CA2529468A1 - N-{[4-substituted piperazine-1-sulfonylmethyl]alkyl}-n-hydroxyfomamide compounds as metalloproteinase inhibitors - Google Patents
N-{[4-substituted piperazine-1-sulfonylmethyl]alkyl}-n-hydroxyfomamide compounds as metalloproteinase inhibitors Download PDFInfo
- Publication number
- CA2529468A1 CA2529468A1 CA002529468A CA2529468A CA2529468A1 CA 2529468 A1 CA2529468 A1 CA 2529468A1 CA 002529468 A CA002529468 A CA 002529468A CA 2529468 A CA2529468 A CA 2529468A CA 2529468 A1 CA2529468 A1 CA 2529468A1
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- Canada
- Prior art keywords
- compound
- ring
- formula
- pharmaceutically acceptable
- prodrug
- 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.)
- Abandoned
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- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 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
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 22
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 22
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 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
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract 2
- -1 hydroxyamino compound Chemical class 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
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- 201000010099 disease Diseases 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 201000008482 osteoarthritis Diseases 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
- 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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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
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- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 38
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
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- 235000019439 ethyl acetate Nutrition 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 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
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- 229940088598 enzyme Drugs 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 7
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 7
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 7
- 239000012047 saturated solution Substances 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
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- WALAUUPXCVODID-UHFFFAOYSA-N 1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]piperazine Chemical compound C1=CC(OC(F)(F)C(F)F)=CC=C1N1CCNCC1 WALAUUPXCVODID-UHFFFAOYSA-N 0.000 description 3
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- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
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- 229940023080 viracept Drugs 0.000 description 1
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- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 1
- 229960001095 xylometazoline hydrochloride Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-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
- C07D309/04—Heterocyclic compounds containing six-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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- 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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0301922-1 | 2003-06-27 | ||
| SE0301922A SE0301922D0 (sv) | 2003-06-27 | 2003-06-27 | Novel compounds |
| PCT/GB2004/002702 WO2005000822A1 (en) | 2003-06-27 | 2004-06-23 | N-{‘4-substituted piperazine-1-sulfonylmethyl!alkyl}-n-hydroxyfomamide compounds as metalloproteinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2529468A1 true CA2529468A1 (en) | 2005-01-06 |
Family
ID=27656653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002529468A Abandoned CA2529468A1 (en) | 2003-06-27 | 2004-06-23 | N-{[4-substituted piperazine-1-sulfonylmethyl]alkyl}-n-hydroxyfomamide compounds as metalloproteinase inhibitors |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7485644B2 (OSRAM) |
| EP (1) | EP1644340B1 (OSRAM) |
| JP (1) | JP4701167B2 (OSRAM) |
| KR (1) | KR20060026440A (OSRAM) |
| CN (2) | CN102229589A (OSRAM) |
| AR (1) | AR044931A1 (OSRAM) |
| AT (1) | ATE414063T1 (OSRAM) |
| AU (1) | AU2004251104B2 (OSRAM) |
| BR (1) | BRPI0411929A (OSRAM) |
| CA (1) | CA2529468A1 (OSRAM) |
| CO (1) | CO5650254A2 (OSRAM) |
| CY (1) | CY1108757T1 (OSRAM) |
| DE (1) | DE602004017733D1 (OSRAM) |
| DK (1) | DK1644340T3 (OSRAM) |
| ES (1) | ES2315675T3 (OSRAM) |
| HR (1) | HRP20090009T3 (OSRAM) |
| IL (1) | IL172615A0 (OSRAM) |
| IS (1) | IS8257A (OSRAM) |
| MX (1) | MXPA05013460A (OSRAM) |
| MY (1) | MY138680A (OSRAM) |
| NO (1) | NO20060444L (OSRAM) |
| NZ (1) | NZ544208A (OSRAM) |
| PL (1) | PL1644340T3 (OSRAM) |
| PT (1) | PT1644340E (OSRAM) |
| RU (1) | RU2351595C2 (OSRAM) |
| SA (1) | SA04250224B1 (OSRAM) |
| SE (1) | SE0301922D0 (OSRAM) |
| SI (1) | SI1644340T1 (OSRAM) |
| TW (1) | TW200524898A (OSRAM) |
| UA (1) | UA81491C2 (OSRAM) |
| UY (1) | UY28387A1 (OSRAM) |
| WO (1) | WO2005000822A1 (OSRAM) |
| ZA (1) | ZA200510458B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0427403D0 (en) | 2004-12-15 | 2005-01-19 | Astrazeneca Ab | Novel compounds I |
| RS52229B (sr) * | 2005-10-26 | 2012-10-31 | Merck Serono Sa. | Derivati sulfonamida i njihova upotreba za modulaciju metaloproteinaza |
| CN101007794B (zh) * | 2006-01-26 | 2010-09-01 | 中国科学院上海药物研究所 | N,n'-二取代哌嗪类衍生物及其制备方法、药物组合物和用途 |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| KR101822444B1 (ko) * | 2010-07-08 | 2018-01-26 | 가켄 세이야쿠 가부시키가이샤 | N-히드록시포름아미드 유도체 및 그를 함유하는 의약 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL200418B1 (pl) * | 1998-01-30 | 2009-01-30 | Darwin Discovery Ltd | Pochodna N-hydroksyformamidu, zawierający ją środek farmaceutyczny i jej zastosowanie |
| GB9919776D0 (en) * | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| KR20020005769A (ko) * | 1999-06-04 | 2002-01-17 | 다비드 에 질레스 | 메탈로프로테이나제의 억제제 |
| MXPA02008111A (es) * | 2000-02-21 | 2002-11-29 | Astrazeneca Ab | N-hidroxiformamidas substituidas con piperidina y piperazina como inhibidores de metaloproteinasas. |
| GB0119472D0 (en) * | 2001-08-09 | 2001-10-03 | Astrazeneca Ab | Compounds |
| BR0309671A (pt) * | 2002-04-25 | 2005-05-03 | Pharmacia Corp | ácidos de piperidinil- e piperazinil-sulfonilmetil hidroxâmicos e seu uso como inibidores de protease |
| JP2006527754A (ja) * | 2003-06-19 | 2006-12-07 | セルテック アール アンド ディ リミテッド | Ｃｄ２３分断阻害物質としてのヒドロキサム酸スルホンアミド |
-
2003
- 2003-06-27 SE SE0301922A patent/SE0301922D0/xx unknown
-
2004
- 2004-06-23 NZ NZ544208A patent/NZ544208A/en unknown
- 2004-06-23 DE DE602004017733T patent/DE602004017733D1/de not_active Expired - Lifetime
- 2004-06-23 DK DK04743053T patent/DK1644340T3/da active
- 2004-06-23 CA CA002529468A patent/CA2529468A1/en not_active Abandoned
- 2004-06-23 PL PL04743053T patent/PL1644340T3/pl unknown
- 2004-06-23 PT PT04743053T patent/PT1644340E/pt unknown
- 2004-06-23 ES ES04743053T patent/ES2315675T3/es not_active Expired - Lifetime
- 2004-06-23 WO PCT/GB2004/002702 patent/WO2005000822A1/en not_active Ceased
- 2004-06-23 MX MXPA05013460A patent/MXPA05013460A/es active IP Right Grant
- 2004-06-23 EP EP04743053A patent/EP1644340B1/en not_active Expired - Lifetime
- 2004-06-23 AU AU2004251104A patent/AU2004251104B2/en not_active Ceased
- 2004-06-23 HR HR20090009T patent/HRP20090009T3/xx unknown
- 2004-06-23 RU RU2005141058/04A patent/RU2351595C2/ru not_active IP Right Cessation
- 2004-06-23 AT AT04743053T patent/ATE414063T1/de active
- 2004-06-23 JP JP2006516467A patent/JP4701167B2/ja not_active Expired - Fee Related
- 2004-06-23 CN CN201110103041XA patent/CN102229589A/zh active Pending
- 2004-06-23 SI SI200430979T patent/SI1644340T1/sl unknown
- 2004-06-23 BR BRPI0411929-0A patent/BRPI0411929A/pt not_active IP Right Cessation
- 2004-06-23 UA UAA200511723A patent/UA81491C2/uk unknown
- 2004-06-23 CN CN2004800182447A patent/CN1812974B/zh not_active Expired - Fee Related
- 2004-06-23 US US10/561,747 patent/US7485644B2/en not_active Expired - Fee Related
- 2004-06-23 KR KR1020057024709A patent/KR20060026440A/ko not_active Abandoned
- 2004-06-25 TW TW093118692A patent/TW200524898A/zh unknown
- 2004-06-25 UY UY28387A patent/UY28387A1/es unknown
- 2004-06-25 MY MYPI20042517A patent/MY138680A/en unknown
- 2004-06-25 AR ARP040102258A patent/AR044931A1/es not_active Application Discontinuation
- 2004-07-14 SA SA04250224A patent/SA04250224B1/ar unknown
-
2005
- 2005-12-15 IL IL172615A patent/IL172615A0/en unknown
- 2005-12-22 ZA ZA200510458A patent/ZA200510458B/xx unknown
- 2005-12-27 CO CO05130352A patent/CO5650254A2/es not_active Application Discontinuation
-
2006
- 2006-01-23 IS IS8257A patent/IS8257A/is unknown
- 2006-01-27 NO NO20060444A patent/NO20060444L/no not_active Application Discontinuation
-
2009
- 2009-01-19 CY CY20091100064T patent/CY1108757T1/el unknown
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| EEER | Examination request | ||
| FZDE | Discontinued |
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