JP5891249B2 - ７−アザインドール誘導体 - Google Patents
７−アザインドール誘導体 Download PDFInfo
- Publication number
- JP5891249B2 JP5891249B2 JP2013552124A JP2013552124A JP5891249B2 JP 5891249 B2 JP5891249 B2 JP 5891249B2 JP 2013552124 A JP2013552124 A JP 2013552124A JP 2013552124 A JP2013552124 A JP 2013552124A JP 5891249 B2 JP5891249 B2 JP 5891249B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrrolo
- pyridin
- compound
- formula
- 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.)
- Expired - Fee Related
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- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 title description 3
- -1 2,7-naphthyridin-4-yl Chemical group 0.000 claims description 128
- 150000001875 compounds Chemical class 0.000 claims description 119
- 150000003839 salts Chemical class 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 48
- 206010028980 Neoplasm Diseases 0.000 claims description 46
- 238000011282 treatment Methods 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 230000001028 anti-proliverative effect Effects 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229940127089 cytotoxic agent Drugs 0.000 claims description 5
- 239000002254 cytotoxic agent Substances 0.000 claims description 5
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 5
- 239000002834 estrogen receptor modulator Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 102000027483 retinoid hormone receptors Human genes 0.000 claims description 5
- 108091008679 retinoid hormone receptors Proteins 0.000 claims description 5
- 239000000849 selective androgen receptor modulator Substances 0.000 claims description 5
- 230000004614 tumor growth Effects 0.000 claims description 5
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
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- 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical compound C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 claims description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
- 206010027476 Metastases Diseases 0.000 claims description 3
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- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 3
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000004663 cell proliferation Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 102000001284 I-kappa-B kinase Human genes 0.000 description 8
- 108060006678 I-kappa-B kinase Proteins 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 102000001253 Protein Kinase Human genes 0.000 description 7
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 7
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 7
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- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 108060006633 protein kinase Proteins 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Health & Medical Sciences (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| SG186855A1 (en) * | 2010-06-28 | 2013-02-28 | Merck Patent Gmbh | 2,4- diaryl - substituted [1,8] naphthyridines as kinase inhibitors for use against cancer |
| DE102010053347A1 (de) * | 2010-12-03 | 2012-06-06 | Merck Patent Gmbh | 3-Hetaryl-substituierte Pyrrolo[2,3-b] pyridin-derivative als PDK1-Inhibitoren |
| DE102011009961A1 (de) * | 2011-02-01 | 2012-08-02 | Merck Patent Gmbh | 7-Azaindolderivate |
| ES2606638T3 (es) * | 2012-02-21 | 2017-03-24 | Merck Patent Gmbh | Derivados de furopiridina |
| DE102012019369A1 (de) | 2012-10-02 | 2014-04-03 | Merck Patent Gmbh | 7-Azaindolderivat |
| FR3001219A1 (fr) * | 2013-01-22 | 2014-07-25 | Centre Nat Rech Scient | Inhibiteurs de kinases |
| GB201303109D0 (en) | 2013-02-21 | 2013-04-10 | Domainex Ltd | Novel pyrimidine compounds |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| RU2680100C9 (ru) * | 2013-03-15 | 2019-04-18 | Плексксикон Инк. | Гетероциклические соединения и их применения |
| TW201613916A (en) | 2014-06-03 | 2016-04-16 | Gilead Sciences Inc | TANK-binding kinase inhibitor compounds |
| ES2881195T3 (es) | 2014-09-26 | 2021-11-29 | Gilead Sciences Inc | Derivados de aminotriazina útiles como compuestos inhibidores de quinasas que se unen a TANK |
| WO2016141279A1 (en) * | 2015-03-04 | 2016-09-09 | Dana-Farber Cancer Institute, Inc. | Salicylate inhibitors of melk and methods of use |
| WO2016164641A1 (en) * | 2015-04-08 | 2016-10-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US9988391B2 (en) * | 2015-06-29 | 2018-06-05 | Merck Patent Gmbh | TBK/IKK inhibitor compounds and uses thereof |
| CA3006772A1 (en) | 2015-12-17 | 2017-06-22 | Gilead Sciences, Inc. | Tank-binding kinase inhibitor compounds |
| WO2017102091A1 (en) | 2015-12-18 | 2017-06-22 | Bayer Pharma Aktiengesellschaft | Heteroarylbenzimidazole compounds |
| CN105906608B (zh) * | 2016-05-03 | 2018-10-19 | 中山大学 | 8-氨基喹啉-松果体素杂联体及其药物组合物 |
| WO2017207534A1 (en) | 2016-06-03 | 2017-12-07 | Bayer Pharma Aktiengesellschaft | Substituted heteroarylbenzimidazole compounds |
| GB201702947D0 (en) | 2017-02-23 | 2017-04-12 | Domainex Ltd | Novel compounds |
| US11180495B2 (en) * | 2017-06-19 | 2021-11-23 | Abbisko Therapeutics Co., Ltd. | Nitrogen heteroaryl derivative having CSF1R inhibitory activity, and preparation method therefor and application thereof |
| JP7675519B2 (ja) | 2017-10-13 | 2025-05-13 | オプナ バイオ ソシエテ アノニム | キナーゼを調節するための化合物の固体形態 |
| US12448374B2 (en) | 2018-06-07 | 2025-10-21 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 |
| ES3028093T3 (en) | 2018-06-07 | 2025-06-18 | Disarm Therapeutics Inc | Inhibitors of sarm1 |
| KR20200046680A (ko) * | 2018-10-25 | 2020-05-07 | 한국과학기술원 | Pdk1 저해제를 포함하는 역노화 유도용 조성물 |
| WO2025016273A1 (zh) * | 2023-07-14 | 2025-01-23 | 拜西欧斯（北京）生物技术有限公司 | 异喹啉衍生物、包含其的药物组合物以及它们的用途 |
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| US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
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| JP2003500397A (ja) | 1999-05-19 | 2003-01-07 | スミスクライン ビーチャム パブリック リミテッド カンパニー | Ｍｒｓ阻害剤としての２−ｎｈ−ピリドンおよびピリミドン |
| CA2545942C (en) | 2003-11-14 | 2012-07-10 | Lorus Therapeutics Inc. | Aryl imidazoles and their use as anti-cancer agents |
| SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| CN100569772C (zh) * | 2004-03-30 | 2009-12-16 | 沃泰克斯药物股份有限公司 | 用作jak和其它蛋白激酶抑制剂的氮杂吲哚 |
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| JP2008502687A (ja) * | 2004-06-14 | 2008-01-31 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
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| JP2007099640A (ja) * | 2005-09-30 | 2007-04-19 | Tsumura & Co | 含窒素複素環化合物、その製造方法およびそれを用いた医薬組成物 |
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| ES2395581T3 (es) | 2007-06-20 | 2013-02-13 | Merck Sharp & Dohme Corp. | Inhibidores de quinasas janus |
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| DE102009019962A1 (de) * | 2009-05-05 | 2010-11-11 | Merck Patent Gmbh | 3-([1,2,3]Triazol-4-yl)-pyrrolo[2,3-b]pyridinderivate |
| EP2576549A4 (en) * | 2010-05-24 | 2013-12-18 | Univ Rochester | BICYCLIC HETEROARYLATES FORMING KINASE INHIBITORS AND METHODS OF USE |
| SG186855A1 (en) * | 2010-06-28 | 2013-02-28 | Merck Patent Gmbh | 2,4- diaryl - substituted [1,8] naphthyridines as kinase inhibitors for use against cancer |
| DE102010053347A1 (de) | 2010-12-03 | 2012-06-06 | Merck Patent Gmbh | 3-Hetaryl-substituierte Pyrrolo[2,3-b] pyridin-derivative als PDK1-Inhibitoren |
| DE102011009961A1 (de) * | 2011-02-01 | 2012-08-02 | Merck Patent Gmbh | 7-Azaindolderivate |
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2011
- 2011-02-01 DE DE102011009961A patent/DE102011009961A1/de not_active Withdrawn
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- 2012-01-09 CN CN201610048764.7A patent/CN105712991B/zh not_active Expired - Fee Related
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- 2012-01-09 SG SG2013056726A patent/SG192133A1/en unknown
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- 2012-01-09 KR KR1020137022887A patent/KR20140014158A/ko not_active Withdrawn
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