CA1055945A - Pharmaceutical compositions and method of producing antipsychotic activity without extrapyramidal symptoms - Google Patents
Pharmaceutical compositions and method of producing antipsychotic activity without extrapyramidal symptomsInfo
- Publication number
- CA1055945A CA1055945A CA238,781A CA238781A CA1055945A CA 1055945 A CA1055945 A CA 1055945A CA 238781 A CA238781 A CA 238781A CA 1055945 A CA1055945 A CA 1055945A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- hydrogen
- methyl
- formula
- mol
- 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
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000000561 anti-psychotic effect Effects 0.000 title abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 4
- 208000027776 Extrapyramidal disease Diseases 0.000 title description 6
- -1 piperidylidene Chemical class 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 10
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims abstract description 7
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 13
- 235000019260 propionic acid Nutrition 0.000 claims description 12
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- QUXRAOQDUJFWIA-UHFFFAOYSA-N 4-(2-chloroxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1CN(C)CCC1=C1C2=CC(Cl)=CC=C2OC2=CC=CC=C21 QUXRAOQDUJFWIA-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- VKOJCXWEBUNAGY-UHFFFAOYSA-N 2-chloro-9-(1-methylpiperidin-4-yl)xanthen-9-ol Chemical compound C1CN(C)CCC1C1(O)C2=CC(Cl)=CC=C2OC2=CC=CC=C21 VKOJCXWEBUNAGY-UHFFFAOYSA-N 0.000 claims description 2
- PRWJZNITVOUZBU-UHFFFAOYSA-N 2-chloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3OC2=C1 PRWJZNITVOUZBU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001347 alkyl bromides Chemical class 0.000 claims description 2
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 11
- 238000002360 preparation method Methods 0.000 claims 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 229960002337 magnesium chloride Drugs 0.000 claims 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- 235000011147 magnesium chloride Nutrition 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 9
- 241001465754 Metazoa Species 0.000 abstract description 5
- 208000024891 symptom Diseases 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 116
- 239000000243 solution Substances 0.000 description 69
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000284 extract Substances 0.000 description 20
- 229940076134 benzene Drugs 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007818 Grignard reagent Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 150000004795 grignard reagents Chemical class 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- QTOOYVGXYKLUNG-UHFFFAOYSA-N 4-(2-chloroxanthen-9-ylidene)piperidine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C1=C1CCNCC1 QTOOYVGXYKLUNG-UHFFFAOYSA-N 0.000 description 5
- 102000015554 Dopamine receptor Human genes 0.000 description 5
- 108050004812 Dopamine receptor Proteins 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000000164 antipsychotic agent Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 229960004365 benzoic acid Drugs 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 229940032330 sulfuric acid Drugs 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 description 4
- FQLSBXCEUFTIHI-UHFFFAOYSA-N 4-(2-chlorothioxanthen-9-ylidene)piperidine Chemical compound C12=CC(Cl)=CC=C2SC2=CC=CC=C2C1=C1CCNCC1 FQLSBXCEUFTIHI-UHFFFAOYSA-N 0.000 description 3
- IWNPWQRBFNOGHM-UHFFFAOYSA-N 9h-thioxanthen-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3SC2=C1 IWNPWQRBFNOGHM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940005529 antipsychotics Drugs 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 229960003638 dopamine Drugs 0.000 description 3
- 230000003291 dopaminomimetic effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- BQDNFXRLGVGWRP-UHFFFAOYSA-N 2,6-difluorothioxanthen-9-one Chemical compound C1=C(F)C=C2C(=O)C3=CC=C(F)C=C3SC2=C1 BQDNFXRLGVGWRP-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- YESXXPJHOUAICR-UHFFFAOYSA-N 3-fluorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(F)C=C3SC2=C1 YESXXPJHOUAICR-UHFFFAOYSA-N 0.000 description 2
- UHGZJXZINNENOT-UHFFFAOYSA-N 4-(2-bromothioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1CN(C)CCC1=C1C2=CC(Br)=CC=C2SC2=CC=CC=C21 UHGZJXZINNENOT-UHFFFAOYSA-N 0.000 description 2
- WTZPERAJKMXMSC-UHFFFAOYSA-N 4-(2-bromoxanthen-9-ylidene)piperidine Chemical compound C12=CC(Br)=CC=C2OC2=CC=CC=C2C1=C1CCNCC1 WTZPERAJKMXMSC-UHFFFAOYSA-N 0.000 description 2
- LNGGMSPZRSOIPB-UHFFFAOYSA-N 4-(2-chloroxanthen-9-ylidene)-1-(cyclobutylmethyl)piperidine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C1=C(CC1)CCN1CC1CCC1 LNGGMSPZRSOIPB-UHFFFAOYSA-N 0.000 description 2
- QDOJNWFOCOWAPO-UHFFFAOYSA-N 4-chloro-1-methylpiperidine;hydron;chloride Chemical compound Cl.CN1CCC(Cl)CC1 QDOJNWFOCOWAPO-UHFFFAOYSA-N 0.000 description 2
- VAVKIJNEVUPNQP-UHFFFAOYSA-N 9-(1-methylpiperidin-4-ylidene)xanthene-2-carbonitrile Chemical compound C1CN(C)CCC1=C1C2=CC(C#N)=CC=C2OC2=CC=CC=C21 VAVKIJNEVUPNQP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000012223 aqueous fraction Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 in position 9
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52121674A | 1974-11-06 | 1974-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055945A true CA1055945A (en) | 1979-06-05 |
Family
ID=24075868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,781A Expired CA1055945A (en) | 1974-11-06 | 1975-10-31 | Pharmaceutical compositions and method of producing antipsychotic activity without extrapyramidal symptoms |
Country Status (17)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2357251A1 (fr) * | 1976-07-09 | 1978-02-03 | Merck & Co Inc | 1-methyl-4-(2-carboxy-1-thioxanthan-9-ylidene)-piperidine |
| US4073912A (en) * | 1976-10-12 | 1978-02-14 | Smithkline Corporation | Piperidylidene derivatives of benzo-fused xanthenes, thioxanthenes and dibenzoxepins and antipsychotic use thereof |
| US4089961A (en) * | 1976-11-08 | 1978-05-16 | Smithkline Corporation | Antipsychotically useful quinolizidylidene derivatives of xanthenes, thioxanthenes and dibenzoxepins |
| NZ189108A (en) * | 1977-12-29 | 1982-02-23 | Kefalas As | 2-methylthio-6-fluoro-9-(1-methyl-4-piperidylidene)-thioxanthene and pharmaceutical compositions intermediate 2-methylthio-6-fluoro-9-(1-methyl-4-piperidyl)-thioxanthen-9-ol |
| US4777177A (en) * | 1984-10-19 | 1988-10-11 | Ciba-Geigy Corporation | Pesticidal thioxanthen-9-ylidenepiperidines |
| US5250681A (en) * | 1988-06-02 | 1993-10-05 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| CA2004211A1 (en) * | 1988-11-30 | 1990-05-31 | Masataka Syoji | Piperidine derivatives and hyportensives containing the same |
| EP1306376A1 (en) * | 2001-10-25 | 2003-05-02 | Biofrontera Pharmaceuticals AG | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist |
| US7060711B2 (en) | 2001-10-25 | 2006-06-13 | Biofrontera Bioscience Gmbh | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist |
| UA86024C2 (ru) | 2003-06-27 | 2009-03-25 | Янссен Фармацевтика Н.В. | Трициклические дельта-опиоидные модуляторы |
| KR20080027216A (ko) | 2004-08-05 | 2008-03-26 | 얀센 파마슈티카 엔.브이. | 트리사이클릭 δ-오피오이드 조절자 |
| CA2591963A1 (en) | 2004-12-22 | 2006-06-29 | Janssen Pharmaceutica N.V. | Tricyclic o-opioid modulators |
| US20060135522A1 (en) * | 2004-12-22 | 2006-06-22 | Carson John R | Tricyclic delta-opioid modulators |
| MX2007007627A (es) | 2004-12-22 | 2008-01-28 | Johnson & Johnson | Moduladores delta-opioides triciclicos. |
| KR20070104380A (ko) | 2005-01-06 | 2007-10-25 | 얀센 파마슈티카 엔.브이. | 트리사이클릭 δ-오피오이드 조절제 |
| BRPI0611885A2 (pt) | 2005-06-16 | 2010-10-05 | Janssen Pharmaceutica Nv | moduladores opióides tricìclicos |
| EP2067777B1 (en) * | 2006-09-29 | 2013-08-14 | Nippon Zoki Pharmaceutical Co., Ltd. | Oxepin derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260070A (enrdf_load_stackoverflow) * | 1960-02-25 | |||
| NL283292A (enrdf_load_stackoverflow) * | 1961-09-29 | |||
| DE1670118A1 (de) * | 1966-07-22 | 1970-11-05 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung neuer Derivate des 6,11-Dihydro-dibenz[b,e]oxepins und ihrer Salze |
| US3470188A (en) * | 1967-01-05 | 1969-09-30 | Smithkline Corp | 9-cycloalkyl-lower alkyl-piperidylidene derivatives of xanthenes and thioxanthenes |
| JPS5018478A (enrdf_load_stackoverflow) * | 1973-05-17 | 1975-02-26 |
-
1975
- 1975-10-16 ZA ZA00756550A patent/ZA756550B/xx unknown
- 1975-10-31 AU AU86247/75A patent/AU498298B2/en not_active Expired
- 1975-10-31 CA CA238,781A patent/CA1055945A/en not_active Expired
- 1975-11-02 IL IL48400A patent/IL48400A/xx unknown
- 1975-11-03 HU HU75SI1494A patent/HU174639B/hu not_active IP Right Cessation
- 1975-11-03 NZ NZ179139A patent/NZ179139A/xx unknown
- 1975-11-03 PH PH17733A patent/PH12158A/en unknown
- 1975-11-04 LU LU73714A patent/LU73714A1/xx unknown
- 1975-11-04 FR FR7533631A patent/FR2290202A1/fr active Granted
- 1975-11-04 DK DK495775AA patent/DK139429B/da not_active IP Right Cessation
- 1975-11-04 IE IE2398/75A patent/IE42137B1/en unknown
- 1975-11-04 BE BE161500A patent/BE835224A/xx not_active IP Right Cessation
- 1975-11-05 CH CH1432175A patent/CH624403A5/de not_active IP Right Cessation
- 1975-11-05 NL NL7512974A patent/NL7512974A/xx not_active Application Discontinuation
- 1975-11-05 JP JP50133564A patent/JPS5826754B2/ja not_active Expired
- 1975-11-05 ES ES442357A patent/ES442357A1/es not_active Expired
- 1975-11-06 DE DE19752549841 patent/DE2549841A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5170768A (enrdf_load_stackoverflow) | 1976-06-18 |
| IL48400A0 (en) | 1976-01-30 |
| CH624403A5 (en) | 1981-07-31 |
| AU8624775A (en) | 1977-05-05 |
| IE42137L (en) | 1976-05-06 |
| DK139429B (da) | 1979-02-19 |
| FR2290202B1 (enrdf_load_stackoverflow) | 1980-05-23 |
| ES442357A1 (es) | 1977-04-01 |
| DE2549841A1 (de) | 1976-05-13 |
| LU73714A1 (enrdf_load_stackoverflow) | 1976-06-11 |
| IE42137B1 (en) | 1980-06-04 |
| BE835224A (fr) | 1976-05-04 |
| AU498298B2 (en) | 1979-03-01 |
| ZA756550B (en) | 1976-09-29 |
| JPS5826754B2 (ja) | 1983-06-04 |
| HU174639B (hu) | 1980-02-28 |
| PH12158A (en) | 1978-11-10 |
| FR2290202A1 (fr) | 1976-06-04 |
| DK495775A (enrdf_load_stackoverflow) | 1976-05-07 |
| DK139429C (enrdf_load_stackoverflow) | 1979-08-06 |
| NL7512974A (nl) | 1976-05-10 |
| DE2549841C2 (enrdf_load_stackoverflow) | 1988-07-07 |
| IL48400A (en) | 1979-01-31 |
| NZ179139A (en) | 1978-04-28 |
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