JP2014522855A5 - - Google Patents

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Publication number: JP2014522855A5
Authority: JP; Japan
Prior art keywords: piperidin; oxo; benzoyl; pyrrolidin; methoxy
Prior art date: 2012-07-13
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

JP2014519688A

Other languages

English (en)

Japanese (ja)

Other versions

JP5957077B2 (ja

JP2014522855A (ja

Filing date

2012-07-13

Publication date

2015-08-06

2012-07-13 Application filed filed Critical

2012-07-13 Priority claimed from PCT/IB2012/053613 external-priority patent/WO2013008217A1/en

2014-09-08 Publication of JP2014522855A publication Critical patent/JP2014522855A/ja

2015-08-06 Publication of JP2014522855A5 publication Critical patent/JP2014522855A5/ja

2016-07-27 Application granted granted Critical

2016-07-27 Publication of JP5957077B2 publication Critical patent/JP5957077B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-07-13 Anticipated expiration legal-status Critical

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150000003839 salts Chemical class 0.000 claims 20
150000001875 compounds Chemical class 0.000 claims 19
125000003545 alkoxy group Chemical group 0.000 claims 8
125000000217 alkyl group Chemical group 0.000 claims 8
125000005843 halogen group Chemical group 0.000 claims 7
125000001424 substituent group Chemical group 0.000 claims 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 5
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims 4
-1 3- (4- (4-methoxybenzoyl) piperidin-1-yl) -2-oxopyrrolidin-1-yl Chemical group 0.000 claims 3
229910052799 carbon Inorganic materials 0.000 claims 3
125000001072 heteroaryl group Chemical group 0.000 claims 3
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical group CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
FMURKSCWRQGCFO-OAQYLSRUSA-N 2-[[(3r)-3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CC[C@H]1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-OAQYLSRUSA-N 0.000 claims 1
DDIZJESACWEABB-HXUWFJFHSA-N 2-[[(3r)-3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-HXUWFJFHSA-N 0.000 claims 1
BVCFVQGPDDYTEY-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 BVCFVQGPDDYTEY-OAQYLSRUSA-N 0.000 claims 1
DUCZLEBAUSAZOC-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 DUCZLEBAUSAZOC-OAQYLSRUSA-N 0.000 claims 1
QWYIBGOLIBASGM-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-OAQYLSRUSA-N 0.000 claims 1
FMURKSCWRQGCFO-NRFANRHFSA-N 2-[[(3s)-3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CC[C@@H]1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-NRFANRHFSA-N 0.000 claims 1
DDIZJESACWEABB-FQEVSTJZSA-N 2-[[(3s)-3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-FQEVSTJZSA-N 0.000 claims 1
FMURKSCWRQGCFO-UHFFFAOYSA-N 2-[[3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CCC1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-UHFFFAOYSA-N 0.000 claims 1
LJLQEWDFIMKBSL-UHFFFAOYSA-N 2-[[3-[4-(4-chlorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 LJLQEWDFIMKBSL-UHFFFAOYSA-N 0.000 claims 1
DDIZJESACWEABB-UHFFFAOYSA-N 2-[[3-[4-(4-fluorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 DDIZJESACWEABB-UHFFFAOYSA-N 0.000 claims 1
QOUNQNYSBYTMLY-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopiperidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CCC2)=O)CC1 QOUNQNYSBYTMLY-UHFFFAOYSA-N 0.000 claims 1
QWYIBGOLIBASGM-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-UHFFFAOYSA-N 0.000 claims 1
ZGPMZIHTBVGHFX-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C=CN=3)CC2)=O)CC1 ZGPMZIHTBVGHFX-UHFFFAOYSA-N 0.000 claims 1
ZOLNILZRLCDHDN-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-4a,7a-dihydro-3h-thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4SC=CC4N=3)CC2)=O)CC1 ZOLNILZRLCDHDN-UHFFFAOYSA-N 0.000 claims 1
HTWNXILBIKZTTF-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(C)=C(C)C(=O)N=3)CC2)=O)CC1 HTWNXILBIKZTTF-UHFFFAOYSA-N 0.000 claims 1
VNXUSDDWRYWPQI-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-5-methyl-1h-pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C(C)=CN=3)CC2)=O)CC1 VNXUSDDWRYWPQI-UHFFFAOYSA-N 0.000 claims 1
TVSSLHKEVCLVAI-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-6-methyl-1h-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(C)=CC(=O)N=3)CC2)=O)CC1 TVSSLHKEVCLVAI-UHFFFAOYSA-N 0.000 claims 1
DVIHZULFCIMZGZ-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-6-methyl-4a,7a-dihydro-3h-thieno[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C=C(C)SC4N=3)CC2)=O)CC1 DVIHZULFCIMZGZ-UHFFFAOYSA-N 0.000 claims 1
PERWUJINIMBCAY-UHFFFAOYSA-N 2-chloro-5-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C=C(C(Cl)=CC=3)C#N)CC2)=O)CC1 PERWUJINIMBCAY-UHFFFAOYSA-N 0.000 claims 1
OXTYNMCLCNPCJW-UHFFFAOYSA-N 2-chloro-6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C(=C(Cl)C=CC=3)C#N)CC2)=O)CC1 OXTYNMCLCNPCJW-UHFFFAOYSA-N 0.000 claims 1
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims 1
125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
BHLYXUCYNUOODH-UHFFFAOYSA-N 6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1-methyl-5,7a-dihydro-3ah-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C(N(N=C4)C)N=3)CC2)=O)CC1 BHLYXUCYNUOODH-UHFFFAOYSA-N 0.000 claims 1
DEGIMKQHUITSSN-UHFFFAOYSA-N 6-ethyl-2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-pyrimidin-4-one Chemical compound N1C(CC)=CC(=O)N=C1CN1C(=O)C(N2CCC(CC2)C(=O)C=2C=CC(OC)=CC=2)CC1 DEGIMKQHUITSSN-UHFFFAOYSA-N 0.000 claims 1
LWZRQSRLJJMSHR-UHFFFAOYSA-N COC1=CC=C(C=C1)C(=O)C2CCN(CC2)C3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 Chemical compound COC1=CC=C(C=C1)C(=O)C2CCN(CC2)C3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 LWZRQSRLJJMSHR-UHFFFAOYSA-N 0.000 claims 1
LWZRQSRLJJMSHR-HCSIYLKJSA-N COC1=CC=C(C=C1)C(=O)C2CCN(CC2)[C@@H]3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 Chemical compound COC1=CC=C(C=C1)C(=O)C2CCN(CC2)[C@@H]3CCN(C3=O)CC4CC5CCCCC(=O)C5N4 LWZRQSRLJJMSHR-HCSIYLKJSA-N 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
JDZOLLKCZDHXOE-UHFFFAOYSA-N n-(3,4-dihydro-2h-pyrano[2,3-d]pyridazin-5-yl)-2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3C=4CCCOC=4C=NN=3)CC2)=O)CC1 JDZOLLKCZDHXOE-UHFFFAOYSA-N 0.000 claims 1
PADREXIRIZBNMQ-GOSISDBHSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-GOSISDBHSA-N 0.000 claims 1
PADREXIRIZBNMQ-SFHVURJKSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[(3s)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-SFHVURJKSA-N 0.000 claims 1
PADREXIRIZBNMQ-UHFFFAOYSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
YUBFIWOTPFWWDX-UHFFFAOYSA-N pyrano[4,3-d]pyrimidin-4-one Chemical compound C1=COC=C2C(=O)N=CN=C21 YUBFIWOTPFWWDX-UHFFFAOYSA-N 0.000 claims 1

JP2014519688A 2011-07-13 2012-07-13 タンキラーゼ阻害剤として使用するための４−ピペリジニル化合物 Expired - Fee Related JP5957077B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201161507321P	2011-07-13	2011-07-13
US61/507,321		2011-07-13
PCT/IB2012/053613 WO2013008217A1 (en)	2011-07-13	2012-07-13	4 - piperidinyl compounds for use as tankyrase inhibitors

Publications (3)

Publication Number	Publication Date
JP2014522855A JP2014522855A (ja)	2014-09-08
JP2014522855A5 true JP2014522855A5 (2)	2015-08-06
JP5957077B2 JP5957077B2 (ja)	2016-07-27

Family

ID=46604017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2014519688A Expired - Fee Related JP5957077B2 (ja)	2011-07-13	2012-07-13	タンキラーゼ阻害剤として使用するための４−ピペリジニル化合物

Country Status (21)

Country	Link
US (2)	US9163003B2 (2)
EP (1)	EP2731940B1 (2)
JP (1)	JP5957077B2 (2)
KR (1)	KR20140051944A (2)
CN (1)	CN103797006B (2)
AP (1)	AP2014007400A0 (2)
AU (1)	AU2012282076A1 (2)
BR (1)	BR112014000792A2 (2)
CA (1)	CA2841932A1 (2)
CO (1)	CO6880065A2 (2)
CR (1)	CR20140071A (2)
DO (1)	DOP2014000012A (2)
EA (1)	EA201490272A1 (2)
ES (1)	ES2548513T3 (2)
IL (1)	IL230430A0 (2)
MA (1)	MA35342B1 (2)
MX (1)	MX2014000536A (2)
PH (1)	PH12014500126A1 (2)
TN (1)	TN2014000016A1 (2)
WO (1)	WO2013008217A1 (2)
ZA (1)	ZA201400374B (2)

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SG11201804901WA (en)	2015-12-22	2018-07-30	SHY Therapeutics LLC	Compounds for the treatment of cancer and inflammatory disease
WO2017156350A1 (en)	2016-03-09	2017-09-14	K-Gen, Inc.	Methods of cancer treatment
EA201992780A1 (ru)	2017-06-21	2020-06-02	ШАЙ ТЕРАПЬЮТИКС ЭлЭлСи	Соединения, которые взаимодействуют с суперсемейством ras, для лечения рака, воспалительных заболеваний, ras-опатий и фиброзного заболевания
CN113166097A (zh)	2018-12-03	2021-07-23	默克专利股份公司	作为端锚聚合酶抑制剂的4-杂芳基羰基-n-(苯基或杂芳基)哌啶-1-甲酰胺
US12391705B2 (en)	2018-12-19	2025-08-19	Shy Therapeutics, Llc	Compounds that interact with the Ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease
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- 2012-07-13 CA CA 2841932 patent/CA2841932A1/en not_active Abandoned
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- 2012-07-13 AP AP2014007400A patent/AP2014007400A0/xx unknown
- 2012-07-13 MX MX2014000536A patent/MX2014000536A/es not_active Application Discontinuation
- 2012-07-13 JP JP2014519688A patent/JP5957077B2/ja not_active Expired - Fee Related
- 2012-07-13 ES ES12742957.9T patent/ES2548513T3/es active Active
- 2012-07-13 BR BR112014000792A patent/BR112014000792A2/pt not_active IP Right Cessation
- 2012-07-13 CN CN201280043558.7A patent/CN103797006B/zh not_active Expired - Fee Related
- 2012-07-13 KR KR20147003628A patent/KR20140051944A/ko not_active Withdrawn
- 2012-07-13 US US15/786,125 patent/USRE46942E1/en active Active
- 2012-07-13 EA EA201490272A patent/EA201490272A1/ru unknown
- 2012-07-13 EP EP12742957.9A patent/EP2731940B1/en not_active Not-in-force
2014
- 2014-01-13 IL IL230430A patent/IL230430A0/en unknown
- 2014-01-15 TN TNP2014000016A patent/TN2014000016A1/en unknown
- 2014-01-17 ZA ZA2014/00374A patent/ZA201400374B/en unknown
- 2014-01-22 DO DO2014000012A patent/DOP2014000012A/es unknown
- 2014-02-10 MA MA36745A patent/MA35342B1/fr unknown
- 2014-02-12 CR CR20140071A patent/CR20140071A/es unknown
- 2014-02-13 CO CO14031176A patent/CO6880065A2/es not_active Application Discontinuation

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