JP2004521908A - Ｍｍｐ阻害剤としてのトリアゾロ化合物 - Google Patents
Ｍｍｐ阻害剤としてのトリアゾロ化合物 Download PDFInfo
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- JP2004521908A JP2004521908A JP2002564526A JP2002564526A JP2004521908A JP 2004521908 A JP2004521908 A JP 2004521908A JP 2002564526 A JP2002564526 A JP 2002564526A JP 2002564526 A JP2002564526 A JP 2002564526A JP 2004521908 A JP2004521908 A JP 2004521908A
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- Prior art keywords
- alkyl
- formula
- compound
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- oxo
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- 150000001875 compounds Chemical class 0.000 title claims description 248
- 229940124761 MMP inhibitor Drugs 0.000 title description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 68
- 239000001257 hydrogen Substances 0.000 claims abstract description 68
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 47
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 44
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000001301 oxygen Substances 0.000 claims abstract description 44
- 239000011593 sulfur Substances 0.000 claims abstract description 41
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000011159 matrix material Substances 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 19
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 15
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 14
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 84
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 74
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- -1 2,1,3-benzothiadiazolyl Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000004434 sulfur atom Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 14
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 14
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000001041 indolyl group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 201000008482 osteoarthritis Diseases 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 12
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 208000002780 macular degeneration Diseases 0.000 claims description 11
- 229940095102 methyl benzoate Drugs 0.000 claims description 11
- FAUYRBMJEJPIBN-UHFFFAOYSA-N C1=NN=C2N1C1=CC=C(C=C1C=N2)C(=O)N Chemical compound C1=NN=C2N1C1=CC=C(C=C1C=N2)C(=O)N FAUYRBMJEJPIBN-UHFFFAOYSA-N 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- BOAPXJJSGBQJPM-UHFFFAOYSA-N 4-[[7-[(4-fluorophenyl)methylcarbamoyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C(=O)C2=CC(C(=O)NCC=3C=CC(F)=CC=3)=CC=C2N2C=NN=C21 BOAPXJJSGBQJPM-UHFFFAOYSA-N 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 208000028169 periodontal disease Diseases 0.000 claims description 6
- VMSPJYJGWZXQDC-UHFFFAOYSA-N 2-[4-[[7-[(4-methoxyphenyl)methylcarbamoyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C2N3C=NN=C3N(CC=3C=CC(CC(O)=O)=CC=3)C(=O)C2=C1 VMSPJYJGWZXQDC-UHFFFAOYSA-N 0.000 claims description 5
- SZTKBYYYFKIGFX-UHFFFAOYSA-N 2-[4-[[7-[methyl(pyridin-4-yl)carbamoyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4-yl]methyl]phenyl]acetic acid Chemical compound C=1C=NC=CC=1N(C)C(=O)C(C=1)=CC=C(N2C=NN=C22)C=1C(=O)N2CC1=CC=C(CC(O)=O)C=C1 SZTKBYYYFKIGFX-UHFFFAOYSA-N 0.000 claims description 5
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
- KYMITHWDCVDTJI-UHFFFAOYSA-N C(C)(=O)OCC1=CC=C(C=C1)CN1C=2N(C3=CC=C(C=C3C1=O)C(NCC1=CC3=C(OCO3)C=C1)=O)C=NN2 Chemical compound C(C)(=O)OCC1=CC=C(C=C1)CN1C=2N(C3=CC=C(C=C3C1=O)C(NCC1=CC3=C(OCO3)C=C1)=O)C=NN2 KYMITHWDCVDTJI-UHFFFAOYSA-N 0.000 claims description 5
- HGFMWNVYEIWJCZ-UHFFFAOYSA-N C(C)(=O)OCC1=CC=C(C=C1)CN1C=2N(C3=CC=C(C=C3C1=O)C(NCC1=CC=C(C=C1)OC)=O)C=NN2 Chemical compound C(C)(=O)OCC1=CC=C(C=C1)CN1C=2N(C3=CC=C(C=C3C1=O)C(NCC1=CC=C(C=C1)OC)=O)C=NN2 HGFMWNVYEIWJCZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 206010003246 arthritis Diseases 0.000 claims description 5
- BQNPWAAFQUWJQO-UHFFFAOYSA-N benzyl 4-benzyl-5-oxo-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxylate Chemical compound C=1C=C(N2C=NN=C2N(CC=2C=CC=CC=2)C2=O)C2=CC=1C(=O)OCC1=CC=CC=C1 BQNPWAAFQUWJQO-UHFFFAOYSA-N 0.000 claims description 5
- DFZBQXFAFJIXHG-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4-[(4-cyanophenyl)methyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxamide Chemical compound C=1C=C2OCOC2=CC=1CNC(=O)C(C=1)=CC=C(N2C=NN=C22)C=1C(=O)N2CC1=CC=C(C#N)C=C1 DFZBQXFAFJIXHG-UHFFFAOYSA-N 0.000 claims description 5
- FMJHCLBRSAPIGN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4-benzyl-5-oxo-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxamide Chemical compound C=1C=C2OCOC2=CC=1CNC(=O)C(C=1)=CC=C(N2C=NN=C22)C=1C(=O)N2CC1=CC=CC=C1 FMJHCLBRSAPIGN-UHFFFAOYSA-N 0.000 claims description 5
- WQDWXMNOPFULEC-UHFFFAOYSA-N pyridin-4-ylmethyl 4-benzyl-5-oxo-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxylate Chemical compound C=1C=C(N2C=NN=C2N(CC=2C=CC=CC=2)C2=O)C2=CC=1C(=O)OCC1=CC=NC=C1 WQDWXMNOPFULEC-UHFFFAOYSA-N 0.000 claims description 5
- AHQAOXKCZQNXHU-UHFFFAOYSA-N 4-[[7-[(4-methoxyphenyl)methylcarbamoyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazolin-4-yl]methyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C2N3C=NN=C3N(CC=3C=CC(=CC=3)C(O)=O)C(=O)C2=C1 AHQAOXKCZQNXHU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- FMJDKOBXRJYZKD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4-benzyl-5-oxoimidazo[1,2-a]quinazoline-7-carboxamide Chemical compound C=1C=C2OCOC2=CC=1CNC(=O)C(C=1)=CC=C(N2C=CN=C22)C=1C(=O)N2CC1=CC=CC=C1 FMJDKOBXRJYZKD-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- QZJZINZWIMVODU-UHFFFAOYSA-N 4-[(4-cyanophenyl)methyl]-5-oxo-n-(pyridin-4-ylmethyl)-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxamide Chemical compound C=1C=C(N2C=NN=C2N(CC=2C=CC(=CC=2)C#N)C2=O)C2=CC=1C(=O)NCC1=CC=NC=C1 QZJZINZWIMVODU-UHFFFAOYSA-N 0.000 claims description 3
- HKBRYGMHTOURBK-UHFFFAOYSA-N 4-[2-(4-chlorophenoxy)ethyl]-n-[(4-methoxyphenyl)methyl]-5-oxo-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C2N3C=NN=C3N(CCOC=3C=CC(Cl)=CC=3)C(=O)C2=C1 HKBRYGMHTOURBK-UHFFFAOYSA-N 0.000 claims description 3
- MLLSAERKYCNOKU-UHFFFAOYSA-N 4-benzyl-5-oxo-n-(pyridin-4-ylmethyl)-[1,2,4]triazolo[4,3-a]quinazoline-7-carboxamide Chemical compound C=1C=C(N2C=NN=C2N(CC=2C=CC=CC=2)C2=O)C2=CC=1C(=O)NCC1=CC=NC=C1 MLLSAERKYCNOKU-UHFFFAOYSA-N 0.000 claims description 3
- AXIMIOFWLRUQPQ-UHFFFAOYSA-N 4-benzyl-5-oxo-n-(pyridin-4-ylmethyl)imidazo[1,2-a]quinazoline-7-carboxamide Chemical compound C=1C=C(N2C=CN=C2N(CC=2C=CC=CC=2)C2=O)C2=CC=1C(=O)NCC1=CC=NC=C1 AXIMIOFWLRUQPQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- CKDZEXUCUNHQIY-UHFFFAOYSA-N 2h-tetrazole-5-carbonitrile Chemical compound N#CC=1N=NNN=1 CKDZEXUCUNHQIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 20
- 125000004429 atom Chemical group 0.000 claims 6
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- 239000000543 intermediate Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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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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Landscapes
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- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| PCT/EP2002/001961 WO2002064595A1 (en) | 2001-02-14 | 2002-02-11 | Triazolo compounds as mmp inhibitors |
Publications (2)
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| JP2004521908A true JP2004521908A (ja) | 2004-07-22 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2008540687A (ja) * | 2005-05-20 | 2008-11-20 | アラントス−フアーマシユーテイカルズ・インコーポレイテツド | ピリミジン若しくはトリアジン縮合二環式メタロプロテアーゼ阻害薬 |
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| WO2002064598A1 (en) * | 2001-02-14 | 2002-08-22 | Warner-Lambert Company Llc | Thieno'2,3-d pyrimidindione derivatives as matrix metalloproteinase inhibitors |
| PA8539501A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Compuestos triazolo como inhibidores de mmp |
| US6924276B2 (en) | 2001-09-10 | 2005-08-02 | Warner-Lambert Company | Diacid-substituted heteroaryl derivatives as matrix metalloproteinase inhibitors |
| MXPA04002537A (es) | 2001-10-12 | 2004-05-31 | Warner Lambert Co | Alquinos como inhibidores de metaloproteinasa de matriz. |
| US6962922B2 (en) | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| US6747147B2 (en) | 2002-03-08 | 2004-06-08 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| US6894057B2 (en) | 2002-03-08 | 2005-05-17 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| US20040006077A1 (en) * | 2002-06-25 | 2004-01-08 | Bernard Gaudilliere | Thiazine and oxazine derivatives as MMP-13 inhibitors |
| AU2003281169A1 (en) * | 2002-07-17 | 2004-02-02 | Warner-Lambert Company Llc | Combination of an allosteric carboxylic inhibitor of matrix metalloproteinase-13 with celecoxib or valdecoxib |
| JP2006502114A (ja) * | 2002-07-17 | 2006-01-19 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | マトリクスメタロプロテイナーゼ−１３のアロステリックアルキン阻害薬とセレコキシブまたはバルデコキシブとの組合せ |
| EP1531904A1 (en) * | 2002-07-17 | 2005-05-25 | Warner-Lambert Company LLC | Combination of an allosteric inhibitor of matrix metalloproteinase-13 with a selective inhibitor of cyclooxygenase-2 that is not celecoxib or valdecoxib |
| MXPA05000729A (es) * | 2002-07-17 | 2005-04-08 | Warner Lambert Co | Combinacion de un inhibidor alosterico de metaloproteinasa-13 de matriz con celecoxib o valdecoxib. |
| AU2003253165A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Pyrimidine fused bicyclic metalloproteinase inhibitors |
| AU2003250482A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Phthalimide derivatives as matrix metalloproteinase inhibitors |
| WO2004014867A2 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Matrix metalloproteinase inhibitors and methods for identification of lead compounds |
| AU2003249539A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors |
| WO2004014354A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 1,6-fused uracil derivatives as matrix metalloproteinase inhibitors |
| AU2003253186A1 (en) | 2002-08-13 | 2004-02-25 | 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 |
| WO2004014868A2 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Pyrimidine-2,4-dione derivatives as matrix metalloproteinase inhibitors |
| AU2003250475A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | 5,6-fused 3,4-dihydropyrimidine-2-one derivatives as matrix metalloproteinase inhibitors |
| WO2004014908A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Heterobicylcic metalloproteinase inhibitors |
| BR0313384A (pt) | 2002-08-13 | 2005-07-12 | Warner Lambert Co | Derivados de cromona como inibidores de metaloproteinases de matriz |
| WO2004014375A2 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Fused bicyclic metalloproteinase inhibitors |
| CA2492019A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Isoquinoline derivatives as matrix metalloproteinase inhibitors |
| BR0313459A (pt) | 2002-08-13 | 2005-06-21 | Warner Lambert Co | Derivados monocìclicos como inibidores de metaloproteinases de matriz |
| WO2004014866A1 (en) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Azaisoquinoline derivatives as matrix metalloproteinase inhibitors |
| AU2003250470A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Pyrimidinone fused bicyclic metalloproteinase inhibitors |
| PA8578101A1 (es) | 2002-08-13 | 2004-05-07 | Warner Lambert Co | Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz |
| US20040142950A1 (en) * | 2003-01-17 | 2004-07-22 | Bunker Amy Mae | Amide and ester matrix metalloproteinase inhibitors |
| WO2005002585A1 (en) * | 2003-07-02 | 2005-01-13 | Warner-Lambert Company Llc | Combination of an allosteric inhibitor of matrix metalloproteinase-13 and a ligand to an alpha-2-delta receptor |
| WO2005016926A1 (en) * | 2003-08-19 | 2005-02-24 | Warner-Lambert Company Llc | Pyrido [3,4-d] pyrimidine derivatives as matrix metalloproteinase-13 inhibitors |
| US20060247231A1 (en) * | 2003-12-18 | 2006-11-02 | Warner-Lambert Company Llc | Amide and ester matrix metalloproteinase inhibitors |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US7795877B2 (en) * | 2006-11-02 | 2010-09-14 | Current Technologies, Llc | Power line communication and power distribution parameter measurement system and method |
| CA2670083A1 (en) * | 2006-11-20 | 2008-05-29 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| WO2009088990A1 (en) | 2008-01-04 | 2009-07-16 | Intellikine, Inc. | Certain chemical entities, compositions and methods |
| DE102010031945A1 (de) * | 2010-07-22 | 2012-01-26 | Osram Opto Semiconductors Gmbh | Halbleiterbauelement und Verfahren zur Herstellung eines Halbleiterbauelements |
| NZ612909A (en) | 2011-01-10 | 2015-09-25 | Infinity Pharmaceuticals Inc | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
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| CN115197225B (zh) * | 2021-09-03 | 2023-04-11 | 贵州大学 | 一种五元杂环并喹唑啉酮类化合物及其制备方法 |
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| IL66835A (en) * | 1981-09-24 | 1988-05-31 | Roussel Uclaf | 1,4-disubstituted(1,2,4)triazolo(4,3-alpha)quinazolin-5(4h)-one derivatives and their salts,their preparation and pharmaceutical compositions containing them |
| DE3677445D1 (de) * | 1985-09-30 | 1991-03-14 | Ciba Geigy Ag | 2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung. |
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| UA59453C2 (uk) | 1998-08-12 | 2003-09-15 | Пфайзер Продактс Інк. | Похідні гідроксипіпеколат гідроксамової кислоти як інгібітори матричних металопротеїназ |
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| US6934639B1 (en) | 2000-02-25 | 2005-08-23 | Wyeth | Methods for designing agents that interact with MMP-13 |
| EP1138680A1 (en) | 2000-03-29 | 2001-10-04 | Pfizer Products Inc. | Gem substituted sulfonyl hydroxamic acids as MMP inhibitors |
| KR20040004412A (ko) | 2000-10-26 | 2004-01-13 | 화이자 프로덕츠 인크. | 스피로-피리미딘-2,4,6-트리온 메탈로프로테이나제 억제제 |
| KR20030061825A (ko) | 2000-10-26 | 2003-07-22 | 화이자 프로덕츠 인크. | 피리미딘-2,4,6-트리온 메탈로프로테이나제 억제제 |
| PA8539401A1 (es) | 2001-02-14 | 2002-10-28 | Warner Lambert Co | Quinazolinas como inhibidores de mmp-13 |
| PA8539301A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Inhibidores de la metaloproteinasa de la matriz |
| PA8539501A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Compuestos triazolo como inhibidores de mmp |
| MXPA04003008A (es) | 2001-10-12 | 2004-07-16 | Warner Lambert Co | Compuestos pirimidina de anillo fusionado alquinilado como inhibidores de metaloproteasa 13 de la matriz. |
| US6962922B2 (en) * | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| MXPA04002537A (es) | 2001-10-12 | 2004-05-31 | Warner Lambert Co | Alquinos como inhibidores de metaloproteinasa de matriz. |
| US6747147B2 (en) * | 2002-03-08 | 2004-06-08 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| US6894057B2 (en) * | 2002-03-08 | 2005-05-17 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| WO2003076416A1 (en) | 2002-03-08 | 2003-09-18 | Warner-Lambert Company Llc | Oxo azabicyclic compounds |
| AU2002333256A1 (en) | 2002-06-25 | 2004-01-06 | Warner-Lambert Company Llc | Thiazine and oxazine derivatives as mmp-13 inhibitors for treating arthritis |
| US20040006077A1 (en) * | 2002-06-25 | 2004-01-08 | Bernard Gaudilliere | Thiazine and oxazine derivatives as MMP-13 inhibitors |
| AU2003249539A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors |
-
2002
- 2002-02-08 PA PA20028539501A patent/PA8539501A1/es unknown
- 2002-02-11 BR BR0207270-0A patent/BR0207270A/pt not_active IP Right Cessation
- 2002-02-11 DE DE60203995T patent/DE60203995T2/de not_active Expired - Fee Related
- 2002-02-11 MX MXPA03007249A patent/MXPA03007249A/es unknown
- 2002-02-11 AT AT02702366T patent/ATE294805T1/de not_active IP Right Cessation
- 2002-02-11 ES ES02702366T patent/ES2239216T3/es not_active Expired - Lifetime
- 2002-02-11 EP EP02702366A patent/EP1362048B1/en not_active Expired - Lifetime
- 2002-02-11 CA CA002437588A patent/CA2437588A1/en not_active Abandoned
- 2002-02-11 JP JP2002564526A patent/JP2004521908A/ja not_active Abandoned
- 2002-02-11 WO PCT/EP2002/001961 patent/WO2002064595A1/en not_active Ceased
- 2002-02-13 HN HN2002000038A patent/HN2002000038A/es unknown
- 2002-02-13 PE PE2002000115A patent/PE20020885A1/es not_active Application Discontinuation
- 2002-02-13 AR ARP020100471A patent/AR032677A1/es not_active Application Discontinuation
- 2002-02-13 SV SV2002000875A patent/SV2002000875A/es not_active Application Discontinuation
- 2002-02-14 US US10/075,654 patent/US6849637B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008540687A (ja) * | 2005-05-20 | 2008-11-20 | アラントス−フアーマシユーテイカルズ・インコーポレイテツド | ピリミジン若しくはトリアジン縮合二環式メタロプロテアーゼ阻害薬 |
| JP2013181033A (ja) * | 2005-05-20 | 2013-09-12 | Alantos Pharmaceuticals Holding Inc | ヘテロ二環式メタロプロテアーゼ阻害薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002064595A1 (en) | 2002-08-22 |
| DE60203995T2 (de) | 2005-09-22 |
| ES2239216T3 (es) | 2005-09-16 |
| PE20020885A1 (es) | 2002-10-26 |
| US20020151558A1 (en) | 2002-10-17 |
| MXPA03007249A (es) | 2005-02-14 |
| EP1362048A1 (en) | 2003-11-19 |
| AR032677A1 (es) | 2003-11-19 |
| DE60203995D1 (de) | 2005-06-09 |
| CA2437588A1 (en) | 2002-08-22 |
| US6849637B2 (en) | 2005-02-01 |
| PA8539501A1 (es) | 2002-09-30 |
| BR0207270A (pt) | 2004-02-10 |
| ATE294805T1 (de) | 2005-05-15 |
| SV2002000875A (es) | 2002-10-04 |
| EP1362048B1 (en) | 2005-05-04 |
| HN2002000038A (es) | 2002-09-05 |
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