OA10611A - Indole derivatives useful in the treatment of osteoporosis - Google Patents
Indole derivatives useful in the treatment of osteoporosis Download PDFInfo
- Publication number
- OA10611A OA10611A OA70046A OA70046A OA10611A OA 10611 A OA10611 A OA 10611A OA 70046 A OA70046 A OA 70046A OA 70046 A OA70046 A OA 70046A OA 10611 A OA10611 A OA 10611A
- Authority
- OA
- OAPI
- Prior art keywords
- formula
- alkyl
- compound
- group
- optionally substituted
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 36
- 208000001132 Osteoporosis Diseases 0.000 title claims description 10
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 173
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 96
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000030507 AIDS Diseases 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 208000025865 Ulcer Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 231100000397 ulcer Toxicity 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 230000002491 angiogenic effect Effects 0.000 claims description 6
- 230000003143 atherosclerotic effect Effects 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 238000002054 transplantation Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000000260 hypercholesteremic effect Effects 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000003524 antilipemic agent Substances 0.000 claims description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 17
- 239000003814 drug Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000012453 solvate Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 210000000988 bone and bone Anatomy 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
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- 150000002431 hydrogen Chemical class 0.000 description 21
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- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 229960004132 diethyl ether Drugs 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 210000002997 osteoclast Anatomy 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
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- 239000012528 membrane Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- 239000000725 suspension Substances 0.000 description 7
- 108091006112 ATPases Proteins 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- 230000002829 reductive effect Effects 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- AIDS & HIV (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI950030A IT1272878B (it) | 1995-01-10 | 1995-01-10 | Composti indolici |
IT95MI001687 IT1307328B1 (it) | 1995-08-01 | 1995-08-01 | Composti indolici |
Publications (1)
Publication Number | Publication Date |
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OA10611A true OA10611A (en) | 2002-09-03 |
Family
ID=26331230
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
OA70046A OA10611A (en) | 1995-01-10 | 1997-07-09 | Indole derivatives useful in the treatment of osteoporosis |
Country Status (19)
Country | Link |
---|---|
US (1) | US5981525A (tr) |
EP (1) | EP0802902A1 (tr) |
JP (1) | JPH10512251A (tr) |
KR (1) | KR19980701330A (tr) |
AP (1) | AP648A (tr) |
AU (1) | AU4536096A (tr) |
BG (1) | BG101769A (tr) |
BR (1) | BR9606743A (tr) |
CA (1) | CA2209936A1 (tr) |
CZ (1) | CZ217697A3 (tr) |
EA (1) | EA199700098A1 (tr) |
FI (1) | FI972919A (tr) |
HU (1) | HUP9901096A3 (tr) |
NO (1) | NO973178L (tr) |
OA (1) | OA10611A (tr) |
PL (1) | PL321263A1 (tr) |
SK (1) | SK93297A3 (tr) |
TR (1) | TR199700625T1 (tr) |
WO (1) | WO1996021644A1 (tr) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5977125A (en) * | 1994-10-31 | 1999-11-02 | Eisai Co., Ltd. | Mono-or polyenic carboxylic acid derivatives |
GB9614347D0 (en) * | 1996-07-09 | 1996-09-04 | Smithkline Beecham Spa | Novel compounds |
GB9614366D0 (en) * | 1996-07-09 | 1996-09-04 | Smithkline Beecham Spa | Novel compounds |
DE69730837T2 (de) | 1996-07-09 | 2005-09-29 | Nikem Research S.R.L., Baranzate Di Bollate | Indolderivate zur behandlung von osteoporose |
GB9703109D0 (en) * | 1997-02-14 | 1997-04-02 | Smith & Nephew | Compositions |
CN1251577A (zh) * | 1997-02-21 | 2000-04-26 | 武田药品工业株式会社 | 稠环化合物及其生产和应用 |
WO1998039342A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
WO1998039344A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
WO1999033822A1 (en) * | 1997-12-24 | 1999-07-08 | Smithkline Beecham Laboratoires Pharmaceutiques | Indole derivatives useful a.o. for the treatment of osteoporosis |
US6506758B2 (en) | 1997-12-24 | 2003-01-14 | Smithkline Beecham Laboratoires Pharmceutiques | Indole derivatives useful A.O. for the treatment of osteoporosis |
US6861448B2 (en) * | 1998-01-14 | 2005-03-01 | Virtual Drug Development, Inc. | NAD synthetase inhibitors and uses thereof |
JP2002509149A (ja) | 1998-01-14 | 2002-03-26 | ザ ユーエイビー リサーチ ファウンデイション | 細菌nadシンテターゼ酵素の阻害剤の合成およびスクリーニング方法、その化合物、ならびに細菌nadシンテターゼ酵素の阻害剤を用いる細菌および微生物感染の治療方法 |
US6673827B1 (en) | 1999-06-29 | 2004-01-06 | The Uab Research Foundation | Methods of treating fungal infections with inhibitors of NAD synthetase enzyme |
GB9914371D0 (en) * | 1999-06-18 | 1999-08-18 | Smithkline Beecham Plc | Novel compounds |
SE9903760D0 (sv) * | 1999-10-18 | 1999-10-18 | Astra Ab | New compounds |
SE9904176D0 (sv) * | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
BR0208790A (pt) * | 2001-04-11 | 2004-03-30 | Idenix Cayman Ltd | Fenilindoìs para o tratamento de hiv |
AU2002339810A1 (en) * | 2001-10-16 | 2003-04-28 | Astrazeneca Ab | Azabicyclic compounds for the treatment of fibromyalgia syndrome |
JP2006500355A (ja) * | 2002-08-07 | 2006-01-05 | イデニクス(ケイマン)リミテツド | Hiv治療用の置換フェニルインドール類 |
ITMI20040875A1 (it) * | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | Derivati indolici utili per il trattamento della resistenza agli agenti antitumorali |
PT1799696E (pt) | 2004-09-17 | 2009-02-16 | Idenix Pharmaceuticals Inc | Fosfoindoles como inibidores de hiv |
US7812020B2 (en) * | 2005-03-03 | 2010-10-12 | H. Lundbeck A/S | Substituted pyridine derivatives |
CA2664396A1 (en) | 2006-09-29 | 2008-04-10 | Idenix Pharmaceuticals, Inc. | Enantiomerically pure phosphoindoles as hiv inhibitors |
LU91725B1 (en) | 2010-09-02 | 2012-03-05 | Ct De Rech Public De La Sante | Novel uses of V-ATPASE inhibitors |
US9115128B2 (en) * | 2013-06-06 | 2015-08-25 | Anthem Biosciences Pvt. Ltd. | Compounds of 3-(5-substituted Oxy-2, 4-dinitrophenyl)-2-oxo-propionic acid ester, synthesis and applications thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69102919T2 (de) * | 1990-03-20 | 1994-12-15 | Sharp Kk | Verfahren zur Montage von einer Halbleiteranordnung. |
CA2038925A1 (en) * | 1990-03-26 | 1991-09-27 | Takashi Sohda | Indole derivatives, their production and use |
US5312928A (en) * | 1991-02-11 | 1994-05-17 | Cambridge Neuroscience | Calcium channel antagonists and methodology for their identification |
-
1996
- 1996-01-08 CZ CZ972176A patent/CZ217697A3/cs unknown
- 1996-01-08 US US08/860,760 patent/US5981525A/en not_active Expired - Fee Related
- 1996-01-08 PL PL96321263A patent/PL321263A1/xx unknown
- 1996-01-08 AU AU45360/96A patent/AU4536096A/en not_active Abandoned
- 1996-01-08 TR TR97/00625T patent/TR199700625T1/tr unknown
- 1996-01-08 KR KR1019970704719A patent/KR19980701330A/ko not_active Application Discontinuation
- 1996-01-08 CA CA002209936A patent/CA2209936A1/en not_active Abandoned
- 1996-01-08 HU HU9901096A patent/HUP9901096A3/hu unknown
- 1996-01-08 EP EP96901275A patent/EP0802902A1/en not_active Withdrawn
- 1996-01-08 BR BR9606743A patent/BR9606743A/pt unknown
- 1996-01-08 WO PCT/EP1996/000157 patent/WO1996021644A1/en not_active Application Discontinuation
- 1996-01-08 AP APAP/P/1997/001029A patent/AP648A/en active
- 1996-01-08 JP JP8521450A patent/JPH10512251A/ja active Pending
- 1996-01-08 SK SK932-97A patent/SK93297A3/sk unknown
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1997
- 1997-07-07 BG BG101769A patent/BG101769A/xx unknown
- 1997-07-09 FI FI972919A patent/FI972919A/fi unknown
- 1997-07-09 OA OA70046A patent/OA10611A/en unknown
- 1997-07-09 NO NO973178A patent/NO973178L/no unknown
- 1997-08-08 EA EA199700098A patent/EA199700098A1/ru unknown
Also Published As
Publication number | Publication date |
---|---|
EA199700098A1 (ru) | 1997-12-30 |
FI972919A (fi) | 1997-09-09 |
JPH10512251A (ja) | 1998-11-24 |
NO973178D0 (no) | 1997-07-09 |
HUP9901096A3 (en) | 2000-12-28 |
KR19980701330A (ko) | 1998-05-15 |
HUP9901096A2 (hu) | 1999-07-28 |
MX9705243A (es) | 1997-10-31 |
WO1996021644A1 (en) | 1996-07-18 |
PL321263A1 (en) | 1997-11-24 |
FI972919A0 (fi) | 1997-07-09 |
BR9606743A (pt) | 1997-12-30 |
AU4536096A (en) | 1996-07-31 |
BG101769A (en) | 1998-04-30 |
TR199700625T1 (tr) | 1998-02-21 |
CA2209936A1 (en) | 1996-07-18 |
AP9701029A0 (en) | 1997-07-31 |
US5981525A (en) | 1999-11-09 |
SK93297A3 (en) | 1998-02-04 |
CZ217697A3 (cs) | 1998-03-18 |
EP0802902A1 (en) | 1997-10-29 |
AP648A (en) | 1998-05-25 |
NO973178L (no) | 1997-09-09 |
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