DE2256392A1 - Verfahren zur herstellung neuer heterocyclischer verbindungen - Google Patents
Verfahren zur herstellung neuer heterocyclischer verbindungenInfo
- Publication number
- DE2256392A1 DE2256392A1 DE2256392A DE2256392A DE2256392A1 DE 2256392 A1 DE2256392 A1 DE 2256392A1 DE 2256392 A DE2256392 A DE 2256392A DE 2256392 A DE2256392 A DE 2256392A DE 2256392 A1 DE2256392 A1 DE 2256392A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- thioxanthene
- piperidylidene
- methyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000000354 decomposition reaction Methods 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- -1 methylsulfonyloxy Chemical group 0.000 description 12
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- SFCRDCSJCHFDTQ-UHFFFAOYSA-N 4-thioxanthen-9-ylidenepiperidine Chemical compound C1CNCCC1=C1C2=CC=CC=C2SC2=CC=CC=C21 SFCRDCSJCHFDTQ-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MAGOYBJJLVSJIC-UHFFFAOYSA-N 4-chlorobutan-2-one Chemical compound CC(=O)CCCl MAGOYBJJLVSJIC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- DVGQMOQMDYELSZ-UHFFFAOYSA-N C1CNCCC1=C2C3=C(C=C(C=C3)Cl)SC4=CC=CC=C42 Chemical compound C1CNCCC1=C2C3=C(C=C(C=C3)Cl)SC4=CC=CC=C42 DVGQMOQMDYELSZ-UHFFFAOYSA-N 0.000 description 2
- NHLMWOOQFVBUQQ-UHFFFAOYSA-N CC(C=C1)=CC2=C1SC1=CC=CC=C1C2=C1CCNCC1 Chemical compound CC(C=C1)=CC2=C1SC1=CC=CC=C1C2=C1CCNCC1 NHLMWOOQFVBUQQ-UHFFFAOYSA-N 0.000 description 2
- AUJMRGMSIJJVQH-UHFFFAOYSA-N CSC(C=C1)=CC2=C1SC1=CC=CC=C1C2=C1CCNCC1 Chemical compound CSC(C=C1)=CC2=C1SC1=CC=CC=C1C2=C1CCNCC1 AUJMRGMSIJJVQH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
- XUXWCNMKDZBRPM-UHFFFAOYSA-N 1-bromopentan-3-one Chemical compound CCC(=O)CCBr XUXWCNMKDZBRPM-UHFFFAOYSA-N 0.000 description 1
- FPANKUUAVASGAH-UHFFFAOYSA-N 1-methyl-4-(2-methylsulfanylthioxanthen-9-ylidene)piperidine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2C1=C1CCN(C)CC1 FPANKUUAVASGAH-UHFFFAOYSA-N 0.000 description 1
- QGKZTUNKIPEQMU-UHFFFAOYSA-N 1-methyl-4-(2-methylthioxanthen-9-ylidene)piperidine Chemical compound CN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC(=CC12)C QGKZTUNKIPEQMU-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- WEQVMIUSHABMEE-UHFFFAOYSA-N 2-methylsulfanylthioxanthen-9-one Chemical compound CSC1=CC=2C(C3=CC=CC=C3SC2C=C1)=O WEQVMIUSHABMEE-UHFFFAOYSA-N 0.000 description 1
- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 description 1
- WWUVXCZETRCYSN-UHFFFAOYSA-N 3-methyl-4-(4-thioxanthen-9-ylidenepiperidin-1-yl)butan-2-one Chemical compound CC(CN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC=CC12)C(C)=O WWUVXCZETRCYSN-UHFFFAOYSA-N 0.000 description 1
- ZMZMTFWTQURCFC-UHFFFAOYSA-N 3-methylbut-3-en-2-one pent-1-en-3-one Chemical compound CCC(=O)C=C.CC(=C)C(C)=O ZMZMTFWTQURCFC-UHFFFAOYSA-N 0.000 description 1
- BLGMFJSWCUYAKO-UHFFFAOYSA-N 4-(2-chlorothioxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1CN(C)CCC1=C1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 BLGMFJSWCUYAKO-UHFFFAOYSA-N 0.000 description 1
- MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
- PSSHLMPVDCMNKS-UHFFFAOYSA-N 4-chloro-3-methylbutan-2-one Chemical compound ClCC(C)C(C)=O PSSHLMPVDCMNKS-UHFFFAOYSA-N 0.000 description 1
- HTKABMPGOHRVCT-UHFFFAOYSA-N 5-bromopentan-2-one Chemical compound CC(=O)CCCBr HTKABMPGOHRVCT-UHFFFAOYSA-N 0.000 description 1
- LEJSXHLXJUILMI-UHFFFAOYSA-N 5-bromopentanal Chemical compound BrCCCCC=O LEJSXHLXJUILMI-UHFFFAOYSA-N 0.000 description 1
- CZGOECYPTLSLNI-UHFFFAOYSA-N 6-bromohexan-2-one Chemical compound CC(=O)CCCCBr CZGOECYPTLSLNI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- YPXAMSNSGWYQOY-UHFFFAOYSA-N C(#N)CCN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC=CC12 Chemical compound C(#N)CCN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC=CC12 YPXAMSNSGWYQOY-UHFFFAOYSA-N 0.000 description 1
- MNOZFAACDJKSMY-UHFFFAOYSA-N CN(CC1)CCC1C1(C(C=CC(Cl)=C2)=C2SC2=CC=CC=C12)O Chemical compound CN(CC1)CCC1C1(C(C=CC(Cl)=C2)=C2SC2=CC=CC=C12)O MNOZFAACDJKSMY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- JTLLMHHKWQFCMM-UHFFFAOYSA-N O=C(CCN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC=CC12)C Chemical compound O=C(CCN1CCC(CC1)=C1C2=CC=CC=C2SC=2C=CC=CC12)C JTLLMHHKWQFCMM-UHFFFAOYSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1695371A CH557379A (de) | 1971-11-22 | 1971-11-22 | Verfahren zur herstellung neuer 9-(4-piperidyliden)-thioxanthenderivate. |
| CH1695271A CH554893A (de) | 1971-11-22 | 1971-11-22 | Verfahren zur herstellung neuer 9-(4-piperidyliden)-thioxanthenderivate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2256392A1 true DE2256392A1 (de) | 1973-05-30 |
Family
ID=25718740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2256392A Pending DE2256392A1 (de) | 1971-11-22 | 1972-11-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS4862767A (pl) |
| AT (1) | ATA987272A (pl) |
| BE (1) | BE791699A (pl) |
| DD (1) | DD101575A5 (pl) |
| DE (1) | DE2256392A1 (pl) |
| DK (1) | DK130213B (pl) |
| FR (1) | FR2160940B1 (pl) |
| GB (1) | GB1409893A (pl) |
| HU (1) | HU164964B (pl) |
| NL (1) | NL7215570A (pl) |
| PL (1) | PL82440B1 (pl) |
| SE (1) | SE377940B (pl) |
| SU (1) | SU474981A3 (pl) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5283854A (en) * | 1976-01-01 | 1977-07-13 | Smithkline Corp | Piperidilidene derivatives of tricyclic compounds |
| US4356184A (en) * | 1980-06-04 | 1982-10-26 | G. D. Searle & Co. | Anti-allergic or antihypertensive 1-piperidinylmethyl benzenamines |
| US4609664A (en) * | 1980-09-02 | 1986-09-02 | Sandoz Ltd. | Antiasthmatic piperidylidene derivatives |
| US4777177A (en) * | 1984-10-19 | 1988-10-11 | Ciba-Geigy Corporation | Pesticidal thioxanthen-9-ylidenepiperidines |
| EP0371805A2 (en) * | 1988-11-30 | 1990-06-06 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| EP0451772A1 (en) * | 1990-04-11 | 1991-10-16 | Hokuriku Pharmaceutical Co., Ltd. | Piperidine compounds, method for preparation thereof, and a pharamceutical composition comprising the same |
| US5095022A (en) * | 1989-07-04 | 1992-03-10 | Hokuriku Pharmaceutical Co., Ltd. | Piperidine derivatives and pharmaceutical compositions comprising the same |
| US5250681A (en) * | 1988-06-02 | 1993-10-05 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| WO1999000376A1 (en) * | 1997-06-25 | 1999-01-07 | Novo Nordisk A/S | Novel heterocyclic compounds |
| WO2003035646A2 (en) * | 2001-10-25 | 2003-05-01 | Biofrontera Pharmaceuticals Gmbh | 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 |
| WO2014117863A1 (en) | 2013-02-01 | 2014-08-07 | Biofrontera Bioscience Gmbh | Salt polymorph of thioxanthene - 9 - ylidene - 1 - methyl piperidine acid addition salts as antimigraine compounds |
-
0
- BE BE791699D patent/BE791699A/xx unknown
-
1972
- 1972-11-13 DK DK563472AA patent/DK130213B/da unknown
- 1972-11-13 SE SE7214683A patent/SE377940B/xx unknown
- 1972-11-17 DE DE2256392A patent/DE2256392A1/de active Pending
- 1972-11-17 NL NL7215570A patent/NL7215570A/xx unknown
- 1972-11-20 DD DD166956A patent/DD101575A5/xx unknown
- 1972-11-20 GB GB5346172A patent/GB1409893A/en not_active Expired
- 1972-11-20 SU SU1848111A patent/SU474981A3/ru active
- 1972-11-20 PL PL1972158940A patent/PL82440B1/pl unknown
- 1972-11-21 AT AT987272A patent/ATA987272A/de not_active Application Discontinuation
- 1972-11-21 HU HUSA2421A patent/HU164964B/hu unknown
- 1972-11-21 JP JP47117063A patent/JPS4862767A/ja active Pending
- 1972-11-22 FR FR7241416A patent/FR2160940B1/fr not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5283854A (en) * | 1976-01-01 | 1977-07-13 | Smithkline Corp | Piperidilidene derivatives of tricyclic compounds |
| JPS6220190B2 (pl) * | 1976-01-01 | 1987-05-06 | ||
| US4356184A (en) * | 1980-06-04 | 1982-10-26 | G. D. Searle & Co. | Anti-allergic or antihypertensive 1-piperidinylmethyl benzenamines |
| US4609664A (en) * | 1980-09-02 | 1986-09-02 | Sandoz Ltd. | Antiasthmatic piperidylidene derivatives |
| 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 |
| EP0371805A2 (en) * | 1988-11-30 | 1990-06-06 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| EP0371805A3 (en) * | 1988-11-30 | 1991-07-31 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| US5095022A (en) * | 1989-07-04 | 1992-03-10 | Hokuriku Pharmaceutical Co., Ltd. | Piperidine derivatives and pharmaceutical compositions comprising the same |
| EP0451772A1 (en) * | 1990-04-11 | 1991-10-16 | Hokuriku Pharmaceutical Co., Ltd. | Piperidine compounds, method for preparation thereof, and a pharamceutical composition comprising the same |
| WO1999000376A1 (en) * | 1997-06-25 | 1999-01-07 | Novo Nordisk A/S | Novel heterocyclic compounds |
| US6054458A (en) * | 1997-06-25 | 2000-04-25 | Novonordiskals | Heterocyclic compounds |
| US6391890B1 (en) | 1997-06-25 | 2002-05-21 | Novo Nordisk A/S | Heterocyclic compounds |
| WO2003035646A2 (en) * | 2001-10-25 | 2003-05-01 | Biofrontera Pharmaceuticals Gmbh | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-ht2b receptor antagonist |
| 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 |
| WO2003035646A3 (en) * | 2001-10-25 | 2003-09-04 | Biofrontera Pharmaceuticals Gm | 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 |
| US7511064B2 (en) | 2001-10-25 | 2009-03-31 | Biofrontera Bioscience Gmbh | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist |
| WO2014117863A1 (en) | 2013-02-01 | 2014-08-07 | Biofrontera Bioscience Gmbh | Salt polymorph of thioxanthene - 9 - ylidene - 1 - methyl piperidine acid addition salts as antimigraine compounds |
| WO2014118307A1 (en) | 2013-02-01 | 2014-08-07 | Biofrontera Bioscience Gmbh | Salt polymorph of thioxanthene-9-ylidene-1-methyl piperidine acid addition salts as antimigraine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2160940B1 (pl) | 1976-05-21 |
| PL82440B1 (en) | 1975-10-31 |
| SE377940B (pl) | 1975-08-04 |
| NL7215570A (pl) | 1973-05-24 |
| FR2160940A1 (pl) | 1973-07-06 |
| ATA987272A (de) | 1976-02-15 |
| SU474981A3 (ru) | 1975-06-25 |
| JPS4862767A (pl) | 1973-09-01 |
| DK130213B (da) | 1975-01-20 |
| DD101575A5 (pl) | 1973-11-12 |
| GB1409893A (en) | 1975-10-15 |
| BE791699A (fr) | 1973-05-21 |
| HU164964B (pl) | 1974-05-28 |
| DK130213C (pl) | 1975-06-23 |
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