CN1202161A - 作为金属蛋白酶抑制剂的新的大环化合物 - Google Patents
作为金属蛋白酶抑制剂的新的大环化合物 Download PDFInfo
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- CN1202161A CN1202161A CN96198327A CN96198327A CN1202161A CN 1202161 A CN1202161 A CN 1202161A CN 96198327 A CN96198327 A CN 96198327A CN 96198327 A CN96198327 A CN 96198327A CN 1202161 A CN1202161 A CN 1202161A
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- Prior art keywords
- alkyl
- aryl
- oxa
- hydroxy
- oxo
- Prior art date
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- 150000002678 macrocyclic compounds Chemical class 0.000 title description 4
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 248
- 238000000034 method Methods 0.000 claims abstract description 86
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- -1 N-methylimidazolyl Chemical group 0.000 claims description 278
- 125000003118 aryl group Chemical group 0.000 claims description 249
- 239000002253 acid Substances 0.000 claims description 185
- 125000000217 alkyl group Chemical group 0.000 claims description 185
- 229910052739 hydrogen Inorganic materials 0.000 claims description 142
- 229910052736 halogen Inorganic materials 0.000 claims description 121
- 150000002367 halogens Chemical class 0.000 claims description 121
- 125000003545 alkoxy group Chemical group 0.000 claims description 119
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 118
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 113
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 91
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 89
- 125000003368 amide group Chemical group 0.000 claims description 87
- 125000004414 alkyl thio group Chemical group 0.000 claims description 86
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 64
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 62
- 229910052799 carbon Inorganic materials 0.000 claims description 59
- 150000001408 amides Chemical class 0.000 claims description 50
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000002883 imidazolyl group Chemical group 0.000 claims description 46
- 125000001544 thienyl group Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 40
- 125000005110 aryl thio group Chemical group 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 40
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 40
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 40
- 125000004429 atom Chemical group 0.000 claims description 38
- 108010000170 beta-lactamase OXA-14 Proteins 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
- 239000004471 Glycine Substances 0.000 claims description 32
- 239000000651 prodrug Substances 0.000 claims description 31
- 229940002612 prodrug Drugs 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 24
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 206010061218 Inflammation Diseases 0.000 claims description 21
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 230000004054 inflammatory process Effects 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 20
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 20
- 125000001769 aryl amino group Chemical group 0.000 claims description 20
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 20
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 20
- 229940124530 sulfonamide Drugs 0.000 claims description 20
- 125000005518 carboxamido group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 16
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 claims description 14
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 claims description 14
- 229960002646 scopolamine Drugs 0.000 claims description 14
- 108010067219 Aggrecans Proteins 0.000 claims description 13
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 13
- 208000032820 Ring chromosome 13 syndrome Diseases 0.000 claims description 12
- OSOIQJGOYGSIMF-UHFFFAOYSA-N Cyclopenta-decanone Natural products O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 claims description 10
- 241001597008 Nomeidae Species 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 10
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 210000000845 cartilage Anatomy 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 8
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical compound ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 claims description 8
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 8
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 102000016611 Proteoglycans Human genes 0.000 claims description 5
- 108010067787 Proteoglycans Proteins 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- CKQYFZPCICOPMQ-GSVOUGTGSA-N (2r)-2-amino-n-methylpropanamide Chemical compound CNC(=O)[C@@H](C)N CKQYFZPCICOPMQ-GSVOUGTGSA-N 0.000 claims description 4
- LIBDTAYIDBPBRN-LURJTMIESA-N (2s)-2-amino-n,4-dimethylpentanamide Chemical compound CNC(=O)[C@@H](N)CC(C)C LIBDTAYIDBPBRN-LURJTMIESA-N 0.000 claims description 4
- CKQYFZPCICOPMQ-VKHMYHEASA-N (2s)-2-amino-n-methylpropanamide Chemical compound CNC(=O)[C@H](C)N CKQYFZPCICOPMQ-VKHMYHEASA-N 0.000 claims description 4
- UUYDPHCMCYSNAY-UHFFFAOYSA-N 2-amino-n-methylacetamide Chemical compound CNC(=O)CN UUYDPHCMCYSNAY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- PJZBXYKLDPBGFD-GSVOUGTGSA-N (2R)-2-amino-3-hydroxy-N-methylpropanamide Chemical compound CNC(=O)[C@H](N)CO PJZBXYKLDPBGFD-GSVOUGTGSA-N 0.000 claims description 2
- KSYTYCZOPVNULI-YFKPBYRVSA-N (2s)-2,5-diamino-n-methylpentanamide Chemical compound CNC(=O)[C@@H](N)CCCN KSYTYCZOPVNULI-YFKPBYRVSA-N 0.000 claims description 2
- PZVHMLQLXAUQGY-LURJTMIESA-N (2s)-2,6-diamino-n-methylhexanamide Chemical compound CNC(=O)[C@@H](N)CCCCN PZVHMLQLXAUQGY-LURJTMIESA-N 0.000 claims description 2
- PJZBXYKLDPBGFD-VKHMYHEASA-N (2s)-2-amino-3-hydroxy-n-methylpropanamide Chemical compound CNC(=O)[C@@H](N)CO PJZBXYKLDPBGFD-VKHMYHEASA-N 0.000 claims description 2
- OKTIZBDONHCJEL-YFKPBYRVSA-N (2s)-2-amino-n,3-dimethylbutanamide Chemical compound CNC(=O)[C@@H](N)C(C)C OKTIZBDONHCJEL-YFKPBYRVSA-N 0.000 claims description 2
- KNVRBEGQERGQRP-UHFFFAOYSA-N 2-amino-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CN KNVRBEGQERGQRP-UHFFFAOYSA-N 0.000 claims description 2
- FWHFRDUWGWUPOC-UHFFFAOYSA-N 2-amino-n-pyridin-2-ylacetamide Chemical compound NCC(=O)NC1=CC=CC=N1 FWHFRDUWGWUPOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- BFJOJIJWHRDGQO-UHFFFAOYSA-N 3-amino-n-methylpropanamide Chemical compound CNC(=O)CCN BFJOJIJWHRDGQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 2
- 208000032822 Ring chromosome 11 syndrome Diseases 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
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- 230000000452 restraining effect Effects 0.000 claims description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 47
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 claims 10
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/02—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
- C07D255/02—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
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- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
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- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
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Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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US668495P | 1995-11-14 | 1995-11-14 | |
US60/006,684 | 1995-11-14 | ||
US64690296A | 1996-05-08 | 1996-05-08 | |
US60/646,902 | 1996-05-08 | ||
US74343996A | 1996-11-01 | 1996-11-01 | |
US08/743,439 | 1996-11-01 |
Publications (1)
Publication Number | Publication Date |
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CN1202161A true CN1202161A (zh) | 1998-12-16 |
Family
ID=27358171
Family Applications (1)
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CN96198327A Pending CN1202161A (zh) | 1995-11-14 | 1996-11-13 | 作为金属蛋白酶抑制剂的新的大环化合物 |
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EP (1) | EP0863885A2 (et) |
JP (1) | JP2000502050A (et) |
CN (1) | CN1202161A (et) |
BR (1) | BR9611563A (et) |
CA (1) | CA2237524A1 (et) |
CZ (1) | CZ144798A3 (et) |
EE (1) | EE9800115A (et) |
HR (1) | HRP960533A2 (et) |
HU (1) | HUP0201479A2 (et) |
IL (1) | IL124366A0 (et) |
LV (1) | LV12167B (et) |
MX (1) | MX9803851A (et) |
NO (1) | NO982185L (et) |
PL (1) | PL326714A1 (et) |
SI (1) | SI9620120A (et) |
SK (1) | SK63498A3 (et) |
WO (1) | WO1997018207A2 (et) |
Cited By (3)
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---|---|---|---|---|
CN102276546A (zh) * | 2011-05-31 | 2011-12-14 | 中国科学院广州生物医药与健康研究院 | 用作蛋白聚糖酶调节剂的化合物及其应用 |
CN103748099A (zh) * | 2011-05-19 | 2014-04-23 | 西班牙国家癌症研究中心 | 作为蛋白激酶抑制剂的大环化合物 |
CN108623530A (zh) * | 2016-09-18 | 2018-10-09 | 广西师范大学 | 1,2,8-氧代二氮杂环壬-9-硫酮衍生物及其合成方法和应用 |
Families Citing this family (29)
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US6281352B1 (en) | 1995-11-14 | 2001-08-28 | Dupont Pharmaceuticals Company | Macrocyclic compounds as metalloprotease inhibitors |
ZA9820B (en) * | 1997-01-07 | 1998-07-02 | Abbott Lab | Macrocyclic inhibitors of matrix metalloproteinases and tnf x secretion |
US5985911A (en) * | 1997-01-07 | 1999-11-16 | Abbott Laboratories | C-terminal ketone inhibitors of matrix metalloproteinases and TNFα secretion |
US5952320A (en) * | 1997-01-07 | 1999-09-14 | Abbott Laboratories | Macrocyclic inhibitors of matrix metalloproteinases and TNFα secretion |
US6548663B1 (en) | 1998-03-31 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Benzodiazepine vitronectin receptor antagonist pharmaceuticals |
US6537520B1 (en) | 1998-03-31 | 2003-03-25 | Bristol-Myers Squibb Pharma Company | Pharmaceuticals for the imaging of angiogenic disorders |
BR9909420A (pt) | 1998-03-31 | 2001-09-25 | Du Pont Pharm Co | Composto, kit, composição metalofarmacêutica de diagnóstico ou terapêutica, composição de agente de contraste de ultrassom, composição radiofarmacêutica terapêutica e composição radiofarmacêutica de diagnóstico |
US6524553B2 (en) | 1998-03-31 | 2003-02-25 | Bristol-Myers Squibb Pharma Company | Quinolone vitronectin receptor antagonist pharmaceuticals |
CA2333551A1 (en) | 1998-06-11 | 1999-12-16 | Zhe Wang | A process for the preparation of macrocyclic metalloprotease inhibitors |
HRP990246A2 (en) | 1998-08-07 | 2000-06-30 | Du Pont Pharm Co | Succinoylamino benzodiazepines as inhibitors of a beta protein production |
NZ525513A (en) | 1998-08-07 | 2004-09-24 | Pont Pharmaceuticals Du | Succinoylamino lactams as inhibitors of Abeta protein production |
US6794518B1 (en) | 1998-12-18 | 2004-09-21 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
US6288261B1 (en) | 1998-12-18 | 2001-09-11 | Abbott Laboratories | Inhibitors of matrix metalloproteinases |
CN1356913A (zh) | 1998-12-18 | 2002-07-03 | 杜邦药品公司 | 玻连蛋白受体拮抗剂药物 |
US6511649B1 (en) | 1998-12-18 | 2003-01-28 | Thomas D. Harris | Vitronectin receptor antagonist pharmaceuticals |
US6569402B1 (en) | 1998-12-18 | 2003-05-27 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
EP1140864A2 (en) | 1998-12-18 | 2001-10-10 | Du Pont Pharmaceuticals Company | Vitronectin receptor antagonist pharmaceuticals |
US6649377B1 (en) | 1999-05-10 | 2003-11-18 | Syntex (U.S.A.) Llc | Human aggrecanase and nucleic acid compositions encoding the same |
US6808902B1 (en) | 1999-11-12 | 2004-10-26 | Amgen Inc. | Process for correction of a disulfide misfold in IL-1Ra Fc fusion molecules |
US6989139B2 (en) * | 2000-02-15 | 2006-01-24 | Bristol-Myers Squibb Pharma Company | Matrix metalloproteinase inhibitors |
AU783857B2 (en) | 2000-06-01 | 2005-12-15 | Bristol-Myers Squibb Pharma Company | Lactams substituted by cyclic succinates as inhibitors of a beta protein production |
ATE464068T1 (de) | 2001-06-26 | 2010-04-15 | Amgen Fremont Inc | Antikörper gegen opgl |
PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
US7491794B2 (en) | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
WO2005044780A1 (ja) * | 2003-11-10 | 2005-05-19 | Kyorin Pharmaceutical Co., Ltd. | アミノカルボン酸誘導体とその付加塩及びs1p受容体調節剤 |
CA2708281A1 (en) | 2007-12-11 | 2009-08-27 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
WO2009099174A1 (ja) | 2008-02-07 | 2009-08-13 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
WO2010132494A1 (en) * | 2009-05-11 | 2010-11-18 | Ghosh Arun K | Compounds and methods for treating aids and hiv infections |
US20210393632A1 (en) | 2018-10-04 | 2021-12-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Egfr inhibitors for treating keratodermas |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9102635D0 (en) * | 1991-02-07 | 1991-03-27 | British Bio Technology | Compounds |
US5427954A (en) * | 1992-04-29 | 1995-06-27 | Shriner's Hospitals For Crippled Children | Compositions and methods for detection and treatment of human osteoarthritis |
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1996
- 1996-11-13 CN CN96198327A patent/CN1202161A/zh active Pending
- 1996-11-13 HU HU0201479A patent/HUP0201479A2/hu unknown
- 1996-11-13 SK SK634-98A patent/SK63498A3/sk unknown
- 1996-11-13 IL IL12436696A patent/IL124366A0/xx unknown
- 1996-11-13 EP EP96943497A patent/EP0863885A2/en not_active Withdrawn
- 1996-11-13 JP JP9519119A patent/JP2000502050A/ja active Pending
- 1996-11-13 HR HR08/743,439A patent/HRP960533A2/hr not_active Application Discontinuation
- 1996-11-13 PL PL96326714A patent/PL326714A1/xx unknown
- 1996-11-13 WO PCT/US1996/018382 patent/WO1997018207A2/en not_active Application Discontinuation
- 1996-11-13 BR BR9611563A patent/BR9611563A/pt not_active IP Right Cessation
- 1996-11-13 CZ CZ981447A patent/CZ144798A3/cs unknown
- 1996-11-13 EE EE9800115A patent/EE9800115A/et unknown
- 1996-11-13 SI SI9620120A patent/SI9620120A/sl unknown
- 1996-11-13 CA CA002237524A patent/CA2237524A1/en not_active Abandoned
-
1998
- 1998-05-13 NO NO982185A patent/NO982185L/no unknown
- 1998-05-14 MX MX9803851A patent/MX9803851A/es unknown
- 1998-07-07 LV LVP-98-104A patent/LV12167B/en unknown
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103748099A (zh) * | 2011-05-19 | 2014-04-23 | 西班牙国家癌症研究中心 | 作为蛋白激酶抑制剂的大环化合物 |
US9284334B2 (en) | 2011-05-19 | 2016-03-15 | Fundación Centro Nacional De Investigaciones Oncologicas Carlos Iii | Macrocyclic compounds as protein kinase inhibitors |
US9808466B2 (en) | 2011-05-19 | 2017-11-07 | Fundación Centro Nacional De Investigaciones Oncologicas Carlos Iii | Macrocyclic compounds as protein kinase inhibitors |
CN102276546A (zh) * | 2011-05-31 | 2011-12-14 | 中国科学院广州生物医药与健康研究院 | 用作蛋白聚糖酶调节剂的化合物及其应用 |
CN102276546B (zh) * | 2011-05-31 | 2014-06-25 | 中国科学院广州生物医药与健康研究院 | 用作蛋白聚糖酶调节剂的化合物及其应用 |
CN108623530A (zh) * | 2016-09-18 | 2018-10-09 | 广西师范大学 | 1,2,8-氧代二氮杂环壬-9-硫酮衍生物及其合成方法和应用 |
CN108623530B (zh) * | 2016-09-18 | 2021-05-11 | 广西师范大学 | 1,2,8-氧代二氮杂环壬-9-硫酮衍生物及其合成方法和应用 |
Also Published As
Publication number | Publication date |
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EP0863885A2 (en) | 1998-09-16 |
CA2237524A1 (en) | 1997-05-22 |
LV12167B (en) | 1999-03-20 |
SI9620120A (sl) | 1999-06-30 |
EE9800115A (et) | 1998-10-15 |
NO982185L (no) | 1998-07-13 |
JP2000502050A (ja) | 2000-02-22 |
HRP960533A2 (en) | 1998-04-30 |
WO1997018207A3 (en) | 1997-07-24 |
SK63498A3 (en) | 1999-01-11 |
HUP0201479A2 (en) | 2002-08-28 |
NO982185D0 (no) | 1998-05-13 |
IL124366A0 (en) | 1998-12-06 |
MX9803851A (es) | 1998-09-30 |
PL326714A1 (en) | 1998-10-26 |
LV12167A (lv) | 1998-11-20 |
BR9611563A (pt) | 1999-03-02 |
CZ144798A3 (cs) | 1998-10-14 |
WO1997018207A2 (en) | 1997-05-22 |
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