CH387638A - Verfahren zur Herstellung von neuen heterocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Info

Publication number: CH387638A
Authority: CH; Switzerland
Prior art keywords: aza; methyl; solution; thioxanthene; evaporated
Prior art date: 1960-12-08

Application number

CH1375760A

Other languages

German (de)

English (en)

Inventor

Ernst Dr Jucker

Anton Dr Ebnoeter

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1960-12-08

Filing date

1960-12-08

Publication date

1965-02-15

1960-12-08 Application filed by Sandoz Ag filed Critical Sandoz Ag

1960-12-08 Priority to CH1375760A priority Critical patent/CH387638A/de

1961-11-13 Priority to GB4046361A priority patent/GB1003292A/en

1961-12-06 Priority to ES0272728A priority patent/ES272728A1/es

1961-12-06 Priority to LU40916A priority patent/LU40916A1/xx

1961-12-06 Priority to DES77010A priority patent/DE1206437B/de

1962-03-05 Priority to FR889949A priority patent/FR1884M/fr

1965-02-15 Publication of CH387638A publication Critical patent/CH387638A/de

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 7
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 27
VEOSCXKPFWPNIA-UHFFFAOYSA-N thiochromeno[2,3-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=N1 VEOSCXKPFWPNIA-UHFFFAOYSA-N 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
LLRRMBKLTKUJGB-UHFFFAOYSA-N OC1C(C=CC=N2)=C2SC2=CC=CC=C12 Chemical class OC1C(C=CC=N2)=C2SC2=CC=CC=C12 LLRRMBKLTKUJGB-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000002902 organometallic compounds Chemical class 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000155 melt Substances 0.000 description 23
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 22
229910000027 potassium carbonate Inorganic materials 0.000 description 19
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 11
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 11
235000019270 ammonium chloride Nutrition 0.000 description 9
239000002026 chloroform extract Substances 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
229910000861 Mg alloy Inorganic materials 0.000 description 8
OWXLRKWPEIAGAT-UHFFFAOYSA-N [Mg].[Cu] Chemical compound [Mg].[Cu] OWXLRKWPEIAGAT-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
-1 3-Methyl-9- (3'-dimethylamino-propyl) -4-aza-thioxanthene Chemical compound 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
238000001035 drying Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
239000001530 fumaric acid Substances 0.000 description 7
239000011777 magnesium Substances 0.000 description 7
230000007935 neutral effect Effects 0.000 description 7
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000005457 ice water Substances 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
TXNDOVAHWNZRSV-UHFFFAOYSA-N CC1=CC(=NC=2SC3=CC=CC=C3C(C1=2)=O)C Chemical compound CC1=CC(=NC=2SC3=CC=CC=C3C(C1=2)=O)C TXNDOVAHWNZRSV-UHFFFAOYSA-N 0.000 description 5
JZSJMIGEMMHFPG-UHFFFAOYSA-N CC=1C=CC=2C(C3=CC=CC=C3SC=2N=1)=CCCN(C)C Chemical compound CC=1C=CC=2C(C3=CC=CC=C3SC=2N=1)=CCCN(C)C JZSJMIGEMMHFPG-UHFFFAOYSA-N 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
NLHXVNXTYWYVGB-UHFFFAOYSA-N 2-methylthiochromeno[2,3-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)C3=CC=C(C)N=C3SC2=C1 NLHXVNXTYWYVGB-UHFFFAOYSA-N 0.000 description 4
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 4
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
RGLOUOVASVAHJD-UHFFFAOYSA-N CN(CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2)C Chemical compound CN(CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2)C RGLOUOVASVAHJD-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000011630 iodine Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
GAAYPTPSHXSMEM-UHFFFAOYSA-N 5h-thiochromeno[2,3-b]pyridine Chemical class C1=CC=C2CC3=CC=CC=C3SC2=N1 GAAYPTPSHXSMEM-UHFFFAOYSA-N 0.000 description 2
XHFRWZHWRQHZET-UHFFFAOYSA-N 6-methyl-2-phenylsulfanylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(SC=2C=CC=CC=2)=N1 XHFRWZHWRQHZET-UHFFFAOYSA-N 0.000 description 2
PXAZNIZKQUWSIY-UHFFFAOYSA-N CC(C=C1C2=CC=CC=C2SC=2N=CC=CC1=2)CN1CCCCC1 Chemical compound CC(C=C1C2=CC=CC=C2SC=2N=CC=CC1=2)CN1CCCCC1 PXAZNIZKQUWSIY-UHFFFAOYSA-N 0.000 description 2
KRILPCJHEFOBPO-UHFFFAOYSA-N CC1=CC(=NC=2SC3=CC=CC=C3C(C1=2)=CCCN(C)C)C Chemical compound CC1=CC(=NC=2SC3=CC=CC=C3C(C1=2)=CCCN(C)C)C KRILPCJHEFOBPO-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960003750 ethyl chloride Drugs 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
VEXKIOOWPFOHQI-UHFFFAOYSA-N 1-(3-chloro-2-methylpropyl)piperidine Chemical compound ClCC(C)CN1CCCCC1 VEXKIOOWPFOHQI-UHFFFAOYSA-N 0.000 description 1
AUERUDPETOKUPT-UHFFFAOYSA-N 1-(3-chloropropyl)-4-methylpiperazine Chemical compound CN1CCN(CCCCl)CC1 AUERUDPETOKUPT-UHFFFAOYSA-N 0.000 description 1
HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 1
SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 description 1
RETJKTAVEQPNMH-UHFFFAOYSA-N 2-chloro-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(Cl)=N1 RETJKTAVEQPNMH-UHFFFAOYSA-N 0.000 description 1
YSBNBAYNISAUIT-UHFFFAOYSA-N 2-chloro-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(Cl)=N1 YSBNBAYNISAUIT-UHFFFAOYSA-N 0.000 description 1
AKYKVQMXDAVSNN-UHFFFAOYSA-N 2-phenylsulfanylpyridine-3-carbonitrile Chemical class N#CC1=CC=CN=C1SC1=CC=CC=C1 AKYKVQMXDAVSNN-UHFFFAOYSA-N 0.000 description 1
QUQQIOJAMADCQH-UHFFFAOYSA-N 4,6-dimethyl-2-phenylsulfanylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SC=2C=CC=CC=2)=N1 QUQQIOJAMADCQH-UHFFFAOYSA-N 0.000 description 1
JFRADIZADCTHAS-UHFFFAOYSA-N 4,6-dimethyl-2-phenylsulfanylpyridine-3-carboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(SC=2C=CC=CC=2)=N1 JFRADIZADCTHAS-UHFFFAOYSA-N 0.000 description 1
PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 1
FMSFNNYIVOBMQX-UHFFFAOYSA-N 4-(3-thiochromeno[2,3-b]pyridin-5-ylidenepropyl)morpholine Chemical compound O1CCN(CC1)CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2 FMSFNNYIVOBMQX-UHFFFAOYSA-N 0.000 description 1
LZFNEUKCJNVRPI-UHFFFAOYSA-N 4-chloro-n,n-dimethylbutan-2-amine Chemical compound CN(C)C(C)CCCl LZFNEUKCJNVRPI-UHFFFAOYSA-N 0.000 description 1
VOUGRVOMTRTALH-UHFFFAOYSA-N 5-(3-pyrrolidin-1-ylpropylidene)thiochromeno[2,3-b]pyridine Chemical compound N1(CCCC1)CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2 VOUGRVOMTRTALH-UHFFFAOYSA-N 0.000 description 1
RJVUMWAHFPCWAB-UHFFFAOYSA-N 6-methyl-2-phenylsulfanylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SC=2C=CC=CC=2)=N1 RJVUMWAHFPCWAB-UHFFFAOYSA-N 0.000 description 1
IWNPWQRBFNOGHM-UHFFFAOYSA-N 9h-thioxanthen-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3SC2=C1 IWNPWQRBFNOGHM-UHFFFAOYSA-N 0.000 description 1
ZJKDRVIJAXHKNU-UHFFFAOYSA-N CC1=NC(=C(C(=C1S)C)C#N)C1=CC=CC=C1 Chemical compound CC1=NC(=C(C(=C1S)C)C#N)C1=CC=CC=C1 ZJKDRVIJAXHKNU-UHFFFAOYSA-N 0.000 description 1
ZLUPATAUKYGTRD-UHFFFAOYSA-N CN(C(CC=C1C2=CC=CC=C2SC=2N=CC=CC1=2)C)C Chemical compound CN(C(CC=C1C2=CC=CC=C2SC=2N=CC=CC1=2)C)C ZLUPATAUKYGTRD-UHFFFAOYSA-N 0.000 description 1
WAERFHZVEBCOBV-UHFFFAOYSA-N CN1CCN(CCC=C2C(C=CC=N3)=C3SC3=CC=CC=C23)CC1 Chemical compound CN1CCN(CCC=C2C(C=CC=N3)=C3SC3=CC=CC=C23)CC1 WAERFHZVEBCOBV-UHFFFAOYSA-N 0.000 description 1
RSKHVRQAEPYNLV-UHFFFAOYSA-N N1(CCCCC1)CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2 Chemical compound N1(CCCCC1)CCC=C1C2=CC=CC=C2SC=2N=CC=CC1=2 RSKHVRQAEPYNLV-UHFFFAOYSA-N 0.000 description 1
208000010513 Stupor Diseases 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1375760A 1960-12-08 1960-12-08 Verfahren zur Herstellung von neuen heterocyclischen Verbindungen CH387638A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH1375760A CH387638A (de)	1960-12-08	1960-12-08	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
GB4046361A GB1003292A (en)	1960-12-08	1961-11-13	Improvements in or relating to 4-azathiaxanthene derivatives
ES0272728A ES272728A1 (es)	1960-12-08	1961-12-06	Un procedimiento para la obtenciën de derivados de 4-aza-tiaxanteno
LU40916A LU40916A1 (fr)	1960-12-08	1961-12-06
DES77010A DE1206437B (de)	1960-12-08	1961-12-06	Verfahren zur Herstellung von neuen 4-Aza-thioxanthenderivaten
FR889949A FR1884M (fr)	1960-12-08	1962-03-05	Médicament a base de dérivé de l'aza-thiaxanthene.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1375760A CH387638A (de)	1960-12-08	1960-12-08	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH387638A true CH387638A (de)	1965-02-15

Family

ID=4395044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1375760A CH387638A (de)	1960-12-08	1960-12-08	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Country Status (2)

Country	Link
CH (1)	CH387638A (fr)
FR (1)	FR1884M (fr)

1960
- 1960-12-08 CH CH1375760A patent/CH387638A/de unknown
1962
- 1962-03-05 FR FR889949A patent/FR1884M/fr not_active Expired

Also Published As

Publication number	Publication date
FR1884M (fr)	1963-07-01

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DD161210A5 (de)	1985-06-12	Verfahren zur herstellung neuer 3-substituierter beta-carboline
DE1227026B (de)	1966-10-20	Verfahren zur Herstellung neuer heterocyclischer Benzocycloheptanderivate
CH621552A5 (fr)	1981-02-13
DE1206437B (de)	1965-12-09	Verfahren zur Herstellung von neuen 4-Aza-thioxanthenderivaten
DE1935404C3 (de)	1975-02-13	Verfahren zur Herstellung von Chinazoline nen
CH387638A (de)	1965-02-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
CH630904A5 (en)	1982-07-15	Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline.
AT230388B (de)	1963-12-10	Verfahren zur Herstellung von neuen 4-Aza-thioxanthen-Derivaten
CH498135A (de)	1970-10-31	Verfahren zur Herstellung von neuen Furazanderivaten
CH416624A (de)	1966-07-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
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AT228217B (de)	1963-07-10	Verfahren zur Herstellung von neuen Homothioxanthen-Derivaten
CH395087A (de)	1965-07-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT233552B (de)	1964-05-11	Verfahren zur Herstellung von neuen Dibenzocycloheptadien-Derivaten und ihren Salzen
AT220151B (de)	1962-03-12	Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazin-Derivaten
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AT230357B (de)	1963-12-10	Verfahren zur Herstellung von neuen Benzoesäurederivaten
CH383382A (de)	1964-10-31	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT244327B (de)	1965-12-27	Verfahren zur Herstellung von Diphenylalkylaminen und ihren physiologisch verträglichen Salzen
AT211001B (de)	1960-09-10	Verfahren zur Herstellung von neuen Scopin-äthern
AT227713B (de)	1963-06-10	Verfahren zur Herstellung von neuen 1,5-Diazacyclooctan-Derivaten
AT367404B (de)	1982-07-12	Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen