CA2577430C - 5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2,4-dione and analogues as inhibitors of macrophage elastase - Google Patents
5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2,4-dione and analogues as inhibitors of macrophage elastase Download PDFInfo
- Publication number
- CA2577430C CA2577430C CA2577430A CA2577430A CA2577430C CA 2577430 C CA2577430 C CA 2577430C CA 2577430 A CA2577430 A CA 2577430A CA 2577430 A CA2577430 A CA 2577430A CA 2577430 C CA2577430 C CA 2577430C
- Authority
- CA
- Canada
- Prior art keywords
- mmp
- fur
- dione
- inhibitors
- methoxyphenyl
- 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
- 102100027998 Macrophage metalloelastase Human genes 0.000 title claims abstract description 19
- 239000003112 inhibitor Substances 0.000 title abstract description 16
- ZUOUZWHAINARGI-UHFFFAOYSA-N 5-[3-(4-phenylmethoxyphenyl)sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=C(SC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=CO1 ZUOUZWHAINARGI-UHFFFAOYSA-N 0.000 title abstract description 4
- 108030001712 Macrophage elastases Proteins 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 20
- 101710187853 Macrophage metalloelastase Proteins 0.000 claims description 15
- -1 4-benzyloxyphenyl Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 239000004305 biphenyl Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 7
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 150000001469 hydantoins Chemical class 0.000 description 6
- DNEVHXPXJVTGNT-UHFFFAOYSA-N 3-(4-hydroxyphenyl)furan-2-carbothialdehyde Chemical compound OC1=CC=C(C=C1)C1=C(OC=C1)C=S DNEVHXPXJVTGNT-UHFFFAOYSA-N 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 206010014561 Emphysema Diseases 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
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- 229940124761 MMP inhibitor Drugs 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
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- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KSAVZSUPQGDMRC-UHFFFAOYSA-N 3-bromofuran-2-carbaldehyde Chemical compound BrC=1C=COC=1C=O KSAVZSUPQGDMRC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
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- 239000012131 assay buffer Substances 0.000 description 2
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- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 2
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- 230000002860 competitive effect Effects 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 201000008383 nephritis Diseases 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 1
- LXWLEQZDXOQZGW-UHFFFAOYSA-N 3-bromofuran Chemical compound BrC=1C=COC=1 LXWLEQZDXOQZGW-UHFFFAOYSA-N 0.000 description 1
- DQCZQFOIDHTCKO-UHFFFAOYSA-N 5-[3-[4-[(2-chlorophenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 DQCZQFOIDHTCKO-UHFFFAOYSA-N 0.000 description 1
- UGPXGSWFLXWCSE-UHFFFAOYSA-N 5-[3-[4-[(2-methoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 UGPXGSWFLXWCSE-UHFFFAOYSA-N 0.000 description 1
- KCSIYVQRLLHGQX-UHFFFAOYSA-N 5-[3-[4-[(2-methylphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 KCSIYVQRLLHGQX-UHFFFAOYSA-N 0.000 description 1
- YMFBYMXAQABRLU-UHFFFAOYSA-N 5-[3-[4-[(3-methoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 YMFBYMXAQABRLU-UHFFFAOYSA-N 0.000 description 1
- CXEKSVVDMIAMLF-UHFFFAOYSA-N 5-[3-[4-[(3-methylphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 CXEKSVVDMIAMLF-UHFFFAOYSA-N 0.000 description 1
- PURKFSOZJRFWBT-UHFFFAOYSA-N 5-[3-[4-[(4-chlorophenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 PURKFSOZJRFWBT-UHFFFAOYSA-N 0.000 description 1
- NFWRXMHQHJJBAF-UHFFFAOYSA-N 5-[3-[4-[(4-methoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 NFWRXMHQHJJBAF-UHFFFAOYSA-N 0.000 description 1
- ZMLIWSZENMUIKD-UHFFFAOYSA-N 5-[3-[4-[(4-methylphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(C)=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 ZMLIWSZENMUIKD-UHFFFAOYSA-N 0.000 description 1
- WBCMCZQPISDDJL-UHFFFAOYSA-N 5-[3-[4-[(4-phenylmethoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=C(SC=2C=CC(OCC=3C=CC(OCC=4C=CC=CC=4)=CC=3)=CC=2)C=CO1 WBCMCZQPISDDJL-UHFFFAOYSA-N 0.000 description 1
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- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 102100030416 Stromelysin-1 Human genes 0.000 description 1
- 101710108790 Stromelysin-1 Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
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- 210000002540 macrophage Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 1
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
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- 238000010172 mouse model Methods 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60273604P | 2004-08-19 | 2004-08-19 | |
| US60/602,736 | 2004-08-19 | ||
| PCT/US2005/029259 WO2006023562A2 (en) | 2004-08-19 | 2005-08-17 | 5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2577430A1 CA2577430A1 (en) | 2006-03-02 |
| CA2577430C true CA2577430C (en) | 2010-12-07 |
Family
ID=35968136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2577430A Expired - Fee Related CA2577430C (en) | 2004-08-19 | 2005-08-17 | 5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2,4-dione and analogues as inhibitors of macrophage elastase |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7179831B2 (enExample) |
| EP (1) | EP1789036B1 (enExample) |
| JP (1) | JP5042833B2 (enExample) |
| KR (1) | KR101197325B1 (enExample) |
| CN (1) | CN101014338B (enExample) |
| AT (1) | ATE508744T1 (enExample) |
| AU (1) | AU2005277432B2 (enExample) |
| BR (1) | BRPI0514470B8 (enExample) |
| CA (1) | CA2577430C (enExample) |
| DK (1) | DK1789036T3 (enExample) |
| ES (1) | ES2364068T3 (enExample) |
| MX (1) | MX2007001940A (enExample) |
| NZ (1) | NZ553258A (enExample) |
| RU (1) | RU2391339C2 (enExample) |
| SI (1) | SI1789036T1 (enExample) |
| WO (1) | WO2006023562A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008051260A1 (en) * | 2006-01-13 | 2008-05-02 | Battelle Memorial Institute | Methods for assessing copd-retlated diseases |
| EP2907512A1 (en) | 2014-02-14 | 2015-08-19 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Inhibitors of MMP-12 as antiviral Agents |
| US10532102B2 (en) * | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
| ES2910833T3 (es) * | 2016-08-19 | 2022-05-13 | Foresee Pharmaceuticals Co Ltd | Composición farmacéutica y procedimientos de usos |
| ES2865854T3 (es) * | 2016-09-23 | 2021-10-18 | Kaken Pharma Co Ltd | Método para producir (r)-5-(3,4-difluorofenil)-5-[(3-metil-2-oxopiridin-1(2h)-il)metil]imidazolidin-2,4-diona y un producto intermedio para producir la misma |
| FI3793992T3 (fi) | 2018-05-15 | 2024-04-17 | Foresee Pharmaceuticals Usa Inc | Matriksin metalloproteinaasin (mmp) estäjiä ja niiden käyttömenetelmiä |
| DK4058437T3 (da) * | 2019-11-14 | 2025-01-20 | Foresee Pharmaceuticals Usa Inc | Matrix-metalloproteinase-(MMP)-inhibitorer og fremgangsmåder til anvendelse heraf |
| AU2022290589A1 (en) * | 2021-06-08 | 2023-11-23 | Foresee Pharmaceuticals Usa, Inc. | Safe administration of mmp-12 inhibitor |
| RU2766551C1 (ru) * | 2021-07-19 | 2022-03-15 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | 5-(4-хлорфенил)-3-((4-хлорфенил)амино)-5-(фенилтио)фуран-2(5н)-он, обладающий противомикробной активностью |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000040577A1 (en) | 1998-12-31 | 2000-07-13 | Aventis Pharmaceuticals Inc. | 1-carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of mmp-12 |
| US6352976B1 (en) * | 1998-12-31 | 2002-03-05 | Aventis Pharmaceuticals Inc. | Selective inhibitors of MMP-12 |
| RU2150469C1 (ru) * | 1999-06-01 | 2000-06-10 | Уфимский государственный нефтяной технический университет | Способ получения 2-(фурил-2)-1,3-имидазолидинов |
| EP1288199A4 (en) | 2000-04-28 | 2005-10-12 | Shionogi & Co | INHIBITORS OF MMP-12 |
| SE0100903D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| CA2447475A1 (en) | 2001-05-25 | 2002-12-05 | Chu-Biao Xue | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| EP1394159A1 (fr) * | 2002-08-13 | 2004-03-03 | Warner-Lambert Company LLC | Nouveaux dérivés de thiophène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| GB0219896D0 (en) | 2002-08-27 | 2002-10-02 | Bayer Ag | Dihydropyridine derivatives |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| US7041693B2 (en) * | 2002-10-04 | 2006-05-09 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| US7132432B2 (en) * | 2003-06-05 | 2006-11-07 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) |
-
2005
- 2005-08-17 AT AT05786673T patent/ATE508744T1/de not_active IP Right Cessation
- 2005-08-17 CA CA2577430A patent/CA2577430C/en not_active Expired - Fee Related
- 2005-08-17 WO PCT/US2005/029259 patent/WO2006023562A2/en not_active Ceased
- 2005-08-17 MX MX2007001940A patent/MX2007001940A/es active IP Right Grant
- 2005-08-17 EP EP05786673A patent/EP1789036B1/en not_active Expired - Lifetime
- 2005-08-17 DK DK05786673.3T patent/DK1789036T3/da active
- 2005-08-17 NZ NZ553258A patent/NZ553258A/en not_active IP Right Cessation
- 2005-08-17 JP JP2007527975A patent/JP5042833B2/ja not_active Expired - Fee Related
- 2005-08-17 CN CN2005800285556A patent/CN101014338B/zh not_active Expired - Fee Related
- 2005-08-17 BR BRPI0514470A patent/BRPI0514470B8/pt not_active IP Right Cessation
- 2005-08-17 ES ES05786673T patent/ES2364068T3/es not_active Expired - Lifetime
- 2005-08-17 AU AU2005277432A patent/AU2005277432B2/en not_active Ceased
- 2005-08-17 SI SI200531283T patent/SI1789036T1/sl unknown
- 2005-08-17 RU RU2007105822/04A patent/RU2391339C2/ru not_active IP Right Cessation
- 2005-08-17 US US11/205,954 patent/US7179831B2/en not_active Expired - Lifetime
- 2005-08-17 KR KR1020077006294A patent/KR101197325B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2577430A1 (en) | 2006-03-02 |
| SI1789036T1 (sl) | 2011-09-30 |
| WO2006023562B1 (en) | 2006-06-22 |
| RU2391339C2 (ru) | 2010-06-10 |
| HK1107774A1 (en) | 2008-04-18 |
| DK1789036T3 (da) | 2011-06-27 |
| RU2007105822A (ru) | 2008-09-27 |
| CN101014338B (zh) | 2010-06-16 |
| BRPI0514470B1 (pt) | 2021-01-05 |
| JP5042833B2 (ja) | 2012-10-03 |
| KR20070045330A (ko) | 2007-05-02 |
| CN101014338A (zh) | 2007-08-08 |
| NZ553258A (en) | 2011-02-25 |
| EP1789036B1 (en) | 2011-05-11 |
| MX2007001940A (es) | 2007-07-24 |
| BRPI0514470A (pt) | 2008-06-10 |
| KR101197325B1 (ko) | 2012-11-05 |
| ATE508744T1 (de) | 2011-05-15 |
| WO2006023562A3 (en) | 2006-04-20 |
| WO2006023562A2 (en) | 2006-03-02 |
| EP1789036A2 (en) | 2007-05-30 |
| BRPI0514470B8 (pt) | 2021-07-20 |
| AU2005277432B2 (en) | 2011-11-24 |
| US7179831B2 (en) | 2007-02-20 |
| ES2364068T3 (es) | 2011-08-24 |
| JP2008510701A (ja) | 2008-04-10 |
| EP1789036A4 (en) | 2008-08-27 |
| US20060041000A1 (en) | 2006-02-23 |
| AU2005277432A1 (en) | 2006-03-02 |
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