RU2384571C2 - Конденсированное хинолиновое производное и его применение - Google Patents
Конденсированное хинолиновое производное и его применение Download PDFInfo
- Publication number
- RU2384571C2 RU2384571C2 RU2006141842/04A RU2006141842A RU2384571C2 RU 2384571 C2 RU2384571 C2 RU 2384571C2 RU 2006141842/04 A RU2006141842/04 A RU 2006141842/04A RU 2006141842 A RU2006141842 A RU 2006141842A RU 2384571 C2 RU2384571 C2 RU 2384571C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- halogen
- alkoxy
- carbonyl
- substituent
- Prior art date
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- 0 CCCC(C)C1(CCCCC1)C(C)C*C(C)=O Chemical compound CCCC(C)C1(CCCCC1)C(C)C*C(C)=O 0.000 description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N NC(c1ccccc1)=O Chemical compound NC(c1ccccc1)=O KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- QROGIFZRVHSFLM-KXFIGUGUSA-N C/C=C\c1ccccc1 Chemical compound C/C=C\c1ccccc1 QROGIFZRVHSFLM-KXFIGUGUSA-N 0.000 description 1
- PZZTXICVCLBAGO-UHFFFAOYSA-N C1c(c(-c2ccccc2)nc2ccccc22)c2NC1 Chemical compound C1c(c(-c2ccccc2)nc2ccccc22)c2NC1 PZZTXICVCLBAGO-UHFFFAOYSA-N 0.000 description 1
- XMEROAWEYKTVJL-PAVWDGINSA-N C=C(CN([C@H]12)C([C@@H](CCCC3)[C@@H]3NC(c(cc3)ccc3C(O)=O)=O)=O)[C@@H]1[C@H](c1ccccc1)Nc1c2cccc1 Chemical compound C=C(CN([C@H]12)C([C@@H](CCCC3)[C@@H]3NC(c(cc3)ccc3C(O)=O)=O)=O)[C@@H]1[C@H](c1ccccc1)Nc1c2cccc1 XMEROAWEYKTVJL-PAVWDGINSA-N 0.000 description 1
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- BUHFUEJYZGDKQK-WXGGYGAESA-N CC(C)C[C@@H]([C@H]1CC2)Nc3ccccc3[C@@H]1N2C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)=O Chemical compound CC(C)C[C@@H]([C@H]1CC2)Nc3ccccc3[C@@H]1N2C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)=O BUHFUEJYZGDKQK-WXGGYGAESA-N 0.000 description 1
- KYMONYJYPRZWNR-JMNORXHVSA-N CC(NCCCC(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c(cccc3)c3N[C@@H](COC)[C@H]2CC1)=O)=O)=O Chemical compound CC(NCCCC(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c(cccc3)c3N[C@@H](COC)[C@H]2CC1)=O)=O)=O KYMONYJYPRZWNR-JMNORXHVSA-N 0.000 description 1
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- OPOXIVCDRICEEV-UHFFFAOYSA-N CCOC(CC1(CCOCC1)O)=O Chemical compound CCOC(CC1(CCOCC1)O)=O OPOXIVCDRICEEV-UHFFFAOYSA-N 0.000 description 1
- YQBBOURFMZPYIA-UHFFFAOYSA-N CCOC(c(cc1)ccc1N(C)CCOC)=O Chemical compound CCOC(c(cc1)ccc1N(C)CCOC)=O YQBBOURFMZPYIA-UHFFFAOYSA-N 0.000 description 1
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- TYPJTRNRNGDTHK-FAYRPWDUSA-N CN(C)c(cccc1)c1C(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c3ccccc3N[C@@H](COC)[C@H]2CC1)=O)=O Chemical compound CN(C)c(cccc1)c1C(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c3ccccc3N[C@@H](COC)[C@H]2CC1)=O)=O TYPJTRNRNGDTHK-FAYRPWDUSA-N 0.000 description 1
- LOWUQZKALMKHOV-XMHIYREPSA-N CN(CC1)CCN1c(cc1)ccc1C(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c(cccc3)c3N[C@@H](COC)[C@H]2CC1)=O)=O Chemical compound CN(CC1)CCN1c(cc1)ccc1C(N[C@H](CCCC1)[C@H]1C(N1[C@H]2c(cccc3)c3N[C@@H](COC)[C@H]2CC1)=O)=O LOWUQZKALMKHOV-XMHIYREPSA-N 0.000 description 1
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- MBHJRZMASFIJBE-UHFFFAOYSA-N COc1cc(C(O)=O)ccc1C#N Chemical compound COc1cc(C(O)=O)ccc1C#N MBHJRZMASFIJBE-UHFFFAOYSA-N 0.000 description 1
- LQGHBKPIJSBKEY-QPJJXVBHSA-N COc1ccc(/C=C/C(N)=O)cc1 Chemical compound COc1ccc(/C=C/C(N)=O)cc1 LQGHBKPIJSBKEY-QPJJXVBHSA-N 0.000 description 1
- WKSJZGIYHAPUND-ILGMUSQUSA-N C[C@@H]([C@H]1CC2)Nc3ccccc3[C@@H]1N2C([C@@H](CCCC1)[C@@H]1NC(Nc(cc1)cc(C#N)c1OC)=O)=O Chemical compound C[C@@H]([C@H]1CC2)Nc3ccccc3[C@@H]1N2C([C@@H](CCCC1)[C@@H]1NC(Nc(cc1)cc(C#N)c1OC)=O)=O WKSJZGIYHAPUND-ILGMUSQUSA-N 0.000 description 1
- RELCXNWMJHWAOG-GJZGRUSLSA-N C[C@@H]1Nc2ccccc2C[C@@H]1CC[N-][IH](C1CCCCC1)=O Chemical compound C[C@@H]1Nc2ccccc2C[C@@H]1CC[N-][IH](C1CCCCC1)=O RELCXNWMJHWAOG-GJZGRUSLSA-N 0.000 description 1
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- WBFUBNWKSDINIX-UHFFFAOYSA-N Cc1c(C=O)cc[o]1 Chemical compound Cc1c(C=O)cc[o]1 WBFUBNWKSDINIX-UHFFFAOYSA-N 0.000 description 1
- XPYMXTGGIYNKFL-QJBPMSQXSA-N N#Cc1cc(N[C@H]([C@@H](CC2)[C@H]3N2C([C@@H](CCCC2)[C@@H]2NC(c2ccccc2)=O)=O)c2ccccc2)c3cc1 Chemical compound N#Cc1cc(N[C@H]([C@@H](CC2)[C@H]3N2C([C@@H](CCCC2)[C@@H]2NC(c2ccccc2)=O)=O)c2ccccc2)c3cc1 XPYMXTGGIYNKFL-QJBPMSQXSA-N 0.000 description 1
- JQPLVGAHZIEEQE-HUROMRQRSA-N N#Cc1ccc([C@H]([C@@H](CC2)[C@@H](c3ccccc3)N3)N2C(CCNC(c2ccccc2)=O)=O)c3c1 Chemical compound N#Cc1ccc([C@H]([C@@H](CC2)[C@@H](c3ccccc3)N3)N2C(CCNC(c2ccccc2)=O)=O)c3c1 JQPLVGAHZIEEQE-HUROMRQRSA-N 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N N#Cc1ccccc1 Chemical compound N#Cc1ccccc1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
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- DESTUXAYCQSXTK-GMAHTHKFSA-N O=C(C1CCCCC1)[N-2]CC[C@@H]1[C@H](c2ccccc2)Nc2ccccc2C1 Chemical compound O=C(C1CCCCC1)[N-2]CC[C@@H]1[C@H](c2ccccc2)Nc2ccccc2C1 DESTUXAYCQSXTK-GMAHTHKFSA-N 0.000 description 1
- XLTKNBOWGMKJSO-MXJRWRDHSA-N O=C(C[C@@H](CCCC1)[C@@H]1NC(c(cc1Cl)ccc1F)=O)N(CC[C@@H]12)[C@H]1c1ccccc1N[C@H]2c1ncc[nH]1 Chemical compound O=C(C[C@@H](CCCC1)[C@@H]1NC(c(cc1Cl)ccc1F)=O)N(CC[C@@H]12)[C@H]1c1ccccc1N[C@H]2c1ncc[nH]1 XLTKNBOWGMKJSO-MXJRWRDHSA-N 0.000 description 1
- HZZPIUMZUICXOU-OZHIHCJWSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@@H]12)[C@H]1c(cccc1)c1N[C@H]2c1ncc[nH]1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@@H]12)[C@H]1c(cccc1)c1N[C@H]2c1ncc[nH]1 HZZPIUMZUICXOU-OZHIHCJWSA-N 0.000 description 1
- MWTQPGQXZKADME-XIDUCYGFSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@@H]12)[C@H]1c1ccccc1N[C@H]2c1ncn[nH]1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@@H]12)[C@H]1c1ccccc1N[C@H]2c1ncn[nH]1 MWTQPGQXZKADME-XIDUCYGFSA-N 0.000 description 1
- HZZPIUMZUICXOU-ZEGVDLDJSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)C1c(cccc1)c1N[C@@H]2c1ncc[nH]1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)C1c(cccc1)c1N[C@@H]2c1ncc[nH]1 HZZPIUMZUICXOU-ZEGVDLDJSA-N 0.000 description 1
- MLOZCIGRIBBBJU-TZSGAMSQSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ccc[nH]1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ccc[nH]1 MLOZCIGRIBBBJU-TZSGAMSQSA-N 0.000 description 1
- MWTQPGQXZKADME-KHFRZORUSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ncn[nH]1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ncn[nH]1 MWTQPGQXZKADME-KHFRZORUSA-N 0.000 description 1
- FLUDLDSVPJPPFU-GJIXZQFMSA-N O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N1[C@H]2c3ccccc3N[C@@H](CNC(OCc3ccccc3)=O)[C@H]2CC1 Chemical compound O=C([C@@H](CCCC1)[C@@H]1NC(c1ccccc1)=O)N1[C@H]2c3ccccc3N[C@@H](CNC(OCc3ccccc3)=O)[C@H]2CC1 FLUDLDSVPJPPFU-GJIXZQFMSA-N 0.000 description 1
- NEUWQKDMBHDSAL-CGTJXYLNSA-N O=CN(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ccccc1 Chemical compound O=CN(CC[C@H]12)[C@@H]1c(cccc1)c1N[C@@H]2c1ccccc1 NEUWQKDMBHDSAL-CGTJXYLNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
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| JP4509080B2 (ja) * | 2006-09-28 | 2010-07-21 | 信越化学工業株式会社 | シルセスキオキサン系化合物混合物及び加水分解性シラン化合物、その製造方法及びそれを用いたレジスト組成物並びにパターン形成方法及び基板の加工方法 |
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| CA2694724C (en) * | 2007-08-01 | 2017-09-12 | University Health Network | Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer |
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| JP2013053070A (ja) * | 2009-11-06 | 2013-03-21 | Takeda Chem Ind Ltd | ジヒドロピロロキノリン誘導体 |
| EP2521545B1 (en) | 2010-01-07 | 2019-11-27 | Alkermes Pharma Ireland Limited | Prodrugs of heteroaromatic compounds |
| FR2974729B1 (fr) * | 2011-05-02 | 2013-04-19 | Servier Lab | Nouvelle association entre le 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide et un inhibiteur de l'acetylcholinesterase et les compositions pharmaceutiques qui la contiennent |
| EP2647638A1 (en) * | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Substituted tricyclic compounds with activity towards ep1 receptors |
| CN105017266B (zh) * | 2015-07-17 | 2017-07-18 | 安徽农业大学 | 手性2‑芳基‑1,2,3,4‑四氢喹啉类化合物及其合成方法 |
| SG11201806416XA (en) | 2016-02-12 | 2018-08-30 | Astellas Pharma Inc | Tetrahydroisoquinoline derivatives |
| US11787795B2 (en) | 2016-11-01 | 2023-10-17 | President And Fellows Of Harvard College | Inhibitors of RNA guided nucleases and uses thereof |
| US11352357B2 (en) | 2019-11-27 | 2022-06-07 | Sumitomo Dainippon Pharma Co., Ltd. | Cycloalkylurea derivative |
| CA3157769A1 (en) * | 2019-11-27 | 2021-06-03 | Eiji IDEUE | Cycloalkyl urea derivative |
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| US11739102B2 (en) | 2020-05-13 | 2023-08-29 | Incyte Corporation | Fused pyrimidine compounds as KRAS inhibitors |
| US11999752B2 (en) | 2020-08-28 | 2024-06-04 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of KRAS |
| US11767320B2 (en) | 2020-10-02 | 2023-09-26 | Incyte Corporation | Bicyclic dione compounds as inhibitors of KRAS |
| WO2022204112A1 (en) | 2021-03-22 | 2022-09-29 | Incyte Corporation | Imidazole and triazole kras inhibitors |
| MX2024000357A (es) | 2021-07-07 | 2024-02-12 | Incyte Corp | Compuestos triciclicos como inhibidores de homologo de oncogen viral de sarcoma de rata kirsten (kras). |
| WO2023287896A1 (en) | 2021-07-14 | 2023-01-19 | Incyte Corporation | Tricyclic compounds as inhibitors of kras |
| US11738021B2 (en) | 2021-08-23 | 2023-08-29 | Ckp Therapeutics, Inc. | Composition and method for preventing, alleviating or treating cancer |
| US12441742B2 (en) | 2021-08-31 | 2025-10-14 | Incyte Corporation | Naphthyridine compounds as inhibitors of KRAS |
| WO2023049697A1 (en) | 2021-09-21 | 2023-03-30 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of kras |
| CA3234375A1 (en) | 2021-10-01 | 2023-04-06 | Incyte Corporation | Pyrazoloquinoline kras inhibitors |
| CA3235146A1 (en) | 2021-10-14 | 2023-04-20 | Incyte Corporation | Quinoline compounds as inhibitors of kras |
| CN114524811B (zh) * | 2022-03-16 | 2025-01-24 | 中国人民解放军军事科学院军事医学研究院 | Lxh0307、lxh0308作为基因编辑的小分子抑制剂及其应用 |
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| WO1994009001A1 (en) * | 1992-10-15 | 1994-04-28 | Merck & Co., Inc. | Pyrroloquinoline bradykinin antagonist |
| RU2145606C1 (ru) * | 1994-05-24 | 2000-02-20 | Ф.Хоффманн-Ля Рош Аг | Трициклические дикарбонильные производные и лекарственный препарат на их основе |
| WO2002038547A1 (en) * | 2000-11-13 | 2002-05-16 | Glaxosmithkline Spa | Quinoline derivatives as nk-3 and nk-2 antagonists |
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| IT1283171B1 (it) | 1996-03-01 | 1998-04-16 | Interdipartimentale Di Ricerca | Composti solubili antagonisti delle tachichinine loro preparazione e loro uso in composizioni farmaceutiche |
| GB0027701D0 (en) | 2000-11-13 | 2000-12-27 | Smithkline Beecham Spa | Novel compounds |
| DE60209362T2 (de) | 2001-04-11 | 2006-10-26 | Glaxosmithkline S.P.A. | 3-substituierte chinolin-4-carbonsäureamidderivate als nk-3- und nk-2-rezeptorantagonisten |
| JP2004134705A (ja) | 2002-10-15 | 2004-04-30 | Jiaotong Univ | 金属酸化膜半導体電界効果トランジスタおよびそのゲート構造 |
| KR20070015598A (ko) * | 2004-04-28 | 2007-02-05 | 다케다 야쿠힌 고교 가부시키가이샤 | 융합 퀴놀린 유도체 및 이의 용도 |
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