ZA200302192B - Pyrimidine-2, 4, 6-trione metalloproteinase inhibitors. - Google Patents

Pyrimidine-2, 4, 6-trione metalloproteinase inhibitors. Download PDF

Info

Publication number: ZA200302192B
Authority: ZA; South Africa
Prior art keywords: alkyl; group; independently selected; optionally; heteroaryl
Prior art date: 2000-10-26

Application number

ZA200302192A

Other languages

English (en)

Inventor

Noe Mark Carl

Reiter Lawrence Alan

Wythes Martin James

Original Assignee

Pfizer Prod 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

2003-03-19

Publication date

2004-05-05

2003-03-19 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-05-05 Publication of ZA200302192B publication Critical patent/ZA200302192B/en

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HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 title description 6
239000003475 metalloproteinase inhibitor Substances 0.000 title description 4
229910052799 carbon Inorganic materials 0.000 claims description 187
125000000217 alkyl group Chemical group 0.000 claims description 67
-1 >C=0 Chemical compound 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 53
125000001072 heteroaryl group Chemical group 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 25
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 14
125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
229920001774 Perfluoroether Polymers 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims 4
208000024172 Cardiovascular disease Diseases 0.000 claims 2
208000035473 Communicable disease Diseases 0.000 claims 2
208000012895 Gastric disease Diseases 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 2
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208000018631 connective tissue disease Diseases 0.000 claims 2
208000030533 eye disease Diseases 0.000 claims 2
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208000017169 kidney disease Diseases 0.000 claims 2
210000004185 liver Anatomy 0.000 claims 2
208000019423 liver disease Diseases 0.000 claims 2
208000030159 metabolic disease Diseases 0.000 claims 2
230000009933 reproductive health Effects 0.000 claims 2
208000023504 respiratory system disease Diseases 0.000 claims 2
208000017520 skin disease Diseases 0.000 claims 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 1
206010020751 Hypersensitivity Diseases 0.000 claims 1
208000026935 allergic disease Diseases 0.000 claims 1
230000007815 allergy Effects 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
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239000002253 acid Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
125000004043 oxo group Chemical group O=* 0.000 description 6
125000004076 pyridyl group Chemical group 0.000 description 6
150000001721 carbon Chemical group 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
125000000714 pyrimidinyl group Chemical group 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
229940124761 MMP inhibitor Drugs 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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125000003718 tetrahydrofuranyl group Chemical group 0.000 description 4
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239000004215 Carbon black (E152) Substances 0.000 description 3
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125000004122 cyclic group Chemical group 0.000 description 3
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231100000252 nontoxic Toxicity 0.000 description 3
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125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
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 2
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
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108050005238 Collagenase 3 Proteins 0.000 description 2
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
102100027998 Macrophage metalloelastase Human genes 0.000 description 2
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102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 2
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
102100030411 Neutrophil collagenase Human genes 0.000 description 2
101710118230 Neutrophil collagenase Proteins 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
102100030416 Stromelysin-1 Human genes 0.000 description 2
101710108790 Stromelysin-1 Proteins 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
229910052792 caesium Inorganic materials 0.000 description 2
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
229920001436 collagen Polymers 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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230000003349 osteoarthritic effect Effects 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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NDQQRRVKUBPTHQ-QBIQUQHTSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO NDQQRRVKUBPTHQ-QBIQUQHTSA-N 0.000 description 1
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125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
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DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
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125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
125000004475 heteroaralkyl group Chemical group 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000003965 isoxazolidinyl group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 1
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000005503 thioxanyl group Chemical group 0.000 description 1
230000008427 tissue turnover Effects 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
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
230000007306 turnover Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

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- 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
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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
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- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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

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

ZA200302192A 2000-10-26 2003-03-19 Pyrimidine-2, 4, 6-trione metalloproteinase inhibitors. ZA200302192B (en)

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Application Number	Priority Date	Filing Date	Title
US24331400P	2000-10-26	2000-10-26

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

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Also Published As

Publication number	Publication date
PL362919A1 (en)	2004-11-02
IS6749A (is)	2003-03-17
BR0114917A (pt)	2003-07-01
US20020132822A1 (en)	2002-09-19
HN2001000243A (es)	2002-11-07
SV2003000704A (es)	2003-01-13
IL154946A0 (en)	2003-10-31
CA2425280A1 (en)	2002-05-02
WO2002034726A3 (en)	2002-10-17
NZ524774A (en)	2004-09-24
AR035362A1 (es)	2004-05-12
CZ20031069A3 (cs)	2004-05-12
OA12528A (en)	2006-06-02
SK4872003A3 (en)	2004-08-03
JP2004512327A (ja)	2004-04-22
AP2001002319A0 (en)	2001-12-31
EA200300409A1 (ru)	2003-08-28
MXPA03003734A (es)	2003-07-28
PE20020585A1 (es)	2002-07-06
HRP20030331A2 (en)	2003-06-30
ECSP034568A (es)	2003-06-25
KR20030061825A (ko)	2003-07-22
TNSN01150A1 (fr)	2005-11-10
NO20031852L (no)	2003-06-23
PA8531501A1 (es)	2003-06-30
WO2002034726A2 (en)	2002-05-02
UY26981A1 (es)	2002-06-20
AU2002210800A1 (en)	2002-05-06
HUP0302337A2 (hu)	2003-10-28
HUP0302337A3 (en)	2004-01-28
NO20031852D0 (no)	2003-04-24
US6706723B2 (en)	2004-03-16
WO2002034726A9 (en)	2003-03-06
BG107651A (bg)	2003-12-31
EP1332136A2 (en)	2003-08-06
MA26956A1 (fr)	2004-12-20
CN1714084A (zh)	2005-12-28
CR6939A (es)	2003-11-25
EE200300195A (et)	2003-10-15
GT200100214A (es)	2002-07-03
US20050107414A1 (en)	2005-05-19

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