CN103080106A - 用作激酶抑制剂的环醚化合物 - Google Patents
用作激酶抑制剂的环醚化合物 Download PDFInfo
- Publication number
- CN103080106A CN103080106A CN2011800335423A CN201180033542A CN103080106A CN 103080106 A CN103080106 A CN 103080106A CN 2011800335423 A CN2011800335423 A CN 2011800335423A CN 201180033542 A CN201180033542 A CN 201180033542A CN 103080106 A CN103080106 A CN 103080106A
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- China
- Prior art keywords
- alkyl
- compound
- amino
- equiv
- methyl
- 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.)
- Pending
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- 0 *C(C(NC(*)=O)=*)=**=* Chemical compound *C(C(NC(*)=O)=*)=**=* 0.000 description 16
- LFKDJXLFVYVEFG-UHFFFAOYSA-N CC(C)(C)OC(N)=O Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- ONVIACLNWQFOBK-UHFFFAOYSA-N CC(C)(C)[N](C)(C)C Chemical compound CC(C)(C)[N](C)(C)C ONVIACLNWQFOBK-UHFFFAOYSA-N 0.000 description 1
- OVQBFHCEJVOYQI-XBBDIZMDSA-N CC(C)(C)[SiH](C)O[C@@H](C[C@H](c(ccnc1)c1[N+]([O-])=O)OC1(C)C)[C@@H]1O Chemical compound CC(C)(C)[SiH](C)O[C@@H](C[C@H](c(ccnc1)c1[N+]([O-])=O)OC1(C)C)[C@@H]1O OVQBFHCEJVOYQI-XBBDIZMDSA-N 0.000 description 1
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- WIOOTLXLCLDKHK-UHFFFAOYSA-N CC(CC(F)=C1C2NC(C(O)=O)=CC=C2F)C=C1F Chemical compound CC(CC(F)=C1C2NC(C(O)=O)=CC=C2F)C=C1F WIOOTLXLCLDKHK-UHFFFAOYSA-N 0.000 description 1
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- JFFOTTSQJLRENT-UHFFFAOYSA-N CC1(C)OB(c(c(F)c(cc2)C(N(C)C)=O)c2F)OC1(C)C Chemical compound CC1(C)OB(c(c(F)c(cc2)C(N(C)C)=O)c2F)OC1(C)C JFFOTTSQJLRENT-UHFFFAOYSA-N 0.000 description 1
- IQFXJRXOTKFGPN-UHFFFAOYSA-N CCN(CC)C=C Chemical compound CCN(CC)C=C IQFXJRXOTKFGPN-UHFFFAOYSA-N 0.000 description 1
- MBBOTGYURVQWIF-UHFFFAOYSA-N CCOC(C1=CNC=C(c2ccccc2)C1=O)=O Chemical compound CCOC(C1=CNC=C(c2ccccc2)C1=O)=O MBBOTGYURVQWIF-UHFFFAOYSA-N 0.000 description 1
- BETFDCJHMAIVBA-FGRDXJNISA-N CC[C@@H](C(C)(C)[C@H](C1)OC(C)=O)OC1c(ccnc1)c1N Chemical compound CC[C@@H](C(C)(C)[C@H](C1)OC(C)=O)OC1c(ccnc1)c1N BETFDCJHMAIVBA-FGRDXJNISA-N 0.000 description 1
- JXIIMQNBQLSHOU-UPJWGTAASA-N CC[C@H]([C@H](C(C1)=O)O)O[C@H]1c1cc[n+](C)cc1[N+]([O-])=O Chemical compound CC[C@H]([C@H](C(C1)=O)O)O[C@H]1c1cc[n+](C)cc1[N+]([O-])=O JXIIMQNBQLSHOU-UPJWGTAASA-N 0.000 description 1
- UGHMFWGLAWDMBT-UHFFFAOYSA-N COC(c(cc(c(F)c1)Br)c1N)=[O]=C Chemical compound COC(c(cc(c(F)c1)Br)c1N)=[O]=C UGHMFWGLAWDMBT-UHFFFAOYSA-N 0.000 description 1
- LJCMMKJELAPZOV-NURSFMCSSA-N C[C@@H]1C[C@H](c(ccnc2)c2N)O[C@H](COC(C)=O)C1 Chemical compound C[C@@H]1C[C@H](c(ccnc2)c2N)O[C@H](COC(C)=O)C1 LJCMMKJELAPZOV-NURSFMCSSA-N 0.000 description 1
- GIQDCNUEJAQFKV-ZYOFANERSA-N C[C@H](C[C@H](c(ccnc1)c1N)O[C@@H]1C)[C@]1(CCCNCc1ccccc1)O Chemical compound C[C@H](C[C@H](c(ccnc1)c1N)O[C@@H]1C)[C@]1(CCCNCc1ccccc1)O GIQDCNUEJAQFKV-ZYOFANERSA-N 0.000 description 1
- SUVSELFSHADBRK-DNSOKLHBSA-N C[C@H]([C@@H](C)O[C@H](C1)c(ccnc2)c2[N+]([O-])=O)C1=O Chemical compound C[C@H]([C@@H](C)O[C@H](C1)c(ccnc2)c2[N+]([O-])=O)C1=O SUVSELFSHADBRK-DNSOKLHBSA-N 0.000 description 1
- KKSJFQHGMKIASG-JGMGGLLFSA-N C[C@H]([C@H](C)[C@H](c(ccnc1)c1N)O[C@@H]1C)[C@@H]1O Chemical compound C[C@H]([C@H](C)[C@H](c(ccnc1)c1N)O[C@@H]1C)[C@@H]1O KKSJFQHGMKIASG-JGMGGLLFSA-N 0.000 description 1
- UPHGJVUWCRGOKV-KDYMROGCSA-N C[C@H]([C@](C)([C@@H](C1)NC(OC(C)(C)C)=O)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)cc(C(N(C)C)=O)c2)c2F)c1F)=O Chemical compound C[C@H]([C@](C)([C@@H](C1)NC(OC(C)(C)C)=O)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)cc(C(N(C)C)=O)c2)c2F)c1F)=O UPHGJVUWCRGOKV-KDYMROGCSA-N 0.000 description 1
- RLCXIBVIZKXIJT-PTERYMMESA-N C[C@H]([C@](C)([C@@H]([C@H]1F)O[Si](C)(C)C(C)(C)C)O)O[C@H]1c(ccnc1)c1N Chemical compound C[C@H]([C@](C)([C@@H]([C@H]1F)O[Si](C)(C)C(C)(C)C)O)O[C@H]1c(ccnc1)c1N RLCXIBVIZKXIJT-PTERYMMESA-N 0.000 description 1
- HIAKCJKIVLUYBM-CQSZACIVSA-N C[Si+](C)(C)OC(C1)=CC2(CC2)O[C@H]1c(ccnc1)c1[N+]([O-])=O Chemical compound C[Si+](C)(C)OC(C1)=CC2(CC2)O[C@H]1c(ccnc1)c1[N+]([O-])=O HIAKCJKIVLUYBM-CQSZACIVSA-N 0.000 description 1
- MRPYPHHGUGOGSY-BHDDXSALSA-N N#CC[C@H]([C@H](CC1)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)ccc2)c2F)c1C#N)=O Chemical compound N#CC[C@H]([C@H](CC1)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)ccc2)c2F)c1C#N)=O MRPYPHHGUGOGSY-BHDDXSALSA-N 0.000 description 1
- LBASYCNGLJOSSX-PWRODBHTSA-N N#CC[C@H]([C@H](CC1)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)ccc2)c2F)c1F)=O Chemical compound N#CC[C@H]([C@H](CC1)O)O[C@H]1c(ccnc1)c1NC(c(cc1)nc(-c(c(F)ccc2)c2F)c1F)=O LBASYCNGLJOSSX-PWRODBHTSA-N 0.000 description 1
- PUKAYQCYGUDRAY-UHFFFAOYSA-N Nc1c(C2OCCCO2)ccnc1 Chemical compound Nc1c(C2OCCCO2)ccnc1 PUKAYQCYGUDRAY-UHFFFAOYSA-N 0.000 description 1
- JAOQUSFIYPHIMC-XCBNKYQSSA-N Nc1c([C@H](CC2)OC[C@@H]2O)ccnc1 Chemical compound Nc1c([C@H](CC2)OC[C@@H]2O)ccnc1 JAOQUSFIYPHIMC-XCBNKYQSSA-N 0.000 description 1
- FPAYBPUGCOPLJM-UHFFFAOYSA-N Nc1ccc(C2=NCCS2)nc1C(O)=O Chemical compound Nc1ccc(C2=NCCS2)nc1C(O)=O FPAYBPUGCOPLJM-UHFFFAOYSA-N 0.000 description 1
- WCRMEZPWARIASK-UHFFFAOYSA-N Nc1cnc(-c(cccc2)c2F)nc1C(O)O Chemical compound Nc1cnc(-c(cccc2)c2F)nc1C(O)O WCRMEZPWARIASK-UHFFFAOYSA-N 0.000 description 1
- AXXUKMYAQJKPMI-UHFFFAOYSA-N Nc1ncc(-c2ccccc2)nc1C(O)=O Chemical compound Nc1ncc(-c2ccccc2)nc1C(O)=O AXXUKMYAQJKPMI-UHFFFAOYSA-N 0.000 description 1
- GOHIYTWEZLRECD-UHFFFAOYSA-N [O-][N+](c(cncc1)c1C(C(F)(F)F)=O)=O Chemical compound [O-][N+](c(cncc1)c1C(C(F)(F)F)=O)=O GOHIYTWEZLRECD-UHFFFAOYSA-N 0.000 description 1
- CYMVNIANTHCYSU-UHFFFAOYSA-N [O-][N+](c1c(C(C2)(C(F)(F)F)OC=CC2=O)ccnc1)=O Chemical compound [O-][N+](c1c(C(C2)(C(F)(F)F)OC=CC2=O)ccnc1)=O CYMVNIANTHCYSU-UHFFFAOYSA-N 0.000 description 1
- QJUWWYDQJRXUDO-LDYMZIIASA-N [O-][N+](c1c([C@@H](C2)OC3(CC3)C[C@@H]2O)ccnc1)=O Chemical compound [O-][N+](c1c([C@@H](C2)OC3(CC3)C[C@@H]2O)ccnc1)=O QJUWWYDQJRXUDO-LDYMZIIASA-N 0.000 description 1
- DVXFDLWDPGTTSL-CYBMUJFWSA-N [O-][N+](c1c([C@@H](C2)OCCCCCC2=O)ccnc1)=O Chemical compound [O-][N+](c1c([C@@H](C2)OCCCCCC2=O)ccnc1)=O DVXFDLWDPGTTSL-CYBMUJFWSA-N 0.000 description 1
- UDQMAEUWUGSYAO-OASPWFOLSA-N [O-][N+](c1c([C@@H](C2)O[C@H](CCC3)[C@H]3C2=O)ccnc1)=O Chemical compound [O-][N+](c1c([C@@H](C2)O[C@H](CCC3)[C@H]3C2=O)ccnc1)=O UDQMAEUWUGSYAO-OASPWFOLSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
-
- 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36175510P | 2010-07-06 | 2010-07-06 | |
| US61/361,755 | 2010-07-06 | ||
| PCT/EP2011/061198 WO2012004217A1 (en) | 2010-07-06 | 2011-07-04 | Cyclic ether compounds useful as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103080106A true CN103080106A (zh) | 2013-05-01 |
Family
ID=44279730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011800335423A Pending CN103080106A (zh) | 2010-07-06 | 2011-07-04 | 用作激酶抑制剂的环醚化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20130109682A1 (https=) |
| EP (1) | EP2590968A1 (https=) |
| JP (1) | JP2013530199A (https=) |
| CN (1) | CN103080106A (https=) |
| WO (1) | WO2012004217A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106795151A (zh) * | 2014-08-06 | 2017-05-31 | 诺华股份有限公司 | 蛋白激酶c抑制剂和它们的使用方法 |
| CN110713476A (zh) * | 2019-11-07 | 2020-01-21 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-甲基-4h-吡喃-4-酮的合成方法 |
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| CN110790737A (zh) * | 2019-11-07 | 2020-02-14 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
| CN110790737B (zh) * | 2019-11-07 | 2022-07-22 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
| CN110713476B (zh) * | 2019-11-07 | 2022-07-26 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-甲基-4h-吡喃-4-酮的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012004217A1 (en) | 2012-01-12 |
| EP2590968A1 (en) | 2013-05-15 |
| US20130109682A1 (en) | 2013-05-02 |
| JP2013530199A (ja) | 2013-07-25 |
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