JP2015537015A5 - - Google Patents
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- JP2015537015A5 JP2015537015A5 JP2015542247A JP2015542247A JP2015537015A5 JP 2015537015 A5 JP2015537015 A5 JP 2015537015A5 JP 2015542247 A JP2015542247 A JP 2015542247A JP 2015542247 A JP2015542247 A JP 2015542247A JP 2015537015 A5 JP2015537015 A5 JP 2015537015A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- fluoro
- methyl
- pyridin
- Prior art date
- 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
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- -1 cyclic amine Chemical class 0.000 claims 86
- 125000001424 substituent group Chemical group 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 28
- 239000012453 solvate Chemical class 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 21
- 125000003282 alkyl amino group Chemical group 0.000 claims 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 7
- 125000001246 bromo group Chemical group Br* 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- KOKYNZUSBROEHA-UHFFFAOYSA-N 6-fluoro-n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=C(F)C=C(CS(C)(=N)=O)C=2)=NC=C1F KOKYNZUSBROEHA-UHFFFAOYSA-N 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000035473 Communicable disease Diseases 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 241000700605 Viruses Species 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- WKKIMQXZPVZUOW-UHFFFAOYSA-N n-[4-(2-ethoxy-4-fluorophenyl)-5-fluoropyridin-2-yl]-6-fluoro-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound CCOC1=CC(F)=CC=C1C1=CC(NC=2N=C(F)C=C(CS(C)(=N)=O)C=2)=NC=C1F WKKIMQXZPVZUOW-UHFFFAOYSA-N 0.000 claims 3
- YCHNQROKRVOEFB-UHFFFAOYSA-N n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-4-[(methylsulfonimidoyl)methyl]-6-(trifluoromethyl)pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=C(C=C(CS(C)(=N)=O)C=2)C(F)(F)F)=NC=C1F YCHNQROKRVOEFB-UHFFFAOYSA-N 0.000 claims 3
- KOSGXPAAMHABHN-UHFFFAOYSA-N n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-6-methyl-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=C(C)C=C(CS(C)(=N)=O)C=2)=NC=C1F KOSGXPAAMHABHN-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- YZCUMZWULWOUMD-UHFFFAOYSA-N 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-[4-[(methylsulfonimidoyl)methyl]pyridin-2-yl]pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=CC=C(CS(C)(=N)=O)C=2)=NC=C1F YZCUMZWULWOUMD-UHFFFAOYSA-N 0.000 claims 2
- YGQVUPNZXRONRH-UHFFFAOYSA-N 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-n-[4-[(methylsulfonimidoyl)methyl]pyridin-2-yl]pyridin-2-amine;hydrochloride Chemical compound Cl.COC1=CC(F)=CC=C1C1=CC(NC=2N=CC=C(CS(C)(=N)=O)C=2)=NC=C1F YGQVUPNZXRONRH-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- GOTFVTNFJYZWIO-UHFFFAOYSA-N 5-bromo-n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-6-methyl-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=C(C)C(Br)=C(CS(C)(=N)=O)C=2)=NC=C1F GOTFVTNFJYZWIO-UHFFFAOYSA-N 0.000 claims 1
- JEKIHQZFDAHDFK-UHFFFAOYSA-N 6-chloro-n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=C(Cl)C=C(CS(C)(=N)=O)C=2)=NC=C1F JEKIHQZFDAHDFK-UHFFFAOYSA-N 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims 1
- GSAYYCASZXKVKU-UHFFFAOYSA-N n-[4-[(2-aminoethylsulfonimidoyl)methyl]pyridin-2-yl]-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-amine Chemical compound COC1=CC(F)=CC=C1C1=CC(NC=2N=CC=C(CS(=N)(=O)CCN)C=2)=NC=C1F GSAYYCASZXKVKU-UHFFFAOYSA-N 0.000 claims 1
- PAHQRWPSUQCXKS-UHFFFAOYSA-N n-[4-[(ethylsulfonimidoyl)methyl]pyridin-2-yl]-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-amine Chemical compound CCS(=N)(=O)CC1=CC=NC(NC=2N=CC(F)=C(C=2)C=2C(=CC(F)=CC=2)OC)=C1 PAHQRWPSUQCXKS-UHFFFAOYSA-N 0.000 claims 1
- OOPSDSZASQDBNK-UHFFFAOYSA-N n-[5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]-6-methoxy-4-[(methylsulfonimidoyl)methyl]pyridin-2-amine Chemical compound COC1=CC(CS(C)(=N)=O)=CC(NC=2N=CC(F)=C(C=2)C=2C(=CC(F)=CC=2)OC)=N1 OOPSDSZASQDBNK-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- DAFQZPUISLXFBF-UHFFFAOYSA-N tetraoxathiolane 5,5-dioxide Chemical compound O=S1(=O)OOOO1 DAFQZPUISLXFBF-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 CCOC(N=S(*)(Cc1c(*)c(*)nc(*)c1)=O)=O Chemical compound CCOC(N=S(*)(Cc1c(*)c(*)nc(*)c1)=O)=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12192852.7 | 2012-11-15 | ||
| EP12192852 | 2012-11-15 | ||
| PCT/EP2013/073637 WO2014076091A1 (en) | 2012-11-15 | 2013-11-12 | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfoximine group |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015537015A JP2015537015A (ja) | 2015-12-24 |
| JP2015537015A5 true JP2015537015A5 (OSRAM) | 2016-12-28 |
| JP6263193B2 JP6263193B2 (ja) | 2018-01-17 |
Family
ID=47148672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542247A Active JP6263193B2 (ja) | 2012-11-15 | 2013-11-12 | スルホキシイミン基を含んでいる５−フルオロ−ｎ−（ピリジン−２−イル）ピリジン−２−アミン誘導体 |
Country Status (42)
Families Citing this family (29)
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| TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之４－芳基－ｎ－苯基－１，３，５－三氮雜苯－２－胺 |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
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| HK1209414A1 (en) | 2012-10-18 | 2016-04-01 | Bayer Pharma Aktiengesellschaft | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group |
| TW201418243A (zh) | 2012-11-15 | 2014-05-16 | Bayer Pharma AG | 含有磺醯亞胺基團之ｎ－（吡啶－２－基）嘧啶－４－胺衍生物 |
| AU2013346939B2 (en) | 2012-11-15 | 2017-06-08 | Bayer Pharma Aktiengesellschaft | 5-fluoro-N-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfoximine group |
| BR112015014349A2 (pt) | 2012-12-17 | 2017-07-11 | Parion Sciences Inc | derivados de cloro-pirazina carboxamida úteis para o tratamento de doenças favorecidas por hidratação mucosa insuficiente |
| US9029382B2 (en) | 2012-12-17 | 2015-05-12 | Parion Sciences, Inc. | 3,5-diamino-6-chloro-N-(N-(4-phenylbutyl)carbamimidoyl) pyrazine-2-carboxamide compounds |
| ES2630115T3 (es) | 2013-07-04 | 2017-08-18 | Bayer Pharma Aktiengesellschaft | Derivados de 5-fluoro-n-(piridin-2-il)piridin-2-amina con sulfoximina sustituida y su uso como inhibidores de quinasa cdk9 |
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| CN106414412B (zh) | 2014-04-01 | 2019-06-21 | 拜耳医药股份有限公司 | 含有磺酰二亚胺基团的二取代的5-氟嘧啶衍生物 |
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| CA2999931A1 (en) | 2015-09-29 | 2017-04-06 | Bayer Pharma Aktiengesellschaft | Novel macrocyclic sulfondiimine compounds |
| JP6888000B2 (ja) | 2015-10-08 | 2021-06-16 | バイエル ファーマ アクチエンゲゼルシャフト | 新規な修飾された大環状化合物 |
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| EP3601236A1 (en) | 2017-03-28 | 2020-02-05 | Bayer Aktiengesellschaft | Novel ptefb inhibiting macrocyclic compounds |
| ES2900199T3 (es) | 2017-03-28 | 2022-03-16 | Bayer Ag | Novedosos compuestos macrocíclicos inhibidores de PTEFB |
| US11701347B2 (en) * | 2018-02-13 | 2023-07-18 | Bayer Aktiengesellschaft | Use of 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{4-[(S-methylsulfonimidoyl)methyl]pyridin-2-yl}pyridin-2-amine for treating diffuse large B-cell lymphoma |
| US20230102081A1 (en) | 2019-12-09 | 2023-03-30 | Cspc Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd. | Compound as cyclin-dependent kinase 9 inhibitor and use thereof |
| AU2021231312A1 (en) * | 2020-03-06 | 2022-08-25 | Bayer Aktiengesellschaft | Imidazotriazines acting on cancer via inhibition of CDK12 |
| CN116249701B (zh) * | 2020-10-12 | 2025-05-30 | 上海海雁医药科技有限公司 | 取代的二（吡啶-2-基）胺衍生物、其组合物及医药上的用途 |
| WO2023179597A1 (zh) * | 2022-03-25 | 2023-09-28 | 成都苑东生物制药股份有限公司 | 一种氨基吡啶类衍生物、其制备方法及用途 |
| WO2024044757A1 (en) * | 2022-08-26 | 2024-02-29 | Sanford Burnham Prebys Medical Discovery Institute | Aminopyrimidine and aminotriazine derivatives as myc protein modulators |
| KR20250127261A (ko) * | 2022-11-02 | 2025-08-26 | 빈서스 파마, 인코포레이티드 | 암에 대한 cdk9 억제제를 포함하는 병용 요법 |
| WO2024112656A1 (en) * | 2022-11-21 | 2024-05-30 | The Board Of Trustees Of The Leland Stanford Junior University | Use of a tyrosine kinase inhibitor for the treatment of hereditary hemorrhagic telangiectasia and pulmonary arterial hypertension |
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| CN105102434A (zh) | 2012-10-18 | 2015-11-25 | 拜耳药业股份公司 | 含砜基团的4-(邻)-氟苯基-5-氟嘧啶-2-基胺 |
| AU2013346939B2 (en) | 2012-11-15 | 2017-06-08 | Bayer Pharma Aktiengesellschaft | 5-fluoro-N-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfoximine group |
| US9499492B2 (en) | 2012-11-15 | 2016-11-22 | Bayer Pharma Aktiengesellschaft | 4-(ortho)-fluorophenyl-5-fluoropyrimidin-2-yl amines containing a sulfoximine group |
| ES2630115T3 (es) | 2013-07-04 | 2017-08-18 | Bayer Pharma Aktiengesellschaft | Derivados de 5-fluoro-n-(piridin-2-il)piridin-2-amina con sulfoximina sustituida y su uso como inhibidores de quinasa cdk9 |
| EP3116869A1 (en) | 2014-03-13 | 2017-01-18 | Bayer Pharma Aktiengesellschaft | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group |
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