KR101823451B1 - 퀴논계 화합물, 이의 광학 이성질체 및 이의 제조 방법과 의약 용도 - Google Patents
퀴논계 화합물, 이의 광학 이성질체 및 이의 제조 방법과 의약 용도 Download PDFInfo
- Publication number
- KR101823451B1 KR101823451B1 KR1020167003638A KR20167003638A KR101823451B1 KR 101823451 B1 KR101823451 B1 KR 101823451B1 KR 1020167003638 A KR1020167003638 A KR 1020167003638A KR 20167003638 A KR20167003638 A KR 20167003638A KR 101823451 B1 KR101823451 B1 KR 101823451B1
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- group
- acid
- octane
- ethoxy
- 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.)
- Active
Links
- 0 C**C(*)(O)OC1C(CC2)CCN2C1 Chemical compound C**C(*)(O)OC1C(CC2)CCN2C1 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- UOKZUTXLHRTLFH-UHFFFAOYSA-N NOc1ccccc1 Chemical compound NOc1ccccc1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 description 2
- IVLICPVPXWEGCA-UHFFFAOYSA-N OC1C(CC2)CCN2C1 Chemical compound OC1C(CC2)CCN2C1 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 2
- IVLICPVPXWEGCA-SSDOTTSWSA-N O[C@H]1C(CC2)CCN2C1 Chemical compound O[C@H]1C(CC2)CCN2C1 IVLICPVPXWEGCA-SSDOTTSWSA-N 0.000 description 2
- SGWALAKNEKTNQH-MSOLQXFVSA-N O[C@](CO[C@H]1C(CC2)CCN2C1)(C1CC1)c1ccccc1 Chemical compound O[C@](CO[C@H]1C(CC2)CCN2C1)(C1CC1)c1ccccc1 SGWALAKNEKTNQH-MSOLQXFVSA-N 0.000 description 2
- FGWQWHYLUYJECU-UHFFFAOYSA-N C1OC1(C1CCC1)c1ccccc1 Chemical compound C1OC1(C1CCC1)c1ccccc1 FGWQWHYLUYJECU-UHFFFAOYSA-N 0.000 description 1
- RABSINIGENQCNF-UHFFFAOYSA-N C=[I]1(CCC2CC1)CC2O Chemical compound C=[I]1(CCC2CC1)CC2O RABSINIGENQCNF-UHFFFAOYSA-N 0.000 description 1
- MWBULQNPGVGHKO-UHFFFAOYSA-N CC1C(CC2)CCN2C1 Chemical compound CC1C(CC2)CCN2C1 MWBULQNPGVGHKO-UHFFFAOYSA-N 0.000 description 1
- DDAHODSRFCRULG-UHFFFAOYSA-N COCOc1ccccc1 Chemical compound COCOc1ccccc1 DDAHODSRFCRULG-UHFFFAOYSA-N 0.000 description 1
- IVXFVCSBZYNGCO-FOIFJWKZSA-N C[N]1(CCC2CC1)C[C@@]2(N=C)OCC(C1CCCC1)c1ccccc1 Chemical compound C[N]1(CCC2CC1)C[C@@]2(N=C)OCC(C1CCCC1)c1ccccc1 IVXFVCSBZYNGCO-FOIFJWKZSA-N 0.000 description 1
- OVKQBCMUOQDIFM-UHFFFAOYSA-N ClCOCOc1ccccc1 Chemical compound ClCOCOc1ccccc1 OVKQBCMUOQDIFM-UHFFFAOYSA-N 0.000 description 1
- GFSGCECAFRTXDG-ROUUACIJSA-N O[C@](CO[C@@H]1C(CC2)CCN2C1)(C1CC1)C1=CC=CCC1 Chemical compound O[C@](CO[C@@H]1C(CC2)CCN2C1)(C1CC1)C1=CC=CCC1 GFSGCECAFRTXDG-ROUUACIJSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61K31/49—Cinchonan derivatives, e.g. quinine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4808—Preparations in capsules, e.g. of gelatin, of chocolate characterised by the form of the capsule or the structure of the filling; Capsules containing small tablets; Capsules with outer layer for immediate drug release
-
- 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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310297901 | 2013-07-13 | ||
| CN201310297901.7 | 2013-07-13 | ||
| PCT/CN2014/000669 WO2015007073A1 (zh) | 2013-07-13 | 2014-07-11 | 奎宁类化合物、其光学异构体及其制备方法和医药用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160033146A KR20160033146A (ko) | 2016-03-25 |
| KR101823451B1 true KR101823451B1 (ko) | 2018-01-30 |
Family
ID=52345746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167003638A Active KR101823451B1 (ko) | 2013-07-13 | 2014-07-11 | 퀴논계 화합물, 이의 광학 이성질체 및 이의 제조 방법과 의약 용도 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9751875B2 (https=) |
| EP (1) | EP3023424B1 (https=) |
| JP (1) | JP6218940B2 (https=) |
| KR (1) | KR101823451B1 (https=) |
| CN (1) | CN105431432B (https=) |
| AU (1) | AU2014292722B2 (https=) |
| BR (1) | BR112016000629B1 (https=) |
| CA (1) | CA2921621C (https=) |
| ES (1) | ES2726664T3 (https=) |
| RU (1) | RU2641285C2 (https=) |
| TR (1) | TR201906532T4 (https=) |
| WO (1) | WO2015007073A1 (https=) |
| ZA (1) | ZA201600997B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6693943B2 (ja) * | 2015-03-02 | 2020-05-13 | 株式会社Lttバイオファーマ | キヌクリジン誘導体 |
| CA3047023C (en) | 2016-12-14 | 2022-05-31 | Beijing Showby Pharmaceutical Co., Ltd. | Class of bifunctional compounds with quaternary ammonium salt structure |
| CN109824661B (zh) * | 2019-03-30 | 2020-06-05 | 山东博洛德生物科技有限公司 | 一种盐酸戊乙奎醚中杂质的制备方法 |
| CN109824662A (zh) * | 2019-03-30 | 2019-05-31 | 山东博洛德生物科技有限公司 | 一种奎宁类化合物及其制备方法 |
| CN109776521A (zh) * | 2019-03-30 | 2019-05-21 | 山东博洛德生物科技有限公司 | 一种含有季铵基团的奎宁类化合物及其制备方法 |
| CA3181333A1 (en) * | 2020-04-26 | 2021-11-04 | Beijing Showby Pharmaceutical Co., Ltd. | Crystals, preparation method and application of a muscarinic receptor antagonist |
| CN114306331B (zh) * | 2020-10-10 | 2023-07-18 | 远大生命科学(武汉)有限公司 | 戊乙奎醚在治疗或预防视力损伤性眼部疾病中的用途 |
| CN118555954B (zh) * | 2022-01-19 | 2025-11-04 | 北京硕佰医药科技有限责任公司 | 一种治疗鼻炎的溶液型鼻喷雾剂及制备方法 |
| CN116514800A (zh) * | 2023-05-06 | 2023-08-01 | 湖南一格制药有限公司 | 盐酸戊乙奎醚的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070631A (zh) * | 2009-11-20 | 2011-05-25 | 中国人民解放军军事医学科学院毒物药物研究所 | 戊乙奎醚光学异构体的季铵盐、药物组合物及其医药用途 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1219606A (en) | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| DE4108393A1 (de) | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln |
| NO2005012I1 (no) * | 1994-12-28 | 2005-06-06 | Debio Rech Pharma Sa | Triptorelin og farmasoytisk akseptable salter derav |
| ES2165768B1 (es) * | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| CZ294251B6 (cs) * | 2000-06-27 | 2004-11-10 | Laboratorios S. A. L. V. A. T., S. A. | Karbamáty a jejich použití pro výrobu farmaceutického prostředku |
| IL156558A0 (en) * | 2000-12-28 | 2004-01-04 | Almirall Prodesfarma Ag | Novel quinuclidine derivatives and medicinal compositions containing the same |
| ES2203327B1 (es) * | 2002-06-21 | 2005-06-16 | Almirall Prodesfarma, S.A. | Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen. |
| ES2204295B1 (es) * | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| PE20060259A1 (es) | 2004-04-27 | 2006-03-25 | Glaxo Group Ltd | Compuestos de quinuclidina como antagonistas del receptor de acetilcolina muscarinico |
| JP4637715B2 (ja) * | 2005-10-17 | 2011-02-23 | 日信工業株式会社 | 車両用支持構造体の製造方法 |
| CN1951938A (zh) * | 2005-10-21 | 2007-04-25 | 刘丽娅 | 戊乙奎醚季铵盐及其衍生物 |
| AU2007336054A1 (en) * | 2006-12-19 | 2008-06-26 | Astrazeneca Ab | Quinuclidinol derivatives as muscarinic receptor antagonists |
| KR20090107567A (ko) * | 2007-02-09 | 2009-10-13 | 아스텔라스세이야쿠 가부시키가이샤 | 아자 가교환 화합물 |
| CN102850344A (zh) * | 2011-06-28 | 2013-01-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 戊乙奎醚光学异构体衍生物用于抗肿瘤的医药用途 |
-
2014
- 2014-07-11 EP EP14825941.9A patent/EP3023424B1/en active Active
- 2014-07-11 RU RU2016104437A patent/RU2641285C2/ru active
- 2014-07-11 US US14/904,766 patent/US9751875B2/en active Active
- 2014-07-11 CN CN201480020342.8A patent/CN105431432B/zh active Active
- 2014-07-11 AU AU2014292722A patent/AU2014292722B2/en active Active
- 2014-07-11 TR TR2019/06532T patent/TR201906532T4/tr unknown
- 2014-07-11 ES ES14825941T patent/ES2726664T3/es active Active
- 2014-07-11 CA CA2921621A patent/CA2921621C/en active Active
- 2014-07-11 JP JP2016524657A patent/JP6218940B2/ja active Active
- 2014-07-11 KR KR1020167003638A patent/KR101823451B1/ko active Active
- 2014-07-11 BR BR112016000629-1A patent/BR112016000629B1/pt active IP Right Grant
- 2014-07-11 WO PCT/CN2014/000669 patent/WO2015007073A1/zh not_active Ceased
-
2016
- 2016-02-12 ZA ZA2016/00997A patent/ZA201600997B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070631A (zh) * | 2009-11-20 | 2011-05-25 | 中国人民解放军军事医学科学院毒物药物研究所 | 戊乙奎醚光学异构体的季铵盐、药物组合物及其医药用途 |
Non-Patent Citations (1)
| Title |
|---|
| J. Med. Chem., 2009, 52, 2493-2505. |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112016000629B1 (pt) | 2023-10-31 |
| CA2921621A1 (en) | 2015-01-22 |
| CA2921621C (en) | 2018-08-28 |
| EP3023424A4 (en) | 2017-01-18 |
| CN105431432B (zh) | 2018-01-09 |
| EP3023424A1 (en) | 2016-05-25 |
| ES2726664T3 (es) | 2019-10-08 |
| US9751875B2 (en) | 2017-09-05 |
| KR20160033146A (ko) | 2016-03-25 |
| CN105431432A (zh) | 2016-03-23 |
| WO2015007073A1 (zh) | 2015-01-22 |
| EP3023424B1 (en) | 2019-02-27 |
| BR112016000629A2 (https=) | 2017-07-25 |
| RU2641285C2 (ru) | 2018-01-17 |
| TR201906532T4 (tr) | 2019-05-21 |
| ZA201600997B (en) | 2018-05-30 |
| RU2016104437A (ru) | 2017-08-16 |
| JP6218940B2 (ja) | 2017-10-25 |
| US20160244439A1 (en) | 2016-08-25 |
| AU2014292722A1 (en) | 2016-03-03 |
| AU2014292722B2 (en) | 2017-03-09 |
| JP2016528199A (ja) | 2016-09-15 |
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