Neurokinin-1 Receptors Proteins 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims description 18
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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238000000034 method Methods 0.000 claims description 9
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125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
NJSCUZLQCLYCIE-UHFFFAOYSA-N 5-(2-methylphenyl)-2-methylsulfanylpyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=NC(SC)=NC=C1C1=CC=CC=C1C NJSCUZLQCLYCIE-UHFFFAOYSA-N 0.000 claims description 6
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125000001424 substituent group Chemical group 0.000 claims description 6
125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 5
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101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
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238000012986 modification Methods 0.000 claims description 2
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims description 2
229940044551 receptor antagonist Drugs 0.000 claims description 2
239000002464 receptor antagonist Substances 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
FFYPMPCDMDDUCS-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[5-(2-chlorophenyl)-2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-n,2-dimethylpropanamide Chemical compound N=1C(N2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FFYPMPCDMDDUCS-UHFFFAOYSA-N 0.000 claims 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
UDRXMUSKHDXOJG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-n-methyl-2-[(4-methylpiperazin-1-yl)methyl]pyrimidine-4-carboxamide Chemical compound N=1C(CN2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UDRXMUSKHDXOJG-UHFFFAOYSA-N 0.000 claims 1
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NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 14
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KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
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OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
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239000002466 tachykinin receptor agonist Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
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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 description 1
DBVKXKVWUFDBCI-UHFFFAOYSA-N tert-butyl n-[5-(2-chlorophenyl)-2-methylsulfanylpyrimidin-4-yl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=NC(SC)=NC=C1C1=CC=CC=C1Cl DBVKXKVWUFDBCI-UHFFFAOYSA-N 0.000 description 1
BYLIJEYRQCCRNV-UHFFFAOYSA-N tert-butyl n-[5-(2-methylphenyl)-2-methylsulfanylpyrimidin-4-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=NC(SC)=NC=C1C1=CC=CC=C1C BYLIJEYRQCCRNV-UHFFFAOYSA-N 0.000 description 1
QADQQCQGFKLURJ-UHFFFAOYSA-N tert-butyl n-methyl-n-[5-(2-methylphenyl)-2-methylsulfanylpyrimidin-4-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=NC(SC)=NC=C1C1=CC=CC=C1C QADQQCQGFKLURJ-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms

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Pyridine Compounds (AREA)

NO20015701A 1999-05-31 2001-11-22 5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom. NO321334B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99110482		1999-05-31
PCT/EP2000/004702 WO2000073278A2 (en)	1999-05-31	2000-05-24	5-phenyl-pyrimidine derivatives

Publications (3)

Publication Number	Publication Date
NO20015701L NO20015701L (no)	2001-11-22
NO20015701D0 NO20015701D0 (no)	2001-11-22
NO321334B1 true NO321334B1 (no)	2006-04-24

Family

ID=8238270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015701A NO321334B1 (no)	1999-05-31	2001-11-22	5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom.

Country Status (36)

Country	Link
US (1)	US6756380B1 (es)
EP (1)	EP1187814B1 (es)
JP (1)	JP3590591B2 (es)
KR (1)	KR100478369B1 (es)
CN (1)	CN1187338C (es)
AR (1)	AR024145A1 (es)
AT (1)	ATE273962T1 (es)
AU (1)	AU769265B2 (es)
BR (1)	BR0011097A (es)
CA (1)	CA2375670C (es)
CO (1)	CO5170529A1 (es)
CZ (1)	CZ20014273A3 (es)
DE (1)	DE60013127T2 (es)
DK (1)	DK1187814T3 (es)
ES (1)	ES2225144T3 (es)
GC (1)	GC0000338A (es)
HK (1)	HK1046411B (es)
HR (1)	HRP20010867A2 (es)
HU (1)	HU225016B1 (es)
IL (2)	IL146519A0 (es)
JO (1)	JO2308B1 (es)
MA (1)	MA26794A1 (es)
MX (1)	MXPA01011704A (es)
MY (1)	MY136258A (es)
NO (1)	NO321334B1 (es)
NZ (1)	NZ515408A (es)
PE (1)	PE20010203A1 (es)
PL (1)	PL353492A1 (es)
PT (1)	PT1187814E (es)
RU (1)	RU2244710C2 (es)
SI (1)	SI1187814T1 (es)
TR (1)	TR200103460T2 (es)
TW (1)	TWI263638B (es)
WO (1)	WO2000073278A2 (es)
YU (1)	YU85001A (es)
ZA (1)	ZA200109496B (es)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AUPQ514600A0 (en)	2000-01-18	2000-02-10	James Cook University	Brain injury treatment
CZ20024041A3 (cs) *	2000-06-13	2003-04-16	Basf Aktiengesellschaft	Fungicidní 5-fenyl substituované 2-(kyanamino) pyrimidiny
US6706724B2 (en)	2000-12-21	2004-03-16	Nitromed, Inc.	Substituted aryl compounds as novel cyclooxygenase-2 selective inhibitors, compositions and methods of use
WO2004004731A1 (en)	2002-07-02	2004-01-15	F. Hoffmann-La Roche Ag	2, 5-substituted pyrimidine derivatives as ccr-3 receptor antagonists ix
WO2005046604A2 (en) *	2003-11-10	2005-05-26	Synta Pharmaceuticals, Corp.	Heteroaryl-hydrazone compounds
JP2007217282A (ja) *	2004-03-04	2007-08-30	Astellas Pharma Inc	置換ピリミジン誘導体
AU2005238484A1 (en) *	2004-04-22	2005-11-10	The Procter & Gamble Company	Tri-substituted ureas as cytokine inhibitors
TW200628159A (en) *	2004-11-10	2006-08-16	Synta Pharmaceuticals Corp	IL-12 modulatory compounds
BRPI0606187A2 (pt)	2005-02-25	2009-06-09	Hoffmann La Roche	comprimidos com capacidade de dispersão da substáncia do fármaco melhorada
US9013997B2 (en)	2012-06-01	2015-04-21	Broadcom Corporation	System for performing distributed data cut-through
AU2014232383B2 (en)	2013-03-15	2019-01-17	Epigen Biosciences, Inc.	Heterocyclic compounds useful in the treatment of disease
GB201316600D0 (en) *	2013-09-18	2013-10-30	Redx Pharma Ltd	Agricultural chemicals
WO2016021562A1 (ja) *	2014-08-06	2016-02-11	キッセイ薬品工業株式会社	シアノチオフェン誘導体
JP2018505168A (ja) *	2015-01-30	2018-02-22	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	除草性フェニルピリミジン
CA3029873A1 (en)	2016-07-20	2018-01-25	Basf Se	Herbicidal compositions comprising phenylpyrimidines
US11180470B2 (en)	2016-07-25	2021-11-23	Basf Se	Herbicidal pyrimidine compounds
CN109561685A (zh)	2016-07-25	2019-04-02	巴斯夫欧洲公司	除草的嘧啶化合物
CN109476647A (zh)	2016-07-26	2019-03-15	巴斯夫欧洲公司	除草的嘧啶化合物
US20190269133A1 (en)	2016-07-27	2019-09-05	Basf Se	Herbicidal Pyrimidine Compounds
BR112018077215A2 (pt)	2016-07-28	2019-04-09	Basf Se	compostos de pirimidina de fórmula, utilização de compostos de pirimidina de fórmula, composições herbicida, método para o controle da vegetação indesejada e utilização das composições herbicidas
US20200146289A1 (en)	2017-06-14	2020-05-14	Basf Se	Herbicidal pyrimidine compounds
WO2019121408A1 (en)	2017-12-20	2019-06-27	Basf Se	Herbicidal pyrimidine compounds
WO2019121374A1 (en)	2017-12-20	2019-06-27	Basf Se	Herbicidal pyrimidine compounds
WO2019121373A1 (en)	2017-12-20	2019-06-27	Basf Se	Herbicidal pyrimidine compounds
WO2019121352A1 (en)	2017-12-20	2019-06-27	Basf Se	Herbicidal pyrimidine compounds
CN112955443A (zh) *	2018-09-19	2021-06-11	拜耳公司	具有除草活性的取代的苯基嘧啶酰肼

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3940394A (en) *	1972-03-31	1976-02-24	Santilli Arthur A	2-pyrimidinylthio)alkanoic acids, esters, amides and hydrazides
AR208171A1 (es)	1972-09-29	1976-12-09	Ciba Geigy Ag	Procedimiento para la obtencion de nuevos derivados del acido cef-3-em-4-carboxilico
ATE364606T1 (de)	1993-12-29	2007-07-15	Merck Sharp & Dohme	Substituierte morpholinderivate und ihre verwendung als arzneimittel
AU726522B2 (en)	1995-09-01	2000-11-09	Signal Pharmaceuticals, Inc.	Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions

2000
- 2000-01-02 JO JO200082A patent/JO2308B1/en active
- 2000-05-19 TW TW089109624A patent/TWI263638B/zh not_active IP Right Cessation
- 2000-05-22 US US09/575,789 patent/US6756380B1/en not_active Expired - Fee Related
- 2000-05-24 TR TR2001/03460T patent/TR200103460T2/xx unknown
- 2000-05-24 DK DK00935104T patent/DK1187814T3/da active
- 2000-05-24 RU RU2001133456/04A patent/RU2244710C2/ru not_active IP Right Cessation
- 2000-05-24 CN CNB008082847A patent/CN1187338C/zh not_active Expired - Fee Related
- 2000-05-24 HK HK02108020.5A patent/HK1046411B/zh not_active IP Right Cessation
- 2000-05-24 PL PL00353492A patent/PL353492A1/xx unknown
- 2000-05-24 HU HU0201527A patent/HU225016B1/hu not_active IP Right Cessation
- 2000-05-24 EP EP00935104A patent/EP1187814B1/en not_active Expired - Lifetime
- 2000-05-24 CZ CZ20014273A patent/CZ20014273A3/cs unknown
- 2000-05-24 KR KR10-2001-7015319A patent/KR100478369B1/ko not_active Expired - Fee Related
- 2000-05-24 YU YU85001A patent/YU85001A/sh unknown
- 2000-05-24 CA CA002375670A patent/CA2375670C/en not_active Expired - Fee Related
- 2000-05-24 AU AU50708/00A patent/AU769265B2/en not_active Ceased
- 2000-05-24 SI SI200030472T patent/SI1187814T1/xx unknown
- 2000-05-24 DE DE60013127T patent/DE60013127T2/de not_active Expired - Fee Related
- 2000-05-24 AT AT00935104T patent/ATE273962T1/de not_active IP Right Cessation
- 2000-05-24 BR BR0011097-3A patent/BR0011097A/pt not_active Application Discontinuation
- 2000-05-24 IL IL14651900A patent/IL146519A0/xx not_active IP Right Cessation
- 2000-05-24 PT PT00935104T patent/PT1187814E/pt unknown
- 2000-05-24 NZ NZ515408A patent/NZ515408A/xx unknown
- 2000-05-24 ES ES00935104T patent/ES2225144T3/es not_active Expired - Lifetime
- 2000-05-24 JP JP2000621344A patent/JP3590591B2/ja not_active Expired - Fee Related
- 2000-05-24 HR HR20010867A patent/HRP20010867A2/hr not_active Application Discontinuation
- 2000-05-24 WO PCT/EP2000/004702 patent/WO2000073278A2/en not_active Ceased
- 2000-05-24 MX MXPA01011704A patent/MXPA01011704A/es active IP Right Grant
- 2000-05-26 PE PE2000000509A patent/PE20010203A1/es not_active Application Discontinuation
- 2000-05-29 AR ARP000102642A patent/AR024145A1/es not_active Application Discontinuation
- 2000-05-29 MY MYPI20002385A patent/MY136258A/en unknown
- 2000-05-29 CO CO00039601A patent/CO5170529A1/es not_active Application Discontinuation
- 2000-05-30 GC GCP2000685 patent/GC0000338A/en active
2001
- 2001-11-15 IL IL146519A patent/IL146519A/en unknown
- 2001-11-16 ZA ZA200109496A patent/ZA200109496B/en unknown
- 2001-11-22 NO NO20015701A patent/NO321334B1/no not_active Application Discontinuation
- 2001-11-26 MA MA26425A patent/MA26794A1/fr unknown

Also Published As

Publication number	Publication date
HK1046411A1 (en)	2003-01-10
AU769265B2 (en)	2004-01-22
CO5170529A1 (es)	2002-06-27
HU225016B1 (en)	2006-05-29
MA26794A1 (fr)	2004-12-20
ES2225144T3 (es)	2005-03-16
IL146519A (en)	2006-12-10
CN1353696A (zh)	2002-06-12
SI1187814T1 (en)	2004-12-31
ATE273962T1 (de)	2004-09-15
WO2000073278A2 (en)	2000-12-07
CA2375670C (en)	2009-09-29
PL353492A1 (en)	2003-11-17
DE60013127D1 (de)	2004-09-23
PE20010203A1 (es)	2001-02-15
KR20020003399A (ko)	2002-01-12
MXPA01011704A (es)	2002-05-14
HUP0201527A3 (en)	2005-01-28
TR200103460T2 (tr)	2002-05-21
US6756380B1 (en)	2004-06-29
JO2308B1 (en)	2005-09-12
HK1046411B (zh)	2005-05-27
CA2375670A1 (en)	2000-12-07
RU2244710C2 (ru)	2005-01-20
PT1187814E (pt)	2004-10-29
YU85001A (sh)	2004-09-03
DE60013127T2 (de)	2005-09-08
WO2000073278A3 (en)	2001-07-05
AR024145A1 (es)	2002-09-04
ZA200109496B (en)	2003-02-17
BR0011097A (pt)	2002-03-19
HRP20010867A2 (en)	2003-04-30
EP1187814A2 (en)	2002-03-20
NO20015701L (no)	2001-11-22
IL146519A0 (en)	2002-07-25
NZ515408A (en)	2004-02-27
HUP0201527A2 (en)	2002-08-28
TWI263638B (en)	2006-10-11
CZ20014273A3 (cs)	2002-05-15
DK1187814T3 (da)	2004-12-20
EP1187814B1 (en)	2004-08-18
CN1187338C (zh)	2005-02-02
AU5070800A (en)	2000-12-18
KR100478369B1 (ko)	2005-03-24
NO20015701D0 (no)	2001-11-22
MY136258A (en)	2008-09-30
GC0000338A (en)	2007-03-31
JP2003500477A (ja)	2003-01-07
JP3590591B2 (ja)	2004-11-17

Publication	Publication Date	Title
NO321334B1 (no)	2006-04-24	5-Fenyl-pyrimidin-derivater, fremstilling av disse samt anvendelse av disse for fremstilling av medikament for behandling av sykdom.
NO315554B1 (no)	2003-09-22	4-Fenyl-pyridin-derivater, fremgangsmåte ved fremstilling og anvendelse derav, og medikament inneholdende slike derivater
US6274588B1 (en)	2001-08-14	4-phenyl-pyrimidine derivatives
US6787539B2 (en)	2004-09-07	2,4,5,-trisubstituted pyrimidine derivatives
AU2002227921A1 (en)	2002-08-08	Pyrimidine derivatives

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2008-01-14	FC2A	Withdrawal, rejection or dismissal of laid open patent application