DE2504642A1 - Thioxanthenderivate - Google Patents
ThioxanthenderivateInfo
- Publication number
- DE2504642A1 DE2504642A1 DE19752504642 DE2504642A DE2504642A1 DE 2504642 A1 DE2504642 A1 DE 2504642A1 DE 19752504642 DE19752504642 DE 19752504642 DE 2504642 A DE2504642 A DE 2504642A DE 2504642 A1 DE2504642 A1 DE 2504642A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- stands
- thioxanthene
- derivatives according
- numbered
- 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.)
- Ceased
Links
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical class C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 title description 28
- -1 alkyl radical Chemical class 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- 150000005075 thioxanthenes Chemical class 0.000 claims description 31
- 229940054058 antipsychotic thioxanthene derivative Drugs 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 126
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 68
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000007858 starting material Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- 239000002904 solvent Substances 0.000 description 37
- 238000001953 recrystallisation Methods 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- 239000012458 free base Substances 0.000 description 10
- JPHMSZNWTDWBBV-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)thioxanthene Chemical compound C1=CC=C2C(CCCl)(CCCl)C3=CC=CC=C3SC2=C1 JPHMSZNWTDWBBV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000000730 antalgic agent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 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 5
- 239000005909 Kieselgur Substances 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000036407 pain Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 3
- ULMSDQBDGPQDOL-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)-2-methoxythioxanthene Chemical compound C1=CC=C2C(CCCl)(CCCl)C3=CC(OC)=CC=C3SC2=C1 ULMSDQBDGPQDOL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical group C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 2
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 2
- DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 2
- JTPYIPUTFBNGSV-UHFFFAOYSA-N 2-[2-chloro-5-methoxy-9-(2-methylsulfonyloxyethyl)thioxanthen-9-yl]ethyl methanesulfonate Chemical compound S1C2=CC=C(Cl)C=C2C(CCOS(C)(=O)=O)(CCOS(C)(=O)=O)C2=C1C(OC)=CC=C2 JTPYIPUTFBNGSV-UHFFFAOYSA-N 0.000 description 2
- CAKXNAPTBCQSHW-UHFFFAOYSA-N 2-[4-methoxy-9-(2-methylsulfonyloxyethyl)-10,10-dioxothioxanthen-9-yl]ethyl methanesulfonate Chemical compound COC1=CC=CC=2C(C3=CC=CC=C3S(C12)(=O)=O)(CCOS(=O)(=O)C)CCOS(=O)(=O)C CAKXNAPTBCQSHW-UHFFFAOYSA-N 0.000 description 2
- CHYPVBDXHSXKHF-UHFFFAOYSA-N 2-[4-methoxy-9-(2-methylsulfonyloxyethyl)thioxanthen-9-yl]ethyl methanesulfonate Chemical compound S1C2=CC=CC=C2C(CCOS(C)(=O)=O)(CCOS(C)(=O)=O)C2=C1C(OC)=CC=C2 CHYPVBDXHSXKHF-UHFFFAOYSA-N 0.000 description 2
- XESHDWNFUWDUKQ-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)-4-methoxythioxanthen-9-yl]ethanol Chemical compound S1C2=CC=CC=C2C(CCO)(CCO)C2=C1C(OC)=CC=C2 XESHDWNFUWDUKQ-UHFFFAOYSA-N 0.000 description 2
- WYHOKKWLRAFKPS-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)thioxanthen-9-yl]ethanol Chemical compound C1=CC=C2C(CCO)(CCO)C3=CC=CC=C3SC2=C1 WYHOKKWLRAFKPS-UHFFFAOYSA-N 0.000 description 2
- FKFGRZSANDYMPZ-UHFFFAOYSA-N 2-chloro-5-methoxy-9h-thioxanthene Chemical compound C1C2=CC(Cl)=CC=C2SC2=C1C=CC=C2OC FKFGRZSANDYMPZ-UHFFFAOYSA-N 0.000 description 2
- KLDHUTXMLSAMDH-UHFFFAOYSA-N 2-chloro-5-methoxythioxanthen-9-one Chemical compound S1C2=CC=C(Cl)C=C2C(=O)C2=C1C(OC)=CC=C2 KLDHUTXMLSAMDH-UHFFFAOYSA-N 0.000 description 2
- NUTGFDCMKRVDCQ-UHFFFAOYSA-N 2-chloro-9,9-bis(2-chloroethyl)thioxanthene Chemical compound C1=C(Cl)C=C2C(CCCl)(CCCl)C3=CC=CC=C3SC2=C1 NUTGFDCMKRVDCQ-UHFFFAOYSA-N 0.000 description 2
- WBSONQUHDWJABP-UHFFFAOYSA-N 2-ethoxybenzenethiol Chemical compound CCOC1=CC=CC=C1S WBSONQUHDWJABP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 2
- RSMPOQWKMPLRCD-UHFFFAOYSA-N 4-ethoxy-9h-thioxanthene Chemical compound C1C2=CC=CC=C2SC2=C1C=CC=C2OCC RSMPOQWKMPLRCD-UHFFFAOYSA-N 0.000 description 2
- MSFMTPYKTDYRLL-UHFFFAOYSA-N 4-methoxy-9h-thioxanthene Chemical compound C1C2=CC=CC=C2SC2=C1C=CC=C2OC MSFMTPYKTDYRLL-UHFFFAOYSA-N 0.000 description 2
- AGPAIXWLJCMPQQ-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)-2-methoxythioxanthene 10,10-dioxide Chemical compound COC1=CC=2C(C3=CC=CC=C3S(C2C=C1)(=O)=O)(CCCl)CCCl AGPAIXWLJCMPQQ-UHFFFAOYSA-N 0.000 description 2
- YJYRERBABGXVTJ-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)-4-methoxythioxanthene Chemical compound S1C2=CC=CC=C2C(CCCl)(CCCl)C2=C1C(OC)=CC=C2 YJYRERBABGXVTJ-UHFFFAOYSA-N 0.000 description 2
- PKICNJBYRWRABI-UHFFFAOYSA-N 9h-thioxanthene 10-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3CC2=C1 PKICNJBYRWRABI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- SVFCCLMUSXAPGS-UHFFFAOYSA-N 1,6-dichlorocyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1(Cl)C=CC=CC1Cl SVFCCLMUSXAPGS-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- NYLRZHUPZRKCRU-UHFFFAOYSA-N 1-ethyl-4'-methoxyspiro[piperidine-4,9'-thioxanthene] Chemical compound C1CN(CC)CCC21C1=CC=CC(OC)=C1SC1=CC=CC=C12 NYLRZHUPZRKCRU-UHFFFAOYSA-N 0.000 description 1
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 1
- IGXZYMIHYTUOMW-UHFFFAOYSA-N 1-methyl-9h-thioxanthene Chemical compound S1C2=CC=CC=C2CC2=C1C=CC=C2C IGXZYMIHYTUOMW-UHFFFAOYSA-N 0.000 description 1
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OHCUWKGXKOCTTQ-UHFFFAOYSA-N 2-[4-ethoxy-9-(2-hydroxyethyl)thioxanthen-9-yl]ethanol Chemical compound S1C2=CC=CC=C2C(CCO)(CCO)C2=C1C(OCC)=CC=C2 OHCUWKGXKOCTTQ-UHFFFAOYSA-N 0.000 description 1
- VDJUBKFSJSUUGX-UHFFFAOYSA-N 2-[4-methoxy-9-(2-methylsulfonyloxyethyl)-10-oxothioxanthen-9-yl]ethyl methanesulfonate Chemical compound COC1=CC=CC=2C(C3=CC=CC=C3S(C12)=O)(CCOS(=O)(=O)C)CCOS(=O)(=O)C VDJUBKFSJSUUGX-UHFFFAOYSA-N 0.000 description 1
- WSBAJEUGQRCSIO-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)-4,5-dimethoxythioxanthen-9-yl]ethanol Chemical compound S1C2=C(OC)C=CC=C2C(CCO)(CCO)C2=C1C(OC)=CC=C2 WSBAJEUGQRCSIO-UHFFFAOYSA-N 0.000 description 1
- VIUDWLLKFANPLX-UHFFFAOYSA-N 2-chloro-3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1Cl VIUDWLLKFANPLX-UHFFFAOYSA-N 0.000 description 1
- HRJYGQAACVZSEO-UHFFFAOYSA-N 2-chloro-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(Cl)=CC=C3SC2=C1 HRJYGQAACVZSEO-UHFFFAOYSA-N 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
- NQOPVGQHAYUKIV-UHFFFAOYSA-N 2-methoxy-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(OC)=CC=C3SC2=C1 NQOPVGQHAYUKIV-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- XZYRZHIEZKLINJ-UHFFFAOYSA-N 3-chloro-5-methoxy-9h-thioxanthene Chemical compound C1C2=CC=C(Cl)C=C2SC2=C1C=CC=C2OC XZYRZHIEZKLINJ-UHFFFAOYSA-N 0.000 description 1
- NAKKEMTXCKDSDI-UHFFFAOYSA-N 3-chloro-5-methoxythioxanthen-9-one Chemical compound S1C2=CC(Cl)=CC=C2C(=O)C2=C1C(OC)=CC=C2 NAKKEMTXCKDSDI-UHFFFAOYSA-N 0.000 description 1
- JBQXEYMKQKZVRB-UHFFFAOYSA-N 3-chloro-9,9-bis(2-ethenoxyethyl)-5-methoxythioxanthene Chemical compound S1C2=CC(Cl)=CC=C2C(CCOC=C)(CCOC=C)C2=C1C(OC)=CC=C2 JBQXEYMKQKZVRB-UHFFFAOYSA-N 0.000 description 1
- IORZOFVFRFBINJ-UHFFFAOYSA-N 4',5'-dimethoxy-1-methylspiro[piperidine-4,9'-thioxanthene] Chemical compound COC1=CC=CC2=C1SC1=C(OC)C=CC=C1C21CCN(C)CC1 IORZOFVFRFBINJ-UHFFFAOYSA-N 0.000 description 1
- YOOWGKAKZXQJAO-UHFFFAOYSA-N 4'-methoxyspiro[piperidine-4,9'-thioxanthene] Chemical compound COC1=CC=CC2=C1SC1=CC=CC=C1C21CCNCC1 YOOWGKAKZXQJAO-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- YIMUXKATVXWOKZ-UHFFFAOYSA-N 4,5-dimethoxy-9h-thioxanthene Chemical compound C1C2=CC=CC(OC)=C2SC2=C1C=CC=C2OC YIMUXKATVXWOKZ-UHFFFAOYSA-N 0.000 description 1
- OYHNDIHTUBCSQH-UHFFFAOYSA-N 4,5-dimethoxythioxanthen-9-one Chemical compound S1C2=C(OC)C=CC=C2C(=O)C2=C1C(OC)=CC=C2 OYHNDIHTUBCSQH-UHFFFAOYSA-N 0.000 description 1
- VQUCLGDFSOVFCY-UHFFFAOYSA-N 4-ethoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCC)=CC=C2 VQUCLGDFSOVFCY-UHFFFAOYSA-N 0.000 description 1
- BIISVKQUIUNQLJ-UHFFFAOYSA-N 4-methoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OC)=CC=C2 BIISVKQUIUNQLJ-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 1
- QUHGAFLHWIAIMP-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)-4-ethoxythioxanthene Chemical compound S1C2=CC=CC=C2C(CCCl)(CCCl)C2=C1C(OCC)=CC=C2 QUHGAFLHWIAIMP-UHFFFAOYSA-N 0.000 description 1
- ZRVPTRRJMYXVMY-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)thioxanthene 10,10-dioxide Chemical compound ClCCC1(C2=CC=CC=C2S(C=2C=CC=CC12)(=O)=O)CCCl ZRVPTRRJMYXVMY-UHFFFAOYSA-N 0.000 description 1
- QUNWRNYKBRFMDS-UHFFFAOYSA-N 9,9-bis(2-chloroethyl)thioxanthene 10-oxide Chemical compound C1=CC=C2C(CCCl)(CCCl)C3=CC=CC=C3S(=O)C2=C1 QUNWRNYKBRFMDS-UHFFFAOYSA-N 0.000 description 1
- LLTAWCZPDRWIQP-UHFFFAOYSA-N 9,9-bis(2-ethenoxyethyl)-2-methoxythioxanthene Chemical compound C1=CC=C2C(CCOC=C)(CCOC=C)C3=CC(OC)=CC=C3SC2=C1 LLTAWCZPDRWIQP-UHFFFAOYSA-N 0.000 description 1
- DEQUIOSYLVRICX-UHFFFAOYSA-N 9,9-bis(2-ethenoxyethyl)-4,5-dimethoxythioxanthene Chemical compound S1C2=C(OC)C=CC=C2C(CCOC=C)(CCOC=C)C2=C1C(OC)=CC=C2 DEQUIOSYLVRICX-UHFFFAOYSA-N 0.000 description 1
- XUAWDHIXOWAPPU-UHFFFAOYSA-N 9,9-bis(2-ethenoxyethyl)-4-methoxythioxanthene Chemical compound S1C2=CC=CC=C2C(CCOC=C)(CCOC=C)C2=C1C(OC)=CC=C2 XUAWDHIXOWAPPU-UHFFFAOYSA-N 0.000 description 1
- HMSIEEKYRXCWDI-UHFFFAOYSA-N 9,9-bis(2-ethenoxyethyl)thioxanthene Chemical compound C1=CC=C2C(CCOC=C)(CCOC=C)C3=CC=CC=C3SC2=C1 HMSIEEKYRXCWDI-UHFFFAOYSA-N 0.000 description 1
- XEIVFUWZYMWLEP-UHFFFAOYSA-N 9h-thioxanthene 10,10-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3CC2=C1 XEIVFUWZYMWLEP-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- USQOVYLRWBOSQC-HNNXBMFYSA-N CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O Chemical compound CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O USQOVYLRWBOSQC-HNNXBMFYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- JOWUFBFSUXFACX-UHFFFAOYSA-N Cl.C1CC2(C3=CC=CC=C3SC3=CC=CC=C32)CCN1CC1=CC=CC=C1 Chemical compound Cl.C1CC2(C3=CC=CC=C3SC3=CC=CC=C32)CCN1CC1=CC=CC=C1 JOWUFBFSUXFACX-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 241000581650 Ivesia Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JCBIZJXRBGOIIV-UHFFFAOYSA-N OC(=O)CC(O)(C(O)=O)CC(O)=O.C1CN(C)CCC21C1=CC=CC=C1SC1=CC=CC=C12 Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1CN(C)CCC21C1=CC=CC=C1SC1=CC=CC=C12 JCBIZJXRBGOIIV-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ODUIXUGXPFKQLG-QWRGUYRKSA-N [2-(4-chloro-2-fluoroanilino)-5-methyl-1,3-thiazol-4-yl]-[(2s,3s)-2,3-dimethylpiperidin-1-yl]methanone Chemical compound C[C@H]1[C@@H](C)CCCN1C(=O)C1=C(C)SC(NC=2C(=CC(Cl)=CC=2)F)=N1 ODUIXUGXPFKQLG-QWRGUYRKSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229960001301 amobarbital Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- 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 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 1
- YYRHJONEDNAHJV-UHFFFAOYSA-N cyclobutyl-(4'-methoxyspiro[piperidine-4,9'-thioxanthene]-1-yl)methanone Chemical compound COC1=CC=CC2=C1SC1=CC=CC=C1C2(CC1)CCN1C(=O)C1CCC1 YYRHJONEDNAHJV-UHFFFAOYSA-N 0.000 description 1
- HXSNGAHNYZBZTH-UHFFFAOYSA-N cyclopropylmethanamine;hydrochloride Chemical compound Cl.NCC1CC1 HXSNGAHNYZBZTH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 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 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- YBXBWBBVLXZQBJ-UHFFFAOYSA-N n-[2-(5-hydroxy-2-methyl-1h-indol-3-yl)ethyl]-2-methoxyacetamide Chemical compound C1=C(O)C=C2C(CCNC(=O)COC)=C(C)NC2=C1 YBXBWBBVLXZQBJ-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000004084 narcotic analgesic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- OMWCQLQQBWHBSL-UHFFFAOYSA-N spiro[piperidine-4,9'-thioxanthene] sulfuric acid hydrate Chemical compound O.OS(O)(=O)=O.C1CNCCC21C1=CC=CC=C1SC1=CC=CC=C12 OMWCQLQQBWHBSL-UHFFFAOYSA-N 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
- 229960002324 trifluoperazine Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB501774A GB1434486A (en) | 1974-02-04 | 1974-02-04 | Thioxanthene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2504642A1 true DE2504642A1 (de) | 1975-08-07 |
Family
ID=9788187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504642 Ceased DE2504642A1 (de) | 1974-02-04 | 1975-02-04 | Thioxanthenderivate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4001418A (en, 2012) |
| JP (1) | JPS50112375A (en, 2012) |
| BE (1) | BE825130A (en, 2012) |
| DE (1) | DE2504642A1 (en, 2012) |
| DK (1) | DK37775A (en, 2012) |
| FR (1) | FR2259607B1 (en, 2012) |
| GB (1) | GB1434486A (en, 2012) |
| IE (1) | IE40352B1 (en, 2012) |
| LU (1) | LU71790A1 (en, 2012) |
| NL (1) | NL7501232A (en, 2012) |
| SE (2) | SE7501160L (en, 2012) |
| ZA (1) | ZA75166B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013424A1 (de) * | 1979-01-10 | 1980-07-23 | Hoechst Aktiengesellschaft | Spiro(dibenz(b,f)thiepin-piperidine), Zwischenprodukte zu ihrer Herstellung und sie enthaltende Arzneimittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198418A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Spiro[dibenz(b,f)oxepin-piperidine]s |
| GB8529448D0 (en) * | 1985-11-29 | 1986-01-08 | Ward Blenkinsop & Co Ltd | Thioxanthone derivatives |
| US7014925B2 (en) * | 2003-04-29 | 2006-03-21 | Canon Kabushiki Kaisha | Heterogeneous spiro compounds in organic light emitting device elements |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2368006A (en) * | 1943-10-07 | 1945-01-23 | Searle & Co | Heterocyclic tertiary amines |
| US3048595A (en) * | 1960-11-14 | 1962-08-07 | Smith Kline French Lab | Spiro derivatives of thiazanthenes and xanthenes |
| NL122808C (en, 2012) * | 1961-09-29 | |||
| NL301204A (en, 2012) * | 1962-12-07 | |||
| US3470188A (en) * | 1967-01-05 | 1969-09-30 | Smithkline Corp | 9-cycloalkyl-lower alkyl-piperidylidene derivatives of xanthenes and thioxanthenes |
| BE758919A (fr) * | 1969-11-15 | 1971-05-13 | Merck Patent Gmbh | Spiro-composes |
-
1974
- 1974-02-04 GB GB501774A patent/GB1434486A/en not_active Expired
-
1975
- 1975-01-07 IE IE34/75A patent/IE40352B1/xx unknown
- 1975-01-09 US US05/539,627 patent/US4001418A/en not_active Expired - Lifetime
- 1975-01-09 ZA ZA00750166A patent/ZA75166B/xx unknown
- 1975-02-03 LU LU71790A patent/LU71790A1/xx unknown
- 1975-02-03 FR FR7503264A patent/FR2259607B1/fr not_active Expired
- 1975-02-03 BE BE153013A patent/BE825130A/xx unknown
- 1975-02-03 NL NL7501232A patent/NL7501232A/xx unknown
- 1975-02-04 DK DK37775*#A patent/DK37775A/da unknown
- 1975-02-04 DE DE19752504642 patent/DE2504642A1/de not_active Ceased
- 1975-02-04 JP JP50014764A patent/JPS50112375A/ja active Pending
- 1975-06-05 SE SE7501160A patent/SE7501160L/xx unknown
-
1978
- 1978-01-11 SE SE7800301A patent/SE7800301L/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013424A1 (de) * | 1979-01-10 | 1980-07-23 | Hoechst Aktiengesellschaft | Spiro(dibenz(b,f)thiepin-piperidine), Zwischenprodukte zu ihrer Herstellung und sie enthaltende Arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7501232A (nl) | 1975-08-06 |
| FR2259607B1 (en, 2012) | 1980-01-25 |
| LU71790A1 (en, 2012) | 1976-08-19 |
| FR2259607A1 (en, 2012) | 1975-08-29 |
| SE7501160L (en, 2012) | 1975-08-05 |
| IE40352L (en) | 1975-08-04 |
| BE825130A (fr) | 1975-08-04 |
| JPS50112375A (en, 2012) | 1975-09-03 |
| GB1434486A (en) | 1976-05-05 |
| US4001418A (en) | 1977-01-04 |
| ZA75166B (en) | 1976-01-28 |
| DK37775A (en, 2012) | 1975-09-29 |
| SE7800301L (sv) | 1978-01-11 |
| AU7725475A (en) | 1976-07-15 |
| IE40352B1 (en) | 1979-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1795769C3 (de) | 6,7,8,9-Tetrahydro-2H-pyrido [Ua] pyrimidinderivate, deren Salze mit Säuren und quaternäre Methosalze, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| DE69006799T2 (de) | Spirocyclische antipsychotische Mittel. | |
| DE2819210A1 (de) | 4-aminomethyl-1-(3,3,3-triarylpropyl)-4-arylpiperidin und dessen derivate | |
| DE1695836A1 (de) | Substituierte Piperidinoalkylthianaphthene und -benzofurane | |
| DE69013602T2 (de) | Arzneimittel. | |
| DE3402060A1 (de) | Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2616616A1 (de) | 1-(triarylalklyl)-4-phenylpiperidinderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die diese verbindungen enthalten | |
| DE2504643A1 (de) | Xanthenderivate | |
| DE2504642A1 (de) | Thioxanthenderivate | |
| DE2617955A1 (de) | Neue l-substituierte -aroyl-4-hydroxypiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| EP1335720A1 (de) | Sulfonamiden zur behandlung von erkrankungen des zentralen nervensystems | |
| DE2106694C2 (de) | Phthalimidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1695416A1 (de) | Benzomorphan-derivate und Verfahren zu deren Herstellung | |
| DE2847623C2 (de) | 4-Amino-2-(piperazin-1-yl oder homopiperazin-1-yl)-chinazolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2822465A1 (de) | Trans-2-substituierte-5-aryl- 2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu -indolderivate und diese enthaltende arzneimittel | |
| DE2804519A1 (de) | Oxadiazolopyrimidin-derivate | |
| DE69029861T2 (de) | N-acyl-substituierte azazyklische verbindungen, verfahren zu deren herstellung und deren verwendung als arzneimittel | |
| DE2630602A1 (de) | 1,3,8-triazaspiro eckige klammer auf 4.5 eckige klammer zu decan-4-on- derivate | |
| DE2051962A1 (de) | Benzimidazo eckige Klammer auf l,2d eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin 6 (5H) one und Verfahren zu deren Her stellung | |
| DE3204153A1 (de) | Substituierte thienobenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2624352B2 (de) | Dibenzo ecklige Klammer auf b,f] thiepine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende entzündungshemmende Zubereitungen | |
| DD151751A5 (de) | Verfahren zur herstellung von schwefelhaltigen isochinolinderivaten | |
| DE1745783A1 (de) | Neue Isochinoline gegen Viren | |
| DE2836449A1 (de) | 2,3-polymethylen-4-oxo-4h-pyrido (1,2-a) pyrimidine und ein verfahren zur herstellung derselben | |
| DE2051961A1 (de) | 6 substituierte Indol eckige Klammer auf 1,2 c eckige Klammer zu chinazoline und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |