AP1288A - Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation. - Google Patents

Info

Publication number

AP1288A

AP1288A APAP/P/2001/002270A AP2001002270A AP1288A AP 1288 A AP1288 A AP 1288A AP 2001002270 A AP2001002270 A AP 2001002270A AP 1288 A AP1288 A AP 1288A

Authority

AP

ARIPO

Prior art keywords

group

formula

salt

solvate

compound

Prior art date

1995-12-08

Links

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• 238000000034 method Methods 0.000 title claims abstract description 44
• 239000000543 intermediate Substances 0.000 title abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 title abstract description 10
• 238000002360 preparation method Methods 0.000 title description 14
• 239000003475 metalloproteinase inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 150000003839 salts Chemical class 0.000 claims abstract description 98
• 125000003118 aryl group Chemical group 0.000 claims abstract description 73
• 239000012453 solvate Substances 0.000 claims abstract description 73
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 57
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• -1 acycloalkyl group Chemical group 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
• 229910052702 rhenium Inorganic materials 0.000 claims description 10
• 229910052710 silicon Inorganic materials 0.000 claims description 9
• 150000005690 diesters Chemical class 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 239000000651 prodrug Substances 0.000 abstract description 21
• 229940002612 prodrug Drugs 0.000 abstract description 21
• 125000001424 substituent group Chemical group 0.000 abstract description 19
• 230000000694 effects Effects 0.000 abstract description 13
• 102000005741 Metalloproteases Human genes 0.000 abstract description 9
• 108010006035 Metalloproteases Proteins 0.000 abstract description 9
• 125000006413 ring segment Chemical group 0.000 abstract description 7
• 230000002401 inhibitory effect Effects 0.000 abstract description 5
• 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
• 125000005842 heteroatom Chemical group 0.000 abstract description 3
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 230
• 235000013350 formula milk Nutrition 0.000 description 223
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• 150000002148 esters Chemical class 0.000 description 19
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• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 18
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• JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 18
• 235000011054 acetic acid Nutrition 0.000 description 17
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• 238000004587 chromatography analysis Methods 0.000 description 17
• 239000000725 suspension Substances 0.000 description 16
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 15
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