JP2020524687A - ジヒドロ−ピロロ−ピリジン誘導体 - Google Patents
ジヒドロ−ピロロ−ピリジン誘導体 Download PDFInfo
- Publication number
- JP2020524687A JP2020524687A JP2019570547A JP2019570547A JP2020524687A JP 2020524687 A JP2020524687 A JP 2020524687A JP 2019570547 A JP2019570547 A JP 2019570547A JP 2019570547 A JP2019570547 A JP 2019570547A JP 2020524687 A JP2020524687 A JP 2020524687A
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- JP
- Japan
- Prior art keywords
- pyridin
- optionally substituted
- pyrrolo
- dihydro
- dimethyl
- Prior art date
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- Granted
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- JKWQHCSGMTWRIQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NCCC2=N1 JKWQHCSGMTWRIQ-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 274
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 86
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 77
- 208000035475 disorder Diseases 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 51
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 46
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 22
- 230000001404 mediated effect Effects 0.000 claims abstract description 19
- 208000002193 Pain Diseases 0.000 claims abstract description 17
- 208000019116 sleep disease Diseases 0.000 claims abstract description 11
- 206010012335 Dependence Diseases 0.000 claims abstract description 8
- -1 cyano, hydroxy Chemical group 0.000 claims description 200
- 125000001424 substituent group Chemical group 0.000 claims description 83
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 80
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 38
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 37
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 22
- 208000028017 Psychotic disease Diseases 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 208000010877 cognitive disease Diseases 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 208000018737 Parkinson disease Diseases 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- QPUHFBHNFXIENJ-UHFFFAOYSA-N CC1=C(C2=C(C(=N1)NC)CN(C2)C(=O)OC1CC=2C(=NC=CC=2)C1)C Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(=O)OC1CC=2C(=NC=CC=2)C1)C QPUHFBHNFXIENJ-UHFFFAOYSA-N 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 10
- 208000023105 Huntington disease Diseases 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 208000012661 Dyskinesia Diseases 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 7
- AOULMVARWGZMTH-UHFFFAOYSA-N CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=NC=NS1)=O)C Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=NC=NS1)=O)C AOULMVARWGZMTH-UHFFFAOYSA-N 0.000 claims description 7
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- MBKZJWJLZSNWRA-UHFFFAOYSA-N 2-[1-[2-(difluoromethoxy)pyridin-4-yl]azetidin-3-yl]-1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]ethanone Chemical compound FC(OC1=NC=CC(=C1)N1CC(C1)CC(=O)N1CC=2C(=NC(=C(C=2C1)C)C)NC)F MBKZJWJLZSNWRA-UHFFFAOYSA-N 0.000 claims description 6
- 208000020706 Autistic disease Diseases 0.000 claims description 6
- 206010002022 amyloidosis Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- YRZUDHYYIUIDIZ-UHFFFAOYSA-N 5,6,7-trimethyl-2-[2-(1-pyridin-3-ylazetidin-3-yl)acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CN=CC=C2)CC(CC(=O)N2CC3=C(C(=O)N(C(=C3C)C)C)C2)C1 YRZUDHYYIUIDIZ-UHFFFAOYSA-N 0.000 claims description 5
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- JRKLWKSDYCTMSD-UHFFFAOYSA-N 2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]-1-[1,6,7-trimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]ethanone Chemical compound N(C)C1=NC(=C(C=2C(C)N(CC1=2)C(=O)CC1CN(C2=CC(C(F)(F)F)=NC=C2)C1)C)C JRKLWKSDYCTMSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 4
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 4
- 201000010374 Down Syndrome Diseases 0.000 claims description 4
- 206010019196 Head injury Diseases 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
- QCJULGMSVIUYLJ-UHFFFAOYSA-N 1-[4-(cyclopropylmethylamino)-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyrimidin-4-ylazetidin-3-yl)ethanone Chemical compound C1C(CNC2=NC(C)=C(C3=C2CN(C3)C(=O)CC2CN(C3=NC=NC=C3)C2)C)C1 QCJULGMSVIUYLJ-UHFFFAOYSA-N 0.000 claims description 3
- PRLFPWQBJHQKIV-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C(F)(F)F)=O)C PRLFPWQBJHQKIV-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 102000029797 Prion Human genes 0.000 claims description 3
- 108091000054 Prion Proteins 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 3
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 3
- 206010013781 dry mouth Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 3
- 201000008319 inclusion body myositis Diseases 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- LVFPJWYJRQDRAT-UHFFFAOYSA-N 1-(4-methoxy-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl)-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound COC1=NC(=C(C2=C1CN(C2)C(CC1CN(C1)C=1C=NC=CC=1)=O)C)C LVFPJWYJRQDRAT-UHFFFAOYSA-N 0.000 claims description 2
- UDLUVDUDOHHJOT-UHFFFAOYSA-N 1-(4-methoxy-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl)-2-(1-pyrimidin-5-ylazetidin-3-yl)ethanone Chemical compound N1(C2=CN=CN=C2)CC(CC(=O)N2CC3=C(C(=NC(=C3C)C)OC)C2)C1 UDLUVDUDOHHJOT-UHFFFAOYSA-N 0.000 claims description 2
- UCRJUHXDLGHGFB-UHFFFAOYSA-N 1-(6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl)-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound CC1=C(C2=C(C=N1)CN(C2)C(CC1CN(C1)C=1C=NC=CC=1)=O)C UCRJUHXDLGHGFB-UHFFFAOYSA-N 0.000 claims description 2
- UXNNYJAVHXRYKY-UHFFFAOYSA-N 1-[4-(difluoromethoxy)-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyrimidin-5-ylazetidin-3-yl)ethanone Chemical compound C(OC1=NC(C)=C(C2=C1CN(C2)C(=O)CC1CN(C2=CN=CN=C2)C1)C)(F)F UXNNYJAVHXRYKY-UHFFFAOYSA-N 0.000 claims description 2
- IQVOZNJJMUSCOZ-UHFFFAOYSA-N 1-[4-[(dimethylamino)methyl]-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound C(C1=NC(=C(C2=C1CN(C2)C(=O)CC1CN(C2=CN=CC=C2)C1)C)C)N(C)C IQVOZNJJMUSCOZ-UHFFFAOYSA-N 0.000 claims description 2
- RUCLNTFQDCNNAK-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(1-methylpyrazol-4-yl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound N=1N(C=C(C=1)C1=NC(=C(C2=C1CN(C2)C(=O)CC1CN(C2=CN=CC=C2)C1)C)C)C RUCLNTFQDCNNAK-UHFFFAOYSA-N 0.000 claims description 2
- PSVCJGQQYVPNPK-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyrimidin-5-ylazetidin-3-yl)ethanone Chemical compound N1(C2=CN=CN=C2)CC(CC(=O)N2CC3=C(C(=NC(=C3C2)NC)C)C)C1 PSVCJGQQYVPNPK-UHFFFAOYSA-N 0.000 claims description 2
- IHVNXDZGSJJBPX-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(5-fluoro-2,3-dihydro-1H-inden-2-yl)ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CC2=CC=C(C=C2C1)F)=O)C IHVNXDZGSJJBPX-UHFFFAOYSA-N 0.000 claims description 2
- YGKZQISZKPFFDV-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(1,3,4-thiadiazol-2-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C=1SC=NN=1)=O)C YGKZQISZKPFFDV-UHFFFAOYSA-N 0.000 claims description 2
- ZNPQEOTVQBKCJE-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(2-methylpyridin-4-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C)=O)C ZNPQEOTVQBKCJE-UHFFFAOYSA-N 0.000 claims description 2
- WGGGULHBHYSVOD-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(6-fluoropyridin-3-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C=1C=NC(=CC=1)F)=O)C WGGGULHBHYSVOD-UHFFFAOYSA-N 0.000 claims description 2
- SDZQJMCXLDSQML-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(1H-pyrazol-4-yl)propan-1-one Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CCC=1C=NNC=1)=O)C SDZQJMCXLDSQML-UHFFFAOYSA-N 0.000 claims description 2
- YHVZLWRQGISNQE-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=C(C=CC(=C1)CCC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)OC YHVZLWRQGISNQE-UHFFFAOYSA-N 0.000 claims description 2
- BGCZOPIJDNQQEC-UHFFFAOYSA-N 2-[1-[2-(difluoromethoxy)pyridin-4-yl]azetidin-3-yl]-1-[1,6,7-trimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]ethanone Chemical compound N1(C2=CC(OC(F)F)=NC=C2)CC(CC(=O)N2C(C3=C(C(=NC(=C3C)C)NC)C2)C)C1 BGCZOPIJDNQQEC-UHFFFAOYSA-N 0.000 claims description 2
- YPHCYHOTYHNIMX-UHFFFAOYSA-N 4-[3-[2-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-oxoethyl]azetidin-1-yl]pyridine-2-carbonitrile Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C#N)=O)C YPHCYHOTYHNIMX-UHFFFAOYSA-N 0.000 claims description 2
- NACFKBRRTJAIRY-UHFFFAOYSA-N 4-[3-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-oxopropyl]benzonitrile Chemical compound C1=C(C=CC(=C1)CCC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)C#N NACFKBRRTJAIRY-UHFFFAOYSA-N 0.000 claims description 2
- QFQAXYYKZBIRPP-HOTGVXAUSA-N 5,6,7-trimethyl-2-[2-[(1S,2R)-2-pyridin-3-ylcyclopropyl]acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound CN1C(C2=C(C(=C1C)C)CN(C2)C(C[C@H]1[C@@H](C1)C=1C=NC=CC=1)=O)=O QFQAXYYKZBIRPP-HOTGVXAUSA-N 0.000 claims description 2
- MASQMSKSYJLVPR-UHFFFAOYSA-N 5,6,7-trimethyl-2-[2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CC(C(F)(F)F)=NC=C2)CC(CC(=O)N2CC3=C(C(=O)N(C(=C3C)C)C)C2)C1 MASQMSKSYJLVPR-UHFFFAOYSA-N 0.000 claims description 2
- LYYCRODRVBDGRZ-UHFFFAOYSA-N 6,7-dimethyl-2-[2-(1-pyridin-3-ylazetidin-3-yl)acetyl]-3,5-dihydro-1H-pyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CN=CC=C2)CC(CC(=O)N2CC3=C(C(=O)NC(C)=C3C)C2)C1 LYYCRODRVBDGRZ-UHFFFAOYSA-N 0.000 claims description 2
- RLYJDRPFCCKBIB-UHFFFAOYSA-N CC1=C(C2=C(C(=N1)NC)CN(C2)C(=O)OC1CN(C1)C=1C=NC=CC=1)C Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(=O)OC1CN(C1)C=1C=NC=CC=1)C RLYJDRPFCCKBIB-UHFFFAOYSA-N 0.000 claims description 2
- BKCWQEAFGMHXRP-UHFFFAOYSA-N CNc1nc(C)c(C)c2CN(Cc12)C(=O)CC1Cc2ccccc2C1 Chemical compound CNc1nc(C)c(C)c2CN(Cc12)C(=O)CC1Cc2ccccc2C1 BKCWQEAFGMHXRP-UHFFFAOYSA-N 0.000 claims description 2
- SOQRQGFHFRROSV-UHFFFAOYSA-N [6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-(1-methylpyrazol-4-yl)methanone Chemical compound N=1N(C=C(C=1)C(=O)N1CC2=C(C(=NC(C)=C2C)NC)C1)C SOQRQGFHFRROSV-UHFFFAOYSA-N 0.000 claims description 2
- MXKFZWRULHJPIV-LLVKDONJSA-N [6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-[(3R)-oxolan-3-yl]methanone Chemical compound O1CC[C@H](C1)C(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1 MXKFZWRULHJPIV-LLVKDONJSA-N 0.000 claims description 2
- FQCIVZDKIPZMHS-UHFFFAOYSA-N cyclopropyl-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound C1(C(=O)N2CC3=C(C(=NC(=C3C2)NC)C)C)CC1 FQCIVZDKIPZMHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000532 dioxanyl group Chemical group 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 229960004502 levodopa Drugs 0.000 claims description 2
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Classifications
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- 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
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- 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
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- 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
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Abstract
Description
本発明は、一般に、ムスカリン性M4受容体の活性化剤である新規ジヒドロ−ピロロ−ピリジン誘導体、その塩、その医薬組成物、ならびに統合失調症、アルツハイマー病、レビー小体型認知症、パーキンソン病、および関係する記憶および実行機能障害、動揺、およびそれらに関連する精神病などのM4媒介性の疾患および障害の処置におけるその使用に関する。
統合失調症、アルツハイマー病、パーキンソン病、ハンチントン病、うつ病および様々な他の神経学的/神経変性疾患を有する患者は、彼らの日常生活に衰弱性の混乱をもたらす行動および認知障害に頻繁に罹患する。長年にわたって、行動および認知機能においていくらかの改善をもたらす多くの薬理学的処置が発見されてきた。しかし、改善はそれほど大きくはなく、よくあることであるが、錐体外路および代謝の副作用を含む、これらの処置に関連する根本的な用量制限的悪影響は、部分的な応答性、およびノンコンプライアンスにつながる。
本発明は、部分的には、式Iの化合物:
[式中、
各R1は、存在する場合、独立して、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、必要に応じて置換されている−O−(C3〜C6)シクロアルキル、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、
aは、0、1、2、および3から選択される整数であり、
各R2は、存在する場合、独立して、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、
bは、0、1、2、3、および4から選択される整数であり、
R3は、存在する場合、独立して、ハロゲン、シアノ、ヒドロキシ、オキソ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、必要に応じて置換されている−O−(C3〜C6)シクロアルキル、必要に応じて置換されている(5〜6員の)ヘテロアリール、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、但し、R3が、オキソである場合、
cは、0および1から選択される整数であり、
Lは、−(CH2)m−、および−O−から選択され、ここで、mは、0、1および2から選択される整数であり、
Aは、存在しないか、または(C3〜C6)シクロアルキルおよび(4〜10員の)ヘテロシクロアルキルからなる群から選択され、ここで、前記シクロアルキルおよびヘテロシクロアルキルはそれぞれ、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から独立して選択される1〜5個の置換基で必要に応じて置換されており、
Eは、(C3〜C12)シクロアルキル、(C6〜C10)アリール、(5〜6員の)ヘテロシクロアルキル、および(5〜10員の)ヘテロアリールから選択され、ここで、前記シクロアルキル、アリール、およびヘテロアリールは、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、メチルオキセタニル、−N(R4)(R5)、−N(R4)(C=(O)R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から独立して選択される1〜5個の置換基で必要に応じて置換されており、
R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択されるか、またはR4およびR5は、それらが結合している窒素と一緒になって、必要に応じて置換されている(4〜6員の)ヘテロシクロアルキルを形成する]を提供する。
本文書内の表題は、読者によるその再検討を迅速化するために利用されるにすぎない。それらは、いかなる様式においても、本発明または特許請求の範囲を限定するものと解釈されるべきではない。
特許請求の範囲を含む本出願の全体にわたって使用される場合、以下の用語は、特に別段の指定がない限り、以下で定義される意味を有する。複数形および単数形は、数の指示以外では、交換可能なものとして扱われるべきである。
化合物
[式中、
各R1は、独立して、ハロゲン、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から選択され、
aは、1、2および3から選択される整数であり、
R2は、存在する場合、必要に応じて置換されている(C1〜C6)アルキルであり、
bは、0および1から選択される整数であり、
R4およびR5は、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択され、
Eは、(5〜6員の)ヘテロアリールであり、ここで、前記ヘテロアリールは、ハロゲン、シアノ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C1〜C6)アルコキシ、および−N(R4)(R5)からなる群から独立して選択される1〜3個の置換基で必要に応じて置換されており、ここで、R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択される]
である。
[式中、
各R1は、独立して、ハロゲン、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から選択され、
aは、1、2および3から選択される整数であり、
R2は、存在する場合、必要に応じて置換されている(C1〜C6)アルキルであり、
bは、0および1から選択される整数であり、
R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択され、
Eは、(5〜6員の)ヘテロアリールであり、ここで、前記ヘテロアリールは、ハロゲン、シアノ、ヒドロキシ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C1〜C6)アルコキシ、および−N(R4)(R5)からなる群から独立して選択される1〜3個の置換基で必要に応じて置換されており、ここで、R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択される]
である。
5,6,7−トリメチル−2−{[1−(ピリジン−3−イル)アゼチジン−3−イル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(1,2,4−チアジアゾール−5−イル)アゼチジン−3−イル]エタノン;
2−{1−[2−(ジフルオロメトキシ)ピリジン−4−イル]アゼチジン−3−イル}−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(ピリジン−3−イル)アゼチジン−3−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート;
6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン−6−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート;
1−(4−アミノ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−(4−アミノ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリジン−3−イル)シクロプロピル]エタノン;
2−[1−(ピリジン−3−イル)アゼチジン−3−イル]−1−(4,6,7−トリメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)エタノン;
1−[6,7−ジメチル−4−(1−メチル−1H−ピラゾール−4−イル)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−{4−[(ジメチルアミノ)メチル]−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル}−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−[4−(ジメチルアミノ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジフルオロメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジメチルアミノ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
6,7−ジメチル−2−{[1−(ピリジン−3−イル)アゼチジン−3−イル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−{4−[(シクロプロピルメチル)アミノ]−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル}−2−[1−(ピリミジン−4−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−4−イル)アゼチジン−3−イル]エタノン;
2−(2,3−ジヒドロ−1H−インデン−2−イル)−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
5,6,7−トリメチル−2−({1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}アセチル)−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
5,6,7−トリメチル−2−{[trans−2−(ピリジン−3−イル)シクロプロピル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリミジン−5−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリミジン−5−イル)シクロプロピル]エタノン;
4−{3−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−オキソプロピル}ベンゾニトリル;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−(4−メトキシフェニル)プロパン−1−オン;
2−[trans−2−(6−クロロピリジン−3−イル)シクロプロピル]−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(2−メチルピリジン−4−イル)アゼチジン−3−イル]エタノン;
4−(3−{2−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−オキソエチル}アゼチジン−1−イル)ピリジン−2−カルボニトリル;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(1,3,4−チアジアゾール−2−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−(1H−ピラゾール−4−イル)プロパン−1−オン;
1−[4−(ジフルオロメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−{1−[2−(ジフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(4−フルオロフェニル)シクロプロピル]エタノン;
2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−メチルピリジン−3−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−メチルピリジン−3−イル)シクロプロピル]エタノン;
[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル](1−メチル−1H−ピラゾール−4−イル)メタノン;
2−{1−[2−(ジフルオロメトキシ)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(6−フルオロピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(4−メトキシ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[4−(メトキシメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(4−メトキシ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジフルオロメトキシ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−(5−フルオロ−2,3−ジヒドロ−1H−インデン−2−イル)エタノン;
シクロプロピル[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]メタノン;
[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル][(3R)−テトラヒドロフラン−3−イル]メタノン
からなる群から選択される化合物;および
そのN−オキシド、またはその薬学的に許容される塩、もしくはN−オキシドの薬学的に許容される塩を対象とする。
薬理学
製剤
(i)アセチルコリンエステラーゼ阻害剤、例えば、塩酸ドネペジル(ARICEPT、MEMAC)、サリチル酸フィゾスチグミン(ANTILIRIUM)、硫酸フィゾスチグミン(ESERINE)、メトリホネート、ネオスチグミン、ガンスチグミン、ピリドスチグミン(MESTINON)、アンベノニウム(MYTELASE)、デマルカリウム(demarcarium)、Debio 9902(ZT−1としても公知である;Debiopharm)、リバスチグミン(EXELON)、ラドスチギル、NP−0361、臭化水素酸ガランタミン(RAZADYNE、RIMINYL、NIVALIN)、タクリン(COGNEX)、トルセリン、マレイン酸ベルナクリン、メモキン、フペルジンA(HUP−A;NeuroHitech)、フェンセリン、エドロホニウム(ENLON、TENSILON)、およびINM−176;
(ii)アミロイド−β(またはその断片)、例えば、汎HLA DR結合エピトープとコンジュゲートしているAβ1〜15(PADRE)、ACC−001(Elan/Wyeth)、ACI−01、ACI−24、AN−1792、Affitope AD−01、CAD106、およびV−950;
(iii)アミロイド−β(またはその断片)に対する抗体、例えば、ポネズマブ、ソラネズマブ、バピネオズマブ(AAB−001としても公知である)、AAB−002(Wyeth/Elan)、ACI−01−Ab7、BAN−2401、静脈内Ig(GAMMAGARD)、LY2062430(ヒト化m266;Lilly)、R1450(Roche)、ACU−5A5、huC091、ならびに国際特許公開第WO04/032868号、第WO05/025616号、第WO06/036291号、第WO06/069081号、第WO06/118959号に、米国特許公開第US2003/0073655号、第US2004/0192898号、第US2005/0048049号、第US2005/0019328号に、欧州特許公開第EP0994728号および第1257584号に、および米国特許第5,750,349号に開示されているもの;
(iv)アミロイド低下剤または阻害剤(アミロイド産生、蓄積、および線維化を低減させるものを含む)、例えば、ジメボン、ダブネチド、エプロジセート、ロイプロリド、SK−PC−B70M、セレコキシブ、ロバスタチン、アナプソス、オキシラセタム、プラミラセタム、バレニクリン、ニセルゴリン、コロストリニン、ビスノルシムセリン(BNCとしても公知である)、NIC5−15(Humanetics)、E−2012(エーザイ株式会社)、ピオグリタゾン、クリオキノール(PBT1としても公知である)、PBT2(Prana Biotechnology)、フルルビプロフェン(ANSAID、FROBEN)およびそのR−エナンチオマーのタレンフルルビル(FLURIZAN)、ニトロフルルビプロフェン、フェノプロフェン(FENOPRON、NALFON)、イブプロフェン(ADVIL、MOTRIN、NUROFEN)、イブプロフェンリシネート、メクロフェナム酸、メクロフェナム酸ナトリウム(MECLOMEN)、インドメタシン(INDOCIN)、ジクロフェナクナトリウム(VOLTAREN)、ジクロフェナクカリウム、スリンダク(CLINORIL)、スリンダク硫化物、ジフルニサル(DOLOBID)、ナプロキセン(NAPROSYN)、ナプロキセンナトリウム(ANAPROX、ALEVE)、ARC031(Archer Pharmaceuticals)、CAD−106(Cytos)、LY450139(Lilly)、インスリン分解酵素(インスリシンとしても公知である)、イチョウ(gingko biloba)抽出物EGb−761(ROKAN、TEBONIN)、トラミプロセート(CEREBRIL、ALZHEMED)、エプロジセート(FIBRILLEX、KIACTA)、化合物W[3,5−ビス(4−ニトロフェノキシ)安息香酸]、NGX−96992、ネプリライシン(中性エンドペプチダーゼ(NEP)としても公知である)、シロ−イノシトール(シリトールとしても公知である)、アトルバスタチン(LIPITOR)、シンバスタチン(ZOCOR)、KLVFF−(EEX)3、SKF−74652、メシル酸イブタモレン、BACE阻害剤、例えば、ASP−1702、SCH−745966、JNJ−715754、AMG−0683、AZ−12304146、BMS−782450、GSK−188909、NB−533、E2609およびTTP−854;ガンマセクレターゼモジュレーター、例えば、ELND−007;ならびにRAGE(最終糖化産物の受容体)阻害剤、例えばTTP488(Transtech)およびTTP4000(Transtech)、ならびにPTI−777を含む米国特許第7,285,293号に開示されているもの;
(v)アルファ−アドレナリン受容体アゴニスト、例えば、グアンファシン(INTUNIV、TENEX)、クロニジン(CATAPRES)、メタラミノール(ARAMINE)、メチルドパ(ALDOMET、DOPAMET、NOVOMEDOPA)、チザニジン(ZANAFLEX)、フェニレフリン(ネオシネフリンとしても公知である)、メトキサミン、シラゾリン、グアンファシン(INTUNIV)、ロフェキシジン、キシラジン、モダフィニル(PROVIGIL)、アドラフィニル、およびアルモダフィニル(NUVIGIL);
(vi)ベータ−アドレナリン受容体遮断剤(ベータ遮断薬)、例えば、カルテオロール、エスモロール(BREVIBLOC)、ラベタロール(NORMODYNE、TRANDATE)、オクスプレノロール(LARACOR、TRASACOR)、ピンドロール(VISKEN)、プロプラノロール(propanolol)(INDERAL)、ソタロール(BETAPACE、SOTALEX、SOTACOR)、チモロール(BLOCADREN、TIMOPTIC)、アセブトロール(SECTRAL、PRENT)、ナドロール(CORGARD)、酒石酸メトプロロール(LOPRESSOR)、コハク酸メトプロロール(TOPROL−XL)、アテノロール(TENORMIN)、ブトキサミン、およびSR59230A(Sanofi);
(vii)抗コリン薬、例えば、アミトリプチリン(ELAVIL、ENDEP)、ブトリプチリン、メシル酸ベンズトロピン(COGENTIN)、トリヘキシフェニジル(ARTANE)、ジフェンヒドラミン(BENADRYL)、オルフェナドリン(NORFLEX)、ヒヨスチアミン、アトロピン(ATROPEN)、スコポラミン(TRANSDERM−SCOP)、臭化メチルスコポラミン(PARMINE)、ジシクロベリン(BENTYL、BYCLOMINE、DIBENT、DILOMINE)、トルテロジン(DETROL)、オキシブチニン(DITROPAN、LYRINELXL、OXYTROL)、臭化ペンチエネート、プロパンテリン(PRO−BANTHINE)、シクリジン、塩酸イミプラミン(TOFRANIL)、マレイン酸イミプラミン(SURMONTIL)、ロフェプラミン、デシプラミン(NORPRAMIN)、ドキセピン(SINEQUAN、ZONALON)、トリミプラミン(SURMONTIL)、およびグリコピロレート(ROBINUL);
(viii)抗痙攣薬、例えば、カルバマゼピン(TEGRETOL、CARBATROL)、オクスカルバゼピン(TRILEPTAL)、フェニトインナトリウム(PHENYTEK)、ホスフェニトイン(CEREBYX、PRODILANTIN)、ジバルプロエクスナトリウム(DEPAKOTE)、ガバペンチン(NEURONTIN)、プレガバリン(LYRICA)、トピラメート(topirimate)(TOPAMAX)、バルプロ酸(DEPAKENE)、バルプロ酸ナトリウム(DEPACON)、1−ベンジル−5−ブロモウラシル、プロガビド、ベクラミド、ゾニサミド(TRERIEF、EXCEGRAN)、CP−465022、レチガビン、タランパネル、およびプリミドン(MYSOLINE);
(ix)抗精神病薬、例えば、ルラシドン(LATUDA、SM−13496としても公知である;大日本住友製薬株式会社)、アリピプラゾール(ABILIFY)、クロルプロマジン(THORAZINE)、ハロペリドール(HALDOL)、イロペリドン(FANAPTA)、デカン酸フルペンチキソール(DEPIXOL、FLUANXOL)、レセルピン(SERPLAN)、ピモジド(ORAP)、デカン酸フルフェナジン、塩酸フルフェナジン、プロクロルペラジン(COMPRO)、アセナピン(SAPHRIS)、ロキサピン(LOXITANE)、モリンドン(MOBAN)、ペルフェナジン、チオリダジン、チオチキセン(thiothixine)、トリフルオペラジン(STELAZINE)、ラメルテオン、クロザピン(CLOZARIL)、ノルクロザピン(ACP−104)、リスペリドン(RISPERDAL)、パリペリドン(INVEGA)、メルペロン、オランザピン(ZYPREXA)、クエチアピン(SEROQUEL)、タルネタント、アミスルプリド、ジプラシドン(GEODON)、ブロナンセリン(LONASEN)、およびACP−103(Acadia Pharmaceuticals);
(x)カルシウムチャネル遮断薬、例えば、ロメリジン、ジコノチド、ニルバジピン(ESCOR、NIVADIL)、ジペルジピン、アムロジピン(NORVASC、ISTIN、AMLODIN)、フェロジピン(PLENDIL)、ニカルジピン(CARDENE)、ニフェジピン(ADALAT、PROCARDIA)、MEM 1003およびその親化合物ニモジピン(NIMOTOP)、ニソルジピン(SULAR)、ニトレンジピン、ラシジピン(LACIPIL、MOTENS)、レルカニジピン(ZANIDIP)、リファリジン、ジルチアゼム(CARDIZEM)、ベラパミル(CALAN、VERELAN)、AR−R 18565(AstraZeneca)、およびエネカジン;
(xi)カテコールO−メチルトランスフェラーゼ(COMT)阻害剤、例えば、ニテカポン、トルカポン(TASMAR)、エンタカポン(COMTAN)、およびトロポロン;
(xii)中枢神経系刺激薬、例えば、アトモキセチン、レボキセチン、ヨヒンビン、カフェイン、フェンメトラジン、フェンジメトラジン、ペモリン、フェンカムファミン(GLUCOENERGAN、REACTIVAN)、フェネチリン(CAPTAGON)、ピプラドール(MERETRAN)、デアノール(ジメチルアミノエタノールとしても公知である)、メチルフェニデート(DAYTRANA)、塩酸メチルフェニデート(RITALIN)、デクスメチルフェニデート(FOCALIN)、アンフェタミン(単独で、または他のCNS刺激薬、例えば、ADDERALL(アスパラギン酸アンフェタミン、硫酸アンフェタミン、デキストロアンフェタミンサッカレート、および硫酸デキストロアンフェタミン)と組み合わせて)、硫酸デキストロアンフェタミン(DEXEDRINE、DEXTROSTAT)、メタンフェタミン(DESOXYN)、リスデキサンフェタミン(VYVANSE)、およびベンズフェタミン(DIDREX);
(xiii)コルチコステロイド、例えば、プレドニゾン(STERAPRED、DELTASONE)、プレドニゾロン(PRELONE)、酢酸プレドニゾロン(predisolone acetate)(OMNIPRED、PRED MILD、PRED FORTE)、リン酸プレドニゾロンナトリウム(ORAPRED ODT)、メチルプレドニゾロン(MEDROL);酢酸メチルプレドニゾロン(DEPO−MEDROL)、およびコハク酸メチルプレドニゾロンナトリウム(A−METHAPRED、SOLU−MEDROL);
(xiv)ドーパミン受容体アゴニスト、例えば、アポモルヒネ(APOKYN)、ブロモクリプチン(PARLODEL)、カベルゴリン(DOSTINEX)、ジヒドレキシジン、ジヒドロエルゴクリプチン、フェノルドパム(CORLOPAM)、リスリド(DOPERGIN)、テルグリド ペルゴリド(spergolide)(PERMAX)、ピリベジル(TRIVASTAL、TRASTAL)、プラミペキソール(MIRAPEX)、キンピロール、ロピニロール(REQUIP)、ロチゴチン(NEUPRO)、SKF−82958(GlaxoSmithKline)、カリプラジン、パルドプルノクスおよびサリゾタン;
(xv)ドーパミン受容体アンタゴニスト、例えば、クロルプロマジン、フルフェナジン、ハロペリドール、ロキサピン、リスペリドン、チオリダジン、チオチキセン、トリフルオロペラジン、テトラベナジン(NITOMAN、XENAZINE)、7−ヒドロキシアモキサピン、ドロペリドール(INAPSINE、DRIDOL、DROPLETAN)、ドンペリドン(MOTILIUM)、L−741742、L−745870、ラクロプリド、SB−277011A、SCH−23390、エコピパム、SKF−83566、およびメトクロプラミド(REGLAN);
(xvi)ドーパミン再取り込み阻害剤、例えば、ブプロピオン、サフィナミド、マレイン酸ノミフェンシン(MERITAL)、バノキセリン(GBR−12909としても公知である)およびそのデカン酸エステルDBL−583、ならびにアミネプチン;
(xvii)ガンマ−アミノ−酪酸(GABA)受容体アゴニスト、例えば、バクロフェン(LIORESAL、KEMSTRO)、サクロフェン(siclofen)、ペントバルビタール(NEMBUTAL)、プロガビド(GABRENE)、およびクロメチアゾール;
(xviii)ヒスタミン3(H3)アンタゴニスト、例えば、シプロキシファン、チプロリサント(tiprolisant)、S−38093、イルダビサント、ピトリサント、GSK−239512、GSK−207040、JNJ−5207852、JNJ−17216498、HPP−404、SAR−110894、trans−N−エチル−3−フルオロ−3−[3−フルオロ−4−(ピロリジン−1−イルメチル)フェニル]−シクロブタンカルボキサミド(PF−3654746、ならびに米国特許公開第US2005−0043354号、第US2005−0267095号、第US2005−0256135号、第US2008−0096955号、第US2007−1079175号、および第US2008−0176925号;国際特許公開第WO2006/136924号、第WO2007/063385号、第WO2007/069053号、第WO2007/088450号、第WO2007/099423号、第WO2007/105053号、第WO2007/138431号、および第WO2007/088462号;ならびに米国特許第7,115,600号に開示されているもの);
(xix)免疫モジュレーター、例えば、酢酸グラチラマー(コポリマー−1としても公知である;COPAXONE)、MBP−8298(合成ミエリン塩基性タンパク質ペプチド)、フマル酸ジメチル、フィンゴリモド(FTY720としても公知である)、ロキニメクス(LINOMIDE)、ラキニモド(ABR−215062およびSAIK−MSとしても公知である)、ABT−874(ヒト抗IL−12抗体;Abbott)、リツキシマブ(RITUXAN)、アレムツズマブ(CAMPATH)、ダクリズマブ(ZENAPAX)、およびナタリズマブ(TYSABRI);
(xx)免疫抑制薬、例えば、メトトレキセート(TREXALL、RHEUMATREX)、ミトキサントロン(NOVANTRONE)、ミコフェノール酸モフェチル(CELLCEPT)、ミコフェノール酸ナトリウム(MYFORTIC)、アザチオプリン(AZASAN、IMURAN)、メルカプトプリン(PURI−NETHOL)、シクロホスファミド(NEOSAR、CYTOXAN)、クロラムブシル(LEUKERAN)、クラドリビン(LEUSTATIN、MYLINAX)、アルファ−フェトプロテイン、エタネルセプト(ENBREL)、および4−(ベンジルオキシ)−5−[(5−ウンデシル−2H−ピロール−2−イリデン)メチル]−1H,1’H−2,2’−ビピロール(PNU−156804としても公知である);
(xxi)インターフェロンベータ−1a(AVONEX、REBIF)およびインターフェロンベータ−1b(BETASERON、BETAFERON)を含む、インターフェロン;
(xxii)単独か、またはDOPAデカルボキシラーゼ阻害剤(例えば、カルビドパ(SINEMET、CARBILEV、PARCOPA)、ベンセラジド(MADOPAR)、α−メチルドパ、モノフルオロメチルドパ(monofluromethyldopa)、ジフルオロメチルドパ、ブロクレシン、またはm−ヒドロキシベンジルヒドラジン)と組み合わせたレボドパ(または、そのメチルもしくはエチルエステル);
(xxiii)N−メチル−D−アスパラギン酸(NMDA)受容体アンタゴニスト、例えば、メマンチン(NAMENDA、AXURA、EBIXA)、アマンタジン(SYMMETREL)、アカンプロセート(CAMPRAL)、ベソンプロジル、ケタミン(KETALAR)、デルセミン、デキサナビノール、デキセファロキサン、デキストロメトルファン、デキストロルファン、トラキソプロジル、CP−283097、ヒマンタン(himantane)、インダンタドール(idantadol)、イペノキサゾン、L−701252(Merck)、ランシセミン(lancicemine)、レボルファノール(DROMORAN)、LY−233536およびLY−235959(いずれもLilly)、メタドン、(DOLOPHINE)、ネラメキサン、ペルジンホテル、フェンシクリジン、チアネプチン(STABLON)、ジゾシルピン(MK−801としても公知である)、EAB−318(Wyeth)、イボガイン、ボアカンギン、チレタミン、リルゾール(RILUTEK)、アプチガネル(CERES0TAT)、ガベスチネル、およびレマセミド(remacimide);
(xxiv)モノアミンオキシダーゼ(MAO)阻害剤、例えば、セレギリン(EMSAM)、塩酸セレギリン(l−デプレニル、ELDEPRYL、ZELAPAR)、ジメチルセレギリン(dimethylselegilene)、ブロファロミン、フェネルジン(NARDIL)、トラニルシプロミン(PARNATE)、モクロベミド(AURORIX、MANERIX)、ベフロキサトン、サフィナミド、イソカルボキサジド(MARPLAN)、ニアラミド(NIAMID)、ラサギリン(AZILECT)、イプロニアジド(MARSILID、IPROZID、IPRONID)、CHF−3381(Chiesi Farmaceutici)、イプロクロジド、トロキサトン(HUMORYL、PERENUM)、ビフェメラン、デソキシペガニン(desoxypeganine)、ハルミン(テレパチンまたはバナステリン(banasterine)としても公知である)、ハルマリン、リネゾリド(ZYVOX、ZYVOXID)、およびパルギリン(EUDATIN、SUPIRDYL);
(xxv)ムスカリン性受容体(特に、M1サブタイプ)アゴニスト、例えば、セビメリン、レベチラセタム、塩化ベタネコール(DUVOID、URECHOLINE)、イタメリン、ピロカルピン(SALAGEN)、NGX267、アレコリン、L−687306(Merck)、L−689660(Merck)、ヨウ化フルトレトニウム(FURAMON、FURANOL)、ベンゼンスルホン酸フルトレトニウム、p−トルエンスルホン酸フルトレトニウム、McN−A−343、オキソトレモリン、サブコメリン、AC−90222(Acadia Pharmaceuticals)、およびカルバコール(CARBASTAT、MIOSTAT、CARBOPTIC);
(xxvi)神経保護薬、例えば、ボスチニブ、コンドリアーゼ、アリモクロモル(airmoclomol)、ラモトリギン、ペランパネル、アニラセタム、ミナプリン(minaprime)、リルゾール、N−ヒドロキシ−1,2,4,9−テトラヒドロ−3H−カルバゾール−3−イミン、デスモテプラーゼ、アナチバント、アスタキサンチン、神経ペプチドNAP(例えば、AL−108およびAL−208;いずれもAllon Therapeutics)、ニューロストロール(neurostrol)、ペランパネル(perampenel)、イスプロニクリン、ビス(4−β−D−グルコピラノシルオキシベンジル)−2−β−D−グルコピラノシル−2−イソブチルタルトレート(ダクチロリンBまたはDHBとしても公知である)、ホルモバクチン、キサリプロデン(XAPRILA)、ラクタシスチン、塩酸ジメボリン(DIMEBON)、ジスフェントン(CEROVIVE)、アルンジン酸(ONO−2506、PROGLIA、CEREACT)、シチコリン(シチジン5’−ジホスホコリンとしても公知である)、エダラボン(RADICUT)、AEOL−10113およびAEOL−10150(いずれもAeolus Pharmaceuticals)、AGY−94806(SA−450およびMsc−1としても公知である)、顆粒球コロニー刺激因子(AX−200としても公知である)、BAY−38−7271(KN−387271としても公知である;Bayer AG)、アンクロド(VIPRINEX、ARWIN)、DP−b99(D−Pharm Ltd)、HF−0220(17−β−ヒドロキシエピアンドロステロン;Newron Pharmaceuticals)、HF−0420(オリゴトロピン(oligotropin)としても公知である)、ピリドキサール5’−リン酸(MC−1としても公知である)、マイクロプラスミン、S−18986、ピクロゾタン、NP031112、タクロリムス、L−セリル−L−メチオニル−L−アラニル−L−リシル−L−グルタミル−グリシル−L−バリン、AC−184897(Acadia Pharmaceuticals)、ADNF−14(米国国立衛生研究所)、スチルバズレニルニトロン(stilbazulenyl nitrone)、SUN−N8075(第一サントリー生物医学研究所)、ならびにゾナンパネル;
(xxvii)ニコチン性受容体アゴニスト、例えば、エピバチジン、ブプロピオン、CP−601927、バレニクリン、ABT−089(Abbott)、ABT−594、AZD−0328(AstraZeneca)、EVP−6124、R3487(MEM3454としても公知である;Roche/Memory Pharmaceuticals)、R4996(MEM63908としても公知である;Roche/Memory Pharmaceuticals)、TC−4959およびTC−5619(いずれもTargacept)、ならびにRJR−2403;
(xxviii)ノルエピネフリン(ノルアドレナリン)再取り込み阻害剤、例えば、アトモキセチン(STRATTERA)、ドキセピン(APONAL、ADAPIN、SINEQUAN)、ノルトリプチリン(AVENTYL、PAMELOR、NORTRILEN)、アモキサピン(ASENDIN、DEMOLOX、MOXIDIL)、レボキセチン(EDRONAX、VESTRA)、ビロキサジン(VIVALAN)、マプロチリン(DEPRILEPT、LUDIOMIL、PSYMION)、ブプロピオン(WELLBUTRIN)、およびラダキサフィン(radaxafine);
(xxix)(a)PDE1阻害剤(例えば、ビンポセチン(CAVINTON、CERACTIN、INTELECTOL)、および米国特許第6,235,742号に開示されているもの、(b)PDE2阻害剤(例えば、エリスロ−9−(2−ヒドロキシ−3−ノニル)アデニン(EHNA)、BAY 60−7550、および米国特許第6,174,884号に記載されているもの)、(c)PDE3阻害剤(例えば、アナグレリド、シロスタゾール、ミルリノン、オルプリノン、パログレリル、およびピモベンダン)、(d)PDE4阻害剤(例えば、アプレミラスト、イブジラストロフルミラスト(ibudilastroflumilast)、ロリプラム、Ro 20−1724、イブジラスト(KETAS)、ピクラミラスト(RP73401としても公知である)、CDP840、シロミラスト(ARIFLO)、ロフルミラスト、トフィミラスト、オグレミラスト(GRC3886としても公知である)、テトミラスト(OPC−6535としても公知である)、リリミファスト(lirimifast)、テオフィリン(UNIPHYL、THEOLAIR)、アロフィリン(LAS−31025としても公知である)、ドキソフィリン、RPR−122818、またはメセンブリン)、ならびに(e)PDE5阻害剤(例えば、シルデナフィル(VIAGRA、REVATIO)、タダラフィル(CIALIS)、バルデナフィル(LEVITRA、VIVANZA)、ウデナフィル、アバナフィル、ジピリダモール(PERSANTINE)、E−4010、E−4021、E−8010、ザプリナスト、ロデナフィル(iodenafil)、ミロデナフィル、DA−8159、ならびに国際特許出願WO2002/020521、WO2005/049616、WO2006/120552、WO2006/126081、WO2006/126082、WO2006/126083、およびWO2007/122466に開示されているもの)、(f)PDE7阻害剤;(g)PDE8阻害剤;(h)PDE9阻害剤(例えば、BAY 73−6691(Bayer AG)、ならびに米国特許公開第US2003/0195205号、第US2004/0220186号、第US2006/0111372号、第US2006/0106035号、およびUSSN12/118,062(2008年5月9日出願)に開示されているもの)、(i)PDE10阻害剤、例えば2−({4−[1−メチル−4−(ピリジン−4−イル)−1H−ピラゾール−3−イル]フェノキシ}メチル)キノリン−3(4H)−オンおよびSCH−1518291;ならびに(j)PDE11阻害剤を含むがこれらに限定されない、ホスホジエステラーゼ(PDE)阻害剤;
(xxx)キノリン、例えば、キニーネ(その塩酸塩、二塩酸塩、硫酸塩、重硫酸塩およびグルコン酸塩を含む)、クロロキン、ソントキン、ヒドロキシクロロキン(PLAQUENIL)、メフロキン(LARIAM)、およびアモジアキン(CAMOQUIN、FLAVOQUINE);
(xxxi)β−セクレターゼ阻害剤、例えば、ASP−1702、SCH−745966、JNJ−715754、AMG−0683、AZ−12304146、BMS−782450、GSK−188909、NB−533、LY−2886721、E−2609、HPP−854、(+)−酒石酸フェンセリン(POSIPHEN)、LSN−2434074(LY−2434074としても公知である)、KMI−574、SCH−745966、Ac−rER(N2−アセチル−D−アルギニル−L−アルギニン)、ロキシスタチン(E64dとしても公知である)、およびCA074Me;
(xxxii)γ−セクレターゼ阻害剤およびモジュレーター、例えば、BMS−708163(Avagacest)、WO20060430064(Merck)、DSP8658(大日本)、ITI−009、L−685458(Merck)、ELAN−G、ELAN−Z、4−クロロ−N−[(2S)−3−エチル−1−ヒドロキシペンタン−2−イル]ベンゼンスルホンアミド;
(xxxiii)セロトニン(5−ヒドロキシトリプタミン)1A(5−HT1A)受容体アンタゴニスト、例えば、スピペロン、レボ−ピンドロール、BMY7378、NAD−299、S−(−)−UH−301、NAN 190、レコゾタン;
(xxxiv)セロトニン(5−ヒドロキシトリプタミン)2C(5−HT2c)受容体アゴニスト、例えば、バビカセリンおよびジクロナピン;
(xxxv)セロトニン(5−ヒドロキシトリプタミン)4(5−HT4)受容体アゴニスト、例えば、PRX−03140(Epix);
(xxxvi)セロトニン(5−ヒドロキシトリプタミン)6(5−HT6)受容体アンタゴニスト、例えば、A−964324、AVI−101、AVN−211、ミアンセリン(TORVOL、BOLVIDON、NORVAL)、メチオテピン(メチテピンとしても公知である)、リタンセリン、ALX−1161、ALX−1175、MS−245、LY−483518(SGS518としても公知である;Lilly)、MS−245、Ro 04−6790、Ro 43−68544、Ro 63−0563、Ro 65−7199、Ro 65−7674、SB−399885、SB−214111、SB−258510、SB−271046、SB−357134、SB−699929、SB−271046、SB−742457(GlaxoSmithKline)、Lu AE58054(Lundbeck A/S)、およびPRX−07034(Epix);
(xxxvii)セロトニン(5−HT)再取り込み阻害剤、例えば、アラプロクレート、シタロプラム(CELEXA、CIPRAMIL)、エスシタロプラム(LEXAPRO、CIPRALEX)、クロミプラミン(ANAFRANIL)、デュロキセチン(CYMBALTA)、フェモキセチン(MALEXIL)、フェンフルラミン(PONDIMIN)、ノルフェンフルラミン、フルオキセチン(PROZAC)、フルボキサミン(LUVOX)、インダルピン、ミルナシプラン(IXEL)、パロキセチン(PAXIL、SEROXAT)、セルトラリン(ZOLOFT、LUSTRAL)、トラゾドン(DESYREL、MOLIPAXIN)、ベンラファキシン(EFFEXOR)、ジメリジン(NORMUD、ZELMID)、ビシファジン、デスベンラファキシン(PRISTIQ)、ブラソフェンシン、ビラゾドン、カリプラジン、ニューラルステム(neuralstem)およびテソフェンシン;
(xxxviii)栄養因子、例えば、神経成長因子(NGF)、塩基性線維芽細胞成長因子(bFGF;ERSOFERMIN)、ニューロトロフィン−3(NT−3)、カルジオトロフィン−1、脳由来神経栄養因子(BDNF)、ニューブラスチン(neublastin)、メテオリン、およびグリア由来神経栄養因子(GDNF)、ならびに栄養因子の産生を刺激する薬剤、例えば、プロペントフィリン、イデベノン、PYM50028(COGANE;Phytopharm)、およびAIT−082(NEOTROFIN);
(xxxix)グリシン輸送体−1阻害剤、例えば、パリフルチン(paliflutine)、ORG−25935、JNJ−17305600、およびORG−26041;
(xl)AMPA型グルタミン酸受容体モジュレーター、例えば、ペランパネル、ミバンパトル、セルランパネル(selurampanel)、GSK−729327、N−{(3S,4S)−4−[4−(5−シアノチオフェン−2−イル)フェノキシ]テトラヒドロ−フラン−3−イル}プロパン−2−スルホンアミドなど。
(xli)ヤヌスキナーゼ阻害剤(JAK)、例えば、これらに限定されないが、トファシチニブ、ルキソリチニブ、バリシチニブ、CYT387、GLPG0634、レスタウルチニブ、パクリチニブ、およびTG101348。
(xlii)インターロイキン−1受容体関連キナーゼ4阻害剤(IRAK4)、例えば、これに限定されないが、PF−06650833。
一般スキーム
以下では、様々な本発明の化合物の合成を例示する。本発明の範囲内の追加の化合物は、これらの実施例において例示される方法を、単独で、または当技術分野において一般に公知の技術と組み合わせて使用して、調製することができる。
BINAP=1,1’−ビナフタレン−2,2’−ジイルビス(ジフェニルホスファン);Boc=tert−ブトキシカルボニル;br=幅広;n−BuLi=n−ブチルリチウム;CDCl3=重水素化クロロホルム;CD3OD=重水素化メタノール;CF3COOH=トリフルオロ酢酸;CpCo(CO)2=ジカルボニルシクロペンタジエニルコバルト(I);Cs2CO3=炭酸セシウム;d=二重線;dd=二重線の二重線;ddd=二重線の二重線の二重線;cataCXium(登録商標)A=ビス(1−アダマンチル)−ブチルホスファン;ENT−1=第1溶出エナンチオマー;ENT−2=第2溶出エナンチオマー;g=グラム;GCMS=ガスクロマトグラフィー−質量分析;HATU=O−(7−アザベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスフェート;HCl=塩酸;HPLC=高速液体クロマトグラフィー;Hz=ヘルツ;K2CO3=炭酸カリウム;LCMS=液体クロマトグラフィー質量分析;m=多重線;M=モル濃度;mg=ミリグラム;MHz=メガヘルツ;mL=ミリリットル;μL=マイクロリットル;mmol=ミリモル;μmol=マイクロモル;mol=モル;NaH=水素化ナトリウム;NaHCO3=重炭酸ナトリウム;NaOAc=酢酸ナトリウム;NEt3=トリエチルアミン;NH4Cl=塩化アンモニウム;NH2OH・HCl=塩酸ヒドロキシルアミン;NMR=核磁気共鳴;NOE=核オーバーハウザー効果;Pd2(dba)3=トリス(ジベンジリデンアセトン)ジパラジウム(0);Pd(dppf)Cl2=[1,1’−ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(II);Pd(OAc)2=酢酸パラジウム(II);PPh3=トリフェニルホスフィン;psi=ポンド/平方インチ;q=四重線;s=一重線;SPhos Pd G2=クロロ(2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシ−1,1’−ビフェニル)[2−(2’−アミノ−1,1’−ビフェニル)]パラジウム(II);t=三重線;キサントホス=4,5−ビス(ジフェニルホスフィノ)−9,9−ジメチルキサンテン。
調製P1
tert−ブチル5,6,7−トリメチル−4−オキソ−1,3,4,5−テトラヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート(P1)
調製P2
N,6,7−トリメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン−4−アミン、二塩酸塩(P2)
調製P3
6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン−4−アミン、二塩酸塩(P3)
調製P4
4,6,7−トリメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、二塩酸塩(P4)
調製P5
6,7−ジメチル−4−(1−メチル−1H−ピラゾール−4−イル)−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、二塩酸塩(P5)
調製P6
1−(6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン−4−イル)−N,N−ジメチルメタンアミン、三塩酸塩(P6)
調製P7
tert−ブチル4−(ジフルオロメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート(P7)
調製P8
N,1,6,7−テトラメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン−4−アミン、二塩酸塩(P8)
調製P9
6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、塩酸塩(P9)
調製P10
4−メトキシ−6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、ジ(トリフルオロ酢酸)塩(P10)
調製P11
4−(メトキシメチル)−6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、二塩酸塩(P11)
調製P12
4−(ジフルオロメトキシ)−6,7−ジメチル−2,3−ジヒドロ−1H−ピロロ[3,4−c]ピリジン、塩酸塩(P12)
(実施例1)
5,6,7−トリメチル−2−{[1−(ピリジン−3−イル)アゼチジン−3−イル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン(1)
(実施例2)
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(1,2,4−チアジアゾール−5−イル)アゼチジン−3−イル]エタノン(2)
(実施例3)
2−{1−[2−(ジフルオロメトキシ)ピリジン−4−イル]アゼチジン−3−イル}−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン(3)
(実施例4)
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン(4)
(実施例5)
1−(ピリジン−3−イル)アゼチジン−3−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート(5)
(実施例6)
6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン−6−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート(6)
(実施例7、8、および9)
(実施例10および11)
(実施例12)
2−[1−(ピリジン−3−イル)アゼチジン−3−イル]−1−(4,6,7−トリメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)エタノン(12)
生物学的アッセイ
M4 Pam cAMPアッセイ
Claims (26)
- 式(I)の化合物:
[式中、
各R1は、存在する場合、独立して、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、必要に応じて置換されている−O−(C3〜C6)シクロアルキル、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、
aは、0、1、2、および3から選択される整数であり、
各R2は、存在する場合、独立して、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、
bは、0、1、2、3、および4から選択される整数であり、
R3は、存在する場合、独立して、ハロゲン、シアノ、ヒドロキシ、オキソ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、必要に応じて置換されている−O−(C3〜C6)シクロアルキル、必要に応じて置換されている(5〜6員の)ヘテロアリール、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から選択され、但し、R3が、オキソである場合、
cは、0および1から選択される整数であり、
Lは、−(CH2)m−および−O−から選択され、ここで、mは、0、1および2から選択される整数であり、
Aは、存在しないか、または(C3〜C6)シクロアルキルおよび(4〜10員の)ヘテロシクロアルキルからなる群から選択され、ここで、前記シクロアルキルおよびヘテロシクロアルキルはそれぞれ、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、−N(R4)(R5)、−N(R4)(C=(O)(R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から独立して選択される1〜5個の置換基で必要に応じて置換されており、
Eは、(C3〜C12)シクロアルキル、(C6〜C10)アリール、(5〜6員の)ヘテロシクロアルキル、および(5〜10員の)ヘテロアリールから選択され、ここで、前記シクロアルキル、アリール、およびヘテロアリールは、ハロゲン、シアノ、ヒドロキシ、−SF5、ニトロ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C2〜C6)アルケニル、必要に応じて置換されている(C2〜C6)アルキニル、必要に応じて置換されている(C1〜C6)アルキルチオ、必要に応じて置換されている(C1〜C6)アルコキシ、必要に応じて置換されている(C3〜C6)シクロアルキル、メチルオキセタニル、−N(R4)(R5)、−N(R4)(C=(O)R5)、−C(=O)N(R4)(R5)、−O−C(=O)−N(R4)(R5)、−C(=O)−R4、および−C(=O)−OR4からなる群から独立して選択される1〜5個の置換基で必要に応じて置換されており、
R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択されるか、またはR4およびR5は、それらが結合している窒素と一緒になって、必要に応じて置換されている(4〜6員の)ヘテロシクロアルキルを形成する]。 - R1が、必要に応じて置換されている(C1〜C6)アルキルであり、aが、1、2、および3から選択される整数であり、各R2が、存在する場合、必要に応じて置換されている(C1〜C6)アルキルであり、bが、0または1から選択される整数であり、R3が、存在する場合、独立して、オキソ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C1〜C6)アルコキシ、および−N(R4)(R5)からなる群から選択され、但し、R3が、オキソである場合、
- Lが、−(CH2)m−であり、mが、1および2から選択される整数である、請求項1もしくは2に記載の化合物、またはそのN−オキシド、あるいは前記化合物または前記N−オキシドの薬学的に許容される塩。
- Lが、−(CH2)m−であり、mが、1である、請求項1もしくは2に記載の化合物、またはそのN−オキシド、あるいは前記化合物または前記N−オキシドの薬学的に許容される塩。
- Aが、シクロプロピル、シクロブチル、シクロペンチル、およびシクロヘキシルからなる群から選択される(C3〜C8)シクロアルキルであり、ここで、前記シクロアルキルが、ハロゲン、シアノ、−N(R3)(R4)、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から独立して選択される1〜3個の置換基で必要に応じて置換されている、請求項1から4のいずれか一項に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- Aが、シクロプロピルである、請求項5に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- Aが、アゼチジニル、ジヒドロフラニル、ジヒドロチオフェニル、テトラヒドロチオフェニル、テトラヒドロフラニル、テトラヒドロトリアジニル、テトラヒドロピラゾリル、テトラヒドロオキサジニル、テトラヒドロピリミジニル、イミダゾリジニル、ピロリジニル、ピペリジニル、ピペラジニル、オキサゾリジニル、チアゾリジニル、ピラゾリジニル、テトラヒドロピラニル、テトラヒドロチアジニル、テトラヒドロチアジアジニル、テトラヒドロオキサゾリル、オキセタニル、ジオキセタニル、ジオキソラニル、ジオキサニル、オキサジニル、およびオキサチアジニルからなる群から選択される(4〜6員の)ヘテロシクロアルキルであり、ここで、前記ヘテロシクロアルキルが、ハロゲン、シアノ、−N(R3)(R4)、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から独立して選択される1〜3個の置換基で必要に応じて置換されている、請求項1から4のいずれか一項に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- Aが、(4〜6員の)ヘテロ−シクロアルキルであり、前記ヘテロシクロアルキルが、アゼチジニルである、請求項7に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- Eが、トリアゾリル、イミダゾリル、フラニル、イソオキサゾリル、イソチアゾリル、1,2,3−、1,2,4、1,2,5−、または1,3,4−オキサジアゾリル、オキサゾリル、チオフェニル、チアゾリル、チアジアゾリル、イソチアゾリル、ピラゾリル、ピリジニル、ピラジニル、ピリミジニル、ピリダジニル、インドリル、インダゾリル、ベンゾフラニル、ベンゾイミダゾリル、ベンゾチエニル、ベンゾオキサジアゾリル、ベンゾチアゾリル、イソベンゾチオフラニル、ベンゾチオフラニル、ベンゾイソオキサゾリル、ベンゾオキサゾリル、ベンゾジオキソリル、フラノピリジニル、プリニル、イミダゾピリジニル、イミダゾピリミジニル、ピロロピリジニル、ピラゾロピリジニル、ピラゾロピリミジニル、チエノピリジニル、トリアゾロピリミジニル、トリアゾロピリジニル、アントラニリル、キノリニル、イソキノリニル、シンノリニル、キナゾリニル、オキソクロマニル、および1,4−ベンゾオキサジニルからなる群から選択される(5〜10員の)ヘテロアリールであり、ここで、前記ヘテロアリールが、ハロゲン、シアノ、−N(R3)(R4)、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から独立して選択される1〜3個の置換基で必要に応じて置換されている、請求項1から9のいずれか一項に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 前記ヘテロアリールが、チアジアゾリル、ピラゾリル、ピリジニル、ピラジニル、およびピリミジニルからなる群から選択される(5〜6員の)窒素含有ヘテロアリールであり、ここで、前記窒素含有ヘテロアリールが、ハロゲン、シアノ、−N(R3)(R4)、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から独立して選択される1〜3個の置換基で必要に応じて置換されている、請求項9に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 式Iaの化合物:
[式中、
各R1は、存在する場合、独立して、ハロゲン、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から選択され、
aは、1、2および3から選択される整数であり、
R2は、存在する場合、必要に応じて置換されている(C1〜C6)アルキルであり、
bは、0および1から選択される整数であり、
R4およびR5は、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択され、
Eは、(5〜6員の)ヘテロアリールであり、ここで、前記ヘテロアリールは、ハロゲン、シアノ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C1〜C6)アルコキシ、および−N(R4)(R5)からなる群から独立して選択される1〜3個の置換基で必要に応じて置換されており、ここで、R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択される]。 - Eが、ピラゾリル、チアジアゾリル、ピリジニル、およびピリミジニルからなる群から選択される(5〜6員の)窒素含有ヘテロアリールである、請求項11に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 前記(5〜6員の)窒素含有ヘテロアリールが、ピリジニルである、請求項12に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 前記(5〜6員の)窒素含有ヘテロアリールが、ピリミジニルである、請求項12に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 式Ibの化合物:
[式中、
各R1は、存在する場合、独立して、ハロゲン、必要に応じて置換されている(C1〜C6)アルキル、および必要に応じて置換されている(C1〜C6)アルコキシからなる群から選択され、
aは、1、2および3から選択される整数であり、
R2は、存在する場合、必要に応じて置換されている(C1〜C6)アルキルであり、
bは、0および1から選択される整数であり、
R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択され、
Eは、(5〜6員の)ヘテロアリールであり、ここで、前記ヘテロアリールは、ハロゲン、シアノ、ヒドロキシ、必要に応じて置換されている(C1〜C6)アルキル、必要に応じて置換されている(C1〜C6)アルコキシ、および−N(R4)(R5)からなる群から独立して選択される1〜3個の置換基で必要に応じて置換されており、ここで、R4およびR5は、各出現において、それぞれ独立して、水素および必要に応じて置換されている(C1〜C6)アルキルから選択される]。 - Eが、ピラゾリル、チアジアゾリル、ピリジニル、およびピリミジニルからなる群から選択される(5〜6員の)窒素含有ヘテロアリールである、請求項15に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 前記(5〜6員の)窒素含有ヘテロアリールが、ピリミジニルである、請求項16に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 前記(5〜6員の)窒素含有ヘテロアリールが、ピリジニルである、請求項16に記載の化合物、もしくはそのN−オキシド、または前記化合物もしくは前記N−オキシドの薬学的に許容される塩。
- 5,6,7−トリメチル−2−{[1−(ピリジン−3−イル)アゼチジン−3−イル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(1,2,4−チアジアゾール−5−イル)アゼチジン−3−イル]エタノン;
2−{1−[2−(ジフルオロメトキシ)ピリジン−4−イル]アゼチジン−3−イル}−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(ピリジン−3−イル)アゼチジン−3−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート;
6,7−ジヒドロ−5H−シクロペンタ[b]ピリジン−6−イル6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−カルボキシレート;
1−(4−アミノ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−(4−アミノ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリジン−3−イル)シクロプロピル]エタノン;
2−[1−(ピリジン−3−イル)アゼチジン−3−イル]−1−(4,6,7−トリメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)エタノン;
1−[6,7−ジメチル−4−(1−メチル−1H−ピラゾール−4−イル)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−{4−[(ジメチルアミノ)メチル]−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル}−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン;
1−[4−(ジメチルアミノ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジフルオロメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジメチルアミノ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
6,7−ジメチル−2−{[1−(ピリジン−3−イル)アゼチジン−3−イル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−{4−[(シクロプロピルメチル)アミノ]−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル}−2−[1−(ピリミジン−4−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−4−イル)アゼチジン−3−イル]エタノン;
2−(2,3−ジヒドロ−1H−インデン−2−イル)−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
5,6,7−トリメチル−2−({1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}アセチル)−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
5,6,7−トリメチル−2−{[trans−2−(ピリジン−3−イル)シクロプロピル]アセチル}−1,2,3,5−テトラヒドロ−4H−ピロロ[3,4−c]ピリジン−4−オン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリミジン−5−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(ピリミジン−5−イル)シクロプロピル]エタノン;
4−{3−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−オキソプロピル}ベンゾニトリル;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−(4−メトキシフェニル)プロパン−1−オン;
2−[trans−2−(6−クロロピリジン−3−イル)シクロプロピル]−1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(2−メチルピリジン−4−イル)アゼチジン−3−イル]エタノン;
4−(3−{2−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−オキソエチル}アゼチジン−1−イル)ピリジン−2−カルボニトリル;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(1,3,4−チアジアゾール−2−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−3−(1H−ピラゾール−4−イル)プロパン−1−オン;
1−[4−(ジフルオロメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−{1−[2−(ジフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(4−フルオロフェニル)シクロプロピル]エタノン;
2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−メチルピリジン−3−イル)シクロプロピル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−メチルピリジン−3−イル)シクロプロピル]エタノン;
[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル](1−メチル−1H−ピラゾール−4−イル)メタノン;
2−{1−[2−(ジフルオロメトキシ)ピリジン−4−イル]アゼチジン−3−イル}−1−[1,6,7−トリメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(6−フルオロピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(4−メトキシ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−[4−(メトキシメチル)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリジン−3−イル)アゼチジン−3−イル]エタノン;
1−(4−メトキシ−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル)−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[4−(ジフルオロメトキシ)−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[1−(ピリミジン−5−イル)アゼチジン−3−イル]エタノン;
1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−(5−フルオロ−2,3−ジヒドロ−1H−インデン−2−イル)エタノン;
シクロプロピル[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]メタノン;
[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル][(3R)−テトラヒドロフラン−3−イル]メタノン
からなる群から選択される化合物;および
そのN−オキシド、またはその薬学的に許容される塩、もしくは前記N−オキシドの薬学的に許容される塩。 - 1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−[trans−2−(6−フルオロピリジン−3−イル)シクロプロピル]エタノン、もしくはそのN−オキシド、もしくはその薬学的に許容される塩、または前記N−オキシドの薬学的に許容される塩。
- 1−{4−[(シクロプロピルメチル)アミノ]−6,7−ジメチル−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル}−2−[1−(ピリミジン−4−イル)アゼチジン−3−イル]エタノン、もしくはその薬学的に許容される塩、またはN−オキシドの薬学的に許容される塩。
- 1−[6,7−ジメチル−4−(メチルアミノ)−1,3−ジヒドロ−2H−ピロロ[3,4−c]ピリジン−2−イル]−2−{1−[2−(トリフルオロメチル)ピリジン−4−イル]アゼチジン−3−イル}エタノン、もしくはそのN−オキシド、もしくはその薬学的に許容される塩、または前記N−オキシドの薬学的に許容される塩。
- 治療有効量の請求項1から22のいずれか一項に記載の化合物、もしくはN−オキシド、または薬学的に許容される塩、および薬学的に許容される担体を含む医薬組成物。
- 患者におけるM4媒介性の(またはM4関連の)疾患または障害を処置するための方法であって、治療有効量の請求項1から22のいずれか一項に記載の化合物、もしくはN−オキシド、または薬学的に許容される塩を前記患者に投与することを含む、方法。
- 前記M4媒介性の(またはM4関連の)疾患または障害が、アルツハイマー病、統合失調症または精神病、疼痛、嗜癖、睡眠障害、認知障害(例えば軽度認知障害)、パーキンソン病、パーキンソン病レボドパ誘発性ジスキネジア、ハンチントン病、ジスキネジア、口内乾燥、肺高血圧症、慢性閉塞性肺疾患(COPD)、喘息、尿失禁、緑内障、トリソミー21(ダウン症候群)、脳アミロイド血管症、認知症、オランダ型のアミロイドーシスを伴う遺伝性脳出血(HCHWA−D)、クロイツフェルト−ヤコブ病、プリオン障害、筋萎縮性側索硬化症、進行性核上麻痺、頭部外傷、脳卒中、膵炎、封入体筋炎、他の末梢アミロイドーシス、糖尿病、自閉症、およびアテローム性動脈硬化症からなる群から選択される疾患または障害である、請求項24に記載の方法。
- 前記M4媒介性の(またはM4関連の)疾患または障害が、アルツハイマー病、統合失調症、疼痛、嗜癖、および睡眠障害からなる群から選択される疾患または障害である、請求項25に記載の方法。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2767191A (en) * | 1953-12-31 | 1956-10-16 | American Cyanamid Co | Dihydropyrrolo-pyridines |
US3123612A (en) * | 1964-03-03 | Z-acylated z | ||
JP2000109481A (ja) * | 1999-10-13 | 2000-04-18 | Yamanouchi Pharmaceut Co Ltd | キヌクリジン誘導体含有医薬 |
JP2008529982A (ja) * | 2005-02-07 | 2008-08-07 | エフ.ホフマン−ラ ロシュ アーゲー | グリシントランスポーター1の阻害剤としてのヘテロシクリル置換フェニルメタノン |
WO2010124047A1 (en) * | 2009-04-23 | 2010-10-28 | Wyeth Llc | Bisaryl alkynylamides as negative allosteric modulators of metabotropic glutamate receptor 5 (mglur5) |
WO2014035829A1 (en) * | 2012-08-31 | 2014-03-06 | Vanderbilt University | Substituted 3-aminothieno[2,3-c]pyridine-2-carboxamide analogs as positive allosteric modulators |
WO2015027214A1 (en) * | 2013-08-23 | 2015-02-26 | Vanderbilt University | Substituted thieno[2,3-c]pyridazine-6-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
Family Cites Families (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1308461A3 (en) | 1993-01-25 | 2004-02-11 | Takeda Chemical Industries, Ltd. | Antibodies to beta-amyloids or their derivatives and use thereof |
DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
US8173127B2 (en) | 1997-04-09 | 2012-05-08 | Intellect Neurosciences, Inc. | Specific antibodies to amyloid beta peptide, pharmaceutical compositions and methods of use thereof |
EP0994728B1 (en) | 1997-04-09 | 2008-07-30 | Intellect Neurosciences, Inc. | Recombinant antibodies specific for beta-amyloid ends, dna encoding and methods of use thereof |
GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
US6905686B1 (en) | 1997-12-02 | 2005-06-14 | Neuralab Limited | Active immunization for treatment of alzheimer's disease |
TWI239847B (en) | 1997-12-02 | 2005-09-21 | Elan Pharm Inc | N-terminal fragment of Abeta peptide and an adjuvant for preventing and treating amyloidogenic disease |
PL218883B1 (pl) | 2000-02-24 | 2015-02-27 | Lilly Co Eli | Kompozycja farmaceutyczna zawierająca przeciwciało do zastosowania w leczeniu klinicznej lub przedklinicznej choroby Alzheimera |
DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
CA2427661C (en) | 2000-11-03 | 2013-05-28 | Proteotech, Inc. | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
WO2003016466A2 (en) | 2001-08-17 | 2003-02-27 | Eli Lilly And Company | ANTI-Aβ ANTIBODIES |
US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
BR0315157A (pt) | 2002-10-09 | 2005-08-09 | Rinat Neuroscience Corp | Métodos de tratar doença de alzheimer empregando-se anticorpos direcionados contra peptìdeo beta amilóide e composições deste |
US20040220186A1 (en) | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
JP2006527756A (ja) | 2003-06-19 | 2006-12-07 | ファイザー・プロダクツ・インク | Nk1拮抗薬 |
US20070031416A1 (en) | 2003-09-09 | 2007-02-08 | Takeda Pharmaceutical Company Limited | Use of antibody |
GB0327319D0 (en) | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
CA2555071A1 (en) | 2004-02-02 | 2005-09-01 | Pfizer Products Inc. | Histamine-3 receptor modulators |
US7456164B2 (en) | 2004-05-07 | 2008-11-25 | Pfizer, Inc | 3- or 4-monosubtituted phenol and thiophenol derivatives useful as H3 ligands |
EP1595881A1 (en) | 2004-05-12 | 2005-11-16 | Pfizer Limited | Tetrahydronaphthyridine derivates useful as histamine H3 receptor ligands |
EP2298807A3 (en) | 2004-07-30 | 2011-05-18 | Rinat Neuroscience Corp. | Antibodies directed against amyloid-beta peptide and methods using same |
GB0423356D0 (en) | 2004-10-21 | 2004-11-24 | Merck Sharp & Dohme | Therapeutic agents |
DK1807434T3 (da) | 2004-10-25 | 2010-11-22 | Lilly Co Eli | Thienopyridiner som allosteriske potentiatorer af M4- muscarinreceptoren |
US20090074775A1 (en) | 2004-12-22 | 2009-03-19 | David Michael Holtzman | Use Of Anti-AB Antibody To Treat Traumatic Brain Injury |
UY29504A1 (es) | 2005-04-29 | 2006-10-31 | Rinat Neuroscience Corp | Anticuerpos dirigidos contra el péptido amiloide beta y métodos que utilizan los mismos. |
US8227475B2 (en) | 2005-05-12 | 2012-07-24 | Pfizer Inc. | Anhydrous crystalline forms of N-[1-(2-ethoxyethyl)-5-(N-ethyl-N-methylamino)-7-(4-methylpyridin-2-yl-amino)-1H-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
WO2006126083A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3 , 4-b] pyrazinone compounds as pde-5 inhibitors |
WO2006126081A2 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridino [2 , 3-b] pyrazinones as pde-5 inhibitors |
CA2608672A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3,4-b] pyrazinones as pde-5 inhibitors |
US7812040B2 (en) | 2005-06-22 | 2010-10-12 | Pfizer Inc. | Histamine-3 receptor antagonists |
US8158673B2 (en) | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
JP2009514846A (ja) | 2005-11-04 | 2009-04-09 | ファイザー・リミテッド | テトラヒドロナフチリジン誘導体 |
WO2007063385A2 (en) | 2005-12-01 | 2007-06-07 | Pfizer Products Inc. | Spirocyclic amine histamine-3 receptor antagonists |
WO2007069053A1 (en) | 2005-12-14 | 2007-06-21 | Pfizer Products Inc. | Benzimidazole antagonists of the h-3 receptor |
WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
JP2009539762A (ja) | 2006-03-13 | 2009-11-19 | ファイザー・プロダクツ・インク | H3受容体のテトラリン拮抗薬 |
DK2013208T3 (da) | 2006-04-21 | 2011-08-15 | Pfizer Prod Inc | Pyridin[3,4-B]pyrazinoner |
WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
DK2124933T3 (da) | 2007-01-22 | 2012-11-19 | Pfizer Prod Inc | Tosylatsalt af en terapeutisk forbindelse og farmaceutiske sammensætninger deraf |
US8664234B2 (en) | 2010-10-04 | 2014-03-04 | Merck Sharp & Dohme Corp. | Dihydrobenzoquinazolinone M1 receptor positive allosteric modulators |
MX2013005454A (es) | 2010-11-15 | 2013-06-24 | Abbvie Inc | Inhibidores de nampt y rock. |
US9493481B2 (en) | 2012-02-23 | 2016-11-15 | Vanderbilt University | Substituted 5-aminothieno[2,3—C]pyridazine-6-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor M4 |
WO2015027204A1 (en) | 2013-08-23 | 2015-02-26 | Vanderbilt University | Substituted thieno[2,3-b]pyridine-2-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
EP3872078A1 (en) * | 2016-07-01 | 2021-09-01 | Pfizer Inc. | 5,7-dihydro-pyrrolo-pyridine derivatives for use in the treament of depression, anxiety or panic disorders |
GB201616839D0 (en) * | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
-
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3123612A (en) * | 1964-03-03 | Z-acylated z | ||
US2767191A (en) * | 1953-12-31 | 1956-10-16 | American Cyanamid Co | Dihydropyrrolo-pyridines |
JP2000109481A (ja) * | 1999-10-13 | 2000-04-18 | Yamanouchi Pharmaceut Co Ltd | キヌクリジン誘導体含有医薬 |
JP2008529982A (ja) * | 2005-02-07 | 2008-08-07 | エフ.ホフマン−ラ ロシュ アーゲー | グリシントランスポーター1の阻害剤としてのヘテロシクリル置換フェニルメタノン |
WO2010124047A1 (en) * | 2009-04-23 | 2010-10-28 | Wyeth Llc | Bisaryl alkynylamides as negative allosteric modulators of metabotropic glutamate receptor 5 (mglur5) |
WO2014035829A1 (en) * | 2012-08-31 | 2014-03-06 | Vanderbilt University | Substituted 3-aminothieno[2,3-c]pyridine-2-carboxamide analogs as positive allosteric modulators |
WO2015027214A1 (en) * | 2013-08-23 | 2015-02-26 | Vanderbilt University | Substituted thieno[2,3-c]pyridazine-6-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
Non-Patent Citations (4)
Title |
---|
CHIUSOLI, GIAN PAOLO: "Cobalt(0) catalyzed synthesis of N-substituted dihydropyrrolopyridines", TRANSITION METAL CHEMISTRY (DORDRECHT, NETHERLANDS), vol. 14(3),, JPN6022017165, 1989, pages 238 - 40, ISSN: 0004913663 * |
REGISTRY(STN)[ONLINE], JPN7022002061, 2 May 2017 (2017-05-02), ISSN: 0004913664 * |
WILLIAM, B. W. JR.: "THE PREPARATION OF SOME MERIMINE DERIVATIVES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, JPN5020007884, 5 May 1957 (1957-05-05), pages 2199 - 2203, XP055505878, ISSN: 0004913661 * |
XU, FEN: "Eco-friendly synthesis of pyridines via rhodium-catalyzed cyclization of diynes with oximes", GREEN CHEMISTRY, vol. 17(2),, JPN6022017166, 2015, pages 799 - 803, ISSN: 0004913662 * |
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DK3642202T3 (da) | 2023-01-30 |
IL271290A (en) | 2020-01-30 |
IL271290B1 (en) | 2023-07-01 |
KR20200013783A (ko) | 2020-02-07 |
IL271290B2 (en) | 2023-11-01 |
US20200262833A1 (en) | 2020-08-20 |
EP3642202A1 (en) | 2020-04-29 |
EP3642202B1 (en) | 2022-11-02 |
CN110944998B (zh) | 2022-08-16 |
PL3642202T3 (pl) | 2023-03-13 |
TW201920166A (zh) | 2019-06-01 |
MX2019015371A (es) | 2020-07-20 |
CN110944998A (zh) | 2020-03-31 |
PT3642202T (pt) | 2023-02-02 |
SG11201913014YA (en) | 2020-01-30 |
CA3066986A1 (en) | 2018-12-27 |
FI3642202T3 (fi) | 2023-03-01 |
AU2018287787A1 (en) | 2020-01-16 |
US11198692B2 (en) | 2021-12-14 |
ES2937236T3 (es) | 2023-03-27 |
HUE060914T2 (hu) | 2023-04-28 |
BR112019026955A2 (pt) | 2020-06-30 |
JP7263266B2 (ja) | 2023-04-24 |
TWI680128B (zh) | 2019-12-21 |
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