CA2358951C - Reverse hydroxamate inhibitors of matrix metalloproteinases - Google Patents
Reverse hydroxamate inhibitors of matrix metalloproteinases Download PDFInfo
- Publication number
- CA2358951C CA2358951C CA002358951A CA2358951A CA2358951C CA 2358951 C CA2358951 C CA 2358951C CA 002358951 A CA002358951 A CA 002358951A CA 2358951 A CA2358951 A CA 2358951A CA 2358951 C CA2358951 C CA 2358951C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- sulfonyl
- ethyl
- hydroxy
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 18
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 18
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 241000124008 Mammalia Species 0.000 claims abstract description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- -1 (2) pyridyl Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- IVPPTWCRAFCOFJ-RBUKOAKNSA-N n-[(1r)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1[C@@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 IVPPTWCRAFCOFJ-RBUKOAKNSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- QHWFBRKAHGUTSR-QZTJIDSGSA-N n-[(1s)-1-[(4s)-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound C([C@@H](N(C=O)O)[C@@H]1OCOC1)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 QHWFBRKAHGUTSR-QZTJIDSGSA-N 0.000 claims description 4
- BNQGGAIQTBMHAS-WOJBJXKFSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-(4-methylphenoxy)phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound C1=CC(C)=CC=C1OC1=CC=C(S(=O)(=O)C[C@H]([C@@H]2OC(C)(C)OC2)N(O)C=O)C=C1 BNQGGAIQTBMHAS-WOJBJXKFSA-N 0.000 claims description 4
- IVPPTWCRAFCOFJ-RTBURBONSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 IVPPTWCRAFCOFJ-RTBURBONSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 229920001774 Perfluoroether Polymers 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- IVPPTWCRAFCOFJ-MOPGFXCFSA-N n-[(1s)-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 IVPPTWCRAFCOFJ-MOPGFXCFSA-N 0.000 claims description 3
- GHNFIEFTLKIWRR-WOJBJXKFSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-(4-methoxyphenoxy)phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(S(=O)(=O)C[C@H]([C@@H]2OC(C)(C)OC2)N(O)C=O)C=C1 GHNFIEFTLKIWRR-WOJBJXKFSA-N 0.000 claims description 3
- HXMWOWBOGJLNLO-FGZHOGPDSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(2-methoxyethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound C1=CC(OCCOC)=CC=C1OC1=CC=C(S(=O)(=O)C[C@H]([C@@H]2OC(C)(C)OC2)N(O)C=O)C=C1 HXMWOWBOGJLNLO-FGZHOGPDSA-N 0.000 claims description 3
- XHYQBLJNQWTIPV-FGZHOGPDSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(2-methoxyethoxy)phenyl]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical group C1=CC(OCCOC)=CC=C1C1=CC=C(S(=O)(=O)C[C@H]([C@@H]2OC(C)(C)OC2)N(O)C=O)C=C1 XHYQBLJNQWTIPV-FGZHOGPDSA-N 0.000 claims description 3
- UNMLQCGBASEIGL-RTBURBONSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethyl)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 UNMLQCGBASEIGL-RTBURBONSA-N 0.000 claims description 3
- RIILAPUTPGXTPT-RTBURBONSA-N n-[(1s)-2-[4-(4-chlorophenyl)phenyl]sulfonyl-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical group O1C(C)(C)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 RIILAPUTPGXTPT-RTBURBONSA-N 0.000 claims description 3
- QYMSAHRHXPUNSA-RTBURBONSA-N n-hydroxy-n-[(1s)-1-[(2r)-oxolan-2-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]formamide Chemical compound C([C@@H](N(C=O)O)[C@@H]1OCCC1)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 QYMSAHRHXPUNSA-RTBURBONSA-N 0.000 claims description 3
- NBFRRVUXCCCJQJ-TZHYSIJRSA-N n-hydroxy-n-[1-[(4s)-2-oxo-1,3-oxazolidin-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]formamide Chemical compound O=CN(O)C([C@@H]1NC(=O)OC1)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 NBFRRVUXCCCJQJ-TZHYSIJRSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- MTYCIOUNOCYLSE-WOJBJXKFSA-N n-hydroxy-n-[(1s)-1-[(2r)-1-methylsulfonylpyrrolidin-2-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]formamide Chemical compound CS(=O)(=O)N1CCC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 MTYCIOUNOCYLSE-WOJBJXKFSA-N 0.000 claims description 2
- MADHDOFOKLNEJA-QNSVNVJESA-N n-hydroxy-n-[1-[(4s)-3-methyl-2-oxo-1,3-oxazolidin-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]formamide Chemical compound C1OC(=O)N(C)[C@H]1C(N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 MADHDOFOKLNEJA-QNSVNVJESA-N 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 2
- IVPPTWCRAFCOFJ-OALUTQOASA-N n-[(1r)-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@H]1[C@@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 IVPPTWCRAFCOFJ-OALUTQOASA-N 0.000 claims 2
- PIPNMGRIVITFEC-NHCUHLMSSA-N n-[(1s)-1-[(4s)-2,2-diethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical compound O1C(CC)(CC)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 PIPNMGRIVITFEC-NHCUHLMSSA-N 0.000 claims 2
- SDGGLYZVXPJDKA-RTBURBONSA-N n-[(1s)-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[4-[4-(trifluoromethyl)phenyl]phenyl]sulfonylethyl]-n-hydroxyformamide Chemical group O1C(C)(C)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 SDGGLYZVXPJDKA-RTBURBONSA-N 0.000 claims 2
- HVWJQCZUHMDVAI-RTBURBONSA-N n-[(1s)-2-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]-n-hydroxyformamide Chemical compound O1C(C)(C)OC[C@@H]1[C@H](N(O)C=O)CS(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 HVWJQCZUHMDVAI-RTBURBONSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- QYMSAHRHXPUNSA-RBUKOAKNSA-N n-hydroxy-n-[(1r)-1-[(2r)-oxolan-2-yl]-2-[4-[4-(trifluoromethoxy)phenoxy]phenyl]sulfonylethyl]formamide Chemical compound C([C@H](N(C=O)O)[C@@H]1OCCC1)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 QYMSAHRHXPUNSA-RBUKOAKNSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 31
- 238000000034 method Methods 0.000 abstract description 22
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 13
- 235000008504 concentrate Nutrition 0.000 description 13
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- DOWWCCDWPKGNGX-RXMQYKEDSA-N methyl (4r)-2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1COC(C)(C)O1 DOWWCCDWPKGNGX-RXMQYKEDSA-N 0.000 description 8
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- 125000005843 halogen group Chemical group 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
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- WDRJNKMAZMEYOF-UHFFFAOYSA-N 4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1 WDRJNKMAZMEYOF-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23908799A | 1999-01-27 | 1999-01-27 | |
| US09/239,087 | 1999-01-27 | ||
| PCT/US2000/002038 WO2000044739A1 (en) | 1999-01-27 | 2000-01-27 | Reverse hydroxamate inhibitors of matrix metalloproteinases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2358951A1 CA2358951A1 (en) | 2000-08-03 |
| CA2358951C true CA2358951C (en) | 2009-10-20 |
Family
ID=22900549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002358951A Expired - Fee Related CA2358951C (en) | 1999-01-27 | 2000-01-27 | Reverse hydroxamate inhibitors of matrix metalloproteinases |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20020007060A1 (enExample) |
| EP (1) | EP1147101B1 (enExample) |
| JP (1) | JP4718686B2 (enExample) |
| KR (1) | KR100748010B1 (enExample) |
| CN (1) | CN1222519C (enExample) |
| AR (1) | AR029329A1 (enExample) |
| AT (1) | ATE228122T1 (enExample) |
| AU (1) | AU764383B2 (enExample) |
| BG (1) | BG105782A (enExample) |
| BR (1) | BR0007278A (enExample) |
| CA (1) | CA2358951C (enExample) |
| CO (1) | CO5150194A1 (enExample) |
| CZ (1) | CZ20012591A3 (enExample) |
| DE (1) | DE60000819T2 (enExample) |
| DK (1) | DK1147101T3 (enExample) |
| ES (1) | ES2187443T3 (enExample) |
| HK (1) | HK1043115A1 (enExample) |
| HU (1) | HUP0105477A2 (enExample) |
| IL (1) | IL143713A0 (enExample) |
| NO (1) | NO20013669L (enExample) |
| NZ (1) | NZ512372A (enExample) |
| PL (1) | PL349771A1 (enExample) |
| PT (1) | PT1147101E (enExample) |
| SK (1) | SK10582001A3 (enExample) |
| TR (1) | TR200102159T2 (enExample) |
| TW (1) | TWI225486B (enExample) |
| WO (1) | WO2000044739A1 (enExample) |
| ZA (1) | ZA200104979B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9923078D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| AU2001298065A1 (en) * | 2001-01-12 | 2003-09-02 | Abbott Laboratories | Process for the preparation of matrix metalloproteinase inhibitors |
| EP1431285B1 (en) | 2001-09-07 | 2009-01-07 | Kaken Pharmaceutical Co., Ltd. | Reverse hydroxamic acid derivatives |
| EP1896404B1 (en) * | 2005-06-27 | 2014-09-17 | Nabriva Therapeutics AG | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
| US20110015158A1 (en) | 2007-12-11 | 2011-01-20 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| WO2015107139A1 (en) | 2014-01-17 | 2015-07-23 | Proyecto De Biomedicina Cima, S.L. | Compounds for use as antifibrinolytic agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780386B1 (en) * | 1995-12-20 | 2002-10-02 | F. Hoffmann-La Roche Ag | Matrix metalloprotease inhibitors |
-
2000
- 2000-01-25 CO CO00003867A patent/CO5150194A1/es unknown
- 2000-01-26 AR ARP000100349A patent/AR029329A1/es not_active Application Discontinuation
- 2000-01-27 ES ES00905758T patent/ES2187443T3/es not_active Expired - Lifetime
- 2000-01-27 SK SK1058-2001A patent/SK10582001A3/sk unknown
- 2000-01-27 WO PCT/US2000/002038 patent/WO2000044739A1/en not_active Ceased
- 2000-01-27 CZ CZ20012591A patent/CZ20012591A3/cs unknown
- 2000-01-27 TR TR2001/02159T patent/TR200102159T2/xx unknown
- 2000-01-27 PT PT00905758T patent/PT1147101E/pt unknown
- 2000-01-27 NZ NZ512372A patent/NZ512372A/xx unknown
- 2000-01-27 AU AU27391/00A patent/AU764383B2/en not_active Ceased
- 2000-01-27 EP EP00905758A patent/EP1147101B1/en not_active Expired - Lifetime
- 2000-01-27 HK HK02102947.8A patent/HK1043115A1/zh unknown
- 2000-01-27 CA CA002358951A patent/CA2358951C/en not_active Expired - Fee Related
- 2000-01-27 CN CNB008032378A patent/CN1222519C/zh not_active Expired - Fee Related
- 2000-01-27 JP JP2000595995A patent/JP4718686B2/ja not_active Expired - Fee Related
- 2000-01-27 DK DK00905758T patent/DK1147101T3/da active
- 2000-01-27 HU HU0105477A patent/HUP0105477A2/hu unknown
- 2000-01-27 IL IL14371300A patent/IL143713A0/xx unknown
- 2000-01-27 KR KR1020017009393A patent/KR100748010B1/ko not_active Expired - Fee Related
- 2000-01-27 PL PL00349771A patent/PL349771A1/xx not_active Application Discontinuation
- 2000-01-27 DE DE60000819T patent/DE60000819T2/de not_active Expired - Lifetime
- 2000-01-27 AT AT00905758T patent/ATE228122T1/de not_active IP Right Cessation
- 2000-01-27 BR BR0007278-8A patent/BR0007278A/pt not_active Application Discontinuation
- 2000-02-25 TW TW089101383A patent/TWI225486B/zh not_active IP Right Cessation
-
2001
- 2001-06-18 ZA ZA200104979A patent/ZA200104979B/en unknown
- 2001-07-16 US US09/905,242 patent/US20020007060A1/en not_active Abandoned
- 2001-07-26 NO NO20013669A patent/NO20013669L/no not_active Application Discontinuation
- 2001-08-03 BG BG105782A patent/BG105782A/xx unknown
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130128 |