CN108290856A - 芳基-取代的二氢喹诺酮、它们的制备和它们作为药物的用途 - Google Patents
芳基-取代的二氢喹诺酮、它们的制备和它们作为药物的用途 Download PDFInfo
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- CN108290856A CN108290856A CN201680058648.1A CN201680058648A CN108290856A CN 108290856 A CN108290856 A CN 108290856A CN 201680058648 A CN201680058648 A CN 201680058648A CN 108290856 A CN108290856 A CN 108290856A
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- 0 *c1c(*CC(N2*)=O)c2ccc1C(C(*)=C1*)=C(*)N(*)C1=O Chemical compound *c1c(*CC(N2*)=O)c2ccc1C(C(*)=C1*)=C(*)N(*)C1=O 0.000 description 14
- DZINQZRQWWHLRI-UYTHXWSBSA-N C/C(/CBr)=C(/C)\C=C(\CNC(CC1)OC)/C1=C Chemical compound C/C(/CBr)=C(/C)\C=C(\CNC(CC1)OC)/C1=C DZINQZRQWWHLRI-UYTHXWSBSA-N 0.000 description 1
- ASKNNJWNWKHDKP-IQXIVLSVSA-N C/C=C(\C=C(\C)/C(NC)=O)/c(cc1CC2)cc(OCc3nccnc3)c1NC2=O Chemical compound C/C=C(\C=C(\C)/C(NC)=O)/c(cc1CC2)cc(OCc3nccnc3)c1NC2=O ASKNNJWNWKHDKP-IQXIVLSVSA-N 0.000 description 1
- RBLLQQMDOJCNOQ-UHFFFAOYSA-N CC(CC/C(/N1)=[O]\Cc2ccc(CCC(N3)=O)c3c2OCOC)(CC=C2)C1=C2O Chemical compound CC(CC/C(/N1)=[O]\Cc2ccc(CCC(N3)=O)c3c2OCOC)(CC=C2)C1=C2O RBLLQQMDOJCNOQ-UHFFFAOYSA-N 0.000 description 1
- QDUXYTNDTIGHGF-UHFFFAOYSA-N CC(NC(CC1)=O)=C1C=C Chemical compound CC(NC(CC1)=O)=C1C=C QDUXYTNDTIGHGF-UHFFFAOYSA-N 0.000 description 1
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- QAPJXXGCRDCITL-UHFFFAOYSA-N CC(c1cccnc1)Oc(cc(cc1CC2)C(C=C3C)=CN(C)C3=O)c1NC2=O Chemical compound CC(c1cccnc1)Oc(cc(cc1CC2)C(C=C3C)=CN(C)C3=O)c1NC2=O QAPJXXGCRDCITL-UHFFFAOYSA-N 0.000 description 1
- HHIIXLISVXVTKF-UHFFFAOYSA-N CC1(C)OB(c2c(C)cc(C)c(CCC(N)=O)c2)OC1(C)C Chemical compound CC1(C)OB(c2c(C)cc(C)c(CCC(N)=O)c2)OC1(C)C HHIIXLISVXVTKF-UHFFFAOYSA-N 0.000 description 1
- MPLOWUYGVOAPFK-ZHACJKMWSA-N CC1=CC(/C=C/C(C=C2)=C(C(N(C)Cc3ccccc3)=C)NC2=O)=CN(C)C1=O Chemical compound CC1=CC(/C=C/C(C=C2)=C(C(N(C)Cc3ccccc3)=C)NC2=O)=CN(C)C1=O MPLOWUYGVOAPFK-ZHACJKMWSA-N 0.000 description 1
- BJALCMYDJRISAE-UHFFFAOYSA-N CC1=CC(C2=CCC(CCC(N3)=O)C3=C2Cc2ccccc2)=CN(C)C1=O Chemical compound CC1=CC(C2=CCC(CCC(N3)=O)C3=C2Cc2ccccc2)=CN(C)C1=O BJALCMYDJRISAE-UHFFFAOYSA-N 0.000 description 1
- FZTVMAGQAZHPHW-UHFFFAOYSA-N CC1=CC(c(cc2CC3)cc(NCc4ccccc4)c2NC3=O)=CN(C)C1=O Chemical compound CC1=CC(c(cc2CC3)cc(NCc4ccccc4)c2NC3=O)=CN(C)C1=O FZTVMAGQAZHPHW-UHFFFAOYSA-N 0.000 description 1
- YFUQWOSXYXXZCP-UHFFFAOYSA-N CC1=CC(c(cc2CC3)cc(OCC4CCC4)c2NC3=O)=CN(C)C1=O Chemical compound CC1=CC(c(cc2CC3)cc(OCC4CCC4)c2NC3=O)=CN(C)C1=O YFUQWOSXYXXZCP-UHFFFAOYSA-N 0.000 description 1
- SPOKSLTUXXDBOQ-UHFFFAOYSA-N CC1=CC(c(cc2CC3)cc(OCC4CCCC4)c2NC3=O)=CN(C)C1=O Chemical compound CC1=CC(c(cc2CC3)cc(OCC4CCCC4)c2NC3=O)=CN(C)C1=O SPOKSLTUXXDBOQ-UHFFFAOYSA-N 0.000 description 1
- BWGLABGGUZAIPX-UHFFFAOYSA-N CC1=CC(c(cc2CC3)cc(OCc4ccccc4)c2NC3=O)=CN(C)C1=O Chemical compound CC1=CC(c(cc2CC3)cc(OCc4ccccc4)c2NC3=O)=CN(C)C1=O BWGLABGGUZAIPX-UHFFFAOYSA-N 0.000 description 1
- VPHUWFLMVWRQRC-UHFFFAOYSA-N CC1=CC(c(cc2CC3)cc(OCc4ncc[s]4)c2NC3O)=CN(C)C1=O Chemical compound CC1=CC(c(cc2CC3)cc(OCc4ncc[s]4)c2NC3O)=CN(C)C1=O VPHUWFLMVWRQRC-UHFFFAOYSA-N 0.000 description 1
- GEDDCXNAIGAERT-UHFFFAOYSA-N CCC(NC(CC1)=O)=C1C=C Chemical compound CCC(NC(CC1)=O)=C1C=C GEDDCXNAIGAERT-UHFFFAOYSA-N 0.000 description 1
- FHBNFRRVWIGCTP-UHFFFAOYSA-N CCNc(cc1)cc(Cl)c1Br Chemical compound CCNc(cc1)cc(Cl)c1Br FHBNFRRVWIGCTP-UHFFFAOYSA-N 0.000 description 1
- PDYBQCXGXHBLTM-RLZPDRNQSA-N C[C@@H](CCCC(N1)=O)/C1=C(\C=C(/C)\Br)/O Chemical compound C[C@@H](CCCC(N1)=O)/C1=C(\C=C(/C)\Br)/O PDYBQCXGXHBLTM-RLZPDRNQSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N NC1CCCC1 Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- HJSJNYFZMUJXKD-UHFFFAOYSA-N O=C(CC1)NC2C1=CC(Br)=CC2OCc1ccncc1 Chemical compound O=C(CC1)NC2C1=CC(Br)=CC2OCc1ccncc1 HJSJNYFZMUJXKD-UHFFFAOYSA-N 0.000 description 1
- QDXLICLDIAQOSZ-UHFFFAOYSA-N O=C(CC1)Nc(c(OCc2ccccc2)c2)c1cc2Br Chemical compound O=C(CC1)Nc(c(OCc2ccccc2)c2)c1cc2Br QDXLICLDIAQOSZ-UHFFFAOYSA-N 0.000 description 1
- QOPFKGOBJUYBLM-UHFFFAOYSA-N O=C(CCCl)Nc(cc1)cc(Cl)c1Br Chemical compound O=C(CCCl)Nc(cc1)cc(Cl)c1Br QOPFKGOBJUYBLM-UHFFFAOYSA-N 0.000 description 1
- OIUOYGHETRFYPM-UHFFFAOYSA-N O=C(CCCl)Nc(cccc1Cl)c1Br Chemical compound O=C(CCCl)Nc(cccc1Cl)c1Br OIUOYGHETRFYPM-UHFFFAOYSA-N 0.000 description 1
- NNJVUTXGYOGQGU-UHFFFAOYSA-N O=C(CCc1ccc2Cl)Nc1c2Br Chemical compound O=C(CCc1ccc2Cl)Nc1c2Br NNJVUTXGYOGQGU-UHFFFAOYSA-N 0.000 description 1
- HHBVWZBALYIKTK-UHFFFAOYSA-N O=C1Nc2c(COC3=CCCC3)c(Cl)ccc2CC1 Chemical compound O=C1Nc2c(COC3=CCCC3)c(Cl)ccc2CC1 HHBVWZBALYIKTK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- 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
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- C07D401/04—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
- 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562203623P | 2015-08-11 | 2015-08-11 | |
| US62/203,623 | 2015-08-11 | ||
| US201662356579P | 2016-06-30 | 2016-06-30 | |
| US62/356,579 | 2016-06-30 | ||
| PCT/CA2016/050943 WO2017024408A1 (en) | 2015-08-11 | 2016-08-11 | Aryl-substituted dihydroquinolinones, their preparation and their use as pharmaceuticals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108290856A true CN108290856A (zh) | 2018-07-17 |
Family
ID=57982883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680058648.1A Pending CN108290856A (zh) | 2015-08-11 | 2016-08-11 | 芳基-取代的二氢喹诺酮、它们的制备和它们作为药物的用途 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10501438B2 (https=) |
| EP (1) | EP3334717B1 (https=) |
| JP (1) | JP2018527340A (https=) |
| KR (1) | KR20180039117A (https=) |
| CN (1) | CN108290856A (https=) |
| AU (1) | AU2016305513A1 (https=) |
| CA (1) | CA2994472A1 (https=) |
| HK (1) | HK1256753A1 (https=) |
| IL (1) | IL257347A (https=) |
| MX (1) | MX2018001751A (https=) |
| WO (1) | WO2017024408A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112239456A (zh) * | 2020-06-09 | 2021-01-19 | 浙江理工大学 | 一种取代2，3-二氢喹诺酮化合物的制备方法 |
| CN113631535A (zh) * | 2019-03-11 | 2021-11-09 | 协同医药发展有限公司 | 治疗铁死亡相关紊乱的杂芳基和双杂环芳基衍生物 |
| CN114276333A (zh) * | 2020-09-28 | 2022-04-05 | 中国科学院上海药物研究所 | 二氢喹喔啉类溴结构域二价抑制剂 |
| CN118005653A (zh) * | 2023-04-23 | 2024-05-10 | 信义核新(北京)生物科技有限公司 | 喹诺酮类似物及其用途 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020093162A1 (en) * | 2018-11-07 | 2020-05-14 | Neomed Institute | Treatment of bet inhibitor-resistant cancers and other diseases responsive to dual bet and cbp/ep300 inhibition therapy |
Citations (2)
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|---|---|---|---|---|
| CA2895404A1 (en) * | 2012-12-20 | 2014-06-26 | Bayer Pharma Aktiengesellschaft | Bet-protein-inhibiting dihydropyridopyrazinones |
| WO2014096965A2 (en) * | 2012-12-21 | 2014-06-26 | Rvx Therapeutics Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
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| US4550166A (en) | 1984-05-21 | 1985-10-29 | American Cyanamid Company | (Pyridinyl)-1,2,4-triazolo[4,3-a]pyridines |
| US4785005A (en) * | 1986-06-25 | 1988-11-15 | Rorer Pharmaceutical Corporation | 6-(6-alkylpyridone)-carbostyril compounds and their cardiotonic uses |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| DE4237656A1 (de) | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
| US6162804A (en) | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
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- 2016-08-11 JP JP2018506998A patent/JP2018527340A/ja active Pending
- 2016-08-11 MX MX2018001751A patent/MX2018001751A/es unknown
- 2016-08-11 CA CA2994472A patent/CA2994472A1/en not_active Abandoned
- 2016-08-11 EP EP16834368.9A patent/EP3334717B1/en active Active
- 2016-08-11 CN CN201680058648.1A patent/CN108290856A/zh active Pending
- 2016-08-11 HK HK18115833.9A patent/HK1256753A1/zh unknown
- 2016-08-11 KR KR1020187006580A patent/KR20180039117A/ko not_active Withdrawn
- 2016-08-11 AU AU2016305513A patent/AU2016305513A1/en not_active Abandoned
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2018
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2019
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113631535A (zh) * | 2019-03-11 | 2021-11-09 | 协同医药发展有限公司 | 治疗铁死亡相关紊乱的杂芳基和双杂环芳基衍生物 |
| CN113631535B (zh) * | 2019-03-11 | 2024-04-12 | 协同医药发展有限公司 | 治疗铁死亡相关紊乱的杂芳基和双杂环芳基衍生物 |
| CN112239456A (zh) * | 2020-06-09 | 2021-01-19 | 浙江理工大学 | 一种取代2，3-二氢喹诺酮化合物的制备方法 |
| CN112239456B (zh) * | 2020-06-09 | 2021-09-07 | 浙江理工大学 | 一种取代2，3-二氢喹诺酮化合物的制备方法 |
| CN114276333A (zh) * | 2020-09-28 | 2022-04-05 | 中国科学院上海药物研究所 | 二氢喹喔啉类溴结构域二价抑制剂 |
| CN114276333B (zh) * | 2020-09-28 | 2023-05-09 | 中国科学院上海药物研究所 | 二氢喹喔啉类溴结构域二价抑制剂 |
| CN118005653A (zh) * | 2023-04-23 | 2024-05-10 | 信义核新(北京)生物科技有限公司 | 喹诺酮类似物及其用途 |
| CN118005653B (zh) * | 2023-04-23 | 2024-12-10 | 信义核新(北京)生物科技有限公司 | 喹诺酮类似物及其用途 |
Also Published As
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|---|---|
| EP3334717A1 (en) | 2018-06-20 |
| KR20180039117A (ko) | 2018-04-17 |
| CA2994472A1 (en) | 2017-02-16 |
| JP2018527340A (ja) | 2018-09-20 |
| EP3334717B1 (en) | 2020-07-01 |
| US10501438B2 (en) | 2019-12-10 |
| MX2018001751A (es) | 2018-08-01 |
| HK1256753A1 (zh) | 2019-10-04 |
| AU2016305513A1 (en) | 2018-03-08 |
| IL257347A (en) | 2018-03-29 |
| WO2017024408A1 (en) | 2017-02-16 |
| US20200299262A1 (en) | 2020-09-24 |
| US20180230130A1 (en) | 2018-08-16 |
| EP3334717A4 (en) | 2019-02-13 |
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