BR112013002182B8 - Compostos derivados de quinolina, composição farmacêutica, inibidor de melk, agente modulador de expressão de melk, agente antitumor, agente terapêutico e/ou preventivo para uma doença que envolve a superexpressão de melk contendo os mesmos e uso dos referidos compostos - Google Patents
Compostos derivados de quinolina, composição farmacêutica, inibidor de melk, agente modulador de expressão de melk, agente antitumor, agente terapêutico e/ou preventivo para uma doença que envolve a superexpressão de melk contendo os mesmos e uso dos referidos compostosInfo
- Publication number
- BR112013002182B8 BR112013002182B8 BR112013002182A BR112013002182A BR112013002182B8 BR 112013002182 B8 BR112013002182 B8 BR 112013002182B8 BR 112013002182 A BR112013002182 A BR 112013002182A BR 112013002182 A BR112013002182 A BR 112013002182A BR 112013002182 B8 BR112013002182 B8 BR 112013002182B8
- Authority
- BR
- Brazil
- Prior art keywords
- melk
- agent
- compounds
- same
- pharmaceutical composition
- Prior art date
Links
- 102100024299 Maternal embryonic leucine zipper kinase Human genes 0.000 title abstract 8
- 101710154611 Maternal embryonic leucine zipper kinase Proteins 0.000 title abstract 8
- 239000003795 chemical substances by application Substances 0.000 title abstract 4
- -1 QUINOLINE DERIVATIVE COMPOUNDS Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- DKZYXHCYPUVGAF-UHFFFAOYSA-N 1-[6-(3,5-dichloro-4-hydroxyphenyl)-4-[[4-[(dimethylamino)methyl]cyclohexyl]amino]-1,5-naphthyridin-3-yl]ethanone Chemical compound CN(C)CC1CCC(CC1)Nc1c(cnc2ccc(nc12)-c1cc(Cl)c(O)c(Cl)c1)C(C)=O DKZYXHCYPUVGAF-UHFFFAOYSA-N 0.000 title abstract 2
- 229940124787 MELK inhibitor Drugs 0.000 title abstract 2
- 239000002246 antineoplastic agent Substances 0.000 title abstract 2
- 201000010099 disease Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 230000014509 gene expression Effects 0.000 title abstract 2
- 230000002018 overexpression Effects 0.000 title abstract 2
- 230000003449 preventive effect Effects 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- 206010005003 Bladder cancer Diseases 0.000 abstract 1
- 206010006187 Breast cancer Diseases 0.000 abstract 1
- 208000026310 Breast neoplasm Diseases 0.000 abstract 1
- 206010008342 Cervix carcinoma Diseases 0.000 abstract 1
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 abstract 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 abstract 1
- 206010025323 Lymphomas Diseases 0.000 abstract 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 abstract 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 210000000481 breast Anatomy 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 230000003822 cell turnover Effects 0.000 abstract 1
- 201000010881 cervical cancer Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000013020 embryo development Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 210000004072 lung Anatomy 0.000 abstract 1
- 201000005202 lung cancer Diseases 0.000 abstract 1
- 208000020816 lung neoplasm Diseases 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 210000000130 stem cell Anatomy 0.000 abstract 1
- 210000003932 urinary bladder Anatomy 0.000 abstract 1
- 201000005112 urinary bladder cancer Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36951910P | 2010-07-30 | 2010-07-30 | |
| US61/369,519 | 2010-07-30 | ||
| PCT/US2011/045792 WO2012016082A1 (en) | 2010-07-30 | 2011-07-28 | Quinoline derivatives and melk inhibitors containing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BR112013002182A2 BR112013002182A2 (pt) | 2016-05-31 |
| BR112013002182B1 BR112013002182B1 (pt) | 2022-05-03 |
| BR112013002182B8 true BR112013002182B8 (pt) | 2023-02-28 |
Family
ID=45530500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112013002182A BR112013002182B8 (pt) | 2010-07-30 | 2011-07-28 | Compostos derivados de quinolina, composição farmacêutica, inibidor de melk, agente modulador de expressão de melk, agente antitumor, agente terapêutico e/ou preventivo para uma doença que envolve a superexpressão de melk contendo os mesmos e uso dos referidos compostos |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9120749B2 (https=) |
| EP (1) | EP2597955B1 (https=) |
| JP (1) | JP5849303B2 (https=) |
| KR (1) | KR101826382B1 (https=) |
| CN (1) | CN103153063B (https=) |
| AU (1) | AU2011282588B2 (https=) |
| BR (1) | BR112013002182B8 (https=) |
| CA (1) | CA2806332C (https=) |
| DK (1) | DK2597955T3 (https=) |
| ES (1) | ES2565627T3 (https=) |
| IL (1) | IL223871A (https=) |
| MX (1) | MX342879B (https=) |
| RU (1) | RU2582610C2 (https=) |
| SG (2) | SG10201505951VA (https=) |
| TW (1) | TWI532483B (https=) |
| WO (1) | WO2012016082A1 (https=) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130225524A1 (en) * | 2010-11-05 | 2013-08-29 | Deping Chai | Chemical Compounds |
| WO2013109388A2 (en) * | 2012-01-19 | 2013-07-25 | Oncotherapy Science, Inc. | 1,5-naphthyridine derivatives and melk inhibitors containing the same |
| US9745319B2 (en) | 2013-03-15 | 2017-08-29 | Araxes Pharma Llc | Irreversible covalent inhibitors of the GTPase K-Ras G12C |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| US10254283B2 (en) | 2013-11-12 | 2019-04-09 | Dana-Farber Cancer Institute, Inc. | Biomarker for MELK activity and methods of using same |
| US9840489B2 (en) | 2013-12-20 | 2017-12-12 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | Piperidine carboxamide compound, preparation method, and usage thereof |
| JO3556B1 (ar) | 2014-09-18 | 2020-07-05 | Araxes Pharma Llc | علاجات مدمجة لمعالجة السرطان |
| JP2017528498A (ja) | 2014-09-25 | 2017-09-28 | アラクセス ファーマ エルエルシー | Kras g12c変異体タンパク質のインヒビター |
| WO2016049568A1 (en) | 2014-09-25 | 2016-03-31 | Araxes Pharma Llc | Methods and compositions for inhibition of ras |
| NZ732511A (en) * | 2014-12-15 | 2018-11-30 | Univ Michigan Regents | Small molecule inhibitors of egfr and pi3k |
| WO2016141296A1 (en) | 2015-03-04 | 2016-09-09 | Dana-Farber Caner Institute, Inc. | Tricyclic kinase inhibitors of melk and methods of use |
| ES2898765T3 (es) | 2015-04-10 | 2022-03-08 | Araxes Pharma Llc | Compuestos de quinazolina sustituidos y métodos de uso de los mismos |
| US10428064B2 (en) | 2015-04-15 | 2019-10-01 | Araxes Pharma Llc | Fused-tricyclic inhibitors of KRAS and methods of use thereof |
| WO2017015562A1 (en) * | 2015-07-22 | 2017-01-26 | Araxes Pharma Llc | Substituted quinazoline compounds and their use as inhibitors of g12c mutant kras, hras and/or nras proteins |
| CN108026046B (zh) * | 2015-07-22 | 2021-12-21 | 亚瑞克西斯制药公司 | 取代的喹唑啉化合物及其作为g12c突变体kras、hras和/或nras蛋白质的抑制剂的用途 |
| US10144724B2 (en) | 2015-07-22 | 2018-12-04 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use thereof |
| EA033686B1 (ru) * | 2015-08-03 | 2019-11-15 | Bristol Myers Squibb Co | Гетероциклические соединения, применимые в качестве модуляторов tnf-альфа |
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| EP3356351A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| EP3356359B1 (en) | 2015-09-28 | 2021-10-20 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| EP3356349A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058902A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| WO2017058805A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| WO2017070256A2 (en) | 2015-10-19 | 2017-04-27 | Araxes Pharma Llc | Method for screening inhibitors of ras |
| KR20180081596A (ko) | 2015-11-16 | 2018-07-16 | 아락세스 파마 엘엘씨 | 치환된 헤테로사이클릭 그룹을 포함하는 2-치환된 퀴나졸린 화합물 및 이의 사용 방법 |
| US9988357B2 (en) | 2015-12-09 | 2018-06-05 | Araxes Pharma Llc | Methods for preparation of quinazoline derivatives |
| AU2016378579A1 (en) * | 2015-12-22 | 2018-06-14 | Vitae Pharmaceuticals, Inc. | Inhibitors of the menin-MLL interaction |
| WO2017172979A1 (en) | 2016-03-30 | 2017-10-05 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use |
| US10646488B2 (en) | 2016-07-13 | 2020-05-12 | Araxes Pharma Llc | Conjugates of cereblon binding compounds and G12C mutant KRAS, HRAS or NRAS protein modulating compounds and methods of use thereof |
| IL264178B2 (en) | 2016-07-14 | 2024-05-01 | Crinetics Pharmaceuticals Inc | Somatostatin modulators and uses thereof |
| RU2756982C2 (ru) | 2016-08-31 | 2021-10-07 | Онкотерапи Сайенс, Инк. | Моноклональное антитело против melk и его использование |
| WO2018064510A1 (en) | 2016-09-29 | 2018-04-05 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3523289A1 (en) | 2016-10-07 | 2019-08-14 | Araxes Pharma LLC | Heterocyclic compounds as inhibitors of ras and methods of use thereof |
| PL3558321T3 (pl) * | 2016-12-23 | 2023-10-23 | Felicitex Therapeutics, Inc. | Pochodne chinolin jako inhibitory kinaz dyrk1a i/lub dyrk1b |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
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| CN109651355A (zh) * | 2019-01-24 | 2019-04-19 | 广西师范大学 | 3-(2-苯并五元杂环)-4-(3-二甲胺丙氨基)喹啉衍生物及其制备方法和应用 |
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| CA2806332C (en) | 2017-11-14 |
| JP2013532727A (ja) | 2013-08-19 |
| US9120749B2 (en) | 2015-09-01 |
| AU2011282588A1 (en) | 2013-03-21 |
| WO2012016082A1 (en) | 2012-02-02 |
| EP2597955A4 (en) | 2014-02-19 |
| JP5849303B2 (ja) | 2016-01-27 |
| ES2565627T3 (es) | 2016-04-06 |
| TWI532483B (zh) | 2016-05-11 |
| BR112013002182A2 (pt) | 2016-05-31 |
| IL223871A (en) | 2016-11-30 |
| CN103153063B (zh) | 2016-02-17 |
| KR20130094312A (ko) | 2013-08-23 |
| EP2597955B1 (en) | 2016-01-20 |
| HK1184331A1 (zh) | 2014-01-24 |
| BR112013002182B1 (pt) | 2022-05-03 |
| US20130217671A1 (en) | 2013-08-22 |
| EP2597955A1 (en) | 2013-06-05 |
| CN103153063A (zh) | 2013-06-12 |
| AU2011282588B2 (en) | 2016-01-07 |
| CA2806332A1 (en) | 2012-02-02 |
| DK2597955T3 (en) | 2016-03-14 |
| TW201208686A (en) | 2012-03-01 |
| MX2013001201A (es) | 2013-04-03 |
| RU2582610C2 (ru) | 2016-04-27 |
| RU2013108865A (ru) | 2014-09-10 |
| SG10201505951VA (en) | 2015-08-28 |
| KR101826382B1 (ko) | 2018-02-06 |
| SG187633A1 (en) | 2013-03-28 |
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