WO2001032169A1 - Agonists specific for the peripheral cannabinoid receptor - Google Patents

Agonists specific for the peripheral cannabinoid receptor Download PDF

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Publication number
WO2001032169A1
WO2001032169A1 PCT/US2000/029903 US0029903W WO0132169A1 WO 2001032169 A1 WO2001032169 A1 WO 2001032169A1 US 0029903 W US0029903 W US 0029903W WO 0132169 A1 WO0132169 A1 WO 0132169A1
Authority
WO
WIPO (PCT)
Prior art keywords
straight
branched chain
chain alkyl
hydrogen
moiety
Prior art date
Application number
PCT/US2000/029903
Other languages
English (en)
French (fr)
Inventor
Ester Fride
Aviva Breuer
Lumir Hanus
Susanna Tchilibon
Michal Horowitz
Raphael Mechoulam
Aaron Garzon
Original Assignee
Yissum Research Development Company Of The Hebrew University
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
Priority to AT00974023T priority Critical patent/ATE286389T1/de
Priority to NZ518054A priority patent/NZ518054A/en
Priority to DE60017287T priority patent/DE60017287T2/de
Priority to AU12458/01A priority patent/AU778149B2/en
Priority to IL14879600A priority patent/IL148796A0/xx
Priority to EP00974023A priority patent/EP1244440B1/en
Priority to KR1020027005566A priority patent/KR100770695B1/ko
Priority to CA002385928A priority patent/CA2385928A1/en
Application filed by Yissum Research Development Company Of The Hebrew University filed Critical Yissum Research Development Company Of The Hebrew University
Priority to HU0203681A priority patent/HUP0203681A3/hu
Priority to JP2001534374A priority patent/JP4231906B2/ja
Publication of WO2001032169A1 publication Critical patent/WO2001032169A1/en
Priority to IL148796A priority patent/IL148796A/en
Priority to US10/133,153 priority patent/US6903137B2/en
Priority to US11/043,089 priority patent/US7214716B2/en

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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • CB1 central nervous system
  • CB2 present outside the CNS, in peripheral organs including peripheral nerve terminals
  • Anandamide attenuates the early phase or the late phase of pain behavior produced by formalin-induced chemical damage. This effect is produced by interaction with CB1 (or CBl-like) receptors, located on peripheral endings of sensory neurons involved in pain transmission. Palmitylethanolamide, which like anandamide is present in the skin, also exhibits peripheral antinociceptive activity during the late phase of pain behavior. Palmitylethanolamide, however does not bind to either CB 1 or CB2. Its analgetic activity is blocked by the specific CB2 antagonist SR 144528, though not by the specific CB1 antagonist SR 141716A. Hence a CB2-like receptor was postulated.
  • the active ingredient of the pharmaceutical compositions according to the present invention is a compound of the general Formula 1 : Figure I
  • Fig. 6b is a bar graph depicting the effects of the CBl receptor antagonist (SR141716A, 5 mg/kg) and the CB2 receptor antagonists (SR144528, 1 mg/kg) on the anti- inflammatory effect of HU-308 on arachidonic acid (A'A) induced swelling of the ear in female Sabra mice treated with 4.5 mg A'A (in 5 ml EtOH) dispersed on the inner surface of one of the ears as measured by the difference between the A'A treated ear and the EtOH treated ear;
  • A'A arachidonic acid
  • Fig. 7 is a bar graph depicting the effect of HU-308 and HU-308 plus SR144528 on formalin-induced peripheral pain in mice 30 minutes after injecting formalin into the hindpaw as measured by the total number of licks of the injected hindpaw recorded for the duration of one hour;
  • Fig. 8 is a graph of disease activity index score vs. treatment day, for mice with acid induced inflammatory bowel disease treated with 10 or 20 mg/kg of HU-308 or vehicle; and
  • Example 1 Synthesis of (+)-(_. - ⁇ -H. 4- ⁇ -H. 5-ce-HV4-r2.6-dihvdroxy-4-(l.l- dimethylheptv ⁇ phenyl]-6.6-dimethylbicvclo[3.1.1]hept-2-ene-2-carbinolpivalate (IID.
  • the CBl binding assays were performed with synaptosomal membranes prepared from rat brains [Devane, W.A., Hanus, L., Breuer, A., Pertwee, R.G., Stevenson, L.A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., & Mechoulam, R. (1992) Science 258, 1946-1949].
  • the four assays were (1) motor activity (ambulation and rearing) in an open field (20 x 30 cm, divided into 12 squares of equal size) for 8 min; (2) immobility ("catalepsy") on a ring of 5.5 cm diameter for 4 min; (3) body temperature with a telethermometer (Yellow Springs Instruments Co.); and (4) analgesia on a hot plate maintained at 55°C, measured as the latency (in seconds) until the first hind paw lick or jump from the plate (the latter response was rarely observed) with a maximum of 45 s.
  • motor activity ambulation and rearing
  • immobility on a ring of 5.5 cm diameter for 4 min
  • body temperature with a telethermometer Yellow Springs Instruments Co.
  • analgesia on a hot plate maintained at 55°C, measured as the latency (in seconds) until the first hind paw lick or jump from the plate (the latter response was rarely observed) with a maximum of 45 s.
  • the results of this study are provided in
  • mice 100 mg/kg and immediately after injection separating the mice into individual cages and recording the number of fecal pellets every 15 min for 2 hours. Rectal temperature was also recorded as a measure of central activity.
  • the results of this study are provided in Fig. 4 in graphical form.
  • Ear inflammation was measured by assessing ear tissue swelling after topical application of arachidonic acid.
  • Nonsteroidal anti-inflammatory drugs have been shown to reduce swelling in this model [Young, J.M., Spires, D.A., Bedord, C. J., Wagner, B., Ballaron, S. & De Young, L.M. (1984) J. Invest. Dermatol. 82, 367-371].
  • arachidonic acid was applied to the inner surface of one ear (4.5 mg in 5 ml ethanol).
  • the opposite ear served as a control (5 ml ethanol).
  • Ear thickness was determined (in 0.01 mm units) every 15 min for 90 min starting immediately after arachidonic acid application using a dial thickness gauge (Mitutoyo, Japan). The results of this study are provided in Fig. 6 in graphical form.
  • Pain mediated by the peripheral nervous system was tested in the "formalin test" for cutaneous (peripheral) pain [Tjolson, A., Berge, O-G., Hunskaar, S., Rosland, J.H. andHole, K. (1992) Pain, 51, 5-17; Calignano, A., LaRana, G., Giuffrida, A. & Piomelli, D. (1998) Nature (London) 394, 277-280; and Jagger, S.I., Hasnie, F.S., Sellaturay, S. and Rice, A.S.C.(1998) Pain 76, 189-199].
  • HU-308 or vehicle was injected i.p.
PCT/US2000/029903 1991-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor WO2001032169A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
KR1020027005566A KR100770695B1 (ko) 1999-10-31 2000-10-30 말초 카나비노이드 수용체 특이적 아고니스트
DE60017287T DE60017287T2 (de) 1999-10-31 2000-10-30 Spezifische Agonisten für periphere Cannabinoid-Rezeptoren
AU12458/01A AU778149B2 (en) 1999-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor
IL14879600A IL148796A0 (en) 1991-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor
EP00974023A EP1244440B1 (en) 1999-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor
AT00974023T ATE286389T1 (de) 1999-10-31 2000-10-30 Spezifische anonisten für peripherische cannabinoid-rezeptoren
CA002385928A CA2385928A1 (en) 1999-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor
NZ518054A NZ518054A (en) 1999-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor
HU0203681A HUP0203681A3 (en) 1999-10-31 2000-10-30 Pharmaceutical compositions containing agonists specific for the peripheral cannabinoid receptor and their use
JP2001534374A JP4231906B2 (ja) 1999-10-31 2000-10-30 末梢カンナビノイド受容体に特異的なアゴニスト
IL148796A IL148796A (en) 1999-10-31 2002-03-20 Use of cannabinoid-specific agonist-specific agonists for the preparation of drugs against autoimmune diseases and cancers
US10/133,153 US6903137B2 (en) 1999-10-31 2002-04-26 Agonists specific for the peripheral cannabinoid receptor
US11/043,089 US7214716B2 (en) 1999-10-31 2005-01-27 Agonists specific for the peripheral cannabinoid receptor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL132661 1999-10-31
IL132661A IL132661A (en) 1999-10-31 1999-10-31 Agonists specific for peripheral cannabinoid receptors

Related Parent Applications (1)

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US09/698,071 Division US6864291B1 (en) 1999-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/133,153 Continuation US6903137B2 (en) 1999-10-31 2002-04-26 Agonists specific for the peripheral cannabinoid receptor

Publications (1)

Publication Number Publication Date
WO2001032169A1 true WO2001032169A1 (en) 2001-05-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/029903 WO2001032169A1 (en) 1991-10-31 2000-10-30 Agonists specific for the peripheral cannabinoid receptor

Country Status (13)

Country Link
US (3) US6864291B1 (US06903137-20050607-C00013.png)
EP (1) EP1244440B1 (US06903137-20050607-C00013.png)
JP (1) JP4231906B2 (US06903137-20050607-C00013.png)
KR (1) KR100770695B1 (US06903137-20050607-C00013.png)
AT (1) ATE286389T1 (US06903137-20050607-C00013.png)
AU (1) AU778149B2 (US06903137-20050607-C00013.png)
CA (1) CA2385928A1 (US06903137-20050607-C00013.png)
DE (1) DE60017287T2 (US06903137-20050607-C00013.png)
HU (1) HUP0203681A3 (US06903137-20050607-C00013.png)
IL (2) IL132661A (US06903137-20050607-C00013.png)
NZ (1) NZ518054A (US06903137-20050607-C00013.png)
WO (1) WO2001032169A1 (US06903137-20050607-C00013.png)
ZA (1) ZA200202181B (US06903137-20050607-C00013.png)

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WO2003043619A1 (en) * 2001-11-23 2003-05-30 Astrazeneca Ab New use for the treatment of gastroesophageal reflux disease
WO2003061699A1 (fr) * 2001-12-27 2003-07-31 Japan Tobacco, Inc. Remedes pour affections allergiques
EP1469842A2 (en) * 2002-01-31 2004-10-27 Pharmos Corporation Bicyclic cb2 cannabinoid receptor ligands
WO2004085385A3 (en) * 2003-03-20 2004-11-25 Schering Corp Cannabinoid receptor ligands
US6900236B1 (en) 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
US6939977B2 (en) 1998-05-04 2005-09-06 The University Of Connecticut Analgesic and immunomodulatory cannabinoids
US6943266B1 (en) 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US6995187B1 (en) 1999-10-18 2006-02-07 University Of Connecticut Peripheral cannabinoid receptor (CB2) selective ligands
US7183313B2 (en) 2002-08-23 2007-02-27 University Of Connecticut Keto cannabinoids with therapeutic indications
WO2007125048A1 (en) * 2006-04-27 2007-11-08 Solvay Pharmaceuticals Gmbh Pharmaceutical compositions comprising cbx cannabinoid receptor modulators and potassium channel modulators
WO2008001369A1 (en) * 2006-06-27 2008-01-03 Pharmos Corporation Use of cb2 receptor agonists for promoting neurogenesis
AU2003209616B2 (en) * 2002-01-31 2008-07-10 Pharmos Corporation Bicyclic CB2 cannabinoid receptor ligands
WO2008107879A1 (en) * 2007-03-05 2008-09-12 Yissum Research Development Company Of The Hebrew University Of Jerusalem Novel cannabidiol derivatives and their use as anti-inflammatory agents
US7763607B2 (en) 2006-04-27 2010-07-27 Solvay Pharmaceuticals Gmbh Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators
WO2011009883A1 (en) 2009-07-23 2011-01-27 INSERM (Institut National de la Santé et de la Recherche Médicale) Selective cb2 receptor agonists for use in the prevention or treatment of alcoholic liver disease
WO2014097188A1 (en) 2012-12-21 2014-06-26 C4T S.C. A.R.L. Compounds of 2,3-dihydro-4h-1,3-benzoxazine-4-one, method for preparing them and pharmaceutical form comprising them
EP2992880A1 (en) * 2014-09-04 2016-03-09 Fundació Institut de Recerca de l'Hospital de la Santa Creu l Sant Pau Use of heme oxygenase 1 inducers and cannabinoid 2 receptor or delta-opioid receptor agonists in inflammatory pain

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US7897598B2 (en) * 1998-06-09 2011-03-01 Alexandros Makriyannis Inhibitors of the anandamide transporter
US7589220B2 (en) * 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter
US7276613B1 (en) 1998-11-24 2007-10-02 University Of Connecticut Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US7161016B1 (en) 1998-11-24 2007-01-09 University Of Connecticut Cannabimimetic lipid amides as useful medications
US8084467B2 (en) * 1999-10-18 2011-12-27 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US7393842B2 (en) * 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
US7119108B1 (en) 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
US7741365B2 (en) * 1999-10-18 2010-06-22 University Of Connecticut Peripheral cannabinoid receptor (CB2) selective ligands
IL132661A (en) * 1999-10-31 2008-11-26 Raphael Mechoulam Agonists specific for peripheral cannabinoid receptors
JP2004532185A (ja) * 2001-01-26 2004-10-21 ユニバーシティ オブ コネチカット 新規なカンナビミメティックリガンド
US7173027B2 (en) * 2001-01-29 2007-02-06 University Of Connecticut Receptor selective cannabimimetic aminoalkylindoles
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CA2464333C (en) 2001-10-26 2011-07-26 University Of Connecticut Heteroindanes: a new class of potent cannabimimetic ligands
US20060172019A1 (en) * 2003-03-07 2006-08-03 Ralston Stuart H Cannabinoid receptor inverse agonists and neutral antagonists as therapeutic agents for the treatment of bone disorders
US7169942B2 (en) * 2003-05-20 2007-01-30 University Of Tennessee Research Foundation Cannabinoid derivatives, methods of making, and use thereof
WO2005123053A2 (en) * 2004-06-22 2005-12-29 Pharmos Limited Use of cb2 receptors agonists for the treatment of huntington’s disease
TWI366460B (en) 2005-06-16 2012-06-21 Euro Celtique Sa Cannabinoid active pharmaceutical ingredient for improved dosage forms
US20070060638A1 (en) * 2005-08-26 2007-03-15 Olmstead Mary C Methods and therapies for potentiating therapeutic activities of a cannabinoid receptor agonist via administration of a cannabinoid receptor antagonist
US9763894B2 (en) * 2006-12-05 2017-09-19 Virginia Commonwealth University Inflammation therapy
GB0702862D0 (en) * 2007-02-14 2007-03-28 Univ Aberdeen Therapeutic compounds
JP2010540618A (ja) * 2007-10-02 2010-12-24 アリエル−ユニバーシティー リサーチ アンド デベロップメント カンパニー リミテッド 幼児の成長および発達を増大するための内在性カンナビノイド
US9193713B2 (en) 2007-10-12 2015-11-24 Abbvie Inc. Compounds as cannabinoid receptor ligands
WO2010041253A1 (en) 2008-10-06 2010-04-15 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Compositions comprising cb receptor agonists, uses thereof and methods for their preparation
EP2986587B1 (en) 2013-04-17 2023-11-22 Sharon Anavi-Goffer Cb2 receptor ligands for the treatment of psychiatric disorders
US9585867B2 (en) 2015-08-06 2017-03-07 Charles Everett Ankner Cannabinod formulation for the sedation of a human or animal
US11612581B2 (en) 2017-08-09 2023-03-28 Cannibite Bvba Cannabis and derivatives thereof for the treatment of pain and inflammation related with dental pulp and bone regeneration related to dental jaw bone defects
WO2021080648A1 (en) * 2019-10-25 2021-04-29 Gelest Technologies, Inc. Silicon-based cannabidiol derivatives and compositions thereof

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IL132661A (en) * 1999-10-31 2008-11-26 Raphael Mechoulam Agonists specific for peripheral cannabinoid receptors

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US6939977B2 (en) 1998-05-04 2005-09-06 The University Of Connecticut Analgesic and immunomodulatory cannabinoids
US6995187B1 (en) 1999-10-18 2006-02-07 University Of Connecticut Peripheral cannabinoid receptor (CB2) selective ligands
US6900236B1 (en) 1999-10-18 2005-05-31 University Of Connecticut Cannabimimetic indole derivatives
US6943266B1 (en) 1999-10-18 2005-09-13 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
WO2003043619A1 (en) * 2001-11-23 2003-05-30 Astrazeneca Ab New use for the treatment of gastroesophageal reflux disease
US7358245B2 (en) 2001-11-23 2008-04-15 Astrazenca Ab Treatment of gastroesophageal reflux disease
WO2003061699A1 (fr) * 2001-12-27 2003-07-31 Japan Tobacco, Inc. Remedes pour affections allergiques
AU2003209616B2 (en) * 2002-01-31 2008-07-10 Pharmos Corporation Bicyclic CB2 cannabinoid receptor ligands
EP1469842A4 (en) * 2002-01-31 2006-04-26 Pharmos Corp BICYCLIC CB2 CANNABINOID RECEPTOR LIGANDS
EP1469842A2 (en) * 2002-01-31 2004-10-27 Pharmos Corporation Bicyclic cb2 cannabinoid receptor ligands
US7183313B2 (en) 2002-08-23 2007-02-27 University Of Connecticut Keto cannabinoids with therapeutic indications
WO2004085385A3 (en) * 2003-03-20 2004-11-25 Schering Corp Cannabinoid receptor ligands
JP2007211017A (ja) * 2003-03-20 2007-08-23 Schering Plough Corp カンナビノイドレセプターリガンド
JP2006520795A (ja) * 2003-03-20 2006-09-14 シェーリング　コーポレイション カンナビノイドレセプターリガンド
US7642272B2 (en) 2003-03-20 2010-01-05 Schering Corporation Cannabinoid receptor ligands
WO2007125048A1 (en) * 2006-04-27 2007-11-08 Solvay Pharmaceuticals Gmbh Pharmaceutical compositions comprising cbx cannabinoid receptor modulators and potassium channel modulators
US7763607B2 (en) 2006-04-27 2010-07-27 Solvay Pharmaceuticals Gmbh Pharmaceutical compositions comprising CBx cannabinoid receptor modulators and potassium channel modulators
WO2008001369A1 (en) * 2006-06-27 2008-01-03 Pharmos Corporation Use of cb2 receptor agonists for promoting neurogenesis
WO2008107879A1 (en) * 2007-03-05 2008-09-12 Yissum Research Development Company Of The Hebrew University Of Jerusalem Novel cannabidiol derivatives and their use as anti-inflammatory agents
WO2011009883A1 (en) 2009-07-23 2011-01-27 INSERM (Institut National de la Santé et de la Recherche Médicale) Selective cb2 receptor agonists for use in the prevention or treatment of alcoholic liver disease
WO2014097188A1 (en) 2012-12-21 2014-06-26 C4T S.C. A.R.L. Compounds of 2,3-dihydro-4h-1,3-benzoxazine-4-one, method for preparing them and pharmaceutical form comprising them
EP2992880A1 (en) * 2014-09-04 2016-03-09 Fundació Institut de Recerca de l'Hospital de la Santa Creu l Sant Pau Use of heme oxygenase 1 inducers and cannabinoid 2 receptor or delta-opioid receptor agonists in inflammatory pain

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JP4231906B2 (ja) 2009-03-04
ZA200202181B (en) 2003-05-28
CA2385928A1 (en) 2001-05-10
DE60017287D1 (de) 2005-02-10
HUP0203681A2 (hu) 2003-04-28
AU1245801A (en) 2001-05-14
HUP0203681A3 (en) 2003-05-28
NZ518054A (en) 2003-10-31
KR100770695B1 (ko) 2007-10-29
US20050165118A1 (en) 2005-07-28
AU778149B2 (en) 2004-11-18
DE60017287T2 (de) 2005-12-08
EP1244440B1 (en) 2005-01-05
US6864291B1 (en) 2005-03-08
US7214716B2 (en) 2007-05-08
EP1244440A4 (en) 2003-05-14
US20020173528A1 (en) 2002-11-21
US6903137B2 (en) 2005-06-07
ATE286389T1 (de) 2005-01-15
IL148796A (en) 2008-11-26
KR20030008208A (ko) 2003-01-24
EP1244440A1 (en) 2002-10-02
IL132661A (en) 2008-11-26
JP2004505006A (ja) 2004-02-19
IL132661A0 (en) 2001-03-19

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