ES2553340T3 - Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos - Google Patents
Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos Download PDFInfo
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- ES2553340T3 ES2553340T3 ES08860063.0T ES08860063T ES2553340T3 ES 2553340 T3 ES2553340 T3 ES 2553340T3 ES 08860063 T ES08860063 T ES 08860063T ES 2553340 T3 ES2553340 T3 ES 2553340T3
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- -1 amine compounds Chemical class 0.000 title description 67
- 208000030159 metabolic disease Diseases 0.000 title description 2
- 150000003857 carboxamides Chemical class 0.000 title 1
- 229940124530 sulfonamide Drugs 0.000 title 1
- 150000003456 sulfonamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 61
- 125000003118 aryl group Chemical group 0.000 abstract description 42
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 39
- 229910052799 carbon Inorganic materials 0.000 abstract description 31
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 27
- 125000004122 cyclic group Chemical group 0.000 abstract description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 11
- 150000001204 N-oxides Chemical class 0.000 abstract description 9
- 229910052736 halogen Inorganic materials 0.000 abstract description 9
- 150000003839 salts Chemical class 0.000 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 description 95
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 125000001188 haloalkyl group Chemical group 0.000 description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 125000005605 benzo group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 description 4
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004953 trihalomethyl group Chemical group 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229940126086 compound 21 Drugs 0.000 description 2
- 229940125936 compound 42 Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BCFVDNBHVMIRAB-UHFFFAOYSA-N n-[1-(4-cyanophenyl)sulfonylpiperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=CC(=CC=3)C#N)=C2CC1 BCFVDNBHVMIRAB-UHFFFAOYSA-N 0.000 description 2
- HGOCLAJPOYMRLC-UHFFFAOYSA-N n-[1-(pyridine-3-carbonyl)piperidin-4-yl]-2-[[4-(trifluoromethyl)phenyl]methyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)C(=O)C=3C=NC=CC=3)=C2CC1 HGOCLAJPOYMRLC-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- FRZNJFWQVYAVCE-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)phenyl]urea Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C=CC(OCCN3CCOCC3)=CC=2)=CC(C(C)(C)C)=N1 FRZNJFWQVYAVCE-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BKBLCVYZVFFSLX-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[3-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)=C2CC1 BKBLCVYZVFFSLX-UHFFFAOYSA-N 0.000 description 1
- KOEFDTDROGKCAT-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]-n-[1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1CC(C2=CC(=CC=C2N2)C(=O)NC3CCN(CC3)S(=O)(=O)C=3C=CC(=CC=3)C(F)(F)F)=C2CC1 KOEFDTDROGKCAT-UHFFFAOYSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- TWXLDXUFIJOBOG-UHFFFAOYSA-N 2-phenylmethoxycarbonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxylic acid Chemical compound C1C=2C3=CC(C(=O)O)=CC=C3NC=2CCN1C(=O)OCC1=CC=CC=C1 TWXLDXUFIJOBOG-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- WHKZBVQIMVUGIH-UHFFFAOYSA-N 3-hydroxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=NC2=C1 WHKZBVQIMVUGIH-UHFFFAOYSA-N 0.000 description 1
- JJNRPVDJAVHGHY-UHFFFAOYSA-N 3-methoxyquinoline-2-carboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(OC)=CC2=C1 JJNRPVDJAVHGHY-UHFFFAOYSA-N 0.000 description 1
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
- OZDCZHDOIBUGAJ-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)C=C1 OZDCZHDOIBUGAJ-UHFFFAOYSA-N 0.000 description 1
- PEYNABVSERZDTP-UHFFFAOYSA-N 4-[(4-aminopiperidin-1-yl)methyl]benzonitrile;dihydrochloride Chemical compound Cl.Cl.C1CC(N)CCN1CC1=CC=C(C#N)C=C1 PEYNABVSERZDTP-UHFFFAOYSA-N 0.000 description 1
- DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
- PCNFLKVWBDNNOW-UHFFFAOYSA-N 4-hydrazinylbenzoic acid Chemical compound NNC1=CC=C(C(O)=O)C=C1 PCNFLKVWBDNNOW-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
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- RRHFMTCBMINYNI-UHFFFAOYSA-N tert-butyl 4-(2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole-8-carbonylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC(=O)C1=CC=C(NC2=C3CNCC2)C3=C1 RRHFMTCBMINYNI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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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- 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
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- 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
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78209 | 1998-05-13 | ||
| US1312407P | 2007-12-12 | 2007-12-12 | |
| US1311407P | 2007-12-12 | 2007-12-12 | |
| US13124 | 2007-12-12 | ||
| US13114 | 2007-12-12 | ||
| US1640507P | 2007-12-21 | 2007-12-21 | |
| US1640607P | 2007-12-21 | 2007-12-21 | |
| US1640207P | 2007-12-21 | 2007-12-21 | |
| US16402 | 2007-12-21 | ||
| US16405 | 2007-12-21 | ||
| US16406 | 2008-01-18 | ||
| US7820908P | 2008-07-03 | 2008-07-03 | |
| PCT/US2008/086673 WO2009076631A1 (en) | 2007-12-12 | 2008-12-12 | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
Publications (1)
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|---|---|
| ES2553340T3 true ES2553340T3 (es) | 2015-12-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| ES08860063.0T Active ES2553340T3 (es) | 2007-12-12 | 2008-12-12 | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US8129390B2 (enExample) |
| EP (1) | EP2231666B1 (enExample) |
| JP (1) | JP5650540B2 (enExample) |
| CA (1) | CA2707047C (enExample) |
| ES (1) | ES2553340T3 (enExample) |
| WO (1) | WO2009076631A1 (enExample) |
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| ES2627221T3 (es) | 2006-12-28 | 2017-07-27 | Rigel Pharmaceuticals, Inc. | Compuestos de heterocicloalquiloxibenzamida N-sustituidos y métodos de uso |
| CA2705947C (en) | 2007-11-16 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| US8017573B2 (en) * | 2007-11-30 | 2011-09-13 | Siemens Healthcare Diagnostics Inc. | Adiponectin receptor fragments and methods of use |
| ES2553340T3 (es) | 2007-12-12 | 2015-12-07 | Rigel Pharmaceuticals, Inc. | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
| CN112079769A (zh) | 2008-04-23 | 2020-12-15 | 里格尔药品股份有限公司 | 用于治疗代谢障碍的甲酰胺化合物 |
| WO2010088392A1 (en) | 2009-01-28 | 2010-08-05 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds and methods for using the same |
| CN102459249A (zh) | 2009-05-22 | 2012-05-16 | 埃克塞里艾克西斯公司 | 作为PI3K/mTOR抑制剂的苯并氧氮杂环庚三烯以及它们使用与制造方法 |
| GB0915892D0 (en) * | 2009-09-10 | 2009-10-14 | Smithkline Beecham Corp | Compounds |
| WO2011032320A1 (en) * | 2009-09-21 | 2011-03-24 | F. Hoffmann-La Roche Ag | Novel alkene oxindole derivatives |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011123681A1 (en) | 2010-03-31 | 2011-10-06 | Rigel Pharmaceuticals, Inc. | Methods for using carboxamide, sulfonamide and amine compounds |
| WO2011142359A1 (ja) * | 2010-05-10 | 2011-11-17 | 日産化学工業株式会社 | スピロ化合物及びアディポネクチン受容体活性化薬 |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| US8791136B2 (en) | 2010-07-29 | 2014-07-29 | Rigel Pharmaceuticals, Inc. | Substituted pyridine, pyridazine, pyrazine and pyrimidine compounds and methods for using the same |
| US9005909B2 (en) | 2011-01-06 | 2015-04-14 | Rigel Pharmaceuticals, Inc. | Whole blood assay for measuring AMPK activation |
| CA2830706A1 (en) * | 2011-03-07 | 2012-09-13 | Glaxosmithkline Llc | Quinolinone derivatives |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JP6043290B2 (ja) * | 2011-09-22 | 2016-12-14 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9409884B2 (en) | 2012-02-01 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | 5- or 6-substituted benzofuran-2-carboxamide compounds and methods for using them |
| JP6664632B2 (ja) * | 2013-09-30 | 2020-03-13 | 国立大学法人 東京大学 | アディポネクチン受容体活性化化合物 |
| US20210238162A1 (en) * | 2015-12-17 | 2021-08-05 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| RU2732075C1 (ru) * | 2019-07-24 | 2020-09-11 | Федеральное государственное бюджетное учреждение науки Институт аналитического приборостроения Российской академии наук | Способ предварительной сепарации потока заряженных частиц в источнике ионов с ионизацией при атмосферном давлении |
| CA3178994A1 (en) | 2020-05-19 | 2021-11-25 | Iyassu Sebhat | Ampk activators |
| AU2021297323A1 (en) | 2020-06-26 | 2023-02-16 | Kallyope, Inc. | AMPK activators |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5028A (en) * | 1847-03-20 | monohot | ||
| DE3382687D1 (de) * | 1982-09-30 | 1993-07-01 | Ciba Geigy Ag | Mit bis-(polyalkylpiperidinyl-amino)-1,3,5-triazinen stabilisierte polyolefine. |
| GB8820115D0 (en) | 1988-08-24 | 1988-09-28 | Ici Plc | Insecticidal compounds |
| US5216156A (en) * | 1992-05-05 | 1993-06-01 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives |
| US6137002A (en) | 1993-07-22 | 2000-10-24 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| EP0891362B1 (en) | 1996-03-28 | 2004-03-17 | Glaxo Group Limited | Pyrrolopyrrolone derivatives as inhibitors of neutrophil elastase |
| GB9715584D0 (en) | 1997-07-23 | 1997-10-01 | Eisai Co Ltd | Compounds |
| DE19738615A1 (de) | 1997-09-04 | 1999-03-11 | Clariant Gmbh | Neue Lichtschutzmittel auf Basis von sterisch gehinderten Aminen |
| US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| JP2002523448A (ja) | 1998-08-28 | 2002-07-30 | サイオス インコーポレイテッド | ｐ３８−αキナーゼのインヒビター |
| US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
| AU780823B2 (en) | 1999-10-08 | 2005-04-21 | Grunenthal Gmbh | Bicyclic imidazo-3-yl-amine derivatives which are substituted on the sixth ring |
| US6436965B1 (en) | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| US7273868B2 (en) | 2000-04-28 | 2007-09-25 | Tanabe Seiyaku Co., Ltd. | Pyrazine derivatives |
| US6579328B2 (en) * | 2000-05-01 | 2003-06-17 | Ciba Specialty Chemicals Corporation | Transition-metal-catalyzed process for the preparation of sterically hindered N-substituted aryloxyamines |
| AU2001273040A1 (en) | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| DE10050663A1 (de) | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| DE60126997T2 (de) | 2000-10-20 | 2007-10-25 | Eisai R&D Management Co., Ltd. | Stickstoff-enthaltende aromatische ringverbindungen zur behandlung von tumorerkrankungen |
| US6875765B2 (en) | 2001-05-10 | 2005-04-05 | Warner-Lambert Company | Arylsulfonamide ethers, and methods of use thereof |
| WO2002094796A2 (en) * | 2001-05-18 | 2002-11-28 | Axxima Pharmaceuticals Ag | Benzo[g]quinoxaline derivatives as effective compounds against infectious diseases |
| MXPA04000779A (es) | 2001-08-24 | 2004-04-20 | Pharmacia & Up John Company | 7-aza[2.2.1]bicicloheptanos sustituidos con arilo para el tratamiento de enfermedades. |
| WO2003022856A1 (en) | 2001-09-12 | 2003-03-20 | Pharmacia & Upjohn Company | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
| TW200407307A (en) * | 2001-11-26 | 2004-05-16 | Ciba Sc Holding Ag | Process for the synthesis of amine ethers from secondary amino oxides |
| JP2005523288A (ja) | 2002-02-19 | 2005-08-04 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 疾病治療用の縮合した二環式−ｎ−架橋−複素環式芳香族カルボキサミド |
| BR0307874A (pt) | 2002-02-20 | 2004-12-28 | Upjohn Co | Atividade de compostos azabicìclicos com receptor de acetilcolina nicotìnica alfa7 |
| US20040082627A1 (en) | 2002-06-21 | 2004-04-29 | Darrow James W. | Certain aromatic monocycles as kinase modulators |
| JP2006511554A (ja) | 2002-12-13 | 2006-04-06 | スミスクライン ビーチャム コーポレーション | Ｃｃｒ５アンタゴニストとしてのピペリジン誘導体 |
| US7208491B2 (en) | 2003-02-07 | 2007-04-24 | Hoffmann-La Roche Inc. | N-monoacylated o-phenylenediamines |
| GB2400101A (en) | 2003-03-28 | 2004-10-06 | Biofocus Discovery Ltd | Compounds capable of binding to the active site of protein kinases |
| GB0314054D0 (en) | 2003-06-17 | 2003-07-23 | Pfizer Ltd | Amide derivatives as selective serotonin re-uptake inhibitors |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| US8362017B2 (en) | 2003-08-29 | 2013-01-29 | Exelixis, Inc. | C-kit modulators and methods of use |
| EP1697307B1 (en) * | 2003-12-12 | 2014-03-12 | Eli Lilly & Company | Opioid receptor antagonists |
| US7544803B2 (en) | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| PE20060315A1 (es) | 2004-05-24 | 2006-05-15 | Irm Llc | Compuestos de tiazol como moduladores de ppar |
| PL1755593T3 (pl) | 2004-06-02 | 2008-06-30 | Hoffmann La Roche | Pochodne naftalenu przydatne jako ligandy 3-receptora histaminowego |
| WO2005123716A1 (en) | 2004-06-21 | 2005-12-29 | F. Hoffmann-La Roche Ag | Indole derivatives as histamine receptor antagonists |
| WO2006045416A1 (en) | 2004-10-19 | 2006-05-04 | F. Hoffmann-La Roche Ag | Quinoline derivatives |
| KR20070068432A (ko) | 2004-10-29 | 2007-06-29 | 아스트라제네카 아베 | 염증 질환의 치료를 위한 글루코코르티코이드 수용체조절제로서의 신규 술폰아미드 유도체 |
| JP4935357B2 (ja) | 2004-11-08 | 2012-05-23 | Ｍｓｄ株式会社 | 新規縮環イミダゾール誘導体 |
| CN101098698A (zh) | 2004-12-01 | 2008-01-02 | 德福根有限公司 | 与离子通道尤其是Kv家族离子通道相互作用的5-羧酰胺基取代的噻唑衍生物 |
| PL1831227T3 (pl) | 2004-12-17 | 2013-10-31 | Glenmark Pharmaceuticals Sa | Nowe związki heterocykliczne użyteczne w leczeniu stanów zapalnych i dolegliwości alergicznych |
| JP2008524255A (ja) | 2004-12-17 | 2008-07-10 | スミスクライン ビーチャム コーポレーション | 化学物質 |
| GB0428235D0 (en) | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Novel compounds |
| KR20060079121A (ko) * | 2004-12-31 | 2006-07-05 | 에스케이케미칼주식회사 | 당뇨 및 비만 치료예방에 유효한 퀴나졸린 유도체 |
| WO2006094235A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| US20060223849A1 (en) | 2005-03-14 | 2006-10-05 | Mjalli Adnan M | Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors |
| WO2006101434A1 (en) * | 2005-03-22 | 2006-09-28 | Astrazeneca Ab | NOVEL TETRAHYDRO-1H-PYRIDO [4,3-b] INDOLE DERIVATIVES AS CB1’ RECEPTOR LIGANDS |
| GB0508472D0 (en) | 2005-04-26 | 2005-06-01 | Glaxo Group Ltd | Compounds |
| EP1907376A2 (en) | 2005-07-05 | 2008-04-09 | Aryx Therapeutics, Inc. | Stereoisomeric pyridyl and pyridonyl compounds and methods for the treatment of gastrointestinal and central nervous system disorders |
| WO2007007688A1 (ja) * | 2005-07-08 | 2007-01-18 | Mochida Pharmaceutical Co., Ltd. | ３,５－ジアミノ－１,２,４－トリアゾール誘導体 |
| JP2009501235A (ja) * | 2005-07-15 | 2009-01-15 | シェーリング コーポレイション | 癌処置において有用なキナゾリン誘導体 |
| DE602006014022D1 (de) | 2005-11-30 | 2010-06-10 | Hoffmann La Roche | 5-substituierte indol-2-carbonsäureamidderivate |
| ES2359739T3 (es) | 2005-11-30 | 2011-05-26 | F. Hoffmann-La Roche Ag | Derivados de indol-2-il-amida 1,5-sustituida. |
| ATE507222T1 (de) | 2005-11-30 | 2011-05-15 | Hoffmann La Roche | 1,1-dioxo-thiomorpholinyl-indolyl-methanon- derivate zur verwendung als h3-modulatoren |
| JP5169220B2 (ja) * | 2005-11-30 | 2013-03-27 | アステラス製薬株式会社 | ２−アミノベンズアミド誘導体 |
| CA2634847A1 (en) | 2005-12-21 | 2007-07-05 | Schering Corporation | Substituted aniline derivatives useful as histamine h3 antagonists |
| JP2009524689A (ja) | 2006-01-25 | 2009-07-02 | スミスクライン ビーチャム コーポレーション | 化合物 |
| PE20070946A1 (es) | 2006-01-25 | 2007-10-16 | Smithkline Beecham Corp | COMPUESTOS DERIVADOS DE IMIDAZO[1,2-a]PIRIDINA COMO MODULADORES DEL RECEPTOR DE QUIMIOQUINA (CXCR4) |
| WO2007098086A2 (en) * | 2006-02-17 | 2007-08-30 | Avalon Pharmaceuticals | Hydroxypiperidine derivatives and uses thereof |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| BRPI0710588A2 (pt) * | 2006-04-12 | 2012-06-19 | Hoffmann La Roche | compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação de receptores de h3, uso dos compostos, e métodos para o tratamento ou prevenção de obesidade, e de diabetes do tipo ii |
| PT2463283E (pt) | 2006-04-20 | 2014-08-27 | Pfizer Prod Inc | Compostos heterocíclicos de fenil amido condensados para a prevenção e tratamento de doenças mediadas pela glucoquinase |
| AU2007260527A1 (en) | 2006-06-12 | 2007-12-21 | Merck Frosst Canada Ltd. | Azetidine derivatives as inhibitors of stearoyl-coenzyme A delta-9 desaturase |
| US7754745B2 (en) | 2006-06-13 | 2010-07-13 | Merck Frosst Canada Ltd. | Azacyclopentane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| TW200821303A (en) | 2006-08-08 | 2008-05-16 | Speedel Experimenta Ag | Organic compounds |
| ES2627221T3 (es) | 2006-12-28 | 2017-07-27 | Rigel Pharmaceuticals, Inc. | Compuestos de heterocicloalquiloxibenzamida N-sustituidos y métodos de uso |
| JP2010527915A (ja) | 2007-04-26 | 2010-08-19 | アバロン ファーマシューティカルズ，インコーポレイテッド | 多重環化合物及びその用途 |
| NZ585137A (en) * | 2007-10-25 | 2012-07-27 | Exelixis Inc | Tropane compounds useful as hsp90 inhibitors |
| CA2705947C (en) * | 2007-11-16 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| ES2553340T3 (es) * | 2007-12-12 | 2015-12-07 | Rigel Pharmaceuticals, Inc. | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
| CN112079769A (zh) * | 2008-04-23 | 2020-12-15 | 里格尔药品股份有限公司 | 用于治疗代谢障碍的甲酰胺化合物 |
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| CA2707047A1 (en) | 2009-06-18 |
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| EP2231666B1 (en) | 2015-07-29 |
| JP2011506480A (ja) | 2011-03-03 |
| HK1148524A1 (en) | 2011-09-09 |
| CA2707047C (en) | 2017-11-28 |
| US8129390B2 (en) | 2012-03-06 |
| WO2009076631A1 (en) | 2009-06-18 |
| US8557822B2 (en) | 2013-10-15 |
| US20120108606A1 (en) | 2012-05-03 |
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