TW200900397A - Tricyclic compounds as matrix metalloproteinase inhibitors - Google Patents

Info

Publication number

TW200900397A

TW200900397A TW097116522A TW97116522A TW200900397A TW 200900397 A TW200900397 A TW 200900397A TW 097116522 A TW097116522 A TW 097116522A TW 97116522 A TW97116522 A TW 97116522A TW 200900397 A TW200900397 A TW 200900397A

Authority

TW

Taiwan

Prior art keywords

acid

dibenzo

furan

methyl

sulfonylamino

Prior art date

2007-05-04

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 622
• 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title 1
• 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 188
• 150000003839 salts Chemical class 0.000 claims abstract description 71
• 150000002148 esters Chemical class 0.000 claims abstract description 46
• 241000124008 Mammalia Species 0.000 claims abstract description 19
• 102100027998 Macrophage metalloelastase Human genes 0.000 claims abstract description 14
• 101710187853 Macrophage metalloelastase Proteins 0.000 claims abstract description 14
• 230000001575 pathological effect Effects 0.000 claims abstract description 14
• 102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 12
• 108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 12
• 241000282414 Homo sapiens Species 0.000 claims abstract description 5
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 462
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 373
• -1 C2 - decyl Chemical group 0.000 claims description 254
• 238000002360 preparation method Methods 0.000 claims description 175
• 125000000217 alkyl group Chemical group 0.000 claims description 168
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 115
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 112
• 239000002253 acid Substances 0.000 claims description 101
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 84
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 229940024606 amino acid Drugs 0.000 claims description 39
• 125000005605 benzo group Chemical group 0.000 claims description 35
• 239000004305 biphenyl Substances 0.000 claims description 35
• 150000001413 amino acids Chemical class 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 235000010290 biphenyl Nutrition 0.000 claims description 33
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 33
• WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 31
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000006267 biphenyl group Chemical group 0.000 claims description 25
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 150000001412 amines Chemical class 0.000 claims description 24
• 229940124530 sulfonamide Drugs 0.000 claims description 24
• 239000000052 vinegar Substances 0.000 claims description 24
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• 125000000304 alkynyl group Chemical group 0.000 claims description 22
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• 239000007789 gas Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
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• 201000010099 disease Diseases 0.000 claims description 16
• 150000001721 carbon Chemical group 0.000 claims description 15
• 125000001188 haloalkyl group Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 239000011734 sodium Substances 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 125000000468 ketone group Chemical group 0.000 claims description 12
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• 208000024891 symptom Diseases 0.000 claims description 12
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 12
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• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 10
• 229910052708 sodium Inorganic materials 0.000 claims description 10
• 150000003456 sulfonamides Chemical class 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical compound CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 claims description 8
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 8
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 8
• 206010036790 Productive cough Diseases 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
• XNTWONAICPPJDM-UHFFFAOYSA-N furan-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=COC=1 XNTWONAICPPJDM-UHFFFAOYSA-N 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 210000003802 sputum Anatomy 0.000 claims description 8
• 208000024794 sputum Diseases 0.000 claims description 8
• 229930192474 thiophene Natural products 0.000 claims description 8
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
• 125000003368 amide group Chemical group 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 7
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 201000006417 multiple sclerosis Diseases 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• 206010016654 Fibrosis Diseases 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
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• 208000020431 spinal cord injury Diseases 0.000 claims description 6
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• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 5
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
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• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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