TW201319067A - 三唑并吡啶化合物 - Google Patents

Info

Publication number

TW201319067A

TW201319067A TW101133879A TW101133879A TW201319067A TW 201319067 A TW201319067 A TW 201319067A TW 101133879 A TW101133879 A TW 101133879A TW 101133879 A TW101133879 A TW 101133879A TW 201319067 A TW201319067 A TW 201319067A

Authority

TW

Taiwan

Prior art keywords

methyl

triazolo

pyrazol

pyridin

ylthio

Prior art date

2011-09-15

Links

• Espacenet
• Global Dossier
• Discuss

• 150000008523 triazolopyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 407
• 150000003839 salts Chemical class 0.000 claims abstract description 92
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 59
• 201000010099 disease Diseases 0.000 claims abstract description 54
• 238000011282 treatment Methods 0.000 claims abstract description 50
• 239000003814 drug Substances 0.000 claims abstract description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 19
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 19
• 230000001404 mediated effect Effects 0.000 claims abstract description 19
• 238000004519 manufacturing process Methods 0.000 claims abstract description 12
• -1 substituted Chemical class 0.000 claims description 260
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 124
• 125000000623 heterocyclic group Chemical group 0.000 claims description 118
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 84
• 125000001424 substituent group Chemical group 0.000 claims description 71
• 125000004122 cyclic group Chemical group 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 58
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
• 229920006395 saturated elastomer Polymers 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 42
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000005842 heteroatom Chemical group 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 21
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 20
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 19
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
• 230000004968 inflammatory condition Effects 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 13
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 13
• 230000002062 proliferating effect Effects 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 238000006467 substitution reaction Methods 0.000 claims description 11
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 claims description 9
• 241000156724 Antirhea Species 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 6
• OKTRGNFHPHPORR-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-piperazin-1-ylquinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCNCC3)=NN=C2C=C1 OKTRGNFHPHPORR-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• GGSJKYXMTHZWFU-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCOCC3)=NN=C2C(F)=C1 GGSJKYXMTHZWFU-UHFFFAOYSA-N 0.000 claims description 5
• TWVWCIKZBQUKNQ-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCN(CC(F)(F)F)CC3)=NN=C2C=C1 TWVWCIKZBQUKNQ-UHFFFAOYSA-N 0.000 claims description 5
• IMTTXYPMOVLULF-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-n-(1-methylpiperidin-4-yl)quinolin-3-amine Chemical compound C1CN(C)CCC1NC1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 IMTTXYPMOVLULF-UHFFFAOYSA-N 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 208000035475 disorder Diseases 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• ZBAAKUHERHHMAH-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-amine Chemical compound C1CN(C)CCC1NC1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 ZBAAKUHERHHMAH-UHFFFAOYSA-N 0.000 claims description 5
• JZIKZJCBYAYGEA-UHFFFAOYSA-N 2-[4-[3-(3-morpholin-4-ylquinolin-6-yl)sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCOCC3)=NN=C2C=C1 JZIKZJCBYAYGEA-UHFFFAOYSA-N 0.000 claims description 4
• QXMNTGNVLMNHEO-UHFFFAOYSA-N 2-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-8-oxa-2-azaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(CC3)CCOCC4)=NN=C2C=C1 QXMNTGNVLMNHEO-UHFFFAOYSA-N 0.000 claims description 4
• WHWAOQDLIBFTNE-UHFFFAOYSA-N 2-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-8-oxa-2-azaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(CC3)CCOCC4)=NN=C2C(F)=C1 WHWAOQDLIBFTNE-UHFFFAOYSA-N 0.000 claims description 4
• KSZWVRDXHXOEKN-UHFFFAOYSA-N 2-methyl-4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1COC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 KSZWVRDXHXOEKN-UHFFFAOYSA-N 0.000 claims description 4
• MAEFTXPFQHILHT-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1CN(C)CCN1CC1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 MAEFTXPFQHILHT-UHFFFAOYSA-N 0.000 claims description 4
• NLRBOMANTTVJTI-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-2-methylmorpholine Chemical compound C1COC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 NLRBOMANTTVJTI-UHFFFAOYSA-N 0.000 claims description 4
• KUYMCRLOLWIWOI-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-3-methylmorpholine Chemical compound CC1COCCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 KUYMCRLOLWIWOI-UHFFFAOYSA-N 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
• OJMCEDPZTBVMKX-IYBDPMFKSA-N 3-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 OJMCEDPZTBVMKX-IYBDPMFKSA-N 0.000 claims description 3
• OCUFWFWPMTVLOB-CALCHBBNSA-N 3-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 OCUFWFWPMTVLOB-CALCHBBNSA-N 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
• KCSVVCQNVWNDNF-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCNCCC3)=NN=C2C=C1 KCSVVCQNVWNDNF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 150000004032 porphyrins Chemical class 0.000 claims description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
• PSNYRIOHVUOFPW-FLOSOGMCSA-N (ne)-n-[1-[3-[3-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylidene]hydroxylamine Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C(\C)=N\O)=C2)C2=C1 PSNYRIOHVUOFPW-FLOSOGMCSA-N 0.000 claims 1
• OHQMOXPQJBEGOZ-UHFFFAOYSA-N 3-(4,4-difluoropiperidin-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(F)(F)CC3)=NN=C2C=C1 OHQMOXPQJBEGOZ-UHFFFAOYSA-N 0.000 claims 1
• IABXEOYJCXGIMD-UHFFFAOYSA-N 3-(4,4-difluoropiperidin-1-yl)-6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(F)(F)CC3)=NN=C2C(F)=C1 IABXEOYJCXGIMD-UHFFFAOYSA-N 0.000 claims 1
• PYICCQVWUOKFSY-UHFFFAOYSA-N 4-[6-[[6-(1h-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1COCCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CNN=C2)=C2)C2=C1 PYICCQVWUOKFSY-UHFFFAOYSA-N 0.000 claims 1
• GNCNEAGBGRHTAT-UHFFFAOYSA-N 6-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-2-oxa-6-azaspiro[3.3]heptane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(COC4)C3)=NN=C2C=C1 GNCNEAGBGRHTAT-UHFFFAOYSA-N 0.000 claims 1
• QTDCAXYCFZXWPG-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-piperidin-1-ylpiperidin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(CC3)N3CCCCC3)=NN=C2C=C1 QTDCAXYCFZXWPG-UHFFFAOYSA-N 0.000 claims 1
• ZRUDAHOWOHKQAO-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-methoxypiperidin-1-yl)quinoline Chemical compound C1CC(OC)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 ZRUDAHOWOHKQAO-UHFFFAOYSA-N 0.000 claims 1
• XELQJFZPZDIESZ-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-methylpiperazin-1-yl)quinoline Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 XELQJFZPZDIESZ-UHFFFAOYSA-N 0.000 claims 1
• IFBRUUOIKYNFQU-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(CC3)N3CCCC3)=NN=C2C(F)=C1 IFBRUUOIKYNFQU-UHFFFAOYSA-N 0.000 claims 1
• PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 claims 1
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 330
• 238000002360 preparation method Methods 0.000 abstract description 16
• 230000008569 process Effects 0.000 abstract description 9
• 241001465754 Metazoa Species 0.000 abstract description 5
• 239000000543 intermediate Substances 0.000 description 206
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 144
• 239000000203 mixture Substances 0.000 description 125
• 235000019439 ethyl acetate Nutrition 0.000 description 90
• 238000006243 chemical reaction Methods 0.000 description 78
• 239000000243 solution Substances 0.000 description 77
• 230000000694 effects Effects 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 50
• 239000002904 solvent Substances 0.000 description 44
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
• 206010028980 Neoplasm Diseases 0.000 description 37
• 230000002829 reductive effect Effects 0.000 description 36
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 35
• 239000003112 inhibitor Substances 0.000 description 35
• 239000011734 sodium Substances 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 31
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
• 239000012453 solvate Substances 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 22
• 239000012074 organic phase Substances 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 150000001721 carbon Chemical group 0.000 description 20
• 229940124597 therapeutic agent Drugs 0.000 description 20
• 239000002585 base Substances 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• 201000011510 cancer Diseases 0.000 description 18
• 239000012043 crude product Substances 0.000 description 18
• 230000002401 inhibitory effect Effects 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• FXHRAKUEZPSMLJ-UHFFFAOYSA-N 1-methyl-1,4-diazepane Chemical compound CN1CCCNCC1 FXHRAKUEZPSMLJ-UHFFFAOYSA-N 0.000 description 17
• 229940079593 drug Drugs 0.000 description 17
• 108090000623 proteins and genes Proteins 0.000 description 17
• 108091000080 Phosphotransferase Proteins 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 16
• 102000020233 phosphotransferase Human genes 0.000 description 16
• 101001098806 Dictyostelium discoideum cGMP-specific 3',5'-cGMP phosphodiesterase 3 Proteins 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 229910052786 argon Inorganic materials 0.000 description 15
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