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1. WO2011098035 - SINOMENINE DERIVATIVES, SYNTHETIC METHODS AND USES THEREOF

Publication Number WO/2011/098035
Publication Date 18.08.2011
International Application No. PCT/CN2011/070893
International Filing Date 09.02.2011
IPC
C07D 221/28 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
221Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/-C07D219/187
02condensed with carbocyclic rings or ring systems
22Bridged ring systems
28Morphinans
A61K 31/485 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
435having six-membered rings with one nitrogen as the only ring hetero atom
47Quinolines; Isoquinolines
485Morphinan derivatives, e.g. morphine, codeine
A61P 29/00 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
29Non-central analgesic, antipyretic or antiinflammatory agents, e.g antirheumatic agents; Non-steroidal antiinflammatory drugs (NSAIDs)
A61P 37/06 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
37Drugs for immunological or allergic disorders
02Immunomodulators
06Immunosuppressants, e.g. drugs for graft rejection
CPC
A61K 31/485
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
435having six-membered rings with one nitrogen as the only ring hetero atom
47Quinolines; Isoquinolines
485Morphinan derivatives, e.g. morphine, codeine
A61P 1/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
1Drugs for disorders of the alimentary tract or the digestive system
A61P 11/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
11Drugs for disorders of the respiratory system
A61P 11/06
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
11Drugs for disorders of the respiratory system
06Antiasthmatics
A61P 17/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
17Drugs for dermatological disorders
A61P 17/06
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
17Drugs for dermatological disorders
06Antipsoriatics
Applicants
  • 中国科学院上海有机化学研究所 SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES [CN]/[CN] (AllExceptUS)
  • 中国科学院上海生命科学研究院 SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES [CN]/[CN] (AllExceptUS)
  • 姚祝军 YAO, Zhujun [CN]/[CN] (UsOnly)
  • 孙兵 SUN, Bing [CN]/[CN] (UsOnly)
  • 楼杨通 LOU, Yangtong [CN]/[CN] (UsOnly)
  • 杨震宇 YANG, Zhenyu [CN]/[CN] (UsOnly)
  • 陈爱中 CHEN, Aizhong [CN]/[CN] (UsOnly)
  • 马钊 MA, Zhao [CN]/[CN] (UsOnly)
Inventors
  • 姚祝军 YAO, Zhujun
  • 孙兵 SUN, Bing
  • 楼杨通 LOU, Yangtong
  • 杨震宇 YANG, Zhenyu
  • 陈爱中 CHEN, Aizhong
  • 马钊 MA, Zhao
Agents
  • 上海专利商标事务所有限公司 SHANGHAI PATENT & TRADEMARK LAW OFFICE, LLC
Priority Data
201010108675.X10.02.2010CN
Publication Language Chinese (zh)
Filing Language Chinese (ZH)
Designated States
Title
(EN) SINOMENINE DERIVATIVES, SYNTHETIC METHODS AND USES THEREOF
(FR) DÉRIVÉS DE SINOMÉNINE, LEURS PROCÉDÉS DE SYNTHÈSE ET LEURS UTILISATIONS
(ZH) 一种青藤碱衍生物、合成方法及其用途
Abstract
(EN) Sinomenine derivatives, synthetic methods and uses thereof are disclosed. The said sinomenine derivatives include oxidized derivatives and C-10 substituted derivatives of sinomenine. Aiming at phenolic hydroxyl group existing in sinomenine which is easy to be oxidized, sinomenine derivatives are synthesized by oxidation, oxidation and de-aromatization, conjugate addition-aromatization to introduce substituent groups on C-10. The sinomenine derivatives have the following structure formule (I). The synthesized compounds are evaluated for their inhibition activity of tumor necrosis factor α (THF-α) in vitro. The results show that most compounds exhibit anti-inflammatory activity. Some compounds exhibit better activity than sinomenine. The said compounds can be used for the treatment of immune diseases such as rheumatoid arthritis (RA).
(FR) L'invention concerne des dérivés de sinoménine, leurs procédés de synthèse et leurs utilisations. Lesdits dérivés de sinoménine comprennent des dérivés oxydés et des dérivés substitués en C-10 de sinoménine. En visant le groupe hydroxyle phénolique existant dans la sinoménine qui est facile à oxyder, des dérivés de sinoménine sont synthétisés par oxydation, oxydation et désaromatisation, addition-aromatisation conjuguées pour introduire des groupes substituants sur C-10. Les dérivés de sinoménine ont la structure suivante : Les composés synthétisés sont évalués pour leur activité d'inhibition du facteur de nécrose tumorale α (THF-α) in vitro. Les résultats montrent que la plupart des composés présentent une activité anti-inflammatoire. Certains composés présentent une meilleure activité que la sinoménine. Lesdits composés peuvent être utilisés pour le traitement de maladies immunitaires telles que l'arthrite rhumatoïde (RA).
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