BG107653A - Спиро-пиримидин - 2,4,6-трионови инхибитори на металопротеиназa - Google Patents

Спиро-пиримидин - 2,4,6-трионови инхибитори на металопротеиназa Download PDF

Info

Publication number: BG107653A
Authority: BG; Bulgaria
Prior art keywords: alkyl; pyridin; group; compound; formula
Prior art date: 2000-10-26

Application number

BG107653A

Other languages

Bulgarian (bg)

English (en)

Inventor

Brian Bronk

Mark Noe

Martin Wythes

Original Assignee

Pfizer Products Inc.

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.)

2000-10-26

Filing date

2003-03-20

Publication date

2003-12-31

2003-03-20 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2003-12-31 Publication of BG107653A publication Critical patent/BG107653A/bg

Links

239000003475 metalloproteinase inhibitor Substances 0.000 title abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
208000035475 disorder Diseases 0.000 claims abstract description 33
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 231
-1 4-Ethyl-phenoxy Chemical group 0.000 claims description 137
125000000623 heterocyclic group Chemical group 0.000 claims description 94
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 79
239000001301 oxygen Substances 0.000 claims description 79
229910052760 oxygen Inorganic materials 0.000 claims description 79
125000001424 substituent group Chemical group 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 50
239000001257 hydrogen Substances 0.000 claims description 50
238000002360 preparation method Methods 0.000 claims description 43
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 42
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 38
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
229910052717 sulfur Inorganic materials 0.000 claims description 34
239000011593 sulfur Substances 0.000 claims description 34
125000005843 halogen group Chemical group 0.000 claims description 32
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 25
108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 25
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 24
229910052731 fluorine Inorganic materials 0.000 claims description 24
229920001774 Perfluoroether Polymers 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000001072 heteroaryl group Chemical group 0.000 claims description 22
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 20
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
230000002401 inhibitory effect Effects 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
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210000003169 central nervous system Anatomy 0.000 claims description 7
208000017169 kidney disease Diseases 0.000 claims description 7
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210000004185 liver Anatomy 0.000 claims description 6
208000023504 respiratory system disease Diseases 0.000 claims description 6
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208000035473 Communicable disease Diseases 0.000 claims description 5
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208000019423 liver disease Diseases 0.000 claims description 5
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CEKVZJBYHBXOEJ-UHFFFAOYSA-N 3,5,9-trioxodecanal Chemical compound CC(=O)CCCC(=O)CC(=O)CC=O CEKVZJBYHBXOEJ-UHFFFAOYSA-N 0.000 claims description 4
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
208000022873 Ocular disease Diseases 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
COHKACKHFIJNRE-UHFFFAOYSA-N 1-[6-[4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2OC=NN=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O COHKACKHFIJNRE-UHFFFAOYSA-N 0.000 claims description 3
PPPWURMAIMIOFT-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(CN3N=CC=C3)=CC=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O PPPWURMAIMIOFT-UHFFFAOYSA-N 0.000 claims description 3
208000012895 Gastric disease Diseases 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
201000000849 skin cancer Diseases 0.000 claims description 3
201000008261 skin carcinoma Diseases 0.000 claims description 3
FPGLDNOEDDIHDV-UHFFFAOYSA-N 1-[6-(4-bromophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 FPGLDNOEDDIHDV-UHFFFAOYSA-N 0.000 claims description 2
XTGSXSLCZLEGOR-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 XTGSXSLCZLEGOR-UHFFFAOYSA-N 0.000 claims description 2
OSYNXIZIEQNWIC-UHFFFAOYSA-N 4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxybenzonitrile Chemical compound C=1C=C(OC=2C=CC(=CC=2)C#N)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O OSYNXIZIEQNWIC-UHFFFAOYSA-N 0.000 claims description 2
241000282412 Homo Species 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims description 2
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 2
ZPXKNSJQYXAHJU-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 ZPXKNSJQYXAHJU-UHFFFAOYSA-N 0.000 claims description 2
KPXPFHIVDNBNJV-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]butanamide Chemical compound C1=CC(CNC(=O)CCC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 KPXPFHIVDNBNJV-UHFFFAOYSA-N 0.000 claims description 2
208000018556 stomach disease Diseases 0.000 claims description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
GTZIJWRUYJNVLH-UHFFFAOYSA-N 7-[6-(4-fluorophenoxy)pyridin-3-yl]-2,4,7-triazaspiro[5.5]undecane-1,3,5,8-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCCC2=O)C=N1 GTZIJWRUYJNVLH-UHFFFAOYSA-N 0.000 claims 1
206010020649 Hyperkeratosis Diseases 0.000 claims 1
208000000453 Skin Neoplasms Diseases 0.000 claims 1
208000030533 eye disease Diseases 0.000 claims 1
229940080818 propionamide Drugs 0.000 claims 1
238000000034 method Methods 0.000 abstract description 27
206010028980 Neoplasm Diseases 0.000 abstract description 4
206010061218 Inflammation Diseases 0.000 abstract description 3
230000004054 inflammatory process Effects 0.000 abstract description 3
201000011510 cancer Diseases 0.000 abstract description 2
125000004076 pyridyl group Chemical group 0.000 description 85
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
239000003112 inhibitor Substances 0.000 description 63
239000002585 base Substances 0.000 description 59
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
239000002904 solvent Substances 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 46
125000003373 pyrazinyl group Chemical group 0.000 description 45
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239000000203 mixture Substances 0.000 description 40
125000002098 pyridazinyl group Chemical group 0.000 description 40
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
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239000000243 solution Substances 0.000 description 27
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102100027995 Collagenase 3 Human genes 0.000 description 23
125000002883 imidazolyl group Chemical group 0.000 description 23
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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238000003556 assay Methods 0.000 description 20
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239000002253 acid Substances 0.000 description 17
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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Rheumatology (AREA)
Oncology (AREA)
Dermatology (AREA)
Communicable Diseases (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Pregnancy & Childbirth (AREA)
Virology (AREA)
Ophthalmology & Optometry (AREA)
Heart & Thoracic Surgery (AREA)
Tropical Medicine & Parasitology (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)

BG107653A 2000-10-26 2003-03-20 Спиро-пиримидин - 2,4,6-трионови инхибитори на металопротеиназa BG107653A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US24338900P	2000-10-26	2000-10-26
PCT/IB2001/001986 WO2002034753A2 (en)	2000-10-26	2001-10-23	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors

Publications (1)

Publication Number	Publication Date
BG107653A true BG107653A (bg)	2003-12-31

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ID=22918584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107653A BG107653A (bg)	2000-10-26	2003-03-20	Спиро-пиримидин - 2,4,6-трионови инхибитори на металопротеиназa

Country Status (32)

Country	Link
EP (1)	EP1332146A2 (pl)
JP (1)	JP2004518635A (pl)
KR (1)	KR20040004412A (pl)
CN (1)	CN1501937A (pl)
AP (1)	AP2001002318A0 (pl)
AR (1)	AR035069A1 (pl)
AU (1)	AU2002210813A1 (pl)
BG (1)	BG107653A (pl)
BR (1)	BR0114913A (pl)
CA (1)	CA2425283A1 (pl)
CZ (1)	CZ20031083A3 (pl)
EA (1)	EA005762B1 (pl)
EC (1)	ECSP034567A (pl)
EE (1)	EE200300196A (pl)
GT (1)	GT200100213A (pl)
HN (1)	HN2001000244A (pl)
HR (1)	HRP20030332A2 (pl)
HU (1)	HUP0301577A3 (pl)
IL (1)	IL154948A0 (pl)
IS (1)	IS6762A (pl)
MA (1)	MA26957A1 (pl)
MX (1)	MXPA03003735A (pl)
NO (1)	NO20031853L (pl)
OA (1)	OA12529A (pl)
PA (1)	PA8531401A1 (pl)
PE (1)	PE20020589A1 (pl)
PL (1)	PL366201A1 (pl)
SK (1)	SK4972003A3 (pl)
SV (1)	SV2003000705A (pl)
TN (1)	TNSN01149A1 (pl)
WO (1)	WO2002034753A2 (pl)
ZA (1)	ZA200302190B (pl)

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BR0207865A (pt)	2001-02-14	2004-03-23	Warner Lambert Co	Benzotiadiazinas inibidores de metaloproteinases de matriz
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BR0213233A (pt)	2001-10-12	2005-01-04	Warner Lambert Co	Alcinos inibidores de metaloproteinase de matriz
US6962922B2 (en)	2001-10-12	2005-11-08	Warner-Lambert Company Llc	Alkynylated quinazoline compounds
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AU2003228701A1 (en) *	2002-04-25	2003-11-10	Bristol-Myers Squibb Company	Spirobarbituric acid derivatives useful as inhibitors of matrix metalloproteases
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WO2004014375A2 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Fused bicyclic metalloproteinase inhibitors
AU2003250470A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Pyrimidinone fused bicyclic metalloproteinase inhibitors
AU2003249477A1 (en)	2002-08-13	2004-02-25	Warner-Lambert Company Llc	Heterobicylcic metalloproteinase inhibitors
EP1539709A1 (en)	2002-08-13	2005-06-15	Warner-Lambert Company LLC	Azaisoquinoline derivatives as matrix metalloproteinase inhibitors
MXPA05001783A (es)	2002-08-13	2005-04-25	Warner Lambert Co	Derivados de pirimidina-2,4-diona como inhibidores de las metaloproteinasas de matriz.
WO2004014892A1 (en) *	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Monocyclic derivatives as matrix metalloproteinase inhibitors
PA8578101A1 (es)	2002-08-13	2004-05-07	Warner Lambert Co	Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz
WO2004014909A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors
WO2004014378A1 (en)	2002-08-13	2004-02-19	Warner-Lambert Company Llc	3-isoquinolinone derivatives as matrix metalloproteinase inhiitors
JP2005539020A (ja)	2002-08-13	2005-12-22	ワーナー−ランバートカンパニーリミティドライアビリティーカンパニー	マトリクスメタロプロテイナーゼ阻害物質としてのクロモン誘導体
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GB0223249D0 (en) *	2002-10-08	2002-11-13	Amersham Plc	Improved imaging agents
WO2004084903A1 (en) *	2003-03-27	2004-10-07	F. Hoffmann-La Roche Ag	Use of a trioxopyrimidine for the treatment and prevention of ocular pathologic angiogenesis
WO2004084902A1 (en) *	2003-03-28	2004-10-07	F. Hoffmann-La Roche Ag	Use of a trioxopyrimidine for the treatment of chronic wounds
FR2858232B1 (fr) *	2003-07-29	2006-03-03	Pierre Potier	Utilisation d'un derive de biguanide pour proteger la peau des radiations uvb
AU2005230379B2 (en) *	2004-04-01	2010-07-22	Universite De Liege	Use of a trioxopyrimidine for the treatment and prevention of bronchial inflammatory diseases
DOP2006000268A (es)	2005-12-22	2007-07-31	Pfizer Prod Inc	Agentes antibacterianos
US8153166B2 (en) *	2006-06-08	2012-04-10	Chih-Hsiung Lin	Composition for prophylaxis or treatment of urinary system infection and method thereof
CN102285934B (zh) *	2009-01-08	2013-08-14	四川大学	螺环二烯酮衍生物及其制备方法和用途
KR102168738B1 (ko) *	2012-12-10	2020-10-22	추가이 세이야쿠 가부시키가이샤	히단토인 유도체
KR101594506B1 (ko) *	2014-03-20	2016-02-17	한국화학연구원	골 관련 질환 치료용 조성물
KR102266021B1 (ko)	2014-06-09	2021-06-16	추가이 세이야쿠 가부시키가이샤	히단토인 유도체 함유 의약 조성물
US11292782B2 (en)	2018-11-30	2022-04-05	Nuvation Bio Inc.	Diarylhydantoin compounds and methods of use thereof
CN110092790B (zh) *	2019-06-11	2020-07-24	东北农业大学	一种生物碱类化合物及其制备方法和应用
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2001
- 2001-10-23 CN CNA018179231A patent/CN1501937A/zh active Pending
- 2001-10-23 AU AU2002210813A patent/AU2002210813A1/en not_active Abandoned
- 2001-10-23 HR HR20030332A patent/HRP20030332A2/hr not_active Application Discontinuation
- 2001-10-23 CZ CZ20031083A patent/CZ20031083A3/cs unknown
- 2001-10-23 EE EEP200300196A patent/EE200300196A/xx unknown
- 2001-10-23 SK SK497-2003A patent/SK4972003A3/sk unknown
- 2001-10-23 OA OA1200300123A patent/OA12529A/en unknown
- 2001-10-23 AP APAP/P/2001/002318A patent/AP2001002318A0/en unknown
- 2001-10-23 MX MXPA03003735A patent/MXPA03003735A/es unknown
- 2001-10-23 IL IL15494801A patent/IL154948A0/xx unknown
- 2001-10-23 WO PCT/IB2001/001986 patent/WO2002034753A2/en not_active Ceased
- 2001-10-23 EP EP01978721A patent/EP1332146A2/en not_active Withdrawn
- 2001-10-23 KR KR10-2003-7005753A patent/KR20040004412A/ko not_active Ceased
- 2001-10-23 PL PL01366201A patent/PL366201A1/pl not_active Application Discontinuation
- 2001-10-23 JP JP2002537743A patent/JP2004518635A/ja not_active Withdrawn
- 2001-10-23 BR BR0114913-0A patent/BR0114913A/pt not_active IP Right Cessation
- 2001-10-23 HU HU0301577A patent/HUP0301577A3/hu unknown
- 2001-10-23 EA EA200300306A patent/EA005762B1/ru not_active IP Right Cessation
- 2001-10-23 CA CA002425283A patent/CA2425283A1/en not_active Abandoned
- 2001-10-24 HN HN2001000244A patent/HN2001000244A/es unknown
- 2001-10-24 AR ARP010104977A patent/AR035069A1/es unknown
- 2001-10-25 TN TNTNSN01149A patent/TNSN01149A1/fr unknown
- 2001-10-25 SV SV2001000705A patent/SV2003000705A/es unknown
- 2001-10-25 PE PE2001001060A patent/PE20020589A1/es not_active Application Discontinuation
- 2001-10-25 GT GT200100213A patent/GT200100213A/es unknown
- 2001-10-26 PA PA20018531401A patent/PA8531401A1/es unknown
2003
- 2003-03-19 ZA ZA200302190A patent/ZA200302190B/en unknown
- 2003-03-20 BG BG107653A patent/BG107653A/bg unknown
- 2003-03-27 IS IS6762A patent/IS6762A/is unknown
- 2003-04-22 MA MA27117A patent/MA26957A1/fr unknown
- 2003-04-24 NO NO20031853A patent/NO20031853L/no not_active Application Discontinuation
- 2003-04-25 EC EC2003004567A patent/ECSP034567A/es unknown

Also Published As

Publication number	Publication date
CN1501937A (zh)	2004-06-02
WO2002034753A2 (en)	2002-05-02
NO20031853D0 (no)	2003-04-24
KR20040004412A (ko)	2004-01-13
EA005762B1 (ru)	2005-06-30
ECSP034567A (es)	2003-06-25
MA26957A1 (fr)	2004-12-20
EE200300196A (et)	2003-10-15
BR0114913A (pt)	2003-07-01
PE20020589A1 (es)	2002-07-06
WO2002034753A3 (en)	2002-08-15
ZA200302190B (en)	2004-04-28
IL154948A0 (en)	2003-10-31
MXPA03003735A (es)	2003-07-28
NO20031853L (no)	2003-06-23
PL366201A1 (pl)	2005-01-24
EA200300306A1 (ru)	2003-08-28
HUP0301577A3 (en)	2006-02-28
PA8531401A1 (es)	2003-06-30
GT200100213A (es)	2002-07-03
AU2002210813A1 (en)	2002-05-06
TNSN01149A1 (fr)	2005-11-10
HUP0301577A2 (hu)	2003-11-28
CA2425283A1 (en)	2002-05-02
IS6762A (is)	2003-03-27
SK4972003A3 (en)	2004-05-04
SV2003000705A (es)	2003-01-13
OA12529A (en)	2006-06-02
AR035069A1 (es)	2004-04-14
EP1332146A2 (en)	2003-08-06
AP2001002318A0 (en)	2001-12-31
HRP20030332A2 (en)	2003-06-30
CZ20031083A3 (cs)	2004-03-17
HN2001000244A (es)	2003-11-07
JP2004518635A (ja)	2004-06-24

Publication	Publication Date	Title
BG107653A (bg)	2003-12-31	Спиро-пиримидин - 2,4,6-трионови инхибитори на металопротеиназa
EP1501833B1 (en)	2005-11-02	N-substituted-heteroaryloxy-aryl-spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
US6841671B2 (en)	2005-01-11	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
US6706723B2 (en)	2004-03-16	Pyrimidine-2,4,6-trione metalloproteinase inhibitors
US6919332B2 (en)	2005-07-19	N-substituted-heteroaryloxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501834B1 (en)	2005-09-07	Triaryl-oxy-aryl-spiro-pyrimidine-2, 4, 6-trione metalloproteinase inhibitors
MXPA02001561A (es)	2002-07-02	Pirimidina-2,4,6-trionas inhibidores de metaloproteinasas.
US6897223B2 (en)	2005-05-24	Pyridine fused bicyclic metalloproteinase inhibitors
US20040006057A1 (en)	2004-01-08	Triaryl-oxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors
US6387901B1 (en)	2002-05-14	Alkyne containing metalloproteinase inhibitors