CA2591766C - Tetrahydroquinoline analogues as muscarinic agonists - Google Patents

Info

Publication number

CA2591766C

CA2591766C CA2591766A CA2591766A CA2591766C CA 2591766 C CA2591766 C CA 2591766C CA 2591766 A CA2591766 A CA 2591766A CA 2591766 A CA2591766 A CA 2591766A CA 2591766 C CA2591766 C CA 2591766C

Authority

CA

Canada

Prior art keywords

optionally substituted

mmol

branched

straight

compound

Prior art date

2004-12-21

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.)

Expired - Fee Related

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• 239000000472 muscarinic agonist Substances 0.000 title claims description 11
• 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 434
• 239000000203 mixture Substances 0.000 claims abstract description 79
• 238000000034 method Methods 0.000 claims abstract description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims abstract description 45
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims abstract description 45
• 230000000694 effects Effects 0.000 claims abstract description 45
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims description 106
• -1 substituted Chemical class 0.000 claims description 69
• 102000009660 Cholinergic Receptors Human genes 0.000 claims description 56
• 108010009685 Cholinergic Receptors Proteins 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 43
• 150000002367 halogens Chemical group 0.000 claims description 43
• 208000035475 disorder Diseases 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 230000008484 agonism Effects 0.000 claims description 20
• 150000002148 esters Chemical class 0.000 claims description 20
• 229940002612 prodrug Drugs 0.000 claims description 20
• 239000000651 prodrug Substances 0.000 claims description 20
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 208000024891 symptom Diseases 0.000 claims description 18
• 230000004044 response Effects 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 230000006735 deficit Effects 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 13
• 230000008485 antagonism Effects 0.000 claims description 13
• 230000009286 beneficial effect Effects 0.000 claims description 13
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• 230000004410 intraocular pressure Effects 0.000 claims description 13
• 201000000980 schizophrenia Diseases 0.000 claims description 13
• 208000020016 psychiatric disease Diseases 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• 208000010412 Glaucoma Diseases 0.000 claims description 11
• 208000028017 Psychotic disease Diseases 0.000 claims description 11
• 102000017925 CHRM3 Human genes 0.000 claims description 10
• 101150060249 CHRM3 gene Proteins 0.000 claims description 10
• 208000028698 Cognitive impairment Diseases 0.000 claims description 10
• 208000010877 cognitive disease Diseases 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 208000024827 Alzheimer disease Diseases 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 206010012289 Dementia Diseases 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 230000003551 muscarinic effect Effects 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 208000000044 Amnesia Diseases 0.000 claims description 7
• 206010003591 Ataxia Diseases 0.000 claims description 7
• 201000010374 Down Syndrome Diseases 0.000 claims description 7
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 7
• 208000023105 Huntington disease Diseases 0.000 claims description 7
• 208000026139 Memory disease Diseases 0.000 claims description 7
• 102000007207 Muscarinic M1 Receptor Human genes 0.000 claims description 7
• 108010008406 Muscarinic M1 Receptor Proteins 0.000 claims description 7
• 208000002193 Pain Diseases 0.000 claims description 7
• 208000018737 Parkinson disease Diseases 0.000 claims description 7
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 7
• 208000024571 Pick disease Diseases 0.000 claims description 7
• 208000034972 Sudden Infant Death Diseases 0.000 claims description 7
• 206010042440 Sudden infant death syndrome Diseases 0.000 claims description 7
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 7
• 230000007000 age related cognitive decline Effects 0.000 claims description 7
• 230000006984 memory degeneration Effects 0.000 claims description 7
• 206010027175 memory impairment Diseases 0.000 claims description 7
• 208000023060 memory loss Diseases 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 208000019116 sleep disease Diseases 0.000 claims description 7
• 230000016776 visual perception Effects 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• 102000007205 Muscarinic M2 Receptor Human genes 0.000 claims description 4
• 108010008407 Muscarinic M2 Receptor Proteins 0.000 claims description 4
• 125000001118 alkylidene group Chemical group 0.000 claims description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
• 230000004770 neurodegeneration Effects 0.000 claims description 4
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 3
• 102000007216 Muscarinic M4 Receptor Human genes 0.000 claims description 3
• 108010008414 Muscarinic M4 Receptor Proteins 0.000 claims description 3
• 206010044688 Trisomy 21 Diseases 0.000 claims description 3
• 125000005819 alkenylalkoxy group Chemical group 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 238000000338 in vitro Methods 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims 1
• 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 101150113676 chr1 gene Proteins 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000000547 substituted alkyl group Chemical group 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 abstract description 5
• 229940044601 receptor agonist Drugs 0.000 abstract description 2
• 239000000018 receptor agonist Substances 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 390
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 338
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 249
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
• 235000019439 ethyl acetate Nutrition 0.000 description 195
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 180
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 177
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 175
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 172
• 101150041968 CDC13 gene Proteins 0.000 description 166
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 145
• 229910052681 coesite Inorganic materials 0.000 description 139
• 229910052906 cristobalite Inorganic materials 0.000 description 139
• 229910052682 stishovite Inorganic materials 0.000 description 139
• 229910052905 tridymite Inorganic materials 0.000 description 139
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 120
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 117
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 112
• 239000000047 product Substances 0.000 description 111
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 110
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 109
• 238000005481 NMR spectroscopy Methods 0.000 description 103
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 98
• 239000005695 Ammonium acetate Substances 0.000 description 98
• 235000019257 ammonium acetate Nutrition 0.000 description 98
• 229940043376 ammonium acetate Drugs 0.000 description 98
• 239000007832 Na2SO4 Substances 0.000 description 84
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 84
• 229910052938 sodium sulfate Inorganic materials 0.000 description 84
• 235000011152 sodium sulphate Nutrition 0.000 description 84
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 74
• 239000011541 reaction mixture Substances 0.000 description 72
• 229910000027 potassium carbonate Inorganic materials 0.000 description 67
• 239000012044 organic layer Substances 0.000 description 61
• 239000013078 crystal Substances 0.000 description 59
• 235000006408 oxalic acid Nutrition 0.000 description 59
• XIQSPCJCAJVNJL-UHFFFAOYSA-N 4-butylpiperidine Chemical compound CCCCC1CCNCC1 XIQSPCJCAJVNJL-UHFFFAOYSA-N 0.000 description 56
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 54
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 52
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 51
• 238000006243 chemical reaction Methods 0.000 description 51
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
• 230000002829 reductive effect Effects 0.000 description 47
• 238000005160 1H NMR spectroscopy Methods 0.000 description 41
• 235000009518 sodium iodide Nutrition 0.000 description 39
• 239000003921 oil Substances 0.000 description 38
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000012074 organic phase Substances 0.000 description 36
• 238000005341 cation exchange Methods 0.000 description 35
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 33
• FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 30
• 150000002431 hydrogen Chemical class 0.000 description 30
• 108020003175 receptors Proteins 0.000 description 30
• 102000005962 receptors Human genes 0.000 description 29
• 229910000024 caesium carbonate Inorganic materials 0.000 description 27
• 239000012071 phase Substances 0.000 description 27
• 229910000104 sodium hydride Inorganic materials 0.000 description 27
• 235000015320 potassium carbonate Nutrition 0.000 description 26
• SFOYQZYQTQDRIY-UHFFFAOYSA-N 1-chloro-3-iodopropane Chemical compound ClCCCI SFOYQZYQTQDRIY-UHFFFAOYSA-N 0.000 description 25
• 239000000556 agonist Substances 0.000 description 25
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• 238000003756 stirring Methods 0.000 description 24
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 23
• VOWMRECKIQVVPP-UHFFFAOYSA-N 4-propoxypiperidine Chemical compound CCCOC1CCNCC1 VOWMRECKIQVVPP-UHFFFAOYSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
• 239000012267 brine Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
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• 238000000746 purification Methods 0.000 description 17
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
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• 238000004007 reversed phase HPLC Methods 0.000 description 14
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
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• 238000003818 flash chromatography Methods 0.000 description 12
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• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 12
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• QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 11
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• QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 9
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 9
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• CTSRPUVQHXNPGP-UHFFFAOYSA-N 1-(3-chloropropyl)-7-methyl-3,4-dihydroquinolin-2-one Chemical compound C1CC(=O)N(CCCCl)C2=CC(C)=CC=C21 CTSRPUVQHXNPGP-UHFFFAOYSA-N 0.000 description 6
• NZNNOIBGTIMFPV-UHFFFAOYSA-N 3-butyl-8-azabicyclo[3.2.1]octane Chemical compound C1C(CCCC)CC2CCC1N2 NZNNOIBGTIMFPV-UHFFFAOYSA-N 0.000 description 6
• OGTZNZMJKSVJED-UHFFFAOYSA-N 3-pentyl-8-azabicyclo[3.2.1]octane Chemical compound C1C(CCCCC)CC2CCC1N2 OGTZNZMJKSVJED-UHFFFAOYSA-N 0.000 description 6
• SXSJFHLBTSAKPQ-UHFFFAOYSA-N 6-fluoro-7-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=C(C)C(F)=C2 SXSJFHLBTSAKPQ-UHFFFAOYSA-N 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
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• LWAVAWLBKZPMSS-UHFFFAOYSA-N 4-(3-chloropropyl)-1,4-benzoxazin-3-one Chemical compound C1=CC=C2N(CCCCl)C(=O)COC2=C1 LWAVAWLBKZPMSS-UHFFFAOYSA-N 0.000 description 5
• GRSJYHSWRWPUQB-SNVBAGLBSA-N 4-[(2s)-3-iodo-2-methylpropyl]-6-methyl-1,4-benzoxazin-3-one Chemical compound C1=C(C)C=C2N(C[C@@H](CI)C)C(=O)COC2=C1 GRSJYHSWRWPUQB-SNVBAGLBSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
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• 210000004556 brain Anatomy 0.000 description 5
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• PYFSLJVSCGXYAJ-UHFFFAOYSA-N methyl 2-hydroxy-4-[[3-(2-hydroxyphenyl)phenyl]sulfonylamino]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=CC(C=2C(=CC=CC=2)O)=C1 PYFSLJVSCGXYAJ-UHFFFAOYSA-N 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 238000002953 preparative HPLC Methods 0.000 description 5
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