JP4852536B2 - 置換されたシクロヘキシル酢酸誘導体 - Google Patents

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Publication number

JP4852536B2

JP4852536B2 JP2007512029A JP2007512029A JP4852536B2 JP 4852536 B2 JP4852536 B2 JP 4852536B2 JP 2007512029 A JP2007512029 A JP 2007512029A JP 2007512029 A JP2007512029 A JP 2007512029A JP 4852536 B2 JP4852536 B2 JP 4852536B2

Authority

JP

Japan

Prior art keywords

dimethylamino

acetamide

hydrochloride

phenyl

mmol

Prior art date

2004-05-10

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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• LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical class OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 title claims abstract description 40
• 150000001875 compounds Chemical class 0.000 claims abstract description 43
• 238000000034 method Methods 0.000 claims abstract description 25
• 238000004519 manufacturing process Methods 0.000 claims abstract description 20
• 230000008569 process Effects 0.000 claims abstract description 7
• -1 4-dimethylamino-4-phenyl-cyclohexylidene Chemical group 0.000 claims description 170
• 239000000203 mixture Substances 0.000 claims description 67
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
• 239000003814 drug Substances 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
• 208000002193 Pain Diseases 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 19
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 18
• 239000003054 catalyst Substances 0.000 claims description 18
• 239000002585 base Substances 0.000 claims description 17
• 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 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 239000013543 active substance Substances 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 150000001768 cations Chemical class 0.000 claims description 9
• XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 229940005483 opioid analgesics Drugs 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 150000007513 acids Chemical class 0.000 claims description 7
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 7
• 229910052763 palladium Inorganic materials 0.000 claims description 7
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
• 208000000094 Chronic Pain Diseases 0.000 claims description 5
• 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 5
• MJVDUTFFYILLRR-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide Chemical compound C=1NC2=CC=CC=C2C=1CC(C)NC(=O)CC(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 MJVDUTFFYILLRR-UHFFFAOYSA-N 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 4
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
• 230000036506 anxiety Effects 0.000 claims description 4
• 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims description 4
• XFTPQJQBMJHZKF-UHFFFAOYSA-N methyl 2-[[2-[4-(dimethylamino)-4-phenylcyclohexylidene]acetyl]amino]-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C(=O)OC)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC=C1 XFTPQJQBMJHZKF-UHFFFAOYSA-N 0.000 claims description 4
• 229910052703 rhodium Inorganic materials 0.000 claims description 4
• 239000010948 rhodium Substances 0.000 claims description 4
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
• 208000009132 Catalepsy Diseases 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 206010046543 Urinary incontinence Diseases 0.000 claims description 3
• 206010047853 Waxy flexibility Diseases 0.000 claims description 3
• 230000001154 acute effect Effects 0.000 claims description 3
• 208000005298 acute pain Diseases 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• 208000022531 anorexia Diseases 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 206010061428 decreased appetite Diseases 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• 206010015037 epilepsy Diseases 0.000 claims description 3
• 238000010931 ester hydrolysis Methods 0.000 claims description 3
• 230000029142 excretion Effects 0.000 claims description 3
• 229910052751 metal Inorganic materials 0.000 claims description 3
• 239000002184 metal Substances 0.000 claims description 3
• 230000037023 motor activity Effects 0.000 claims description 3
• 208000004296 neuralgia Diseases 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 230000002981 neuropathic effect Effects 0.000 claims description 3
• 208000021722 neuropathic pain Diseases 0.000 claims description 3
• 230000001777 nootropic effect Effects 0.000 claims description 3
• ZGELMQCVXODCBP-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 ZGELMQCVXODCBP-UHFFFAOYSA-N 0.000 claims description 2
• RXQWCUNKUKVDHD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 RXQWCUNKUKVDHD-UHFFFAOYSA-N 0.000 claims description 2
• KCIOTZNIJIPFON-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=CC(F)=C1 KCIOTZNIJIPFON-UHFFFAOYSA-N 0.000 claims description 2
• CJYQKUZVHJLIGS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(3-fluorophenyl)cyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC(F)=C1 CJYQKUZVHJLIGS-UHFFFAOYSA-N 0.000 claims description 2
• VSILQARCFWRDTB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=C(F)C=C1 VSILQARCFWRDTB-UHFFFAOYSA-N 0.000 claims description 2
• QQPIWEXJHHUYSU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC(F)=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 QQPIWEXJHHUYSU-UHFFFAOYSA-N 0.000 claims description 2
• NLOJFZZRPQCNMS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-(4-fluorophenyl)cyclohexylidene]-n-[1-(1h-indol-3-yl)propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C=C(CC1)CCC1(N(C)C)C1=CC=C(F)C=C1 NLOJFZZRPQCNMS-UHFFFAOYSA-N 0.000 claims description 2
• JKHUAAVDCKVKTP-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 JKHUAAVDCKVKTP-UHFFFAOYSA-N 0.000 claims description 2
• IRJYVPBUAJAONT-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-fluorophenyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NC1=CC=C(F)C=C1 IRJYVPBUAJAONT-UHFFFAOYSA-N 0.000 claims description 2
• VOQSWHYBHNXFFU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(4-phenylbutyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NCCCCC1=CC=CC=C1 VOQSWHYBHNXFFU-UHFFFAOYSA-N 0.000 claims description 2
• CUJYIQNNCFPCIE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[2-(1h-indol-3-yl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 CUJYIQNNCFPCIE-UHFFFAOYSA-N 0.000 claims description 2
• YLKSRBBBJYTVKJ-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[3-(1h-indol-3-yl)propyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 YLKSRBBBJYTVKJ-UHFFFAOYSA-N 0.000 claims description 2
• XKTKPRVXGIGROW-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[4-(1h-indol-3-yl)butyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 XKTKPRVXGIGROW-UHFFFAOYSA-N 0.000 claims description 2
• LULRVVPEJPXSTK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 LULRVVPEJPXSTK-UHFFFAOYSA-N 0.000 claims description 2
• JHZAXZMVHGRBBU-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-[6-(1h-indol-3-yl)hexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(CC(=O)NCCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 JHZAXZMVHGRBBU-UHFFFAOYSA-N 0.000 claims description 2
• DLENHNHTFWCBCK-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-phenylacetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1CC(=O)NC1=CC=CC=C1 DLENHNHTFWCBCK-UHFFFAOYSA-N 0.000 claims description 2
• SVHZXTOUDQHWIH-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 SVHZXTOUDQHWIH-UHFFFAOYSA-N 0.000 claims description 2
• BRNXKDIARBAMHE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-(4-fluorophenyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NC1=CC=C(F)C=C1 BRNXKDIARBAMHE-UHFFFAOYSA-N 0.000 claims description 2
• GDICGRWNXYWJSE-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[(4-fluorophenyl)methyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=C(F)C=C1 GDICGRWNXYWJSE-UHFFFAOYSA-N 0.000 claims description 2
• QGWRZBSRUFMXQA-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[2-(1h-indol-3-yl)ethyl]acetamide Chemical compound C1CC(=CC(=O)NCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 QGWRZBSRUFMXQA-UHFFFAOYSA-N 0.000 claims description 2
• DASCBEIQPSWVQR-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[2-(4-fluorophenyl)ethyl]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCCC1=CC=C(F)C=C1 DASCBEIQPSWVQR-UHFFFAOYSA-N 0.000 claims description 2
• IQFHGPWESACTJS-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[3-(1h-indol-3-yl)propyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 IQFHGPWESACTJS-UHFFFAOYSA-N 0.000 claims description 2
• NSDOZTVPWBRTLG-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[4-(1h-indol-3-yl)butyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 NSDOZTVPWBRTLG-UHFFFAOYSA-N 0.000 claims description 2
• XVNCJNDEVIOODN-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[5-(1h-indol-3-yl)pentyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 XVNCJNDEVIOODN-UHFFFAOYSA-N 0.000 claims description 2
• JMILVWBBDLLQBD-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-phenylcyclohexylidene]-n-[6-(1h-indol-3-yl)hexyl]acetamide;hydrochloride Chemical compound Cl.C1CC(=CC(=O)NCCCCCCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 JMILVWBBDLLQBD-UHFFFAOYSA-N 0.000 claims description 2
• KMTAMTDLIBHTFP-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexyl]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2N=CC=CC=2)CCC1CC(=O)NCCCC1=CC=CC=C1 KMTAMTDLIBHTFP-UHFFFAOYSA-N 0.000 claims description 2
• LWCOSZMDBZTTMB-UHFFFAOYSA-N 2-[4-(dimethylamino)-4-pyridin-2-ylcyclohexylidene]-n-(3-phenylpropyl)acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2N=CC=CC=2)CCC1=CC(=O)NCCCC1=CC=CC=C1 LWCOSZMDBZTTMB-UHFFFAOYSA-N 0.000 claims description 2
• GSWFTPYBBFIBTM-UHFFFAOYSA-N 2-[[2-[4-(dimethylamino)-4-phenylcyclohexyl]acetyl]amino]-3-(1h-indol-3-yl)propanoic acid;2-[4-(dimethylamino)-4-phenylcyclohexyl]-n-(1h-indol-3-ylmethyl)acetamide Chemical compound C1CC(CC(=O)NCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1.C1CC(CC(=O)NC(CC=2C3=CC=CC=C3NC=2)C(O)=O)CCC1(N(C)C)C1=CC=CC=C1 GSWFTPYBBFIBTM-UHFFFAOYSA-N 0.000 claims description 2
• 206010006895 Cachexia Diseases 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• 206010011878 Deafness Diseases 0.000 claims description 2
• 206010012335 Dependence Diseases 0.000 claims description 2
• 208000030814 Eating disease Diseases 0.000 claims description 2
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• 206010020772 Hypertension Diseases 0.000 claims description 2
• 208000001953 Hypotension Diseases 0.000 claims description 2
• 208000019695 Migraine disease Diseases 0.000 claims description 2
• 208000016285 Movement disease Diseases 0.000 claims description 2
• 208000003251 Pruritus Diseases 0.000 claims description 2
• 206010039966 Senile dementia Diseases 0.000 claims description 2
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
• 208000009205 Tinnitus Diseases 0.000 claims description 2
• 239000001961 anticonvulsive agent Substances 0.000 claims description 2
• 239000002249 anxiolytic agent Substances 0.000 claims description 2
• 208000010877 cognitive disease Diseases 0.000 claims description 2
• DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical class O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims description 2
• 235000014632 disordered eating Nutrition 0.000 claims description 2
• 239000002934 diuretic Substances 0.000 claims description 2
• 230000010370 hearing loss Effects 0.000 claims description 2
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• 230000036543 hypotension Effects 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
• 239000003158 myorelaxant agent Substances 0.000 claims description 2
• BBPOBTJKFXYUSK-UHFFFAOYSA-N n-benzyl-2-[4-(dimethylamino)-4-phenylcyclohexylidene]acetamide;hydrochloride Chemical compound Cl.C1CC(N(C)C)(C=2C=CC=CC=2)CCC1=CC(=O)NCC1=CC=CC=C1 BBPOBTJKFXYUSK-UHFFFAOYSA-N 0.000 claims description 2
• 239000000014 opioid analgesic Substances 0.000 claims description 2
• WVULZDFWPQCPPJ-UHFFFAOYSA-N potassium;hydrochloride Chemical compound Cl.[K] WVULZDFWPQCPPJ-UHFFFAOYSA-N 0.000 claims description 2
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• 208000011580 syndromic disease Diseases 0.000 claims description 2
• 231100000886 tinnitus Toxicity 0.000 claims description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
• KMLPEYHLAKSCGX-UHFFFAOYSA-N 2-aminocyclohexan-1-one Chemical class NC1CCCCC1=O KMLPEYHLAKSCGX-UHFFFAOYSA-N 0.000 claims 2
• 239000003193 general anesthetic agent Substances 0.000 claims 2
• 229910052697 platinum Inorganic materials 0.000 claims 2
• OLKQIWCQICCYQS-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(CC(N)=O)C=C1 OLKQIWCQICCYQS-UHFFFAOYSA-N 0.000 claims 1
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• 229940035363 muscle relaxants Drugs 0.000 claims 1
• 230000003957 neurotransmitter release Effects 0.000 claims 1
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• 230000009278 visceral effect Effects 0.000 claims 1
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
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• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 104
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• 239000002244 precipitate Substances 0.000 description 70
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 46
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
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• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 36
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