CA2437215A1 - Composes de dihydropyrazolopyridine et leur utilisation pharmaceutique - Google Patents

Composes de dihydropyrazolopyridine et leur utilisation pharmaceutique Download PDF

Info

Publication number: CA2437215A1
Authority: CA; Canada
Prior art keywords: dihydro; pyridine; pyrazolo; ethyl; carboxylate
Prior art date: 2001-02-02
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

Application number

CA002437215A

Other languages

English (en)

Inventor

Toshiyuki Kohara

Kenji Fukunaga

Masatake Fujimura

Tokushi Hanano

Hirotaka Okabe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Tanabe Pharma Corp

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2001-02-02

Filing date

2002-02-01

Publication date

2002-08-15

2002-02-01 Application filed by Individual filed Critical Individual

2002-08-15 Publication of CA2437215A1 publication Critical patent/CA2437215A1/fr

Status Abandoned legal-status Critical Current

Links

KKIRMHFZGVTSNH-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazolo[4,3-b]pyridine Chemical class C1=CN=C2CNNC2=C1 KKIRMHFZGVTSNH-UHFFFAOYSA-N 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 416
150000003839 salts Chemical class 0.000 claims abstract description 35
239000003814 drug Substances 0.000 claims abstract description 25
108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims abstract description 8
230000002265 prevention Effects 0.000 claims abstract description 8
208000002249 Diabetes Complications Diseases 0.000 claims abstract description 7
230000004770 neurodegeneration Effects 0.000 claims abstract description 7
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
206010012655 Diabetic complications Diseases 0.000 claims abstract description 5
230000000091 immunopotentiator Effects 0.000 claims abstract description 5
102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims abstract 3
-1 dihydropyrazolopyridine compound Chemical class 0.000 claims description 155
125000000217 alkyl group Chemical group 0.000 claims description 65
125000001424 substituent group Chemical group 0.000 claims description 52
229920006395 saturated elastomer Polymers 0.000 claims description 45
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
125000003884 phenylalkyl group Chemical group 0.000 claims description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000005359 phenoxyalkyl group Chemical group 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
239000003112 inhibitor Substances 0.000 claims description 11
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 10
201000006474 Brain Ischemia Diseases 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 9
125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 9
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 9
208000014644 Brain disease Diseases 0.000 claims description 8
208000032274 Encephalopathy Diseases 0.000 claims description 8
201000011240 Frontotemporal dementia Diseases 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
UCYSGOPMGLTVDN-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC=3NN=CC=32)CCC)=C1 UCYSGOPMGLTVDN-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004103 aminoalkyl group Chemical group 0.000 claims description 7
208000028683 bipolar I disease Diseases 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000002431 aminoalkoxy group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002071 phenylalkoxy group Chemical group 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
208000030507 AIDS Diseases 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 5
208000027089 Parkinsonian disease Diseases 0.000 claims description 5
206010034010 Parkinsonism Diseases 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 5
YBJHPLNWQCXDIS-UHFFFAOYSA-N ethyl 4-(2,1,3-benzoxadiazol-4-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC2=NON=C2C(C2C(=C(NC3=NNC=C32)CCC)C(=O)OCC)=C1 YBJHPLNWQCXDIS-UHFFFAOYSA-N 0.000 claims description 5
CIIFSJGRWIDILP-UHFFFAOYSA-N ethyl 4-(3,4-dihydro-2h-chromen-8-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1CCOC2=C1C=CC=C2C1C(C(=O)OCC)=C(CCC)NC2=NNC=C21 CIIFSJGRWIDILP-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
ONQBGGZJUQUSAL-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-(hydroxymethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC3=NNC=C32)CO)=C1 ONQBGGZJUQUSAL-UHFFFAOYSA-N 0.000 claims description 4
IFLOPPYMWXNYJL-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-phenyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound N1C2=NNC=C2C(C=2C3=NON=C3C=CC=2)C(C#N)=C1C1=CC=CC=C1 IFLOPPYMWXNYJL-UHFFFAOYSA-N 0.000 claims description 4
208000020925 Bipolar disease Diseases 0.000 claims description 4
208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 4
206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
208000011990 Corticobasal Degeneration Diseases 0.000 claims description 4
201000010374 Down Syndrome Diseases 0.000 claims description 4
206010033799 Paralysis Diseases 0.000 claims description 4
208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 4
206010044688 Trisomy 21 Diseases 0.000 claims description 4
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
206010008118 cerebral infarction Diseases 0.000 claims description 4
208000026106 cerebrovascular disease Diseases 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
NCPSVISZMIFVEF-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1OC NCPSVISZMIFVEF-UHFFFAOYSA-N 0.000 claims description 4
230000000302 ischemic effect Effects 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 4
230000000750 progressive effect Effects 0.000 claims description 4
UELDKXIYSJQVFF-UHFFFAOYSA-N 2-o-tert-butyl 5-o-ethyl 4-(2-chlorophenyl)-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-2,5-dicarboxylate Chemical compound C12=CN(C(=O)OC(C)(C)C)N=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl UELDKXIYSJQVFF-UHFFFAOYSA-N 0.000 claims description 3
BHGJCAGSPBFYGF-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-propan-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC3=NNC=C32)C(C)C)=C1 BHGJCAGSPBFYGF-UHFFFAOYSA-N 0.000 claims description 3
VTHGJIMNHWCIQI-UHFFFAOYSA-N 4-(2,1,3-benzoxadiazol-4-yl)-6-thiophen-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound N1C2=NNC=C2C(C=2C3=NON=C3C=CC=2)C(C#N)=C1C1=CC=CS1 VTHGJIMNHWCIQI-UHFFFAOYSA-N 0.000 claims description 3
SLYQLCHINAYIKB-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-cyclopropyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound BrC1=C(C#N)C=CC=C1C1C(C#N)=C(C2CC2)NC2=NNC=C21 SLYQLCHINAYIKB-UHFFFAOYSA-N 0.000 claims description 3
IHNWQNHNECXIPG-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-phenyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound BrC1=C(C#N)C=CC=C1C1C(C#N)=C(C=2C=CC=CC=2)NC2=NNC=C21 IHNWQNHNECXIPG-UHFFFAOYSA-N 0.000 claims description 3
WYJFCHZMQYOKAT-UHFFFAOYSA-N 4-(2-bromo-3-cyanophenyl)-6-propan-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C12=CNN=C2NC(C(C)C)=C(C#N)C1C1=CC=CC(C#N)=C1Br WYJFCHZMQYOKAT-UHFFFAOYSA-N 0.000 claims description 3
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000009829 Lewy Body Disease Diseases 0.000 claims description 3
201000002832 Lewy body dementia Diseases 0.000 claims description 3
208000037658 Parkinson-dementia complex of Guam Diseases 0.000 claims description 3
INXXFONIOPBQOU-UHFFFAOYSA-N ethyl 4-(2-bromo-3-cyanophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C#N)=C1Br INXXFONIOPBQOU-UHFFFAOYSA-N 0.000 claims description 3
AZLMKLCCQWYPBB-UHFFFAOYSA-N ethyl 4-(2-bromo-3-nitrophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC([N+]([O-])=O)=C1Br AZLMKLCCQWYPBB-UHFFFAOYSA-N 0.000 claims description 3
PEBLOVKPEUXWBD-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-thiophen-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C=2SC=CC=2)NC2=NNC=C2C1C1=CC=CC=C1Cl PEBLOVKPEUXWBD-UHFFFAOYSA-N 0.000 claims description 3
SSTRTCQWQZMHAK-UHFFFAOYSA-N ethyl 4-naphthalen-1-yl-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC=C2C(C3C(=C(NC4=NNC=C43)CCC)C(=O)OCC)=CC=CC2=C1 SSTRTCQWQZMHAK-UHFFFAOYSA-N 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
KUTLOTKOBQKTBI-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-5-nitro-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine Chemical compound C12=CNN=C2NC(CCC)=C([N+]([O-])=O)C1C1=CC=CC(Cl)=C1Cl KUTLOTKOBQKTBI-UHFFFAOYSA-N 0.000 claims description 2
KOYAPHWQMYZVSZ-UHFFFAOYSA-N 4-(2-bromo-3-nitrophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C12=CNN=C2NC(CCC)=C(C#N)C1C1=CC=CC([N+]([O-])=O)=C1Br KOYAPHWQMYZVSZ-UHFFFAOYSA-N 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
SLAKQKWARQMTOM-UHFFFAOYSA-N ethyl 4-(2,1,3-benzoxadiazol-4-yl)-6-ethyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC2=NON=C2C(C2C3=CNN=C3NC(CC)=C2C(=O)OCC)=C1 SLAKQKWARQMTOM-UHFFFAOYSA-N 0.000 claims description 2
VCXIIWLAPLBGLF-UHFFFAOYSA-N ethyl 4-[2-chloro-3-(trifluoromethyl)phenyl]-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C(F)(F)F)=C1Cl VCXIIWLAPLBGLF-UHFFFAOYSA-N 0.000 claims description 2
208000013403 hyperactivity Diseases 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims 1
102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 abstract description 45
108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 abstract description 45
230000002401 inhibitory effect Effects 0.000 abstract description 11
206010012601 diabetes mellitus Diseases 0.000 abstract description 3
150000004677 hydrates Chemical class 0.000 abstract description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 698
238000005160 1H NMR spectroscopy Methods 0.000 description 353
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 263
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
239000000243 solution Substances 0.000 description 119
239000000203 mixture Substances 0.000 description 117
239000013078 crystal Substances 0.000 description 113
KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 78
239000002904 solvent Substances 0.000 description 73
UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 68
239000003480 eluent Substances 0.000 description 67
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
238000010898 silica gel chromatography Methods 0.000 description 62
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 59
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 58
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 57
239000011541 reaction mixture Substances 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
239000003921 oil Substances 0.000 description 50
235000019198 oils Nutrition 0.000 description 50
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 38
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
YBBRQAXNTWMMFZ-UHFFFAOYSA-N 2,1,3-benzoxadiazole-4-carbaldehyde Chemical compound O=CC1=CC=CC2=NON=C12 YBBRQAXNTWMMFZ-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
238000010992 reflux Methods 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
150000001721 carbon Chemical group 0.000 description 26
229910052799 carbon Inorganic materials 0.000 description 26
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
238000001816 cooling Methods 0.000 description 25
230000000694 effects Effects 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
VTSKCFROIFGSPJ-UHFFFAOYSA-N 4h-pyrazolo[3,4-b]pyridine-5-carboxylic acid Chemical compound C1C(C(=O)O)=CN=C2N=NC=C21 VTSKCFROIFGSPJ-UHFFFAOYSA-N 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
239000011780 sodium chloride Substances 0.000 description 23
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 22
GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 20
238000000354 decomposition reaction Methods 0.000 description 20
238000001914 filtration Methods 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 18
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
PHZMJSCJHNIUSL-UHFFFAOYSA-N 2-bromo-3-formylbenzonitrile Chemical compound BrC1=C(C=O)C=CC=C1C#N PHZMJSCJHNIUSL-UHFFFAOYSA-N 0.000 description 13
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 13
229940095102 methyl benzoate Drugs 0.000 description 13
LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 12
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125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
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235000003704 aspartic acid Nutrition 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
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PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000001046 cacaotero Nutrition 0.000 description 1
CHRHZFQUDFAQEQ-UHFFFAOYSA-L calcium;2-hydroxyacetate Chemical compound [Ca+2].OCC([O-])=O.OCC([O-])=O CHRHZFQUDFAQEQ-UHFFFAOYSA-L 0.000 description 1
239000002775 capsule Substances 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
230000034994 death Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000010454 developmental mechanism Effects 0.000 description 1
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
QBEGYEWDTSUVHH-UHFFFAOYSA-P diazanium;cerium(3+);pentanitrate Chemical compound [NH4+].[NH4+].[Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O QBEGYEWDTSUVHH-UHFFFAOYSA-P 0.000 description 1
QRDYOEIDRGVJJK-UHFFFAOYSA-N diethyl 4-(2-chlorophenyl)-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-2,5-dicarboxylate Chemical compound C12=CN(C(=O)OCC)N=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl QRDYOEIDRGVJJK-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
SMPGOXHTDARPIQ-VOTSOKGWSA-N ethyl (e)-3-[4-(2,1,3-benzoxadiazol-4-yl)-5-cyano-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-6-yl]prop-2-enoate Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC3=NNC=C32)/C=C/C(=O)OCC)=C1 SMPGOXHTDARPIQ-VOTSOKGWSA-N 0.000 description 1
AKTIKZJGSYDEQF-UHFFFAOYSA-N ethyl 1-acetyl-4-(2-chlorophenyl)-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2C=NN(C(C)=O)C=2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl AKTIKZJGSYDEQF-UHFFFAOYSA-N 0.000 description 1
MEHJDVPESNTTTB-UHFFFAOYSA-N ethyl 1-benzoyl-4-(2-chlorophenyl)-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2NC(CCC)=C(C(=O)OCC)C(C=3C(=CC=CC=3)Cl)C=2C=NN1C(=O)C1=CC=CC=C1 MEHJDVPESNTTTB-UHFFFAOYSA-N 0.000 description 1
RRNCTNTWEKNRAE-UHFFFAOYSA-N ethyl 1-methyl-4-naphthalen-1-yl-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC=C2C(C3C(=C(NC=4N(C)N=CC=43)CCC)C(=O)OCC)=CC=CC2=C1 RRNCTNTWEKNRAE-UHFFFAOYSA-N 0.000 description 1
VMYQJDCENDEETH-UHFFFAOYSA-N ethyl 2-[tert-butyl(dimethyl)silyl]oxyacetate Chemical compound CCOC(=O)CO[Si](C)(C)C(C)(C)C VMYQJDCENDEETH-UHFFFAOYSA-N 0.000 description 1
OMCRNVXNMNNBTR-UHFFFAOYSA-N ethyl 2-acetyl-4-(2-chlorophenyl)-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CN(C(C)=O)N=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl OMCRNVXNMNNBTR-UHFFFAOYSA-N 0.000 description 1
LCDPZBBVXQGCBO-UHFFFAOYSA-N ethyl 2-benzoyl-4-(2-chlorophenyl)-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound N1=C2NC(CCC)=C(C(=O)OCC)C(C=3C(=CC=CC=3)Cl)C2=CN1C(=O)C1=CC=CC=C1 LCDPZBBVXQGCBO-UHFFFAOYSA-N 0.000 description 1
PHSWWKXTGAJPCQ-UHFFFAOYSA-N ethyl 2-phenylmethoxyacetate Chemical compound CCOC(=O)COCC1=CC=CC=C1 PHSWWKXTGAJPCQ-UHFFFAOYSA-N 0.000 description 1
JHCGIFHFABXVNQ-UHFFFAOYSA-N ethyl 3,5-dioxo-5-phenylpentanoate Chemical compound CCOC(=O)CC(=O)CC(=O)C1=CC=CC=C1 JHCGIFHFABXVNQ-UHFFFAOYSA-N 0.000 description 1
KRAHENMBSVAAHD-UHFFFAOYSA-N ethyl 3-(4-methoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(OC)C=C1 KRAHENMBSVAAHD-UHFFFAOYSA-N 0.000 description 1
JGFXWPXQPGHAPD-UHFFFAOYSA-N ethyl 3-[4-(2,1,3-benzoxadiazol-4-yl)-5-cyano-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-6-yl]propanoate Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC3=NNC=C32)CCC(=O)OCC)=C1 JGFXWPXQPGHAPD-UHFFFAOYSA-N 0.000 description 1
DCPDNQZEMGSDBF-UHFFFAOYSA-N ethyl 3-[4-(2-chlorophenyl)-5-cyano-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-6-yl]propanoate Chemical compound C12=CNN=C2NC(CCC(=O)OCC)=C(C#N)C1C1=CC=CC=C1Cl DCPDNQZEMGSDBF-UHFFFAOYSA-N 0.000 description 1
VKSDKUXHVLZDHO-UHFFFAOYSA-N ethyl 3-oxo-3-thiophen-2-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CS1 VKSDKUXHVLZDHO-UHFFFAOYSA-N 0.000 description 1
BOZNWXQZCYZCSH-UHFFFAOYSA-N ethyl 3-oxo-4-phenylbutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=CC=C1 BOZNWXQZCYZCSH-UHFFFAOYSA-N 0.000 description 1
MUIQNPRTYFQBAT-UHFFFAOYSA-N ethyl 4,4-dimethoxy-2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC(OC)OC MUIQNPRTYFQBAT-UHFFFAOYSA-N 0.000 description 1
GPEOKYAEAJJZHD-UHFFFAOYSA-N ethyl 4-(1-benzothiophen-3-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC=C2C(C3C(=C(NC4=NNC=C43)CCC)C(=O)OCC)=CSC2=C1 GPEOKYAEAJJZHD-UHFFFAOYSA-N 0.000 description 1
NFLXFZBBYRLVEM-UHFFFAOYSA-N ethyl 4-(1-benzothiophen-7-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC2=C1SC=C2 NFLXFZBBYRLVEM-UHFFFAOYSA-N 0.000 description 1
NHVCMPLVRMZJLU-UHFFFAOYSA-N ethyl 4-(1-methylimidazol-2-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=NC=CN1C NHVCMPLVRMZJLU-UHFFFAOYSA-N 0.000 description 1
ABDZMJWVYULKPI-UHFFFAOYSA-N ethyl 4-(1h-imidazol-5-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CN=CN1 ABDZMJWVYULKPI-UHFFFAOYSA-N 0.000 description 1
VCTYEJDPLHRHSI-UHFFFAOYSA-N ethyl 4-(2,1,3-benzothiadiazol-4-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC2=NSN=C2C(C2C(=C(NC3=NNC=C32)CCC)C(=O)OCC)=C1 VCTYEJDPLHRHSI-UHFFFAOYSA-N 0.000 description 1
KQWFAMQUHVSNTQ-UHFFFAOYSA-N ethyl 4-(2,1,3-benzoxadiazol-4-yl)-6-butyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC2=NON=C2C(C2C(=C(NC3=NNC=C32)CCCC)C(=O)OCC)=C1 KQWFAMQUHVSNTQ-UHFFFAOYSA-N 0.000 description 1
FTEZFKDOFZOGBT-UHFFFAOYSA-N ethyl 4-(2,1,3-benzoxadiazol-4-yl)-6-methyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC2=NON=C2C(C2C3=CNN=C3NC(C)=C2C(=O)OCC)=C1 FTEZFKDOFZOGBT-UHFFFAOYSA-N 0.000 description 1
ZHEOMHUSXSFIPP-UHFFFAOYSA-N ethyl 4-(2,3-dibromophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(Br)=C1Br ZHEOMHUSXSFIPP-UHFFFAOYSA-N 0.000 description 1
SMTSOEXZRYCBBQ-UHFFFAOYSA-N ethyl 4-(2,3-dichlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(Cl)=C1Cl SMTSOEXZRYCBBQ-UHFFFAOYSA-N 0.000 description 1
HDBFRLMUTILTKS-UHFFFAOYSA-N ethyl 4-(2,3-difluorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(F)=C1F HDBFRLMUTILTKS-UHFFFAOYSA-N 0.000 description 1
NRUYJXPOAPORRI-UHFFFAOYSA-N ethyl 4-(2,3-dihydro-1-benzofuran-7-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNNC2=NC(CCC)=C(C(=O)OCC)C1C1=CC=CC2=C1OCC2 NRUYJXPOAPORRI-UHFFFAOYSA-N 0.000 description 1
IRPWSDMGKCZXRO-UHFFFAOYSA-N ethyl 4-(2,3-dihydro-1h-inden-4-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC2=C1CCC2 IRPWSDMGKCZXRO-UHFFFAOYSA-N 0.000 description 1
KBIQIZCZMVFPGW-UHFFFAOYSA-N ethyl 4-(2,5-dichlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC(Cl)=CC=C1Cl KBIQIZCZMVFPGW-UHFFFAOYSA-N 0.000 description 1
PILKGFBYYMCHKW-UHFFFAOYSA-N ethyl 4-(2,5-dimethoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC(OC)=CC=C1OC PILKGFBYYMCHKW-UHFFFAOYSA-N 0.000 description 1
UHNCYQUAMNBLDK-UHFFFAOYSA-N ethyl 4-(2,6-dichlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=C(Cl)C=CC=C1Cl UHNCYQUAMNBLDK-UHFFFAOYSA-N 0.000 description 1
CLMFSJUKZBCWLC-UHFFFAOYSA-N ethyl 4-(2-aminophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1N CLMFSJUKZBCWLC-UHFFFAOYSA-N 0.000 description 1
DLRJPQMFHZDVRA-UHFFFAOYSA-N ethyl 4-(2-bromo-3-cyanophenyl)-6-cyclopropyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C2CC2)NC2=NNC=C2C1C1=CC=CC(C#N)=C1Br DLRJPQMFHZDVRA-UHFFFAOYSA-N 0.000 description 1
WHRKEGSCYGZTOF-UHFFFAOYSA-N ethyl 4-(2-bromophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Br WHRKEGSCYGZTOF-UHFFFAOYSA-N 0.000 description 1
JJRAYPCMMNUGLV-UHFFFAOYSA-N ethyl 4-(2-butoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCCCOC1=CC=CC=C1C1C(C(=O)OCC)=C(CCC)NC2=NNC=C21 JJRAYPCMMNUGLV-UHFFFAOYSA-N 0.000 description 1
KCNDBNBMPRCNIE-UHFFFAOYSA-N ethyl 4-(2-butylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCCCC1=CC=CC=C1C1C(C(=O)OCC)=C(CCC)NC2=C1C=NN2 KCNDBNBMPRCNIE-UHFFFAOYSA-N 0.000 description 1
OXRWLHSTHUISAF-UHFFFAOYSA-N ethyl 4-(2-chloro-3-cyanophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C#N)=C1Cl OXRWLHSTHUISAF-UHFFFAOYSA-N 0.000 description 1
GQTISLAVJKIHAN-UHFFFAOYSA-N ethyl 4-(2-chloro-3-methylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C)=C1Cl GQTISLAVJKIHAN-UHFFFAOYSA-N 0.000 description 1
CRRGEFZDYVLDIM-UHFFFAOYSA-N ethyl 4-(2-chloro-3-nitrophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC([N+]([O-])=O)=C1Cl CRRGEFZDYVLDIM-UHFFFAOYSA-N 0.000 description 1
GRVWPEAYULCCPB-UHFFFAOYSA-N ethyl 4-(2-chloro-4-fluorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=C(F)C=C1Cl GRVWPEAYULCCPB-UHFFFAOYSA-N 0.000 description 1
LSLMXCGWGJIEGG-UHFFFAOYSA-N ethyl 4-(2-chloro-5-methoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC(OC)=CC=C1Cl LSLMXCGWGJIEGG-UHFFFAOYSA-N 0.000 description 1
PUXJBRMCSFEZAO-UHFFFAOYSA-N ethyl 4-(2-chloro-6-fluorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=C(F)C=CC=C1Cl PUXJBRMCSFEZAO-UHFFFAOYSA-N 0.000 description 1
LNFPXJXAINIRJD-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-1-(3-phenylprop-2-enoyl)-6-propyl-2,3,4,7-tetrahydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound N1C(CCC)=C(C(=O)OCC)C(C=2C(=CC=CC=2)Cl)C(CN2)=C1N2C(=O)C=CC1=CC=CC=C1 LNFPXJXAINIRJD-UHFFFAOYSA-N 0.000 description 1
QJKAUCZHENBDSM-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-1-(3-phenylprop-2-enoyl)-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCCC1=C(C(c2cnn(C(=O)C=Cc3ccccc3)c2N1)c1ccccc1Cl)C(=O)OCC QJKAUCZHENBDSM-UHFFFAOYSA-N 0.000 description 1
ANNFBTAGYNBZKF-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-1-(phenylcarbamoyl)-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2NC(CCC)=C(C(=O)OCC)C(C=3C(=CC=CC=3)Cl)C=2C=NN1C(=O)NC1=CC=CC=C1 ANNFBTAGYNBZKF-UHFFFAOYSA-N 0.000 description 1
YFFXLIRLTCIXMA-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-1-methyl-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2C=NN(C)C=2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl YFFXLIRLTCIXMA-UHFFFAOYSA-N 0.000 description 1
LZIKVRFCNSBIQP-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-2-methyl-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CN(C)N=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl LZIKVRFCNSBIQP-UHFFFAOYSA-N 0.000 description 1
MNNYYINSJSORGE-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-3-methyl-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC(C)=C2C1C1=CC=CC=C1Cl MNNYYINSJSORGE-UHFFFAOYSA-N 0.000 description 1
NSVNAPUKWJIREH-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-3-methyl-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=C(C)NN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl NSVNAPUKWJIREH-UHFFFAOYSA-N 0.000 description 1
ZUBIMKJFIWYEAH-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-(dimethoxymethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(OC)OC)NC2=NNC=C2C1C1=CC=CC=C1Cl ZUBIMKJFIWYEAH-UHFFFAOYSA-N 0.000 description 1
KGPZGQPSUZVGLW-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-ethyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(CC)NC2=NNC=C2C1C1=CC=CC=C1Cl KGPZGQPSUZVGLW-UHFFFAOYSA-N 0.000 description 1
YAGWLPBAMKCWPI-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-methyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC2=NNC=C2C1C1=CC=CC=C1Cl YAGWLPBAMKCWPI-UHFFFAOYSA-N 0.000 description 1
JTTKLKOKJVMIET-UHFFFAOYSA-N ethyl 4-(2-cyanophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1C#N JTTKLKOKJVMIET-UHFFFAOYSA-N 0.000 description 1
SKLLVLCMQPHKNC-UHFFFAOYSA-N ethyl 4-(2-cyclopentyloxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1OC1CCCC1 SKLLVLCMQPHKNC-UHFFFAOYSA-N 0.000 description 1
GDSROHIFQHOTJU-UHFFFAOYSA-N ethyl 4-(2-ethoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1OCC GDSROHIFQHOTJU-UHFFFAOYSA-N 0.000 description 1
DLBJYQDDXNIMHX-UHFFFAOYSA-N ethyl 4-(2-ethylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2C=NNC=2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1CC DLBJYQDDXNIMHX-UHFFFAOYSA-N 0.000 description 1
MJAVVFDOEPMWPY-UHFFFAOYSA-N ethyl 4-(2-fluorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1F MJAVVFDOEPMWPY-UHFFFAOYSA-N 0.000 description 1
ZFAACHUEKYBPFZ-UHFFFAOYSA-N ethyl 4-(2-methoxy-3-methylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C)=C1OC ZFAACHUEKYBPFZ-UHFFFAOYSA-N 0.000 description 1
AMRGGLUXOLKZRB-UHFFFAOYSA-N ethyl 4-(2-methoxynaphthalen-1-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC=C2C(C3C(=C(NC4=NNC=C43)CCC)C(=O)OCC)=C(OC)C=CC2=C1 AMRGGLUXOLKZRB-UHFFFAOYSA-N 0.000 description 1
YFNYHUIYFPLBHM-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=CC=C1OC YFNYHUIYFPLBHM-UHFFFAOYSA-N 0.000 description 1
RDSAQCCRUDALOY-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-6-propan-2-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(C)C)NC2=NNC=C2C1C1=CC=CC=C1OC RDSAQCCRUDALOY-UHFFFAOYSA-N 0.000 description 1
YZWBEQWYDMPGSH-UHFFFAOYSA-N ethyl 4-(2-methylfuran-3-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C=1C=COC=1C YZWBEQWYDMPGSH-UHFFFAOYSA-N 0.000 description 1
JVYQOHRTRNRSFS-UHFFFAOYSA-N ethyl 4-(2-methylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1C JVYQOHRTRNRSFS-UHFFFAOYSA-N 0.000 description 1
NKEIHWGEXOKHJE-UHFFFAOYSA-N ethyl 4-(2-methylsulfanylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNNC2=NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1SC NKEIHWGEXOKHJE-UHFFFAOYSA-N 0.000 description 1
DCMHHIXWHXSGBO-UHFFFAOYSA-N ethyl 4-(2-phenylmethoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1OCC1=CC=CC=C1 DCMHHIXWHXSGBO-UHFFFAOYSA-N 0.000 description 1
ZUHWCNXBJLTSJP-UHFFFAOYSA-N ethyl 4-(2-propoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCCOC1=CC=CC=C1C1C(C(=O)OCC)=C(CCC)NC2=NNC=C21 ZUHWCNXBJLTSJP-UHFFFAOYSA-N 0.000 description 1
KORQNTWKDXUHID-UHFFFAOYSA-N ethyl 4-(2h-chromen-8-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CCOC2=C1C=CC=C2C1C(C(=O)OCC)=C(CCC)NC2=NNC=C21 KORQNTWKDXUHID-UHFFFAOYSA-N 0.000 description 1
QOEAMUMXSHDLGH-UHFFFAOYSA-N ethyl 4-(3-chloro-2-methylphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(Cl)=C1C QOEAMUMXSHDLGH-UHFFFAOYSA-N 0.000 description 1
XAKNQXPFXOJMSR-UHFFFAOYSA-N ethyl 4-(3-chlorophenyl)-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=CC(Cl)=C1 XAKNQXPFXOJMSR-UHFFFAOYSA-N 0.000 description 1
HFDRGLDSPJFOTJ-UHFFFAOYSA-N ethyl 4-(3-chlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(Cl)=C1 HFDRGLDSPJFOTJ-UHFFFAOYSA-N 0.000 description 1
IAUCTMJUJPDNJJ-UHFFFAOYSA-N ethyl 4-(3-cyano-2-methoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC(C#N)=C1OC IAUCTMJUJPDNJJ-UHFFFAOYSA-N 0.000 description 1
QWRZXGGGKAVAQG-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=C(Cl)C=C1 QWRZXGGGKAVAQG-UHFFFAOYSA-N 0.000 description 1
CSYISPZZBNFPPO-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=C(Cl)C=C1 CSYISPZZBNFPPO-UHFFFAOYSA-N 0.000 description 1
JPEADQNGSAKHDS-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=C(OC)C=C1 JPEADQNGSAKHDS-UHFFFAOYSA-N 0.000 description 1
DEYLMJXMBQPROZ-UHFFFAOYSA-N ethyl 4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNNC2=NC(CCC)=C(C(=O)OCC)C1C1=CC(Br)=CC2=C1OCC2 DEYLMJXMBQPROZ-UHFFFAOYSA-N 0.000 description 1
CQCJZDHFOCNYMO-UHFFFAOYSA-N ethyl 4-(5-fluoro-2-methoxyphenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC(F)=CC=C1OC CQCJZDHFOCNYMO-UHFFFAOYSA-N 0.000 description 1
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
BHYVHYPBRYOMGC-UHFFFAOYSA-N ethyl 4-formylbenzoate Chemical compound CCOC(=O)C1=CC=C(C=O)C=C1 BHYVHYPBRYOMGC-UHFFFAOYSA-N 0.000 description 1
BVNAUSOASGRLCZ-UHFFFAOYSA-N ethyl 4-methyl-4-phenyl-6-propyl-1,2-dihydropyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1(C)C1=CC=CC=C1 BVNAUSOASGRLCZ-UHFFFAOYSA-N 0.000 description 1
RXBPWFMQEZCQJT-UHFFFAOYSA-N ethyl 4-naphthalen-1-yl-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=CC=C2C(C3C4=CNN=C4NC(=C3C(=O)OCC)C(F)(F)F)=CC=CC2=C1 RXBPWFMQEZCQJT-UHFFFAOYSA-N 0.000 description 1
IKHLPYNCIVZSAP-UHFFFAOYSA-N ethyl 4-phenyl-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=CC=C1 IKHLPYNCIVZSAP-UHFFFAOYSA-N 0.000 description 1
WGHUTNKKRWHIPZ-UHFFFAOYSA-N ethyl 4-thiophen-2-yl-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=CS1 WGHUTNKKRWHIPZ-UHFFFAOYSA-N 0.000 description 1
XAXDPCXRYAIYQF-UHFFFAOYSA-N ethyl 4-thiophen-3-yl-6-(trifluoromethyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C=1C=CSC=1 XAXDPCXRYAIYQF-UHFFFAOYSA-N 0.000 description 1
XWDWPGBYEQNBIW-UHFFFAOYSA-N ethyl 6-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(F)(F)F)NC2=NNC=C2C1C1=CC=CC=C1C(F)(F)F XWDWPGBYEQNBIW-UHFFFAOYSA-N 0.000 description 1
SJKFBZZXGOWJQW-UHFFFAOYSA-N ethyl 6-benzyl-4-(2-chlorophenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound N1C2=NNC=C2C(C=2C(=CC=CC=2)Cl)C(C(=O)OCC)=C1CC1=CC=CC=C1 SJKFBZZXGOWJQW-UHFFFAOYSA-N 0.000 description 1
FZHULWSGYGPLTH-UHFFFAOYSA-N ethyl 6-butyl-4-(2-chlorophenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCCC)=C(C(=O)OCC)C1C1=CC=CC=C1Cl FZHULWSGYGPLTH-UHFFFAOYSA-N 0.000 description 1
UWIUKYDMYSMXFI-UHFFFAOYSA-N ethyl 6-butyl-4-(2-methoxyphenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCCC)=C(C(=O)OCC)C1C1=CC=CC=C1OC UWIUKYDMYSMXFI-UHFFFAOYSA-N 0.000 description 1
DOSLSYBJTVGYEU-UHFFFAOYSA-N ethyl 6-ethyl-4-(2-methoxyphenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(CC)NC2=NNC=C2C1C1=CC=CC=C1OC DOSLSYBJTVGYEU-UHFFFAOYSA-N 0.000 description 1
RSPPJSYAEVBWKZ-UHFFFAOYSA-N ethyl 6-methyl-4-[2-(trifluoromethyl)phenyl]-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC2=NNC=C2C1C1=CC=CC=C1C(F)(F)F RSPPJSYAEVBWKZ-UHFFFAOYSA-N 0.000 description 1
OKZVUHDKFQSUKH-UHFFFAOYSA-N ethyl 6-propyl-4-(2-propylphenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1=2C=NNC=2NC(CCC)=C(C(=O)OCC)C1C1=CC=CC=C1CCC OKZVUHDKFQSUKH-UHFFFAOYSA-N 0.000 description 1
XUGDPETWCKUWQZ-UHFFFAOYSA-N ethyl 6-propyl-4-(5,6,7,8-tetrahydronaphthalen-1-yl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C1CCCC2=C1C=CC=C2C1C(C(=O)OCC)=C(CCC)NC2=NNC=C21 XUGDPETWCKUWQZ-UHFFFAOYSA-N 0.000 description 1
YELONDRWRGQCMY-UHFFFAOYSA-N ethyl 6-propyl-4-pyridin-4-yl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OCC)C1C1=CC=NC=C1 YELONDRWRGQCMY-UHFFFAOYSA-N 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
230000036737 immune function Effects 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000002434 immunopotentiative effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
230000006362 insulin response pathway Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
ALALKVCEVIMQIG-UHFFFAOYSA-N methyl 1-(methoxymethyl)indole-3-carboxylate Chemical compound C1=CC=C2N(COC)C=C(C(=O)OC)C2=C1 ALALKVCEVIMQIG-UHFFFAOYSA-N 0.000 description 1
GIJIKNIHYNIDSJ-UHFFFAOYSA-N methyl 1-benzofuran-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=CC2=C1 GIJIKNIHYNIDSJ-UHFFFAOYSA-N 0.000 description 1
KRRAZMUPVIGDCU-UHFFFAOYSA-N methyl 1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OC)=CC2=C1 KRRAZMUPVIGDCU-UHFFFAOYSA-N 0.000 description 1
NZTCVGHPDWAALP-UHFFFAOYSA-N methyl 2,2-dimethoxyacetate Chemical compound COC(OC)C(=O)OC NZTCVGHPDWAALP-UHFFFAOYSA-N 0.000 description 1
SMCVPMKCDDNUCQ-UHFFFAOYSA-N methyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OC SMCVPMKCDDNUCQ-UHFFFAOYSA-N 0.000 description 1
BRWROFVPMUPMJQ-UHFFFAOYSA-N methyl 3-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1C BRWROFVPMUPMJQ-UHFFFAOYSA-N 0.000 description 1
SJPCQNABHNCLPB-UHFFFAOYSA-N methyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OC SJPCQNABHNCLPB-UHFFFAOYSA-N 0.000 description 1
OFZJIUVKYKQSSW-UHFFFAOYSA-N methyl 4-(2-chlorophenyl)-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(CCC)=C(C(=O)OC)C1C1=CC=CC=C1Cl OFZJIUVKYKQSSW-UHFFFAOYSA-N 0.000 description 1
QLWUHAQCKDHUNL-UHFFFAOYSA-N methyl 5-bromothiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(Br)S1 QLWUHAQCKDHUNL-UHFFFAOYSA-N 0.000 description 1
SQVGSFPLDUMEDG-UHFFFAOYSA-N methyl 5-chlorothiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(Cl)S1 SQVGSFPLDUMEDG-UHFFFAOYSA-N 0.000 description 1
NEPZGUGQLAOODR-UHFFFAOYSA-N methyl 5-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(C)S1 NEPZGUGQLAOODR-UHFFFAOYSA-N 0.000 description 1
LZJURSMTJHXWIG-UHFFFAOYSA-N methyl 6-(methoxymethyl)-4-(2-methoxyphenyl)-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(COC)=C(C(=O)OC)C1C1=CC=CC=C1OC LZJURSMTJHXWIG-UHFFFAOYSA-N 0.000 description 1
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
ZKHQSQYLKSSYIP-UHFFFAOYSA-N methyl furan-3-carboxylate Chemical compound COC(=O)C=1C=COC=1 ZKHQSQYLKSSYIP-UHFFFAOYSA-N 0.000 description 1
OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
ZTRAEMILTFNZSM-UHFFFAOYSA-N methyl thiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1 ZTRAEMILTFNZSM-UHFFFAOYSA-N 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
229960001238 methylnicotinate Drugs 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
FZBHKLJIFGHUDA-UHFFFAOYSA-N propan-2-yl 4-(2-fluorophenyl)-6-methyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC2=NNC=C2C1C1=CC=CC=C1F FZBHKLJIFGHUDA-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
MSTPNDZQVGSTET-UHFFFAOYSA-M sodium;2-anilino-6-sulfanylidene-1h-1,3,5-triazine-4-thiolate Chemical compound [Na+].N1C(=S)N=C([S-])N=C1NC1=CC=CC=C1 MSTPNDZQVGSTET-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UPGPAVAGECXNSD-UHFFFAOYSA-N tert-butyl 3-(1,4-dihydropyrazolo[3,4-b]pyridin-2-yl)indole-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C=C1N1N=C2NC=CCC2=C1 UPGPAVAGECXNSD-UHFFFAOYSA-N 0.000 description 1
LMBRRFNATMGEIW-UHFFFAOYSA-N tert-butyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)NC=1C=CN(C(=O)OC(C)(C)C)N=1 LMBRRFNATMGEIW-UHFFFAOYSA-N 0.000 description 1
GASCWQBZVFVGIP-UHFFFAOYSA-N tert-butyl 3-[4-(2,1,3-benzoxadiazol-4-yl)-5-cyano-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-6-yl]indole-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C=C1C1=C(C#N)C(C=2C3=NON=C3C=CC=2)C2=CNN=C2N1 GASCWQBZVFVGIP-UHFFFAOYSA-N 0.000 description 1
JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
XZQGHUIUHPIWNZ-UHFFFAOYSA-N tert-butyl 4-(2,1,3-benzoxadiazol-4-yl)-5-cyano-6-propyl-1,4-dihydropyrazolo[3,4-b]pyridine-2-carboxylate Chemical compound C1=CC2=NON=C2C(C2C(C#N)=C(NC3=NN(C=C32)C(=O)OC(C)(C)C)CCC)=C1 XZQGHUIUHPIWNZ-UHFFFAOYSA-N 0.000 description 1
BBUCKWIASGQUEA-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenyl)-5-cyano-6-methyl-1,4-dihydropyrazolo[3,4-b]pyridine-2-carboxylate Chemical compound C12=CN(C(=O)OC(C)(C)C)N=C2NC(C)=C(C#N)C1C1=CC=CC=C1Cl BBUCKWIASGQUEA-UHFFFAOYSA-N 0.000 description 1
PMXJNHYMVMISSC-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenyl)-5-cyano-6-propyl-4,7-dihydropyrazolo[3,4-b]pyridine-1-carboxylate Chemical compound C1=2C=NN(C(=O)OC(C)(C)C)C=2NC(CCC)=C(C#N)C1C1=CC=CC=C1Cl PMXJNHYMVMISSC-UHFFFAOYSA-N 0.000 description 1
QXHVILAEOFNEQC-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenyl)-6-methyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound C12=CNN=C2NC(C)=C(C(=O)OC(C)(C)C)C1C1=CC=CC=C1Cl QXHVILAEOFNEQC-UHFFFAOYSA-N 0.000 description 1
QTUFATHHPQDXHM-UHFFFAOYSA-N tert-butyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pyrazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)NC1=CC=NN1C(=O)OC(C)(C)C QTUFATHHPQDXHM-UHFFFAOYSA-N 0.000 description 1
MIMYLBLILVRISR-UHFFFAOYSA-N tert-butyl [4-(2-chlorophenyl)-5-cyano-6-propyl-2,4-dihydro-1h-pyrazolo[3,4-b]pyridin-3-yl] carbonate Chemical compound C1=2C(OC(=O)OC(C)(C)C)=NNC=2NC(CCC)=C(C#N)C1C1=CC=CC=C1Cl MIMYLBLILVRISR-UHFFFAOYSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
BICXMOFKMVOYAG-UHFFFAOYSA-N trifluoromethyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound FC(F)(F)OC(=O)C1=CC=2C(N=C1)=NNC2 BICXMOFKMVOYAG-UHFFFAOYSA-N 0.000 description 1
UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
AALUTIYNYXEFNT-UHFFFAOYSA-N trimethylsilane hydroiodide Chemical compound C[SiH](C)C.I AALUTIYNYXEFNT-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
229960000604 valproic acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000001262 western blot Methods 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P3/08—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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Diabetes (AREA)
Immunology (AREA)
Hematology (AREA)
Obesity (AREA)
Psychology (AREA)
Psychiatry (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002437215A 2001-02-02 2002-02-01 Composes de dihydropyrazolopyridine et leur utilisation pharmaceutique Abandoned CA2437215A1 (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
JP2001026379		2001-02-02
JP2001-26379		2001-02-02
JP2001081238		2001-03-21
JP2001-81238		2001-03-21
JP2001-304707		2001-09-28
JP2001304707		2001-09-28
PCT/JP2002/000829 WO2002062795A2 (fr)	2001-02-02	2002-02-01	Composes de dihydropyrazolopyridine et leur utilisation pharmaceutique

Publications (1)

Publication Number	Publication Date
CA2437215A1 true CA2437215A1 (fr)	2002-08-15

Family

ID=27345889

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002437215A Abandoned CA2437215A1 (fr)	2001-02-02	2002-02-01	Composes de dihydropyrazolopyridine et leur utilisation pharmaceutique

Country Status (6)

Country	Link
EP (1)	EP1355909A2 (fr)
JP (1)	JP2005501800A (fr)
KR (1)	KR20030076650A (fr)
CN (1)	CN1630656A (fr)
CA (1)	CA2437215A1 (fr)
WO (1)	WO2002062795A2 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20050069977A (ko) *	2002-08-07	2005-07-05	미쯔비시 웰 파마 가부시키가이샤	디히드로피라졸로피리딘 화합물
WO2004037814A1 (fr) *	2002-10-25	2004-05-06	Vertex Pharmaceuticals Incorporated	Compositions indazolinones utiles en tant qu'inhibiteurs des kinases
PE20050521A1 (es)	2003-02-27	2005-09-11	Uriach Y Compania S A J	Derivados de pirazolopiridina
ES2214150B1 (es) *	2003-02-27	2005-12-01	J. URIACH & CIA S.A.	"nuevos derivados de pirazolopiridinas".
ES2335284T3 (es) *	2003-09-03	2010-03-24	Glaxo Group Limited	Nuevo procedimiento para preparar derivados de pleuromutilina.
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2002
- 2002-02-01 JP JP2002563148A patent/JP2005501800A/ja not_active Withdrawn
- 2002-02-01 CN CNA028045041A patent/CN1630656A/zh active Pending
- 2002-02-01 WO PCT/JP2002/000829 patent/WO2002062795A2/fr not_active Application Discontinuation
- 2002-02-01 CA CA002437215A patent/CA2437215A1/fr not_active Abandoned
- 2002-02-01 EP EP02710458A patent/EP1355909A2/fr not_active Withdrawn
- 2002-02-01 KR KR10-2003-7010230A patent/KR20030076650A/ko not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1630656A (zh)	2005-06-22
WO2002062795A3 (fr)	2003-05-30
WO2002062795A2 (fr)	2002-08-15
WO2002062795A9 (fr)	2002-10-10
EP1355909A2 (fr)	2003-10-29
JP2005501800A (ja)	2005-01-20
KR20030076650A (ko)	2003-09-26

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