CA2590845A1 - Novel hydantoin derivatives as metalloproteinase inhibitors - Google Patents
Novel hydantoin derivatives as metalloproteinase inhibitors Download PDFInfo
- Publication number
- CA2590845A1 CA2590845A1 CA002590845A CA2590845A CA2590845A1 CA 2590845 A1 CA2590845 A1 CA 2590845A1 CA 002590845 A CA002590845 A CA 002590845A CA 2590845 A CA2590845 A CA 2590845A CA 2590845 A1 CA2590845 A1 CA 2590845A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- methyl
- acceptable salt
- 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
Links
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 title description 4
- 150000001469 hydantoins Chemical class 0.000 title description 4
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 46
- 101000990902 Homo sapiens Matrix metalloproteinase-9 Proteins 0.000 claims description 23
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 102100027998 Macrophage metalloelastase Human genes 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 claims description 12
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000027771 Obstructive airways disease Diseases 0.000 claims description 4
- 239000001099 ammonium carbonate Substances 0.000 claims description 4
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- AOSSJKMXLBALBV-JOCHJYFZSA-N (5s)-5-[[6-(2-cyclobutylpyrimidin-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C3CCC3)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O AOSSJKMXLBALBV-JOCHJYFZSA-N 0.000 claims description 2
- LDPJXGRNICHPCB-HXUWFJFHSA-N (5s)-5-[[6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-2,7-naphthyridin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C3CC3)=NC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O LDPJXGRNICHPCB-HXUWFJFHSA-N 0.000 claims description 2
- OEQLCXYTKIRISP-OAQYLSRUSA-N (5s)-5-[[6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C3CC3)=CC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O OEQLCXYTKIRISP-OAQYLSRUSA-N 0.000 claims description 2
- BMXGUKRYJMVPCE-OAQYLSRUSA-N (5s)-5-[[6-(6-cyclopropylpyridin-3-yl)-3,4-dihydro-1h-2,7-naphthyridin-2-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=CC=3)C3CC3)=NC=C2CN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O BMXGUKRYJMVPCE-OAQYLSRUSA-N 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- KFSHRBYTUSBDGT-OAQYLSRUSA-N (5s)-5-[[6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-2,7-naphthyridin-2-yl]sulfonylmethyl]-5-ethylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C3CC3)=NC=C2CN1S(=O)(=O)C[C@@]1(CC)NC(=O)NC1=O KFSHRBYTUSBDGT-OAQYLSRUSA-N 0.000 claims 1
- GNPKJIOJLOETEO-JOCHJYFZSA-N (5s)-5-[[6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]-5-ethylimidazolidine-2,4-dione Chemical compound C1CC2=CC(C=3C=NC(=NC=3)C3CC3)=CC=C2CN1S(=O)(=O)C[C@@]1(CC)NC(=O)NC1=O GNPKJIOJLOETEO-JOCHJYFZSA-N 0.000 claims 1
- LPMNKIDUXUPDBL-QHCPKHFHSA-N (5s)-5-cyclopropyl-5-[[6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)[C@@]1(C1CC1)CS(=O)(=O)N1CC2=CC=C(C=3C=NC(=NC=3)C3CC3)C=C2CC1 LPMNKIDUXUPDBL-QHCPKHFHSA-N 0.000 claims 1
- BIUIDDFOHIEILW-JOCHJYFZSA-N (5s)-5-methyl-5-[[6-[2-(1-methylcyclopropyl)pyrimidin-5-yl]-3,4-dihydro-1h-isoquinolin-2-yl]sulfonylmethyl]imidazolidine-2,4-dione Chemical compound N=1C=C(C=2C=C3CCN(CC3=CC=2)S(=O)(=O)C[C@]2(C)C(NC(=O)N2)=O)C=NC=1C1(C)CC1 BIUIDDFOHIEILW-JOCHJYFZSA-N 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 229940124761 MMP inhibitor Drugs 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 27
- 101150041968 CDC13 gene Proteins 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 17
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 229940088598 enzyme Drugs 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- -1 1-fluoro-l-cyclopropyl Chemical group 0.000 description 13
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 10
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 9
- 102000005741 Metalloproteases Human genes 0.000 description 9
- 108010006035 Metalloproteases Proteins 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 9
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- 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 5
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- 229910021120 PdC12 Inorganic materials 0.000 description 5
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- OZTPQWRLHLQVBD-UHFFFAOYSA-N 1,2,3,4-tetrahydro-2,7-naphthyridine Chemical compound C1=NC=C2CNCCC2=C1 OZTPQWRLHLQVBD-UHFFFAOYSA-N 0.000 description 4
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- ABRLVIWEDFKEOU-UHFFFAOYSA-N 6-(2-cyclopropylpyrimidin-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CC1C1=NC=C(C=2C=C3CCNCC3=CC=2)C=N1 ABRLVIWEDFKEOU-UHFFFAOYSA-N 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0403085A SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Novel componds |
| SE0403085-4 | 2004-12-17 | ||
| PCT/SE2005/001917 WO2006065215A1 (en) | 2004-12-17 | 2005-12-14 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2590845A1 true CA2590845A1 (en) | 2006-06-22 |
Family
ID=34075235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002590845A Abandoned CA2590845A1 (en) | 2004-12-17 | 2005-12-14 | Novel hydantoin derivatives as metalloproteinase inhibitors |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US7655664B2 (enExample) |
| EP (1) | EP1831199B1 (enExample) |
| JP (1) | JP2008524210A (enExample) |
| KR (1) | KR20070090924A (enExample) |
| CN (1) | CN101119987A (enExample) |
| AR (1) | AR051795A1 (enExample) |
| AT (1) | ATE545642T1 (enExample) |
| AU (1) | AU2005317286B2 (enExample) |
| BR (1) | BRPI0517035A (enExample) |
| CA (1) | CA2590845A1 (enExample) |
| ES (1) | ES2380670T3 (enExample) |
| IL (1) | IL183599A (enExample) |
| MX (1) | MX2007007023A (enExample) |
| MY (1) | MY147770A (enExample) |
| NO (1) | NO20073572L (enExample) |
| NZ (1) | NZ555831A (enExample) |
| RU (1) | RU2376301C2 (enExample) |
| SA (1) | SA05260409B1 (enExample) |
| SE (1) | SE0403085D0 (enExample) |
| TW (1) | TW200635917A (enExample) |
| UA (1) | UA90285C2 (enExample) |
| WO (1) | WO2006065215A1 (enExample) |
| ZA (1) | ZA200705075B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0100902D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0401762D0 (sv) * | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| US7648992B2 (en) * | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| SE0403086D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| US7945626B2 (en) * | 2005-03-16 | 2011-05-17 | M&Fc Holding, Llc | Method, system, apparatus, and computer program product for determining a physical location of a sensor |
| MX2007013595A (es) * | 2005-05-04 | 2008-01-24 | Renovis Inc | Compuestos heterociclicos fusionados y composiciones y usos de estos. |
| TW200740769A (en) | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| KR101271219B1 (ko) * | 2011-01-27 | 2013-06-07 | 광주과학기술원 | 신규한 하이단토인 유도체 및 이의 용도 |
| JP6258508B2 (ja) * | 2013-12-31 | 2018-01-10 | イプセン ファルマ ソシエテ パール アクシオン サンプリフィエＩｐｓｅｎ Ｐｈａｒｍａ Ｓ．Ａ．Ｓ． | 新規のイミダゾリジン−２，４−ジオン誘導体 |
| US20200268728A1 (en) | 2016-12-20 | 2020-08-27 | Sumitomo Dainippon Pharma Co., Ltd. | Drug targeting cancer stem cell |
| PE20221836A1 (es) | 2020-03-26 | 2022-11-29 | Richter Gedeon Nyrt | Derivados de naftiridina y pirido[3,4-c]piridazina como moduladores del receptor gabaa 5 |
| EP4458810A4 (en) | 2021-12-28 | 2025-12-17 | Nippon Shinyaku Co Ltd | INDAZOLE COMPOUND AND PHARMACEUTICAL PRODUCT |
| CA3258111A1 (en) * | 2022-05-30 | 2025-04-07 | Scinnohub Pharmaceutical Co., Ltd | USE OF A TETRAHYDRONAPHTYRIDINE DERIVATIVE FOR THE PREPARATION OF A MEDICINAL PRODUCT FOR THE PREVENTION AND TREATMENT OF DISEASES RELATED TO ADHESION |
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| SE0202693D0 (sv) * | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| GB0221246D0 (en) * | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
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| US7648992B2 (en) * | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0401763D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Compounds |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| SE0403086D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| TW200740769A (en) * | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
-
2004
- 2004-12-17 SE SE0403085A patent/SE0403085D0/sv unknown
-
2005
- 2005-12-14 MX MX2007007023A patent/MX2007007023A/es active IP Right Grant
- 2005-12-14 WO PCT/SE2005/001917 patent/WO2006065215A1/en not_active Ceased
- 2005-12-14 AT AT05815745T patent/ATE545642T1/de active
- 2005-12-14 EP EP05815745A patent/EP1831199B1/en not_active Expired - Lifetime
- 2005-12-14 AU AU2005317286A patent/AU2005317286B2/en not_active Ceased
- 2005-12-14 ES ES05815745T patent/ES2380670T3/es not_active Expired - Lifetime
- 2005-12-14 JP JP2007546609A patent/JP2008524210A/ja active Pending
- 2005-12-14 RU RU2007126746/04A patent/RU2376301C2/ru not_active IP Right Cessation
- 2005-12-14 CN CNA2005800481778A patent/CN101119987A/zh active Pending
- 2005-12-14 NZ NZ555831A patent/NZ555831A/en not_active IP Right Cessation
- 2005-12-14 KR KR1020077013489A patent/KR20070090924A/ko not_active Ceased
- 2005-12-14 BR BRPI0517035-4A patent/BRPI0517035A/pt not_active IP Right Cessation
- 2005-12-14 US US11/721,586 patent/US7655664B2/en not_active Expired - Fee Related
- 2005-12-14 UA UAA200706657A patent/UA90285C2/ru unknown
- 2005-12-14 CA CA002590845A patent/CA2590845A1/en not_active Abandoned
- 2005-12-15 MY MYPI20055915A patent/MY147770A/en unknown
- 2005-12-15 AR ARP050105273A patent/AR051795A1/es not_active Application Discontinuation
- 2005-12-16 TW TW094144602A patent/TW200635917A/zh unknown
- 2005-12-17 SA SA05260409A patent/SA05260409B1/ar unknown
-
2007
- 2007-05-31 IL IL183599A patent/IL183599A/en not_active IP Right Cessation
- 2007-06-12 ZA ZA200705075A patent/ZA200705075B/xx unknown
- 2007-07-10 NO NO20073572A patent/NO20073572L/no not_active Application Discontinuation
-
2010
- 2010-02-01 US US12/697,625 patent/US20100256166A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005317286A1 (en) | 2006-06-22 |
| BRPI0517035A (pt) | 2008-09-30 |
| KR20070090924A (ko) | 2007-09-06 |
| ATE545642T1 (de) | 2012-03-15 |
| US20100256166A1 (en) | 2010-10-07 |
| ZA200705075B (en) | 2008-12-31 |
| IL183599A (en) | 2012-02-29 |
| CN101119987A (zh) | 2008-02-06 |
| SA05260409B1 (ar) | 2009-03-14 |
| UA90285C2 (ru) | 2010-04-26 |
| TW200635917A (en) | 2006-10-16 |
| WO2006065215A1 (en) | 2006-06-22 |
| RU2376301C2 (ru) | 2009-12-20 |
| MY147770A (en) | 2013-01-31 |
| AU2005317286B2 (en) | 2009-02-05 |
| ES2380670T3 (es) | 2012-05-17 |
| NZ555831A (en) | 2011-01-28 |
| RU2007126746A (ru) | 2009-01-27 |
| AR051795A1 (es) | 2007-02-07 |
| SE0403085D0 (sv) | 2004-12-17 |
| EP1831199B1 (en) | 2012-02-15 |
| EP1831199A1 (en) | 2007-09-12 |
| MX2007007023A (es) | 2007-09-11 |
| US20080293743A1 (en) | 2008-11-27 |
| JP2008524210A (ja) | 2008-07-10 |
| US7655664B2 (en) | 2010-02-02 |
| IL183599A0 (en) | 2007-09-20 |
| NO20073572L (no) | 2007-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131125 |