JP2008511618A5 - - Google Patents
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- 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
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- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- -1 methoxy, ethoxy, hydroxy, cyclopropyl Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000003545 alkoxy group Chemical group 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
- 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
- HWFKBPOESCHRHF-UHFFFAOYSA-N 2-(2-methyl-3-prop-2-enyl-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)CC=C)C2=CC=N1 HWFKBPOESCHRHF-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
- WTPQWYUHOUTNGV-UHFFFAOYSA-N 2-[3-benzyl-4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-methylpyrrolo[3,2-c]pyridin-1-yl]ethanol;hydrochloride Chemical compound Cl.C12=C(N3CC4=CC=CC=C4CC3)N=CC=C2N(CCO)C(C)=C1CC1=CC=CC=C1 WTPQWYUHOUTNGV-UHFFFAOYSA-N 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 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
- 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
- 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
- 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 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 0 *c1c(*)[n](*)c2c1c(*)ncc2 Chemical compound *c1c(*)[n](*)c2c1c(*)ncc2 0.000 description 2
Claims (7)
- 化学式１の化合物またはその薬剤学的に許容可能な塩：
Ｒ ２ は、直鎖状または分枝状のＣ１−Ｃ６のアルキル基であり、
Ｒ３は、水素；直鎖状または分枝状のＣ１−Ｃ６のアルキル基；直鎖状または分枝状のＣ２−Ｃ６のアルケニル基；またはハロゲンに一つ以上選択的に置換可能なベンジル基であり、
Ｒ４は、１，２，３，４−テトラヒドロイソキノリニル基；ハロゲンに一つ以上選択的に置換可能なベンジルオキシ基；または水素、直鎖状または分枝状のＣ１−Ｃ５のアルキルカルボニル、フェノキシカルボニル、ハロゲンに一つ以上選択的に置換可能なベンジル、及びハロゲンに一つ以上選択的に置換可能なベンゾイルからなる群から選択された１つまたは２つの置換基に置換されたアミノ基である。 - Ｒ１は、水素；直鎖状または分枝状のＣ１−Ｃ６のアルキル基；メトキシ、エトキシ、ヒドロキシ、シクロプロピル、シクロブチル、シクロヘキシル、メチルチアゾリル、及び１，３−ジオキソランイルからなる群から選択された一つ以上の置換基に置換されたＣ１−Ｃ３のアルキル基；直鎖状または分枝状のＣ２−Ｃ６のアルケニル基；直鎖状または分枝状のＣ２−Ｃ６のアルキニル基；シクロプロピル；シクロペンチル；またはハロゲン、メチル、及びメトキシからなる群から選択された一つ以上の置換基に選択的に置換可能なベンジル基であり、
Ｒ２は、直鎖状または分枝状のＣ１−Ｃ３のアルキル基であり、
Ｒ３は、水素；直鎖状または分枝状のＣ１−Ｃ３のアルキル基；直鎖状または分枝状のＣ２−Ｃ５のアルケニル基；またはハロゲンに一つ以上選択的に置換可能なベンジル基であり、
Ｒ４は、１，２，３，４−テトラヒドロイソキノリニル；ハロゲンに一つ以上選択的に置換可能なベンジルオキシ基；または水素、直鎖状または分枝状のＣ１−Ｃ５のアルキルカルボニル、フェノキシカルボニル、ハロゲンに一つ以上選択的に置換可能なベンジル、及びハロゲンに一つ以上選択的に置換可能なベンゾイルからなる群から選択された１つまたは２つの置換基に置換されたアミノ基であることを特徴とする請求項１に記載の化合物またはその薬剤学的に許容可能な塩。 - 2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン;
2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-メトキシエチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
1-アリル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-ベンジル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1,2,3-トリメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-エチル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-プロピル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-ブチル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-イソプロピル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-イソブチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
2,3-ジメチル-1-(3-メチルブチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
2,3-ジメチル-1-シクロプロピル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-シクロペンチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-シクロプロピルメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-シクロブチルメチル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-シクロヘキシルメチル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(ペント-4-イニル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(3-メチルブト-2-エニル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-ヒドロキシエチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-メトキシメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-エトキシエチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-メトキシエトキシメチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-([1,3]ジオキソラン-2-イルメチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-フルオロベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(3-フルオロベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(4-フルオロベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(4-クロロベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(4-メチルベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(4-メトキシベンジル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-メチルチアゾール-4-メチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン;
2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1,2,3-トリメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-エチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-プロピル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-アリル-2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-イソプロピル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-イソブチル-2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-シクロプロピルメチル-2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-メトキシエチル)-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-([1,3]ジオキソラン-2-イルメチル)-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-ベンジル-2,3-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-フルオロベンジル)-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(3-フルオロベンジル)-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(4-フルオロベンジル)-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-ベンジル-N-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N,N-ジ-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-アセチル-N-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-イソブチリル-N-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-ベンゾイル-N-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-(2-クロロベンゾイル)-N-(4-フルオロベンジル)]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
7-[N-(4-フルオロベンジル)-N-フェノキシカルボニル]アミノ-1,2,3-トリメチル-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン;
3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1,2-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-エチル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-プロピル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-アリル-3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-イソブチル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-シクロプロピル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-シクロプロピルメチル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-(2-メトキシエチル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-(2-ヒドロキシエチル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-([1,3]ジオキソラン-2-イルメチル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1,3-ジベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-(2-フルオロベンジル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-(3-フルオロベンジル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1-(4-フルオロベンジル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジンナトリウム塩；
3-ベンジル-2-メチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1,2-ジメチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-2-メチル-4-(4-クロロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1,2-ジメチル-4-(4-クロロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-2-メチル-4-(4-フルオロベンジルオキシ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1,2-ジメチル-4-(4-フルオロベンジルオキシ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-2-メチル-4-(4-クロロベンジルオキシ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-ベンジル-1,2-ジメチル-4-(4-クロロベンジルオキシ)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-(3-フルオロベンジル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-(3-フルオロベンジル)-1,2-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
3-アリル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；及び
3-アリル-1,2-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩
からなる群から選択されたことを特徴とする請求項１に記載の化合物またはその薬剤学的に許容可能な塩。 - 2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン;
2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
2,3-ジメチル-1-(2-メトキシエチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1,2,3-トリメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩;
1-エチル-2,3-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
2,3-ジメチル-1-(2-ヒドロキシエチル)-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-1,2-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-1-エチル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-1-シクロプロピル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-1-(2-メトキシエチル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-1-([1,3]ジオキソラン-2-イルメチル)-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
1,3-ジベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩；
3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジンナトリウム塩；及び
3-ベンジル-2-メチル-4-(4-フルオロベンジルアミノ)-1H-ピロロ[3,2-c]ピリジン塩酸塩
からなる群から選択されたことを特徴とする請求項３に記載の化合物またはその薬剤学的に許容可能な塩。 - 3-ベンジル-2-メチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩または3-ベンジル-1,2-ジメチル-4-(1,2,3,4-テトラヒドロイソキノリン-2-イル)-1H-ピロロ[3,2-c]ピリジン塩酸塩である、請求項４に記載の化合物またはその薬剤学的に許容可能な塩。
- （ａ）亜硝酸ナトリウム溶液を化学式２の化合物に加えた後、得られた生成物を還元させ、化学式３の化合物を製造する段階と、
（ｂ）化学式３の化合物を化学式４の化合物と反応させ、化学式５の化合物を製造する段階と、
（ｃ）化学式５の化合物の環化反応を行い、化学式６の化合物を製造する段階と、
（ｄ）化学式６の化合物をハロゲン化し、化学式７の化合物を製造する段階と、
（ｅ）化学式７の化合物をＲ４−Ｈと反応させ、化学式１ａの化合物を製造する段階と、
（ｆ）化学式１ａの化合物をＲ１−Ｘと反応させ、化学式１の化合物を製造する段階とを含む化学式１の化合物またはその薬剤学的に許容可能な塩の製造方法：
- 治療学的有効量の請求項１に記載の化学式１の化合物またはその薬剤学的に許容可能な塩、及び薬剤学的に許容可能な担体を含む、薬剤学的組成物。
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| KR10-2004-0070536 | 2004-09-03 | ||
| KR20040070536 | 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 |
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| US (2) | US8148529B2 (ja) |
| EP (1) | EP1784402B1 (ja) |
| JP (1) | JP5126830B2 (ja) |
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| CN (1) | CN101018788B (ja) |
| AT (1) | ATE518858T1 (ja) |
| AU (1) | AU2005280738B2 (ja) |
| BR (1) | BRPI0514843A (ja) |
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| ES (1) | ES2367312T3 (ja) |
| HK (1) | HK1105977A1 (ja) |
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| WO2008017466A1 (en) * | 2006-08-08 | 2008-02-14 | Nycomed Gmbh | Pharmaceutically active tetrahydroisoquinoline-substituted benzimidazole derivatives |
| CN102470126A (zh) | 2009-07-09 | 2012-05-23 | 拉夸里亚创药株式会社 | 用于治疗与异常肠胃运动有关的疾病的酸泵拮抗剂 |
| 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 |
| GB2517908A (en) * | 2013-08-14 | 2015-03-11 | Kalvista Pharmaceuticals Ltd | Bicyclic inhibitors |
| 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 |
| EP3359523A4 (en) | 2015-10-09 | 2019-07-24 | Wave Life Sciences Ltd. | OLIGONUCLEOTIDE COMPOSITIONS AND RELATED METHODS |
| RS60600B1 (sr) | 2016-05-31 | 2020-08-31 | Kalvista Pharmaceuticals Ltd | Derivati pirazola kao inhibitori kalikreina plazme |
| 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 |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| RU2020121151A (ru) | 2017-11-29 | 2021-12-29 | Калвиста Фармасьютикалз Лимитед | Дозированные формы, содержащие ингибитор плазменного калликреина |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
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| EP0068378B1 (en) * | 1981-06-26 | 1986-03-05 | Schering Corporation | 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 |
| NZ278675A (en) * | 1994-01-19 | 1997-07-27 | Sankyo Co | Pyrrolopyridazine derivatives; medicaments |
| ES2201112T3 (es) | 1994-08-13 | 2004-03-16 | Yuhan Corporation | Nuevos derivados de pirimidina y procedimientos para su preparacion. |
| 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 |
| KR20010034442A (ko) * | 1998-01-27 | 2001-04-25 | 아벤티스 파마슈티칼즈 프로덕츠 인코포레이티드 | 치환된 옥소아자헤테로사이클릴 인자 Ｘａ 억제제 |
| ID28896A (id) | 1998-09-23 | 2001-07-12 | Byk Gulden Lomberg Chem Fab | Tetrahidro pirido eter |
| US20040110785A1 (en) * | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| WO2003009852A1 (en) * | 2001-07-24 | 2003-02-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
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