JP2014527082A5 - - Google Patents
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- Publication number
- JP2014527082A5 JP2014527082A5 JP2014530756A JP2014530756A JP2014527082A5 JP 2014527082 A5 JP2014527082 A5 JP 2014527082A5 JP 2014530756 A JP2014530756 A JP 2014530756A JP 2014530756 A JP2014530756 A JP 2014530756A JP 2014527082 A5 JP2014527082 A5 JP 2014527082A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- amino
- hal
- ethyl
- piperazin
- 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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- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 6
- -1 (azetidin-1-yl) methyl Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QWLMSTZXMUMIFV-UHFFFAOYSA-N 2-[4-[6-amino-5-(4-fluorophenyl)pyrimidin-4-yl]piperazin-1-yl]-2-[6-(trifluoromethyl)pyridin-3-yl]acetonitrile Chemical compound C=1C=C(F)C=CC=1C=1C(N)=NC=NC=1N(CC1)CCN1C(C#N)C1=CC=C(C(F)(F)F)N=C1 QWLMSTZXMUMIFV-UHFFFAOYSA-N 0.000 claims 1
- BUFAZLRKDOFTLN-UHFFFAOYSA-N 2-[4-[6-amino-5-(4-fluorophenyl)pyrimidin-4-yl]piperazin-1-yl]-n-[2-(dimethylamino)ethyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C(=O)NCCN(C)C)N(CC1)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 BUFAZLRKDOFTLN-UHFFFAOYSA-N 0.000 claims 1
- YSMIANCCLJIZHM-KRWDZBQOSA-N 4-amino-1-[6-amino-5-(1h-pyrazol-4-yl)pyrimidin-4-yl]-n-[(1s)-1-(4-chlorophenyl)propyl]piperidine-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC(Cl)=CC=1)C(=O)C(CC1)(N)CCN1C1=NC=NC(N)=C1C=1C=NNC=1 YSMIANCCLJIZHM-KRWDZBQOSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- HRDNQTRURDVWED-KRWDZBQOSA-N 6-[4-[(1r)-2-amino-1-(6-chloropyridin-3-yl)ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C1CN([C@@H](CN)C=2C=NC(Cl)=CC=2)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 HRDNQTRURDVWED-KRWDZBQOSA-N 0.000 claims 1
- WZQPDUPNWNYRGZ-MRXNPFEDSA-N 6-[4-[(1s)-2-amino-1-(4-chlorophenyl)ethyl]piperazin-1-yl]-5-ethylpyrimidin-4-amine Chemical compound CCC1=C(N)N=CN=C1N1CCN([C@H](CN)C=2C=CC(Cl)=CC=2)CC1 WZQPDUPNWNYRGZ-MRXNPFEDSA-N 0.000 claims 1
- LRVNLSGZICUQLS-MRXNPFEDSA-N 6-[4-[(1s)-2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-(1h-pyrazol-4-yl)pyrimidin-4-amine Chemical compound C1CN([C@H](CN)C=2C=CC(=CC=2)C(F)(F)F)CCN1C1=NC=NC(N)=C1C=1C=NNC=1 LRVNLSGZICUQLS-MRXNPFEDSA-N 0.000 claims 1
- MMMSSXLSEGSDHS-LJQANCHMSA-N 6-[4-[(1s)-2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C1CN([C@H](CN)C=2C=CC(=CC=2)C(F)(F)F)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 MMMSSXLSEGSDHS-LJQANCHMSA-N 0.000 claims 1
- XVXGWZNJKSPVAQ-UHFFFAOYSA-N 6-[4-[2-(azetidin-1-yl)-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C=1C=C(F)C=CC=1C=1C(N)=NC=NC=1N(CC1)CCN1C(C=1C=CC(=CC=1)C(F)(F)F)CN1CCC1 XVXGWZNJKSPVAQ-UHFFFAOYSA-N 0.000 claims 1
- HYXXLNCSACYDRW-UHFFFAOYSA-N 6-[4-[2-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CN(C)C)N(CC1)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 HYXXLNCSACYDRW-UHFFFAOYSA-N 0.000 claims 1
- AVAIWPYMCQSQRB-UHFFFAOYSA-N 6-[4-[2-amino-1-(3-fluorophenyl)ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C=1C=CC(F)=CC=1C(CN)N(CC1)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 AVAIWPYMCQSQRB-UHFFFAOYSA-N 0.000 claims 1
- JNCDNFPUXLKIJP-UHFFFAOYSA-N 6-[4-[2-amino-1-(4-chloro-3-fluorophenyl)ethyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C=1C=C(Cl)C(F)=CC=1C(CN)N(CC1)CCN1C1=NC=NC(N)=C1C1=CC=C(F)C=C1 JNCDNFPUXLKIJP-UHFFFAOYSA-N 0.000 claims 1
- VCQXACIYKXUTSF-UHFFFAOYSA-N 6-[4-[2-amino-1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-(1h-pyrazol-4-yl)pyrimidin-4-amine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(CN)N(CC1)CCN1C1=NC=NC(N)=C1C=1C=NNC=1 VCQXACIYKXUTSF-UHFFFAOYSA-N 0.000 claims 1
- VHMVHAGZKRSNDS-UHFFFAOYSA-N 6-[4-[2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-chloropyrimidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CN)N(CC1)CCN1C1=NC=NC(N)=C1Cl VHMVHAGZKRSNDS-UHFFFAOYSA-N 0.000 claims 1
- CRRPJTULCQOFOC-UHFFFAOYSA-N 6-[4-[2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-ethenylpyrimidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CN)N(CC1)CCN1C1=NC=NC(N)=C1C=C CRRPJTULCQOFOC-UHFFFAOYSA-N 0.000 claims 1
- PUDRMQRZDFNBTI-UHFFFAOYSA-N 6-[4-[2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-ethoxypyrimidin-4-amine Chemical compound CCOC1=C(N)N=CN=C1N1CCN(C(CN)C=2C=CC(=CC=2)C(F)(F)F)CC1 PUDRMQRZDFNBTI-UHFFFAOYSA-N 0.000 claims 1
- CBGPEGDCORSVLT-UHFFFAOYSA-N 6-[4-[2-amino-1-[4-(trifluoromethyl)phenyl]ethyl]piperidin-1-yl]-5-(1h-pyrazol-4-yl)pyrimidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CN)C(CC1)CCN1C1=NC=NC(N)=C1C=1C=NNC=1 CBGPEGDCORSVLT-UHFFFAOYSA-N 0.000 claims 1
- WOHMLWSICHUZCI-UHFFFAOYSA-N 6-[4-[3-(azetidin-1-yl)-1-(4-chlorophenyl)propyl]piperazin-1-yl]-5-(4-fluorophenyl)pyrimidin-4-amine Chemical compound C=1C=C(F)C=CC=1C=1C(N)=NC=NC=1N(CC1)CCN1C(C=1C=CC(Cl)=CC=1)CCN1CCC1 WOHMLWSICHUZCI-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000002615 epidermis Anatomy 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 210000000066 myeloid cell Anatomy 0.000 claims 1
- NXMLJMUXZVBHIY-UHFFFAOYSA-N n-[[3-amino-1-[6-amino-5-(4-fluorophenyl)pyrimidin-4-yl]pyrrolidin-3-yl]methyl]-2,4-difluorobenzamide Chemical compound C=1C=C(F)C=CC=1C=1C(N)=NC=NC=1N(C1)CCC1(N)CNC(=O)C1=CC=C(F)C=C1F NXMLJMUXZVBHIY-UHFFFAOYSA-N 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161533606P | 2011-09-12 | 2011-09-12 | |
| US61/533,606 | 2011-09-12 | ||
| PCT/US2012/054877 WO2013040044A1 (en) | 2011-09-12 | 2012-09-12 | Aminopyrimidine derivatives for use as modulators of kinase activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014527082A JP2014527082A (ja) | 2014-10-09 |
| JP2014527082A5 true JP2014527082A5 (enExample) | 2016-09-29 |
| JP6082011B2 JP6082011B2 (ja) | 2017-02-15 |
Family
ID=46964039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014530756A Expired - Fee Related JP6082011B2 (ja) | 2011-09-12 | 2012-09-12 | キナーゼ活性のモジュレーターとして使用するためのアミノピリミジン誘導体 |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US9321760B2 (enExample) |
| EP (1) | EP2755958B9 (enExample) |
| JP (1) | JP6082011B2 (enExample) |
| KR (1) | KR101992505B1 (enExample) |
| CN (2) | CN106946796B (enExample) |
| AU (2) | AU2012308681B2 (enExample) |
| BR (1) | BR112014005468A2 (enExample) |
| CA (1) | CA2844704C (enExample) |
| DK (1) | DK2755958T3 (enExample) |
| EA (1) | EA028057B1 (enExample) |
| ES (1) | ES2646759T3 (enExample) |
| HR (1) | HRP20171655T1 (enExample) |
| HU (1) | HUE034979T2 (enExample) |
| IL (2) | IL231381B (enExample) |
| LT (1) | LT2755958T (enExample) |
| MX (1) | MX347241B (enExample) |
| NO (1) | NO2639780T3 (enExample) |
| PL (1) | PL2755958T3 (enExample) |
| PT (1) | PT2755958T (enExample) |
| RS (1) | RS56486B1 (enExample) |
| SG (1) | SG2014009260A (enExample) |
| SI (1) | SI2755958T1 (enExample) |
| WO (1) | WO2013040044A1 (enExample) |
| ZA (1) | ZA201401007B (enExample) |
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|---|---|---|---|---|
| SG10201604682VA (en) | 2011-06-10 | 2016-07-28 | Merck Patent Gmbh | Compositions and methods for the production of pyrimidine and pyridine compounds with btk inhibitory activity |
| JP6082011B2 (ja) * | 2011-09-12 | 2017-02-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | キナーゼ活性のモジュレーターとして使用するためのアミノピリミジン誘導体 |
| ES2620119T3 (es) | 2012-11-16 | 2017-06-27 | Merck Patent Gmbh | Derivados heterocíclicos novedosos como moduladores de la actividad de quinasa |
| AR095202A1 (es) * | 2013-03-11 | 2015-09-30 | Merck Patent Gmbh | Heterociclos como moduladores de la actividad quinasa |
| JO3517B1 (ar) | 2014-01-17 | 2020-07-05 | Novartis Ag | ان-ازاسبيرو الكان حلقي كبديل مركبات اريل-ان مغايرة وتركيبات لتثبيط نشاط shp2 |
| WO2015107493A1 (en) | 2014-01-17 | 2015-07-23 | Novartis Ag | 1 -pyridazin-/triazin-3-yl-piper(-azine)/idine/pyrolidine derivatives and and compositions thereof for inhibiting the activity of shp2 |
| ES2699354T3 (es) | 2014-01-17 | 2019-02-08 | Novartis Ag | Derivados de 1-(triazin-3-il/piridazin-3-il)-piper(-azin)idina y composiciones de las mismas para inhibir la actividad de SHP2 |
| RU2690679C2 (ru) * | 2014-02-11 | 2019-06-05 | Мерк Патент Гмбх | Новые пиримидинимидазоламины в качестве модуляторов активности киназы |
| EP2939514B1 (en) | 2014-04-30 | 2018-09-05 | LG Electronics Inc. | Lawn mower robot and control method thereof |
| AU2015265696B2 (en) * | 2014-05-28 | 2018-01-18 | Astrazeneca Ab | Processes for the preparation of AZD5363 and novel intermediate used therein |
| JP6878316B2 (ja) | 2015-06-19 | 2021-05-26 | ノバルティス アーゲー | Ｓｈｐ２の活性を阻害するための化合物および組成物 |
| WO2016203404A1 (en) | 2015-06-19 | 2016-12-22 | Novartis Ag | Compounds and compositions for inhibiting the activity of shp2 |
| CN112625028B (zh) | 2015-06-19 | 2024-10-29 | 诺华股份有限公司 | 用于抑制shp2活性的化合物和组合物 |
| WO2017019804A2 (en) | 2015-07-28 | 2017-02-02 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| JP6921846B6 (ja) * | 2016-03-16 | 2021-09-15 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節およびその適応症のための化合物および方法 |
| RU2744988C2 (ru) | 2016-06-14 | 2021-03-17 | Новартис Аг | Соединения и композиции для подавления активности shp2 |
| CA3048340A1 (en) | 2017-01-10 | 2018-07-19 | Novartis Ag | Pharmaceutical combination comprising an alk inhibitor and a shp2 inhibitor |
| CN109467538A (zh) | 2017-09-07 | 2019-03-15 | 和记黄埔医药（上海）有限公司 | 环烯烃取代的杂芳环类化合物及其用途 |
| WO2019084395A1 (en) | 2017-10-27 | 2019-05-02 | University Of Virginia Patent Foundation | COMPOUNDS AND METHODS FOR REGULATING, LIMITING OR INHIBITING AVIL EXPRESSION |
| EP3962485A4 (en) * | 2019-05-02 | 2022-12-28 | University Of Virginia Patent Foundation | SUBSTITUTED (PIPERIDINE-1-YL)ARYL ANALOGUES TO MODULATE AVILACTIVITY |
| US11866421B2 (en) | 2021-05-31 | 2024-01-09 | Epigen Biosciences, Inc. | Pyrimidine and pyridine amine compounds and usage thereof in disease treatment |
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| JP2007507531A (ja) | 2003-09-30 | 2007-03-29 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤としての化合物および組成物 |
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| CA2818706C (en) | 2010-11-24 | 2019-07-23 | Merck Patent Gmbh | Quinazoline carboxamide azetidines |
| ES2644536T3 (es) * | 2011-09-12 | 2017-11-29 | Merck Patent Gmbh | Imidazol-aminas novedosas como moduladores de la actividad cinasa |
| JP6082011B2 (ja) * | 2011-09-12 | 2017-02-15 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | キナーゼ活性のモジュレーターとして使用するためのアミノピリミジン誘導体 |
| ES2807539T3 (es) * | 2012-11-16 | 2021-02-23 | Merck Patent Gmbh | Derivados de imidazol-piperidinilo como moduladores de la actividad de quinasa |
| RU2690679C2 (ru) * | 2014-02-11 | 2019-06-05 | Мерк Патент Гмбх | Новые пиримидинимидазоламины в качестве модуляторов активности киназы |
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- 2012-09-12 WO PCT/US2012/054877 patent/WO2013040044A1/en not_active Ceased
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