HK1204942A1 - Pharmaceutical composition comprising (1r,4r)-6-fluoro-n,n-dimethyl- 4-phenyl-4,9-dihydro-3h-spiro[cyclohexane-1,1-pyrano- [3,4,b]indol]-4-amine and a propionic acid derivative (1r4r)-6--nn--4--49--3h-[- 11-[34b]]-4- - Google Patents

Pharmaceutical composition comprising (1r,4r)-6-fluoro-n,n-dimethyl- 4-phenyl-4,9-dihydro-3h-spiro[cyclohexane-1,1-pyrano- [3,4,b]indol]-4-amine and a propionic acid derivative (1r4r)-6--nn--4--49--3h-[- 11-[34b]]-4-

Info

Publication number
HK1204942A1
HK1204942A1 HK15105573.7A HK15105573A HK1204942A1 HK 1204942 A1 HK1204942 A1 HK 1204942A1 HK 15105573 A HK15105573 A HK 15105573A HK 1204942 A1 HK1204942 A1 HK 1204942A1
Authority
HK
Hong Kong
Prior art keywords
pyrano
indol
spiro
dihydro
cyclohexane
Prior art date
Application number
HK15105573.7A
Other languages
English (en)
Chinese (zh)
Inventor
Stefanie Frosch
Klaus Linz
Klaus Schiene
Original Assignee
Gruenenthal Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh
Publication of HK1204942A1 publication Critical patent/HK1204942A1/xx

Links

Classifications

    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
HK15105573.7A 2012-05-18 2015-06-11 Pharmaceutical composition comprising (1r,4r)-6-fluoro-n,n-dimethyl- 4-phenyl-4,9-dihydro-3h-spiro[cyclohexane-1,1-pyrano- [3,4,b]indol]-4-amine and a propionic acid derivative (1r4r)-6--nn--4--49--3h-[- 11-[34b]]-4- HK1204942A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12003935 2012-05-18
PCT/EP2013/001466 WO2013170967A1 (en) 2012-05-18 2013-05-16 Pharmaceutical composition comprising (1r,4r)-6'-fluoro-n,n-dimethyl-4-phenyl-4',9'-dihydro-3'h-spiro[cyclohexane-1,1'-pyrano-[3,4,b]indol]-4-amine and a propionic acid derivative

Publications (1)

Publication Number Publication Date
HK1204942A1 true HK1204942A1 (en) 2015-12-11

Family

ID=48468206

Family Applications (1)

Application Number Title Priority Date Filing Date
HK15105573.7A HK1204942A1 (en) 2012-05-18 2015-06-11 Pharmaceutical composition comprising (1r,4r)-6-fluoro-n,n-dimethyl- 4-phenyl-4,9-dihydro-3h-spiro[cyclohexane-1,1-pyrano- [3,4,b]indol]-4-amine and a propionic acid derivative (1r4r)-6--nn--4--49--3h-[- 11-[34b]]-4-

Country Status (23)

Country Link
US (2) US9320729B2 (sr)
EP (1) EP2849745B1 (sr)
JP (1) JP6116674B2 (sr)
CN (1) CN104284659A (sr)
AU (1) AU2013262073B2 (sr)
BR (1) BR112014028571A2 (sr)
CA (1) CA2873656A1 (sr)
CY (1) CY1119786T1 (sr)
DK (1) DK2849745T3 (sr)
EA (1) EA028200B1 (sr)
ES (1) ES2658216T3 (sr)
HK (1) HK1204942A1 (sr)
HR (1) HRP20171693T1 (sr)
HU (1) HUE035112T2 (sr)
IL (1) IL235655B (sr)
LT (1) LT2849745T (sr)
MX (1) MX354687B (sr)
NO (1) NO2849745T3 (sr)
PL (1) PL2849745T3 (sr)
PT (1) PT2849745T (sr)
RS (1) RS56771B1 (sr)
SI (1) SI2849745T1 (sr)
WO (1) WO2013170967A1 (sr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9855286B2 (en) 2012-05-18 2018-01-02 Gruenenthal Gmbh Pharmaceutical composition comprising (1r,4r)-6′-fluoro-N,N-di methyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine and a salicylic acid component
US9320729B2 (en) 2012-05-18 2016-04-26 Gruenenthal Gmbh Pharmaceutical composition comprising (1r,4r)-6′-flouro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine and a propionic acid derivative
US20130310385A1 (en) 2012-05-18 2013-11-21 Gruenenthal Gmbh Pharmaceutical Composition Comprising (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine and Antidepressants
US20130310435A1 (en) 2012-05-18 2013-11-21 Gruenenthal Gmbh Pharmaceutical Composition Comprising (1r,4r)-6'-fluoro-N, N-dimethyl-4-phenyl-4,9' -dihydro-3'H-spiro[cyclohexane-1,1' -pyrano[3,4,b]indol]-4-amine and Paracetamol or Propacetamol
JP6673924B2 (ja) 2015-01-23 2020-03-25 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 肝機能障害および／または腎機能障害を有する対象における疼痛を治療するためのセブラノパドール

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB971700A (en) 1961-02-02 1964-09-30 Boots Pure Drug Co Ltd Anti-Inflammatory Agents
DE3273329D1 (en) 1981-06-26 1986-10-23 Upjohn Co Analgesic process and composition
US4389393A (en) 1982-03-26 1983-06-21 Forest Laboratories, Inc. Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose
US4404208A (en) 1982-06-30 1983-09-13 E. I. Du Pont De Nemours And Company Analgesic mixture of nalbuphine and tiflamizole
IE55189B1 (en) * 1982-07-08 1990-06-20 Wyeth John & Brother Ltd Pharmaceutical compositions
US4765989A (en) 1983-05-11 1988-08-23 Alza Corporation Osmotic device for administering certain drugs
US4783337A (en) 1983-05-11 1988-11-08 Alza Corporation Osmotic system comprising plurality of members for dispensing drug
US4612008A (en) 1983-05-11 1986-09-16 Alza Corporation Osmotic device with dual thermodynamic activity
EP0189788B1 (de) 1985-01-23 1989-09-13 ASTA Pharma Aktiengesellschaft Synergistische Kombination von Flupirtin und nicht-steroidalen Antiphlogistika
EP0473655B1 (en) 1989-05-22 1997-01-15 Biochemical Veterinary Research Pty. Ltd. Divalent metal salts of indomethacin
EP0661050A1 (en) 1991-07-04 1995-07-05 Taisho Pharmaceutical Co. Ltd Analgesic
JPH05221857A (ja) 1992-02-14 1993-08-31 Arakusu:Kk 配合解熱鎮痛剤
US5472711A (en) 1992-07-30 1995-12-05 Edward Mendell Co., Inc. Agglomerated hydrophilic complexes with multi-phasic release characteristics
US5330761A (en) 1993-01-29 1994-07-19 Edward Mendell Co. Inc. Bioadhesive tablet for non-systemic use products
EP0702681A1 (en) 1993-06-07 1996-03-27 Merck & Co. Inc. Spiro-substituted azacycles as neurokinin antagonists
US5455046A (en) 1993-09-09 1995-10-03 Edward Mendell Co., Inc. Sustained release heterodisperse hydrogel systems for insoluble drugs
US5399362A (en) 1994-04-25 1995-03-21 Edward Mendell Co., Inc. Once-a-day metoprolol oral dosage form
US5914129A (en) 1996-07-23 1999-06-22 Mauskop; Alexander Analgesic composition for treatment of migraine headaches
RS49982B (sr) 1997-09-17 2008-09-29 Euro-Celtique S.A., Sinergistička analgetička kombinacija analgetičkog opijata i inhibitora ciklooksigenaze-2
ATE232382T1 (de) 1998-09-10 2003-02-15 Nycomed Danmark As Pharmazeutische zusammensetzungen mit schneller freisetzung von wirkstoffen
ES2194536T3 (es) * 1998-11-13 2003-11-16 Lilly Co Eli Combinacion de duloxetina con farmacos antiinflamatorios no esteroideos.
DE50104197D1 (de) 2000-12-28 2004-11-25 Fresenius Kabi Austria Gmbh Gr Stabile Infusionslösung von Diclofenac-Salzen, deren Herstellung und Verwendung
WO2003064425A1 (en) 2002-01-28 2003-08-07 Pfizer Japan Inc. N-substituted spiropiperidine compounds as ligands for orl-1 receptor
SI1374906T1 (sl) 2002-06-17 2007-10-31 Chiesi Farma Spa Postopek za pripravo inkluzijskih spojin piroksakama: beta-ciklodekstrina
DE10252667A1 (de) 2002-11-11 2004-05-27 Grünenthal GmbH Spirocyclische Cyclohexan-Derivate
DE10257824B4 (de) 2002-12-10 2004-11-11 Kochem, Hans-Günter, Dr. Zusammensetzung zur Schmerzbehandlung, insbesondere zur Behandlung von Gelenkschmerzen
US20100297252A1 (en) 2003-03-03 2010-11-25 Elan Pharma International Ltd. Nanoparticulate meloxicam formulations
US7132452B2 (en) 2003-03-10 2006-11-07 Fang-Yu Lee Topical formulation having effects on alleviating pain/inflammation caused by herpes virus infection
DE10360792A1 (de) 2003-12-23 2005-07-28 Grünenthal GmbH Spirocyclische Cyclohexan-Derivate
WO2006134486A2 (en) 2005-06-17 2006-12-21 Pfizer Japan Inc. Alpha-(aryl-or heteroaryl-methyl)-beta piperidino propanamide compounds as orl1-receptor antagonists
ES2358763T3 (es) 2006-04-28 2011-05-13 Grünenthal GmbH Combinación farmacéutica que comprende 3-(3-dimetilamino-1-etil-2-metilpropil)fenol y un nsaid.
CA2650423C (en) 2006-04-28 2014-08-12 Gruenenthal Gmbh Pharmaceutical combination comprising 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol and paracetamol
CN101147735A (zh) 2006-09-19 2008-03-26 沈阳华泰药物研究有限公司 注射用药物组合物及其药盒
DE102006046745A1 (de) 2006-09-29 2008-04-03 Grünenthal GmbH Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz
DE102006056458A1 (de) 2006-11-28 2008-05-29 Grünenthal GmbH Arzneimittelzubereitung von Tramadol und Acetaminophen
CA2701838A1 (en) 2007-10-09 2009-04-16 Merck Patent Gmbh Pharmaceutical compositions containing benfotiamine and one or more pharmaceutically active agents for the treatment of pain conditions of neuropathic origin
CN100560061C (zh) 2008-06-20 2009-11-18 海南锦瑞制药股份有限公司 一种氯诺昔康冻干粉针剂及其制备方法
EP2331210B1 (en) 2008-09-05 2014-07-09 Grünenthal GmbH Pharmaceutical combination of 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol and an antiepileptic
EP2331102A1 (en) 2008-09-05 2011-06-15 Grünenthal GmbH Pharmaceutical combination comprising 6-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol and an nsaid
US20100069501A1 (en) 2008-09-05 2010-03-18 Gruenenthal Gmbh Pharmaceutical Composition Comprising 6-Dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol and Paracetamol
CN103153282B (zh) * 2010-08-04 2015-08-19 格吕伦塔尔有限公司 含6’-氟-(n-甲基-或n,n-二甲基-)-4-苯基-4’,9’-二氢-3’h-螺[环己烷-1,1’-吡喃并[3,4,b]吲哚]-4-胺的药物剂型
CA2805523C (en) * 2010-08-04 2018-06-12 Gruenenthal Gmbh Pharmaceutical dosage form comprising 6'-fluoro-(n-methyl- or n,n-dimethyl-)-4-phenyl-4',9'-dihydro-3'h-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine for the treatment of nociceptive pain
AU2011287952B2 (en) * 2010-08-04 2014-08-21 Grünenthal GmbH Pharmaceutical dosage form comprising 6'-fluoro-(N-methyl- or N,N-dimethyl-)-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane- 1,1'-pyrano[3,4,b]indol]-4-amine
US9320729B2 (en) 2012-05-18 2016-04-26 Gruenenthal Gmbh Pharmaceutical composition comprising (1r,4r)-6′-flouro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine and a propionic acid derivative

Also Published As

Publication number Publication date
HUE035112T2 (en) 2018-05-02
EP2849745B1 (en) 2017-11-01
CN104284659A (zh) 2015-01-14
CY1119786T1 (el) 2018-06-27
NO2849745T3 (sr) 2018-03-31
RS56771B1 (sr) 2018-04-30
US20130324581A1 (en) 2013-12-05
BR112014028571A2 (pt) 2017-06-27
US10076510B2 (en) 2018-09-18
LT2849745T (lt) 2018-01-25
PT2849745T (pt) 2018-02-07
EP2849745A1 (en) 2015-03-25
JP2015516447A (ja) 2015-06-11
SI2849745T1 (en) 2018-03-30
MX2014013148A (es) 2015-01-19
CA2873656A1 (en) 2013-11-21
US20160199349A1 (en) 2016-07-14
WO2013170967A1 (en) 2013-11-21
AU2013262073B2 (en) 2018-01-18
DK2849745T3 (en) 2017-12-04
US9320729B2 (en) 2016-04-26
IL235655A0 (en) 2015-01-29
EA201401266A1 (ru) 2016-05-31
IL235655B (en) 2018-08-30
AU2013262073A1 (en) 2015-01-22
PL2849745T3 (pl) 2018-04-30
JP6116674B2 (ja) 2017-04-19
MX354687B (es) 2018-03-15
EA028200B1 (ru) 2017-10-31
HRP20171693T1 (hr) 2017-12-15
ES2658216T3 (es) 2018-03-08

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Free format text: CORRECTED DATA OF SECTION 20 TO JOURNAL OF 20151211: (54) PHARMACEUTICAL COMPOSITION COMPRISING (1R,4R)-6'- FLUORO-N,N-DIMETHYL- 4-PHENYL-4',9'-DIHYDRO-3'H-SPIRO(CYCLOHEXANE-1,1'- PYRANO-: (3,4,B)INDOL)-4-AMINE AND A PROPIONIC ACID DERIVATIVE

PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)

Effective date: 20220513