JP2015527399A5 - - Google Patents
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- Publication number
- JP2015527399A5 JP2015527399A5 JP2015531237A JP2015531237A JP2015527399A5 JP 2015527399 A5 JP2015527399 A5 JP 2015527399A5 JP 2015531237 A JP2015531237 A JP 2015531237A JP 2015531237 A JP2015531237 A JP 2015531237A JP 2015527399 A5 JP2015527399 A5 JP 2015527399A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoropyrazolo
- indol
- indole
- dihydropyrazolo
- fluoro
- 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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- -1 thiopheneyl Chemical group 0.000 claims 117
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229960002965 pravastatin Drugs 0.000 claims 5
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000005899 2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl group Chemical group 0.000 claims 2
- TZDONXAHPXKEGZ-UHFFFAOYSA-N 6-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-1-(2-hydroxyethyl)-5-methyl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N(CCO)C(=O)N2)=C2N=C1C TZDONXAHPXKEGZ-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims 2
- 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000011661 metabolic syndrome X Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- VVQSCGIRSJAVKW-AJLCLMPTSA-N (1r,2r,5s)-3-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CN=C(N2[C@H]([C@@H]3C[C@@H]3C2)C(N)=O)N=C1C VVQSCGIRSJAVKW-AJLCLMPTSA-N 0.000 claims 1
- VVQSCGIRSJAVKW-QAMHXRKUSA-N (1r,2s,5s)-3-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CN=C(N2[C@@H]([C@@H]3C[C@@H]3C2)C(N)=O)N=C1C VVQSCGIRSJAVKW-QAMHXRKUSA-N 0.000 claims 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- JVXZMZFHASCFTM-SECBINFHSA-N (2r)-1-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]amino]propan-2-ol Chemical compound CC1=NC(NC[C@H](O)C)=NC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 JVXZMZFHASCFTM-SECBINFHSA-N 0.000 claims 1
- RNDRRILNXQNKKZ-SNVBAGLBSA-N (2r)-1-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-6-methylpyridin-2-yl]amino]propan-2-ol Chemical compound CC1=NC(NC[C@H](O)C)=CC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 RNDRRILNXQNKKZ-SNVBAGLBSA-N 0.000 claims 1
- MYNYHVTZJXRKKZ-GFCCVEGCSA-N (2r)-3-[6-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-5-methylimidazo[4,5-b]pyridin-3-yl]propane-1,2-diol Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N=CN2C[C@@H](O)CO)=C2N=C1C MYNYHVTZJXRKKZ-GFCCVEGCSA-N 0.000 claims 1
- LKJUSTPUAXMOMO-LLVKDONJSA-N (2r)-3-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]amino]propane-1,2-diol Chemical compound CC1=NC(NC[C@@H](O)CO)=NC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 LKJUSTPUAXMOMO-LLVKDONJSA-N 0.000 claims 1
- JVXZMZFHASCFTM-VIFPVBQESA-N (2s)-1-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]amino]propan-2-ol Chemical compound CC1=NC(NC[C@@H](O)C)=NC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 JVXZMZFHASCFTM-VIFPVBQESA-N 0.000 claims 1
- XFLZIIASAHFMPT-VIFPVBQESA-N (2s)-2-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]amino]propan-1-ol Chemical compound CC1=NC(N[C@H](CO)C)=NC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 XFLZIIASAHFMPT-VIFPVBQESA-N 0.000 claims 1
- MYNYHVTZJXRKKZ-LBPRGKRZSA-N (2s)-3-[6-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-5-methylimidazo[4,5-b]pyridin-3-yl]propane-1,2-diol Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N=CN2C[C@H](O)CO)=C2N=C1C MYNYHVTZJXRKKZ-LBPRGKRZSA-N 0.000 claims 1
- GFMMMVIGRGRSEL-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyridin-2-yl]methanone Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=CC=1C(=O)N1CC(N)C1 GFMMMVIGRGRSEL-UHFFFAOYSA-N 0.000 claims 1
- CTBMTGKGHSVVLR-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-6-methylpyridin-2-yl]methanone Chemical compound C=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1C(=O)N1CC(N)C1 CTBMTGKGHSVVLR-UHFFFAOYSA-N 0.000 claims 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims 1
- ZRTDJGCQJYSPSV-CYBMUJFWSA-N (3r)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]piperidin-3-ol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CCC[C@@H](O)C1 ZRTDJGCQJYSPSV-CYBMUJFWSA-N 0.000 claims 1
- KKFJVSMJOYXFQJ-GFCCVEGCSA-N (3r)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]pyrrolidin-3-ol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CC[C@@H](O)C1 KKFJVSMJOYXFQJ-GFCCVEGCSA-N 0.000 claims 1
- BVWYKVYJKDAOHM-CYBMUJFWSA-N (3r)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-6-methylpyridin-2-yl]pyrrolidin-3-ol Chemical compound C=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CC[C@@H](O)C1 BVWYKVYJKDAOHM-CYBMUJFWSA-N 0.000 claims 1
- ZPZQUANGRXUVAS-HZPDHXFCSA-N (3r,4r)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]pyrrolidine-3,4-diol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1C[C@@H](O)[C@H](O)C1 ZPZQUANGRXUVAS-HZPDHXFCSA-N 0.000 claims 1
- ZRTDJGCQJYSPSV-ZDUSSCGKSA-N (3s)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]piperidin-3-ol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CCC[C@H](O)C1 ZRTDJGCQJYSPSV-ZDUSSCGKSA-N 0.000 claims 1
- KKFJVSMJOYXFQJ-LBPRGKRZSA-N (3s)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]pyrrolidin-3-ol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CC[C@H](O)C1 KKFJVSMJOYXFQJ-LBPRGKRZSA-N 0.000 claims 1
- BVWYKVYJKDAOHM-ZDUSSCGKSA-N (3s)-1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-6-methylpyridin-2-yl]pyrrolidin-3-ol Chemical compound C=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CC[C@H](O)C1 BVWYKVYJKDAOHM-ZDUSSCGKSA-N 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 claims 1
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims 1
- JAIZHQLBZUGIQV-UHFFFAOYSA-N 1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]azetidin-3-ol Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CC(O)C1 JAIZHQLBZUGIQV-UHFFFAOYSA-N 0.000 claims 1
- CDKNKEYEZIFKOB-UHFFFAOYSA-N 1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]piperidine-4-carbonitrile Chemical compound N=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1N1CCC(C#N)CC1 CDKNKEYEZIFKOB-UHFFFAOYSA-N 0.000 claims 1
- KKYCXXHACYYMAT-UHFFFAOYSA-N 1-[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-6-methylpyridine-2-carbonyl]azetidine-3-carbonitrile Chemical compound C=1C=C(N2C3=CC=C(F)C=C3C=3NN=CC=32)C(C)=NC=1C(=O)N1CC(C#N)C1 KKYCXXHACYYMAT-UHFFFAOYSA-N 0.000 claims 1
- VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 claims 1
- RJMOCFHZZVNPMG-UHFFFAOYSA-N 2-[6-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-5-methylimidazo[4,5-b]pyridin-3-yl]ethanol Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N=CN2CCO)=C2N=C1C RJMOCFHZZVNPMG-UHFFFAOYSA-N 0.000 claims 1
- JUQPWBIRVPOLPW-UHFFFAOYSA-N 2-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyridin-2-yl]-methylamino]ethanol Chemical compound C1=NC(N(CCO)C)=CC(C)=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 JUQPWBIRVPOLPW-UHFFFAOYSA-N 0.000 claims 1
- HRQSQNPDQBTKRC-UHFFFAOYSA-N 2-[[5-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-4-methylpyrimidin-2-yl]amino]ethanol Chemical compound CC1=NC(NCCO)=NC=C1N1C2=CC=C(F)C=C2C2=C1C=NN2 HRQSQNPDQBTKRC-UHFFFAOYSA-N 0.000 claims 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- NTFZDFZVGNCXQP-UHFFFAOYSA-N 3-[6-(7-fluoro-1h-pyrazolo[4,3-b]indol-4-yl)-5-methylimidazo[4,5-b]pyridin-3-yl]propan-1-ol Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N=CN2CCCO)=C2N=C1C NTFZDFZVGNCXQP-UHFFFAOYSA-N 0.000 claims 1
- BXLCENGNDVFRAZ-UHFFFAOYSA-N 3-hydroxyazetidine-1-carbaldehyde Chemical compound OC1CN(C=O)C1 BXLCENGNDVFRAZ-UHFFFAOYSA-N 0.000 claims 1
- FPGGLMIYNLQOID-UHFFFAOYSA-N 3h-pyridin-2-one Chemical compound O=C1CC=CC=N1 FPGGLMIYNLQOID-UHFFFAOYSA-N 0.000 claims 1
- PSXVTQZWNCZZEK-UHFFFAOYSA-N 4-(1,4-dimethylindazol-5-yl)-7-fluoro-1h-pyrazolo[4,3-b]indole Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=C(C)C(C=NN2C)=C2C=C1 PSXVTQZWNCZZEK-UHFFFAOYSA-N 0.000 claims 1
- OGFYDTCSKYEYQW-UHFFFAOYSA-N 4-(1,5-dimethylindazol-6-yl)-7-fluoro-1h-pyrazolo[4,3-b]indole Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC(N(C)N=C2)=C2C=C1C OGFYDTCSKYEYQW-UHFFFAOYSA-N 0.000 claims 1
- FSDBXNSGEOIMLV-UHFFFAOYSA-N 4-(1-ethyl-3,5-dimethylpyrazol-4-yl)-7-fluoro-1h-pyrazolo[4,3-b]indole Chemical compound CCN1N=C(C)C(N2C3=CC=C(F)C=C3C=3NN=CC=32)=C1C FSDBXNSGEOIMLV-UHFFFAOYSA-N 0.000 claims 1
- KUOHQQCPDGBENS-UHFFFAOYSA-N 4-(2,5-dimethylindazol-6-yl)-7-fluoro-1h-pyrazolo[4,3-b]indole Chemical compound C1=2C=NNC=2C2=CC(F)=CC=C2N1C1=CC2=NN(C)C=C2C=C1C KUOHQQCPDGBENS-UHFFFAOYSA-N 0.000 claims 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
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- QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 claims 1
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| US201261698369P | 2012-09-07 | 2012-09-07 | |
| US61/698,369 | 2012-09-07 | ||
| PCT/US2013/058527 WO2014039831A1 (en) | 2012-09-07 | 2013-09-06 | SUBSTITUTED-1,4-DIHYDROPYRAZOLO[4,3-b]INDOLES |
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| EP2723746A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| BR112015012454B1 (pt) | 2012-12-07 | 2022-07-05 | Vertex Pharmaceuticals Incorporated | Compostos inibidores de atr quinase, seu uso e composição farmacêutica compreendendo os mesmos |
| WO2014143241A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2014143242A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2014143240A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| ES2768678T3 (es) | 2013-12-06 | 2020-06-23 | Vertex Pharma | Compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inhibidor de la ATR quinasa, su preparación, diferentes formas sólidas y derivados radiomarcados de las mismas |
| ES2777608T3 (es) | 2014-06-05 | 2020-08-05 | Vertex Pharma | Derivados radiomarcados de un compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-carboxamida útiles como inhibidores de ATR cinasa, la preparación de dicho compuesto y diferentes formas sólidas del mismo |
| KR20170016498A (ko) | 2014-06-17 | 2017-02-13 | 버텍스 파마슈티칼스 인코포레이티드 | Chk1 및 atr 저해제의 병용물을 사용하는 암의 치료 방법 |
| EP3288556A4 (en) | 2015-04-29 | 2018-09-19 | Dexcel Pharma Technologies Ltd. | Orally disintegrating compositions |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| US10076494B2 (en) | 2016-06-16 | 2018-09-18 | Dexcel Pharma Technologies Ltd. | Stable orally disintegrating pharmaceutical compositions |
| US20210221784A1 (en) * | 2018-02-05 | 2021-07-22 | Université De Strasbourg | Compounds and compositions for the treatment of pain |
| CA3144527A1 (en) * | 2019-08-06 | 2021-02-11 | Domain Therapeutics | 5-heteroaryl-pyridin-2-amine confounds as neuropeptide ff receptor antagonists |
| CN113372281A (zh) * | 2020-03-09 | 2021-09-10 | 河北中科金辉药业有限公司 | 一种特硝唑的合成方法 |
| AU2021268094A1 (en) * | 2020-05-08 | 2022-10-27 | Cancer Research Technology Ltd. | Tricyclic heterocycles useful as TEAD binders |
| IL298005A (en) * | 2020-05-08 | 2023-01-01 | Merck Patent Gmbh | Tricyclic heterocycles compounds, their preparation and pharmaceutical compositions containing them |
| AU2021401996A1 (en) * | 2020-12-14 | 2023-07-13 | Kinoxis Therapeutics Pty Ltd | Oxytocin receptor modulators |
| CA3218932A1 (en) * | 2021-05-05 | 2022-11-10 | Merck Patent Gmbh | 2,8-dihydropyrazolo[3,4-b]indole derivatives for use in the treatment of cancer |
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| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| DK0638071T3 (da) | 1992-12-28 | 1997-10-27 | Eisai Co Ltd | Heterocykliske carboxylsyrederivater, der bindes til retenoidreceptorer (RAR) |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| WO2000007996A2 (en) | 1998-08-07 | 2000-02-17 | Chiron Corporation | Pyrazoles as estrogen receptor modulators |
| US6462036B1 (en) | 1998-11-06 | 2002-10-08 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
| TR200102277T2 (tr) * | 1998-11-06 | 2002-01-21 | Basf Aktiengesellschaft Ag. | Üç halkalı (Trisiklik) pirazol türevleri |
| US6297238B1 (en) | 1999-04-06 | 2001-10-02 | Basf Aktiengesellschaft | Therapeutic agents |
| EP1341783A1 (en) | 2000-11-21 | 2003-09-10 | Smithkline Beecham Plc | Isoquinoline derivatives useful in the treatment of cns disorders |
| GB0111186D0 (en) | 2001-05-08 | 2001-06-27 | Smithkline Beecham Plc | Novel compounds |
| CA2486097A1 (en) | 2002-05-15 | 2003-11-27 | Janssen Pharmaceutica N.V. | N-substituted tricyclic 3-aminopyrazoles as pdfg receptor inhibitors |
| EP1603885A1 (en) | 2003-03-07 | 2005-12-14 | Abbott Laboratories | Fused tri and tetra-cyclic pyrazole kinase inhibitors |
| ES2551293T3 (es) | 2004-03-24 | 2015-11-17 | Abbvie Inc. | Inhibidores de quinasas de pirazol tricíclicos |
| US7816536B2 (en) | 2005-06-10 | 2010-10-19 | The Research Foundation Of State University Of New York | 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same |
| WO2008008650A1 (en) | 2006-07-10 | 2008-01-17 | Indiana University Research And Technology Corporation | Methods for treating cystic kidney diseases |
| CN100586932C (zh) | 2007-01-26 | 2010-02-03 | 中国医学科学院医药生物技术研究所 | 抗肿瘤化合物及其制备方法 |
| US20120004162A1 (en) | 2008-12-04 | 2012-01-05 | Vath James E | Methods of Treating an Overweight or Obese Subject |
| WO2010065883A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Method of treating an overweight or obese subject |
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- 2013-09-06 WO PCT/US2013/058527 patent/WO2014039831A1/en not_active Ceased
- 2013-09-06 JP JP2015531237A patent/JP2015527399A/ja not_active Abandoned
- 2013-09-06 EP EP13762702.2A patent/EP2909212B1/en active Active
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