CA1081233A - 2-(4-phenyl-4-hydroxypiperidinomethyl) tetralone and indanone compounds - Google Patents
2-(4-phenyl-4-hydroxypiperidinomethyl) tetralone and indanone compoundsInfo
- Publication number
- CA1081233A CA1081233A CA246,346A CA246346A CA1081233A CA 1081233 A CA1081233 A CA 1081233A CA 246346 A CA246346 A CA 246346A CA 1081233 A CA1081233 A CA 1081233A
- Authority
- CA
- Canada
- Prior art keywords
- tetralone
- phenyl
- hydroxypiperidinomethyl
- dimethoxy
- compound
- Prior art date
- 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
Links
- ARIDMTPJRPNLIB-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CN(CC2C(C3=CC=CC=C3CC2)=O)CCC1(O)C1=CC=CC=C1 ARIDMTPJRPNLIB-UHFFFAOYSA-N 0.000 title claims description 5
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 title abstract description 14
- -1 methylenedioxy Chemical group 0.000 claims abstract description 142
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 239000002253 acid Substances 0.000 claims abstract description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 30
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 90
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
- 239000000126 substance Substances 0.000 claims description 39
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
- 235000019256 formaldehyde Nutrition 0.000 claims description 31
- 150000002576 ketones Chemical class 0.000 claims description 17
- SETKGOFWOWUIIE-UHFFFAOYSA-N 4-phenylpiperidin-4-ol;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(O)CCNCC1 SETKGOFWOWUIIE-UHFFFAOYSA-N 0.000 claims description 16
- YNNJHKOXXBIJKK-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=C1C=C(OC)C(OC)=C2 YNNJHKOXXBIJKK-UHFFFAOYSA-N 0.000 claims description 14
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 13
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- FRMMEKJKHWFUDP-UHFFFAOYSA-N 6-hydroxy-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC(O)=CC=C2C(=O)C1CN(CC1)CCC1(O)C1=CC=CC=C1 FRMMEKJKHWFUDP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 7
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 7
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims description 6
- YCJUUQFJPTYWKC-UHFFFAOYSA-N 6-amino-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC(N)=CC=C2C(=O)C1CN(CC1)CCC1(O)C1=CC=CC=C1 YCJUUQFJPTYWKC-UHFFFAOYSA-N 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- AFTZRHCIXHNGLZ-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydronaphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1(C)CN(CC1)CCC1(O)C1=CC=CC=C1 AFTZRHCIXHNGLZ-UHFFFAOYSA-N 0.000 claims description 5
- OEMZSJXPCJVMGB-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=CC=C1 OEMZSJXPCJVMGB-UHFFFAOYSA-N 0.000 claims description 5
- KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- ONYVDCPHPFXMHC-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1CN(CC1)CCC1(O)C1=CC=CC=C1 ONYVDCPHPFXMHC-UHFFFAOYSA-N 0.000 claims description 4
- MTYMCXXVJFQEFI-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=C(F)C=C1 MTYMCXXVJFQEFI-UHFFFAOYSA-N 0.000 claims description 4
- FNSQPQKPPGALFA-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(O)=CC=C21 FNSQPQKPPGALFA-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- IMLIMQXMQPZHPD-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CN(CC1)CCC1(O)C1=CC=CC=C1 IMLIMQXMQPZHPD-UHFFFAOYSA-N 0.000 claims description 3
- QPHIVVCRFKFOPV-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 QPHIVVCRFKFOPV-UHFFFAOYSA-N 0.000 claims description 3
- GUOHXLVJUXSHGJ-UHFFFAOYSA-N 2-[[4-[4-chloro-3-(trifluoromethyl)phenyl]-4-hydroxypiperidin-1-yl]methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GUOHXLVJUXSHGJ-UHFFFAOYSA-N 0.000 claims description 3
- XGCKQUFNKQVNKH-UHFFFAOYSA-N 2-[[4-hydroxy-4-(3-methylphenyl)piperidin-1-yl]methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=CC(C)=C1 XGCKQUFNKQVNKH-UHFFFAOYSA-N 0.000 claims description 3
- IHMQOBPGHZFGLC-UHFFFAOYSA-N 5,6-dimethoxy-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)CC2 IHMQOBPGHZFGLC-UHFFFAOYSA-N 0.000 claims description 3
- KFEWPHMCDHTBQJ-UHFFFAOYSA-N 6,7-dimethoxy-2-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(C)C(=O)C2=C1C=C(OC)C(OC)=C2 KFEWPHMCDHTBQJ-UHFFFAOYSA-N 0.000 claims description 3
- GJKXFMJSKSAUJU-UHFFFAOYSA-N 6-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-7,8-dihydro-6h-benzo[f][1,3]benzodioxol-5-one Chemical compound C1CN(CC2C(C3=CC=4OCOC=4C=C3CC2)=O)CCC1(O)C1=CC=CC=C1 GJKXFMJSKSAUJU-UHFFFAOYSA-N 0.000 claims description 3
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims description 3
- GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- KYKBFTOEYKVIJM-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methylidene]-6,7-dimethoxy-3,4-dihydronaphthalen-1-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CCC1=CN(CC1)CCC1(O)C1=CC=CC=C1 KYKBFTOEYKVIJM-UHFFFAOYSA-N 0.000 claims description 2
- UVJQAENQTZFEEP-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]butanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CCC(C(O)=O)CN1CCC(O)(C=2C=CC=CC=2)CC1 UVJQAENQTZFEEP-UHFFFAOYSA-N 0.000 claims description 2
- FPTKDIBNZLSEFE-UHFFFAOYSA-N 4-(4-methoxyphenyl)piperidin-4-ol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(O)CCNCC1 FPTKDIBNZLSEFE-UHFFFAOYSA-N 0.000 claims description 2
- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 claims description 2
- NTZLWARVWMHHEN-UHFFFAOYSA-N 7,8-dihydro-6h-benzo[f][1,3]benzodioxol-5-one Chemical compound C1=C2C(=O)CCCC2=CC2=C1OCO2 NTZLWARVWMHHEN-UHFFFAOYSA-N 0.000 claims description 2
- WEBCZGJWXXPNHB-UHFFFAOYSA-N N1-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide Chemical compound O=C1CCCC2=CC(NC(=O)C)=CC=C21 WEBCZGJWXXPNHB-UHFFFAOYSA-N 0.000 claims description 2
- RHQFGRBUNVVDCU-UHFFFAOYSA-N n-[7-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-8-oxo-6,7-dihydro-5h-naphthalen-2-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)C)=CC=C2CCC1CN(CC1)CCC1(O)C1=CC=CC=C1 RHQFGRBUNVVDCU-UHFFFAOYSA-N 0.000 claims description 2
- 229960004279 formaldehyde Drugs 0.000 claims 14
- IZTMGDCIDSIWSD-UHFFFAOYSA-N 6-chloro-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CN(CC2C(C3=CC=C(Cl)C=C3CC2)=O)CCC1(O)C1=CC=CC=C1 IZTMGDCIDSIWSD-UHFFFAOYSA-N 0.000 claims 2
- FXTSDOCCPWJSFM-UHFFFAOYSA-N n-[6-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-5-oxo-7,8-dihydro-6h-naphthalen-2-yl]acetamide Chemical compound C1CC2=CC(NC(=O)C)=CC=C2C(=O)C1CN(CC1)CCC1(O)C1=CC=CC=C1 FXTSDOCCPWJSFM-UHFFFAOYSA-N 0.000 claims 2
- VYMQQDMKDRBQNF-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1C2=CC(OC)=CC=C2CCC1CN(CC1)CCC1(O)C1=CC=CC=C1 VYMQQDMKDRBQNF-UHFFFAOYSA-N 0.000 claims 1
- ZRLALXNVPVEFQJ-UHFFFAOYSA-N 2-[[4-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl]methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC(OC)=CC=C1C1(O)CCN(CC2C(C3=CC(OC)=C(OC)C=C3CC2)=O)CC1 ZRLALXNVPVEFQJ-UHFFFAOYSA-N 0.000 claims 1
- AZOIKGWVSUTBDG-UHFFFAOYSA-N 4-(3-methylphenyl)piperidin-4-ol;hydrochloride Chemical compound Cl.CC1=CC=CC(C2(O)CCNCC2)=C1 AZOIKGWVSUTBDG-UHFFFAOYSA-N 0.000 claims 1
- PXAJMBHRLGKPQV-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidin-4-ol;hydron;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(O)CCNCC1 PXAJMBHRLGKPQV-UHFFFAOYSA-N 0.000 claims 1
- XWAMSNBDXDQRRN-UHFFFAOYSA-N 4-(4-fluorophenyl)piperidin-4-ol;hydrochloride Chemical compound Cl.C=1C=C(F)C=CC=1C1(O)CCNCC1 XWAMSNBDXDQRRN-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000003874 central nervous system depressant Substances 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 description 87
- 239000000203 mixture Substances 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 230000000875 corresponding effect Effects 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 229940093956 potassium carbonate Drugs 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- SVKJAGUIMGSZAS-UHFFFAOYSA-N 2,2-dimethoxy-3,4-dihydronaphthalen-1-one Chemical compound C1=CC=C2C(=O)C(OC)(OC)CCC2=C1 SVKJAGUIMGSZAS-UHFFFAOYSA-N 0.000 description 4
- ASYQUOQVACFLAE-UHFFFAOYSA-N 2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-6,7-dimethoxy-3,4-dihydro-2h-naphthalen-1-one;hydrochloride Chemical compound Cl.O=C1C=2C=C(OC)C(OC)=CC=2CCC1CN(CC1)CCC1(O)C1=CC=CC=C1 ASYQUOQVACFLAE-UHFFFAOYSA-N 0.000 description 4
- GANIBVZSZGNMNB-UHFFFAOYSA-N 2-methyl-1-tetralone Chemical compound C1=CC=C2C(=O)C(C)CCC2=C1 GANIBVZSZGNMNB-UHFFFAOYSA-N 0.000 description 4
- ITZDZUQOUDKGHH-UHFFFAOYSA-N 9,9a-dihydro-3ah-benzo[f][1,3]benzodioxol-4-one Chemical compound C1C2=CC=CC=C2C(=O)C2C1OCO2 ITZDZUQOUDKGHH-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229910003204 NH2 Inorganic materials 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- RVUXIPACAZKWHU-UHFFFAOYSA-N sulfuric acid;heptahydrate Chemical compound O.O.O.O.O.O.O.OS(O)(=O)=O RVUXIPACAZKWHU-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- XWVKTOHUMPLABF-UHFFFAOYSA-N thallium(3+) Chemical compound [Tl+3] XWVKTOHUMPLABF-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DWTTZBARDOXEAM-UHFFFAOYSA-N zearalenone Chemical compound O=C1OC(C)CCCC(O)CCCCCC2=CC(O)=CC(O)=C21 DWTTZBARDOXEAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507782 DE2507782A1 (de) | 1975-02-22 | 1975-02-22 | Tetralon- und indanon-derivate sowie verfahren zu ihrer herstellung |
| DE19752556196 DE2556196A1 (de) | 1975-12-13 | 1975-12-13 | Tetralon- und indanon-derivate sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081233A true CA1081233A (en) | 1980-07-08 |
Family
ID=25768542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,346A Expired CA1081233A (en) | 1975-02-22 | 1976-02-23 | 2-(4-phenyl-4-hydroxypiperidinomethyl) tetralone and indanone compounds |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4016281A (en, 2012) |
| JP (1) | JPS51110573A (en, 2012) |
| AT (1) | AT353270B (en, 2012) |
| CA (1) | CA1081233A (en, 2012) |
| CS (2) | CS190525B2 (en, 2012) |
| DD (1) | DD124977A5 (en, 2012) |
| DK (1) | DK72476A (en, 2012) |
| ES (1) | ES445367A1 (en, 2012) |
| FR (1) | FR2301253A1 (en, 2012) |
| GB (1) | GB1477293A (en, 2012) |
| HU (1) | HU173756B (en, 2012) |
| IE (1) | IE42486B1 (en, 2012) |
| IL (1) | IL49080A (en, 2012) |
| LU (1) | LU74390A1 (en, 2012) |
| NL (1) | NL7601762A (en, 2012) |
| SE (1) | SE7601962L (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2177085A (en) * | 1985-06-18 | 1987-01-14 | Ici Plc | Fungicidal compounds and compositions |
| WO1991012005A1 (en) * | 1990-02-06 | 1991-08-22 | Pfizer Inc. | Neuroprotective 3-piperidino-4-hydroxychroman derivatives and analogs |
| EP0535496A1 (en) * | 1991-09-25 | 1993-04-07 | Hoechst-Roussel Pharmaceuticals Incorporated | (1-Indanon-2yl)methylpiperidines, intermediates and a process for their preparation and their use as medicaments |
| DE4140542A1 (de) * | 1991-12-09 | 1993-06-17 | Bayer Ag | Piperdylmethyl substituierte chormanderivate |
| US5436255A (en) * | 1992-07-23 | 1995-07-25 | Pfizer Inc. | Method of treating diseases susceptable to treatment by blocking NMDA-receptors |
| WO1995020587A1 (en) * | 1994-01-31 | 1995-08-03 | Pfizer Inc. | Neuroprotective chroman compounds |
| CA2220649C (en) * | 1996-12-03 | 2007-02-13 | F. Hoffmann-La Roche Ag | 4-hydroxy-piperidine derivatives |
| JP2007523955A (ja) | 2004-02-25 | 2007-08-23 | ラ ホヤ ファーマシューティカル カンパニー | 疾患の治療のためのアミンおよびアミド |
| AU2005219785B2 (en) * | 2004-03-05 | 2010-05-27 | Msd K.K. | Cycloalkanopyridine derivative |
| CA2879589C (en) | 2012-07-27 | 2021-02-02 | Biogen Idec Ma Inc. | Compounds that are sip modulating agents and/or atx modulating agents |
| EP4074691A1 (en) | 2012-09-14 | 2022-10-19 | Supernus Pharmaceuticals, Inc. | Methods of producing molindone and its salts |
| CA3035999C (en) * | 2017-09-07 | 2021-01-05 | Syaulan S. YANG | Benzene fused heterocyclic derivatives and pharmaceutical composition comprising the same |
| CN115073435B (zh) * | 2022-06-24 | 2023-11-28 | 西北大学 | 一种检测硫化氢的近红外荧光探针及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
| GB1140990A (en) * | 1967-05-05 | 1969-01-22 | Warner Lambert Pharmaceutical | Novel 1,2,3,4-tetrahydro-naphthalen-2-ones and a process for the preparation thereof |
| US3547923A (en) * | 1968-03-25 | 1970-12-15 | Bristol Myers Co | Piperazyl ethyl 7h-benzocycloheptenes |
| US3644372A (en) * | 1970-01-14 | 1972-02-22 | Mcneilab Inc | 1-(4-piperidyl) indenes |
| US3850935A (en) * | 1971-10-16 | 1974-11-26 | Sumitomo Chemical Co | Process for producing piperidine derivatives by degrading quaternary piperidinium salts |
| US3974212A (en) * | 1974-05-22 | 1976-08-10 | Merck & Co., Inc. | [1-Hydroximino-2,2-disubstituted-5-indanyloxy-(or thio)]alkanoic acids |
-
1976
- 1976-02-18 US US05/659,132 patent/US4016281A/en not_active Expired - Lifetime
- 1976-02-19 CS CS761087A patent/CS190525B2/cs unknown
- 1976-02-19 SE SE7601962A patent/SE7601962L/xx unknown
- 1976-02-19 CS CS775289A patent/CS190549B2/cs unknown
- 1976-02-19 FR FR7604583A patent/FR2301253A1/fr active Granted
- 1976-02-20 GB GB686076A patent/GB1477293A/en not_active Expired
- 1976-02-20 HU HU76ME1952A patent/HU173756B/hu unknown
- 1976-02-20 AT AT124376A patent/AT353270B/de not_active IP Right Cessation
- 1976-02-20 DD DD191390A patent/DD124977A5/xx unknown
- 1976-02-20 DK DK72476*#A patent/DK72476A/da unknown
- 1976-02-20 IE IE340/76A patent/IE42486B1/en unknown
- 1976-02-20 LU LU74390A patent/LU74390A1/xx unknown
- 1976-02-20 ES ES445367A patent/ES445367A1/es not_active Expired
- 1976-02-20 NL NL7601762A patent/NL7601762A/xx not_active Application Discontinuation
- 1976-02-22 IL IL49080A patent/IL49080A/xx unknown
- 1976-02-23 JP JP51020544A patent/JPS51110573A/ja active Pending
- 1976-02-23 CA CA246,346A patent/CA1081233A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE42486B1 (en) | 1980-08-13 |
| DD124977A5 (en, 2012) | 1977-03-23 |
| US4016281A (en) | 1977-04-05 |
| IL49080A0 (en) | 1976-04-30 |
| NL7601762A (nl) | 1976-08-24 |
| HU173756B (hu) | 1979-08-28 |
| FR2301253A1 (fr) | 1976-09-17 |
| IE42486L (en) | 1976-08-22 |
| GB1477293A (en) | 1977-06-22 |
| LU74390A1 (en, 2012) | 1977-09-12 |
| ATA124376A (de) | 1979-04-15 |
| AT353270B (de) | 1979-11-12 |
| ES445367A1 (es) | 1977-10-01 |
| SE7601962L (sv) | 1976-08-23 |
| FR2301253B1 (en, 2012) | 1979-09-21 |
| IL49080A (en) | 1979-09-30 |
| JPS51110573A (en, 2012) | 1976-09-30 |
| CS190525B2 (en) | 1979-05-31 |
| CS190549B2 (en) | 1979-05-31 |
| DK72476A (da) | 1976-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |