JP2017506237A5 - - Google Patents

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Publication number: JP2017506237A5
Authority: JP; Japan
Prior art keywords: dimethyl; tetrahydropyridin; trifluoro; amino; carboxamide
Prior art date: 2015-02-17
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

JP2016551851A

Other languages

English (en)

Japanese (ja)

Other versions

JP6483146B2 (ja

JP2017506237A (ja

Filing date

2015-02-17

Publication date

2018-03-29

2015-02-17 Application filed filed Critical

2015-02-17 Priority claimed from PCT/EP2015/053327 external-priority patent/WO2015124576A1/en

2017-03-02 Publication of JP2017506237A publication Critical patent/JP2017506237A/ja

2018-03-29 Publication of JP2017506237A5 publication Critical patent/JP2017506237A5/ja

2019-03-13 Application granted granted Critical

2019-03-13 Publication of JP6483146B2 publication Critical patent/JP6483146B2/ja

Status Expired - Fee Related legal-status Critical Current

2035-02-17 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 claims 17
-1 3-((2R, 5S) -6-amino-3,3,5-trifluoro-2,5-dimethyl-2,3,4,5-tetrahydropyridin-2-yl) -4-fluoro Phenyl Chemical group 0.000 claims 8
239000008194 pharmaceutical composition Substances 0.000 claims 4
150000003839 salts Chemical class 0.000 claims 4
208000024827 Alzheimer disease Diseases 0.000 claims 3
OKTQKJMRIBXJQN-ZWKOTPCHSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-fluoropyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1)F)=O)(F)F)(C)F OKTQKJMRIBXJQN-ZWKOTPCHSA-N 0.000 claims 3
HFGDZWAAFQJTRL-ZWKOTPCHSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NC=C(N=C1)OC)(F)F)(C)F HFGDZWAAFQJTRL-ZWKOTPCHSA-N 0.000 claims 3
NHAKNDZGVHHIEX-DLBZAZTESA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-1-(difluoromethyl)pyrazole-3-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NN(C=C1)C(F)F)(F)F)(C)F NHAKNDZGVHHIEX-DLBZAZTESA-N 0.000 claims 2
UFLNEUNQYILWEH-DLBZAZTESA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1N=C(OC1)C)(F)F)(C)F UFLNEUNQYILWEH-DLBZAZTESA-N 0.000 claims 2
OTPYSIDSJNTMOG-ZWKOTPCHSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1)Cl)=O)(F)F)(C)F OTPYSIDSJNTMOG-ZWKOTPCHSA-N 0.000 claims 2
YQEYIBBJTJIMBM-VQTJNVASSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1C)C#N)=O)(F)F)(C)F YQEYIBBJTJIMBM-VQTJNVASSA-N 0.000 claims 2
VCVSZIBVXNPLJH-RBUKOAKNSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1)C#N)=O)(F)F)(C)F VCVSZIBVXNPLJH-RBUKOAKNSA-N 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
PZMYIHWMYVSDEE-JKSUJKDBSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-1,3-thiazole-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1SC=CN1)(F)F)(C)F PZMYIHWMYVSDEE-JKSUJKDBSA-N 0.000 claims 1
ZADSHEURMUBVAC-JKSUJKDBSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-1-methyl-1,2,4-triazole-3-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NN(C=N1)C)(F)F)(C)F ZADSHEURMUBVAC-JKSUJKDBSA-N 0.000 claims 1
ANSIAVPOQGVLFC-ZWKOTPCHSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1N=C(OC1C)C)(F)F)(C)F ANSIAVPOQGVLFC-ZWKOTPCHSA-N 0.000 claims 1
KGWKKESEYVBROW-RBUKOAKNSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-3-fluoro-5-methoxypyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1F)OC)=O)(F)F)(C)F KGWKKESEYVBROW-RBUKOAKNSA-N 0.000 claims 1
SUTNBTCNHDOKDD-JKSUJKDBSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-3-methyl-1,2,4-oxadiazole-5-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NC(=NO1)C)(F)F)(C)F SUTNBTCNHDOKDD-JKSUJKDBSA-N 0.000 claims 1
HOESHHMMCCAKCR-DLBZAZTESA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-4-bromo-1-methylimidazole-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1N(C=C(N1)Br)C)(F)F)(C)F HOESHHMMCCAKCR-DLBZAZTESA-N 0.000 claims 1
JOQPMLZUFXKUND-DLBZAZTESA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-4-methyl-1,3-thiazole-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1SC=C(N1)C)(F)F)(C)F JOQPMLZUFXKUND-DLBZAZTESA-N 0.000 claims 1
JZWNILHOEJVHHZ-RBUKOAKNSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-fluoro-3-methylpyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1C)F)=O)(F)F)(C)F JZWNILHOEJVHHZ-RBUKOAKNSA-N 0.000 claims 1
QIJVGCAOVFBXFY-RBUKOAKNSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-methoxy-3-methylpyrazine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NC=C(N=C1C)OC)(F)F)(C)F QIJVGCAOVFBXFY-RBUKOAKNSA-N 0.000 claims 1
YWLRPFXPTFLZDK-RBUKOAKNSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-methoxypyridine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(C1=NC=C(C=C1)OC)=O)(F)F)(C)F YWLRPFXPTFLZDK-RBUKOAKNSA-N 0.000 claims 1
RFYVGRKMWIRDAM-ZWKOTPCHSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-methoxypyrimidine-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C1=NC=C(C=N1)OC)(F)F)(C)F RFYVGRKMWIRDAM-ZWKOTPCHSA-N 0.000 claims 1
ZXEUQJAXUTWMOI-JKSUJKDBSA-N N-[3-[(2R,5S)-6-amino-3,3,5-trifluoro-2,5-dimethyl-4H-pyridin-2-yl]-4-fluorophenyl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound NC=1[C@@](CC([C@@](N1)(C)C=1C=C(C=CC1F)NC(=O)C=1OC(=NN1)C)(F)F)(C)F ZXEUQJAXUTWMOI-JKSUJKDBSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000003838 furazanyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
125000001786 isothiazolyl group Chemical group 0.000 claims 1
125000000842 isoxazolyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1

JP2016551851A 2014-02-19 2015-02-17 アルツハイマー病治療用のｂａｃｅ１阻害剤としての２−アミノ−３，５，５−トリフルオロ−３，４，５，６−テトラヒドロピリジン Expired - Fee Related JP6483146B2 (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DKPA201400086		2014-02-19
DKPA201400086		2014-02-19
DKPA201400349		2014-07-01
DKPA201400349		2014-07-01
PCT/EP2015/053327 WO2015124576A1 (en)	2014-02-19	2015-02-17	2-amino-3, 5, 5-trifluoro-3, 4, 5, 6-tetrahydropyridines as bace1 inhibitors for treatment of alzheimer's disease

Publications (3)

Publication Number	Publication Date
JP2017506237A JP2017506237A (ja)	2017-03-02
JP2017506237A5 true JP2017506237A5 (2)	2018-03-29
JP6483146B2 JP6483146B2 (ja)	2019-03-13

Family

ID=59009438

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2016551851A Expired - Fee Related JP6483146B2 (ja)	2014-02-19	2015-02-17	アルツハイマー病治療用のｂａｃｅ１阻害剤としての２−アミノ−３，５，５−トリフルオロ−３，４，５，６−テトラヒドロピリジン

Country Status (25)

Country	Link
US (2)	US20170066741A1 (2)
EP (1)	EP3107897A1 (2)
JP (1)	JP6483146B2 (2)
KR (1)	KR20160115936A (2)
CN (1)	CN106029639B (2)
AP (1)	AP2016009370A0 (2)
AR (1)	AR099489A1 (2)
AU (1)	AU2015220873A1 (2)
CA (1)	CA2940028A1 (2)
CL (1)	CL2016002072A1 (2)
CR (1)	CR20160352A (2)
DO (1)	DOP2016000194A (2)
EA (1)	EA031132B1 (2)
EC (1)	ECSP16072941A (2)
GE (2)	GEAP201814248A (2)
IL (1)	IL246875A0 (2)
MA (1)	MA39225A1 (2)
MX (1)	MX2016010777A (2)
PE (1)	PE20161225A1 (2)
PH (1)	PH12016501600A1 (2)
RU (1)	RU2016133626A (2)
SG (1)	SG11201606812WA (2)
TW (1)	TW201609700A (2)
UA (1)	UA117695C2 (2)
WO (1)	WO2015124576A1 (2)

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JO3458B1 (ar)	2014-11-10	2020-07-05	H Lundbeck As	2- أمينو-6- (دايفلوروميثيل) – 5، 5- ديفلورو-6-فينيل-3،4، 5، 6-تيتراهيدروبيريدين كمثبطات bace1
MA40941A (fr) *	2014-11-10	2017-09-19	H Lundbeck As	2-amino-5,5-difluoro-6-(fluorométhyl)-6-phényl-3,4,5,6-tétrahydropyridines comme inhibiteurs de bace1
CR20170187A (es) *	2014-11-10	2018-02-01	H Lundbeck As	2-Amino-3,5-difluoro-6-metil-6-fenil-3,4,5,6-tetrahidropiridinas en calidad de inhibidores de BACE1 para el tratamiento de la enfermedad de Alzheimer
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WO2018078042A1 (en)	2016-10-28	2018-05-03	H. Lundbeck A/S	Combination treatments comprising administration of imidazopyrazinones
BR112018017058A2 (pt)	2016-12-21	2019-07-02	H Lundbeck As	6-amino-5-fluoro-5-(fluorometil)-2,3,4,5-tetra-hidropiridin-2-il-fenil-5-(metóxi-d3)-pirazina-2-carboxamidas e derivados fluorados do mesmo como inibidores de bace1
BR112020006677A2 (pt)	2017-10-05	2020-10-06	Fulcrum Therapeutics, Inc.	uso de inibidores p38 para reduzir a expressão de dux4
US10342786B2 (en)	2017-10-05	2019-07-09	Fulcrum Therapeutics, Inc.	P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD
EP3723807B1 (en)	2017-12-14	2021-10-20	H. Lundbeck A/S	Combination treatments comprising administration of 1h-pyrazolo[4,3-b]pyridines
AR113926A1 (es)	2017-12-14	2020-07-01	H Lundbeck As	Derivados de 1h-pirazolo[4,3-b]piridinas
WO2019121840A1 (en)	2017-12-20	2019-06-27	H. Lundbeck A/S	Pyrazolo[3,4-b]pyridines and imidazo[1,5-b]pyridazines as pde1 inhibitors
KR102507861B1 (ko)	2018-04-19	2023-03-09	삼성에스디에스 주식회사	부채널 공격에 안전한 연산 장치 및 방법
KR102510077B1 (ko)	2018-04-24	2023-03-14	삼성에스디에스 주식회사	부채널 공격에 안전한 연산 장치 및 방법
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TW201623295A (zh)	2014-04-11	2016-07-01	塩野義製藥股份有限公司	具有ｂａｃｅ１抑制活性之二氫噻及二氫衍生物

2015
- 2015-02-17 KR KR1020167021930A patent/KR20160115936A/ko not_active Withdrawn
- 2015-02-17 CR CR20160352A patent/CR20160352A/es unknown
- 2015-02-17 GE GEAP201814248A patent/GEAP201814248A/en unknown
- 2015-02-17 RU RU2016133626A patent/RU2016133626A/ru not_active Application Discontinuation
- 2015-02-17 AU AU2015220873A patent/AU2015220873A1/en not_active Abandoned
- 2015-02-17 CA CA2940028A patent/CA2940028A1/en not_active Abandoned
- 2015-02-17 UA UAA201608414A patent/UA117695C2/uk unknown
- 2015-02-17 WO PCT/EP2015/053327 patent/WO2015124576A1/en not_active Ceased
- 2015-02-17 MX MX2016010777A patent/MX2016010777A/es unknown
- 2015-02-17 PE PE2016001299A patent/PE20161225A1/es not_active Application Discontinuation
- 2015-02-17 MA MA39225A patent/MA39225A1/fr unknown
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