JP2010529196A - アザペプチド誘導体 - Google Patents
アザペプチド誘導体 Download PDFInfo
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- JP2010529196A JP2010529196A JP2010512186A JP2010512186A JP2010529196A JP 2010529196 A JP2010529196 A JP 2010529196A JP 2010512186 A JP2010512186 A JP 2010512186A JP 2010512186 A JP2010512186 A JP 2010512186A JP 2010529196 A JP2010529196 A JP 2010529196A
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- JP
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- Prior art keywords
- compound
- pharmaceutically acceptable
- efavirenz
- composition
- compounds
- Prior art date
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 55
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- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 22
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- 239000012217 radiopharmaceutical Substances 0.000 description 1
- 229940121896 radiopharmaceutical Drugs 0.000 description 1
- 230000002799 radiopharmaceutical effect Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
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- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- VEMKTZHHVJILDY-UHFFFAOYSA-N resmethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960004556 tenofovir Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- NVPOUMXZERMIJK-STQMWFEESA-N tert-butyl n-[(1s)-1-[(2r)-oxiran-2-yl]-2-phenylethyl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H]1OC1)C1=CC=CC=C1 NVPOUMXZERMIJK-STQMWFEESA-N 0.000 description 1
- GIMJTKJSKPENNG-UHFFFAOYSA-N tert-butyl n-[(4-pyridin-2-ylphenyl)methylamino]carbamate Chemical compound C1=CC(CNNC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=N1 GIMJTKJSKPENNG-UHFFFAOYSA-N 0.000 description 1
- PIYYEQIVVRRORO-XDHOZWIPSA-N tert-butyl n-[(e)-(4-pyridin-2-ylphenyl)methylideneamino]carbamate Chemical compound C1=CC(/C=N/NC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=N1 PIYYEQIVVRRORO-XDHOZWIPSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine 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)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93420107P | 2007-06-12 | 2007-06-12 | |
| US6762708P | 2008-02-29 | 2008-02-29 | |
| PCT/US2008/007331 WO2008156632A1 (en) | 2007-06-12 | 2008-06-12 | Azapeptide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010529196A true JP2010529196A (ja) | 2010-08-26 |
| JP2010529196A5 JP2010529196A5 (Direct) | 2011-08-04 |
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| JP2010512186A Pending JP2010529196A (ja) | 2007-06-12 | 2008-06-12 | アザペプチド誘導体 |
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|---|---|
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| EP (3) | EP2003120B9 (Direct) |
| JP (1) | JP2010529196A (Direct) |
| KR (2) | KR101185899B1 (Direct) |
| CN (2) | CN102424668A (Direct) |
| AR (1) | AR066972A1 (Direct) |
| AT (2) | ATE447554T1 (Direct) |
| AU (1) | AU2008267048C1 (Direct) |
| BR (2) | BRPI0813911A2 (Direct) |
| CA (1) | CA2692028C (Direct) |
| CO (1) | CO6241121A2 (Direct) |
| CY (1) | CY1109766T1 (Direct) |
| DE (1) | DE602008000255D1 (Direct) |
| DK (1) | DK2003120T3 (Direct) |
| ES (3) | ES2394952T3 (Direct) |
| HR (1) | HRP20100065T1 (Direct) |
| MX (1) | MX2009013565A (Direct) |
| PL (1) | PL2003120T3 (Direct) |
| PT (1) | PT2003120E (Direct) |
| RS (1) | RS51226B (Direct) |
| RU (2) | RU2448958C2 (Direct) |
| SI (1) | SI2003120T1 (Direct) |
| TW (1) | TW200908970A (Direct) |
| WO (1) | WO2008156632A1 (Direct) |
| ZA (1) | ZA200909079B (Direct) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2021529765A (ja) * | 2018-06-29 | 2021-11-04 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | Ａｘｌ／ｍｅｒ阻害剤の製剤 |
| US12187730B2 (en) | 2017-09-27 | 2025-01-07 | Incyte Corporation | Salts of TAM inhibitors |
| US12214036B2 (en) | 2020-03-06 | 2025-02-04 | Incyte Corporation | Combination therapy comprising AXL/MER and PD-1/PD-L1 inhibitors |
| US12415809B2 (en) | 2016-03-28 | 2025-09-16 | Incyte Corporation | Pyrrolotriazine compounds as tam inhibitors |
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| WO2008103899A1 (en) * | 2007-02-23 | 2008-08-28 | Auspex Pharmaceuticals, Inc. | Preparation and utility of non-nucleoside reverse transcriptase inhibitors |
| BRPI0813911A2 (pt) | 2007-06-12 | 2012-02-22 | Concert Pharmaceuticals Inc. | Composto derivado de azapeptídeos e composição farmacêutica contendo o mesmo |
| WO2010041241A2 (en) * | 2008-10-06 | 2010-04-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Hiv-1 integrase derived peptides and compositions |
| WO2010132663A1 (en) * | 2009-05-13 | 2010-11-18 | Concert Pharmaceticals, Inc. | Pegylated azapeptide derivatives as hiv protease inhibitors |
| WO2010135424A1 (en) * | 2009-05-19 | 2010-11-25 | Glaxosmithkline Llc | Chemical compounds |
| ES2600878T3 (es) | 2009-12-21 | 2017-02-13 | Janssen Sciences Ireland Uc | Implante removible, degradable, para la liberación prolongada de un compuesto activo |
| WO2011080562A1 (en) | 2009-12-29 | 2011-07-07 | Hetero Research Foundation | Novel aza-peptides containing 2,2-disubstituted cyclobutyl and/or substituted alkoxy benzyl derivatives as antivirals |
| RS58546B1 (sr) | 2011-06-20 | 2019-05-31 | H Lundbeck As | Deuterizovani 1-piperazino-3-fenil indani za tretiranje šizofrenije |
| CN106543073A (zh) * | 2015-09-17 | 2017-03-29 | 宁波杰尔盛化工有限公司 | 2-[4-（2-吡啶基）苄基]-肼羧酸叔丁酯的制备方法 |
| HRP20211687T1 (hr) * | 2015-12-02 | 2022-03-04 | Merck Sharp & Dohme Corp. | Farmaceutske kompozicije koje sadrže doravirin, tenofovir dizoproksil fumarat i lamivudin |
| JOP20180009A1 (ar) | 2017-02-06 | 2019-01-30 | Gilead Sciences Inc | مركبات مثبط فيروس hiv |
| WO2019025250A1 (en) | 2017-08-04 | 2019-02-07 | Basf Se | SUBSTITUTED TRIFLUOROMETHYLOXADIAZOLES FOR COMBATING PHYTOPATHOGENIC FUNGI |
| TWI766172B (zh) | 2018-07-30 | 2022-06-01 | 美商基利科學股份有限公司 | 抗hiv化合物 |
| AU2021257341A1 (en) * | 2020-04-16 | 2022-11-17 | The Medical College Of Wisconsin, Inc. | Aerosolized formulations of HIV protease inhibitors for the treatment of airway reflux |
| CN115583984A (zh) * | 2022-01-11 | 2023-01-10 | 嘉兴安谛康生物科技有限公司 | 氮杂螺类化合物及其制备方法、药物组合物和用途 |
| US20250051375A1 (en) | 2023-05-31 | 2025-02-13 | Gilead Sciences, Inc. | Anti-hiv compounds |
| CN116987024A (zh) * | 2023-08-01 | 2023-11-03 | 浙江荣耀生物科技股份有限公司 | 一种阿扎那韦中间体的制备方法 |
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| WO2006014282A2 (en) * | 2004-07-06 | 2006-02-09 | Abbott Laboratories | Prodrugs of hiv protease inhibitors |
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| US12415809B2 (en) | 2016-03-28 | 2025-09-16 | Incyte Corporation | Pyrrolotriazine compounds as tam inhibitors |
| US12187730B2 (en) | 2017-09-27 | 2025-01-07 | Incyte Corporation | Salts of TAM inhibitors |
| JP2021529765A (ja) * | 2018-06-29 | 2021-11-04 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | Ａｘｌ／ｍｅｒ阻害剤の製剤 |
| US11918585B2 (en) | 2018-06-29 | 2024-03-05 | Incyte Corporation | Formulations of an AXL/MER inhibitor |
| JP7520732B2 (ja) | 2018-06-29 | 2024-07-23 | インサイト・コーポレイション | Ａｘｌ／ｍｅｒ阻害剤の製剤 |
| JP2024147640A (ja) * | 2018-06-29 | 2024-10-16 | インサイト・コーポレイション | Ａｘｌ／ｍｅｒ阻害剤の製剤 |
| US12318389B2 (en) | 2018-06-29 | 2025-06-03 | Incyte Corporation | Formulations of an AXL/MER inhibitor |
| JP7753463B2 (ja) | 2018-06-29 | 2025-10-14 | インサイト・コーポレイション | Ａｘｌ／ｍｅｒ阻害剤の製剤 |
| US12214036B2 (en) | 2020-03-06 | 2025-02-04 | Incyte Corporation | Combination therapy comprising AXL/MER and PD-1/PD-L1 inhibitors |
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