IL126797A - Polyhydroxyphenol derivatives and preparations for the prevention and cure of bone and cartilage diseases containing them - Google Patents
Polyhydroxyphenol derivatives and preparations for the prevention and cure of bone and cartilage diseases containing themInfo
- Publication number
- IL126797A IL126797A IL12679797A IL12679797A IL126797A IL 126797 A IL126797 A IL 126797A IL 12679797 A IL12679797 A IL 12679797A IL 12679797 A IL12679797 A IL 12679797A IL 126797 A IL126797 A IL 126797A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- group
- methyl
- butenyl
- methylpropyl
- Prior art date
Links
- 210000000988 bone and bone Anatomy 0.000 title claims description 15
- 239000003814 drug Substances 0.000 title description 19
- 230000003449 preventive effect Effects 0.000 title description 9
- 150000008442 polyphenolic compounds Polymers 0.000 title description 8
- 229940124597 therapeutic agent Drugs 0.000 title description 6
- 208000020084 Bone disease Diseases 0.000 title description 4
- 208000015100 cartilage disease Diseases 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 150
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 64
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 44
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 39
- -1 2,6-dimethylheptyl Chemical group 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
- 125000002252 acyl group Chemical group 0.000 claims abstract description 32
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 32
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 31
- 150000003839 salts Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 12
- LRQXIVBTVXEEMC-UHFFFAOYSA-N 3-methyl-1-(2,4,5-trihydroxyphenyl)butan-1-one Chemical compound CC(C)CC(=O)C1=CC(O)=C(O)C=C1O LRQXIVBTVXEEMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract 30
- 150000002367 halogens Chemical class 0.000 claims abstract 30
- 150000002431 hydrogen Chemical class 0.000 claims abstract 15
- 231100000252 nontoxic Toxicity 0.000 claims abstract 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract 6
- UATRONWBYDQKSQ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOCC=C(C)C UATRONWBYDQKSQ-UHFFFAOYSA-N 0.000 claims abstract 3
- HUSXULLBJMMRPI-UHFFFAOYSA-N 3-methyl-1-[3,4,6-trihydroxy-2-(3-methylbut-2-enyl)phenyl]butan-1-one Chemical compound CC(C)CC(=O)C1=C(O)C=C(O)C(O)=C1CC=C(C)C HUSXULLBJMMRPI-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 47
- 201000010099 disease Diseases 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 13
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 210000000845 cartilage Anatomy 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- IDIBYHHYXHPRKZ-UHFFFAOYSA-N 1-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC(CC=C(C)C)=C(O)C=C1O IDIBYHHYXHPRKZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- YXEDTECPOHHPAD-UHFFFAOYSA-N 1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC=C(O)C(CC=C(C)C)=C1O YXEDTECPOHHPAD-UHFFFAOYSA-N 0.000 claims description 5
- ATOBPKQMTXQTOU-UHFFFAOYSA-N 1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC=C(OCC=C(C)C)C=C1O ATOBPKQMTXQTOU-UHFFFAOYSA-N 0.000 claims description 5
- PXMHIPNVPIORDS-UHFFFAOYSA-N 3-methyl-1-[2,4,5-trihydroxy-3-(3-methylbut-2-enyl)phenyl]butan-1-one Chemical compound CC(C)CC(=O)C1=CC(O)=C(O)C(CC=C(C)C)=C1O PXMHIPNVPIORDS-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- WAGDJWCCUWPLLZ-UHFFFAOYSA-N 1-[2-hydroxy-6-methyl-4-(3-methylbut-2-enoxy)phenyl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)c1c(C)cc(OCC=C(C)C)cc1O WAGDJWCCUWPLLZ-UHFFFAOYSA-N 0.000 claims description 4
- SRLGQXRHPDECMP-UHFFFAOYSA-N 3-methyl-1-[2,4,5-trihydroxy-3,6-bis(3-methylbut-2-enyl)phenyl]butan-1-one Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)=C1CC=C(C)C SRLGQXRHPDECMP-UHFFFAOYSA-N 0.000 claims description 4
- HYOUICCCHADEJP-UHFFFAOYSA-N O=C1C(C(=O)CC(C)C)=C(O)C=C(O)C1(CC=1C=CC=CC=1)CC1=CC=CC=C1 Chemical compound O=C1C(C(=O)CC(C)C)=C(O)C=C(O)C1(CC=1C=CC=CC=1)CC1=CC=CC=C1 HYOUICCCHADEJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- HNRXTJHMZRFTBX-UHFFFAOYSA-N 2-phenyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]ethanone Chemical compound CC(C)=CCC1=C(O)C=C(O)C(C(=O)CC=2C=CC=CC=2)=C1O HNRXTJHMZRFTBX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- RYGCTMHFTQFZGR-UHFFFAOYSA-N 1-(3,5-dibenzyl-2,4,6-trihydroxyphenyl)-3-methylbutan-1-one Chemical compound OC=1C(CC=2C=CC=CC=2)=C(O)C(C(=O)CC(C)C)=C(O)C=1CC1=CC=CC=C1 RYGCTMHFTQFZGR-UHFFFAOYSA-N 0.000 claims description 2
- OCEBAURMPQABPX-UHFFFAOYSA-N 4,6,6-tris(3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxy-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)CCC=C(C)C)=C(O)C(CC=C(C)CCC=C(C)C)(CC=C(C)CCC=C(C)C)C1=O OCEBAURMPQABPX-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 221
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- 239000000126 substance Substances 0.000 description 53
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- 239000012043 crude product Substances 0.000 description 36
- 239000000499 gel Substances 0.000 description 35
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- 238000003786 synthesis reaction Methods 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
- 229910052938 sodium sulfate Inorganic materials 0.000 description 31
- 235000011152 sodium sulphate Nutrition 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 30
- 238000010898 silica gel chromatography Methods 0.000 description 29
- 101150041968 CDC13 gene Proteins 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 239000012298 atmosphere Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- 239000011369 resultant mixture Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 208000003076 Osteolysis Diseases 0.000 description 15
- 208000029791 lytic metastatic bone lesion Diseases 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- VSDWHZGJGWMIRN-UHFFFAOYSA-N 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one Chemical compound CC(C)CC(=O)C1=C(O)C=C(O)C=C1O VSDWHZGJGWMIRN-UHFFFAOYSA-N 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 12
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- 235000019270 ammonium chloride Nutrition 0.000 description 11
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- BNEBXEZRBLYBCZ-UHFFFAOYSA-N 2-isobutyrylphloroglucinol Chemical compound CC(C)C(=O)C1=C(O)C=C(O)C=C1O BNEBXEZRBLYBCZ-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 9
- RDJUHLUBPADHNP-UHFFFAOYSA-N 1,2,3,5-tetrahydroxybenzene Chemical compound OC1=CC(O)=C(O)C(O)=C1 RDJUHLUBPADHNP-UHFFFAOYSA-N 0.000 description 8
- NGAJEWUVPCMBSA-UHFFFAOYSA-N 1-(2,4-dihydroxy-6-methylphenyl)-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=C(C)C=C(O)C=C1O NGAJEWUVPCMBSA-UHFFFAOYSA-N 0.000 description 8
- FRROKYIFKYUHFE-UHFFFAOYSA-N 3,7-dimethyl-1-(2,4,6-trihydroxyphenyl)octan-1-one Chemical compound CC(C)CCCC(C)CC(=O)C1=C(O)C=C(O)C=C1O FRROKYIFKYUHFE-UHFFFAOYSA-N 0.000 description 8
- XHTSHDHABXVSJI-UHFFFAOYSA-N 3-methyl-1-(2,3,4,6-tetrahydroxyphenyl)butan-1-one Chemical compound CC(C)CC(=O)C1=C(O)C=C(O)C(O)=C1O XHTSHDHABXVSJI-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- IKXBLHQHQIXDIB-UHFFFAOYSA-N 1-[2,4-dihydroxy-6-methyl-3-(3-methylbut-2-enyl)phenyl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=C(C)C=C(O)C(CC=C(C)C)=C1O IKXBLHQHQIXDIB-UHFFFAOYSA-N 0.000 description 7
- SLHBRIIHMDJIBT-UHFFFAOYSA-N 2-phenyl-1-(2,4,6-trihydroxyphenyl)ethanone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)CC1=CC=CC=C1 SLHBRIIHMDJIBT-UHFFFAOYSA-N 0.000 description 7
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000001256 steam distillation Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- AFLATBREDGLLKS-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC=C(O)C=C1O AFLATBREDGLLKS-UHFFFAOYSA-N 0.000 description 6
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 230000017074 necrotic cell death Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- IOBXAMCSYCVNET-UHFFFAOYSA-N 2-isobutyryl-4-prenylphloroglucinol Chemical compound CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O IOBXAMCSYCVNET-UHFFFAOYSA-N 0.000 description 5
- AKWUIGDOLMPLQJ-UHFFFAOYSA-N 2-methyl-1-(1,3,5,6-tetrahydroxycyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CC(C)C(=O)C1(O)C=C(O)C=C(O)C1O AKWUIGDOLMPLQJ-UHFFFAOYSA-N 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000000010 osteolytic effect Effects 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- PKVJUAUOOYCYCR-UHFFFAOYSA-N phenyl-(2,3,4,6-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(O)=C1C(=O)C1=CC=CC=C1 PKVJUAUOOYCYCR-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- LWLGKGHHVBVDKB-UHFFFAOYSA-N 2-(3-methylbutanoyl)-4-prenylphloroglucinol Chemical compound CC(C)CC(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O LWLGKGHHVBVDKB-UHFFFAOYSA-N 0.000 description 4
- NVRJFALLXBMMNQ-UHFFFAOYSA-N 3,7-dimethyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]octan-1-one Chemical compound CC(C)CCCC(C)CC(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O NVRJFALLXBMMNQ-UHFFFAOYSA-N 0.000 description 4
- LHAUSZZKLLDYSC-UHFFFAOYSA-N CC(C)CC(=O)C1=C(O)C=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O Chemical compound CC(C)CC(=O)C1=C(O)C=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LHAUSZZKLLDYSC-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 210000002449 bone cell Anatomy 0.000 description 4
- NQYBQBZOHCACCR-UHFFFAOYSA-N deoxyhumulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O NQYBQBZOHCACCR-UHFFFAOYSA-N 0.000 description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- UNTZSCLRAYBSEJ-UHFFFAOYSA-N 1-(2,3,4,6-tetrahydroxyphenyl)ethanone Chemical compound CC(=O)C1=C(O)C=C(O)C(O)=C1O UNTZSCLRAYBSEJ-UHFFFAOYSA-N 0.000 description 3
- UMDLEKOAFAMNOU-UHFFFAOYSA-N 1-[3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl]-2-phenylethanone Chemical compound CC(C)=CCCC(C)=CCC1=C(O)C=C(O)C(C(=O)CC=2C=CC=CC=2)=C1O UMDLEKOAFAMNOU-UHFFFAOYSA-N 0.000 description 3
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 3
- YNVWZQXJKIWVGN-UHFFFAOYSA-N 3,5,6-trihydroxy-4,6-dimethyl-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one Chemical compound CC(C)CC(=O)C1=C(O)C(C)=C(O)C(C)(O)C1=O YNVWZQXJKIWVGN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DRSITEVYZGOOQG-UHFFFAOYSA-N Cohumulone Chemical compound CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O DRSITEVYZGOOQG-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- 235000008694 Humulus lupulus Nutrition 0.000 description 3
- 208000037147 Hypercalcaemia Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 208000010191 Osteitis Deformans Diseases 0.000 description 3
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8154710A JPH09301916A (ja) | 1996-05-14 | 1996-05-14 | ポリヒドロキシフェノール誘導体およびそれらからなる骨・軟骨疾患予防・治療剤 |
| PCT/JP1997/001625 WO1997043235A1 (fr) | 1996-05-14 | 1997-05-14 | Derives polyhydroxyphenols et agents les contenant, destines a la prevention et a la therapie de maladies de l'os et du cartilage |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL126797A0 IL126797A0 (en) | 1999-08-17 |
| IL126797A true IL126797A (en) | 2004-06-20 |
Family
ID=15590273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12679797A IL126797A (en) | 1996-05-14 | 1997-05-14 | Polyhydroxyphenol derivatives and preparations for the prevention and cure of bone and cartilage diseases containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6177474B1 (de) |
| EP (1) | EP0994093B1 (de) |
| JP (1) | JPH09301916A (de) |
| CN (1) | CN1178889C (de) |
| AT (1) | ATE314339T1 (de) |
| AU (1) | AU737890B2 (de) |
| BR (1) | BR9709074A (de) |
| CA (1) | CA2255589A1 (de) |
| CZ (1) | CZ355498A3 (de) |
| DE (1) | DE69735008D1 (de) |
| EA (1) | EA001172B1 (de) |
| HU (1) | HUP9904402A3 (de) |
| IL (1) | IL126797A (de) |
| NO (1) | NO312892B1 (de) |
| NZ (1) | NZ332722A (de) |
| PL (1) | PL188398B1 (de) |
| SK (1) | SK283956B6 (de) |
| TR (1) | TR199802290T2 (de) |
| UA (1) | UA66759C2 (de) |
| WO (1) | WO1997043235A1 (de) |
| YU (1) | YU51398A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3942759B2 (ja) | 1999-01-25 | 2007-07-11 | 興和株式会社 | 電子透かしの埋め込み方法，復号方法およびその装置 |
| EP2364083A4 (de) * | 2008-12-10 | 2012-10-31 | Metaproteomics Llc | Verfahren zur aufreinigung von substituierten cyclopent-2-en-1-on-congeneren und substituierten 1,3-cyclopentadion-congeneren aus einer komplexen mischung mit gegenläufiger abscheidung |
| WO2023278394A1 (en) * | 2021-06-28 | 2023-01-05 | Firmenich Incorporated | Polycationic salts of phenolic compounds and uses thereof |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU168744B (de) * | 1971-12-02 | 1976-07-28 | ||
| JPS5515443A (en) * | 1978-07-19 | 1980-02-02 | Kirin Brewery Co Ltd | Antibacterial agent |
| JPS5581814A (en) * | 1978-12-15 | 1980-06-20 | Kirin Brewery Co Ltd | Antifungal agent |
| JPS56140943A (en) * | 1980-04-07 | 1981-11-04 | Takeda Chem Ind Ltd | Preparation of organic compound |
| JPS59175448A (ja) * | 1983-03-25 | 1984-10-04 | Sanko Kaihatsu Kagaku Kenkyusho:Kk | フエノ−ル系化合物 |
| JPS60155111A (ja) | 1983-10-20 | 1985-08-15 | Hisamitsu Pharmaceut Co Inc | 安定なケトプロフェン含有外用経皮製剤 |
| JPS6176433A (ja) * | 1984-09-21 | 1986-04-18 | Toyobo Co Ltd | 新規なカルコン誘導体 |
| JPS61176548A (ja) * | 1985-01-31 | 1986-08-08 | Nippon Zeon Co Ltd | アルキル（ジヒドロキシフエニル）ケトンの製造法 |
| JPS61180738A (ja) * | 1985-02-06 | 1986-08-13 | Nippon Zeon Co Ltd | アルキル（ジヒドロキシフエニル）ケトンの製造法 |
| JPS61293945A (ja) * | 1985-06-05 | 1986-12-24 | Sumitomo Chem Co Ltd | ポリヒドロキシベンゾフェノンの製造方法 |
| JPH0629182B2 (ja) * | 1986-12-20 | 1994-04-20 | キツセイ薬品工業株式会社 | 骨粗鬆症治療剤 |
| JPH0629185B2 (ja) * | 1986-12-22 | 1994-04-20 | キツセイ薬品工業株式会社 | 骨粗鬆症治療剤 |
| JPH0629184B2 (ja) * | 1986-12-22 | 1994-04-20 | キツセイ薬品工業株式会社 | 骨粗鬆症治療剤 |
| JPS63264543A (ja) * | 1987-04-17 | 1988-11-01 | Toyo Gosei Kogyo Kk | ポリヒドロキシベンゾフエノン類の製造方法 |
| JPH01242540A (ja) * | 1988-03-22 | 1989-09-27 | Tsumura & Co | 新規カルコン誘導体および該誘導体を有効成分とする抗潰瘍剤 |
| DE3936592A1 (de) * | 1989-11-03 | 1991-05-08 | Basf Ag | Verfahren zur herstellung und reinigung von 2-hydroxy-4-(2'-hydroxy-ethoxy)phenylarylketonen |
| JP2627349B2 (ja) * | 1989-11-13 | 1997-07-02 | 株式会社大塚製薬工場 | ３―アルキルフラボン誘導体及び５―リポキシゲナーゼ阻害剤 |
| ES2125267T3 (es) | 1991-07-15 | 1999-03-01 | Steiner Inc S S | Agentes estabilizantes de espuma y que proporcionan amargor derivados del lupulo. |
| JPH0625081A (ja) * | 1992-02-27 | 1994-02-01 | Asahi Breweries Ltd | 抗酸化作用を有するβ酸（ルプロン類）アシル誘導体 |
| JPH06312924A (ja) | 1993-04-28 | 1994-11-08 | Asahi Breweries Ltd | 抗酸化作用を有するフムロン類の利用 |
| JP3814309B2 (ja) * | 1994-04-12 | 2006-08-30 | リポプロテイン・テクノロジーズ・インコーポレイテッド | 骨粗鬆症治療剤 |
| JPH0827057A (ja) * | 1994-07-19 | 1996-01-30 | Asahi Breweries Ltd | 抗酸化作用を有する新規物質およびその製造方法 |
| JP3525267B2 (ja) * | 1994-07-19 | 2004-05-10 | アサヒビール株式会社 | 抗酸化作用を有するマロフェノンの利用およびその製造方法 |
| FR2729387B1 (fr) * | 1995-01-13 | 1997-03-21 | Great Lakes Chemical France | Procede pour la fabrication d'hydroxy-alcoxy-benzophenones |
| JPH08277241A (ja) * | 1995-04-04 | 1996-10-22 | Nippon Kayaku Co Ltd | ヒドロキシフェニルベンジルケトン類の製造方法と結晶変態 |
-
1996
- 1996-05-14 JP JP8154710A patent/JPH09301916A/ja active Pending
-
1997
- 1997-05-14 TR TR1998/02290T patent/TR199802290T2/xx unknown
- 1997-05-14 NZ NZ332722A patent/NZ332722A/en unknown
- 1997-05-14 PL PL97329885A patent/PL188398B1/pl not_active IP Right Cessation
- 1997-05-14 CZ CZ983554A patent/CZ355498A3/cs unknown
- 1997-05-14 AT AT97922050T patent/ATE314339T1/de not_active IP Right Cessation
- 1997-05-14 DE DE69735008T patent/DE69735008D1/de not_active Expired - Lifetime
- 1997-05-14 WO PCT/JP1997/001625 patent/WO1997043235A1/ja not_active Application Discontinuation
- 1997-05-14 US US09/180,756 patent/US6177474B1/en not_active Expired - Fee Related
- 1997-05-14 BR BR9709074A patent/BR9709074A/pt not_active Application Discontinuation
- 1997-05-14 AU AU27887/97A patent/AU737890B2/en not_active Ceased
- 1997-05-14 IL IL12679797A patent/IL126797A/en not_active IP Right Cessation
- 1997-05-14 CN CNB971963665A patent/CN1178889C/zh not_active Expired - Fee Related
- 1997-05-14 YU YU51398A patent/YU51398A/sh unknown
- 1997-05-14 UA UA98126539A patent/UA66759C2/xx unknown
- 1997-05-14 SK SK1531-98A patent/SK283956B6/sk unknown
- 1997-05-14 EP EP97922050A patent/EP0994093B1/de not_active Expired - Lifetime
- 1997-05-14 EA EA199801012A patent/EA001172B1/ru not_active IP Right Cessation
- 1997-05-14 HU HU9904402A patent/HUP9904402A3/hu unknown
- 1997-05-14 CA CA002255589A patent/CA2255589A1/en not_active Abandoned
-
1998
- 1998-11-13 NO NO19985298A patent/NO312892B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR9709074A (pt) | 1999-08-03 |
| PL329885A1 (en) | 1999-04-12 |
| UA66759C2 (en) | 2004-06-15 |
| AU737890B2 (en) | 2001-09-06 |
| EA001172B1 (ru) | 2000-10-30 |
| DE69735008D1 (de) | 2006-02-02 |
| JPH09301916A (ja) | 1997-11-25 |
| CA2255589A1 (en) | 1997-11-20 |
| US6177474B1 (en) | 2001-01-23 |
| AU2788797A (en) | 1997-12-05 |
| EA199801012A1 (ru) | 1999-06-24 |
| NO985298L (no) | 1999-01-13 |
| EP0994093A1 (de) | 2000-04-19 |
| NO985298D0 (no) | 1998-11-13 |
| HUP9904402A2 (hu) | 2000-09-28 |
| WO1997043235A1 (fr) | 1997-11-20 |
| EP0994093B1 (de) | 2005-12-28 |
| PL188398B1 (pl) | 2005-01-31 |
| EP0994093A4 (de) | 2000-05-17 |
| IL126797A0 (en) | 1999-08-17 |
| TR199802290T2 (xx) | 2001-09-21 |
| CN1225082A (zh) | 1999-08-04 |
| NO312892B1 (no) | 2002-07-15 |
| SK283956B6 (sk) | 2004-06-08 |
| HUP9904402A3 (en) | 2002-07-29 |
| CN1178889C (zh) | 2004-12-08 |
| NZ332722A (en) | 2001-07-27 |
| YU51398A (sh) | 2000-03-21 |
| SK153198A3 (en) | 1999-06-11 |
| CZ355498A3 (cs) | 1999-04-14 |
| ATE314339T1 (de) | 2006-01-15 |
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| MM9K | Patent not in force due to non-payment of renewal fees |