CN104447657B - 具有抗肿瘤活性的色烯酮衍生物 - Google Patents
具有抗肿瘤活性的色烯酮衍生物 Download PDFInfo
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- CN104447657B CN104447657B CN201410654983.0A CN201410654983A CN104447657B CN 104447657 B CN104447657 B CN 104447657B CN 201410654983 A CN201410654983 A CN 201410654983A CN 104447657 B CN104447657 B CN 104447657B
- Authority
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- China
- Prior art keywords
- chromene
- ethyl
- oxo
- morpholino
- compound
- 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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- 0 *Cc1c(C*)c(OC(c2ccccc2)=O)c(*)c(*)c1* Chemical compound *Cc1c(C*)c(OC(c2ccccc2)=O)c(*)c(*)c1* 0.000 description 3
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- JDEUJLRKKLWIRM-UHFFFAOYSA-N CC(C(C(OC(N1CCOCC1)=C1)=C(C2)C1=[U])=CC2C(N(C)C)=O)=O Chemical compound CC(C(C(OC(N1CCOCC1)=C1)=C(C2)C1=[U])=CC2C(N(C)C)=O)=O JDEUJLRKKLWIRM-UHFFFAOYSA-N 0.000 description 1
- FFISUGJJSCPMLM-UHFFFAOYSA-N CC(C(CC(C(N(C)C)=O)=C1)C(OC(N2CCOCC2)=C2)=C1C2=[U])Nc(cc1)ccc1F Chemical compound CC(C(CC(C(N(C)C)=O)=C1)C(OC(N2CCOCC2)=C2)=C1C2=[U])Nc(cc1)ccc1F FFISUGJJSCPMLM-UHFFFAOYSA-N 0.000 description 1
- UUIQQNYNMJPESN-UHFFFAOYSA-N CC(c(cc(cc12)C(N(C)C)=O)c1OC(N1CCOCC1)=CC2=O)Nc1cc(Cl)ccc1C Chemical compound CC(c(cc(cc12)C(N(C)C)=O)c1OC(N1CCOCC1)=CC2=O)Nc1cc(Cl)ccc1C UUIQQNYNMJPESN-UHFFFAOYSA-N 0.000 description 1
- CRLMTNXLTUSOPJ-UHFFFAOYSA-N CC(c(cc(cc12)C(O)=O)c1OC(N1CCOCC1)=CC2=O)=O Chemical compound CC(c(cc(cc12)C(O)=O)c1OC(N1CCOCC1)=CC2=O)=O CRLMTNXLTUSOPJ-UHFFFAOYSA-N 0.000 description 1
- MDHQZDJGSZVTDR-UHFFFAOYSA-N CC(c1cc(C(N(C)C)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cc(cc1)F)c1F Chemical compound CC(c1cc(C(N(C)C)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cc(cc1)F)c1F MDHQZDJGSZVTDR-UHFFFAOYSA-N 0.000 description 1
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- ADXXTOWOZCJPQZ-PXYINDEMSA-N CC(c1cc(C(N(C)C)=O)cc2c1OC(N1C[C@H](C)OCC1)=CC2=O)Br Chemical compound CC(c1cc(C(N(C)C)=O)cc2c1OC(N1C[C@H](C)OCC1)=CC2=O)Br ADXXTOWOZCJPQZ-PXYINDEMSA-N 0.000 description 1
- GMWIXYJWVBNHHV-VYRBHSGPSA-N CC(c1cc(C(N(C)C)=O)cc2c1OC(N1C[C@H](C)OCC1)=CC2=O)Nc(cc1)ccc1F Chemical compound CC(c1cc(C(N(C)C)=O)cc2c1OC(N1C[C@H](C)OCC1)=CC2=O)Nc(cc1)ccc1F GMWIXYJWVBNHHV-VYRBHSGPSA-N 0.000 description 1
- UOZWDNWNBWHNIU-UHFFFAOYSA-N CC(c1cc(C(N(CC2)CCC2O)=O)cc2c1OC(N1CCOCC1)=CC2=O)N(C)c1cc(F)cc(F)c1 Chemical compound CC(c1cc(C(N(CC2)CCC2O)=O)cc2c1OC(N1CCOCC1)=CC2=O)N(C)c1cc(F)cc(F)c1 UOZWDNWNBWHNIU-UHFFFAOYSA-N 0.000 description 1
- QWELDBADLWQWPE-UHFFFAOYSA-N CC(c1cc(C(N(CC2)CCC2O)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cccc1Cl)c1F Chemical compound CC(c1cc(C(N(CC2)CCC2O)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cccc1Cl)c1F QWELDBADLWQWPE-UHFFFAOYSA-N 0.000 description 1
- GGAFSGSDUHLION-UHFFFAOYSA-N CC(c1cc(C(N(CC2)CCC2OC(C(C(C)(C)C)c2ccccc2)c2ccccc2)=O)cc2c1OC(N1CCOCC1)=CC2=O)N(C)c1cc(F)cc(F)c1 Chemical compound CC(c1cc(C(N(CC2)CCC2OC(C(C(C)(C)C)c2ccccc2)c2ccccc2)=O)cc2c1OC(N1CCOCC1)=CC2=O)N(C)c1cc(F)cc(F)c1 GGAFSGSDUHLION-UHFFFAOYSA-N 0.000 description 1
- MIIUCQQOKMDLDH-UHFFFAOYSA-N CC(c1cc(C(O)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cccc1Cl)c1F Chemical compound CC(c1cc(C(O)=O)cc2c1OC(N1CCOCC1)=CC2=O)Nc(cccc1Cl)c1F MIIUCQQOKMDLDH-UHFFFAOYSA-N 0.000 description 1
- CMKUQYFGGFUXTG-CBCUQQMYSA-N CC(c1cc(C(OC)=O)cc2c1OC(N1[C@@H](C)COCC1)=CC2=O)NC(C1)=CC(F)=CC1F Chemical compound CC(c1cc(C(OC)=O)cc2c1OC(N1[C@@H](C)COCC1)=CC2=O)NC(C1)=CC(F)=CC1F CMKUQYFGGFUXTG-CBCUQQMYSA-N 0.000 description 1
- GVSMCIMUFWNFGS-UHFFFAOYSA-N CCS(C(OC1C2=CC(C(OC)=O)=CC1C(C)Nc1cc([I]=C)cc([FH+])c1)=CC2=O)=O Chemical compound CCS(C(OC1C2=CC(C(OC)=O)=CC1C(C)Nc1cc([I]=C)cc([FH+])c1)=CC2=O)=O GVSMCIMUFWNFGS-UHFFFAOYSA-N 0.000 description 1
- USOBLPBXNCSJAQ-UHFFFAOYSA-N CCSC(Oc(c(Br)c1)c2cc1C([U]C)=O)=CC2=O Chemical compound CCSC(Oc(c(Br)c1)c2cc1C([U]C)=O)=CC2=O USOBLPBXNCSJAQ-UHFFFAOYSA-N 0.000 description 1
- HARBVWHVQRDBJR-BHWOMJMDSA-N CCc1cc(NC(C)c2cc(C(N(C)C)=O)cc3c2OC(N2[C@@H](C)COCC2)=CC3=O)cc(F)c1 Chemical compound CCc1cc(NC(C)c2cc(C(N(C)C)=O)cc3c2OC(N2[C@@H](C)COCC2)=CC3=O)cc(F)c1 HARBVWHVQRDBJR-BHWOMJMDSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09306017.6 | 2009-10-27 | ||
| EP09306017 | 2009-10-27 | ||
| CN201080060262.7A CN102712615B (zh) | 2009-10-27 | 2010-10-25 | 具有抗肿瘤活性的色烯酮衍生物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080060262.7A Division CN102712615B (zh) | 2009-10-27 | 2010-10-25 | 具有抗肿瘤活性的色烯酮衍生物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104447657A CN104447657A (zh) | 2015-03-25 |
| CN104447657B true CN104447657B (zh) | 2016-08-17 |
Family
ID=43085922
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410654983.0A Expired - Fee Related CN104447657B (zh) | 2009-10-27 | 2010-10-25 | 具有抗肿瘤活性的色烯酮衍生物 |
| CN201080060262.7A Expired - Fee Related CN102712615B (zh) | 2009-10-27 | 2010-10-25 | 具有抗肿瘤活性的色烯酮衍生物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080060262.7A Expired - Fee Related CN102712615B (zh) | 2009-10-27 | 2010-10-25 | 具有抗肿瘤活性的色烯酮衍生物 |
Country Status (41)
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8415376B2 (en) | 2008-05-30 | 2013-04-09 | Amgen Inc. | Inhibitors of PI3 kinase |
| US8399460B2 (en) * | 2009-10-27 | 2013-03-19 | Astrazeneca Ab | Chromenone derivatives |
| UY34013A (es) * | 2011-04-13 | 2012-11-30 | Astrazeneca Ab | ?compuestos de cromenona con actividad anti-tumoral?. |
| PE20151979A1 (es) | 2013-01-23 | 2016-01-15 | Astrazeneca Ab | Compuestos quimicos |
| MX362905B (es) | 2013-03-04 | 2019-02-25 | Astrazeneca Ab | Tratamiento de combinacion. |
| BR112016028876A2 (pt) | 2014-06-13 | 2017-08-22 | Gilead Sciences Inc | composto, composição farmacêutica, método para tratar uma doença ou condição em um ser humano, kit, e, uso de um composto, um sal, isômero ou uma mistura farmaceuticamente aceitável dos mesmos. |
| JP6454736B2 (ja) | 2014-06-13 | 2019-01-16 | ギリアード サイエンシーズ, インコーポレイテッド | ホスファチジルイノシトール3−キナーゼ阻害剤 |
| WO2015191754A2 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| ES2763103T3 (es) | 2014-06-13 | 2020-05-27 | Gilead Sciences Inc | Inhibidor de la fosfatidilinositol 3-quinasa |
| CN106459005A (zh) | 2014-06-13 | 2017-02-22 | 吉利德科学公司 | 磷脂酰肌醇3‑激酶抑制剂 |
| CN104803921A (zh) * | 2015-03-14 | 2015-07-29 | 长沙深橙生物科技有限公司 | 一种苯取代嘧啶衍生物的制备方法 |
| CN104744376A (zh) * | 2015-03-14 | 2015-07-01 | 长沙深橙生物科技有限公司 | 一种2-异丙基嘧啶衍生物的制备方法 |
| KR101766731B1 (ko) | 2015-06-23 | 2017-08-10 | 충남대학교산학협력단 | 강심 활성을 갖는 크로메논 유도체 및 이를 포함하는 심부전의 예방 또는 치료용 약학 조성물 |
| BR112018007068B1 (pt) * | 2015-10-09 | 2024-01-02 | Janssen Pharmaceutica N.V. | Derivados de quinoxalina e piridopirazina como inibidores de pi3kbeta, seu uso e composição farmacêutica que os compreende |
| WO2018057808A1 (en) | 2016-09-23 | 2018-03-29 | Gilead Sciences, Inc. | Benzimidazole derivatives and their use as phosphatidylinositol 3-kinase inhibitors |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| AR121719A1 (es) * | 2020-04-03 | 2022-06-29 | Petra Pharma Corp | Inhibidores alostéricos de cromenona del fosfoinosítido 3-quinasa (pi3k) para el tratamiento de enfermedades |
| KR20210141214A (ko) * | 2020-05-15 | 2021-11-23 | 제이투에이치바이오텍 (주) | 3원환 화합물 및 이의 의약 용도 |
| IL304895A (en) * | 2021-02-01 | 2023-10-01 | Geode Therapeutics Inc | INHIBITORS OF PHOSPHOINOSITIDE 3 KINASE BETA Preparations containing them and their use for treatment |
| MX2023013080A (es) * | 2021-05-03 | 2023-11-16 | Petra Pharma Corp | Inhibidores alostericos de cromenona del fosfoinositido 3-quinasa (pi3k) para el tratamiento de enfermedades. |
| JP7759964B2 (ja) * | 2021-05-03 | 2025-10-24 | ペトラ・ファーマ・コーポレイション | 疾患の治療のためのホスホイノシチド3-キナーゼ(pi3k)のアロステリッククロメノン阻害剤 |
| WO2022251482A1 (en) * | 2021-05-27 | 2022-12-01 | Petra Pharma Corporation | Allosteric chromenone inhibitors of phosphoinositide 3-kinase (pi3k) for the treatment of cancer |
| TW202329930A (zh) * | 2021-09-30 | 2023-08-01 | 美商佩特拉製藥公司 | 用於治療疾病之磷酸肌醇3-激酶(pi3k)之異位色烯酮抑制劑 |
| CA3232906A1 (en) * | 2021-10-07 | 2023-04-13 | Alessandro Boezio | Pi3k-alpha inhibitors and methods of use thereof |
| CA3237760A1 (en) * | 2021-12-08 | 2023-06-15 | Xiaolin Hao | Fused heterocyclic compounds as pi3kalpha inhibitors |
| WO2024003241A1 (en) | 2022-06-30 | 2024-01-04 | Astrazeneca Ab | Treatment for immuno-oncology resistant subjects with an anti pd-l1 antibody an antisense targeted to stat3 and an inhibitor of ctla-4 |
| EP4602031A1 (en) * | 2022-10-14 | 2025-08-20 | Genesis Therapeutics, Inc. | Methods for treating cancer |
| CN119431297A (zh) * | 2023-08-02 | 2025-02-14 | 郑州同源康医药有限公司 | 稠环类化合物及其用途 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6027A (en) * | 1849-01-09 | Rotary blacksmith s twyer | ||
| AU634994B2 (en) | 1988-12-21 | 1993-03-11 | Pharmacia & Upjohn Company | Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones |
| DK0525123T3 (da) | 1990-06-20 | 1998-05-04 | Upjohn Co | Antiatherosklerotiske og antithrombotiske 1-benzopyran-4-oner og 2-amino-1,3-benzoxazin-4-oner |
| DE4318756A1 (de) | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
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