US20200102311A1 - Monoacylglycerol Lipase Modulators - Google Patents
Monoacylglycerol Lipase Modulators Download PDFInfo
- Publication number
- US20200102311A1 US20200102311A1 US16/586,263 US201916586263A US2020102311A1 US 20200102311 A1 US20200102311 A1 US 20200102311A1 US 201916586263 A US201916586263 A US 201916586263A US 2020102311 A1 US2020102311 A1 US 2020102311A1
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- US
- United States
- Prior art keywords
- methyl
- pyrazol
- hexahydro
- epiminocycloocta
- methanone
- 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.)
- Abandoned
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged 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
- A61K31/33—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Definitions
- the present invention is related to certain bridged chemical entities having MGL (monoacylglycerol lipase) modulating properties, pharmaceutical compositions comprising these chemical entities, chemical processes for preparing these chemical entities and their use in the treatment of diseases, disorders or conditions associated with MGL receptor activity in subjects, in particular humans.
- MGL monoacylglycerol lipase
- Cannabis sativa and analogs of ⁇ 9 -tetrahydrocannabinol have been used since the days of folk medicine for therapeutic purposes.
- the endocannabinoid system consists of two G-protein coupled receptors, cannabinoid receptor type 1 (CB1) (Matsuda et al., Nature, 1990, 346, 561-4) and cannabinoid receptor type 2 (CB2) (Munro et al., Nature, 1993, 365, 61-5).
- CB1 receptor is one of the most abundant G-protein coupled receptor expressed in the brain (Herkenam et al., Proc. Nat. Acad. Sci., 1990, 87 (5), 1932-1936).
- CB1 is also expressed peripherally in the liver, gastrointestinal tract, pancreas, adipose tissue and skeletal muscles (Di Marzo et al., Curr Opin Lipidol, 2007, 18, 129-140).
- CB2 is predominantly expressed in immune cells such as monocytes (Pacher et al., Amer J Physiol, 2008, 294, H1133-H1134) and under certain conditions (inflammation) in the brain ((Benito et al., Brit J Pharmacol, 2008, 153, 277-285) and in skeletal (Cavuoto et al., Biochem Biophys Res Commun, 2007, 364, 105-110) and cardiac muscles (Hajrasouliha et al., Eur J Pharmacol, 2008, 579, 246-252).
- N-arachidonoylethanolamine (AEA or anandamide) was found to be an endogenous ligand for cannabinoid receptors (Devane et al., Science, 1992, 258, 1946-9). Subsequently, 2-arachidonoylglycerol (2-AG) was also identified as an additional endogenous ligand for the cannabinoid receptors (Mechoulam et al., Biochem Pharmacol, 1995, 50, 83-90; Sugiura et al., Biochem Biophys Res Commun, 1995, 215, 89-97).
- endocannabinoids signal through a retrograde mechanism. They are synthesized on demand in postsynaptic neurons and then rapidly degraded following binding to presynaptic cannabinoid receptors (Ahn et al., Chem Rev. 2008, 108(5): 1687-707).
- Monoacylglycerol lipase (MGLL, also known as MAG lipase and MGL) is the serine hydrolase responsible for the degradation of 2-AG into arachidonic acid and glycerol in the central nervous system (Mechoulam et al., Biochem Pharmacol, 1995, 50, 83-90; Sugiura et al., Biochem Biophys Res Commun, 1995, 215, 89-97; Long et al., Nat Chem Biol. 2009 January; 5(1):37-44;), Schlosburg et al, Nat Neurosci., 2010, September; 13(9):1113-9) and peripheral tissues (Long et al., Chem Biol., 2009 Jul. 31; 16(7):744-53).
- Anandamide is hydrolyzed by fatty acid amide hydrolase (FAAH) (Piomelli, Nat Rev Neurosci, 2003, 4, 873-884).
- MGL exists in both soluble and membrane bound forms (Dinh et al., Proc Natl Acad Sci USA., 2002, Aug. 6; 99(16):10819-24).
- MGL is located in presynaptic neurons (Straiker et al., Mol Pharmacol., 2009, December; 76(6):1220-7) and astrocytes (Walter et al., J Neurosci., 2004, Sep. 15; 24(37):8068-74) within regions associated with high CB1 receptor density.
- genetic ablation of MGL expression produces 10-fold increase in brain 2-AG levels without affecting anandamide concentration (Schlosburg et al., Nat Neurosci., 2010, September; 13(9): 1113-9).
- MGL modulation offers an interesting strategy for potentiating the cannabinoid system.
- the primary advantage of this approach is that only brain regions where endocannabinoids are actively produced will be modulated, potentially minimizing the side effects associated with exogenous CB1 agonists.
- Pharmacological inactivation of MGL by covalent inhibitors in animals increase 2-AG content in brain and peripheral tissues and has been found to produce antinociceptive, anxiolytic and anti-inflammatory effects that are dependent on CB1 and/or CB2 receptors (Long et al., Nat Chem Biol., 2009, January, 5(1):37-44; Ghosh et al., Life Sci., 2013, Mar.
- MGL modulation leads to reduction in proinflammatory prostanoid signaling in animal models of traumatic brain injury (Katz et al., J Neurotrauma., 2015, Mar. 1; 32(5):297-306; Zhang et al., J Cereb Blood Flow Metab., 2015, Mar. 31; 35(4):706), neurodegeneration including Alzheimer's disease (Piro et al., Cell Rep., 2012, Jun. 28, 1(6):617-23; Wenzel et al., Life Sci., 2018, Aug. 15, 207:314-322; Chen et al., Cell Rep., 2012, Nov.
- Parkinson's disease Nomura et al., Science, 2011, Nov. 11, 334(6057), 809-13; Pasquarelli et al., Neurochem Int., 2017, November, 110:14-24), amyotrophic lateral sclerosis (Pasquarelli et al., Neuropharmacology, 2017, Sep. 15, 124:157-169), multiple sclerosis (Hernadez-Torres et al., Angew Chem Int Ed Engl., 2014, Dec.
- MGL modulation including MGL inhibition offers a compelling therapeutic approach for the treatment of a vast array of complex diseases.
- MGL modulation, including MGL inhibition in animals does not produces the full spectrum of neurobehavioral effects observed with ⁇ 9 -tetrahydrocannabinol and other CB1 agonists (Tuo et al., J Med Chem., 2017, Jan. 12, 60(1), 4-46; Mulvihill et al., Life Sci., 2013, Mar. 19, 92(8-9), 492-7).
- Endocannabinoid hypoactivity is a risk factor for the treatment of depression, anxiety and post-traumatic stress disorders. Millennia of human use of Cannabis sativa , and a brief period in which humans were treated with the endocannabinoid antagonist, rimonabant, provide support for that hypothesis.
- 2-AG levels are decreased in individuals with major depression (Hill et al., Pharmacopsychiatry., 2008, March; 41(2): 48-53; Hill et al., Psychoneuroendocrinology., 2009, September; 34(8): 1257-1262.). Low circulating 2-AG levels predict rates of depression (Hauer et al., Rev Neurosci., 2012, 23(5-6):681-90).
- Reduced circulating 2-AG has been found in patient with post-traumatic stress disorder (PTSD) (Hill et al., Psychoneuroendocrinology, 2013, 38 (12), 2952-2961). Healthy volunteers exposed to chronic stressors exhibited progressively diminished circulating 2-AG levels which correlated with the onset of reductions in measures of positive emotions (Yi et al., Progress in Neuro - Psychopharmacology and Biological Psychiatry, 2016, 67 (3), 92-97). The CB1 receptor inverse agonist/antagonist Rimonabant has been withdrawn from the market due to the high incidence of severe depression and suicidal ideation (Christensen et al., The Lancet, 2007, 370, 1706-1713). Therefore, MGL modulators are potentially useful for the treatment of mood disorders, anxiety and PTSD.
- PTSD post-traumatic stress disorder
- Cannabinoid receptor agonists are clinically used to treat pain, spasticity, emesis and anorexia (Di Marzo, et al., Annu Rev Med., 2006, 57:553-74; Ligresti et al., Curr Opin Chem Biol., 2009, June; 13(3):321-31). Therefore, MGL modulators, including MGL inhibitors are also potentially useful for these indications.
- MGL exerts CB1-dependant antinociceptive effects in animal models of noxious chemical, inflammatory, thermal and neuropathic pain (Guindon et al., Br J Pharmacol., 2011, August; 163(7):1464-78; Kinsey et al., J Pharmacol Exp Ther., 2009, September; 330(3):902-10; Long et al., Nat Chem Biol., 2009, January; 5(1):37-44).
- MGL blockade reduces mechanical and acetone induced cold allodynia in mice subjected to chronic constriction injury of the sciatic nerve (Kinsey et al., J Pharmacol Exp Ther., 2009, September; 330(3):902-10).
- MGL inhibition produces opiate-sparing events with diminished tolerance, constipation, and cannabimimetic side effects (Wilkerson et al., J Pharmacol Exp Ther., 2016, April; 357(1):145-56).
- MGL blockade is protective in model of inflammatory bowel disease (Alhouayek et al., FASEB J., 2011, August; 25(8):2711-21).
- MGL inhibition also reverse Paclitaxel-induced nociceptive behavior and proinflammatory markers in a mouse model of chemotherapy-induced neuropathy (Curry et al., J Pharmacol Exp Ther., 2018, July; 366(1):169-18).
- MGL inhibitors are also potentially useful for the treatment of chronic inflammatory condition of the urinary bladder like interstitial cystitis (Chinnadurai et al., Med Hypotheses 2019, October; 131: 109321).
- MGL is upregulated in aggressive human cancer cells and primary tumors where it has a unique role of providing lipolytic sources of free fatty acids for synthesis of oncogenic signaling lipids that promote cancer aggressiveness.
- MGL in cancer plays a distinct role in modulating the fatty acid precursor pools for synthesis of protumorigenic signaling lipids in malignant human cancer cells.
- MGL blockade shows anti-emetic and anti-nausea effects in a lithium chloride model of vomiting in shrews (Sticht et al., Br J Pharmacol., 2012, April, 165(8):2425-35).
- MGL modulators including MGL inhibitors may have utility in modulating drug dependence of opiates.
- MGL blockade reduce the intensity of naloxone-precipitated morphine withdrawal symptoms in mice.
- MGL blockade also attenuated spontaneous withdrawal signs in morphine-dependent mice (Ramesh et al., J Pharmacol Exp Ther., 2011, October, 339(1):173-85).
- MGL modulators are also potentially useful for the treatment of eye conditions, including but not limited to, glaucoma and disease states arising from elevated intraocular pressure (Miller et al., Pharmaceuticals, 2018, 11, 50).
- Embodiments of the present invention relate to chemical entities, pharmaceutical compositions containing them, methods of making and purifying them, and methods for using them the treatment of diseases, disorders, and conditions associated with the MGL modulation.
- An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or condition associated with the MGL modulation using at least one chemical entity of the invention.
- Embodiments of this invention are compounds of Formula (I),
- Embodiments of this invention are also compounds of Formula (II),
- alkyl refers to a straight- or branched-chain alkyl group having from 1 to 8 carbon atoms in the chain.
- alkyl groups include methyl (Me), ethyl (Et), n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl (tBu), pentyl, isopentyl, tert-pentyl, hexyl, isohexyl, and groups that in light of the ordinary skill in the art and the teachings provided herein would be considered equivalent to any one of the foregoing examples.
- C 1 -C 4 alkyl refers to straight- or branched-chain alkyl group having from 1 to 4 carbon atoms in the chain.
- cycloalkyl refers to a saturated or partially saturated, monocyclic, fused polycyclic, or spiro polycyclic carbocycle having from 3 to 12 ring atoms per carbocycle.
- Illustrative examples of cycloalkyl groups include the following entities, in the form of properly bonded moieties:
- halogen or “halo” represents chlorine, fluorine, bromine, or iodine.
- haloalkyl refers to a straight- or branched-chain alkyl group having from 1 to 6 carbon atoms in the chain optionally substituting hydrogens with halogens.
- C 1 -C 4 haloalkyl refers to a straight- or branched-chain alkyl group having from 1 to 4 carbon atoms in the chain, optionally substituting hydrogens with halogens.
- haloalkyl groups include trifluoromethyl (CF 3 ), difluoromethyl (CF 2 H), monofluoromethyl (CH 2 F), pentafluoroethyl (CF 2 CF 3 ), tetrafluoroethyl (CHFCF 3 ), monofluoroethyl (CH 2 CH 2 F), trifluoroethyl (CH 2 CF 3 ), tetrafluorotrifluoromethylethyl (CF(CF 3 ) 2 ), and groups that in light of the ordinary skill in the art and the teachings provided herein would be considered equivalent to any one of the foregoing examples.
- aryl refers to a monocyclic, aromatic carbocycle (ring structure having ring atoms that are all carbon) having 6 atoms per ring (Carbon atoms in the aryl groups are sp2 hybridized.)
- phenyl represents the following moiety:
- heteroaryl refers to an aromatic monocyclic or multicyclic ring system comprising 5 to 14 ring atoms, wherein from 1 to 4 of the ring atoms is independently O, N or S and the remaining ring atoms are carbon atoms.
- a heteroaryl group has 5 to 10 ring atoms.
- a heteroaryl group is monocyclic and has 5 or 6 ring atoms.
- a heteroaryl group is monocyclic and has 5 or 6 ring atoms and at least one nitrogen ring atom.
- heteroaryl group is joined via a ring carbon atom and any nitrogen atom of a heteroaryl can be optionally oxidized to the corresponding N-oxide.
- heteroaryl also encompasses a heteroaryl group, as defined above, which has been fused to a benzene ring.
- 5-membered heteroaryl refers to a heteroaryl group, as defined above, which has 5 ring atoms.
- Non-limiting examples of illustrative 5-membered heteroaryls include:
- 6-membered heteroaryl refers to a heteroaryl group, as defined above, which has 6 ring atoms.
- Non-limiting examples of illustrative 6-membered heteroaryls include:
- 5,6-fused bicyclic heteroaryl or 6,5-fused bicyclic heteroaryl refers to a heteroaryl group, as defined above, which has 9 ring atoms.
- Non-limiting examples of illustrative 5,6-fused bicyclic heteroaryl or 6,5-fused bicyclic heteroaryl include:
- 6,6-fused bicyclic heteroaryl refers to a heteroaryl group, as defined above, which has 9 ring atoms.
- Non-limiting examples of illustrative 6,6-fused bicyclic heteroaryl include:
- substituted means that the specified group or moiety bears one or more substituents.
- unsubstituted means that the specified group bears no substituents.
- optionally substituted means that the specified group is unsubstituted or substituted by one or more substituents. Where the term “substituted” is used to describe a structural system, the substitution is meant to occur at any valency-allowed position on the system.
- variable point of attachment means that a group is allowed to be attached at more than one alternative position in a structure.
- the attachment will always replace a hydrogen atom on one of the ring atoms.
- all permutations of bonding are represented by the single diagram, as shown in the illustrations below.
- substituted means that the specified group or moiety bears one or more substituents.
- unsubstituted means that the specified group bears no substituents.
- optionally substituted means that the specified group is unsubstituted or substituted by one or more substituents. Where the term “substituted” is used to describe a structural system, the substitution is meant to occur at any valency-allowed position on the system.
- any formula given herein is intended to represent compounds having structures depicted by the structural formula as well as certain variations or forms.
- compounds of any formula given herein may have asymmetric centers and therefore exist in different enantiomeric forms. All optical isomers and stereoisomers of the compounds of the general formula, and mixtures thereof, are considered within the scope of such formula.
- the compounds of this invention may possess one or more asymmetric centers; such compounds can therefore be produced as individual (R)- or (S)-stereoisomers or as mixtures thereof.
- any formula given herein is intended to represent a racemate, one or more of its enantiomeric forms, one or more of its diastereomeric forms, and mixtures thereof.
- any formula given herein is intended to refer also to any one of hydrates, solvates, polymorphs and of such compounds, and mixtures thereof, even if such forms are not listed explicitly.
- R at a stereocenter designates that the stereocenter is purely of the R-configuration as defined in the art; likewise, the term “S” means that the stereocenter is purely of the S-configuration.
- RS refers to a stereocenter that exists as a mixture of the R- and S-configurations.
- Compounds containing one stereocenter drawn without a stereo bond designation are a mixture of 2 enantiomers.
- Compounds containing 2 stereocenters both drawn without stereo bond designations are a mixture of 4 diastereomers.
- Compounds with 2 stereocenters both labeled “RS” and drawn with stereo bond designations are a 2-component mixture with relative stereochemistry as drawn.
- Unlabeled stereocenters drawn without stereo bond designations are a mixture of the R- and S-configurations. For unlabeled stereocenters drawn with stereo bond designations, the absolute stereochemistry is as depicted.
- references to a compound herein stands for a reference to any one of: (a) the actually recited form of such compound, and (b) any of the forms of such compound in the medium in which the compound is being considered when named.
- reference herein to a compound such as R—COOH encompasses reference to any one of, for example, R—COOH(s), R—COOH(sol), and R—COO-(sol).
- R—COOH(s) refers to the solid compound, as it could be for example in a tablet or some other solid pharmaceutical composition or preparation
- R—COOH(sol) refers to the undissociated form of the compound in a solvent
- R—COO-(sol) refers to the dissociated form of the compound in a solvent, such as the dissociated form of the compound in an aqueous environment, whether such dissociated form derives from R—COOH, from a salt thereof, or from any other entity that yields R—COO— upon dissociation in the medium being considered.
- an expression such as “exposing an entity to compound of formula R—COOH” refers to the exposure of such entity to the form, or forms, of the compound R—COOH that exists, or exist, in the medium in which such exposure takes place.
- an expression such as “reacting an entity with a compound of formula R—COOH” refers to the reacting of (a) such entity in the chemically relevant form, or forms, of such entity that exists, or exist, in the medium in which such reacting takes place, with (b) the chemically relevant form, or forms, of the compound R—COOH that exists, or exist, in the medium in which such reacting takes place.
- any formula given herein is also intended to represent unlabeled forms as well as isotopically labeled forms of the compounds.
- Isotopically labeled compounds have structures depicted by the formulas given herein except that one or more atoms are replaced by an atom having a selected atomic mass or mass number in an enriched form.
- isotopes that can be incorporated into compounds of the invention in a form that exceeds natural abundances include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorous, fluorine, chlorine, and iodine, such as 2 H (or chemical symbol D), 3 H (or chemical symbol T), 11 C, 13 C, 14 C, 15 N, 18 O, 17 O, 31 P, 32 P, 35 S, 18F, 36 Cl, and 125 I, respectively.
- Such isotopically labelled compounds are useful in metabolic studies (preferably with 14 C), reaction kinetic studies (with, for example 2 H or 3 H), detection or imaging techniques [such as positron emission tomography (PET) or single-photon emission computed tomography (SPECT)] including drug or substrate tissue distribution assays, or in radioactive treatment of patients.
- PET positron emission tomography
- SPECT single-photon emission computed tomography
- an 18 F or 11 C labeled compound may be particularly preferred for PET or SPECT studies.
- substitution with heavier isotopes such as deuterium (i.e., 2 H, or D) may afford certain therapeutic advantages resulting from greater metabolic stability, for example increased in vivo half-life or reduced dosage requirements.
- Isotopically labeled compounds of this invention can generally be prepared by carrying out the procedures disclosed in the schemes or in the examples and preparations described below by substituting a readily available isotopically labeled reagent for a non-isotopically labeled reagent.
- C n-m alkyl refers to an aliphatic chain, whether straight or branched, with a total number N of carbon members in the chain that satisfies n ⁇ N ⁇ m, with m>n.
- each of groups Q and R can be H or F
- the choice of H or F for Q is made independently of the choice of H or F for R, so the choice of assignment for Q does not determine or condition the choice of assignment for R, or vice-versa, unless it is expressly indicated otherwise.
- Illustrative claim recitation in this regard would read as “each of Q and R is independently H or F”, or “each of Q and R is independently selected from the group consisting of H and F”.
- a zwitterionic compound would be encompassed herein by referring to a compound that is known to form a zwitterion, even if it is not explicitly named in its zwitterionic form.
- Terms such as zwitterion, zwitterions, and their synonyms zwitterionic compound(s) are standard IUPAC-endorsed names that are well known and part of standard sets of defined scientific names.
- the name zwitterion is assigned the name identification CHEBI:27369 by the Chemical Entities of Biological Interest (ChEBI) dictionary of molecular entities.
- a zwitterion or zwitterionic compound is a neutral compound that has formal unit charges of opposite sign.
- aminoethanoic acid (the amino acid glycine) has the formula H 2 NCH 2 COOH, and it exists in some media (in this case in neutral media) in the form of the zwitterion + H 3 NCH 2 COO ⁇ .
- Zwitterions, zwitterionic compounds, inner salts and dipolar ions in the known and well-established meanings of these terms are within the scope of this invention, as would in any case be so appreciated by those of ordinary skill in the art.
- embodiments of this invention comprise the various groupings that can be made from the listed assignments, taken independently, and equivalents thereof.
- substituent S example is one of S 1 , S 2 , and S 3
- this listing refers to embodiments of this invention for which S example is S 1 ; S example is S 2 ; S example is S 3 ; S example is one of S 1 and S 2 ; S example is one of S 1 and S 3 ; S example is one of S 2 and S 3 ; S example is one of S 1 , S 2 and S 3 ; and S example is any equivalent of each one of these choices.
- C i -C j when applied herein to a class of substituents, is meant to refer to embodiments of this invention for which each and every one of the number of carbon members, from i to j including i and j, is independently realized.
- the term C 1 -C 3 refers independently to embodiments that have one carbon member (C 1 ), embodiments that have two carbon members (C 2 ), and embodiments that have three carbon members (C 3 ).
- a “pharmaceutically acceptable salt” is intended to mean a salt of an acid or base of a compound represented by Formula (I) (as well as compounds of Formula (II)) that is non-toxic, biologically tolerable, or otherwise biologically suitable for administration to the subject. See, generally, S. M. Berge, et al., “Pharmaceutical Salts”, J. Pharm. Sci., 1977, 66:1-19, and Handbook of Pharmaceutical Salts, Properties, Selection, and Use , Stahl and Wermuth, Eds., Wiley-VCH and VHCA, Zurich, 2002.
- Preferred pharmaceutically acceptable salts are those that are pharmacologically effective and suitable for contact with the tissues of patients without undue toxicity, irritation, or allergic response.
- a compound of Formula (I) (as well as compounds of Formula (II)) may possess a sufficiently acidic group, a sufficiently basic group, or both types of functional groups, and accordingly react with a number of inorganic or organic bases, and inorganic and organic acids, to form a pharmaceutically acceptable salt.
- Examples of pharmaceutically acceptable salts include sulfates, pyrosulfates, bisulfates, sulfites, bisulfites, phosphates, monohydrogen-phosphates, dihydrogenphosphates, metaphosphates, pyrophosphates, chlorides, bromides, iodides, acetates, propionates, decanoates, caprylates, acrylates, formates, isobutyrates, caproates, heptanoates, propiolates, oxalates, malonates, succinates, suberates, sebacates, fumarates, maleates, butyne-1,4-dioates, hexyne-1,6-dioates, benzoates, chlorobenzoates, methylbenzoates, dinitrobenzoates, hydroxybenzoates, methoxybenzoates, phthalates, sulfonates, xylenesulfonates, phenylacetates, phen
- Compounds of Formula (I) may contain at least one nitrogen of basic character, so desired pharmaceutically acceptable salts may be prepared by any suitable method available in the art, for example, treatment of the free base with an inorganic acid, such as hydrochloric acid, hydrobromic acid, sulfuric acid, sulfamic acid, nitric acid, boric acid, phosphoric acid, and the like, or with an organic acid, such as acetic acid, phenylacetic acid, propionic acid, stearic acid, lactic acid, ascorbic acid, maleic acid, hydroxymaleic acid, isethionic acid, succinic acid, valeric acid, fumaric acid, malonic acid, pyruvic acid, oxalic acid, glycolic acid, salicylic acid, oleic acid, palmitic acid, lauric acid, a pyranosidyl acid, such as glucuronic acid or galacturonic acid, an alpha-hydroxy acid,
- an inorganic acid such as hydrochlor
- Compounds of Formula (I) may contain a carboxylic acid moiety, a desired pharmaceutically acceptable salt may be prepared by any suitable method, for example, treatment of the free acid with an inorganic or organic base, such as an amine (primary, secondary or tertiary), an alkali metal hydroxide, alkaline earth metal hydroxide, any compatible mixture of bases such as those given as examples herein, and any other base and mixture thereof that are regarded as equivalents or acceptable substitutes in light of the ordinary level of skill in this technology.
- an inorganic or organic base such as an amine (primary, secondary or tertiary), an alkali metal hydroxide, alkaline earth metal hydroxide, any compatible mixture of bases such as those given as examples herein, and any other base and mixture thereof that are regarded as equivalents or acceptable substitutes in light of the ordinary level of skill in this technology.
- suitable salts include organic salts derived from amino acids, such as glycine and arginine, ammonia, carbonates, bicarbonates, primary, secondary, and tertiary amines, and cyclic amines, such as benzylamines, pyrrolidines, piperidine, morpholine, piperazine, N-methyl-glucamine and tromethamine and inorganic salts derived from sodium, calcium, potassium, magnesium, manganese, iron, copper, zinc, aluminum, and lithium.
- amino acids such as glycine and arginine
- ammonia carbonates, bicarbonates, primary, secondary, and tertiary amines
- cyclic amines such as benzylamines, pyrrolidines, piperidine, morpholine, piperazine, N-methyl-glucamine and tromethamine
- inorganic salts derived from sodium, calcium, potassium, magnesium, manganese, iron, copper, zinc, aluminum, and lithium.
- active agent or “active agents” of the present invention are useful as MGL-modulators in the methods of the invention.
- Such methods for modulating MGL comprise the use of a therapeutically effective amount of at least one chemical entity of the invention.
- the MGL modulator is an inhibitor and is used in a subject diagnosed with or suffering from a disease, disorder, or condition associated with MGL receptor activity, such as those described herein. Symptoms or disease states are intended to be included within the scope of “disease, disorders or conditions.”
- the invention relates to methods of using the active agents described herein to treat subjects diagnosed with or suffering from a disease, disorder, or condition associated with the MGL receptor activity.
- treat or “treating” as used herein is intended to refer to administration of an active agent or composition of the invention to a subject for the purpose of effecting a therapeutic or prophylactic benefit through modulation of MGL receptor activity. Treating includes reversing, ameliorating, alleviating, inhibiting the progress of, lessening the severity of, or preventing a disease, disorder, or condition, or one or more symptoms of such disease, disorder or condition associated with the MGL modulation.
- subject refers to a mammalian patient in need of such treatment, such as a human.
- composition refers to a product that includes the specified ingredients in therapeutically effective amounts, as well as any product that results, directly, or indirectly, from combinations of the specified ingredients in the specified amounts.
- MGL inhibitor is intended to encompass a compound that interacts with MGL to substantially reduce or eliminate its catalytic activity, thereby increasing the concentrations of its substrate(s).
- MGL-modulated is used to refer to the condition of being affected by the modulation of the MGL enzyme including the condition of being affected by the inhibition of the MGL enzyme.
- the disclosure is directed to methods for treating, ameliorating and/or preventing diseases, conditions, or disorders associated with pain (including inflammatory pain), and also psychiatric disorders, neurological disorders, cancers and eye conditions by the administration of therapeutically effective amounts of MGL modulators to subjects in need thereof.
- modulators include both inhibitors and activators, where “inhibitors” refer to compounds that decrease, prevent, inactivate, desensitize, or down-regulate the MGL expression or activity, and “activators” are compounds that increase, activate, facilitate, sensitize, or up-regulate MGL expression or activity.
- the term “affect” or “affected” when referring to a disease, condition or disorder that is affected by inhibition of MGL) includes a reduction in the frequency and/or severity of one or more symptoms or manifestations of said disease, condition or disorder; and/or include the prevention of the development of one or more symptoms or manifestations of said disease, condition or disorder or the development of the disease, condition or disorder.
- a therapeutically effective amount of at least one active agent according to the invention is administered to a subject suffering from or diagnosed as having such a disease, disorder, or condition.
- a “therapeutically effective amount” means an amount or dose sufficient to generally bring about the desired therapeutic or prophylactic benefit in subjects in need of such treatment for the designated disease, disorder, or condition.
- Effective amounts or doses of the active agents of the present invention may be ascertained by routine methods such as modeling, dose escalation studies or clinical trials, and by taking into consideration routine factors, e.g., the mode or route of administration or drug delivery, the pharmacokinetics of the agent, the severity and course of the disease, disorder, or condition, the subject's previous or ongoing therapy, the subject's health status and response to drugs, and the judgment of the treating physician.
- routine factors e.g., the mode or route of administration or drug delivery, the pharmacokinetics of the agent, the severity and course of the disease, disorder, or condition, the subject's previous or ongoing therapy, the subject's health status and response to drugs, and the judgment of the treating physician.
- routine factors e.g., the mode or route of administration or drug delivery, the pharmacokinetics of the agent, the severity and course of the disease, disorder, or condition, the subject's previous or ongoing therapy, the subject's health status and response to drugs, and the judgment of the treating physician.
- the dose may be adjusted for preventive or maintenance treatment.
- the dosage or the frequency of administration, or both may be reduced as a function of the symptoms, to a level at which the desired therapeutic or prophylactic effect is maintained.
- treatment may cease.
- Subjects may, however, require intermittent treatment on a long-term basis upon any recurrence of symptoms.
- the compounds of the invention are envisaged for use alone, in combination with one or more of other compounds of this invention, or in combination with additional active ingredients in the treatment of the conditions discussed below.
- the additional active ingredients may be co-administered separately with at least one compound of the invention, with active agents of the invention or included with such an agent in a pharmaceutical composition according to the invention.
- additional active ingredients are those that are known or discovered to be effective in the treatment of conditions, disorders, or diseases associated with the MGL modulation, such as another MGL inhibitor or a compound active against another target associated with the particular condition, disorder, or disease.
- the combination may serve to increase efficacy (e.g., by including in the combination a compound potentiating the potency or effectiveness of an agent according to the invention), decrease one or more side effects, or decrease the required dose of the active agent according to the invention.
- an “effective amount” means an amount sufficient to affect MGL modulation.
- a pharmaceutical composition of the invention comprises a therapeutically effective amount of at least one active agent in accordance with the invention.
- compositions commonly used in pharmaceutical compositions are substances that are non-toxic, biologically tolerable, and otherwise biologically suitable for administration to a subject, such as an inert substance, added to a pharmacological composition or otherwise used as a vehicle, carrier, or diluent to facilitate administration of an agent and that is compatible therewith.
- excipients include calcium carbonate, calcium phosphate, various sugars and types of starch, cellulose derivatives, gelatin, vegetable oils, and polyethylene glycols.
- compositions containing one or more dosage units of the active agents may be prepared using pharmaceutically acceptable excipients and compounding techniques known or that become available to those of ordinary skill in the art.
- the compositions may be administered in the inventive methods by a suitable route of delivery, e.g., oral, parenteral, rectal, topical, or ocular routes, or by inhalation.
- the preparation may be in the form of tablets, capsules, sachets, dragees, powders, granules, lozenges, powders for reconstitution, liquid preparations, or suppositories.
- the compositions may be formulated for any one of a plurality of administration routes, such as intravenous infusion, topical administration, or oral administration.
- the compositions may be formulated for oral administration.
- the active agents of the invention can be provided in the form of tablets or capsules, or as a solution, emulsion, or suspension.
- the active agents may be formulated to yield a dosage of, e.g., for a 70-kg human, an illustrative range for a suitable dosage amount is from about 1 to 1000 mg/day in single or multiple dosage units.
- Oral tablets may include the active ingredient(s) mixed with compatible pharmaceutically acceptable excipients such as diluents, disintegrating agents, binding agents, lubricating agents, sweetening agents, flavoring agents, coloring agents and preservative agents.
- suitable inert fillers include sodium and calcium carbonate, sodium and calcium phosphate, lactose, starch, sugar, glucose, methyl cellulose, magnesium stearate, mannitol, sorbitol, and the like.
- Exemplary liquid oral excipients include ethanol, glycerol, water, and the like.
- Starch, polyvinyl-pyrrolidone (PVP), sodium starch glycolate, microcrystalline cellulose, and alginic acid are exemplary disintegrating agents.
- Binding agents may include starch and gelatin.
- the lubricating agent if present, may be magnesium stearate, stearic acid or talc. If desired, the tablets may be coated with a material such as glyceryl monostearate or glyceryl distearate to delay absorption in the gastrointestinal tract, or may be coated with an enteric coating.
- Capsules for oral administration include hard and soft gelatin or (hydroxypropyl)methyl cellulose capsules.
- active ingredient(s) may be mixed with a solid, semi-solid, or liquid diluent.
- Liquids for oral administration may be in the form of suspensions, solutions, emulsions or syrups or may be lyophilized or presented as a dry product for reconstitution with water or other suitable vehicle before use.
- Such liquid compositions may optionally contain: pharmaceutically-acceptable excipients such as suspending agents (for example, sorbitol, methyl cellulose, sodium alginate, gelatin, hydroxyethylcellulose, carboxymethylcellulose, aluminum stearate gel and the like); non-aqueous vehicles, e.g., oil (for example, almond oil or fractionated coconut oil), propylene glycol, ethyl alcohol, or water; preservatives (for example, methyl or propyl p-hydroxybenzoate or sorbic acid); wetting agents such as lecithin; and, if desired, flavoring or coloring agents.
- suspending agents for example, sorbitol, methyl cellulose, sodium alginate, gelatin, hydroxyethylcellulose, carboxymethylcellulose, aluminum stearate gel and the like
- non-aqueous vehicles e.g., oil (for example, almond oil or fractionated coconut oil), propylene glycol, ethyl alcohol, or water
- compositions may be formulated for rectal administration as a suppository, enema or foam.
- parenteral use including intravenous, intramuscular, intraperitoneal, or subcutaneous routes, the agents of the invention may be provided in sterile aqueous solutions or suspensions, buffered to an appropriate pH and isotonicity or in parenterally acceptable oil.
- Suitable aqueous vehicles include Ringer's solution and isotonic sodium chloride.
- Such forms may be presented in unit-dose form such as ampules or disposable injection devices, in multi-dose forms such as vials from which the appropriate dose may be withdrawn, or in a solid form or pre-concentrate that can be used to prepare an injectable formulation.
- Illustrative infusion doses range from about 1 to 1000 ⁇ g/kg/minute of agent admixed with a pharmaceutical carrier over a period ranging from several minutes to several days.
- the agents may be mixed with a pharmaceutical carrier at a concentration of about 0.01% to about 20% of drug to vehicle, preferably 0.1% to 10%.
- a pharmaceutical carrier for topical administration, may be mixed with a pharmaceutical carrier at a concentration of about 0.01% to about 20% of drug to vehicle, preferably 0.1% to 10%.
- Another mode of administering the agents of the invention may utilize a patch formulation to affect transdermal delivery.
- Active agents may alternatively be administered in methods of this invention by inhalation, via the nasal or oral routes, e.g., in a spray formulation also containing a suitable carrier.
- the invention is directed to a method of treating a subject suffering from or diagnosed with a disease, disorder, or condition associated with MGL modulation, comprising administering to the subject in need of such treatment a therapeutically effective amount of the active agent.
- the compounds of Formula (I) are useful in methods for treating, ameliorating and/or preventing a disease, a condition or a disorder that is affected by the inhibition of MGL.
- Such methods comprise administering to a subject, including an animal, a mammal, and a human in need of such treatment, amelioration and/or prevention, a therapeutically effective amount of a compound of Formula (I) (as well as compounds of Formula (II)), or an enantiomer, diastereomer, solvate or pharmaceutically acceptable salt thereof.
- the compounds of Formula (I) (as well as compounds of Formula (II)), or pharmaceutically acceptable salts, isotopes, N-oxides, solvates and stereoisomers thereof, are useful for treating, ameliorating and/or preventing diseases, conditions, or disorders causing pain, psychiatric disorders, neurological disorders, cancers and eyes conditions.
- the compounds of Formula (I) (as well as compounds of Formula (II)), or pharmaceutically acceptable salts, isotopes, N-oxides, solvates and stereoisomers thereof, are useful for treating, ameliorating and/or preventing inflammatory pain, major depressive disorder, treatment resistant depression, anxious depression or bipolar disorder by administering to a subject in need thereof a therapeutically effective amount of a compound of Formula (I) (as well as compounds of Formula (II)), or a pharmaceutically acceptable salt, isotope, N-oxide, solvate or stereoisomer thereof as herein defined.
- inflammatory pain examples include, but are not limited to, pain due to a disease, condition, disorder, or a pain state including inflammatory bowel disease, visceral pain, migraine, post-operative pain, osteoarthritis, rheumatoid arthritis, back pain, lower back pain, joint pain, abdominal pain, chest pain, labor, musculoskeletal diseases, skin diseases, toothache, pyresis, burn, sunburn, snake bite, venomous snake bite, spider bite, insect sting, neurogenic bladder, interstitial cystitis, urinary tract infection, rhinitis, contact dermatitis/hypersensitivity, itch, eczema, pharyngitis, mucositis, enteritis, irritable bowel syndrome, cholecystitis, pancreatitis, postmastectomy pain syndrome, menstrual pain, endometriosis, pain due to physical trauma, headache, sinus headache, tension headache, or arachnoiditis.
- inflammatory hyperalgesia is inflammatory hyperalgesia/hypersensitivity.
- inflammatory hyperalgesia include a disease, condition, disorder, or pain state including inflammation, osteoarthritis, rheumatoid arthritis, back pain, joint pain, abdominal pain, musculoskeletal diseases, skin diseases, post-operative pain, headaches, toothache, burn, sunburn, insect sting, neurogenic bladder, urinary incontinence, interstitial cystitis, urinary tract infection, cough, asthma, chronic obstructive pulmonary disease, rhinitis, contact dermatitis/hypersensitivity and/or dermal allergy, itch, eczema, pharyngitis, enteritis, irritable bowel syndrome, inflammatory bowel diseases including Crohn's Disease, ulcerative colitis, benign prostatic hypertrophy, and nasal hypersensitivity.
- the present invention is directed to a method for treating, ameliorating and/or preventing inflammatory visceral hyperalgesia in which an enhanced visceral irritability exists, comprising, consisting of, and/or consisting essentially of the step of administering to a subject in need of such treatment a therapeutically effective amount of a compound of Formula (I) (as well as compounds of Formula (II)) or a pharmaceutically acceptable salt, isotope, N-oxide, solvate or stereoisomer thereof.
- the present invention is directed to a method for treating inflammatory somatic hyperalgesia in which a hypersensitivity to thermal, mechanical and/or chemical stimuli exists, comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of Formula (I) (as well as compounds of Formula (II)), or a pharmaceutically acceptable salt, isotope, N-oxide, solvate or stereoisomer thereof.
- a further embodiment of the present invention is directed to a method for treating, ameliorating and/or preventing neuropathic pain.
- a neuropathic pain include pain due to a disease, condition, disorder, or pain state including cancer, neurological disorders, spine and peripheral nerve surgery, brain tumor, traumatic brain injury (TBI), spinal cord trauma, chronic pain syndrome, fibromyalgia, chronic fatigue syndrome, lupus, sarcoidosis, peripheral neuropathy, bilateral peripheral neuropathy, diabetic neuropathy, central pain, neuropathies associated with spinal cord injury, stroke, amyotrophic lateral sclerosis (ALS), Parkinson's disease, multiple sclerosis, sciatic neuritis, mandibular joint neuralgia, peripheral neuritis, polyneuritis, stump pain, phantom limb pain, bony fractures, oral neuropathic pain, Charcot's pain, complex regional pain syndrome I and II (CRPS I/II), radiculopathy, Guillain-Barre syndrome, meralgia paresthetica,
- neuropathic cold allodynia which can be characterized by the presence of a neuropathy-associated allodynic state in which a hypersensitivity to cooling stimuli exists.
- neuropathic cold allodynia include allodynia due to a disease, condition, disorder or pain state including neuropathic pain (neuralgia), pain arising from spine and peripheral nerve surgery or trauma, traumatic brain injury (TBI), trigeminal neuralgia, postherpetic neuralgia, causalgia, peripheral neuropathy, diabetic neuropathy, central pain, stroke, peripheral neuritis, polyneuritis, complex regional pain syndrome I and II (CRPS I/II) and radiculopathy.
- neuropathic pain neuralgia
- TBI traumatic brain injury
- trigeminal neuralgia postherpetic neuralgia
- causalgia peripheral neuropathy
- diabetic neuropathy central pain
- stroke peripheral neuritis
- polyneuritis complex regional pain syndrome I and II (CRPS I/II
- the present invention is directed to a method for treating, ameliorating and/or preventing neuropathic cold allodynia in which a hypersensitivity to a cooling stimuli exists, comprising administering to a subject in need of such treatment a therapeutically effective amount of a compound of Formula (I) (as well as compounds of Formula (II)) or a pharmaceutically acceptable salt, isotope, N-oxide, solvate or stereoisomer thereof.
- Examples of psychiatric disorders include, but are not limited to, anxieties such as, social anxiety, post-traumatic stress disorder, phobias, social phobia, special phobias, panic disorder, obsessive-compulsive disorder, acute stress disorder, separation anxiety disorder, and generalized anxiety disorder, as well as depression such as, major depression, bipolar disorder, seasonal affective disorder, post-natal depression, manic depression, and bipolar depression, mood disorders and mood affective disorders that can be treated according to the present invention include, but are not limited to, bipolar disorder I depressed, hypomanic, manic and mixed form; bipolar disorder II; depressive disorders, such as single depressive episode or recurrent major depressive disorder, minor depressive disorder, treatment-resistant depression, anxious depression, bipolar disorder, depressive disorder with postpartum onset, depressive disorders with psychotic symptoms; persistent mood disorders, such as cyclothymia, dysthymia, euthymia; and premenstrual dysphoric disorder; psychoses.
- anxieties such
- neurological disorder examples include, but are not limited to, tremors, dyskinesias, dystonias, spasticity, Tourette's Syndrome; neuromyelitis optica, Parkinson's disease; Alzheimer's disease; senile dementia; Huntington's disease; Epilepsy/seizure disorders and sleep disorders.
- cancers include, but are not limited to, benign skin tumors, prostate tumors, ovarian tumors and cerebral tumors (glioblastomas, medulloepitheliomas, medulloblastomas, neuroblastomas, tumors of embryonic origin, astrocytomas, astroblastomas, ependymomas, oligodendrogliomas, neuroepitheliomas, epiphyseal tumor, ependymoblastomas, malignant meningiomas, sarcomatosis, malignant melanomas, schwannomas).
- eye conditions include, but are not limited to, ocular hypertension, glaucoma, degeneration and apoptosis of retinal ganglion cells and neuroretinal cells.
- inventions of this invention provide for a method for modulating MGL receptor activity, including when such receptor is in a subject, comprising exposing MGL receptor to a therapeutically effective amount of at least one compound selected from compounds of the invention.
- Embodiments of this invention are compounds of Formula (I),
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R a is H, halo, C 1-4 alkyl, or OC 1-4 alkyl; and R a1 is C 1-4 alkyl, OC 1-4 alkyl, OC 1-4 haloalkyl, or (C ⁇ O)NHCH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R a is H, halo, C 1-4 alkyl, OC 1-4 alkyl, or C 1-4 haloalkyl; and R a1 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R a1 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R a is H, Cl, F, CH 3 , CF 3 , or OCH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R b is H or CH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R c is H or CF 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R d is H, Cl, or F.
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R a is H, Cl, Br, F, or OCH 3
- R a1 is OCH 3 or
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is:
- R e is independently selected from the group consisting of: H, halo, C 1-4 akyl, C 1-4 haloalkyl, OC 1-4 alkyl, and cyclopropyl.
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is:
- R f is selected from the group consisting of: H, C 1-4 alkyl, CH 2 CH 2 OH, CH 2 CF 3 , cyclopropyl, phenyl, and phenyl substituted with CF 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R g is H, OCH 3 or CF 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R a is independently selected from the group consisting of: H, Cl, F, C 1-4 alkyl, OC 1-4 alkyl, and C 1-4 haloalkyl; and R b is CH 3 or CH(CH 3 ) 2 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 3 is
- An additional embodiment of the invention is a compound of Formula (I) wherein R 3 is cyclopropyl and R 4 is CH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 3 is 5-(trifluoromethyl)-2-thienyl or 1-methylindol-2-yl; and R 4 is CH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 3 is 3-chlorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,4-difluorophenyl, and 4-chloro-3-fluorophenyl.
- An additional embodiment of the invention is a compound of Formula (I) wherein R 4 is CH 3 .
- An additional embodiment of the invention is a compound of Formula (I) wherein R 4 is cyclopropyl.
- An additional embodiment of the invention is a compound of Formula (I) wherein R 2 is
- R a is F, Cl, or OCH 3
- R a1 is OCH 3 , CH 3 , or 2H-1,2,3-triazol-2-yl and R 4 is CH 3 .
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (IA):
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (IB):
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (IC):
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (IC), wherein R 2 is:
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (IC), wherein R 2 is:
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (ID):
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (ID), wherein R 3 is:
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (ID), wherein Ring A is:
- An additional embodiment of the invention is a compound of Formula (I) having the Formula (ID), wherein Ring A is:
- An additional embodiment of the invention is a compound selected from the group consisting of compounds of Formula (I), Formula (IA), Formula (IB), Formula (IC), Formula (ID), and a combination thereof.
- a further embodiment of the current invention is a compound as shown below in Table 1.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising: (A) a therapeutically effective amount of at least one compound selected from compounds of Formula (I):
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula (IA), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (IA), pharmaceutically acceptable prodrugs of compounds of Formula (IA), and pharmaceutically active metabolites of Formula (IA); and at least one pharmaceutically acceptable excipient.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula (IB), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (IB), pharmaceutically acceptable prodrugs of compounds of Formula (IB), and pharmaceutically active metabolites of Formula (IB); and at least one pharmaceutically acceptable excipient.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula (IC), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (IC), pharmaceutically acceptable prodrugs of compounds of Formula (IC), and pharmaceutically active metabolites of Formula (IB); and at least one pharmaceutically acceptable excipient.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound of Formula (ID), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (ID), pharmaceutically acceptable prodrugs of compounds of Formula (ID), and pharmaceutically active metabolites of Formula (ID); and at least one pharmaceutically acceptable excipient.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound in Table 1 (as well as Table 2), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Table 1 (as well as Table 2), pharmaceutically acceptable prodrugs of compounds of Table 1, and pharmaceutically active metabolites of Table 1 (as well as Table 2); and at least one pharmaceutically acceptable excipient.
- enantiomers and diastereomers of the compounds of Formula (I) are also within the scope of the invention.
- pharmaceutically acceptable salts, N-oxides or solvates of the compounds of Formula (I) are also within the scope of the invention.
- pharmaceutically acceptable prodrugs of compounds of Formula (I) are also within the scope of the invention.
- pharmaceutically active metabolites of the compounds of Formula (I) are also within the scope of the invention.
- isotopic variations of compounds of Formula (I) (as well as Formulas (IA), (IB), (IC) and (ID)), such as, e.g., deuterated compounds of Formula (I).
- pharmaceutically acceptable salts, N-oxides or solvates of the isotopic variations of the compounds of Formula (I) (as well as Formulas (IA), (IB), (IC) and (ID)).
- compositions of Formula (I) are also within the scope of the invention.
- pharmaceutically acceptable prodrugs of the isotopic variations of the compounds of Formula (I) as well as Formulas (IA), (IB), (IC) and (ID)
- pharmaceutically active metabolites of the isotopic variations of the compounds of Formula (I) as well as Formulas (IA), (IB), (IC) and (ID)
- pharmaceutically active metabolites of the isotopic variations of the compounds of Formula (I) are also as Formulas (IA), (IB), (IC) and (ID)).
- An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or condition mediated by MGL receptor activity, comprising administering to a subject in need of such treatment a therapeutically effective amount of at least one compound selected from compounds of Formula (I):
- An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or condition mediated by MGL receptor activity, comprising administering to a subject in need of such treatment a therapeutically effective amount of at least one compound selected from compounds of Formula (I) (as well as Formulas (IA), (IB), (IC) and (ID)), enantiomers and diastereomers of the compounds of Formula (I), isotopic variations of the compounds of Formula (I), and pharmaceutically acceptable salts of all of the foregoing.
- Embodiments of this invention are compounds of Formula (II),
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 5 is
- An additional embodiment of the invention is a compound of Formula (II) wherein R 6 is
- a further embodiment of the current invention is a compound as shown below in Table 3.
- An additional embodiment of the invention is a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of at least one compound in Table 3, as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Table 3, pharmaceutically acceptable prodrugs of compounds of Table 3, and pharmaceutically active metabolites of Table 3; and at least one pharmaceutically acceptable excipient.
- An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or condition mediated by MGL receptor activity, comprising administering to a subject in need of such treatment a therapeutically effective amount of at least one compound selected from compounds of Formula (II):
- 3-iodobenzoic acid is reacted with 3-(trifluoromethyl)pyrazole, a base such as cesium carbonate, a copper catalyst such as CuI, a ligand such as trans-N,N′-dimethylcyclohexane-1,2-diamine, in a suitable solvent such as DMF, at temperatures ranging from 100-140° C., under microwave irradiation, to provide 3-[3-(trifluoromethyl)pyrazol-1-yl]benzoic acid.
- a base such as cesium carbonate
- a copper catalyst such as CuI
- a ligand such as trans-N,N′-dimethylcyclohexane-1,2-diamine
- Amino intermediate compound of formula (VI) is subsequently cyclized with triphosgene to yield ethyl 5-oxo-1-aryl-1H-1,2,4-triazole3-carboxylate of formula (VII).
- the aryl ether of formula (VIII) is synthesized by treatment of 1,2,4-triazolone of formula (VII) with alkyl oxonium salts, such as trimethyloxonium tetrafluoroborate or triethyloxonium tetrafluoroborate; in a suitable solvent such as dichloromethane (DCM), and the like, at temperatures ranging from 0° C. to room temperature.
- alkyl oxonium salts such as trimethyloxonium tetrafluoroborate or triethyloxonium tetrafluoroborate
- triazoles of formula (Xa) and (Xb) are prepared in a [3+2] cycloaddition reaction between a azidomethylbenzene and 4,4,4-trifluoro-2-butynoic acid ester; in a suitable solvent such as toluene, and the like; at a temperature of about 115° C.; for a period of 16 to 24 h; to provide a mixture of isomeric triazole compounds.
- Hydrolysis of the ester moiety in compounds of formula (Xa) and (Xb) is achieved employing conditions previously described.
- Decarboxylation is achieved employing silver carbonate; in a suitable solvent such as dimethyl sulfoxide (DMSO), and the like; in the presence of acetic acid: at a temperature of 120° C.; for a period of 18 h; to provide compounds of formula (XIa) and (XIb), where PG is benzyl.
- Cleavage of the benzyl protecting group of compounds of formula (XIa) and (XIb) is achieved according to procedures known to one skilled in the art and employing established methodologies, such as those described in T. W. Greene and P. G. M.
- a compound of formula (XII) where R b is H is reacted in a metal-mediated cross coupling reaction; with a suitably substituted cycloalkyl boronic acid, boronic ester, and the like; a copper catalyst such as Cu(OAc) 2 , a ligand such as 2,2′-bipyridine, and the like; a base such as K 2 CO 3 , Cs 2 CO 3 , lithium bis(trimethylsilyl)amide (LHMDS), sodium tert-butoxide (NaOtBu), K 3 PO 4 , and the like; in a suitable solvent such as toluene, THF, DMF, dioxane, 1,2-dichloroethane, or a mixture thereof; provide a mixture of isomeric compounds ethyl 1-cyclopropyl-5-methyl-1H-pyrazole-4-carboxylate and ethyl 1-cyclopropyl-3-methyl-1H-pyrazole
- a compound of formula (XII), where R b is CH 3 , is fluorinated using an electrophilic fluorine source such as, N-fluorobenzenesulfonimide (NFSI), a base such as lithium diisopropylamide (LDA); in a suitable solvent such as THF, and the like; at temperatures ranging from ⁇ 78° C. to rt; for a period of 18-24 h; to provide ethyl 3-fluoro-1,5-dimethyl-1H-pyrazole-4-carboxylate.
- an electrophilic fluorine source such as, N-fluorobenzenesulfonimide (NFSI), a base such as lithium diisopropylamide (LDA); in a suitable solvent such as THF, and the like; at temperatures ranging from ⁇ 78° C. to rt; for a period of 18-24 h; to provide ethyl 3-fluoro-1,5-dimethyl-1H-pyrazo
- a compound of formula (XIV) undergoes a palladium-catalyzed cyanation employing conditions known to one skilled in the art.
- a compound of formula (XIV) is reacted with a palladium catalyst such as tetrakis(triphenylphosphine)palladium(0), and the like; zinc cyanide as the nucleophile; in a suitable solvent such as N,N-dimethylformamide (DMF), and the like; at a temperature of about 80° C.; for a period of 18-24 h; to provide a cyano compound.
- a palladium catalyst such as tetrakis(triphenylphosphine)palladium(0), and the like
- zinc cyanide as the nucleophile
- a suitable solvent such as N,N-dimethylformamide (DMF), and the like
- DMF N,N-dimethylformamide
- Reduction of the nitro group is achieved employing iron in acetic acid to
- the aryl amine compound of formula (XV) undergoes a two-step diazotization-iodination reaction employing conditions known to one skilled in the art.
- diazotization of the aryl amine is achieved using hydrochloric or sulfuric acid in the presence of sodium nitrite; subsequent iodination reaction with KI affords an iodo compound.
- a nitrile compound of formula (XVI) is hydrolyzed with a base such as sodium hydroxide, potassium hydroxide, and the like; in suitable solvent such as 1,4-dioxane and water; to provide a compound of formula (XVIII), where X is CH or N (wherein only one X can be N); HET 1 is a 5 membered heteroaryl containing 2 or 3 nitrogen members, and R a is H, halo, C 1-4 alkyl, C 1-4 haloalkyl, and OC 1-4 alkyl.
- a compound of formula (XV) is reacted with diformylhydrazine; in the presence of trimethylsilyl chloride as a Lewis acid; a base such as triethylamine; in a suitable solvent such as pyridine; at a temperature of about 100° C.; for a period of about 16 h; provides the 1,2,4-triazol-4-yl intermediate compound.
- a compound of formula (XVIII), where X is CH, HET 1 is 1,2,4-triazol-4-yl, is prepared in two steps from a compound of formula (XX) where R a is halo or C 1-4 alkyl.
- a compound of formula (XX) where R a is halo or C 1-4 alkyl is reacted with diformylhydrazine, in the presence of trimethylsilyl chloride as a Lewis acid, triethylamine, in a suitable solvent such as pyridine, at a temperature of about 100° C., for a period of about 16 h, to provide the 1,2,4-triazol-4-yl intermediate; in a second step, saponification is achieved according to conditions known to one skilled in the art, or as previously described.
- methyl 4-aminopyridine-2-carboxylate and methyl 5-aminonicotinate may be used instead a compound of formula (XX), to provide compounds of formula (XVIII), where only one X is N.
- 1-aminopyridin-1-ium is reacted in a 1,3-dipolar addition reaction with a compound of formula (XXII), where R a is H, C 1-4 alkyl or C 1-4 haloalkyl; in the presence of a base such as TEA, and the like; 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ); in a suitable solvent such as DMF, and the like; at temperatures ranging from 0° C. to rt; for a period of 16-24 h; provides a compound of formula (XXIII). Hydrolysis of the ester to the corresponding acid is achieved according to procedures previously described.
- compounds of formulas (XXVIa, XXVIb, and XXVIc) are prepared under conditions known to one skilled in the art, by condensation of commercially available or synthetically accessible substituted pyridine, pyridazine and pyrazine amines of formulas (XXVa, XXVb, and XXVc) where R a is as defined in claim 1 , using ethyl 2-chloro-3-oxobutanoate in a suitable solvent such as 1,2-dimethoxy ethane (DME), and the like; at temperature of 90° C., for a period of about 2-16 hours.
- DME 1,2-dimethoxy ethane
- Saponification of the esters (XXVIa, XXVIb, and XXVIc) to the corresponding acid is achieved employing conditions known to one skilled in the art.
- a suitable base such as potassium trimethylsilanolate (TMSOK), NaOH, LiOH, and the like
- TMSOK potassium trimethylsilanolate
- NaOH NaOH
- LiOH LiOH
- a suitable solvent such as water/THF/MeOH
- 2-methylquinoxaline-6-carboxylic acid (where R b is H) is prepared by condensation of commercially available or synthetically accessible 2-amino-4-aminobenzoic acid with 1,2-dioxoalkanes such as 2-oxopropanal, and the like; in a suitable solvent such as EtOH and the like, at a temperature of 80° C., for a period of about 16-24 hours, to provide 2-methylquinoxaline-6-carboxylic acid.
- methyl 3,4-diaminobenzoate (where R b is CH 3 ) is condensed with diethyl oxalate, in a suitable solvent such as EtOH and the like; at a temperature of about 140° C.; for a period of about 16-24 hours; affords methyl 2,3-dihydroxyquinoxaline-6-carboxylate.
- chlorinating reagent such as thionyl chloride, and the like
- neat, or in a suitable solvent such as toluene, and the like
- catalytic amount of DMF at reflux temperature; affords methyl 2,3-dichloroquinoxaline-6-carboxylate.
- Saponification of the ester to the corresponding acid is achieved employing conditions known to one skilled in the art, for example, using a suitable base such as NaOH, LiOH, KOH, and the like, preferably Li; in a suitable solvent such as water/THF/MeOH, at room temperature, for a period of about 1 h, affords quinoxaline-6-carboxylic-2,3-d2 acid (where M is Li). Potassium, sodium and lithium salts are isolated depending on the base used in the saponification.
- a suitable base such as NaOH, LiOH, KOH, and the like, preferably Li
- a suitable solvent such as water/THF/MeOH
- 6,6-dimethylmorpholine-3-carboxylic acid is prepared in two steps from 4-(tert-butyl) 3-methyl 6,6-dimethylmorpholine-3,4-dicarboxylate.
- deprotection of BOC group is achieved according to procedures known to one skilled in the art and employing established methodologies, such as those described in T. W. Greene and P. G. M. Wuts, “Protective Groups in Organic Synthesis,” 3 ed., John Wiley & Sons, 1999, pgs 518-525.
- deprotection under acidic conditions such as trifluoroacetic acid (TFA)/CH 2 Cl 2 , HCl/Dioxane, and the like, at room temperature for a period of 2 h.
- acidic conditions such as trifluoroacetic acid (TFA)/CH 2 Cl 2 , HCl/Dioxane, and the like
- suitable base such as NaOH and the like
- MeOH/water a solvent
- Diazotization of 6,6-dimethylmorpholine-3-carboxylic acid is achieved employing sodium nitrite; in water; under acidic conditions such as conc. HCl; at temperatures ranging from 0° C. to room temperature; for a period of 16 h.
- TFAA trifluoroacetic anhydride
- ACN acetonitrile
- a suitable base such as NaOH, LiOH, KOH, and the like
- a suitable solvent such as water, THF, MeOH, or a mixture thereof; at a temperature of about 60° C.; for a period of about 24 h; to provide compounds of formulas (XLIIIa) and (XLIIIb), where M is K, Na, or Li.
- a suitable solvent such as diethyl ether, tetrahydrofuran, dioxane, water, or a mixture thereof
- a second step reduction of the aforementioned mercurial chloride complex is accomplished by reaction with 3 M sodium hydroxide, and a reducing agent such as sodium borohydride, at a temperature of about 0° C., to provide the cyclized (1S,2S,5R)-9-((R)-1-phenylethyl)-9-azabicyclo[3.3.1]nonan-2-ol product.
- a reducing agent such as sodium borohydride
- a compound of formula (XXVIII) is converted to compound of formula (XXIX) under oxidative conditions, such as Swern (Moffott-Swern) oxidation.
- oxidative conditions such as Swern (Moffott-Swern) oxidation.
- a compound of formula (XXVIII) is treated with DMSO, oxalyl chloride, triethylamine, in a suitable solvent such as DCM, and the like, to provide a compound of formula (XXIX).
- the reaction is run initially at ⁇ 78° C. and then warmed to room temperature and stirred overnight.
- a compound of formula (XXIX) is converted to compound (XXX) by treatment with a strong base such as lithium bis(trimethylsilyl)amide (LiHMDS/LHMDS), and the like, in a suitable solvent such as THF, and the like, at a temperature of about ⁇ 78° C., for a period of about 30 minutes.
- a strong base such as lithium bis(trimethylsilyl)amide (LiHMDS/LHMDS), and the like
- a suitable solvent such as THF, and the like
- the resulting lithium enolate is trapped by methyl or ethyl cyanoformate, at a temperature of about ⁇ 78° C., for a period of 1-3 h, to furnish the 0-keto ester compound of formula (XXX), where PG is BOC and R b is C 1-4 alkyl.
- a keto-ester compound of formula (XXX) is reacted with a commercially available or synthetically accessible hydrazine of formula R 4a NHNH 2 , in an inert solvent such as toluene, and the like, at a temperature of about 100° C., to provide a pyrazolone compound of formula (XXXI), where R 4a is C 1-4 alkyl or C 3-6 cycloalkyl.
- pyrazolone compound of formula (XXXI), with a sulfonate-based leaving group such as trifluoromethanesulfonyl (triflate) is achieved by is by reaction with a triflating agent such as trifluoromethanesulfonic anhydride (Tf 2 O), a base such as triethylamine (TEA), pyridine, and the like, in a suitable solvent such as DCM and the like.
- Milder triflating agents such as N-phenylbis(trifluoromethanesulfonimide) (Tf 2 NPh), a base such as TEA, DIEA, and the like, in a suitable solvent such as DCM, and the like; are used for better selectivity, to provide a compound of formula (XXXII).
- racemic-(5R,8S)-2-Methyl-3-phenyl-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole is prepared according to methods analogous to those described above.
- a compound of formula (XXXII) is reacted in a metal mediated cross coupling reaction to provide a compound of formula (XXXIII), where R 4a is H or C 1-4 alkyl, PG is BOC, and R 3 is phenyl optionally substituted with one, two or three members independently selected from the group consisting of: halo, or C 1-4 haloalkyl; or thiophene substituted with CF 3 .
- a compound of formula (XXXII), where R 4a is H or C 1-4 alkyl, and PG; is reacted with a suitably substituted commercially available or synthetically accessible alkyl, cycloalkyl, aryl or heteroaryl boronic acid, boronate ester, and the like, in the presence of a palladium catalyst such as [1,1′-bis(di-tert-butylphosphino)ferrocene] dichloropalladium(II) (PdCl 2 (dtbpf)), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl 2 (dppf)), palladium(II)bis(triphenylphosphine) dichloride (Pd(PPh 3 ) 2 Cl
- tert-butyl (5R,9S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate is reacted in a metal mediated coupling reaction with a commercially available or synthetically accessible aryl or heteroaryl boronic acid, boronate ester, of formula R 3 —B(OH) 2 , where R 3 is phenyl optionally substituted with one, two or three members independently selected from the group consisting of: halo, C 1-4 haloalkyl, OC 1-4 alkyl; or 1-methyl-1H-indol-2-yl; employing a catalyst such as chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(
- a compound of Formula (IB) is prepared by conventional amide bond forming techniques such as coupling reactions which are well known to those skilled in the art (such as HATU (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate), BOP (benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate), or conversion of the acid to an acid chloride).
- coupling reactions such as HATU (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate), BOP (benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate), or conversion of the acid to an acid chloride).
- Coupling reactions are conducted in a suitable solvent such as DCM, THF, DMF and the like, optionally in the presence of a tertiary amine such as N-methylmorpholine, N-ethyldiisopropylamine (DIEA, DIPEA), or triethylamine (TEA), at a temperature ranging from about 0° C. to rt, to provide compound a of Formula (IB).
- a suitable solvent such as DCM, THF, DMF and the like
- a tertiary amine such as N-methylmorpholine, N-ethyldiisopropylamine (DIEA, DIPEA), or triethylamine (TEA)
- a compound of Formula (IB) (as well as a compound of Formula (I)), where R 2 is a heteroaryl substituted with a reactive functional group such as a hydroxyl group, is alkylated with a suitable alkyl halide such as 1-iodoethane, fluoro-2-iodoethane, and the like.
- a compound of Formula (IB) (as well as a compound of Formula (I)), where R 2 is 4-hydroxyquinoline, is reacted with fluoro-2-iodoethane; a suitable base such as Cs 2 CO 3 , K 2 CO 3 , and the like: in a suitable solvent such as N,N-dimethylformamide to provide a compound of Formula (IA) (as well as a compound of Formula (I)) where R 2 is 4-(2-fluoroethoxy)quinoline.
- a compound of Formula (IB) (as well as a compound of Formula (I)), where R 2 is quinoline, is oxidized to the N-oxide compound of Formula (IB) (as well as a compound of Formula (I)), employing m-chloroperoxybenzoic acid (m-CPBA), in a suitable solvent such as DCM, chloroform, and the like, at temperatures ranging from 0° C. to room temperature, for a period of 30 minutes to 1 hr.
- m-CPBA m-chloroperoxybenzoic acid
- a compound of Formula (IB) (as well as a compound of Formula (I)), where R 2 is a bromo substituted quinoline is tritiated employing conditions known to one skilled in the art.
- (4-bromoquinolin-6-yl)((5R,9S)-3-(3,5-difluorophenyl)-2-methyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazol-10-yl)methanone is reacted with Pd/C, in a suitable solvent such as MeOH, and the like, in the presence of 1 atm of tritium gas, to provide ((5R,9S)-3-(3,5-difluorophenyl)-2-methyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazol-10-yl)(quinolin-6-yl-4
- a compound of Formula (IB) (as well as a compound of Formula (I)), where R 2 is a heteroaryl substituted with a reactive functional group such as Br, is reacted under catalytic hydrogenation dehalogenation reaction conditions such as Pd/C and hydrogen gas under conditions known to one skilled in the art.
- a compound of Formula (I) is prepared from a compound of formula (XXXV) in three steps. In a first step, deprotection of the BOC protecting group as previously described, followed by amide bond coupling then subsequent Suzuki coupling as previously described provides a compound of Formula (I).
- a compound of formula (XXXVIII) is prepared in a manner as described in JOC 2002, 67, 3479-3486, where PG is BOC.
- a keto-ester compound of formula (XXXVIII) is reacted with a commercially available or synthetically accessible methylhydrazine, in an inert solvent such as toluene, and the like, at a temperature of about 100° C., to provide a compound of formula (XXXIX), where PG is Boc.
- a compound of formula (XXIX), with a sulfonate-based leaving group such as trifluoromethanesulfonyl (triflate) is achieved by is by reaction with a triflating agent such as trifluoromethanesulfonic anhydride (Tf 2 O), a base such as triethylamine (TEA), pyridine, and the like, in a suitable solvent such as DCM and the like.
- a triflating agent such as trifluoromethanesulfonic anhydride (Tf 2 O)
- Tf 2 O trifluoromethanesulfonic anhydride
- Tf 2 O trifluoromethanesulfonic anhydride
- Tf 2 O trifluoromethanesulfonic anhydride
- Tf 2 O trifluoromethanesulfonic anhydride
- Tf 2 O trifluoromethanesulfonic anhydride
- Tf 2 O trifluoromethanesulfonic an
- Milder triflating agents such as N-phenylbis(trifluoromethanesulfonimide) (Tf 2 NPh), a base such as TEA, DIEA, and the like, in a suitable solvent such as DCM, and the like; are used for better selectivity, to provide a compound of formula (XLa) and (XLb), where PG is BOC.
- Tf 2 NPh N-phenylbis(trifluoromethanesulfonimide)
- a base such as TEA, DIEA, and the like
- suitable solvent such as DCM, and the like
- a single enantiomer compound of formula (XLa) (as well as XLb, or the racemic mixture), is reacted in a coupling reaction with a suitably substituted commercially available or synthetically accessible alkyl, cycloalkyl, aryl or heteroaryl boronic acid, boronate ester, and the like, in the presence of a palladium catalyst, under Suzuki coupling conditions previously described to provide a compound of formula (XLI). Deprotection of the protecting group is achieved according to methods previously described. Subsequent amide coupling of a compound of formula (XLII), with a suitably substituted commercially available or synthetically accessible acid, provides a compound of Formula (II).
- Compounds of Formula (I) may be converted to their corresponding salts using methods known to one of ordinary skill in the art.
- an amine of Formula (I) is treated with trifluoroacetic acid, HCl, or citric acid in a solvent such as Et 2 O, CH 2 Cl 2 , THF, MeOH, chloroform, or isopropanol to provide the corresponding salt form.
- trifluoroacetic acid or formic acid salts are obtained as a result of reverse phase HPLC purification conditions.
- Crystalline forms of pharmaceutically acceptable salts of compounds of Formula (I) may be obtained in crystalline form by recrystallization from polar solvents (including mixtures of polar solvents and aqueous mixtures of polar solvents) or from non-polar solvents (including mixtures of non-polar solvents).
- the compounds according to this invention may accordingly exist as enantiomers. Where the compounds possess two or more chiral centers, they may additionally exist as diastereomers. It is to be understood that all such isomers and mixtures thereof are encompassed within the scope of the present invention.
- Compounds prepared according to the schemes described above may be obtained as single forms, such as single enantiomers, by form-specific synthesis, or by resolution. Compounds prepared according to the schemes above may alternately be obtained as mixtures of various forms, such as racemic (1:1) or non-racemic (not 1:1) mixtures. Where racemic and non-racemic mixtures of enantiomers are obtained, single enantiomers may be isolated using conventional separation methods known to one of ordinary skill in the art, such as chiral chromatography, recrystallization, diastereomeric salt formation, derivatization into diastereomeric adducts, biotransformation, or enzymatic transformation. Where regioisomeric or diastereomeric mixtures are obtained, as applicable, single isomers may be separated using conventional methods such as chromatography or crystallization.
- reaction mixtures were magnetically stirred at room temperature (rt) under a nitrogen atmosphere. Where solutions were “dried,” they were generally dried over a drying agent such as Na 2 SO 4 or MgSO 4 . Where mixtures, solutions, and extracts were “concentrated”, they were typically concentrated on a rotary evaporator under reduced pressure.
- Mass spectra were obtained on an Agilent series 1100 MSD using electrospray ionization (ESI) in positive mode unless otherwise indicated. Calculated (calcd.) mass corresponds to the exact mass.
- NMR Nuclear magnetic resonance
- Step A racemic-tert-Butyl (5R,9S)-2-methyl-3-oxo-2,3,4,5,6,7,8,9-octahydro-1H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- Step B racemic-tert-Butyl (5R,9S)-2-methyl-3-(((trifluoromethyl)sulfonyl) oxy)-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- Step C racemic-tert-Butyl (5R,9S)-2-methyl-3-phenyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- Step D racemic-(5R,9S)-2-Methyl-3-phenyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole
- Step B (1S,8S,Z)-8-(((R)-1-Phenylethyl)amino)cyclooct-4-en-1-ol
- Step D tert-Butyl (1 S,2S,5R)-2-hydroxy-9-azabicyclo[3.3.1]nonane-9-carboxylate
- Step E tert-Butyl (1R,5R)-2-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate
- Triethylamine (TEA)(85 mL, 61 mmol) was added and the reaction was allowed to warm to room temperature and stirred for 2 h.
- the reaction mixture was washed with water (3 ⁇ 300 mL), dried over sodium sulfate, filtered and evaporated.
- the residue was purified by silica gel column chromatography eluting with heptane:ethyl acetate (4:1) to afford the title compound (19.5 g, 82 mmol, 80% yield) as a white crystalline solid. [ ⁇ ] D 25 +116.0° (c 0.110, MeOH). MS (ESI): mass calcd.
- Step F 9-(tert-Butyl) 3-ethyl (1S,5R)-2-oxo-9-azabicyclo[3.3.1]nonane-3,9-dicarboxylate
- Step G tert-Butyl (5R,9S)-2-methyl-3-oxo-2,3,4,5,6,7,8,9-octahydro-1H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- Step H tert-Butyl (5R,9S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- the reaction mixture was washed with saturated sodium bicarbonate (2 ⁇ 200 mL), 10% potassium bisulfate (2 ⁇ 200 mL) and brine (1 ⁇ 200 mL), dried over sodium sulfate, filtered and evaporated.
- the residue was purified by gradient silica column chromatography eluting with heptane:ethyl acetate (6:1 ⁇ 4:1). The residue was dissolved in ethyl acetate (100 mL) and evaporated. The less pure fractions were combined and evaporated. The residue was dissolved in dichloromethane (100 mL), washed with saturated sodium bicarbonate (3 ⁇ 150 mL), dried over sodium sulfate, filtered and evaporated.
- Step A tert-Butyl (5R,9S)-3-(3,5-difluorophenyl)-2-methyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole-10-carboxylate
- Step B (5R,9S)-3-(3,5-Difluorophenyl)-2-methyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazole
- Step A racemic-tert-Butyl (5R,8 S)-2-methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate
- Step B racemic-(5R,8S)-2-Methyl-3-phenyl-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole
- Step B Ethyl (E)-5-(3-ethoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-2-carboxylate
- Step C Ethyl 5-(3-ethoxy-3-oxopropyl)pyrrolidine-2-carboxylate
- Step D 1-(tert-Butyl) 2-ethyl 5-(3-ethoxy-3-oxopropyl)pyrrolidine-1,2-dicarboxylate
- Step E 8-(tert-Butyl) 3-ethyl 2-oxo-8-azabicyclo[3.2.1]octane-3,8-dicarboxylate
- Step F racemic-tert-Butyl 2-methyl-3-oxo-1,2,3,4,5,6,7,8-octahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate
- Step G tert-butyl (5R,8S)-2-Methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate and tert-butyl (5S,8R)-2-Methyl-3-(((trifluoromethyl)sulfonyl)oxy)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate
- Step A Methyl 1-(3-chlorophenyl)-1,2,4-triazole-3-carboxylate
- Step B 1-(3-Chlorophenyl)-1,2,4-triazole-3-carboxylic Acid
- Step B Ethyl 5-oxo-1-phenyl-4H-1,2,4-triazole-3-carboxylate
- Step C Ethyl 5-methoxy-1-phenyl-1,2,4-triazole-3-carboxylate
- Step A Ethyl 3-benzyl-5-(trifluoromethyl)triazole-4-carboxylate and ethyl 1-benzyl-5-(trifluoromethyl)triazole-4-carboxylate
- Step B 3-Benzyl-5-(trifluoromethyl)triazole-4-carboxylic Acid and 1-benzyl-5-(trifluoromethyl)triazole-4-carboxylic Acid
- Step C 1-Benzyl-4-(trifluoromethyl)triazole and 1-benzyl-5-(trifluoromethyl)triazole
- Step B 3-Fluoro-5-(1,2,4-triazol-4-yl)benzoic Acid
- Step B 4-Pyrazol-1-ylpyridine-3-carboxylic Acid
- Step D 6-Methyl-3-(1,2,4-triazol-1-yl)pyridine-2-carbonitrile
- Step E 6-Methyl-3-(1,2,4-triazol-1-yl)pyridine-2-carboxylic Acid
- Step B 6-Methyl-4-(1,2,4-triazol-4-yl)pyridine-2-carbonitrile
- Step A 5-(Triazol-2-yl)pyridine-3-carboxylic acid and 5-(triazol-1-yl)pyridine-3-carboxylic Acid
- Step B Methyl 5-(triazol-2-yl)pyridine-3-carboxylate and Methyl 5-(triazol-1-yl)pyridine-3-carboxylate
- Step A Ethyl 1-cyclopropyl-5-methyl-pyrazole-4-carboxylate and ethyl 2-cyclopropyl-5-methyl-pyrazole-4-carboxylate
- Step A Ethyl 2,7-dimethylimidazo[1,2-b] pyridazine-3-carboxylate
- Step B Potassium 2,7-dimethylimidazo[1,2-b]pyridazine-3-carboxylate
- Step A Ethyl 2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-3-carboxylate
- Step B Methyl 2,3-dichloroquinoxaline-6-carboxylate
- Step D Lithium quinoxaline-6-carboxylate-2,3-d2
- Step B 6,6-Dimethyl-6,7-dihydro-4H-[1,2,3] oxadiazolo[4,3-c][1,4]oxazin-8-ium-3-olate
- Step C Ethyl 2,6,6-trimethyl-6,7-dihydro-4H-pyrazolo[5,1-c] [1,4] oxazine-3-carboxylate
- Step D Potassium 2,6,6-trimethyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine-3-carboxylate
- Step A tert-Butyl (5R,8S)-2-methyl-3-(3,4,5-trifluorophenyl)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole-9-carboxylate
- Step B (5R,8S)-2-Methyl-3-(3,4,5-trifluorophenyl)-2,4,5,6,7,8-hexahydro-5,8-epiminocyclohepta[c]pyrazole 2,2,2-trifluoroacetate
- Example 1 racemic-((5R,9S)-2-Methyl-3-phenyl-4,5,6,7,8,9-hexahydro-2H-5,9-epiminocycloocta[c]pyrazol-10-yl) (quinolin-6-yl)methanone
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US4812462A (en) | 1986-04-01 | 1989-03-14 | Warner-Lambert Company | 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid analogs having antihypertensive activity |
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2019
- 2019-09-27 EP EP19780428.9A patent/EP3856179A1/fr active Pending
- 2019-09-27 CA CA3111309A patent/CA3111309A1/fr active Pending
- 2019-09-27 MX MX2021003661A patent/MX2021003661A/es unknown
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- 2019-09-27 JP JP2021517338A patent/JP7413368B2/ja active Active
- 2019-09-27 CN CN201980078966.8A patent/CN113164458A/zh active Pending
- 2019-09-27 AU AU2019349962A patent/AU2019349962A1/en active Pending
- 2019-09-27 MA MA053722A patent/MA53722A/fr unknown
- 2019-09-27 BR BR112021005936-9A patent/BR112021005936A2/pt unknown
- 2019-09-27 US US16/586,263 patent/US20200102311A1/en not_active Abandoned
- 2019-09-27 KR KR1020217012861A patent/KR20210069079A/ko unknown
- 2019-09-27 WO PCT/IB2019/058241 patent/WO2020065614A1/fr unknown
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BR112021005936A2 (pt) | 2021-06-29 |
JP2022502440A (ja) | 2022-01-11 |
WO2020065614A1 (fr) | 2020-04-02 |
JP2024038151A (ja) | 2024-03-19 |
EP3856179A1 (fr) | 2021-08-04 |
TW202035409A (zh) | 2020-10-01 |
MA53722A (fr) | 2022-03-30 |
US11993601B2 (en) | 2024-05-28 |
US20220315583A1 (en) | 2022-10-06 |
US20230242531A1 (en) | 2023-08-03 |
CN113164458A (zh) | 2021-07-23 |
MX2021003661A (es) | 2021-08-19 |
KR20210069079A (ko) | 2021-06-10 |
AU2019349962A1 (en) | 2021-03-18 |
CA3111309A1 (fr) | 2020-04-02 |
US11597728B2 (en) | 2023-03-07 |
JP7413368B2 (ja) | 2024-01-15 |
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