TW546293B - Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses, and methods and intermediates useful for their preparation - Google Patents

Info

Publication number

TW546293B

TW546293B TW086100726A TW86100726A TW546293B TW 546293 B TW546293 B TW 546293B TW 086100726 A TW086100726 A TW 086100726A TW 86100726 A TW86100726 A TW 86100726A TW 546293 B TW546293 B TW 546293B

Authority

TW

Taiwan

Prior art keywords

compound

formula

salt

group

scope

Prior art date

1995-12-08

Links

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• 238000000034 method Methods 0.000 title claims abstract description 93
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
• 239000000543 intermediate Substances 0.000 title abstract description 17
• 238000002360 preparation method Methods 0.000 title description 14
• 239000003475 metalloproteinase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 312
• 150000003839 salts Chemical class 0.000 claims abstract description 158
• 125000001424 substituent group Chemical group 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 230000000694 effects Effects 0.000 claims abstract description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
• 102000005741 Metalloproteases Human genes 0.000 claims abstract description 5
• 108010006035 Metalloproteases Proteins 0.000 claims abstract description 5
• -1 carrier Substances 0.000 claims description 187
• 239000000126 substance Substances 0.000 claims description 179
• 238000011049 filling Methods 0.000 claims description 109
• 238000006243 chemical reaction Methods 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 55
• 230000002079 cooperative effect Effects 0.000 claims description 55
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
• 239000000460 chlorine Substances 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 150000001412 amines Chemical class 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 239000007789 gas Substances 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 229910052710 silicon Inorganic materials 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 5
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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• 150000002367 halogens Chemical class 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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• 125000002883 imidazolyl group Chemical group 0.000 claims 7
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
• 230000001105 regulatory effect Effects 0.000 claims 2
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• RKMZTRDJSKGOCM-UHFFFAOYSA-N 1-chloro-4-phenylsulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=CC=C1 RKMZTRDJSKGOCM-UHFFFAOYSA-N 0.000 claims 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
• 102100037651 AP-2 complex subunit sigma Human genes 0.000 claims 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• 101000806914 Homo sapiens AP-2 complex subunit sigma Proteins 0.000 claims 1
• 101001061911 Homo sapiens Ras-related protein Rab-40A Proteins 0.000 claims 1
• 102100029553 Ras-related protein Rab-40A Human genes 0.000 claims 1
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 1
• 125000000304 alkynyl group Chemical group 0.000 claims 1
• 150000001768 cations Chemical class 0.000 claims 1
• 238000012937 correction Methods 0.000 claims 1
• 150000003949 imides Chemical class 0.000 claims 1
• 238000003754 machining Methods 0.000 claims 1
• 238000012986 modification Methods 0.000 claims 1
• 230000004048 modification Effects 0.000 claims 1
• 210000003205 muscle Anatomy 0.000 claims 1
• 238000012856 packing Methods 0.000 claims 1
• 125000005630 sialyl group Chemical group 0.000 claims 1
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
• 235000021286 stilbenes Nutrition 0.000 claims 1
• 230000001755 vocal effect Effects 0.000 claims 1
• 239000002023 wood Substances 0.000 claims 1
• 239000012453 solvate Substances 0.000 abstract description 52
• 125000003118 aryl group Chemical group 0.000 abstract description 32
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 20
• 239000000651 prodrug Substances 0.000 abstract description 17
• 229940002612 prodrug Drugs 0.000 abstract description 17
• 230000002401 inhibitory effect Effects 0.000 abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 abstract description 4
• 125000006413 ring segment Chemical group 0.000 abstract description 4
• 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
• 125000005842 heteroatom Chemical group 0.000 abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 316
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• 239000000243 solution Substances 0.000 description 165
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
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• 238000004458 analytical method Methods 0.000 description 48
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• 239000012267 brine Substances 0.000 description 33
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