ES2822956T3 - Compuestos de aminopiridina sustituidos con heteroarilo - Google Patents

Compuestos de aminopiridina sustituidos con heteroarilo Download PDF

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Publication number: ES2822956T3
Authority: ES; Spain
Prior art keywords: pyridin; alkyl; carbonitrile; isopropylamino; pyrazol
Prior art date: 2015-06-24
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.): Active

Application number

ES16734832T

Other languages

English (en)

Spanish (es)

Inventor

John V Duncia

Daniel S Gardner

John Hynes

John E Macor

Joseph B Santella

Hong Wu

Satheesh Kesavan Nair

Venkatram Reddy Paidi

Kandhasamy Sarkunam

Ramesh Kumar Sistla

Subba Rao Polimera

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

Priority date (The priority date 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 date listed.)

2015-06-24

Filing date

2016-06-23

Publication date

2021-05-05

2016-06-23 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2021-05-05 Application granted granted Critical

2021-05-05 Publication of ES2822956T3 publication Critical patent/ES2822956T3/es

Status Active legal-status Critical Current

2036-06-23 Anticipated expiration legal-status Critical

Links

-1 aminopyridine compounds Chemical class 0.000 title claims abstract description 99
125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 33
150000001875 compounds Chemical class 0.000 claims abstract description 192
150000003839 salts Chemical class 0.000 claims abstract description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 24
125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 21
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 21
125000004076 pyridyl group Chemical group 0.000 claims abstract description 20
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 10
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 10
125000001425 triazolyl group Chemical group 0.000 claims abstract description 10
125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 9
125000003566 oxetanyl group Chemical group 0.000 claims abstract description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
125000002393 azetidinyl group Chemical group 0.000 claims abstract description 6
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 6
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 claims abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 5
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 4
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 75
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239000003937 drug carrier Substances 0.000 claims description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
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RENRCXJODALGTE-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-5-[1-(oxan-4-yl)pyrazol-4-yl]-N-propan-2-ylpyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC(C)C)C=1C=NN(C=1)C1CCOCC1 RENRCXJODALGTE-UHFFFAOYSA-N 0.000 claims description 8
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239000003085 diluting agent Substances 0.000 claims description 7
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XOYXADDAQJVPEI-UHFFFAOYSA-N 3-[5-[1-(3-hydroxy-3-methylbutyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound OC(CCN1N=CC(=C1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C)(C)C XOYXADDAQJVPEI-UHFFFAOYSA-N 0.000 claims description 6
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ZACIZZRZZPYFAZ-UHFFFAOYSA-N 1-[4-[6-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-4-(propan-2-ylamino)pyridin-3-yl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=CC(=C(C=N1)C=1C=NN(C=1)CC(C)(O)C)NC(C)C ZACIZZRZZPYFAZ-UHFFFAOYSA-N 0.000 claims description 5
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ZBRIPMUNBFXCSD-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-N-propan-2-yl-5-(1-propyltriazol-4-yl)pyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC(C)C)C=1N=NN(C=1)CCC ZBRIPMUNBFXCSD-UHFFFAOYSA-N 0.000 claims description 4
KFILYRVIDVXHNI-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-N-propan-2-yl-5-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]pyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC(C)C)C=1C=NN(C=1)CC(F)(F)F KFILYRVIDVXHNI-UHFFFAOYSA-N 0.000 claims description 4
JDHXZJLBUNAELN-UHFFFAOYSA-N 3-[4-(cyclopropylamino)-5-(1-propyltriazol-4-yl)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound C1(CC1)NC1=CC(=NC=C1C=1N=NN(C=1)CCC)C1=CN=C2N1N=CC(=C2)C#N JDHXZJLBUNAELN-UHFFFAOYSA-N 0.000 claims description 4
TWOADEWSFFZZFG-UHFFFAOYSA-N 3-[4-(propan-2-ylamino)-5-(1-propylpyrazol-4-yl)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1C=NN(C=1)CCC)C1=CN=C2N1N=CC(=C2)C#N TWOADEWSFFZZFG-UHFFFAOYSA-N 0.000 claims description 4
FRYFNOMIOVBKEM-UHFFFAOYSA-N 3-[4-[(3,3-difluorocyclobutyl)amino]-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound FC1(CC(C1)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)C=1C=NN2C=1N=CC(=C2)C#N)F FRYFNOMIOVBKEM-UHFFFAOYSA-N 0.000 claims description 4
SOVIOGDRQIIPMO-UHFFFAOYSA-N 3-[4-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-(1-propylpyrazol-4-yl)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound FC(CN1N=CC(=C1)NC1=CC(=NC=C1C=1C=NN(C=1)CCC)C1=CN=C2N1N=CC(=C2)C#N)F SOVIOGDRQIIPMO-UHFFFAOYSA-N 0.000 claims description 4
FXJWDSCIKROGLP-UHFFFAOYSA-N 3-[5-[1-(1-acetylazetidin-3-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound C(C)(=O)N1CC(C1)N1N=NC(=C1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C FXJWDSCIKROGLP-UHFFFAOYSA-N 0.000 claims description 4
KIFBHFOPKPWRAP-UHFFFAOYSA-N 3-[5-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound OC(CN1N=CC(=C1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C)(C)C KIFBHFOPKPWRAP-UHFFFAOYSA-N 0.000 claims description 4
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PYJGADHQKPQSHH-UHFFFAOYSA-N 3-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(oxetan-3-ylamino)pyridin-2-yl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)C=1C=NN2C=1N=CC(=C2)C#N)NC1COC1)(C)C PYJGADHQKPQSHH-UHFFFAOYSA-N 0.000 claims description 4
BXPJRPWKDYCOMG-UHFFFAOYSA-N 3-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C)(C)C BXPJRPWKDYCOMG-UHFFFAOYSA-N 0.000 claims description 4
CCXZYUPDEZUPCM-UHFFFAOYSA-N 4-[1-[6-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-4-(oxan-4-ylamino)pyridin-3-yl]triazol-4-yl]-2-methylbutan-2-ol Chemical compound ClC=1C=NC=2N(C=1)N=CC=2C1=CC(=C(C=N1)N1N=NC(=C1)CCC(C)(O)C)NC1CCOCC1 CCXZYUPDEZUPCM-UHFFFAOYSA-N 0.000 claims description 4
WQSAYCODPMMYLW-UHFFFAOYSA-N 4-[1-[6-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-4-(oxetan-3-ylamino)pyridin-3-yl]triazol-4-yl]-2-methylbutan-2-ol Chemical compound ClC=1C=NC=2N(C=1)N=CC=2C1=CC(=C(C=N1)N1N=NC(=C1)CCC(C)(O)C)NC1COC1 WQSAYCODPMMYLW-UHFFFAOYSA-N 0.000 claims description 4
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IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
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ES16734832T 2015-06-24 2016-06-23 Compuestos de aminopiridina sustituidos con heteroarilo Active ES2822956T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IN1880DE2015		2015-06-24
PCT/US2016/038862 WO2016210037A1 (en)	2015-06-24	2016-06-23	Heteroaryl substituted aminopyridine compounds

Publications (1)

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Country Status (9)

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US (1)	US10202390B2 (2)
EP (1)	EP3313844B1 (2)
JP (1)	JP6720225B2 (2)
CN (1)	CN108026099B (2)
AR (1)	AR105114A1 (2)
ES (1)	ES2822956T3 (2)
TW (1)	TW201713663A (2)
UY (1)	UY36747A (2)
WO (1)	WO2016210037A1 (2)

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ES2822956T3 (es)	2015-06-24	2021-05-05	Bristol Myers Squibb Co	Compuestos de aminopiridina sustituidos con heteroarilo

2016
- 2016-06-23 ES ES16734832T patent/ES2822956T3/es active Active
- 2016-06-23 EP EP16734832.5A patent/EP3313844B1/en active Active
- 2016-06-23 CN CN201680043479.4A patent/CN108026099B/zh active Active
- 2016-06-23 TW TW105119779A patent/TW201713663A/zh unknown
- 2016-06-23 WO PCT/US2016/038862 patent/WO2016210037A1/en not_active Ceased
- 2016-06-23 UY UY0001036747A patent/UY36747A/es not_active Application Discontinuation
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- 2016-06-23 US US15/738,435 patent/US10202390B2/en active Active
- 2016-06-23 JP JP2017566812A patent/JP6720225B2/ja active Active

Also Published As

Publication number	Publication date
WO2016210037A1 (en)	2016-12-29
US20180179213A1 (en)	2018-06-28
JP2018524331A (ja)	2018-08-30
CN108026099A (zh)	2018-05-11
AR105114A1 (es)	2017-09-06
UY36747A (es)	2016-12-30
JP6720225B2 (ja)	2020-07-08
US10202390B2 (en)	2019-02-12
EP3313844A1 (en)	2018-05-02
EP3313844B1 (en)	2020-08-26
CN108026099B (zh)	2020-07-10
TW201713663A (zh)	2017-04-16

Publication	Publication Date	Title
ES2822956T3 (es)	2021-05-05	Compuestos de aminopiridina sustituidos con heteroarilo
ES2745525T3 (es)	2020-03-02	Compuestos de aminopiridina sustituida con heteroarilo
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CN114206874B (zh)	2024-08-02	可用作irak4抑制剂的双环杂芳基化合物
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AU2013227024A1 (en)	2014-09-18	Novel piperidine compound or salt thereof
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