UA81491C2 - N-{'4-substituted piperazine-1-sulfonylmethyl]alkyl}-n-hydroxyformamide compounds as metalloproteinase inhibitors, pharmaceutical composition based thereon, proces for the preparation thereof, intermediate (variants) - Google Patents

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Publication number

UA81491C2

UA81491C2 UAA200511723A UAA200511723A UA81491C2 UA 81491 C2 UA81491 C2 UA 81491C2 UA A200511723 A UAA200511723 A UA A200511723A UA A200511723 A UAA200511723 A UA A200511723A UA 81491 C2 UA81491 C2 UA 81491C2

Authority

UA

Ukraine

Prior art keywords

compound

ring

formula

pharmaceutically acceptable

prodrug

Prior art date

2003-06-27

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
• 238000002360 preparation method Methods 0.000 title claims abstract description 9
• 125000000217 alkyl group Chemical group 0.000 title abstract description 7
• 239000003475 metalloproteinase inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 146
• 238000000034 method Methods 0.000 claims abstract description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 229940002612 prodrug Drugs 0.000 claims abstract description 24
• 239000000651 prodrug Substances 0.000 claims abstract description 24
• 125000006413 ring segment Chemical group 0.000 claims abstract description 24
• 102000005741 Metalloproteases Human genes 0.000 claims abstract description 23
• 108010006035 Metalloproteases Proteins 0.000 claims abstract description 23
• 239000012453 solvate Substances 0.000 claims abstract description 22
• 125000003118 aryl group Chemical group 0.000 claims abstract description 21
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 21
• 238000011282 treatment Methods 0.000 claims abstract description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 15
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 10
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims abstract description 8
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
• -1 2-pyrimidinyl-СНСН»- Chemical group 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 201000008482 osteoarthritis Diseases 0.000 claims description 10
• 238000002560 therapeutic procedure Methods 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
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• 239000011737 fluorine Substances 0.000 claims description 5
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• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 150000008064 anhydrides Chemical class 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
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• 229910052796 boron Inorganic materials 0.000 claims description 3
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• 238000006170 formylation reaction Methods 0.000 claims description 3
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• 238000012876 topography Methods 0.000 claims 1
• 230000008569 process Effects 0.000 abstract description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 36
• 239000003112 inhibitor Substances 0.000 description 34
• 239000007787 solid Substances 0.000 description 30
• 239000000243 solution Substances 0.000 description 29
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000011541 reaction mixture Substances 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
• 238000005481 NMR spectroscopy Methods 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000000203 mixture Substances 0.000 description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• 229960002424 collagenase Drugs 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
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• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
• 102100027995 Collagenase 3 Human genes 0.000 description 8
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
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• 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
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• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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