JP2008511618A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008511618A5 JP2008511618A5 JP2007529714A JP2007529714A JP2008511618A5 JP 2008511618 A5 JP2008511618 A5 JP 2008511618A5 JP 2007529714 A JP2007529714 A JP 2007529714A JP 2007529714 A JP2007529714 A JP 2007529714A JP 2008511618 A5 JP2008511618 A5 JP 2008511618A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyridine hydrochloride
- tetrahydroisoquinolin
- dimethyl
- benzyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 21
- -1 methoxy, ethoxy, hydroxy, cyclopropyl Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- DTTRXKDZDKKEIO-UHFFFAOYSA-N 2-(3-benzyl-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC=1NC2=CC=NC(N3CC4=CC=CC=C4CC3)=C2C=1CC1=CC=CC=C1 DTTRXKDZDKKEIO-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 2
- MJRMTVJPUKCMGP-UHFFFAOYSA-N 2-(1,2,3-trimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(C)C2=CC=N1 MJRMTVJPUKCMGP-UHFFFAOYSA-N 0.000 claims 2
- VUEXVEYRULCKDR-UHFFFAOYSA-N 2-(1,3-dibenzyl-2-methylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC=2C=CC=CC=2)C(C)=C1CC1=CC=CC=C1 VUEXVEYRULCKDR-UHFFFAOYSA-N 0.000 claims 2
- FNKNNAYPNBVIHP-UHFFFAOYSA-N 2-(1-ethyl-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CC)C2=CC=N1 FNKNNAYPNBVIHP-UHFFFAOYSA-N 0.000 claims 2
- MOBFKMKSMVCGIL-UHFFFAOYSA-N 2-(2,3-dimethyl-1h-pyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1C1=C(C(=C(C)N2)C)C2=CC=N1 MOBFKMKSMVCGIL-UHFFFAOYSA-N 0.000 claims 2
- AAHYNRGBVRQBQJ-UHFFFAOYSA-N 2-(2,3-dimethyl-1h-pyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C(C(=C(C)N2)C)C2=CC=N1 AAHYNRGBVRQBQJ-UHFFFAOYSA-N 0.000 claims 2
- OEOMIDTXZSSTSD-UHFFFAOYSA-N 2-(3-benzyl-1,2-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(C)C(C)=C1CC1=CC=CC=C1 OEOMIDTXZSSTSD-UHFFFAOYSA-N 0.000 claims 2
- YVYRCUVPCHNUFB-UHFFFAOYSA-N 2-(3-benzyl-1-cyclopropyl-2-methylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(C2CC2)C(C)=C1CC1=CC=CC=C1 YVYRCUVPCHNUFB-UHFFFAOYSA-N 0.000 claims 2
- SUZWTGHMJHSJBH-UHFFFAOYSA-N 2-(3-benzyl-1-ethyl-2-methylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC)C(C)=C1CC1=CC=CC=C1 SUZWTGHMJHSJBH-UHFFFAOYSA-N 0.000 claims 2
- ONOWUWTYEPDOEH-UHFFFAOYSA-N 2-(3-benzyl-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;sodium Chemical compound [Na].CC=1NC2=CC=NC(N3CC4=CC=CC=C4CC3)=C2C=1CC1=CC=CC=C1 ONOWUWTYEPDOEH-UHFFFAOYSA-N 0.000 claims 2
- SCJSSLOKGQNGGO-UHFFFAOYSA-N 2-[1-(2-methoxyethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCOC)C2=CC=N1 SCJSSLOKGQNGGO-UHFFFAOYSA-N 0.000 claims 2
- XRHHCXTUWCAYGB-UHFFFAOYSA-N 2-[3-benzyl-1-(1,3-dioxolan-2-ylmethyl)-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC2OCCO2)C(C)=C1CC1=CC=CC=C1 XRHHCXTUWCAYGB-UHFFFAOYSA-N 0.000 claims 2
- GIGDJMYLGIFAMI-UHFFFAOYSA-N 2-[3-benzyl-1-(2-methoxyethyl)-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CCOC)C(C)=C1CC1=CC=CC=C1 GIGDJMYLGIFAMI-UHFFFAOYSA-N 0.000 claims 2
- KQXZEOVZQMUYFG-UHFFFAOYSA-N 2-[4-(3,4-dihydro-1h-isoquinolin-2-yl)-2,3-dimethylpyrrolo[3,2-c]pyridin-1-yl]ethanol;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCO)C2=CC=N1 KQXZEOVZQMUYFG-UHFFFAOYSA-N 0.000 claims 2
- ACARDXIEVWECPE-UHFFFAOYSA-N 3-benzyl-n-[(4-fluorophenyl)methyl]-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C=12C(CC=3C=CC=CC=3)=C(C)NC2=CC=NC=1NCC1=CC=C(F)C=C1 ACARDXIEVWECPE-UHFFFAOYSA-N 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- FTOKAERMHAZEBC-UHFFFAOYSA-N 1-(1,3-dioxolan-2-ylmethyl)-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC3OCCO3)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 FTOKAERMHAZEBC-UHFFFAOYSA-N 0.000 claims 1
- GIYBOSFIQTZHFE-UHFFFAOYSA-N 1-(cyclopropylmethyl)-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC3CC3)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 GIYBOSFIQTZHFE-UHFFFAOYSA-N 0.000 claims 1
- MPHMNJXBNQRNFZ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC=3C(=CC=CC=3)F)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 MPHMNJXBNQRNFZ-UHFFFAOYSA-N 0.000 claims 1
- GKVWBVIAZSLRSS-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC=3C=C(F)C=CC=3)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 GKVWBVIAZSLRSS-UHFFFAOYSA-N 0.000 claims 1
- VQVGQEICCSENSO-UHFFFAOYSA-N 1-benzyl-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC=3C=CC=CC=3)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 VQVGQEICCSENSO-UHFFFAOYSA-N 0.000 claims 1
- ZOEGPHVJGFFOEC-UHFFFAOYSA-N 1-ethyl-n-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 ZOEGPHVJGFFOEC-UHFFFAOYSA-N 0.000 claims 1
- MVFHHOJYASQLPF-UHFFFAOYSA-N 2-(1-benzyl-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=CC=C1 MVFHHOJYASQLPF-UHFFFAOYSA-N 0.000 claims 1
- GZQKLLZFBUXQTC-UHFFFAOYSA-N 2-(1-butyl-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCCC)C2=CC=N1 GZQKLLZFBUXQTC-UHFFFAOYSA-N 0.000 claims 1
- BJJHMXUCZVIMSD-UHFFFAOYSA-N 2-(1-cyclopentyl-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1C1CCCC1 BJJHMXUCZVIMSD-UHFFFAOYSA-N 0.000 claims 1
- OJEPWYSVIWHLDT-UHFFFAOYSA-N 2-(1-cyclopropyl-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1C1CC1 OJEPWYSVIWHLDT-UHFFFAOYSA-N 0.000 claims 1
- WUUCCRRUHJKPHU-UHFFFAOYSA-N 2-(2,3-dimethyl-1-pent-4-ynylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCCC#C)C2=CC=N1 WUUCCRRUHJKPHU-UHFFFAOYSA-N 0.000 claims 1
- UCJXYUIAWKAIMS-UHFFFAOYSA-N 2-(2,3-dimethyl-1-propan-2-ylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(C(C)C)C2=CC=N1 UCJXYUIAWKAIMS-UHFFFAOYSA-N 0.000 claims 1
- MWRWLDBOALQLJR-UHFFFAOYSA-N 2-(2,3-dimethyl-1-propylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCC)C2=CC=N1 MWRWLDBOALQLJR-UHFFFAOYSA-N 0.000 claims 1
- XPFICLZDEQEYSC-UHFFFAOYSA-N 2-(3-benzyl-2-methyl-1-propylpyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CCC)C(C)=C1CC1=CC=CC=C1 XPFICLZDEQEYSC-UHFFFAOYSA-N 0.000 claims 1
- ATSWNTFZKGWYLK-UHFFFAOYSA-N 2-(3-benzyl-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-yl)-3,4-dihydro-1h-isoquinoline Chemical compound CC=1NC2=CC=NC(N3CC4=CC=CC=C4CC3)=C2C=1CC1=CC=CC=C1 ATSWNTFZKGWYLK-UHFFFAOYSA-N 0.000 claims 1
- WZPQFSDWJQQHFM-UHFFFAOYSA-N 2-[1-(1,3-dioxolan-2-ylmethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1OCCO1 WZPQFSDWJQQHFM-UHFFFAOYSA-N 0.000 claims 1
- ULIVDDMSKBPNFG-UHFFFAOYSA-N 2-[1-(2-ethoxyethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCOCC)C2=CC=N1 ULIVDDMSKBPNFG-UHFFFAOYSA-N 0.000 claims 1
- QSDQLVDRCBMYTA-UHFFFAOYSA-N 2-[1-(2-methoxyethoxymethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(COCCOC)C2=CC=N1 QSDQLVDRCBMYTA-UHFFFAOYSA-N 0.000 claims 1
- CRAZBLOQGMPAHT-UHFFFAOYSA-N 2-[1-(cyclobutylmethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1CCC1 CRAZBLOQGMPAHT-UHFFFAOYSA-N 0.000 claims 1
- YQJBTJAHVSOJMN-UHFFFAOYSA-N 2-[1-(cyclohexylmethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1CCCCC1 YQJBTJAHVSOJMN-UHFFFAOYSA-N 0.000 claims 1
- REFOYKQHOFLXHO-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1CC1 REFOYKQHOFLXHO-UHFFFAOYSA-N 0.000 claims 1
- ZTOWOKXCLUVSRW-UHFFFAOYSA-N 2-[1-(methoxymethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(COC)C2=CC=N1 ZTOWOKXCLUVSRW-UHFFFAOYSA-N 0.000 claims 1
- BFOZFIJJUBUVKA-UHFFFAOYSA-N 2-[1-[(2-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=CC=C1F BFOZFIJJUBUVKA-UHFFFAOYSA-N 0.000 claims 1
- POAXXYVFPYOZAG-UHFFFAOYSA-N 2-[1-[(3-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=CC(F)=C1 POAXXYVFPYOZAG-UHFFFAOYSA-N 0.000 claims 1
- NPNPNKFEFQBAJM-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=C(Cl)C=C1 NPNPNKFEFQBAJM-UHFFFAOYSA-N 0.000 claims 1
- RLIYRUAPVFXNHE-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=C(F)C=C1 RLIYRUAPVFXNHE-UHFFFAOYSA-N 0.000 claims 1
- NIGKAPPVDZFFRK-UHFFFAOYSA-N 2-[1-[(4-methoxyphenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CN1C2=CC=NC(N3CC4=CC=CC=C4CC3)=C2C(C)=C1C NIGKAPPVDZFFRK-UHFFFAOYSA-N 0.000 claims 1
- ORWOJQAEHRBSOB-UHFFFAOYSA-N 2-[2,3-dimethyl-1-(2-methylpropyl)pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CC(C)C)C2=CC=N1 ORWOJQAEHRBSOB-UHFFFAOYSA-N 0.000 claims 1
- GUIMTACSGGQDMX-UHFFFAOYSA-N 2-[2,3-dimethyl-1-(3-methylbut-2-enyl)pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CC=C(C)C)C2=CC=N1 GUIMTACSGGQDMX-UHFFFAOYSA-N 0.000 claims 1
- UJCYOUFQWXNCEJ-UHFFFAOYSA-N 2-[2,3-dimethyl-1-(3-methylbutyl)pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CN1C1=C2C(C)=C(C)N(CCC(C)C)C2=CC=N1 UJCYOUFQWXNCEJ-UHFFFAOYSA-N 0.000 claims 1
- BXINHQKPEDPVGU-UHFFFAOYSA-N 2-[2,3-dimethyl-1-[(4-methylphenyl)methyl]pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC1=C(C)C2=C(N3CC4=CC=CC=C4CC3)N=CC=C2N1CC1=CC=C(C)C=C1 BXINHQKPEDPVGU-UHFFFAOYSA-N 0.000 claims 1
- DQZGPBWETXUNNI-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)methyl]-1,2-dimethylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(C)C(C)=C1CC1=CC=CC(F)=C1 DQZGPBWETXUNNI-UHFFFAOYSA-N 0.000 claims 1
- KOBAQPXFDCHUEF-UHFFFAOYSA-N 2-[3-[(3-fluorophenyl)methyl]-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.CC=1NC2=CC=NC(N3CC4=CC=CC=C4CC3)=C2C=1CC1=CC=CC(F)=C1 KOBAQPXFDCHUEF-UHFFFAOYSA-N 0.000 claims 1
- LOKJNFNRDILBPD-UHFFFAOYSA-N 2-[3-benzyl-1-(cyclopropylmethyl)-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC2CC2)C(C)=C1CC1=CC=CC=C1 LOKJNFNRDILBPD-UHFFFAOYSA-N 0.000 claims 1
- PVDAYZWIUSGBCG-UHFFFAOYSA-N 2-[3-benzyl-1-[(2-fluorophenyl)methyl]-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC=2C(=CC=CC=2)F)C(C)=C1CC1=CC=CC=C1 PVDAYZWIUSGBCG-UHFFFAOYSA-N 0.000 claims 1
- XCCZHTWPFSPKDW-UHFFFAOYSA-N 2-[3-benzyl-1-[(3-fluorophenyl)methyl]-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC=2C=C(F)C=CC=2)C(C)=C1CC1=CC=CC=C1 XCCZHTWPFSPKDW-UHFFFAOYSA-N 0.000 claims 1
- HIYFFQBYVOJEBX-UHFFFAOYSA-N 2-[3-benzyl-1-[(4-fluorophenyl)methyl]-2-methylpyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC=2C=CC(F)=CC=2)C(C)=C1CC1=CC=CC=C1 HIYFFQBYVOJEBX-UHFFFAOYSA-N 0.000 claims 1
- ZUJHLNPTEJJPFV-UHFFFAOYSA-N 2-[3-benzyl-2-methyl-1-(2-methylpropyl)pyrrolo[3,2-c]pyridin-4-yl]-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CC(C)C)C(C)=C1CC1=CC=CC=C1 ZUJHLNPTEJJPFV-UHFFFAOYSA-N 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- IGXPLJHCYYMNGY-UHFFFAOYSA-N 3-benzyl-4-[(4-chlorophenyl)methoxy]-1,2-dimethylpyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C12=C(OCC=3C=CC(Cl)=CC=3)N=CC=C2N(C)C(C)=C1CC1=CC=CC=C1 IGXPLJHCYYMNGY-UHFFFAOYSA-N 0.000 claims 1
- IFSKHAYJVODUGI-UHFFFAOYSA-N 3-benzyl-4-[(4-chlorophenyl)methoxy]-2-methyl-1h-pyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C=12C(CC=3C=CC=CC=3)=C(C)NC2=CC=NC=1OCC1=CC=C(Cl)C=C1 IFSKHAYJVODUGI-UHFFFAOYSA-N 0.000 claims 1
- TWZYKCGVRKVCDJ-UHFFFAOYSA-N 3-benzyl-4-[(4-fluorophenyl)methoxy]-1,2-dimethylpyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C12=C(OCC=3C=CC(F)=CC=3)N=CC=C2N(C)C(C)=C1CC1=CC=CC=C1 TWZYKCGVRKVCDJ-UHFFFAOYSA-N 0.000 claims 1
- CFFNYRZQQAOAAQ-UHFFFAOYSA-N 3-benzyl-4-[(4-fluorophenyl)methoxy]-2-methyl-1h-pyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C=12C(CC=3C=CC=CC=3)=C(C)NC2=CC=NC=1OCC1=CC=C(F)C=C1 CFFNYRZQQAOAAQ-UHFFFAOYSA-N 0.000 claims 1
- WZZXRAMVBFGMIA-UHFFFAOYSA-N 3-benzyl-n-[(4-chlorophenyl)methyl]-1,2-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C12=C(NCC=3C=CC(Cl)=CC=3)N=CC=C2N(C)C(C)=C1CC1=CC=CC=C1 WZZXRAMVBFGMIA-UHFFFAOYSA-N 0.000 claims 1
- XXZGARIBQQPDJU-UHFFFAOYSA-N 3-benzyl-n-[(4-chlorophenyl)methyl]-2-methyl-1h-pyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C=12C(CC=3C=CC=CC=3)=C(C)NC2=CC=NC=1NCC1=CC=C(Cl)C=C1 XXZGARIBQQPDJU-UHFFFAOYSA-N 0.000 claims 1
- QTDYHTIJYCGHTG-UHFFFAOYSA-N 3-benzyl-n-[(4-fluorophenyl)methyl]-1,2-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C12=C(NCC=3C=CC(F)=CC=3)N=CC=C2N(C)C(C)=C1CC1=CC=CC=C1 QTDYHTIJYCGHTG-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 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 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SJEHVDXAMXZVNO-UHFFFAOYSA-N n,1-bis[(4-fluorophenyl)methyl]-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC=3C=CC(F)=CC=3)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 SJEHVDXAMXZVNO-UHFFFAOYSA-N 0.000 claims 1
- XVJRFYVHQMPDMJ-UHFFFAOYSA-N n,n-bis[(4-fluorophenyl)methyl]-1,2,3-trimethylpyrrolo[3,2-c]pyridin-7-amine;hydrochloride Chemical compound Cl.C=12N(C)C(C)=C(C)C2=CN=CC=1N(CC=1C=CC(F)=CC=1)CC1=CC=C(F)C=C1 XVJRFYVHQMPDMJ-UHFFFAOYSA-N 0.000 claims 1
- LNNUNEYNSXYDHY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-1,2,3-trimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(C)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 LNNUNEYNSXYDHY-UHFFFAOYSA-N 0.000 claims 1
- AEYNVCKVLACMGT-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-1-(2-methoxyethyl)-2,3-dimethylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CCOC)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 AEYNVCKVLACMGT-UHFFFAOYSA-N 0.000 claims 1
- BLCYASBLTZZFLJ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2,3-dimethyl-1-(2-methylpropyl)pyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CC(C)C)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 BLCYASBLTZZFLJ-UHFFFAOYSA-N 0.000 claims 1
- JZTSVXBCKAARGM-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2,3-dimethyl-1-propan-2-ylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(C(C)C)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 JZTSVXBCKAARGM-UHFFFAOYSA-N 0.000 claims 1
- KJRXJVDRIGNKSN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2,3-dimethyl-1-propylpyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2N(CCC)C(C)=C(C)C2=C1NCC1=CC=C(F)C=C1 KJRXJVDRIGNKSN-UHFFFAOYSA-N 0.000 claims 1
- QHDOWYKPOXJIRN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2,3-dimethyl-1h-pyrrolo[3,2-c]pyridin-4-amine Chemical compound C=12C(C)=C(C)NC2=CC=NC=1NCC1=CC=C(F)C=C1 QHDOWYKPOXJIRN-UHFFFAOYSA-N 0.000 claims 1
- NNQCAVXWNUKSPR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2,3-dimethyl-1h-pyrrolo[3,2-c]pyridin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=C(C)NC2=CC=NC=1NCC1=CC=C(F)C=C1 NNQCAVXWNUKSPR-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 0 *c1c(*)[n](*)c2c1c(*)ncc2 Chemical compound *c1c(*)[n](*)c2c1c(*)ncc2 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20040070536 | 2004-09-03 | ||
| KR10-2004-0070536 | 2004-09-03 | ||
| PCT/KR2005/002924 WO2006025714A1 (en) | 2004-09-03 | 2005-09-03 | PYRROLO[3,2-c]PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008511618A JP2008511618A (ja) | 2008-04-17 |
| JP2008511618A5 true JP2008511618A5 (enExample) | 2008-10-30 |
| JP5126830B2 JP5126830B2 (ja) | 2013-01-23 |
Family
ID=36000316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007529714A Expired - Fee Related JP5126830B2 (ja) | 2004-09-03 | 2005-09-03 | ピロロ［３，２−ｃ］ピリジン誘導体及びその製造方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US8148529B2 (enExample) |
| EP (1) | EP1784402B1 (enExample) |
| JP (1) | JP5126830B2 (enExample) |
| KR (1) | KR100946219B1 (enExample) |
| CN (1) | CN101018788B (enExample) |
| AT (1) | ATE518858T1 (enExample) |
| AU (1) | AU2005280738B2 (enExample) |
| BR (1) | BRPI0514843A (enExample) |
| CA (1) | CA2578880C (enExample) |
| DK (1) | DK1784402T3 (enExample) |
| ES (1) | ES2367312T3 (enExample) |
| MX (1) | MX2007002214A (enExample) |
| PL (1) | PL1784402T3 (enExample) |
| PT (1) | PT1784402E (enExample) |
| RU (1) | RU2378275C2 (enExample) |
| WO (1) | WO2006025714A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008017466A1 (en) * | 2006-08-08 | 2008-02-14 | Nycomed Gmbh | Pharmaceutically active tetrahydroisoquinoline-substituted benzimidazole derivatives |
| JP5802898B2 (ja) | 2009-07-09 | 2015-11-04 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
| GB2517908A (en) * | 2013-08-14 | 2015-03-11 | Kalvista Pharmaceuticals Ltd | Bicyclic inhibitors |
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| CN103626767A (zh) * | 2013-12-04 | 2014-03-12 | 上海药明康德新药开发有限公司 | 区域选择性的氮杂吲哚及其合成方法 |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| JP7511326B2 (ja) | 2015-10-09 | 2024-07-05 | ウェイブ ライフ サイエンシズ リミテッド | オリゴヌクレオチド組成物およびその方法 |
| SG11201809922YA (en) | 2016-05-31 | 2018-12-28 | Kalvista Pharmaceuticals Ltd | Pyrazole derivatives as plasma kallikrein inhibitors |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| RS63069B1 (sr) | 2017-11-29 | 2022-04-29 | Kalvista Pharmaceuticals Ltd | Dozni oblici koji sadrže inhibitor kalikreina plazme |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| CN114206852A (zh) | 2019-08-09 | 2022-03-18 | 卡尔维斯塔制药有限公司 | 血浆激肽释放酶抑制剂 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3269604D1 (en) | 1981-06-26 | 1986-04-10 | Schering Corp | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| JP3465827B2 (ja) * | 1993-02-24 | 2003-11-10 | 株式会社日清製粉グループ本社 | アザインドール誘導体およびこれを有効成分とする抗潰瘍薬 |
| US5451566A (en) * | 1993-11-17 | 1995-09-19 | Zeneca Limited | Herbicidal pyrrolopyridine compounds |
| CN1044811C (zh) * | 1994-01-19 | 1999-08-25 | 三共株式会社 | 吡咯并哒嗪衍生物 |
| CN1102144C (zh) | 1994-08-13 | 2003-02-26 | 株式会社柳韩洋行 | 新的嘧啶衍生物及其制备方法 |
| EP0849274A1 (en) * | 1996-12-20 | 1998-06-24 | Schering Aktiengesellschaft | Bissteroidal compounds and their use for the preparation of chiral complexes |
| SE9700661D0 (sv) | 1997-02-25 | 1997-02-25 | Astra Ab | New compounds |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| UA59433C2 (uk) * | 1998-01-27 | 2003-09-15 | Авентіс Фармасьютікалс Продактс Інк. | ЗАМІЩЕНІ ОКСОАЗАГЕТЕРОЦИКЛІЧНІ ІНГІБІТОРИ ФАКТОРА Хa ТА ПРОМІЖНІ СПОЛУКИ ДЛЯ ЇХ ОТРИМАННЯ |
| ATE231862T1 (de) | 1998-09-23 | 2003-02-15 | Altana Pharma Ag | Tetrahydropyridoether |
| US20040110785A1 (en) * | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US20040235867A1 (en) | 2001-07-24 | 2004-11-25 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
-
2005
- 2005-09-03 CN CN200580029382XA patent/CN101018788B/zh not_active Expired - Fee Related
- 2005-09-03 EP EP05781131A patent/EP1784402B1/en not_active Expired - Lifetime
- 2005-09-03 ES ES05781131T patent/ES2367312T3/es not_active Expired - Lifetime
- 2005-09-03 DK DK05781131.7T patent/DK1784402T3/da active
- 2005-09-03 BR BRPI0514843-0A patent/BRPI0514843A/pt not_active Application Discontinuation
- 2005-09-03 CA CA2578880A patent/CA2578880C/en not_active Expired - Fee Related
- 2005-09-03 AT AT05781131T patent/ATE518858T1/de active
- 2005-09-03 RU RU2007112108/04A patent/RU2378275C2/ru not_active IP Right Cessation
- 2005-09-03 WO PCT/KR2005/002924 patent/WO2006025714A1/en not_active Ceased
- 2005-09-03 KR KR1020050082008A patent/KR100946219B1/ko not_active Expired - Fee Related
- 2005-09-03 MX MX2007002214A patent/MX2007002214A/es active IP Right Grant
- 2005-09-03 JP JP2007529714A patent/JP5126830B2/ja not_active Expired - Fee Related
- 2005-09-03 US US11/574,393 patent/US8148529B2/en not_active Expired - Fee Related
- 2005-09-03 PT PT05781131T patent/PT1784402E/pt unknown
- 2005-09-03 AU AU2005280738A patent/AU2005280738B2/en not_active Ceased
- 2005-09-03 PL PL05781131T patent/PL1784402T3/pl unknown
-
2011
- 2011-11-15 US US13/296,378 patent/US8513277B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008511618A5 (enExample) | ||
| JP2008255122A5 (enExample) | ||
| JP2004521117A5 (enExample) | ||
| JP2009507036A5 (enExample) | ||
| EP1562949A4 (en) | METHOD FOR PRODUCING PYRROLOTRIAZIN COMPOUNDS SUITABLE AS KINASEINHIBITORS | |
| JP2010540643A5 (enExample) | ||
| JP2009542613A5 (enExample) | ||
| JP2004520324A5 (enExample) | ||
| JP2005053931A5 (enExample) | ||
| MX2010004819A (es) | Derivados de [1h-pirazolo[3,4-b]piridin-4-il]-fenilo o piridin-2-ilo como proteina cinasa c-theta. | |
| BR0109577A (pt) | Composto, processo para preparar o mesmo, composição farmacêutica, uso de um composto, e, método para tratar cânceres em um animal de sangue quente | |
| JP2005527492A5 (enExample) | ||
| JP2006151984A5 (enExample) | ||
| SI3106463T1 (en) | Compounds of substituted pyrazolo (1,5-) pyrimidine as inhibitors of TRK kinase | |
| JP2008516986A5 (enExample) | ||
| JP2003525279A5 (enExample) | ||
| MX2007006497A (es) | Nuevos derivados de pirrolo [3,2-d] pirimidin-4-ona y su uso en terapia. | |
| JP2011510929A5 (enExample) | ||
| RU95113966A (ru) | Пиразолопиримидины, фармацевтическая композиция и способ лечения | |
| JP2007521280A5 (enExample) | ||
| EP2620432A3 (en) | Diarylhydantoin compounds | |
| JP2011519910A5 (enExample) | ||
| JP2012523440A5 (enExample) | ||
| WO2004020430A3 (fr) | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique | |
| RU2007112108A (ru) | Производные пирроло[3, 2-с]пиридина и способ их получения |