CA2804845A1 - Substituted imidazo[1,2-a]pyrimidines and -pyridines - Google Patents
Substituted imidazo[1,2-a]pyrimidines and -pyridines Download PDFInfo
- Publication number
- CA2804845A1 CA2804845A1 CA2804845A CA2804845A CA2804845A1 CA 2804845 A1 CA2804845 A1 CA 2804845A1 CA 2804845 A CA2804845 A CA 2804845A CA 2804845 A CA2804845 A CA 2804845A CA 2804845 A1 CA2804845 A1 CA 2804845A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- imidazo
- pyridin
- alkyl
- cyclobutylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 368
- 238000000034 method Methods 0.000 claims abstract description 265
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 264
- 239000001257 hydrogen Substances 0.000 claims description 253
- 229910052736 halogen Inorganic materials 0.000 claims description 206
- 150000002367 halogens Chemical group 0.000 claims description 206
- -1 3-7C-cycloalkyl Chemical group 0.000 claims description 187
- 235000013350 formula milk Nutrition 0.000 claims description 154
- 239000000203 mixture Substances 0.000 claims description 149
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 139
- 206010028980 Neoplasm Diseases 0.000 claims description 113
- 150000003839 salts Chemical class 0.000 claims description 107
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000001072 heteroaryl group Chemical group 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 71
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 150000001204 N-oxides Chemical class 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
- 201000010099 disease Diseases 0.000 claims description 45
- 125000006239 protecting group Chemical group 0.000 claims description 45
- 230000009826 neoplastic cell growth Effects 0.000 claims description 39
- 230000003211 malignant effect Effects 0.000 claims description 35
- 229920006395 saturated elastomer Polymers 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 26
- 239000002246 antineoplastic agent Substances 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 230000006882 induction of apoptosis Effects 0.000 claims description 17
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 14
- 230000003463 hyperproliferative effect Effects 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- ZLUZMRGENYSWJR-NTUHNPAUSA-N (e)-3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]prop-2-enamide Chemical compound N12C=C(/C=C/C(=O)N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 ZLUZMRGENYSWJR-NTUHNPAUSA-N 0.000 claims 1
- FJZWNBISHWDALI-UHFFFAOYSA-N 1-[2-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyrimidin-7-yl]oxyethyl]pyrrolidin-2-one Chemical compound C=1C=C(C2=C(N3C=CC(OCCN4C(CCC4)=O)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FJZWNBISHWDALI-UHFFFAOYSA-N 0.000 claims 1
- VDKHXAAHUVGQOQ-UHFFFAOYSA-N 1-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]ethanol Chemical compound N12C=C(C(O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 VDKHXAAHUVGQOQ-UHFFFAOYSA-N 0.000 claims 1
- UPJRTEWYTRCMGI-UHFFFAOYSA-N 1-[4-(3,6-diphenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=C(C=NC3=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 UPJRTEWYTRCMGI-UHFFFAOYSA-N 0.000 claims 1
- SSMHOKCXASOSDR-UHFFFAOYSA-N 1-[4-(3-phenyl-7-propan-2-yloxyimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OC(C)C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 SSMHOKCXASOSDR-UHFFFAOYSA-N 0.000 claims 1
- PTBIXVGGTHAJMK-UHFFFAOYSA-N 1-[4-(3-phenyl-7-propoxyimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 PTBIXVGGTHAJMK-UHFFFAOYSA-N 0.000 claims 1
- ABXVUGZVUCYNCO-UHFFFAOYSA-N 1-[4-(3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ABXVUGZVUCYNCO-UHFFFAOYSA-N 0.000 claims 1
- LMBQMEOEJDKMKM-UHFFFAOYSA-N 1-[4-(3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 LMBQMEOEJDKMKM-UHFFFAOYSA-N 0.000 claims 1
- JVOLVCNRQRHUHA-UHFFFAOYSA-N 1-[4-(6-ethyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(CC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 JVOLVCNRQRHUHA-UHFFFAOYSA-N 0.000 claims 1
- LGWBCYYZSZQYET-UHFFFAOYSA-N 1-[4-(6-ethyl-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N12C=C(CC)C=NC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 LGWBCYYZSZQYET-UHFFFAOYSA-N 0.000 claims 1
- FBANRZKZWPNHSN-UHFFFAOYSA-N 1-[4-(7-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(Br)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 FBANRZKZWPNHSN-UHFFFAOYSA-N 0.000 claims 1
- VYFQASOWIMQBFB-UHFFFAOYSA-N 1-[4-(7-cyclohexyloxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(OC4CCCCC4)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VYFQASOWIMQBFB-UHFFFAOYSA-N 0.000 claims 1
- MYNRPWMBDKXPIV-UHFFFAOYSA-N 1-[4-(7-ethoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(OCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MYNRPWMBDKXPIV-UHFFFAOYSA-N 0.000 claims 1
- INAUCNDZLSOGJO-UHFFFAOYSA-N 1-[4-(7-ethoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 INAUCNDZLSOGJO-UHFFFAOYSA-N 0.000 claims 1
- LFEWFIMPGRKMKG-UHFFFAOYSA-N 1-[4-(7-ethyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(CC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 LFEWFIMPGRKMKG-UHFFFAOYSA-N 0.000 claims 1
- MOGYPQBWQDORPP-UHFFFAOYSA-N 1-[4-(7-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2C=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 MOGYPQBWQDORPP-UHFFFAOYSA-N 0.000 claims 1
- CBOPZRDROLVYRN-UHFFFAOYSA-N 1-[4-(7-methoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 CBOPZRDROLVYRN-UHFFFAOYSA-N 0.000 claims 1
- ZYLHBIQWOJSANG-UHFFFAOYSA-N 1-[4-(7-phenoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(OC=4C=CC=CC=4)=NC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZYLHBIQWOJSANG-UHFFFAOYSA-N 0.000 claims 1
- XGDHYAZSEQCNOK-UHFFFAOYSA-N 1-[4-(8-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(Br)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XGDHYAZSEQCNOK-UHFFFAOYSA-N 0.000 claims 1
- HPQFDZVVQQRZHS-UHFFFAOYSA-N 1-[4-[3-phenyl-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C2=CNN=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 HPQFDZVVQQRZHS-UHFFFAOYSA-N 0.000 claims 1
- DPQDHVZPZYLUNI-UHFFFAOYSA-N 1-[4-[3-phenyl-8-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2NN=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 DPQDHVZPZYLUNI-UHFFFAOYSA-N 0.000 claims 1
- XBISPBWLIODRFQ-UHFFFAOYSA-N 1-[4-[6-(1h-imidazol-5-yl)-8-methoxy-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C=3NC=NC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 XBISPBWLIODRFQ-UHFFFAOYSA-N 0.000 claims 1
- XMWNNGHXZDVUJV-UHFFFAOYSA-N 1-[4-[7-(2-aminoethoxy)-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCN)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 XMWNNGHXZDVUJV-UHFFFAOYSA-N 0.000 claims 1
- YNOSHXGRYKDBMO-UHFFFAOYSA-N 1-[4-[7-(2-methoxyethoxy)-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OCCOC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 YNOSHXGRYKDBMO-UHFFFAOYSA-N 0.000 claims 1
- GTFSRNKPWDHODK-UHFFFAOYSA-N 1-[4-[7-(4-fluorophenyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C=2C=CC(F)=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GTFSRNKPWDHODK-UHFFFAOYSA-N 0.000 claims 1
- SYMPTBRPUWCVTC-UHFFFAOYSA-N 1-[4-[7-[(2-methoxypyridin-4-yl)methoxy]-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NC(OC)=CC(COC2=NC3=NC(=C(N3C=C2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C2(N)CCC2)=C1 SYMPTBRPUWCVTC-UHFFFAOYSA-N 0.000 claims 1
- GHEHSCYHOBFXLO-UHFFFAOYSA-N 1-[4-[7-[(6-methoxypyridin-3-yl)methoxy]-3-phenylimidazo[1,2-a]pyrimidin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C1=NC(OC)=CC=C1COC1=NC2=NC(C=3C=CC(=CC=3)C3(N)CCC3)=C(C=3C=CC=CC=3)N2C=C1 GHEHSCYHOBFXLO-UHFFFAOYSA-N 0.000 claims 1
- XQIJCRMHBBDRAW-UHFFFAOYSA-N 1-[4-[8-(3-fluorophenyl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C=2C=C(F)C=CC=2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XQIJCRMHBBDRAW-UHFFFAOYSA-N 0.000 claims 1
- FPPAQOQEDKFECY-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-6-(1h-pyrazol-5-yl)imidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC(C=3NN=CC=3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 FPPAQOQEDKFECY-UHFFFAOYSA-N 0.000 claims 1
- XMALRWXFIWIGCQ-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-amine;n-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]acetamide Chemical compound N12C=C(N)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1.N12C=C(NC(=O)C)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 XMALRWXFIWIGCQ-UHFFFAOYSA-N 0.000 claims 1
- XBQDOZCBHDDKPA-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-ol Chemical compound C=1C=C(C2=C(N3C=C(O)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 XBQDOZCBHDDKPA-UHFFFAOYSA-N 0.000 claims 1
- CZSCPFJAHJJOSC-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-amine;n-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]acetamide Chemical compound N1=C2C=C(N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1.N1=C2C=C(NC(=O)C)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 CZSCPFJAHJJOSC-UHFFFAOYSA-N 0.000 claims 1
- GLKFXRCYMJOMSD-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 GLKFXRCYMJOMSD-UHFFFAOYSA-N 0.000 claims 1
- KVAOMOBHQYDUCN-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 KVAOMOBHQYDUCN-UHFFFAOYSA-N 0.000 claims 1
- IWPHXFMQLJNWQA-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carbonitrile Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IWPHXFMQLJNWQA-UHFFFAOYSA-N 0.000 claims 1
- JBTAEEKPONTXSL-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)N)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 JBTAEEKPONTXSL-UHFFFAOYSA-N 0.000 claims 1
- ZATBMOVJDNGDAP-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile Chemical compound C=1C=C(C2=C(N3C=CC=C(C3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZATBMOVJDNGDAP-UHFFFAOYSA-N 0.000 claims 1
- SNTBNZPFJQCQAZ-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-8-carboxamide Chemical compound N1=C2C(C(=O)N)=CC=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 SNTBNZPFJQCQAZ-UHFFFAOYSA-N 0.000 claims 1
- WURJZSZUOFJYBH-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-7-methoxy-3-phenylimidazo[1,2-a]pyridine-8-carbonitrile Chemical compound N1=C2C(C#N)=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 WURJZSZUOFJYBH-UHFFFAOYSA-N 0.000 claims 1
- MGFSZAHJUZQYSI-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-n-methyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NC)C=CC2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 MGFSZAHJUZQYSI-UHFFFAOYSA-N 0.000 claims 1
- HLHRBSJZAIRKFE-NSPIFIKESA-N COC(\C=C\C=1C=CC=2N(C1)C(=C(N2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2)=O.ClC=2C=CC=1N(C2)C(=C(N1)C1=CC=C(C=C1)C1(CCC1)N)C1=CC=CC=C1 Chemical compound COC(\C=C\C=1C=CC=2N(C1)C(=C(N2)C2=CC=C(C=C2)C2(CCC2)N)C2=CC=CC=C2)=O.ClC=2C=CC=1N(C2)C(=C(N1)C1=CC=C(C=C1)C1(CCC1)N)C1=CC=CC=C1 HLHRBSJZAIRKFE-NSPIFIKESA-N 0.000 claims 1
- WBZUWSGBNWQZOF-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]methanol Chemical compound C=1C=C(C2=C(N3C=C(CO)C=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 WBZUWSGBNWQZOF-UHFFFAOYSA-N 0.000 claims 1
- YRBLOFAVEJSWNY-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-7-yl]methanol Chemical compound C=1C=C(C2=C(N3C=CC(CO)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 YRBLOFAVEJSWNY-UHFFFAOYSA-N 0.000 claims 1
- IYTYBBKZINCQJF-UHFFFAOYSA-N [2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-8-yl]methanol Chemical compound C=1C=C(C2=C(N3C=CC=C(CO)C3=N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 IYTYBBKZINCQJF-UHFFFAOYSA-N 0.000 claims 1
- XJZYLKQYZWOOKZ-UHFFFAOYSA-N ethyl 2-[4-(1-aminocyclobutyl)phenyl]-8-bromo-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OCC)C=C(Br)C2=NC(C=2C=CC(=CC=2)C2(N)CCC2)=C1C1=CC=CC=C1 XJZYLKQYZWOOKZ-UHFFFAOYSA-N 0.000 claims 1
- 108091008611 Protein Kinase B Proteins 0.000 abstract description 34
- 230000037361 pathway Effects 0.000 abstract description 26
- 239000003814 drug Substances 0.000 abstract description 10
- 239000003112 inhibitor Substances 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 274
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 221
- 239000000543 intermediate Substances 0.000 description 191
- 150000002431 hydrogen Chemical class 0.000 description 188
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 180
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 134
- 239000000243 solution Substances 0.000 description 117
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- FKBHRUQOROFRGD-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2[C]3C=CC=CC3=NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC FKBHRUQOROFRGD-IELIFDKJSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229960001771 vorozole Drugs 0.000 description 1
- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 229940053867 xeloda Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10169205 | 2010-07-12 | ||
| EP10169205.1 | 2010-07-12 | ||
| US39277910P | 2010-10-13 | 2010-10-13 | |
| US61/392,779 | 2010-10-13 | ||
| PCT/EP2011/061508 WO2012007345A2 (en) | 2010-07-12 | 2011-07-07 | Substituted imidazo[1,2-a]pyrimidines and -pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2804845A1 true CA2804845A1 (en) | 2012-01-19 |
Family
ID=44532777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2804845A Abandoned CA2804845A1 (en) | 2010-07-12 | 2011-07-07 | Substituted imidazo[1,2-a]pyrimidines and -pyridines |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8975265B2 (enExample) |
| EP (1) | EP2593451B1 (enExample) |
| JP (1) | JP5830094B2 (enExample) |
| CN (1) | CN103097384B (enExample) |
| AR (1) | AR090005A1 (enExample) |
| CA (1) | CA2804845A1 (enExample) |
| ES (1) | ES2552841T3 (enExample) |
| TW (1) | TW201206933A (enExample) |
| UY (1) | UY33503A (enExample) |
| WO (1) | WO2012007345A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11524968B2 (en) | 2017-10-18 | 2022-12-13 | Hk Inno.N Corporation | Heterocyclic compound as a protein kinase inhibitor |
| US12180185B2 (en) | 2018-11-15 | 2024-12-31 | Hk Inno.N Corporation | Compound as protein kinase inhibitor, and pharmaceutical composition comprising thereof |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012137870A1 (ja) * | 2011-04-06 | 2012-10-11 | 大鵬薬品工業株式会社 | 新規イミダゾオキサジン化合物又はその塩 |
| PL2694510T3 (pl) * | 2011-04-07 | 2016-03-31 | Bayer Ip Gmbh | Imidazopirydazyny jako inhibitory kinazy Akt |
| EP2802586B1 (en) * | 2012-01-10 | 2016-05-25 | Bayer Intellectual Property GmbH | Substituted imidazopyrazines as akt kinase inhibitors |
| EP2802588B1 (en) * | 2012-01-10 | 2016-05-25 | Bayer Intellectual Property GmbH | Substituted pyrazolopyrimidines as akt kinase inhibitors |
| ES2689429T3 (es) * | 2012-07-13 | 2018-11-14 | Ucb Biopharma Sprl | Derivados de imidazopiridina como moduladores de actividad de TNF |
| PE20161573A1 (es) | 2014-02-13 | 2017-01-19 | Incyte Corp | Ciclopropilamina como inhibidor de la lsd1 |
| TWI664164B (zh) | 2014-02-13 | 2019-07-01 | 美商英塞特控股公司 | 作為ｌｓｄ１抑制劑之環丙胺 |
| WO2015123408A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| AU2015240465B2 (en) | 2014-04-04 | 2020-02-27 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9695168B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| WO2016136928A1 (ja) | 2015-02-27 | 2016-09-01 | 大鵬薬品工業株式会社 | イミダゾオキサジンの結晶、当該結晶を含む医薬組成物、及び当該結晶の製造方法 |
| MY191796A (en) | 2015-04-03 | 2022-07-15 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
| CN106188063A (zh) * | 2015-05-08 | 2016-12-07 | 中国科学院上海药物研究所 | 用作Lp-PLA2抑制剂的双环类化合物、其制备方法及医药用途 |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| US11883404B2 (en) | 2016-03-04 | 2024-01-30 | Taiho Pharmaceuticals Co., Ltd. | Preparation and composition for treatment of malignant tumors |
| PE20190377A1 (es) | 2016-04-22 | 2019-03-08 | Incyte Corp | Formulaciones de un inhibidor de lsd 1 |
| US11352328B2 (en) | 2016-07-12 | 2022-06-07 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus |
| GB201811695D0 (en) * | 2018-07-17 | 2018-08-29 | Salvensis | Compounds for use in the treatment of fascioliasis |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| CN109734713B (zh) * | 2019-03-07 | 2021-06-04 | 东华理工大学 | 一种3-亚胺基咪唑并[1,2-a]吡啶化合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007015578A (es) * | 2005-06-10 | 2008-03-06 | Merck & Co Inc | Inhibidores de la actividad akt. |
| AR064010A1 (es) * | 2006-12-06 | 2009-03-04 | Merck & Co Inc | Inhibidores de la actividad de la akt |
| PA8793301A1 (es) | 2007-08-14 | 2009-04-23 | Bayer Schering Pharma Ag | Imidazoles bicíclicos fusionados |
| CN102015686B (zh) | 2008-03-21 | 2014-07-02 | 诺华股份有限公司 | 杂环化合物及其用途 |
| AU2009255358A1 (en) * | 2008-06-03 | 2009-12-10 | Msd K.K. | Inhibitors of Akt activity |
| AU2010208480A1 (en) | 2009-02-02 | 2011-07-28 | Msd K.K. | Inhibitors of Akt activity |
| WO2010104705A1 (en) | 2009-03-12 | 2010-09-16 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| WO2010114780A1 (en) | 2009-04-01 | 2010-10-07 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| US8546376B2 (en) | 2009-09-18 | 2013-10-01 | Almac Discovery Limited | Pharmaceutical compounds |
| GB0919380D0 (en) | 2009-11-04 | 2009-12-23 | Almac Discovery Ltd | Pharmaceutical compouds |
-
2011
- 2011-07-07 CA CA2804845A patent/CA2804845A1/en not_active Abandoned
- 2011-07-07 WO PCT/EP2011/061508 patent/WO2012007345A2/en not_active Ceased
- 2011-07-07 CN CN201180043391.XA patent/CN103097384B/zh not_active Expired - Fee Related
- 2011-07-07 US US13/808,430 patent/US8975265B2/en not_active Expired - Fee Related
- 2011-07-07 JP JP2013519035A patent/JP5830094B2/ja not_active Expired - Fee Related
- 2011-07-07 ES ES11730003.8T patent/ES2552841T3/es active Active
- 2011-07-07 EP EP11730003.8A patent/EP2593451B1/en active Active
- 2011-07-11 UY UY0001033503A patent/UY33503A/es not_active Application Discontinuation
- 2011-07-12 TW TW100124649A patent/TW201206933A/zh unknown
- 2011-07-12 AR ARP110102496A patent/AR090005A1/es unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11524968B2 (en) | 2017-10-18 | 2022-12-13 | Hk Inno.N Corporation | Heterocyclic compound as a protein kinase inhibitor |
| US12180185B2 (en) | 2018-11-15 | 2024-12-31 | Hk Inno.N Corporation | Compound as protein kinase inhibitor, and pharmaceutical composition comprising thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103097384A (zh) | 2013-05-08 |
| JP2013531684A (ja) | 2013-08-08 |
| CN103097384B (zh) | 2017-02-15 |
| US8975265B2 (en) | 2015-03-10 |
| JP5830094B2 (ja) | 2015-12-09 |
| EP2593451A2 (en) | 2013-05-22 |
| TW201206933A (en) | 2012-02-16 |
| AR090005A1 (es) | 2014-10-15 |
| WO2012007345A2 (en) | 2012-01-19 |
| EP2593451B1 (en) | 2015-08-19 |
| UY33503A (es) | 2012-02-29 |
| ES2552841T3 (es) | 2015-12-02 |
| WO2012007345A3 (en) | 2012-04-12 |
| US20130190332A1 (en) | 2013-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160704 |
|
| FZDE | Dead |
Effective date: 20190910 |