NO314845B1 - Matriks-metalloprotease-inhibitorer, fremstilling og anvendelse av dem og farmasöytiske preparater som inneholder dem - Google Patents
Matriks-metalloprotease-inhibitorer, fremstilling og anvendelse av dem og farmasöytiske preparater som inneholder dem Download PDFInfo
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- NO314845B1 NO314845B1 NO19965413A NO965413A NO314845B1 NO 314845 B1 NO314845 B1 NO 314845B1 NO 19965413 A NO19965413 A NO 19965413A NO 965413 A NO965413 A NO 965413A NO 314845 B1 NO314845 B1 NO 314845B1
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- hydrogen
- phenyl
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- 239000003475 metalloproteinase inhibitor Substances 0.000 title claims abstract 4
- 238000002360 preparation method Methods 0.000 title claims description 223
- 239000008194 pharmaceutical composition Substances 0.000 title 1
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- -1 arylheteroalkyl Chemical group 0.000 claims abstract description 162
- 239000001257 hydrogen Substances 0.000 claims abstract description 160
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 160
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- 229910052799 carbon Inorganic materials 0.000 claims abstract description 97
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- FWTRIMNXFWUGNC-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenoxy)phenyl]sulfonyloxan-4-yl]-n-hydroxyacetamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)C1(CC(=O)NO)CCOCC1 FWTRIMNXFWUGNC-UHFFFAOYSA-N 0.000 claims description 3
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- QOPFTBAEAJQKSY-UHFFFAOYSA-N 2-{4-[4-(4-chloro-phenoxy)-benzenesulfonyl]-tetrahydro-pyran-4-yl}-n-hydroxy-acetamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1(CC(=O)NO)CCOCC1 QOPFTBAEAJQKSY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- ZMUPAVUEYVXZSL-UHFFFAOYSA-N n-hydroxy-2-[1-methyl-4-(4-phenoxyphenyl)sulfonylpiperidin-4-yl]acetamide Chemical compound C1CN(C)CCC1(CC(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 ZMUPAVUEYVXZSL-UHFFFAOYSA-N 0.000 claims description 2
- YXWCROYQBAZEBW-UHFFFAOYSA-N n-hydroxy-2-[4-(4-phenoxyphenyl)sulfonylpiperidin-4-yl]acetamide Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1S(=O)(=O)C1(CC(=O)NO)CCNCC1 YXWCROYQBAZEBW-UHFFFAOYSA-N 0.000 claims description 2
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- DCSATTBHEMKGIP-UHFFFAOYSA-N n-tert-butylhydroxylamine;hydron;chloride Chemical compound Cl.CC(C)(C)NO DCSATTBHEMKGIP-UHFFFAOYSA-N 0.000 description 1
- 210000002184 nasal cartilage Anatomy 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- ZBDXGNXNXXPKJI-UHFFFAOYSA-N o-tert-butylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)(C)ON ZBDXGNXNXXPKJI-UHFFFAOYSA-N 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
- AVFOWAMCPHWQDR-UHFFFAOYSA-M potassium;4-phenoxybenzenethiolate Chemical compound [K+].C1=CC([S-])=CC=C1OC1=CC=CC=C1 AVFOWAMCPHWQDR-UHFFFAOYSA-M 0.000 description 1
- OALPPYUMFWGHEK-UHFFFAOYSA-M potassium;benzenethiolate Chemical compound [K+].[S-]C1=CC=CC=C1 OALPPYUMFWGHEK-UHFFFAOYSA-M 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
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- 230000028327 secretion Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
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- UYZGFWDZVGELPB-UHFFFAOYSA-N tert-butyl 2-(4-methylcyclohexylidene)acetate Chemical compound CC1CCC(=CC(=O)OC(C)(C)C)CC1 UYZGFWDZVGELPB-UHFFFAOYSA-N 0.000 description 1
- OLTQCCDQAVEAIU-UHFFFAOYSA-N tert-butyl 2-(oxan-4-ylidene)acetate Chemical compound CC(C)(C)OC(=O)C=C1CCOCC1 OLTQCCDQAVEAIU-UHFFFAOYSA-N 0.000 description 1
- LVHOUHSAOSOKQK-UHFFFAOYSA-N tert-butyl 2-benzylprop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)CC1=CC=CC=C1 LVHOUHSAOSOKQK-UHFFFAOYSA-N 0.000 description 1
- UKAWTMNPWPAJIT-UHFFFAOYSA-N tert-butyl 2-cyclohexylideneacetate Chemical compound CC(C)(C)OC(=O)C=C1CCCCC1 UKAWTMNPWPAJIT-UHFFFAOYSA-N 0.000 description 1
- MKESCYGAZBTFDG-UHFFFAOYSA-N tert-butyl 2-cyclopentylideneacetate Chemical compound CC(C)(C)OC(=O)C=C1CCCC1 MKESCYGAZBTFDG-UHFFFAOYSA-N 0.000 description 1
- FJIZXSCSAUHRPP-UHFFFAOYSA-N tert-butyl 2-methylpent-2-enoate Chemical group CCC=C(C)C(=O)OC(C)(C)C FJIZXSCSAUHRPP-UHFFFAOYSA-N 0.000 description 1
- BTYQWISIPUWRJR-UHFFFAOYSA-N tert-butyl 3-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate Chemical compound COC(=O)CC1CCCN(C(=O)OC(C)(C)C)C1 BTYQWISIPUWRJR-UHFFFAOYSA-N 0.000 description 1
- KNXISWJTUXKGCI-UHFFFAOYSA-N tert-butyl 3-methylbut-2-enoate Chemical compound CC(C)=CC(=O)OC(C)(C)C KNXISWJTUXKGCI-UHFFFAOYSA-N 0.000 description 1
- YPJNGAPAWYYQLL-UHFFFAOYSA-N tert-butyl 3-oxo-2-oxa-7-azaspiro[3.5]nonane-7-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC11C(=O)OC1 YPJNGAPAWYYQLL-UHFFFAOYSA-N 0.000 description 1
- ZIKDESSLWKOLAH-UHFFFAOYSA-N tert-butyl 4-cyclopentylbut-2-enoate Chemical compound CC(C)(C)OC(=O)C=CCC1CCCC1 ZIKDESSLWKOLAH-UHFFFAOYSA-N 0.000 description 1
- KXRSVBFFQOQGED-UHFFFAOYSA-N tert-butyl 4-phenyl-2-propan-2-ylbut-2-enoate Chemical group CC(C)(C)OC(=O)C(C(C)C)=CCC1=CC=CC=C1 KXRSVBFFQOQGED-UHFFFAOYSA-N 0.000 description 1
- QDBFOWJVSNFYNK-UHFFFAOYSA-N tert-butyl 4-phenylbut-2-enoate Chemical group CC(C)(C)OC(=O)C=CCC1=CC=CC=C1 QDBFOWJVSNFYNK-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- BMCJATLPEJCACU-UHFFFAOYSA-N tricin Natural products COc1cc(OC)c(O)c(c1)C2=CC(=O)c3c(O)cc(O)cc3O2 BMCJATLPEJCACU-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical class Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 210000002993 trophoblast Anatomy 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004325 uterine smooth muscle cell Anatomy 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—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
- C07D309/08—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US893995P | 1995-12-20 | 1995-12-20 | |
US2243996P | 1996-08-07 | 1996-08-07 | |
US3209696P | 1996-12-04 | 1996-12-04 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO965413D0 NO965413D0 (no) | 1996-12-16 |
NO965413L NO965413L (no) | 1997-06-23 |
NO314845B1 true NO314845B1 (no) | 2003-06-02 |
Family
ID=27358753
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19965413A NO314845B1 (no) | 1995-12-20 | 1996-12-16 | Matriks-metalloprotease-inhibitorer, fremstilling og anvendelse av dem og farmasöytiske preparater som inneholder dem |
Country Status (30)
Country | Link |
---|---|
US (1) | US5932595A (zh) |
EP (1) | EP0780386B1 (zh) |
JP (1) | JP2921673B2 (zh) |
KR (1) | KR100240536B1 (zh) |
CN (1) | CN1177821C (zh) |
AT (1) | ATE225343T1 (zh) |
AU (1) | AU700725B2 (zh) |
BR (1) | BR9606134A (zh) |
CO (1) | CO4790091A1 (zh) |
CY (1) | CY2414B1 (zh) |
CZ (1) | CZ291478B6 (zh) |
DE (1) | DE69624081T2 (zh) |
DK (1) | DK0780386T3 (zh) |
ES (1) | ES2183905T3 (zh) |
HK (1) | HK1012343A1 (zh) |
HR (1) | HRP960612B1 (zh) |
HU (1) | HU225696B1 (zh) |
IL (1) | IL119843A (zh) |
MX (1) | MX9606709A (zh) |
MY (1) | MY117574A (zh) |
NO (1) | NO314845B1 (zh) |
NZ (1) | NZ299941A (zh) |
PE (1) | PE30298A1 (zh) |
PL (1) | PL198032B1 (zh) |
PT (1) | PT780386E (zh) |
RS (1) | RS49781B (zh) |
RU (1) | RU2175316C2 (zh) |
SG (1) | SG76490A1 (zh) |
TR (1) | TR199601032A2 (zh) |
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