SG188346A1 - 1,4-oxazepane derivatives - Google Patents

Info

Publication number

SG188346A1

SG188346A1 SG2013015268A SG2013015268A SG188346A1 SG 188346 A1 SG188346 A1 SG 188346A1 SG 2013015268 A SG2013015268 A SG 2013015268A SG 2013015268 A SG2013015268 A SG 2013015268A SG 188346 A1 SG188346 A1 SG 188346A1

Authority

SG

Singapore

Prior art keywords

group

optionally substituted

compound

alkyl

ring

Prior art date

2010-10-07

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• 150000000324 1,4-oxazepanes Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 542
• 125000001424 substituent group Chemical group 0.000 claims abstract description 250
• 125000003118 aryl group Chemical group 0.000 claims abstract description 81
• 150000003839 salts Chemical class 0.000 claims abstract description 80
• -1 sulfamoylamino group Chemical group 0.000 claims description 633
• 125000000217 alkyl group Chemical group 0.000 claims description 266
• 238000000034 method Methods 0.000 claims description 170
• 125000003277 amino group Chemical group 0.000 claims description 143
• 125000000623 heterocyclic group Chemical group 0.000 claims description 132
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 128
• 125000003545 alkoxy group Chemical group 0.000 claims description 121
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 116
• 125000005843 halogen group Chemical group 0.000 claims description 88
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 61
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 56
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 52
• 229910052731 fluorine Inorganic materials 0.000 claims description 51
• 125000001153 fluoro group Chemical group F* 0.000 claims description 51
• 239000003814 drug Substances 0.000 claims description 46
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 229910052801 chlorine Inorganic materials 0.000 claims description 38
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 229940126585 therapeutic drug Drugs 0.000 claims description 26
• 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 21
• 208000019901 Anxiety disease Diseases 0.000 claims description 19
• 125000004104 aryloxy group Chemical group 0.000 claims description 19
• 230000036506 anxiety Effects 0.000 claims description 18
• 208000002193 Pain Diseases 0.000 claims description 17
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 17
• 230000036407 pain Effects 0.000 claims description 17
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 16
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 16
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 15
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 15
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
• 206010046543 Urinary incontinence Diseases 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 230000000069 prophylactic effect Effects 0.000 claims description 13
• 229940043274 prophylactic drug Drugs 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• 150000001555 benzenes Chemical group 0.000 claims description 8
• BKYNHOGAASXLEV-UHFFFAOYSA-N 2-methyl-2-phenyl-1,4-oxazepane Chemical compound C=1C=CC=CC=1C1(C)CNCCCO1 BKYNHOGAASXLEV-UHFFFAOYSA-N 0.000 claims description 7
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 7
• 229940126403 monoamine reuptake inhibitor Drugs 0.000 claims description 6
• 230000036961 partial effect Effects 0.000 claims description 6
• OJUYHLMOHQANOU-UHFFFAOYSA-N 7-methyl-7-phenyl-1,4-oxazepane Chemical compound C=1C=CC=CC=1C1(C)CCNCCO1 OJUYHLMOHQANOU-UHFFFAOYSA-N 0.000 claims description 5
• 208000020401 Depressive disease Diseases 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• CFHMIFNNYVJLRQ-UHFFFAOYSA-N 6-methyl-6-phenyl-1,4-oxazepane Chemical compound C=1C=CC=CC=1C1(C)CNCCOC1 CFHMIFNNYVJLRQ-UHFFFAOYSA-N 0.000 claims description 4
• JSXUKIZDGHZTQO-UHFFFAOYSA-N 7-hydroxy-7-(4-methoxyphenyl)-1,4-oxazepan-2-one Chemical compound C1=CC(OC)=CC=C1C1(O)OC(=O)CNCC1 JSXUKIZDGHZTQO-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• NVCYESZQCJFSDL-NSHDSACASA-N (2r)-2-phenyl-2-(trifluoromethyl)-1,4-oxazepane Chemical compound C=1C=CC=CC=1[C@]1(C(F)(F)F)CNCCCO1 NVCYESZQCJFSDL-NSHDSACASA-N 0.000 claims description 3
• HLXVRAJJPNUXKL-UHFFFAOYSA-N oxazepan-5-one Chemical compound O=C1CCNOCC1 HLXVRAJJPNUXKL-UHFFFAOYSA-N 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 abstract description 21
• 230000000407 monoamine reuptake Effects 0.000 abstract description 9
• 125000004043 oxo group Chemical group O=* 0.000 description 116
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 106
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 description 80
• 125000006239 protecting group Chemical group 0.000 description 58
• 239000000203 mixture Substances 0.000 description 55
• 238000006243 chemical reaction Methods 0.000 description 54
• 239000000243 solution Substances 0.000 description 54
• 125000004122 cyclic group Chemical group 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 47
• 238000002360 preparation method Methods 0.000 description 46
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 40
• 230000002829 reductive effect Effects 0.000 description 40
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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• 235000019439 ethyl acetate Nutrition 0.000 description 31
• 229940093499 ethyl acetate Drugs 0.000 description 31
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• 239000011541 reaction mixture Substances 0.000 description 29
• 239000002585 base Substances 0.000 description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
• 230000009467 reduction Effects 0.000 description 26
• 238000006722 reduction reaction Methods 0.000 description 26
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 26
• 238000003786 synthesis reaction Methods 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 23
• 230000015572 biosynthetic process Effects 0.000 description 22
• 125000000753 cycloalkyl group Chemical group 0.000 description 22
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 22
• 239000000126 substance Substances 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 125000003710 aryl alkyl group Chemical group 0.000 description 18
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 18
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• 238000010898 silica gel chromatography Methods 0.000 description 16
• 125000001425 triazolyl group Chemical group 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• 125000003282 alkyl amino group Chemical group 0.000 description 15
• 239000012267 brine Substances 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 14
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 14
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• 239000012153 distilled water Substances 0.000 description 14
• 229960002748 norepinephrine Drugs 0.000 description 14
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 14
• 230000003287 optical effect Effects 0.000 description 14
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• 229910052783 alkali metal Inorganic materials 0.000 description 13
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 13
• 201000010099 disease Diseases 0.000 description 13
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• 125000003831 tetrazolyl group Chemical group 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000004414 alkyl thio group Chemical group 0.000 description 12
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 12
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 12
• 229940076279 serotonin Drugs 0.000 description 12
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
• 150000001342 alkaline earth metals Chemical class 0.000 description 11
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• 229960003638 dopamine Drugs 0.000 description 11
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• 150000002148 esters Chemical class 0.000 description 11
• 239000012280 lithium aluminium hydride Substances 0.000 description 11
• 238000001819 mass spectrum Methods 0.000 description 11
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• 125000000335 thiazolyl group Chemical group 0.000 description 11
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 10
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• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 10
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
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• 125000005554 pyridyloxy group Chemical group 0.000 description 10
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
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• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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