UA79507C2 - Purine compounds and uses thereof as cannabinoid receptor ligands - Google Patents

Info

Publication number

UA79507C2

UA79507C2 UAA200504047A UA2005004047A UA79507C2 UA 79507 C2 UA79507 C2 UA 79507C2 UA A200504047 A UAA200504047 A UA A200504047A UA 2005004047 A UA2005004047 A UA 2005004047A UA 79507 C2 UA79507 C2 UA 79507C2

Authority

UA

Ukraine

Prior art keywords

alkyl

alkylamino

partially

aryl

heteroaryl

Prior art date

2002-10-28

Links

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• Global Dossier
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• 102000018208 Cannabinoid Receptor Human genes 0.000 title abstract description 19
• 108050007331 Cannabinoid receptor Proteins 0.000 title abstract description 19
• 239000003446 ligand Substances 0.000 title abstract description 14
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 383
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
• 238000011282 treatment Methods 0.000 claims abstract description 38
• 241001465754 Metazoa Species 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 314
• 125000003282 alkyl amino group Chemical group 0.000 claims description 181
• 229920006395 saturated elastomer Polymers 0.000 claims description 175
• -1 cyano, hydroxy, amino Chemical group 0.000 claims description 169
• 125000003118 aryl group Chemical group 0.000 claims description 154
• 125000001072 heteroaryl group Chemical group 0.000 claims description 146
• 239000001257 hydrogen Substances 0.000 claims description 138
• 229910052739 hydrogen Inorganic materials 0.000 claims description 138
• 125000000623 heterocyclic group Chemical group 0.000 claims description 136
• 239000000203 mixture Substances 0.000 claims description 112
• 239000000126 substance Substances 0.000 claims description 106
• 238000000034 method Methods 0.000 claims description 105
• 125000002252 acyl group Chemical group 0.000 claims description 91
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 81
• 150000002431 hydrogen Chemical class 0.000 claims description 77
• 150000003839 salts Chemical class 0.000 claims description 75
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
• 239000005977 Ethylene Substances 0.000 claims description 55
• 150000003951 lactams Chemical group 0.000 claims description 53
• 150000002596 lactones Chemical group 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 125000004423 acyloxy group Chemical group 0.000 claims description 44
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
• 229910052760 oxygen Inorganic materials 0.000 claims description 44
• 239000001301 oxygen Substances 0.000 claims description 44
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 43
• 229910052717 sulfur Inorganic materials 0.000 claims description 43
• 239000011593 sulfur Substances 0.000 claims description 43
• 229940002612 prodrug Drugs 0.000 claims description 42
• 239000000651 prodrug Substances 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 40
• 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 38
• 125000004442 acylamino group Chemical group 0.000 claims description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 125000002837 carbocyclic group Chemical group 0.000 claims description 33
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 25
• 150000001408 amides Chemical class 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 22
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 20
• 239000008177 pharmaceutical agent Substances 0.000 claims description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 229910052796 boron Inorganic materials 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000003107 substituted aryl group Chemical group 0.000 claims description 16
• 239000003085 diluting agent Substances 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 13
• 239000000883 anti-obesity agent Substances 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 11
• 229940125710 antiobesity agent Drugs 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims description 10
• 229940122820 Cannabinoid receptor antagonist Drugs 0.000 claims description 9
• 239000003536 cannabinoid receptor antagonist Substances 0.000 claims description 9
• 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical class 0.000 claims description 8
• MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims description 8
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical group 0.000 claims description 6
• 229940126601 medicinal product Drugs 0.000 claims description 6
• 239000004031 partial agonist Substances 0.000 claims description 6
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 5
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 5
• 229940123257 Opioid receptor antagonist Drugs 0.000 claims description 5
• 229940005501 dopaminergic agent Drugs 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 claims description 4
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
• MZRPLPNMEBKVMW-UHFFFAOYSA-N 6-(1-benzylpyrrolidin-3-yl)oxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(OC3CN(CC=4C=CC=CC=4)CC3)=C2N=C1C1=CC=C(Cl)C=C1Cl MZRPLPNMEBKVMW-UHFFFAOYSA-N 0.000 claims description 2
• VNOGOEOTNFURPS-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyrimidin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CN=3)=C2N=C1C1=CC=C(Cl)C=C1Cl VNOGOEOTNFURPS-UHFFFAOYSA-N 0.000 claims description 2
• MOMMTIGOEFZQSC-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-propan-2-yloxypurine Chemical compound N=1C=2C(OC(C)C)=NC=NC=2N(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl MOMMTIGOEFZQSC-UHFFFAOYSA-N 0.000 claims description 2
• 239000003401 opiate antagonist Substances 0.000 claims description 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 125000004400 (C1-C12) alkyl group Chemical class 0.000 claims 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• RYVNIFSIEDRLSJ-UHFFFAOYSA-N 5-(hydroxymethyl)cytosine Chemical compound NC=1NC(=O)N=CC=1CO RYVNIFSIEDRLSJ-UHFFFAOYSA-N 0.000 claims 1
• HDPLEFUIDWOLLX-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyridin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1Cl HDPLEFUIDWOLLX-UHFFFAOYSA-N 0.000 claims 1
• 229910003294 NiMo Inorganic materials 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 205
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 155
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
• 239000000543 intermediate Chemical class 0.000 description 94
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
• 239000011541 reaction mixture Substances 0.000 description 83
• 238000002360 preparation method Methods 0.000 description 82
• 239000000243 solution Substances 0.000 description 80
• 238000005481 NMR spectroscopy Methods 0.000 description 69
• 239000007787 solid Substances 0.000 description 66
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 239000012044 organic layer Substances 0.000 description 38
• 235000019441 ethanol Nutrition 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
• 239000002904 solvent Substances 0.000 description 33
• 238000003756 stirring Methods 0.000 description 33
• 239000000463 material Substances 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 230000002829 reductive effect Effects 0.000 description 30
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 29
• 239000003153 chemical reaction reagent Substances 0.000 description 28
• 230000015572 biosynthetic process Effects 0.000 description 27
• 239000010949 copper Substances 0.000 description 27
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• 239000000556 agonist Substances 0.000 description 26
• 238000003786 synthesis reaction Methods 0.000 description 25
• 239000003826 tablet Substances 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• 239000005557 antagonist Substances 0.000 description 21
• 238000010992 reflux Methods 0.000 description 21
• 208000007848 Alcoholism Diseases 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 239000003480 eluent Substances 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
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• 238000012360 testing method Methods 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
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• 208000035475 disorder Diseases 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 201000007930 alcohol dependence Diseases 0.000 description 16
• 229910052801 chlorine Inorganic materials 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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• 150000003840 hydrochlorides Chemical class 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 13
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• 230000027455 binding Effects 0.000 description 13
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