CH533639A - Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate - Google Patents

Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate

Info

Publication number: CH533639A
Authority: CH; Switzerland
Prior art keywords: cyclohepta; benzo; piperidylidene; formula; methyl
Prior art date: 1970-03-11

Application number

CH359870A

Other languages

German (de)

English (en)

Inventor

Bourquin Jean-Pierre

Schwarb Gustav

Waldvogel Erwin

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.)

1970-03-11

Filing date

1970-03-11

Publication date

1973-02-15

1970-03-11 Application filed by Sandoz Ag filed Critical Sandoz Ag

1970-03-11 Priority to CH359870A priority Critical patent/CH533639A/de

1970-03-11 Priority to CH1088072A priority patent/CH533126A/de

1970-07-31 Priority to CH1159370A priority patent/CH531000A/de

1971-03-03 Priority to US120738A priority patent/US3682930A/en

1971-03-04 Priority to RO66144A priority patent/RO61929A2/fr

1971-03-05 Priority to SU1816330A priority patent/SU422158A3/ru

1971-03-05 Priority to SU1628614A priority patent/SU512711A3/ru

1971-03-08 Priority to FR7107901A priority patent/FR2085695B1/fr

1971-03-09 Priority to ES389044A priority patent/ES389044A1/es

1971-03-09 Priority to YU58671A priority patent/YU35019B/xx

1971-03-09 Priority to IL36370A priority patent/IL36370A/xx

1971-03-09 Priority to OA54190A priority patent/OA03692A/fr

1971-03-09 Priority to DE2111071A priority patent/DE2111071C3/de

1971-03-09 Priority to CS171771A priority patent/CS185562B2/cs

1971-03-09 Priority to BE764019A priority patent/BE764019A/fr

1971-03-09 Priority to HUSA002175 priority patent/HU162868B/hu

1971-03-09 Priority to LU62757D priority patent/LU62757A1/xx

1971-03-09 Priority to FI68371A priority patent/FI52980C/fi

1971-03-09 Priority to PL14675171A priority patent/PL84083B1/pl

1971-03-10 Priority to AT206471A priority patent/AT319238B/de

1971-03-10 Priority to BG017004A priority patent/BG22398A3/xx

1971-03-10 Priority to AT00470/73A priority patent/AT319935B/de

1971-03-10 Priority to CA107,340A priority patent/CA960673A/en

1971-03-10 Priority to SE03074/71A priority patent/SE368954B/xx

1971-03-10 Priority to NL7103174.A priority patent/NL167431C/xx

1971-03-10 Priority to DD16465971A priority patent/DD100000A5/xx

1971-03-10 Priority to JP46013021A priority patent/JPS5217030B1/ja

1971-03-10 Priority to IE29971A priority patent/IE34997B1/xx

1971-03-10 Priority to DK111471A priority patent/DK134404B/da

1971-03-10 Priority to NO90171A priority patent/NO133838C/no

1971-03-11 Priority to ZA711587A priority patent/ZA711587B/xx

1971-04-19 Priority to GB2882373A priority patent/GB1355539A/en

1971-04-19 Priority to GB2348271*A priority patent/GB1355537A/en

1971-06-04 Priority to GB1894073A priority patent/GB1355538A/en

1971-08-27 Priority to NLAANVRAGE7111808,A priority patent/NL171449C/xx

1971-08-30 Priority to BE771964A priority patent/BE771964A/fr

1971-08-31 Priority to CA121,762A priority patent/CA947767A/en

1971-09-02 Priority to AT766471A priority patent/AT321905B/de

1971-09-02 Priority to LU63829D priority patent/LU63829A1/xx

1971-09-03 Priority to OA54351A priority patent/OA03786A/fr

1971-09-03 Priority to FR7131866A priority patent/FR2107917B1/fr

1971-09-03 Priority to SE7111154A priority patent/SE378820B/xx

1971-09-06 Priority to DE19712144490 priority patent/DE2144490A1/de

1971-09-07 Priority to US00178449A priority patent/US3770728A/en

1971-09-21 Priority to GB4392471A priority patent/GB1360219A/en

1972-08-07 Priority to US00278244A priority patent/US3749786A/en

1972-08-08 Priority to US00278738A priority patent/US3853915A/en

1972-09-22 Priority to CA152,330A priority patent/CA966839A/en

1973-02-15 Publication of CH533639A publication Critical patent/CH533639A/de

1973-06-30 Priority to ES416480A priority patent/ES416480A1/es

1974-07-15 Priority to IE149474A priority patent/IE34998B1/xx

1978-03-24 Priority to YU69978A priority patent/YU35254B/xx

1978-09-15 Priority to IT7827770A priority patent/IT7827770A0/it

1983-12-30 Priority to MY8300201A priority patent/MY8300201A/xx

Links

150000008617 benzocycloheptathiophenes Chemical class 0.000 title abstract 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
-1 1-methyl-4-piperidylidene Chemical group 0.000 claims description 69
239000000203 mixture Substances 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 14
125000005605 benzo group Chemical group 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
NFHHBIGYIAIGFH-UHFFFAOYSA-N 2h-cyclohepta[b]thiophene Chemical class C1=CC=CC2=CCSC2=C1 NFHHBIGYIAIGFH-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
BQYAIXRTUQAHCK-UHFFFAOYSA-N 2h-benzo[1,2]cyclohepta[3,6-b]thiophene Chemical class C1=C2C=CC=CC2=CC2=CCSC2=C1 BQYAIXRTUQAHCK-UHFFFAOYSA-N 0.000 claims description 4
JSPBTTYBJKPESQ-UHFFFAOYSA-N 7-chloro-10-(1-methylpiperidin-4-ylidene)-5h-benzo[1,2]cyclohepta[2,4-b]thiophen-4-one Chemical compound C1CN(C)CCC1=C1C2=CC=C(Cl)C=C2CC(=O)C2=C1C=CS2 JSPBTTYBJKPESQ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
150000003577 thiophenes Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 abstract 1
230000002152 alkylating effect Effects 0.000 abstract 1
230000001387 anti-histamine Effects 0.000 abstract 1
229940125715 antihistaminic agent Drugs 0.000 abstract 1
239000000739 antihistaminic agent Substances 0.000 abstract 1
239000003420 antiserotonin agent Substances 0.000 abstract 1
125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 abstract 1
239000000812 cholinergic antagonist Substances 0.000 abstract 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical group C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 132
239000002585 base Substances 0.000 description 97
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
239000000243 solution Substances 0.000 description 51
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
229910052938 sodium sulfate Inorganic materials 0.000 description 31
235000011152 sodium sulphate Nutrition 0.000 description 31
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
238000001704 evaporation Methods 0.000 description 30
230000008020 evaporation Effects 0.000 description 30
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000155 melt Substances 0.000 description 26
238000004452 microanalysis Methods 0.000 description 25
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 21
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
239000013078 crystal Substances 0.000 description 16
239000012458 free base Substances 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
238000001816 cooling Methods 0.000 description 13
238000000354 decomposition reaction Methods 0.000 description 13
239000000284 extract Substances 0.000 description 13
238000002329 infrared spectrum Methods 0.000 description 12
239000012452 mother liquor Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
239000002026 chloroform extract Substances 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
235000011087 fumaric acid Nutrition 0.000 description 9
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000001530 fumaric acid Substances 0.000 description 8
239000011777 magnesium Substances 0.000 description 8
229910052749 magnesium Inorganic materials 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000001035 drying Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
229930192474 thiophene Natural products 0.000 description 7
239000012074 organic phase Substances 0.000 description 6
239000003960 organic solvent 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
238000009835 boiling Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
231100000820 toxicity test Toxicity 0.000 description 5
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
FMLHOINVMYQJPG-UHFFFAOYSA-N 4,5-dibromo-4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound BrC1C(Br)C2=CC=CC=C2C(=O)C2=C1SC=C2 FMLHOINVMYQJPG-UHFFFAOYSA-N 0.000 description 4
238000003747 Grignard reaction Methods 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
NVFSDBKZIASMHM-UHFFFAOYSA-N 2-(1-propan-2-ylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-9-one Chemical compound C(C)(C)N1CCC(CC1)=C1C2=C(C(CC=3SC=CC31)=O)C=CC=C2 NVFSDBKZIASMHM-UHFFFAOYSA-N 0.000 description 3
MMTTWQAQUZDXSB-UHFFFAOYSA-N 2H-cyclohepta[b]thiophen-4-ol Chemical compound S1C=2C(=CC1)C(=CC=CC2)O MMTTWQAQUZDXSB-UHFFFAOYSA-N 0.000 description 3
JAGBUENUSNSSFW-UHFFFAOYSA-N 4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=C1SC=C2 JAGBUENUSNSSFW-UHFFFAOYSA-N 0.000 description 3
NLXKRMCEIJKKJI-UHFFFAOYSA-N 7-methoxy-10-(1-methylpiperidin-4-ylidene)-5h-benzo[1,2]cyclohepta[2,4-b]thiophen-4-one Chemical compound C=1C(OC)=CC=C2C=1CC(=O)C=1SC=CC=1C2=C1CCN(C)CC1 NLXKRMCEIJKKJI-UHFFFAOYSA-N 0.000 description 3
QBGZNZROAMEYIE-UHFFFAOYSA-N 8,9-dibromo-13-chloro-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,11,13-pentaen-2-one Chemical compound ClC=1C=CC2=C(C(C3=C(SC=C3)C(C2Br)Br)=O)C1 QBGZNZROAMEYIE-UHFFFAOYSA-N 0.000 description 3
CRMYGYDSPBLQGV-UHFFFAOYSA-N 8-bromo-10-(1-methylpiperidin-4-ylidene)-5h-benzo[3,4]cyclohepta[1,3-b]thiophen-4-one Chemical compound C1CN(C)CCC1=C1C2=CC(Br)=CC=C2CC(=O)C2=C1C=CS2 CRMYGYDSPBLQGV-UHFFFAOYSA-N 0.000 description 3
OYGMIRYICCMQKU-UHFFFAOYSA-N 8-chloro-10-(1-methylpiperidin-4-ylidene)-5h-benzo[3,4]cyclohepta[1,3-b]thiophen-4-one Chemical compound C1CN(C)CCC1=C1C2=CC(Cl)=CC=C2CC(=O)C2=C1C=CS2 OYGMIRYICCMQKU-UHFFFAOYSA-N 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
241000700198 Cavia Species 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
230000001558 histaminolytic effect Effects 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
HIZVLPRLSUXECX-UHFFFAOYSA-N 12-methoxy-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,11,13-pentaen-2-one Chemical compound COC1=CC2=C(C(C3=C(SC=C3)CC2)=O)C=C1 HIZVLPRLSUXECX-UHFFFAOYSA-N 0.000 description 2
FBSDIGIDGOKTKI-UHFFFAOYSA-N 2-(1-butylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one Chemical compound C(CCC)N1CCC(CC1)=C1C2=C(CC(C=3SC=CC31)=O)C=CC=C2 FBSDIGIDGOKTKI-UHFFFAOYSA-N 0.000 description 2
ODFQXGXGVGIWAB-UHFFFAOYSA-N 2-(1-butylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-9-one Chemical compound C(CCC)N1CCC(CC1)=C1C2=C(C(CC=3SC=CC31)=O)C=CC=C2 ODFQXGXGVGIWAB-UHFFFAOYSA-N 0.000 description 2
FZWLJBMVENZFFJ-UHFFFAOYSA-N 4-(13-chloro-8-piperidin-1-yl-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,8,11,13-hexaen-2-ylidene)-1-methylpiperidine Chemical compound ClC=1C=CC2=C(C(C3=C(SC=C3)C(=C2)N2CCCCC2)=C2CCN(CC2)C)C=1 FZWLJBMVENZFFJ-UHFFFAOYSA-N 0.000 description 2
DTDXVJLMRMXSPU-UHFFFAOYSA-N 4-chloro-1-ethylpiperidine Chemical compound CCN1CCC(Cl)CC1 DTDXVJLMRMXSPU-UHFFFAOYSA-N 0.000 description 2
BEOQQIHTRMWVOG-UHFFFAOYSA-N 4-methoxy-2-(2-thiophen-2-ylethenyl)benzoic acid Chemical compound COC1=CC(=C(C(=O)O)C=C1)C=CC=1SC=CC1 BEOQQIHTRMWVOG-UHFFFAOYSA-N 0.000 description 2
WGEWUSWVZVXBSF-UHFFFAOYSA-N 4-methoxy-2-(2-thiophen-2-ylethyl)benzoic acid Chemical compound COC1=CC(=C(C(=O)O)C=C1)CCC=1SC=CC1 WGEWUSWVZVXBSF-UHFFFAOYSA-N 0.000 description 2
WPNRDWPYKQWTLC-UHFFFAOYSA-N 7-chloro-10-(1-methylpiperidin-4-ylidene)-4h-benzo[1,2]cyclohepta[2,4-b]thiophen-5-one Chemical compound C1CN(C)CCC1=C1C2=CC=C(Cl)C=C2C(=O)CC2=C1C=CS2 WPNRDWPYKQWTLC-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
JPDLPUXSEBEPQJ-UHFFFAOYSA-N 8,9-dibromo-12-methoxy-6-thiatricyclo[8.4.0.03,7]tetradeca-1(10),3(7),4,11,13-pentaen-2-one Chemical compound BrC1C2=C(C(C3=C(SC=C3)C1Br)=O)C=CC(=C2)OC JPDLPUXSEBEPQJ-UHFFFAOYSA-N 0.000 description 2
SABRAZLAGGKSND-UHFFFAOYSA-N 8-bromo-2-(1-methylpiperidin-4-yl)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ol Chemical compound CN1CCC(CC1)C1(O)c2ccsc2C(Br)=Cc2ccccc12 SABRAZLAGGKSND-UHFFFAOYSA-N 0.000 description 2
KKOGZTXMIINMHV-UHFFFAOYSA-N C(C)(C)N1CCC(CC1)=C1C2=C(C=C(C=3SC=CC31)N3CCCCC3)C=CC=C2 Chemical compound C(C)(C)N1CCC(CC1)=C1C2=C(C=C(C=3SC=CC31)N3CCCCC3)C=CC=C2 KKOGZTXMIINMHV-UHFFFAOYSA-N 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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MCTGFYNNAQRJQD-UHFFFAOYSA-N 1-butyl-4-chloropiperidine Chemical compound CCCCN1CCC(Cl)CC1 MCTGFYNNAQRJQD-UHFFFAOYSA-N 0.000 description 1
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OGXRKFXTEBOAFT-UHFFFAOYSA-N 2-(1-ethylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one Chemical compound C(C)N1CCC(CC1)=C1C2=C(CC(C=3SC=CC31)=O)C=CC=C2 OGXRKFXTEBOAFT-UHFFFAOYSA-N 0.000 description 1
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GYOWBWUJHOPQBZ-UHFFFAOYSA-N 4-(9-piperidin-1-yl-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ylidene)-1-propan-2-ylpiperidine Chemical compound C(C)(C)N1CCC(CC1)=C1C2=C(C(=CC=3SC=CC31)N3CCCCC3)C=CC=C2 GYOWBWUJHOPQBZ-UHFFFAOYSA-N 0.000 description 1
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PAACGLGXFICDPG-UHFFFAOYSA-N 4-chloro-1-propan-2-ylpiperidine Chemical compound CC(C)N1CCC(Cl)CC1 PAACGLGXFICDPG-UHFFFAOYSA-N 0.000 description 1
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CRKMOHRPUZPMBZ-UHFFFAOYSA-N 8-chloro-10-(1-methylpiperidin-4-ylidene)-4h-benzo[3,4]cyclohepta[1,3-b]thiophen-5-one Chemical compound C1CN(C)CCC1=C1C2=CC(Cl)=CC=C2C(=O)CC2=C1C=CS2 CRKMOHRPUZPMBZ-UHFFFAOYSA-N 0.000 description 1
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BOCWWEKHCDJGGO-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.CN1CCC(CC1)=C1C2=C(C(CC=3SC=CC31)=O)C=CC=C2 Chemical compound C(C=CC(=O)O)(=O)O.CN1CCC(CC1)=C1C2=C(C(CC=3SC=CC31)=O)C=CC=C2 BOCWWEKHCDJGGO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
239000004133 Sodium thiosulphate Substances 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
230000003113 alkalizing effect Effects 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
AKYJPOPHGMQXHH-UHFFFAOYSA-N benzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=C1SC=C2 AKYJPOPHGMQXHH-UHFFFAOYSA-N 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
MWWHYPORGYMFIP-UHFFFAOYSA-N cyclohepta[b]thiophen-4-one Chemical compound O=C1C=CC=CC2=C1C=CS2 MWWHYPORGYMFIP-UHFFFAOYSA-N 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
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001640 fractional crystallisation Methods 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
239000012362 glacial acetic acid Substances 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229940049920 malate Drugs 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
150000007524 organic acids Chemical class 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH359870A 1970-03-11 1970-03-11 Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate CH533639A (de)

Priority Applications (53)

Application Number	Priority Date	Filing Date	Title
CH359870A CH533639A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate
CH1088072A CH533126A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH1159370A CH531000A (de)	1970-03-11	1970-07-31	Verfahren zur Herstellung neuer Benzocycloheptathiophene
US120738A US3682930A (en)	1970-03-11	1971-03-03	4(1-alkyl-4-piperidylidine)-4h-benzo {84,5{9 {0 cyclohepta {8 1,2{14 6{9
RO66144A RO61929A2 (fr)	1970-03-11	1971-03-04	Procede pour la preparation des composes de 4h-benzo-(4,5)-cyclohepta-(1,2-b)-thiphene
SU1816330A SU422158A3 (ru)	1970-03-11	1971-03-05	Способ получения производных 4н-бензо [4,5] циклогепта [1,2-6] тиофена
SU1628614A SU512711A3 (ru)	1970-03-11	1971-03-05	Способ получени производных бензо-(4,5)-циклогепта (1,2-в) -тиофена
FR7107901A FR2085695B1 (fr)	1970-03-11	1971-03-08
ES389044A ES389044A1 (es)	1970-03-11	1971-03-09	Procedimiento para la obtencion de derivados del benzoci- cloheptatiofeno.
YU58671A YU35019B (en)	1970-03-11	1971-03-09	Process for preparing novel 4-(1-alkyl-4-piperidylidene)-4h-benzo(4,5)cyclohepta(1,2-)tiophene-10(9h)-ones or-9(10h)-ones
IL36370A IL36370A (en)	1970-03-11	1971-03-09	4-piperidylidene-benzocyclohepta-thiophene derivatives,their preparation and pharmaceutical compositions containing them
OA54190A OA03692A (fr)	1970-03-11	1971-03-09	Nouveaux dérivés du benzo-cyclohepta-thiopène et leur préparation.
DE2111071A DE2111071C3 (de)	1970-03-11	1971-03-09	4-(l-Alkyl-4-piperidyuden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10 (9H)-one bzw. -9 (10H)-one, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
CS171771A CS185562B2 (en)	1970-03-11	1971-03-09	Method of producing new 4-/1-alkyl-4-piperidyliden/-4h-benzo/4,5/cyclohepta/1,2-b/thiophen-9/10h/-ones or 10/9h/-ones
BE764019A BE764019A (fr)	1970-03-11	1971-03-09	Nouveaux derives du benzo-cyclohepta-thiophene et leur preparation
HUSA002175 HU162868B (fr)	1970-03-11	1971-03-09
LU62757D LU62757A1 (fr)	1970-03-11	1971-03-09
FI68371A FI52980C (fr)	1970-03-11	1971-03-09
PL14675171A PL84083B1 (fr)	1970-03-11	1971-03-09
AT206471A AT319238B (de)	1970-03-11	1971-03-10	Verfahren zur Herstellung neuer 4-(1-Alkyl-4-piperidyliden)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-9(10H)- bzw. 10(9H)-on-Verbindungen und ihrer Säureadditionssalze
BG017004A BG22398A3 (bg)	1970-03-11	1971-03-10	Метод за получаване на хетероциклени съединения
AT00470/73A AT319935B (de)	1970-03-11	1971-03-10	Vzh neuer 9(10)-brom bzw.chlor-4h-benzo(4,5)-cyclohepta(1,2-b)thiophen-4-on-verbindungen und ihrer saeureadditionssalze
CA107,340A CA960673A (en)	1970-03-11	1971-03-10	Piperidylidene benzocycloheptathiophenes
SE03074/71A SE368954B (fr)	1970-03-11	1971-03-10
NL7103174.A NL167431C (nl)	1970-03-11	1971-03-10	Werkwijze voor de bereiding van een histaminolytisch werkend preparaat en werkwijze voor de bereiding van een histaminolytisch werkend 4-(1-alkyl-4-piperidyli- deen)benzo4,5cyclohepta1,2-bthiofeen
DD16465971A DD100000A5 (fr)	1970-03-11	1971-03-10
JP46013021A JPS5217030B1 (fr)	1970-03-11	1971-03-10
IE29971A IE34997B1 (en)	1970-03-11	1971-03-10	4-piperidylidene-benzocycloheptathiopenes
DK111471A DK134404B (da)	1970-03-11	1971-03-10	Analogifremgangsmåde til fremstilling af benzocycloheptathiophenderivater eller syreadditionssalte deraf.
NO90171A NO133838C (fr)	1970-03-11	1971-03-10
ZA711587A ZA711587B (en)	1970-03-11	1971-03-11	Improvements in or relating to organic compounds
GB2882373A GB1355539A (en)	1970-03-11	1971-04-19	Benzocycloheptathiophene derivative
GB2348271*A GB1355537A (en)	1970-03-11	1971-04-19	4-piperidylidene-benzocycloheptathiophenes
GB1894073A GB1355538A (en)	1970-03-11	1971-06-04	Benzocycloheptathiophene derivatives
NLAANVRAGE7111808,A NL171449C (nl)	1970-03-11	1971-08-27	Werkwijze ter bereiding van een met een aminoalkylideengroep gesubstitueerd tricyclisch keton.
BE771964A BE771964A (fr)	1970-03-11	1971-08-30	Procede pour la preparation de derives du benzo-cyclohepta-thiophene
CA121,762A CA947767A (en)	1970-03-11	1971-08-31	Process for the production of benzocyclohep thathiophenones
AT766471A AT321905B (de)	1970-03-11	1971-09-02	Verfahren zur herstellung neuer thiophenderivate und ihrer salze
LU63829D LU63829A1 (fr)	1970-03-11	1971-09-02
OA54351A OA03786A (fr)	1970-03-11	1971-09-03	Procédé pour la préparation de dérivés du benzo-cyclohepta-thiophène.
FR7131866A FR2107917B1 (fr)	1970-03-11	1971-09-03
SE7111154A SE378820B (fr)	1970-03-11	1971-09-03
DE19712144490 DE2144490A1 (de)	1970-03-11	1971-09-06	Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung
US00178449A US3770728A (en)	1970-03-11	1971-09-07	Substituted 4h-benzo(4,5)cyclohepta(1,2-b)thiophen-10(9h)-ones
GB4392471A GB1360219A (en)	1970-03-11	1971-09-21	4h-benzo-4,5 - cyclohepta-1,2 - b-thiophen-9-ones and process for their manufacture
US00278244A US3749786A (en)	1970-03-11	1972-08-07	Organic compounds in treating allergic conditions
US00278738A US3853915A (en)	1970-03-11	1972-08-08	9-or 10-halo-4h-benzo{8 4,5{9 cyclo-hepta{8 1,2-b{9 thiophen-4-ones
CA152,330A CA966839A (en)	1970-03-11	1972-09-22	Piperidylidene banzocycloheptathiophanes
ES416480A ES416480A1 (es)	1970-03-11	1973-06-30	Procedimiento para la obtencion de derivados del benzocic- loheptatiofeno.
IE149474A IE34998B1 (en)	1970-03-11	1974-07-15	A benzocycloheptathiophene derivative
YU69978A YU35254B (en)	1970-03-11	1978-03-24	Process for preparing novel 4-(-alkyl-4-piperidylidene)-4h-benzol(4,5)cyclohepta(1,2,-b)thiophene-10(9h)-ones
IT7827770A IT7827770A0 (it)	1970-03-11	1978-09-15	Che contengono questi derivati. derivati delbenzo-cicloepta-tiofene, loro preparazione e prodotti medicinali
MY8300201A MY8300201A (en)	1970-03-11	1983-12-30	A benzocycloheptathiophene derivative

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH359870A CH533639A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate

Publications (1)

Publication Number	Publication Date
CH533639A true CH533639A (de)	1973-02-15

Family

ID=4259436

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH359870A CH533639A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate
CH1088072A CH533126A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer heterocyclischer Verbindungen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1088072A CH533126A (de)	1970-03-11	1970-03-11	Verfahren zur Herstellung neuer heterocyclischer Verbindungen

Country Status (5)

Country	Link
AT (1)	AT319935B (fr)
CH (2)	CH533639A (fr)
RO (1)	RO61929A2 (fr)
SU (1)	SU422158A3 (fr)
ZA (1)	ZA711587B (fr)

1970
- 1970-03-11 CH CH359870A patent/CH533639A/de not_active IP Right Cessation
- 1970-03-11 CH CH1088072A patent/CH533126A/de not_active IP Right Cessation
1971
- 1971-03-04 RO RO66144A patent/RO61929A2/fr unknown
- 1971-03-05 SU SU1816330A patent/SU422158A3/ru active
- 1971-03-10 AT AT00470/73A patent/AT319935B/de not_active IP Right Cessation
- 1971-03-11 ZA ZA711587A patent/ZA711587B/xx unknown

Also Published As

Publication number	Publication date
AT319935B (de)	1975-01-10
CH533126A (de)	1973-01-31
ZA711587B (en)	1972-10-25
SU422158A3 (ru)	1974-03-30
RO61929A2 (fr)	1977-05-20

Legal Events

Date	Code	Title	Description
1990-05-31	PL	Patent ceased

Publication	Publication Date	Title
DE2111071C3 (de)	1979-07-12	4-(l-Alkyl-4-piperidyuden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10 (9H)-one bzw. -9 (10H)-one, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
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
DE2414093A1 (de)	1974-10-17	Verfahren zur herstellung neuer heterocyclischer verbindungen
CH630904A5 (en)	1982-07-15	Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline.
DE2745742A1 (de)	1978-04-13	Piperidylidenderivate von benzoxanthenen, -thioxanthenen und -dibenzoxepinen, verfahren zu deren herstellung und deren verwendung als psychopharmaca
CH533639A (de)	1973-02-15	Verfahren zur Herstellung neuer Benzo(4,5)cyclohepta(1,2-b)-thiophen-Derivate
DE1470314C3 (fr)	1975-02-20
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
CH537404A (de)	1973-05-31	Verfahren zur Herstellung neuer Thiophenderivate
AT367404B (de)	1982-07-12	Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen
CH496714A (de)	1970-09-30	Verfahren zur Herstellung von Derivaten des 1,3,4,5-Tetrahydrobenzodiazepins
AT249665B (de)	1966-10-25	Verfahren zur Herstellung von neuen 4H-Benzo[4,5]cyclohepta[1,2-b]thiophen-Derivaten
AT251572B (de)	1967-01-10	Verfahren zur Herstellung von neuen Thieno-benzothiazin-Derivaten
AT337182B (de)	1977-06-10	Verfahren zur herstellung neuer 4-(4-piperidyliden)-4h-benzo(4,5)cyclohepta (1,2-b) thiophen-derivate und ihrer saureadditionssalze
AT337181B (de)	1977-06-10	Verfahren zur herstellung neuer 4-(4-piperidyliden)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-derivate und ihrer saureadditionssalze
AT367406B (de)	1982-07-12	Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen
DE1228272B (de)	1966-11-10	Verfahren zur Herstellung von 11-Aminoalkyldibenzo[b, f]thiepinen
AT269128B (de)	1969-03-10	Verfahren zur Herstellung des neuen 4-(3-Methylaminopropyliden)-9,10-dihydro-4H-benzo[4,5]cyclohepta[2,1-b]thiophens und seiner Salze
CH563388A5 (en)	1975-06-30	Substd benzo-cycloheptathiophene prepn - used as an anti- histaminic
AT211001B (de)	1960-09-10	Verfahren zur Herstellung von neuen Scopin-äthern
AT243258B (de)	1965-11-10	Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo[4,5]-cyclohepta[1,2-b]thiophen-Derivaten
AT256107B (de)	1967-08-10	Verfahren zur Herstellung von neuen Aza-dibenzo-cycloheptenderivaten
DE1238040B (de)	1967-04-06	Verfahren zur Herstellung von 4H-Benzo [4, 5]-cyclohepta [1, 2-b] thiophenen
CH587845A5 (en)	1977-05-13	New piperidylidene-benzo-cyclohepta-thiophenes prodn. - by dehydrating corresp. alcohols, useful e.g. as neuroleptics and analgesics