JP2017523223A5 - - Google Patents

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Publication number: JP2017523223A5
Authority: JP; Japan
Prior art keywords: amino; methyl; azabicyclo; thia; hept
Prior art date: 2015-08-05
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

Application number

JP2017506879A

Other languages

English (en)

Japanese (ja)

Other versions

JP6576433B2 (ja

JP2017523223A (ja

Filing date

2015-08-05

Publication date

2018-09-13

2015-08-05 Application filed filed Critical

2015-08-05 Priority claimed from PCT/US2015/043868 external-priority patent/WO2016022724A1/en

2017-08-17 Publication of JP2017523223A publication Critical patent/JP2017523223A/ja

2018-09-13 Publication of JP2017523223A5 publication Critical patent/JP2017523223A5/ja

2019-09-18 Application granted granted Critical

2019-09-18 Publication of JP6576433B2 publication Critical patent/JP6576433B2/ja

Status Active legal-status Critical Current

2035-08-05 Anticipated expiration legal-status Critical

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-1 2 - pyrrolidinonyl Chemical group 0.000 claims 203
229910052731 fluorine Inorganic materials 0.000 claims 78
150000001875 compounds Chemical class 0.000 claims 77
150000003839 salts Chemical class 0.000 claims 73
229910052739 hydrogen Inorganic materials 0.000 claims 50
229910052801 chlorine Inorganic materials 0.000 claims 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
125000005842 heteroatom Chemical group 0.000 claims 30
125000001424 substituent group Chemical group 0.000 claims 30
125000000842 isoxazolyl group Chemical group 0.000 claims 28
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 26
125000000719 pyrrolidinyl group Chemical group 0.000 claims 24
229910052760 oxygen Inorganic materials 0.000 claims 23
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 22
229910052717 sulfur Inorganic materials 0.000 claims 22
125000001188 haloalkyl group Chemical group 0.000 claims 19
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 18
125000003226 pyrazolyl group Chemical group 0.000 claims 18
125000000335 thiazolyl group Chemical group 0.000 claims 17
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 16
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 16
125000002950 monocyclic group Chemical group 0.000 claims 16
125000002757 morpholinyl group Chemical group 0.000 claims 16
125000000168 pyrrolyl group Chemical group 0.000 claims 16
125000000217 alkyl group Chemical group 0.000 claims 15
125000002619 bicyclic group Chemical group 0.000 claims 14
125000002971 oxazolyl group Chemical group 0.000 claims 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
125000005843 halogen group Chemical group 0.000 claims 12
125000001072 heteroaryl group Chemical group 0.000 claims 12
229910052757 nitrogen Inorganic materials 0.000 claims 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
229910052799 carbon Inorganic materials 0.000 claims 10
125000001786 isothiazolyl group Chemical group 0.000 claims 10
125000004076 pyridyl group Chemical group 0.000 claims 10
125000001544 thienyl group Chemical group 0.000 claims 10
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 9
QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 claims 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 9
125000001113 thiadiazolyl group Chemical group 0.000 claims 9
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 8
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 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 8
125000002541 furyl group Chemical group 0.000 claims 8
125000004043 oxo group Chemical group O=* 0.000 claims 8
239000012453 solvate Substances 0.000 claims 8
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 8
125000004432 carbon atom Chemical group C* 0.000 claims 7
125000000623 heterocyclic group Chemical group 0.000 claims 7
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 6
101150065749 Churc1 gene Proteins 0.000 claims 6
102100038239 Protein Churchill Human genes 0.000 claims 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
239000008194 pharmaceutical composition Substances 0.000 claims 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
125000003545 alkoxy group Chemical group 0.000 claims 5
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 5
SQXPNCGBFIIPNW-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine-7-carbonitrile Chemical compound C1=NC=NC2=CC(C#N)=CN=C21 SQXPNCGBFIIPNW-UHFFFAOYSA-N 0.000 claims 5
YVOLUPPVPQLTHT-UHFFFAOYSA-N pyrido[3,4-b]pyrazin-5-amine Chemical compound C1=CN=C2C(N)=NC=CC2=N1 YVOLUPPVPQLTHT-UHFFFAOYSA-N 0.000 claims 5
206010012289 Dementia Diseases 0.000 claims 4
239000003814 drug Substances 0.000 claims 4
125000001153 fluoro group Chemical group F* 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
238000000034 method Methods 0.000 claims 4
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 3
150000001412 amines Chemical class 0.000 claims 3
125000004438 haloalkoxy group Chemical group 0.000 claims 3
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 3
229960005206 pyrazinamide Drugs 0.000 claims 3
125000000714 pyrimidinyl group Chemical group 0.000 claims 3
229920006395 saturated elastomer Polymers 0.000 claims 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
208000024827 Alzheimer disease Diseases 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
QTSOETUMHLSGRH-RHXQLXPWSA-N NC=1S[C@H]2C[C@H]2[C@@](N=1)(CF)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(C=C1)Cl Chemical compound NC=1S[C@H]2C[C@H]2[C@@](N=1)(CF)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(C=C1)Cl QTSOETUMHLSGRH-RHXQLXPWSA-N 0.000 claims 2
KUVMNGMSFSUKLZ-JFXOYSPCSA-N NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(N=C1C)O[C@H](C#C)C)C(F)F Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(N=C1C)O[C@H](C#C)C)C(F)F KUVMNGMSFSUKLZ-JFXOYSPCSA-N 0.000 claims 2
LRZKDOOBZWCORJ-XJWKGHCWSA-N NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=CC=1F)NC(=O)C1=NC=C(N=C1)O[C@@H](C(F)(F)F)C)COC Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=CC=1F)NC(=O)C1=NC=C(N=C1)O[C@@H](C(F)(F)F)C)COC LRZKDOOBZWCORJ-XJWKGHCWSA-N 0.000 claims 2
LRZKDOOBZWCORJ-IJNWCYAXSA-N NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=CC=1F)NC(=O)C1=NC=C(N=C1)O[C@H](C(F)(F)F)C)COC Chemical compound NC=1S[C@]2(C[C@H]2[C@@](N=1)(C)C=1C=C(C=CC=1F)NC(=O)C1=NC=C(N=C1)O[C@H](C(F)(F)F)C)COC LRZKDOOBZWCORJ-IJNWCYAXSA-N 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
208000010877 cognitive disease Diseases 0.000 claims 2
229940125810 compound 20 Drugs 0.000 claims 2
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 2
125000003373 pyrazinyl group Chemical group 0.000 claims 2
125000002098 pyridazinyl group Chemical group 0.000 claims 2
125000005309 thioalkoxy group Chemical group 0.000 claims 2
HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
QZINTEQDGINVJU-UHFFFAOYSA-N 3-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1OCC(F)(F)F QZINTEQDGINVJU-UHFFFAOYSA-N 0.000 claims 1
OOLVBHNAPKNWGY-JJEOQYAHSA-N C(C)(=O)NC[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(N=C1)OCC#C)N Chemical compound C(C)(=O)NC[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(N=C1)OCC#C)N OOLVBHNAPKNWGY-JJEOQYAHSA-N 0.000 claims 1
RUQLSEGGGPIPBT-CWFSZBLJSA-N C(C)(=O)[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(C=C1)Cl)N Chemical compound C(C)(=O)[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC(=O)C1=NC=C(C=C1)Cl)N RUQLSEGGGPIPBT-CWFSZBLJSA-N 0.000 claims 1
AEYMSQMOHGXPCW-KNXBSLHKSA-N C(C)(=O)[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC=1C2=C(N=CN=1)C=C(C=N2)C#N)N Chemical compound C(C)(=O)[C@]12SC(=N[C@]([C@@H]2C1)(C)C=1C=C(C=C(C=1F)F)NC=1C2=C(N=CN=1)C=C(C=N2)C#N)N AEYMSQMOHGXPCW-KNXBSLHKSA-N 0.000 claims 1
ZBYWTFOTGUDFGK-PWIZWCRZSA-N C[C@]([C@@H]12)(C(C=C(C=C3)C4=CC(OCC(C(F)F)(F)F)=CN=C4C(N)=O)=C3F)N=C(N)S[C@@]1(CO)C2(F)F Chemical compound C[C@]([C@@H]12)(C(C=C(C=C3)C4=CC(OCC(C(F)F)(F)F)=CN=C4C(N)=O)=C3F)N=C(N)S[C@@]1(CO)C2(F)F ZBYWTFOTGUDFGK-PWIZWCRZSA-N 0.000 claims 1
YFTMTZTZEITNRM-PBNUPURSSA-N C[C@]([C@@H]1C2)(C(C=C(C=C3F)C4=C(C)C(C(N)=O)=NC=C4OCC#C)=C3F)N=C(N)S[C@]12C#N Chemical compound C[C@]([C@@H]1C2)(C(C=C(C=C3F)C4=C(C)C(C(N)=O)=NC=C4OCC#C)=C3F)N=C(N)S[C@]12C#N YFTMTZTZEITNRM-PBNUPURSSA-N 0.000 claims 1
WRUWFNGUSFPAPF-CSKMKTBNSA-N C[C@]1(C(C=C(C=C2F)C(C(OCC3=NC=CO3)=NC3=C(N)N=C4)=CC3=C4F)=C2F)N=C(N)S[C@]2(C(F)F)[C@H]1C2 Chemical compound C[C@]1(C(C=C(C=C2F)C(C(OCC3=NC=CO3)=NC3=C(N)N=C4)=CC3=C4F)=C2F)N=C(N)S[C@]2(C(F)F)[C@H]1C2 WRUWFNGUSFPAPF-CSKMKTBNSA-N 0.000 claims 1
CPQAZISYEYFMSH-RQUSPXKASA-N C[C@]1(C(C=C(C=C2F)C3=CC(Cl)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(C(F)F)[C@H]1C2 Chemical compound C[C@]1(C(C=C(C=C2F)C3=CC(Cl)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(C(F)F)[C@H]1C2 CPQAZISYEYFMSH-RQUSPXKASA-N 0.000 claims 1
KLAABILILJWVBD-ITEAAPOESA-N C[C@]1(C(C=C(C=C2F)C3=CC(OCC(C(F)F)(F)F)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(COC)[C@H]1C2 Chemical compound C[C@]1(C(C=C(C=C2F)C3=CC(OCC(C(F)F)(F)F)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(COC)[C@H]1C2 KLAABILILJWVBD-ITEAAPOESA-N 0.000 claims 1
AGHFFVZKKJPCHR-IWMITWMQSA-N C[C@]1(C(C=C(C=C2F)C3=CC(OCC(F)(F)F)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(COC)[C@H]1C2 Chemical compound C[C@]1(C(C=C(C=C2F)C3=CC(OCC(F)(F)F)=CN=C3C(N)=O)=C2F)N=C(N)S[C@]2(COC)[C@H]1C2 AGHFFVZKKJPCHR-IWMITWMQSA-N 0.000 claims 1
GFZREIKTOSNKIC-MGOULQTBSA-N C[C@]1(C(C=C(C=N2)C(N=C3C(N)=NC=CC3=N3)=C3OCC#C)=C2F)N=C(N)S[C@@H]2[C@H]1C2 Chemical compound C[C@]1(C(C=C(C=N2)C(N=C3C(N)=NC=CC3=N3)=C3OCC#C)=C2F)N=C(N)S[C@@H]2[C@H]1C2 GFZREIKTOSNKIC-MGOULQTBSA-N 0.000 claims 1
208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
208000028698 Cognitive impairment Diseases 0.000 claims 1
229940126062 Compound A Drugs 0.000 claims 1
201000010374 Down Syndrome Diseases 0.000 claims 1
XDBRMTANKYLCMG-NAKSJZFLSA-N FC1=C(C=C(C=C1F)NC1=NC=CC=2C1=NC=C(N=2)OCC=1OC=CN=1)[C@]1(N=C(S[C@]2(C[C@@H]12)S(=O)(=O)C)N)C Chemical compound FC1=C(C=C(C=C1F)NC1=NC=CC=2C1=NC=C(N=2)OCC=1OC=CN=1)[C@]1(N=C(S[C@]2(C[C@@H]12)S(=O)(=O)C)N)C XDBRMTANKYLCMG-NAKSJZFLSA-N 0.000 claims 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
108010061951 Methemoglobin Proteins 0.000 claims 1
CJLSORNLGQFZEI-RVHYNSKXSA-N NC(C(C(C(C=C1)=CC([C@](CF)([C@@H]2C3)N=C(N)S[C@]23C2=CN=CO2)=C1F)=C1)=NC=C1Cl)=O Chemical compound NC(C(C(C(C=C1)=CC([C@](CF)([C@@H]2C3)N=C(N)S[C@]23C2=CN=CO2)=C1F)=C1)=NC=C1Cl)=O CJLSORNLGQFZEI-RVHYNSKXSA-N 0.000 claims 1
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KSJCZJIRZMJPDM-BMQQJOASSA-N NC1=N[C@]([C@@H]2C[C@@]2(C1)[C@@H](C)O)(C)C=1C=C(C=C(C=1F)F)NC=1C2=C(N=CN=1)C=C(C=N2)C#N Chemical compound NC1=N[C@]([C@@H]2C[C@@]2(C1)[C@@H](C)O)(C)C=1C=C(C=C(C=1F)F)NC=1C2=C(N=CN=1)C=C(C=N2)C#N KSJCZJIRZMJPDM-BMQQJOASSA-N 0.000 claims 1
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JP2017506879A 2014-08-08 2015-08-05 β−セクレターゼ阻害剤としてのシクロプロピル縮合チアジン−２−アミン化合物及び使用方法 Active JP6576433B2 (ja)

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2015
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- 2015-08-05 CA CA2957544A patent/CA2957544C/en active Active
- 2015-08-05 US US14/819,256 patent/US9550762B2/en active Active
- 2015-08-05 MX MX2017001794A patent/MX381482B/es unknown
- 2015-08-05 WO PCT/US2015/043868 patent/WO2016022724A1/en not_active Ceased
- 2015-08-05 JP JP2017506879A patent/JP6576433B2/ja active Active
- 2015-08-05 AU AU2015301028A patent/AU2015301028B2/en active Active
- 2015-08-05 EP EP15766951.6A patent/EP3177618A1/en not_active Withdrawn
- 2015-08-07 UY UY0001036263A patent/UY36263A/es not_active Application Discontinuation
- 2015-08-07 AR ARP150102557A patent/AR101483A1/es unknown
- 2015-08-07 TW TW104125848A patent/TWI614250B/zh active
- 2015-08-09 JO JOP/2015/0190A patent/JO3569B1/ar active
2016
- 2016-11-17 US US15/354,877 patent/US20170267673A1/en not_active Abandoned

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