AU2003223233A1 - Bicyclic heterocycles for the treatment of diabetes and other diseases - Google Patents
Bicyclic heterocycles for the treatment of diabetes and other diseases Download PDFInfo
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- AU2003223233A1 AU2003223233A1 AU2003223233A AU2003223233A AU2003223233A1 AU 2003223233 A1 AU2003223233 A1 AU 2003223233A1 AU 2003223233 A AU2003223233 A AU 2003223233A AU 2003223233 A AU2003223233 A AU 2003223233A AU 2003223233 A1 AU2003223233 A1 AU 2003223233A1
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- Australia
- Prior art keywords
- substituted
- amino
- compound
- alkyl
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 238000011282 treatment Methods 0.000 title claims description 64
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 53
- 201000010099 disease Diseases 0.000 title description 39
- -1 nitro, hydroxyl Chemical group 0.000 claims description 407
- 150000001875 compounds Chemical class 0.000 claims description 364
- 125000004432 carbon atom Chemical group C* 0.000 claims description 184
- 125000000217 alkyl group Chemical group 0.000 claims description 133
- 125000001072 heteroaryl group Chemical group 0.000 claims description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims description 131
- 238000000034 method Methods 0.000 claims description 130
- 239000001257 hydrogen Substances 0.000 claims description 120
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 106
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 104
- 229910052736 halogen Inorganic materials 0.000 claims description 101
- 150000002367 halogens Chemical class 0.000 claims description 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 97
- 125000003118 aryl group Chemical group 0.000 claims description 90
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 83
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
- 125000002252 acyl group Chemical group 0.000 claims description 62
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 62
- 125000004423 acyloxy group Chemical group 0.000 claims description 57
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 57
- 125000004001 thioalkyl group Chemical group 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 54
- 230000037356 lipid metabolism Effects 0.000 claims description 50
- 125000001188 haloalkyl group Chemical group 0.000 claims description 49
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 47
- 230000023852 carbohydrate metabolic process Effects 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 46
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000002619 bicyclic group Chemical group 0.000 claims description 42
- 210000002966 serum Anatomy 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 40
- 235000021256 carbohydrate metabolism Nutrition 0.000 claims description 40
- 239000002243 precursor Substances 0.000 claims description 40
- 238000005859 coupling reaction Methods 0.000 claims description 39
- 241000124008 Mammalia Species 0.000 claims description 38
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 37
- 150000002632 lipids Chemical class 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 125000003107 substituted aryl group Chemical group 0.000 claims description 35
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 230000004069 differentiation Effects 0.000 claims description 31
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 30
- 241000282414 Homo sapiens Species 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 238000010168 coupling process Methods 0.000 claims description 27
- 230000007423 decrease Effects 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
- 230000008878 coupling Effects 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 150000001408 amides Chemical group 0.000 claims description 23
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 22
- 239000008103 glucose Substances 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 210000004027 cell Anatomy 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 17
- 210000000229 preadipocyte Anatomy 0.000 claims description 16
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 15
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 14
- 241000699670 Mus sp. Species 0.000 claims description 12
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical group O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- HOQLRIZVWNAXFA-UHFFFAOYSA-N 2-sulfanylidene-1,3-thiazolidin-4-one;1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1.O=C1CSC(=S)N1 HOQLRIZVWNAXFA-UHFFFAOYSA-N 0.000 claims description 5
- HPZMJNWGVDLITO-UHFFFAOYSA-N 5-[[3-[3,3-dimethyl-5-(2-methylpropyl)-2h-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(CC(C)C)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O HPZMJNWGVDLITO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- SPKRXUGNLPDKCR-UHFFFAOYSA-N imidazolidine-2,4-dione;2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=O)N1.O=C1CNC(=S)N1 SPKRXUGNLPDKCR-UHFFFAOYSA-N 0.000 claims description 5
- 230000006372 lipid accumulation Effects 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- ZCFXFIHRHWRKAY-UHFFFAOYSA-N 5-[[3-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O ZCFXFIHRHWRKAY-UHFFFAOYSA-N 0.000 claims description 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- GXJFKJQSRGQZGR-UHFFFAOYSA-N 2-[[7-[5-ethenyl-2-(trifluoromethoxy)phenyl]-3,3-dimethyl-2h-1-benzofuran-5-yl]methoxy]ethanol Chemical compound CC1(C)COC2=C1C=C(COCCO)C=C2C1=CC(C=C)=CC=C1OC(F)(F)F GXJFKJQSRGQZGR-UHFFFAOYSA-N 0.000 claims description 2
- BXZOTDCKVMQIBY-UHFFFAOYSA-N 5-[[3-(3,3-dimethyl-5-propanoyl-2h-1-benzofuran-7-yl)-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(=O)CC)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O BXZOTDCKVMQIBY-UHFFFAOYSA-N 0.000 claims description 2
- GRVMJAUSVNPYTJ-UHFFFAOYSA-N 5-[[3-[3,3-dimethyl-5-(2-methylpropanoyl)-2h-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(C(=O)C(C)C)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O GRVMJAUSVNPYTJ-UHFFFAOYSA-N 0.000 claims description 2
- RHAXOVIBEIBLCS-UHFFFAOYSA-N 5-[[3-[3,3-dimethyl-5-(2-methylpropyl)-2h-1-benzofuran-7-yl]-2,5-difluoro-4-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound FC1=C(C=2C3=C(C(CO3)(C)C)C=C(CC(C)C)C=2)C(OC)=C(F)C=C1C=C1SC(=O)NC1=O RHAXOVIBEIBLCS-UHFFFAOYSA-N 0.000 claims description 2
- NODFWJQQHRFEKI-UHFFFAOYSA-N 5-[[3-[5-[(dimethylamino)methyl]-3,3-dimethyl-2h-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(CN(C)C)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O NODFWJQQHRFEKI-UHFFFAOYSA-N 0.000 claims description 2
- LSTPKNZNEQFOFQ-UHFFFAOYSA-N 5-[[4-(dimethylamino)-3-[3,3-dimethyl-5-(2-methylpropyl)-2h-1-benzofuran-7-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(CC(C)C)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)N(C)C)=CC=1C=C1SC(=O)NC1=O LSTPKNZNEQFOFQ-UHFFFAOYSA-N 0.000 claims description 2
- UTAGEPVUNHXEAG-UHFFFAOYSA-N 7-[5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethoxy)phenyl]-n,3,3-trimethyl-2h-1-benzofuran-5-carboxamide Chemical compound C=1C(C(=O)NC)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O UTAGEPVUNHXEAG-UHFFFAOYSA-N 0.000 claims description 2
- BEMFENZSTXJOCT-UHFFFAOYSA-N 7-[5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethoxy)phenyl]-n,3,3-trimethyl-2h-1-benzofuran-5-sulfonamide Chemical compound C=1C(S(=O)(=O)NC)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O BEMFENZSTXJOCT-UHFFFAOYSA-N 0.000 claims description 2
- UCFNUNDTGDWNKC-UHFFFAOYSA-N methyl 7-[5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethoxy)phenyl]-3,3-dimethyl-2h-1-benzofuran-5-carboxylate Chemical compound C=1C(C(=O)OC)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O UCFNUNDTGDWNKC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- WYPANKNORPQJBO-UHFFFAOYSA-N 5-[[3-(3,3-dimethyl-5-methylsulfonyl-2h-1-benzofuran-7-yl)-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1(C)COC2=C1C=C(S(C)(=O)=O)C=C2C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O WYPANKNORPQJBO-UHFFFAOYSA-N 0.000 claims 1
- JDCHZNVEEADSFN-UHFFFAOYSA-N 5-[[3-[5-(furan-3-yl)-3,3-dimethyl-2h-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1(C)COC2=C1C=C(C1=COC=C1)C=C2C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O JDCHZNVEEADSFN-UHFFFAOYSA-N 0.000 claims 1
- BUCSWOOTHTYFNE-UHFFFAOYSA-N 5-[[3-[5-(methoxymethyl)-3,3-dimethyl-2h-1-benzofuran-7-yl]-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C(COC)=CC(C(CO2)(C)C)=C2C=1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O BUCSWOOTHTYFNE-UHFFFAOYSA-N 0.000 claims 1
- GZGJZTKREUNCGV-UHFFFAOYSA-N 7-[5-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethoxy)phenyl]-3,3-dimethyl-2h-1-benzofuran-5-carboxylic acid Chemical compound CC1(C)COC2=C1C=C(C(O)=O)C=C2C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O GZGJZTKREUNCGV-UHFFFAOYSA-N 0.000 claims 1
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- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 14
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- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- WHXAHMHWAOFQMS-UHFFFAOYSA-N n,3,3-trimethyl-2h-1-benzofuran-5-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C2OCC(C)(C)C2=C1 WHXAHMHWAOFQMS-UHFFFAOYSA-N 0.000 description 1
- RXNQXOGSLIJTGH-UHFFFAOYSA-N n,n,3,3-tetramethyl-2h-1-benzofuran-5-carboxamide Chemical compound CN(C)C(=O)C1=CC=C2OCC(C)(C)C2=C1 RXNQXOGSLIJTGH-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
- C07D417/10—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 carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36273202P | 2002-03-08 | 2002-03-08 | |
| US60/362,732 | 2002-03-08 | ||
| PCT/US2003/007240 WO2003075858A2 (en) | 2002-03-08 | 2003-03-07 | Bicyclic heterocycles for the treatment of diabetes and other diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003223233A2 AU2003223233A2 (en) | 2003-09-22 |
| AU2003223233A1 true AU2003223233A1 (en) | 2003-09-22 |
Family
ID=27805219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003223233A Abandoned AU2003223233A1 (en) | 2002-03-08 | 2003-03-07 | Bicyclic heterocycles for the treatment of diabetes and other diseases |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7196108B2 (https=) |
| EP (1) | EP1487446A4 (https=) |
| JP (1) | JP2005525371A (https=) |
| AU (1) | AU2003223233A1 (https=) |
| BR (1) | BR0308278A (https=) |
| CA (1) | CA2478765A1 (https=) |
| IL (1) | IL163953A0 (https=) |
| TW (1) | TWI277415B (https=) |
| WO (1) | WO2003075858A2 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ517993A (en) | 1999-08-31 | 2004-03-26 | Incyte San Diego Inc | Benzylidene-thiazolidinediones and analogues and their use in the treatment of diabetes |
| IL157740A0 (en) * | 2001-03-07 | 2004-03-28 | Incyte San Diego Inc | Heterocyclic derivatives and pharmaceutical compositions containing the same |
| US7265139B2 (en) * | 2001-03-08 | 2007-09-04 | Incyte San Diego Inc. | RXR activating molecules |
| WO2003016267A1 (en) * | 2001-08-17 | 2003-02-27 | Incyte San Diego Incorporated | Oxime derivatives for the treatment of dyslipidemia and hypercholesteremia |
| US7196108B2 (en) | 2002-03-08 | 2007-03-27 | Incyte San Diego Inc. | Bicyclic heterocycles for the treatment of diabetes and other diseases |
| US7102000B2 (en) * | 2002-03-08 | 2006-09-05 | Incyte San Diego Inc. | Heterocyclic amide derivatives for the treatment of diabetes and other diseases |
| ATE540047T1 (de) * | 2002-06-25 | 2012-01-15 | Helicon Therapeutics Inc | Gedächtnisveränderung durch beeinflussung der funktion von staufen |
| EP2133340B1 (en) | 2002-12-20 | 2013-01-16 | Glaxo Group Limited | Novel benzazepine derivatives |
| CN1774246A (zh) * | 2003-04-18 | 2006-05-17 | 因齐特圣迭戈公司 | 用于治疗代谢失调、癌症和其它疾病的取代异色满化合物 |
| US7122700B2 (en) | 2004-07-30 | 2006-10-17 | Xerox Corporation | Arylamine processes |
| GT200500185A (es) * | 2004-08-09 | 2006-04-10 | Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos | |
| CN101203505A (zh) * | 2005-04-22 | 2008-06-18 | 惠氏公司 | 苯并二氢吡喃和苯并吡喃衍生物及其用途 |
| US7638533B2 (en) * | 2005-09-30 | 2009-12-29 | Janssen Pharmaceutica N.V. | Dihydro-1[1H]-quinolin-2-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes |
| BRPI1010974A2 (pt) | 2009-05-22 | 2019-09-24 | Exelixis Inc | benzoxazepinas baseada em inibidores p13k/ m tor contra doenças proliferativas |
| CN102459248A (zh) | 2009-05-26 | 2012-05-16 | 埃克塞里艾克西斯公司 | 作为PI3K/mTOR抑制剂的苯并氧杂环庚三烯以及它们使用与制造方法 |
| US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| BR112012033402A2 (pt) | 2010-07-02 | 2017-01-24 | Gilead Sciences Inc | moduladores de canais de íons conforme os compostos heterocíclicos fundidos |
| WO2012031015A1 (en) * | 2010-09-01 | 2012-03-08 | The Regents Of The University Of California | Cell culture screen for agents that control adipogenesis and myofibroblast differentiation |
| CA2834164A1 (en) | 2011-05-10 | 2012-11-15 | Gilead Sciences, Inc. | Fused benzoxazinones as ion channel modulators |
| JP6014816B2 (ja) | 2011-05-10 | 2016-10-26 | 国立大学法人神戸大学 | Ras機能阻害作用を有するチオキソチアゾリジン誘導体 |
| TW201837023A (zh) | 2011-07-01 | 2018-10-16 | 美商基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| NO3175985T3 (https=) | 2011-07-01 | 2018-04-28 | ||
| WO2014082042A2 (en) | 2012-11-25 | 2014-05-30 | The Regents Of The University Of California | Peptides that stimulate subcutaneous adipogenesis |
| US10844102B2 (en) | 2014-05-28 | 2020-11-24 | The Regents Of The University Of California | Peptides, compositions, and methods for stimulating subcutaneous adipogenesis |
| CR20200553A (es) | 2018-04-18 | 2021-04-08 | Constellation Pharmaceuticals Inc | Moduladores de enzimas modificadoras de metilo, composiciones y usos de estos |
| CN120097995A (zh) | 2018-05-21 | 2025-06-06 | 星座制药公司 | 甲基修饰酶的调节剂、其组合物和用途 |
| WO2021016414A1 (en) | 2019-07-24 | 2021-01-28 | Constellation Pharmaceuticals, Inc. | Crystalline forms of 7-chloro-2-(4-(3-methoxyazetidin-1-yl)cyclohexyl)-2,4-dimethyl-n-((6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridin-3-yl)methyl)benzo[d][1,3]dioxole-5-carboxamide |
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| US4668506A (en) * | 1985-08-16 | 1987-05-26 | Bausch & Lomb Incorporated | Sustained-release formulation containing and amino acid polymer |
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| ATE173728T1 (de) * | 1991-07-22 | 1998-12-15 | Pfizer | Verfahren zur herstellung von (s)-4-(3-(5-methyl- 2-phenyl-4-oxazolyl)- 1-hydroxypropyl> brombenzol |
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| EP0915090A1 (en) * | 1992-09-10 | 1999-05-12 | Eli Lilly And Company | Compounds useful as hypoglycemic agents and for treating Alzheimer's disease |
| JPH08506323A (ja) | 1992-11-25 | 1996-07-09 | ラ ホヤ キャンサー リサーチ ファウンデーション | Rxrホモダイマー形成ならびに架橋二環式芳香族化合物および調節遺伝子発現におけるそれらの使用 |
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| JPH09136877A (ja) | 1995-06-16 | 1997-05-27 | Takeda Chem Ind Ltd | 複素環化合物、その製造法及び用途 |
| EP0850067A4 (en) | 1995-07-17 | 1999-12-15 | Cird Galderma | METHODS OF TREATING CANCER USING 6- 3- 1-ADAMANTYL] -4-HYDROXYPHENYL] |
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| IL127946A0 (en) * | 1996-07-08 | 2000-02-17 | Cird Galderma | Apoptosis inducing adamantyl derivatives and their usage as anti-cancer agents |
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| JP4398585B2 (ja) | 1997-11-12 | 2010-01-13 | 有限会社ケムフィズ | レチノイドレセプター作用剤 |
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| KR100608416B1 (ko) | 1999-11-12 | 2006-08-02 | 후지모토 쿄다이 가부시키가이샤 | 2-(n-시아노이미노)티아졸리딘-4-온 유도체 |
| FR2812876B1 (fr) * | 2000-08-08 | 2002-09-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| IL157740A0 (en) * | 2001-03-07 | 2004-03-28 | Incyte San Diego Inc | Heterocyclic derivatives and pharmaceutical compositions containing the same |
| US7265139B2 (en) * | 2001-03-08 | 2007-09-04 | Incyte San Diego Inc. | RXR activating molecules |
| EP1373240B1 (en) | 2001-03-14 | 2005-06-15 | Eli Lilly And Company | Retinoid x receptor modulators |
| JP4590158B2 (ja) | 2001-04-04 | 2010-12-01 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | グルコース再吸収阻害剤およびレチノイド−x受容体モジュレーターを含んで成る併用療法 |
| WO2003016267A1 (en) * | 2001-08-17 | 2003-02-27 | Incyte San Diego Incorporated | Oxime derivatives for the treatment of dyslipidemia and hypercholesteremia |
| AU2002352706A1 (en) * | 2001-11-15 | 2003-06-10 | Maxia Pharmaceuticals, Inc. | N-substituted heterocycles for the treatment of hypercholesteremia, dyslipidemia and other metabolic disorders, cancer, and other diseases |
| TW200304375A (en) * | 2001-12-06 | 2003-10-01 | Maxia Pharmaceuticals Inc | 2-Substituted thiazolidinone and oxazolidinone derivatives for the inhibition of phosphatases and the treatment of cancer |
| US7196108B2 (en) | 2002-03-08 | 2007-03-27 | Incyte San Diego Inc. | Bicyclic heterocycles for the treatment of diabetes and other diseases |
| US7102000B2 (en) * | 2002-03-08 | 2006-09-05 | Incyte San Diego Inc. | Heterocyclic amide derivatives for the treatment of diabetes and other diseases |
| US20050014767A1 (en) * | 2003-01-29 | 2005-01-20 | Magnus Pfahl | Benzoxazole, benzothiazole, and benzimidazole derivatives for the treatment of cancer and other diseases |
| CN1774246A (zh) * | 2003-04-18 | 2006-05-17 | 因齐特圣迭戈公司 | 用于治疗代谢失调、癌症和其它疾病的取代异色满化合物 |
-
2003
- 2003-03-06 US US10/384,391 patent/US7196108B2/en not_active Expired - Fee Related
- 2003-03-07 CA CA002478765A patent/CA2478765A1/en not_active Abandoned
- 2003-03-07 BR BR0308278-4A patent/BR0308278A/pt not_active IP Right Cessation
- 2003-03-07 IL IL16395303A patent/IL163953A0/xx unknown
- 2003-03-07 EP EP03719363A patent/EP1487446A4/en not_active Withdrawn
- 2003-03-07 AU AU2003223233A patent/AU2003223233A1/en not_active Abandoned
- 2003-03-07 TW TW092105026A patent/TWI277415B/zh not_active IP Right Cessation
- 2003-03-07 WO PCT/US2003/007240 patent/WO2003075858A2/en not_active Ceased
- 2003-03-07 JP JP2003574134A patent/JP2005525371A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7196108B2 (en) | 2007-03-27 |
| TW200304814A (en) | 2003-10-16 |
| WO2003075858A3 (en) | 2004-03-18 |
| TWI277415B (en) | 2007-04-01 |
| US20040034004A1 (en) | 2004-02-19 |
| BR0308278A (pt) | 2005-02-09 |
| CA2478765A1 (en) | 2003-09-18 |
| AU2003223233A2 (en) | 2003-09-22 |
| EP1487446A4 (en) | 2006-04-19 |
| IL163953A0 (en) | 2005-12-18 |
| WO2003075858A2 (en) | 2003-09-18 |
| EP1487446A2 (en) | 2004-12-22 |
| JP2005525371A (ja) | 2005-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 01 OCT 2004 |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |