CH405354A - Verfahren zur Herstellung von neuen heterocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Info

Publication number: CH405354A
Authority: CH; Switzerland
Prior art keywords: thieno; benzothiopyran; methyl; ccm; hydroxy
Prior art date: 1961-04-26

Application number

CH489061A

Other languages

German (de)

English (en)

Inventor

Jany Dr Renz

Jean-Pierre Dr Bourquin

Schwarb Gustav

Ruesch Leo

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.)

1961-04-26

Filing date

1961-04-26

Publication date

1966-01-15

1961-04-26 Application filed by Sandoz Ag filed Critical Sandoz Ag

1961-04-26 Priority to CH489061A priority Critical patent/CH405354A/de

1962-04-17 Priority to GB14952/62A priority patent/GB1012313A/en

1962-04-25 Priority to DK187062AA priority patent/DK103516C/da

1962-04-26 Priority to AT342362A priority patent/AT240359B/de

1962-07-23 Priority to FR904796A priority patent/FR1947M/fr

1962-07-23 Priority to FR904797A priority patent/FR1948M/fr

1966-01-15 Publication of CH405354A publication Critical patent/CH405354A/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 14
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 94
ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical class C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 description 70
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 25
238000002844 melting Methods 0.000 description 24
230000008018 melting Effects 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000002585 base Substances 0.000 description 21
-1 for example Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 19
238000001704 evaporation Methods 0.000 description 18
230000008020 evaporation Effects 0.000 description 18
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
238000003756 stirring Methods 0.000 description 12
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 10
229940040526 anhydrous sodium acetate Drugs 0.000 description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
238000010992 reflux Methods 0.000 description 9
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
239000011976 maleic acid Substances 0.000 description 8
239000000155 melt Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000011777 magnesium Substances 0.000 description 7
229910052749 magnesium Inorganic materials 0.000 description 7
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000011630 iodine Substances 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
235000002906 tartaric acid Nutrition 0.000 description 6
239000011975 tartaric acid Substances 0.000 description 6
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
SWEDAZLCYJDAGW-UHFFFAOYSA-N Thiophene-2-thiol Chemical compound SC1=CC=CS1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229940095064 tartrate Drugs 0.000 description 5
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000002901 organomagnesium compounds Chemical class 0.000 description 4
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
AFMGAVDATRJOJG-GUYCJALGSA-N (3s,5s)-3-methyl-5-[(4-phenylphenyl)methyl]pyrrolidin-2-one Chemical compound N1C(=O)[C@@H](C)C[C@H]1CC1=CC=C(C=2C=CC=CC=2)C=C1 AFMGAVDATRJOJG-GUYCJALGSA-N 0.000 description 3
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
RBCPJQQJBAQSOU-UHFFFAOYSA-N 2-bromo-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Br RBCPJQQJBAQSOU-UHFFFAOYSA-N 0.000 description 2
XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical group OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 2
KGRZUMDCDMVCGW-UHFFFAOYSA-N 5-chloro-2-thiophen-2-ylsulfanylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1SC1=CC=CS1 KGRZUMDCDMVCGW-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229940072033 potash Drugs 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
CXKZLZFCUJDIEP-UHFFFAOYSA-N thieno[2,3-b]thiochromen-4-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1SC=C2 CXKZLZFCUJDIEP-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ODHJOROUCITYNF-UHFFFAOYSA-N 2-bromo-5-methoxybenzoic acid Chemical compound COC1=CC=C(Br)C(C(O)=O)=C1 ODHJOROUCITYNF-UHFFFAOYSA-N 0.000 description 1
WJGFDDCMTMHZMN-UHFFFAOYSA-N 2-bromo-5-methylsulfanylbenzoic acid Chemical compound CSC1=CC=C(Br)C(C(O)=O)=C1 WJGFDDCMTMHZMN-UHFFFAOYSA-N 0.000 description 1
RTXOJNLOUCCMNR-UHFFFAOYSA-N 2-bromo-5-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(S)=CC=C1Br RTXOJNLOUCCMNR-UHFFFAOYSA-N 0.000 description 1
QXWSVWMXWGIWPA-UHFFFAOYSA-N 3-chloro-1,2-dimethylpiperidine Chemical compound CC1C(Cl)CCCN1C QXWSVWMXWGIWPA-UHFFFAOYSA-N 0.000 description 1
UGXACBBAXFABGT-UHFFFAOYSA-N 3-chloro-n,n,2-trimethylpropan-1-amine Chemical compound ClCC(C)CN(C)C UGXACBBAXFABGT-UHFFFAOYSA-N 0.000 description 1
PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 1
LRHTXGQFKONCQG-UHFFFAOYSA-N 5-methoxy-2-thiophen-2-ylsulfanylbenzoic acid Chemical compound S1C(=CC=C1)SC=1C(C(=O)O)=CC(=CC1)OC LRHTXGQFKONCQG-UHFFFAOYSA-N 0.000 description 1
QTQRKOHOJJRZSA-UHFFFAOYSA-N 9aH-thieno[2,3-b]thiochromene Chemical compound S1C=CC=2C1SC1=C(C=2)C=CC=C1 QTQRKOHOJJRZSA-UHFFFAOYSA-N 0.000 description 1
XQOOVCPMIBPUMQ-UHFFFAOYSA-N 9aH-thieno[2,3-b]thiochromene 1-oxide Chemical compound C1=CC=C2SC3S(=O)C=CC3=CC2=C1 XQOOVCPMIBPUMQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229910000881 Cu alloy Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ODCOYFWSWFGGQH-UHFFFAOYSA-N S1C(=CC=C1)SC=1C(C(=O)O)=CC(=CC=1)SC Chemical compound S1C(=CC=C1)SC=1C(C(=O)O)=CC(=CC=1)SC ODCOYFWSWFGGQH-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
OWXLRKWPEIAGAT-UHFFFAOYSA-N [Mg].[Cu] Chemical compound [Mg].[Cu] OWXLRKWPEIAGAT-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002032 methanolic fraction Substances 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002734 organomagnesium group Chemical group 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006798 ring closing metathesis reaction Methods 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
238000005245 sintering Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000008096 xylene Substances 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
- 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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH489061A 1961-04-26 1961-04-26 Verfahren zur Herstellung von neuen heterocyclischen Verbindungen CH405354A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH489061A CH405354A (de)	1961-04-26	1961-04-26	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
GB14952/62A GB1012313A (en)	1961-04-26	1962-04-17	Improvements in or relating to thieno-benzothiapyran derivatives
DK187062AA DK103516C (da)	1961-04-26	1962-04-25	Fremgangsmåde til fremstilling af thieno-[2,3-b][1]-benzothiopyranderivater eller deres salte.
AT342362A AT240359B (de)	1961-04-26	1962-04-26	Verfahren zur Herstellung von neuen Thieno-benzothiopyran-Derivaten und ihrer Säureadditionssalze
FR904796A FR1947M (fr)	1961-04-26	1962-07-23	Médicament a base de dérivé de thiéno-benzothiopyranne.
FR904797A FR1948M (fr)	1961-04-26	1962-07-23	Médicament contenant un dérivé de thiéno-benzothiopyranne.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH489061A CH405354A (de)	1961-04-26	1961-04-26	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH405354A true CH405354A (de)	1966-01-15

Family

ID=4284314

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH489061A CH405354A (de)	1961-04-26	1961-04-26	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen

Country Status (4)

Country	Link
AT (1)	AT240359B (fr)
CH (1)	CH405354A (fr)
FR (1)	FR1947M (fr)
GB (1)	GB1012313A (fr)

1961
- 1961-04-26 CH CH489061A patent/CH405354A/de unknown
1962
- 1962-04-17 GB GB14952/62A patent/GB1012313A/en not_active Expired
- 1962-04-26 AT AT342362A patent/AT240359B/de active
- 1962-07-23 FR FR904796A patent/FR1947M/fr not_active Expired

Also Published As

Publication number	Publication date
AT240359B (de)	1965-05-25
GB1012313A (en)	1965-12-08
FR1947M (fr)	1963-07-29

Publication	Publication Date	Title
DE2111071A1 (de)	1971-09-23	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
NO122614B (fr)	1971-07-19
DE1445845A1 (de)	1969-02-06	Neue Benzomorphane und Verfahren zu ihrer Herstellung
DE1695961A1 (de)	1971-05-19	Neue Azepin-indole und Verfahren zu deren Herstellung
DE1695929C3 (de)	1978-08-31	1 ^-Dihydro-1 -hydroxy^-imino^-amino-6-methylpyrimidine sowie ein Verfahren zu deren Herstellung
AT200578B (de)	1958-11-10	Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen
DE2414093A1 (de)	1974-10-17	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE1065422B (de)	1959-09-17	Verfahren zur Herstellung von Lysergsäure deren N-Derivaten und Estern
CH405354A (de)	1966-01-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
DE3026602C2 (fr)	1990-05-03
US3055888A (en)	1962-09-25	2-alkylmercapto-9-[2'-(n-alkylpiperidyl-2" and pyrrolidyl-2")-ethylidene-1']-thiaxanthenes
CH625789A5 (fr)	1981-10-15
DE1090667B (de)	1960-10-13	Verfahren zur Herstellung von basischen Phenthiazinderivaten
DE60000560T2 (de)	2003-06-05	Verfahren zur Herstellung einer sehr sauberen Phenotiazin Verbindung
CH416624A (de)	1966-07-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT328445B (de)	1976-03-25	Verfahren zur herstellung neuer 4- (1-alkyl-4-piperidyliden) -4h-benzo (4,5) cyclohepta (1,2-b)thiophen-10 (9h) -on verbindungen und ihrer saureadditionssalze
DE2618721C2 (de)	1986-06-05	Benzo(b)-bicyclo[3,3,1]nonene, Verfahren zu deren Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten
DE1795758A1 (de)	1974-10-10	Verfahren zur herstellung von 5hydroxy-5-phenyl-2,3-dihydro-5h-imidazo eckige klammer auf 2,1-a eckige klammer zu isoindolen
AT228217B (de)	1963-07-10	Verfahren zur Herstellung von neuen Homothioxanthen-Derivaten
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
CH433386A (de)	1967-04-15	Verfahren zur Herstellung von neuen heterocyclischen Verbindungen
AT244327B (de)	1965-12-27	Verfahren zur Herstellung von Diphenylalkylaminen und ihren physiologisch verträglichen Salzen
AT230388B (de)	1963-12-10	Verfahren zur Herstellung von neuen 4-Aza-thioxanthen-Derivaten
DE3529159A1 (de)	1986-02-27	Neues verfahren zur herstellung eines aminolactons
DE1470215A1 (de)	1969-05-08	Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung