AU2002210800A1 - Pyrimidine-2,4,6-trione metalloproteinase inhibitors - Google Patents

Pyrimidine-2,4,6-trione metalloproteinase inhibitors

Info

Publication number: AU2002210800A1
Authority: AU; Australia
Prior art keywords: alkyl; phenoxy; group; independently selected; heteroaryl
Prior art date: 2000-10-26
Legal status (The legal status 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 status listed.): Abandoned

Application number

AU2002210800A

Other languages

English (en)

Inventor

Mark Carl Noe

Lawrence Alan Reiter

Martin James Wythes

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

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

2001-10-17

Publication date

2002-05-06

2001-10-17 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2002-05-06 Publication of AU2002210800A1 publication Critical patent/AU2002210800A1/en

Status Abandoned legal-status Critical Current

Links

HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 title description 11
239000003475 metalloproteinase inhibitor Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 235
-1 >C=0 Substances 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 95
150000003839 salts Chemical class 0.000 claims description 43
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
125000000623 heterocyclic group Chemical group 0.000 claims description 41
238000000034 method Methods 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 39
229910052760 oxygen Inorganic materials 0.000 claims description 38
125000001072 heteroaryl group Chemical group 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 36
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 35
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
239000001301 oxygen Substances 0.000 claims description 35
208000035475 disorder Diseases 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 34
125000005843 halogen group Chemical group 0.000 claims description 33
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 26
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 23
229910052794 bromium Inorganic materials 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
238000011282 treatment Methods 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 20
229910052801 chlorine Inorganic materials 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229920001774 Perfluoroether Polymers 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 14
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
210000003169 central nervous system Anatomy 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 7
210000004185 liver Anatomy 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
206010020751 Hypersensitivity Diseases 0.000 claims description 6
208000018631 connective tissue disease Diseases 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
208000017169 kidney disease Diseases 0.000 claims description 6
208000023504 respiratory system disease Diseases 0.000 claims description 6
208000017520 skin disease Diseases 0.000 claims description 6
208000024172 Cardiovascular disease Diseases 0.000 claims description 5
208000035473 Communicable disease Diseases 0.000 claims description 5
208000012895 Gastric disease Diseases 0.000 claims description 5
208000026935 allergic disease Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
208000030533 eye disease Diseases 0.000 claims description 5
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208000030159 metabolic disease Diseases 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
230000009933 reproductive health Effects 0.000 claims description 5
208000000453 Skin Neoplasms Diseases 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
OXSYWPDJZMGUOT-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-(4-pyrimidin-4-ylphenoxy)phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2N=CN=CC=2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O OXSYWPDJZMGUOT-UHFFFAOYSA-N 0.000 claims description 2
VDBIMEBUTGEHGU-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(1,3-oxazol-5-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2OC=NC=2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O VDBIMEBUTGEHGU-UHFFFAOYSA-N 0.000 claims description 2
LNEQEABJJGGNEB-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(1,3-thiazol-2-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2SC=CN=2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O LNEQEABJJGGNEB-UHFFFAOYSA-N 0.000 claims description 2
PVQVZBZVLHMJTB-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(1-methylpyrazol-3-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C2=NN(C)C=C2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O PVQVZBZVLHMJTB-UHFFFAOYSA-N 0.000 claims description 2
PKAJLIKKAVTDML-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(2-methyl-1,3-thiazol-4-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2N=C(C)SC=2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O PKAJLIKKAVTDML-UHFFFAOYSA-N 0.000 claims description 2
RFUGNIMGJHUOFI-UHFFFAOYSA-N 5-[4-[4-[[5-(2-ethoxyethyl)-2,4,6-trioxo-1,3-diazinan-5-yl]oxy]phenoxy]phenyl]pentanenitrile Chemical compound C=1C=C(OC=2C=CC(CCCCC#N)=CC=2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O RFUGNIMGJHUOFI-UHFFFAOYSA-N 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
YGKSLVOTSPIKIP-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(1h-pyrazol-5-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C2=NNC=C2)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O YGKSLVOTSPIKIP-UHFFFAOYSA-N 0.000 claims 1
LTARWDASSLDNCM-UHFFFAOYSA-N 5-(2-ethoxyethyl)-5-[4-[4-(2-methylpyrazol-3-yl)phenoxy]phenoxy]-1,3-diazinane-2,4,6-trione Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2N(N=CC=2)C)C=CC=1OC1(CCOCC)C(=O)NC(=O)NC1=O LTARWDASSLDNCM-UHFFFAOYSA-N 0.000 claims 1
239000003112 inhibitor Substances 0.000 description 61
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238000003556 assay Methods 0.000 description 49
239000002585 base Substances 0.000 description 49
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 24
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239000002904 solvent Substances 0.000 description 22
102000000589 Interleukin-1 Human genes 0.000 description 21
108010002352 Interleukin-1 Proteins 0.000 description 21
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 21
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 21
102000029816 Collagenase Human genes 0.000 description 20
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102000002274 Matrix Metalloproteinases Human genes 0.000 description 20
108010000684 Matrix Metalloproteinases Proteins 0.000 description 20
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000007792 addition Methods 0.000 description 18
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238000002360 preparation method Methods 0.000 description 18
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239000002253 acid Substances 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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102100026802 72 kDa type IV collagenase Human genes 0.000 description 8
102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 8
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VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 7
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MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
229960004603 tolcapone Drugs 0.000 description 1
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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GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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230000007306 turnover Effects 0.000 description 1
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OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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Classifications

- 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
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D417/02—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 containing two hetero rings
- C07D417/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Hematology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Ophthalmology & Optometry (AREA)
Cardiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Dental Preparations (AREA)
Plural Heterocyclic Compounds (AREA)

AU2002210800A 2000-10-26 2001-10-17 Pyrimidine-2,4,6-trione metalloproteinase inhibitors Abandoned AU2002210800A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US24331400P	2000-10-26	2000-10-26
US60/243,314		2000-10-26
PCT/IB2001/001953 WO2002034726A2 (en)	2000-10-26	2001-10-17	Pyrimidine-2,4,6-trione metalloproteinase inhibitors

Publications (1)

Publication Number	Publication Date
AU2002210800A1 true AU2002210800A1 (en)	2002-05-06

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ID=36950891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2002210800A Abandoned AU2002210800A1 (en)	2000-10-26	2001-10-17	Pyrimidine-2,4,6-trione metalloproteinase inhibitors

Country Status (36)

Country	Link
US (2)	US6706723B2 (et)
EP (1)	EP1332136A2 (et)
JP (1)	JP2004512327A (et)
KR (1)	KR20030061825A (et)
CN (1)	CN1714084A (et)
AP (1)	AP2001002319A0 (et)
AR (1)	AR035362A1 (et)
AU (1)	AU2002210800A1 (et)
BG (1)	BG107651A (et)
BR (1)	BR0114917A (et)
CA (1)	CA2425280A1 (et)
CR (1)	CR6939A (et)
CZ (1)	CZ20031069A3 (et)
EA (1)	EA200300409A1 (et)
EC (1)	ECSP034568A (et)
EE (1)	EE200300195A (et)
GT (1)	GT200100214A (et)
HN (1)	HN2001000243A (et)
HR (1)	HRP20030331A2 (et)
HU (1)	HUP0302337A3 (et)
IL (1)	IL154946A0 (et)
IS (1)	IS6749A (et)
MA (1)	MA26956A1 (et)
MX (1)	MXPA03003734A (et)
NO (1)	NO20031852L (et)
NZ (1)	NZ524774A (et)
OA (1)	OA12528A (et)
PA (1)	PA8531501A1 (et)
PE (1)	PE20020585A1 (et)
PL (1)	PL362919A1 (et)
SK (1)	SK4872003A3 (et)
SV (1)	SV2003000704A (et)
TN (1)	TNSN01150A1 (et)
UY (1)	UY26981A1 (et)
WO (1)	WO2002034726A2 (et)
ZA (1)	ZA200302192B (et)

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Also Published As

Publication number	Publication date
HUP0302337A3 (en)	2004-01-28
CR6939A (es)	2003-11-25
CZ20031069A3 (cs)	2004-05-12
WO2002034726A3 (en)	2002-10-17
BG107651A (bg)	2003-12-31
US20050107414A1 (en)	2005-05-19
PA8531501A1 (es)	2003-06-30
AP2001002319A0 (en)	2001-12-31
HRP20030331A2 (en)	2003-06-30
SK4872003A3 (en)	2004-08-03
NZ524774A (en)	2004-09-24
EE200300195A (et)	2003-10-15
UY26981A1 (es)	2002-06-20
TNSN01150A1 (fr)	2005-11-10
KR20030061825A (ko)	2003-07-22
MXPA03003734A (es)	2003-07-28
MA26956A1 (fr)	2004-12-20
WO2002034726A9 (en)	2003-03-06
IS6749A (is)	2003-03-17
JP2004512327A (ja)	2004-04-22
PL362919A1 (en)	2004-11-02
SV2003000704A (es)	2003-01-13
AR035362A1 (es)	2004-05-12
NO20031852D0 (no)	2003-04-24
PE20020585A1 (es)	2002-07-06
HN2001000243A (es)	2002-11-07
US6706723B2 (en)	2004-03-16
HUP0302337A2 (hu)	2003-10-28
GT200100214A (es)	2002-07-03
US20020132822A1 (en)	2002-09-19
EA200300409A1 (ru)	2003-08-28
ECSP034568A (es)	2003-06-25
EP1332136A2 (en)	2003-08-06
IL154946A0 (en)	2003-10-31
NO20031852L (no)	2003-06-23
ZA200302192B (en)	2004-05-05
OA12528A (en)	2006-06-02
CN1714084A (zh)	2005-12-28
WO2002034726A2 (en)	2002-05-02
CA2425280A1 (en)	2002-05-02
BR0114917A (pt)	2003-07-01

Publication	Publication Date	Title
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
US6841671B2 (en)	2005-01-11	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501833B1 (en)	2005-11-02	N-substituted-heteroaryloxy-aryl-spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501834B1 (en)	2005-09-07	Triaryl-oxy-aryl-spiro-pyrimidine-2, 4, 6-trione metalloproteinase inhibitors
AU2002210813A1 (en)	2002-05-06	Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors
EP1501515B1 (en)	2005-11-02	Triaryl-oxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors

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2007-05-31	MK4	Application lapsed section 142(2)(d) - no continuation fee paid for the application