ZA200205322B - Nitrogenous cyclic compounds and pharmaceutical compositions containing the same. - Google Patents
Nitrogenous cyclic compounds and pharmaceutical compositions containing the same. Download PDFInfo
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- ZA200205322B ZA200205322B ZA200205322A ZA200205322A ZA200205322B ZA 200205322 B ZA200205322 B ZA 200205322B ZA 200205322 A ZA200205322 A ZA 200205322A ZA 200205322 A ZA200205322 A ZA 200205322A ZA 200205322 B ZA200205322 B ZA 200205322B
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- South Africa
- Prior art keywords
- group
- substituted
- cyano
- ring
- indicates
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- -1 Nitrogenous cyclic compounds Chemical class 0.000 title claims description 374
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 346
- 239000000203 mixture Substances 0.000 claims description 223
- 125000000217 alkyl group Chemical group 0.000 claims description 167
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 104
- 150000003839 salts Chemical class 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 80
- 125000005843 halogen group Chemical group 0.000 claims description 74
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
- 125000002560 nitrile group Chemical group 0.000 claims description 56
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 50
- 125000003342 alkenyl group Chemical group 0.000 claims description 46
- 125000002947 alkylene group Chemical group 0.000 claims description 46
- 230000002490 cerebral effect Effects 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 38
- 125000002252 acyl group Chemical group 0.000 claims description 36
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 210000003061 neural cell Anatomy 0.000 claims description 24
- 230000001537 neural effect Effects 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 206010008118 cerebral infarction Diseases 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 15
- 108090000699 N-Type Calcium Channels Proteins 0.000 claims description 15
- 102000004129 N-Type Calcium Channels Human genes 0.000 claims description 15
- 239000000480 calcium channel blocker Substances 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 108700012358 P/Q-type calcium channel Proteins 0.000 claims description 14
- 102000050761 P/Q-type calcium channel Human genes 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 206010019196 Head injury Diseases 0.000 claims description 11
- 208000019695 Migraine disease Diseases 0.000 claims description 11
- 208000002193 Pain Diseases 0.000 claims description 11
- 208000006011 Stroke Diseases 0.000 claims description 11
- 206010015037 epilepsy Diseases 0.000 claims description 11
- 150000002430 hydrocarbons Chemical group 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 206010027599 migraine Diseases 0.000 claims description 11
- 230000036407 pain Effects 0.000 claims description 11
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 201000006474 Brain Ischemia Diseases 0.000 claims description 10
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 10
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 10
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 10
- 206010030113 Oedema Diseases 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 230000030833 cell death Effects 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000030507 AIDS Diseases 0.000 claims description 9
- 206010012289 Dementia Diseases 0.000 claims description 9
- 208000023105 Huntington disease Diseases 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
- 208000005392 Spasm Diseases 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 8
- 230000034994 death Effects 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 201000004810 Vascular dementia Diseases 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 208000028683 bipolar I disease Diseases 0.000 claims description 7
- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- 210000002569 neuron Anatomy 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 230000004087 circulation Effects 0.000 claims description 6
- 230000036961 partial effect Effects 0.000 claims description 6
- 230000002633 protecting effect Effects 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 230000008485 antagonism Effects 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000002503 metabolic effect Effects 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 229940125400 channel inhibitor Drugs 0.000 claims description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- SMANTNBDDJUWPC-UHFFFAOYSA-N 2-phenyl-5-[4-(4-phenylpiperidin-1-yl)piperidin-1-yl]-2-propan-2-ylpentanenitrile Chemical compound C=1C=CC=CC=1C(C(C)C)(C#N)CCCN(CC1)CCC1N(CC1)CCC1C1=CC=CC=C1 SMANTNBDDJUWPC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- GWOWLSFGWWZDOM-DXDQHDRFSA-N 5-[6-[(3r)-3-[benzyl(2-cyanoethyl)amino]pyrrolidin-1-yl]-3-cyano-2-methylhexan-3-yl]thiophene-2-carbonitrile Chemical compound N#CCCN([C@@H]1CCN(C1)CCCC(C(C)C)(C#N)C=1SC(=CC=1)C#N)CC1=CC=CC=C1 GWOWLSFGWWZDOM-DXDQHDRFSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- OEPQEIQIOLIMGF-UHFFFAOYSA-N 3-[2-[4-(4-cyano-5-methyl-4-thiophen-2-ylhexyl)piperazin-1-yl]ethoxy]benzonitrile Chemical compound C=1C=CSC=1C(C(C)C)(C#N)CCCN(CC1)CCN1CCOC1=CC=CC(C#N)=C1 OEPQEIQIOLIMGF-UHFFFAOYSA-N 0.000 claims 1
- GVDUKPVDFXGFEM-UHFFFAOYSA-N 5-[3-cyano-6-[4-[2-(3-fluorophenoxy)ethyl]piperazin-1-yl]-2-methylhexan-3-yl]thiophene-2-carbonitrile Chemical compound C=1C=C(C#N)SC=1C(C(C)C)(C#N)CCCN(CC1)CCN1CCOC1=CC=CC(F)=C1 GVDUKPVDFXGFEM-UHFFFAOYSA-N 0.000 claims 1
- XCLNZZVJSMBOIO-UHFFFAOYSA-N 5-[4-[2-(3-fluorophenoxy)ethyl]piperazin-1-yl]-2-propan-2-yl-2-thiophen-2-ylpentanenitrile Chemical compound C=1C=CSC=1C(C(C)C)(C#N)CCCN(CC1)CCN1CCOC1=CC=CC(F)=C1 XCLNZZVJSMBOIO-UHFFFAOYSA-N 0.000 claims 1
- GWOWLSFGWWZDOM-BXXZMZEQSA-N 5-[6-[(3s)-3-[benzyl(2-cyanoethyl)amino]pyrrolidin-1-yl]-3-cyano-2-methylhexan-3-yl]thiophene-2-carbonitrile Chemical compound N#CCCN([C@H]1CCN(C1)CCCC(C(C)C)(C#N)C=1SC(=CC=1)C#N)CC1=CC=CC=C1 GWOWLSFGWWZDOM-BXXZMZEQSA-N 0.000 claims 1
- 229920006063 Lamide® Polymers 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229940099990 ogen Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 583
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 313
- 238000005160 1H NMR spectroscopy Methods 0.000 description 151
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 150
- 239000012267 brine Substances 0.000 description 139
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 139
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 135
- 239000012043 crude product Substances 0.000 description 129
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 113
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 111
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 108
- 239000012044 organic layer Substances 0.000 description 108
- 239000000243 solution Substances 0.000 description 106
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 105
- 239000003921 oil Substances 0.000 description 100
- 235000019198 oils Nutrition 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 238000006243 chemical reaction Methods 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 57
- 238000003756 stirring Methods 0.000 description 55
- 239000000741 silica gel Substances 0.000 description 53
- 229910002027 silica gel Inorganic materials 0.000 description 53
- 238000010898 silica gel chromatography Methods 0.000 description 51
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 38
- 235000019341 magnesium sulphate Nutrition 0.000 description 38
- 238000001914 filtration Methods 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000007796 conventional method Methods 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 31
- 238000010438 heat treatment Methods 0.000 description 29
- 239000002274 desiccant Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 27
- 239000000126 substance Substances 0.000 description 26
- 239000012230 colorless oil Substances 0.000 description 25
- 239000006188 syrup Substances 0.000 description 25
- 235000020357 syrup Nutrition 0.000 description 25
- 239000013078 crystal Substances 0.000 description 24
- 238000001816 cooling Methods 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 20
- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 17
- 235000009518 sodium iodide Nutrition 0.000 description 17
- 239000003814 drug Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 125000001153 fluoro group Chemical group F* 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
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- DQQJBEAXSOOCPG-SSDOTTSWSA-N tert-butyl n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCNC1 DQQJBEAXSOOCPG-SSDOTTSWSA-N 0.000 description 1
- DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
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- WAOWQLJJQBDGQC-UHFFFAOYSA-N tetraazanium;tetrafluoride Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[F-].[F-].[F-].[F-] WAOWQLJJQBDGQC-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
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- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
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- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical group N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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US (3) | US6906072B1 (xx) |
EP (2) | EP1818326A1 (xx) |
KR (1) | KR20020069362A (xx) |
CN (1) | CN1205185C (xx) |
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HK (1) | HK1049004A1 (xx) |
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IL (1) | IL150651A0 (xx) |
MX (1) | MXPA02007035A (xx) |
NO (1) | NO20023456L (xx) |
NZ (1) | NZ519981A (xx) |
RU (1) | RU2230060C2 (xx) |
WO (1) | WO2001053258A1 (xx) |
ZA (1) | ZA200205322B (xx) |
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US8710045B2 (en) | 2004-01-22 | 2014-04-29 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the ryanodine receptors |
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2001
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- 2001-01-18 RU RU2002122335/04A patent/RU2230060C2/ru not_active IP Right Cessation
- 2001-01-18 CN CNB01803988XA patent/CN1205185C/zh not_active Expired - Fee Related
- 2001-01-18 BR BR0107733-3A patent/BR0107733A/pt not_active IP Right Cessation
- 2001-01-18 HU HU0204071A patent/HUP0204071A3/hu unknown
- 2001-01-18 MX MXPA02007035A patent/MXPA02007035A/es active IP Right Grant
- 2001-01-18 IL IL15065101A patent/IL150651A0/xx unknown
- 2001-01-18 WO PCT/JP2001/000288 patent/WO2001053258A1/ja active IP Right Grant
- 2001-01-18 EP EP06016525A patent/EP1818326A1/en not_active Withdrawn
- 2001-01-18 CA CA002398409A patent/CA2398409A1/en not_active Abandoned
- 2001-01-18 EP EP01901413A patent/EP1254895B1/en not_active Expired - Lifetime
- 2001-01-18 NZ NZ519981A patent/NZ519981A/en unknown
- 2001-01-18 KR KR1020027009235A patent/KR20020069362A/ko active IP Right Grant
- 2001-01-18 DE DE60128542T patent/DE60128542T2/de not_active Expired - Lifetime
- 2001-01-18 AT AT01901413T patent/ATE362926T1/de not_active IP Right Cessation
- 2001-01-18 AU AU27059/01A patent/AU779870B2/en not_active Ceased
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- 2002-07-03 ZA ZA200205322A patent/ZA200205322B/en unknown
- 2002-07-18 NO NO20023456A patent/NO20023456L/no not_active Application Discontinuation
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- 2003-02-19 HK HK03101263.5A patent/HK1049004A1/zh unknown
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EP1254895B1 (en) | 2007-05-23 |
DE60128542D1 (de) | 2007-07-05 |
EP1818326A1 (en) | 2007-08-15 |
KR20020069362A (ko) | 2002-08-30 |
HUP0204071A3 (en) | 2003-07-28 |
DE60128542T2 (de) | 2008-01-31 |
MXPA02007035A (es) | 2002-12-13 |
NO20023456L (no) | 2002-09-20 |
US20060084658A1 (en) | 2006-04-20 |
CN1395562A (zh) | 2003-02-05 |
WO2001053258A1 (fr) | 2001-07-26 |
EP1254895A1 (en) | 2002-11-06 |
US6906072B1 (en) | 2005-06-14 |
NZ519981A (en) | 2005-02-25 |
CA2398409A1 (en) | 2001-07-26 |
EP1254895A4 (en) | 2003-01-22 |
HUP0204071A2 (hu) | 2003-03-28 |
HK1049004A1 (zh) | 2003-04-25 |
RU2002122335A (ru) | 2004-01-10 |
RU2230060C2 (ru) | 2004-06-10 |
US20040220193A1 (en) | 2004-11-04 |
ATE362926T1 (de) | 2007-06-15 |
CN1205185C (zh) | 2005-06-08 |
AU2705901A (en) | 2001-07-31 |
NO20023456D0 (no) | 2002-07-18 |
IL150651A0 (en) | 2003-02-12 |
BR0107733A (pt) | 2003-03-11 |
AU779870B2 (en) | 2005-02-17 |
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