WO2001029007A1 - Pyrazole derivatives as cannabinoid receptor antagonists - Google Patents
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- WO2001029007A1 WO2001029007A1 PCT/US2000/041239 US0041239W WO0129007A1 WO 2001029007 A1 WO2001029007 A1 WO 2001029007A1 US 0041239 W US0041239 W US 0041239W WO 0129007 A1 WO0129007 A1 WO 0129007A1
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A61P9/08—Vasodilators for multiple indications
Definitions
- the present invention relates generally to pyrazole derivatives and is more particularly concerned with new and improved pyrazole derivatives exhibiting high binding affinities for cannabinoid receptors, pharmaceutical preparations employing these analogs and methods of administering therapeutically effective amounts of the preparations to provide a physiological effect.
- Classical cannabinoids such as the marijuana derived cannabinoid ⁇ 9 -tetrahydrocannabinol ( ⁇ 9 -THC), as well as endogenous ligands (anandamide) produce their pharmacological effects via their agonist properties at specific cannabinoid receptors in the body.
- CB1 a central receptor found in the mammalian brain and peripheral tissues
- CB2 a peripheral receptor found only in the peripheral tissues.
- Compounds that are agonists or antagonists for one or both of these receptors have been shown to provide a variety of pharmacological effects.
- Cannabinoid antagonists are compounds that bind to one of the CB1 or CB2 receptors but have no effect. There is considerable interest in developing cannabinoid antagonists possessing high affinity for one of the CB1 or CB2 receptors. Such cannabinoid antagonist materials provide a tool to better understand the mechanisms by which cannabinoid agonists produce their pharmacological effects and for the development of new therapeutic agents.
- cannabimimetic antagonists encompasses pyrazole derivatives.
- Pyrazole analogs have been found to act as antagonists for the CB1 and CB2 receptors, and occasionally to act as agonists for the CB1 and CB2 receptors.
- Most of the known materials show high receptor affinity for only the CB1 cannabinoid receptor. See for instance, Barth, F. et al, Pyrazole Derivatives, Method Of Preparing Them And Pharmaceutical Compositions In Which They Are Present: U.S. Patent No. 5,624,941 to Barth et al, issued April 29, 1 997; Rinaldi-Carmona, M.
- the invention includes several novel pyrazole derivatives and physiologically acceptable salts thereof.
- the invention includes materials selective for either the CB1 or CB2 receptors. Further, some of the analogs have agonistic or antagonistic properties.
- Pyrazole can be represented by the formula:
- R 3 is selected from the group consisting of H and a branched or unbranched chain having the structure (CH 2 ) n CH 3 where n is an integer from 0 to about 3.
- R 4 , R 5 and R 6 are each selected from the group consisting of halogen, N 3 , NCS, OCH 3 , CH 3 , CH 2 CH 3 , N0 2 , NH 2 , phenyl and phenyl with at least one substituent from the group consisting of halogen, N 3 , NCS, OCH 3 , CH 3 , CH 2 CH 3 , NO 2 , and NH 2 .
- R 2 is selected from the group consisting of napthyl
- CH and Y and Z are each selected from the
- X, Y and Z are each selected from the group consisting of N and CH,
- novel pyrazole derivatives surprisingly show high binding affinities for either or both of the CB1 and CB2 cannabinoid receptors.
- Some of the novel pyrazole analogs are cannabinoid receptor antagonists that prevent binding of endogenous agonists to the cannabinoid receptors and thereby block the biological actions of such endogenous agonists.
- Other novel analogs are cannabinoid receptor agonists.
- inventive analogs described herein, and physiologically acceptable salts thereof have high potential when administered in therapeutically effective amounts for providing a physiological effect useful to treat pain, peripheral pain, glaucoma, epilepsy, nausea such as associated with cancer chemotherapy, AIDS Wasting Syndrome, cancer, neurodegenerative diseases including Multiple Sclerosis, Parkinson's Disease, Huntington's Chorea and Alzheimer's Disease, mental disorders such as Schizophrenia and depression; to suppress appetite; to reduce fertility; to prevent or reduce diseases associated with motor function such as Tourette's syndrome; to prevent or reduce inflammation; to provide neuroprotection; to modulate the immune system; to produce vasoconstriction or vasodilation and to effect memory enhancement.
- another aspect of the invention is the administration of a therapeutically effective amount of an inventive compound, or a physiologically acceptable salt thereof, to an individual or animal to provide a physiological effect.
- novel pyrazole derivatives have functional moieties such as halogen, azide and isothiocyanate and are potentially useful diagnostic agents in vivo (PET, SPECT).
- Other novel pyrazole derivatives are radioligands that are potentially useful experimental tools for cannabinoid receptor studies.
- a "therapeutically effective amount" of a compound is the quantity of a compound which, when administered to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a discernible increase or decrease in stimulation of cannabinoid receptors.
- Physiological effects that result from cannabinoid receptor stimulation include analgesia, decreased nausea resulting from chemotherapy, sedation and increased appetite. Other physiological functions include relieving intraocular pressure in glaucoma patients and suppression of the immune system.
- a "therapeutically effective amount" of the compound ranges from about 10 mg/day to about 1 ,000 mg/day.
- an "individual” refers to a human.
- An “animal” refers to, for example, veterinary animals, such as dogs, cats, horses and the like, and farm animals, such as cows, pigs and the like.
- the compound of the present invention can be administered by a variety of known methods, including orally, rectally, or by parenteral routes (e.g., intramuscular, intravenous, subcutaneous, nasal or topical).
- parenteral routes e.g., intramuscular, intravenous, subcutaneous, nasal or topical.
- the form in which the compounds are administered will be determined by the route of administration.
- Such forms include, but are not limited to, capsular and tablet formulations (for oral and rectal administration), liquid formulations (for oral, intravenous, intramuscular or subcutaneous administration) and slow releasing microcarriers (for rectal, intramuscular or intravenous administration).
- the formulations can also contain a physiologically acceptable vehicle and optional adjuvants, flavorings, colorants and preservatives.
- Suitable physiologically to acceptable vehicles may include, for example, saline, sterile water, Ringer's solution, and isotonic sodium chloride solutions.
- the specific dosage level of active ingredient will depend upon a number of factors, including, for example, biological activity of the particular preparation, age, body weight, sex and general health of the individual being treated.
- inventive pyrazole derivatives can generally be described with reference to structural Formula 1 :
- R 3 is selected from the group consisting of H and a branched or unbranched chain having the structure (CH 2 ) n CH 3 where n is an integer from 0 to about 3.
- R 4 , R 5 and R 6 are each selected from the group consisting of halogen, N 3 , NCS, OCH 3 , CH 3 , CH 2 CH 3 , NO 2 , NH 2 , phenyl and phenyl with at least one substituent from the group consisting of halogen, N 3 , NCS, OCH 3 , CH 3 , CH 2 CH 3 , N0 2 , and NH 2 .
- R 2 is selected from the group consisting of napthyl
- CH and Y and Z are each selected from the
- UCON/1 56/PC ere X, Y and Z are each selected from the up consisting of N and CH, where R 4 , R 5 and R 6 are each selected from the group consisting of halogen, N 3 , NCS, OCH 3 , CH 3 , CH 2 CH 3 , NO 2 , NH 2 and phenyl,
- Flash column chromatography was carried out using Whatman active silica gel (230 - 400 mesh) and eluents were distilled before use. Solvents for reactions were dried or purified as required. Reactions were carried out under nitrogen atmospheres unless otherwise noted.
- Lithium salt of ethyl 2,4-dioxo-3-methyl-4-phenylbutanoate To a magnetically stirred solution of lithium bis(trimethylsilyl)amide (40 ml, 1 .0 M solution in hexane, 40 mmol) in diethyl ether ( 1 20 mL) was added a solution of propiophenone (5.37 g, 40 mmol) in diethyl ether (50 mL) at 78 °C. The mixture was stirred at the same temperature for an additional 45 min, after which diethyl oxalate (6.4 mL, 47 mmol) was added to the mixture.
- the reaction mixture was allowed to warm to room temperature and stirred for
- reaction mixture was then quenched by saturated aqueous ammonium chloride and extracted with diethyl ether (3 ⁇ , 50 mL each). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated. Purification by flash column chromatography on silica gel with a petroleum ether/acetone (9: 1 ) mixture gave compound 9 as a white solid (0.296 g, 77% yield).
- Compound 6 was prepared from the methyl ester according to the procedure described for the compound 1 -5 and 7-8. The materials were tested for CB2 receptor binding affinity and for CB1 receptor affinity (to determine selectivity for the CB2 receptor). As used herein,
- binding affinity is represented by the IC 50 value which is the concentration of an analog required to occupy 50% of the total number (Bmax) of the receptors.
- an analog is said to have "binding selectivity" if it has higher binding affinity for one receptor compared to the other receptor; e.g. a cannabinoid analog which has an IC 50 of 0.1 nM for CB1 and 10 nM for CB2, is 100 times more selective for the CB1 receptor.
- the binding affinities (K,) are expressed in nanomoles (nM) and are listed in TABLE 1 .
- membranes were prepared from rat forebrain membranes according to the procedure of P.R.
- Membranes previously frozen at -80°C, were thawed on ice. To the stirred suspension was added three volumes of TME (25mM Tris-HCI buffer, 5 mM MgCI 2 and 1 mM EDTA) at pH 7.4. The suspension was incubated at 4°C for 30 min. At the end of the incubation, the membranes were pelleted and washed three times with TME. The treated membranes were subsequently used in the binding assay described below.
- TME 25mM Tris-HCI buffer, 5 mM MgCI 2 and 1 mM EDTA
- Compound SR141 71 6A a known pyrazole derivative, has a cannabinoid receptor affinity (K,) of 1 1 .5 nM for the CB1 receptor and 1 640 nM for the CB2 receptor.
- K cannabinoid receptor affinity
- all of the inventive compounds have receptor affinities much higher than compound SR141 71 6A for at least one of the CB1 or CB2 receptors.
- most of the inventive pyrazole derivatives have receptor affinities much higher (lower numerically) than compound SR141 71 6A for both of the CB1 and CB2 receptors.
- Muller-Vahl KB Schneider U, Kolbe H, Emrich, HM. Treatment of Tourette's syndrome with delta-9-tetrahvdrocannabinol. Am. J. Psychiat. (1 999) 1 56-1 95.
- Muller-Vahl KB Kolbe H, Schneider U, Emrich, HM Cannabis in movement disorders. Porsch. Kompicmentarmed (1 999) 6 (suppl. 3) 23-27. Consroe P, Musty R, Rein J, Tillery W, Pertwee R. The perceived effects of smoked cannabis on patents with multiple sclerosis, Eur. Neurol. (1 997) 38-44-48. Pinnegan-Ling D, Musty R. Marinol and phantom limb pain: a case study. Proc Inv. Cannabinoid Rea. Sec. (1 994):53. Brenneisen R, Pgli A, Elsohly MA, Henn V.
- inventive analogs described herein, and physiologically acceptable salts thereof have high potential when administered in therapeutically effective amounts for providing a physiological effect useful to treat pain, peripheral pain, glaucoma, epilepsy, nausea such as associated with cancer chemotherapy, AIDS Wasting Syndrome, cancer, neurodegenerative diseases including Multiple Sclerosis, Parkinson's Disease, Huntington's Chorea and Alzheimer's Disease, mental disorders such as Schizophrenia and depression; to suppress appetite; to reduce fertility; to prevent or reduce diseases associated with motor function such as Tourette's syndrome; to prevent or reduce inflammation; to provide neuroprotection; to modulate the immune system; to produce vasoconstriction or vasodilation and to effect memory enhancement.
- another aspect of the invention is the administration of a therapeutically effective amount of an inventive compound, or a physiologically acceptable salt thereof, to an individual or animal to provide a physiological effect.
Abstract
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Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA02005100A MXPA02005100A (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists. |
US10/110,865 US7119108B1 (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
DE60023167T DE60023167T2 (en) | 1999-10-18 | 2000-10-18 | PYRAZOL DERIVATIVES AS CANNABINOID RECEPTOR ANTAGONISTS |
AU19689/01A AU780572B2 (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
CA002387892A CA2387892A1 (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
EP00982694A EP1224173B1 (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
JP2001531807A JP2003512357A (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
US11/166,835 US8084467B2 (en) | 1999-10-18 | 2005-06-24 | Pyrazole derivatives as cannabinoid receptor antagonists |
US11/244,770 US7745440B2 (en) | 1999-10-18 | 2005-10-06 | Pyrazole analogs acting on cannabinoid receptors |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US15999399P | 1999-10-18 | 1999-10-18 | |
US60/159,993 | 1999-10-18 |
Related Child Applications (4)
Application Number | Title | Priority Date | Filing Date |
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US10110865 A-371-Of-International | 2000-10-18 | ||
PCT/US2002/027644 Continuation WO2003020217A2 (en) | 1999-10-18 | 2002-08-29 | Novel pyrazole analogs acting on cannabinoid receptors |
US11/166,835 Continuation-In-Part US8084467B2 (en) | 1999-10-18 | 2005-06-24 | Pyrazole derivatives as cannabinoid receptor antagonists |
US11/244,770 Continuation US7745440B2 (en) | 1999-10-18 | 2005-10-06 | Pyrazole analogs acting on cannabinoid receptors |
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WO2001029007A1 true WO2001029007A1 (en) | 2001-04-26 |
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PCT/US2000/041239 WO2001029007A1 (en) | 1999-10-18 | 2000-10-18 | Pyrazole derivatives as cannabinoid receptor antagonists |
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EP (1) | EP1224173B1 (en) |
JP (1) | JP2003512357A (en) |
AU (1) | AU780572B2 (en) |
CA (1) | CA2387892A1 (en) |
DE (1) | DE60023167T2 (en) |
MX (1) | MXPA02005100A (en) |
WO (1) | WO2001029007A1 (en) |
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WO2004026301A1 (en) * | 2002-09-19 | 2004-04-01 | Solvay Pharmaceuticals B.V. | 1h-1,2,4-triazole-3-carboxamide derivatives as cannabinoid-cb1 receptor ligands |
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US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
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AU2006203845A1 (en) * | 2005-01-10 | 2006-07-13 | Alexandros Makriyannis | Novel heteropyrrole analogs acting on cannabiniod receptors |
FR2978660B1 (en) * | 2011-08-05 | 2013-09-20 | Oreal | USE OF CB1 RECEPTOR ANTAGONIST AS A WHITENING AND / OR ANTI-BLINDING AGENT FOR KERATINIC MATERIALS |
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FR2692575B1 (en) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | NOVEL PYRAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
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FR2742148B1 (en) * | 1995-12-08 | 1999-10-22 | Sanofi Sa | NOVEL PYRAZOLE-3-CARBOXAMIDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
EP1176140B1 (en) * | 1999-02-10 | 2004-12-29 | Mitsubishi Pharma Corporation | Amide compounds and medicinal use thereof |
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- 2000-10-18 WO PCT/US2000/041239 patent/WO2001029007A1/en active IP Right Grant
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Also Published As
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DE60023167D1 (en) | 2006-02-23 |
JP2003512357A (en) | 2003-04-02 |
CA2387892A1 (en) | 2001-04-26 |
AU780572B2 (en) | 2005-04-07 |
MXPA02005100A (en) | 2003-09-25 |
DE60023167T2 (en) | 2006-06-14 |
EP1224173A1 (en) | 2002-07-24 |
EP1224173A4 (en) | 2002-11-20 |
EP1224173B1 (en) | 2005-10-12 |
AU1968901A (en) | 2001-04-30 |
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