CH626360A5 - - Google Patents

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Publication number: CH626360A5
Authority: CH; Switzerland
Prior art keywords: phenyl; methoxybenzothiophene; preparation; reacted; hydrogen
Prior art date: 1975-10-28

Application number

CH1355376A

Other languages

German (de)

English (en)

Inventor

Charles David Jones

Tulio Suarez

Original Assignee

Lilly Co Eli

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.)

1975-10-28

Filing date

1976-10-27

Publication date

1981-11-13

1976-10-27 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-11-13 Publication of CH626360A5 publication Critical patent/CH626360A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 79
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 64
238000002360 preparation method Methods 0.000 claims description 54
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 38
-1 pyrrolidino - Chemical class 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
238000000034 method Methods 0.000 claims description 30
ABRMTASSNGLERB-UHFFFAOYSA-N 6-methoxy-3-phenyl-1-benzothiophene Chemical compound C=1SC2=CC(OC)=CC=C2C=1C1=CC=CC=C1 ABRMTASSNGLERB-UHFFFAOYSA-N 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 12
239000000460 chlorine Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
231100000252 nontoxic Toxicity 0.000 claims description 9
230000003000 nontoxic effect Effects 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
HZYRPUKLUAUOMF-UHFFFAOYSA-N 3-phenyl-1-benzothiophene Chemical compound C=1SC2=CC=CC=C2C=1C1=CC=CC=C1 HZYRPUKLUAUOMF-UHFFFAOYSA-N 0.000 claims description 5
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
JXVSFTDLCRWQDQ-UHFFFAOYSA-N (4-hydroxyphenyl)-(5-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC(O)=CC=C2S1 JXVSFTDLCRWQDQ-UHFFFAOYSA-N 0.000 claims description 4
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 4
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 claims description 4
LXFAAQZFIXJKML-UHFFFAOYSA-N (4-methoxyphenyl)-(6-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=C(OC)C=C2S1 LXFAAQZFIXJKML-UHFFFAOYSA-N 0.000 claims description 3
YSPOSMCGZQNGSH-UHFFFAOYSA-N (6-hydroxy-3-phenyl-1-benzothiophen-2-yl)-phenylmethanone Chemical compound S1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 YSPOSMCGZQNGSH-UHFFFAOYSA-N 0.000 claims description 3
XXNIULFNOSVMMQ-UHFFFAOYSA-N (6-methoxy-3-phenyl-1-benzothiophen-2-yl)-phenylmethanone Chemical compound S1C2=CC(OC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 XXNIULFNOSVMMQ-UHFFFAOYSA-N 0.000 claims description 3
XMAHCTYSHJSSOD-UHFFFAOYSA-N 1-[2-[4-(6-methoxy-1-benzothiophen-3-yl)phenoxy]ethyl]pyrrolidine Chemical compound C=1SC2=CC(OC)=CC=C2C=1C(C=C1)=CC=C1OCCN1CCCC1 XMAHCTYSHJSSOD-UHFFFAOYSA-N 0.000 claims description 3
RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 claims description 3
WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 claims description 3
RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 claims description 3
UNERQANHKKJITO-UHFFFAOYSA-N 4-cyclopentyloxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1CCCC1 UNERQANHKKJITO-UHFFFAOYSA-N 0.000 claims description 3
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 3
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
NSPMWBIYXNBSOE-UHFFFAOYSA-N (2-methoxyphenyl)-(6-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(OC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1OC NSPMWBIYXNBSOE-UHFFFAOYSA-N 0.000 claims description 2
GVPUXRFQCKYOOU-UHFFFAOYSA-N (3-chlorophenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC(Cl)=C1 GVPUXRFQCKYOOU-UHFFFAOYSA-N 0.000 claims description 2
MQCYBMKKZJDJST-UHFFFAOYSA-N (3-chlorophenyl)-(6-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(OC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC(Cl)=C1 MQCYBMKKZJDJST-UHFFFAOYSA-N 0.000 claims description 2
RLJCHVHJOATZPM-UHFFFAOYSA-N (3-methoxyphenyl)-(6-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(C3=CC=C(OC)C=C3S2)C=2C=CC=CC=2)=C1 RLJCHVHJOATZPM-UHFFFAOYSA-N 0.000 claims description 2
PLPZSSCOBLPPHF-UHFFFAOYSA-N (4-chlorophenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=C(Cl)C=C1 PLPZSSCOBLPPHF-UHFFFAOYSA-N 0.000 claims description 2
OLFVKKHOIGCSSW-UHFFFAOYSA-N (4-chlorophenyl)-(6-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(OC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=C(Cl)C=C1 OLFVKKHOIGCSSW-UHFFFAOYSA-N 0.000 claims description 2
BCBVRWIGOFHNKN-UHFFFAOYSA-N (4-hydroxyphenyl)-(3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2S1 BCBVRWIGOFHNKN-UHFFFAOYSA-N 0.000 claims description 2
MUVICMHSNJOTOO-UHFFFAOYSA-N (4-methoxyphenyl)-(3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2S1 MUVICMHSNJOTOO-UHFFFAOYSA-N 0.000 claims description 2
UXMZUDYLHCQQOK-UHFFFAOYSA-N (4-methoxyphenyl)-(5-methoxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC(OC)=CC=C2S1 UXMZUDYLHCQQOK-UHFFFAOYSA-N 0.000 claims description 2
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 2
229960002303 citric acid monohydrate Drugs 0.000 claims description 2
ZMILKKNFIRLYJV-UHFFFAOYSA-N 5-methoxy-3-phenyl-1-benzothiophene-2-carbonyl chloride Chemical compound C12=CC(OC)=CC=C2SC(C(Cl)=O)=C1C1=CC=CC=C1 ZMILKKNFIRLYJV-UHFFFAOYSA-N 0.000 claims 2
NTQBCMFVVGYVRK-UHFFFAOYSA-N (2-hydroxyphenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1O NTQBCMFVVGYVRK-UHFFFAOYSA-N 0.000 claims 1
VYFAMSCKYOCARC-UHFFFAOYSA-N (3-hydroxyphenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound OC1=CC=CC(C(=O)C2=C(C3=CC=C(O)C=C3S2)C=2C=CC=CC=2)=C1 VYFAMSCKYOCARC-UHFFFAOYSA-N 0.000 claims 1
YGYRPLPMKMFKPO-UHFFFAOYSA-N (4-cyclopentyloxyphenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C(C=C1)=CC=C1OC1CCCC1 YGYRPLPMKMFKPO-UHFFFAOYSA-N 0.000 claims 1
HIGSIPXITGMQEO-UHFFFAOYSA-N (4-hydroxyphenyl)-(6-hydroxy-3-phenyl-1-benzothiophen-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=C(O)C=C2S1 HIGSIPXITGMQEO-UHFFFAOYSA-N 0.000 claims 1
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
239000000203 mixture Substances 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
239000000047 product Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
238000004458 analytical method Methods 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000003921 oil Substances 0.000 description 26
235000019198 oils Nutrition 0.000 description 26
239000010410 layer Substances 0.000 description 24
239000013078 crystal Substances 0.000 description 21
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
238000010992 reflux Methods 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
238000001819 mass spectrum Methods 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
238000009835 boiling Methods 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
230000003509 anti-fertility effect Effects 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003433 contraceptive agent Substances 0.000 description 6
230000035935 pregnancy Effects 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
241000271566 Aves Species 0.000 description 5
241000282421 Canidae Species 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000012458 free base Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
238000005187 foaming Methods 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
NFJXXLZCPGFALB-UHFFFAOYSA-N 4-(6-methoxy-1-benzothiophen-3-yl)phenol Chemical compound C=1SC2=CC(OC)=CC=C2C=1C1=CC=C(O)C=C1 NFJXXLZCPGFALB-UHFFFAOYSA-N 0.000 description 3
NSTJDFGPPOXIAT-UHFFFAOYSA-N 4-cyclopentyloxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1CCCC1 NSTJDFGPPOXIAT-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
229930016911 cinnamic acid Natural products 0.000 description 3
235000013985 cinnamic acid Nutrition 0.000 description 3
229960004106 citric acid Drugs 0.000 description 3
239000003480 eluent Substances 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 3
238000006798 ring closing metathesis reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 2
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 2
DQUZFPKUMCZPQD-UHFFFAOYSA-N 1-benzothiophen-6-ol Chemical class OC1=CC=C2C=CSC2=C1 DQUZFPKUMCZPQD-UHFFFAOYSA-N 0.000 description 2
FRIGLBWVTJAEHM-UHFFFAOYSA-N 3,4-diphenyl-1,2-dihydronaphthalene Chemical class C1CC2=CC=CC=C2C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FRIGLBWVTJAEHM-UHFFFAOYSA-N 0.000 description 2
QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 2
XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 2
229940073735 4-hydroxy acetophenone Drugs 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1355376A 1975-10-28 1976-10-27 CH626360A5 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US62600975A	1975-10-28	1975-10-28

Publications (1)

Publication Number	Publication Date
CH626360A5 true CH626360A5 (cs)	1981-11-13

Family

ID=24508577

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1355376A CH626360A5 (cs)	1975-10-28	1976-10-27

Country Status (27)

Country	Link
US (1)	US4075227A (cs)
JP (1)	JPS5253852A (cs)
AR (1)	AR216451A1 (cs)
AT (1)	AT352709B (cs)
AU (1)	AU509682B2 (cs)
BE (1)	BE847718A (cs)
BG (1)	BG27554A3 (cs)
CA (1)	CA1064031A (cs)
CH (1)	CH626360A5 (cs)
CS (1)	CS196328B2 (cs)
DD (1)	DD127463A5 (cs)
DE (1)	DE2647864C2 (cs)
DK (1)	DK484576A (cs)
ES (1)	ES452737A1 (cs)
FR (1)	FR2329270A1 (cs)
GB (1)	GB1572506A (cs)
GR (1)	GR62400B (cs)
IE (1)	IE43970B1 (cs)
IL (1)	IL50413A (cs)
MX (1)	MX3972E (cs)
NL (1)	NL7611972A (cs)
NZ (1)	NZ182428A (cs)
PL (1)	PL109366B1 (cs)
PT (1)	PT65753B (cs)
RO (1)	RO70768A (cs)
SE (1)	SE427035B (cs)
ZA (1)	ZA766442B (cs)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
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JPS5740478A (en) *	1980-08-22	1982-03-06	Ono Pharmaceut Co Ltd	Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative
US4436748A (en) *	1980-10-20	1984-03-13	Hoechst-Roussel Pharmaceuticals Inc.	Benzo[b]thiophenes
US4418068A (en) *	1981-04-03	1983-11-29	Eli Lilly And Company	Antiestrogenic and antiandrugenic benzothiophenes
US4528399A (en) *	1981-04-22	1985-07-09	Hoechst-Roussel Pharmaceuticals Inc.	Benzo[b]thiophenes intermediates
US5354861A (en) *	1992-11-04	1994-10-11	National University Of Singapore	2-(benzyl)-3-arylbenzofurans as antitumour and hypocholesterolemic agents
IL109990A (en) *	1993-06-21	1999-06-20	Lilly Co Eli	Materials and methods for screening anti-osteoporosis agents
US5523416A (en) *	1994-07-22	1996-06-04	Eli Lilly And Company	Process for preparing 3-(4-aminoethoxy-benzoyl) benzo (B)-thiophenes
US5552401A (en) *	1995-02-28	1996-09-03	Eli Lilly And Company	2-benzyl-3-arylbenzothiophenes
ZA9710262B (en) *	1996-11-19	1999-05-13	Lilly Co Eli	Process for the synthesis of benzothiophenes
US6107346A (en) *	1997-08-11	2000-08-22	Eli Lilly And Company	Methods for treating hyperlipidemia
US5908859A (en) *	1997-08-11	1999-06-01	Eli Lilly And Company	Benzothiophenes for inhibiting hyperlipidemia
US7125903B1 (en)	1999-09-14	2006-10-24	Aventis Pharmaceuticals Inc.	Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists
US7091199B1 (en)	1999-09-14	2006-08-15	Aventis Pharmaceuticals Inc.	Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists
US7253165B2 (en) *	1999-09-14	2007-08-07	Aventis Pharmaceuticals Inc.	Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists
CN1193986C (zh) *	1999-10-04	2005-03-23	日本曹达株式会社	苯酚化合物和使用它的记录材料
AU2002230409A1 (en) *	2000-11-27	2002-06-03	Eli Lilly And Company	Process for preparing 3-aryl-benzo(b)thiophenes
AUPR283801A0 (en) *	2001-02-01	2001-03-01	Australian National University, The	Chemical compounds and methods
JP3904517B2 (ja) *	2001-04-04	2007-04-11	日本曹達株式会社	組成物、記録材料及び記録シート
EP1395563B1 (en) *	2001-05-22	2006-03-29	Eli Lilly And Company	2-substituted 1,2,3,4-tetrahydroquinolines and derivatives thereof, compositions and methods
EP1401446B1 (en) *	2001-05-22	2005-02-09	Eli Lilly And Company	Tetrahydroquinolin derivatives for the inhibition of diseases associated with estrogen deprivation or with an aberrant physiological response to endogenous estrogen
DE10309645A1 (de)	2003-03-06	2004-09-16	Basf Ag	Verfahren zur Herstellung von a-(3-Arylthio)-acetophenonen
KR20190117582A (ko)	2017-02-10	2019-10-16	쥐원 쎄라퓨틱스, 인크.	벤조티오펜 에스트로겐 수용체 조정제

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1456323A (en) *	1974-06-06	1976-11-24	Labaz	Benzothiophenes process for preparing them and pharmaceutical compositions containing the same
US3947470A (en) *	1974-06-20	1976-03-30	Smithkline Corporation	Substituted benzofurans and benzothiophenes
US4001426A (en) *	1974-10-17	1977-01-04	Smithkline Corporation	Substituted benzofurans and benzothiophenes
US3983245A (en) *	1975-02-06	1976-09-28	Smithkline Corporation	Certain 4-(3-azacycloalkoxy or azacycloalkylmethoxy)benzoylbenzofurans or benzothiophenes

1976
- 1976-09-02 AU AU17408/76A patent/AU509682B2/en not_active Expired
- 1976-09-05 IL IL50413A patent/IL50413A/xx unknown
- 1976-10-21 MX MX764992U patent/MX3972E/es unknown
- 1976-10-21 CA CA263,897A patent/CA1064031A/en not_active Expired
- 1976-10-22 DE DE2647864A patent/DE2647864C2/de not_active Expired
- 1976-10-25 GR GR52003A patent/GR62400B/el unknown
- 1976-10-25 PT PT65753A patent/PT65753B/pt unknown
- 1976-10-25 GB GB44200/76A patent/GB1572506A/en not_active Expired
- 1976-10-26 RO RO7688226A patent/RO70768A/ro unknown
- 1976-10-26 ES ES452737A patent/ES452737A1/es not_active Expired
- 1976-10-27 SE SE7611954A patent/SE427035B/xx unknown
- 1976-10-27 ZA ZA00766442A patent/ZA766442B/xx unknown
- 1976-10-27 DK DK484576A patent/DK484576A/da not_active Application Discontinuation
- 1976-10-27 NZ NZ182428A patent/NZ182428A/xx unknown
- 1976-10-27 IE IE2370/76A patent/IE43970B1/en unknown
- 1976-10-27 JP JP51129998A patent/JPS5253852A/ja active Granted
- 1976-10-27 CH CH1355376A patent/CH626360A5/de not_active IP Right Cessation
- 1976-10-28 FR FR7632513A patent/FR2329270A1/fr active Granted
- 1976-10-28 BE BE1007724A patent/BE847718A/xx not_active IP Right Cessation
- 1976-10-28 NL NL7611972A patent/NL7611972A/xx not_active Application Discontinuation
- 1976-10-28 AR AR265276A patent/AR216451A1/es active
- 1976-10-28 BG BG034551A patent/BG27554A3/xx unknown
- 1976-10-28 AT AT800776A patent/AT352709B/de not_active IP Right Cessation
- 1976-10-28 DD DD195510A patent/DD127463A5/xx unknown
- 1976-10-28 CS CS766973A patent/CS196328B2/cs unknown
- 1976-10-28 PL PL1976193328A patent/PL109366B1/pl unknown
- 1976-11-22 US US05/743,819 patent/US4075227A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CS196328B2 (en)	1980-03-31
PL109366B1 (en)	1980-05-31
ATA800776A (de)	1979-03-15
BG27554A3 (en)	1979-11-12
AU1740876A (en)	1978-03-09
ES452737A1 (es)	1978-01-01
DD127463A5 (cs)	1977-09-28
AU509682B2 (en)	1980-05-22
CA1064031A (en)	1979-10-09
RO70768A (ro)	1982-10-26
GR62400B (en)	1979-04-10
IE43970L (en)	1977-04-28
SE427035B (sv)	1983-02-28
JPS61344B2 (cs)	1986-01-08
NL7611972A (nl)	1977-05-02
DE2647864A1 (de)	1977-05-12
FR2329270B1 (cs)	1979-07-27
IE43970B1 (en)	1981-07-15
GB1572506A (en)	1980-07-30
DK484576A (da)	1977-04-29
US4075227A (en)	1978-02-21
IL50413A (en)	1980-05-30
PT65753A (en)	1976-11-01
AT352709B (de)	1979-10-10
ZA766442B (en)	1978-06-28
AR216451A1 (es)	1979-12-28
NZ182428A (en)	1978-11-13
SE7611954L (sv)	1977-04-29
FR2329270A1 (fr)	1977-05-27
DE2647864C2 (de)	1985-04-25
JPS5253852A (en)	1977-04-30
PT65753B (en)	1978-04-20
BE847718A (fr)	1977-04-28
MX3972E (es)	1981-10-20
IL50413A0 (en)	1976-11-30

Legal Events

Date	Code	Title	Description
1987-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2647907C2 (de)	1985-01-24	2-Phenyl-3-aroylbenzothiophene und Verfahren zu ihrer Herstellung
DE2647864C2 (de)	1985-04-25	2-Aroyl-3-phenylbenzothiophenverbindungen und Verfahren zu ihrer Herstellung
EP0004279B1 (de)	1982-12-29	Verfahren zur Herstellung von 4-Pyridon-3-carbonsäuren, 1-Cyclopropyl-4-Pyridon-3-Carbonsäurederivate und diese enthaltende Arzneimittel
DE2165260A1 (de)	1972-07-27	Verfahren zur Herstellung von N-substituierten Dibenzo eckige Klammer auf b,f eckige Klammer zu thiepin-10-methylaminen und zugehörige neue Zwischenprodukte
DE1695836A1 (de)	1971-05-13	Substituierte Piperidinoalkylthianaphthene und -benzofurane
CH626045A5 (cs)	1981-10-30
CH642077A5 (de)	1984-03-30	3-fluor-10-piperazino-8-substituierte 10,11-dihydrodibenzo-(b,f)-thiepine, deren saeureadditionssalze, verfahren zur herstellung derselben und diese enthaltende zubereitungen.
DE1618465C3 (de)	1979-05-31	Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2647906C2 (de)	1985-01-31	Aroylphenylindene und Aroylphenylnaphthaline und -hydronaphthaline sowie Verfahren zu ihrer Herstellung
DE1816845A1 (de)	1969-08-28	2-Cycloalkyl-1-phenyldihydronaphthaline und -tetrahydronaphthaline sowie Verfahren zur Herstellung derselben
DE2645865C2 (cs)	1988-07-07
DE1493855C3 (de)	1975-05-22	1- eckige Klammer auf p-(Dialkylaminoalkoxy)-phenyl eckige Klammer zu -i-phenyl-2-phenyl-n-alkane und Verfahren zu deren Herstellung
DE1695963A1 (de)	1971-05-19	Cycloalkenamin-p-benzochinonaddukte und Verfahren zu ihrer Herstellung
DE1695962A1 (de)	1971-05-19	(2-Aminocycloalkyl)hydrochinone und Derivate derselben sowie Verfahren zu ihrer Herstellung
CH624398A5 (en)	1981-07-31	Process for the preparation of aroylphenylnaphthalenes
DE1670386A1 (de)	1970-11-05	Neue Cyclohexanderivate und Verfahren zu ihrer Herstellung
DE1942521A1 (de)	1970-02-26	Cyclopropancarbonsaeurederivate und Verfahren zu deren Herstellung
DE2448454C2 (de)	1985-08-29	1-Oxo-5-indanyloxyalkylcarbonsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3641907A1 (de)	1987-06-11	4h-benzo(4,5)cyclohepta(1,2-b)thiophen derivate
DE2151487A1 (de)	1972-04-20	Pharmazeutische Massen
DE1568848B2 (de)	1974-10-31	Trans-Isomere von Alkenderivaten und Verfahren zu ihrer Herstellung
AT244327B (de)	1965-12-27	Verfahren zur Herstellung von Diphenylalkylaminen und ihren physiologisch verträglichen Salzen
AT367030B (de)	1982-05-25	Verfahren zur herstellung von neuen benzoesaeure- derivaten und deren estern und salzen
AT359479B (de)	1980-11-10	Verfahren zur herstellung von neuen benzoe- saeuren und deren estern und salzen
DE3217446A1 (de)	1983-11-24	Substituierte thiocarbamoyl-thenoylacetonitrile, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate