CS205047B2 - Method of producing novel 2-phenyl-3-aroylbenzothiophenone derivatives - Google Patents

Method of producing novel 2-phenyl-3-aroylbenzothiophenone derivatives Download PDF

Info

Publication number: CS205047B2
Authority: CS; Czechoslovakia
Prior art keywords: compound; hydrogen; group; alkoxy; hydroxy
Prior art date: 1975-10-28

Application number

CS766974A

Other languages

Czech (cs)

English (en)

Inventor

Charles D 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

1976-10-28

Publication date

1981-04-30

1976-10-28 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-04-30 Publication of CS205047B2 publication Critical patent/CS205047B2/cs

Links

238000000034 method Methods 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 91
229910052739 hydrogen Inorganic materials 0.000 claims description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 14
-1 benzoyloxy, adamantoyloxy Chemical group 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 12
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
LBMHPHUSGIEGHJ-UHFFFAOYSA-N 2-phenyl-1-benzothiophene Chemical class S1C2=CC=CC=C2C=C1C1=CC=CC=C1 LBMHPHUSGIEGHJ-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000003462 sulfoxides Chemical class 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
239000003433 contraceptive agent Substances 0.000 abstract description 3
206010006187 Breast cancer Diseases 0.000 abstract 1
239000000203 mixture Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000000047 product Substances 0.000 description 21
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 15
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
230000035558 fertility Effects 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
241000282421 Canidae Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000013543 active substance Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229920000137 polyphosphoric acid Polymers 0.000 description 4
238000004237 preparative chromatography Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
230000003509 anti-fertility effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000002285 corn oil Substances 0.000 description 3
235000005687 corn oil Nutrition 0.000 description 3
238000006317 isomerization reaction Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000004949 mass spectrometry Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
ADEABUBJWLQXHT-UHFFFAOYSA-N (6-hydroxy-2-phenyl-1-benzothiophen-3-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1SC2=CC(O)=CC=C2C=1C(=O)C1=CC=CC=C1 ADEABUBJWLQXHT-UHFFFAOYSA-N 0.000 description 2
HTIWXTLOMXKPQC-UHFFFAOYSA-N (6-methoxy-2-phenyl-1-benzothiophen-3-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1SC2=CC(OC)=CC=C2C=1C(=O)C1=CC=CC=C1 HTIWXTLOMXKPQC-UHFFFAOYSA-N 0.000 description 2
PANZFQYXPMCHFD-UHFFFAOYSA-N 2,3-diphenyl-1h-indene Chemical class C12=CC=CC=C2CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PANZFQYXPMCHFD-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
NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
YPILCKZLXTVGPW-UHFFFAOYSA-N 6-methoxy-2-phenyl-1-benzothiophene-3-carboxylic acid Chemical compound S1C2=CC(OC)=CC=C2C(C(O)=O)=C1C1=CC=CC=C1 YPILCKZLXTVGPW-UHFFFAOYSA-N 0.000 description 2
241000271566 Aves Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000003637 steroidlike Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
AFYHZAHUQTZQBC-UHFFFAOYSA-N (4-hydroxyphenyl)-(6-hydroxy-2-phenyl-1-benzothiophen-3-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)SC2=CC(O)=CC=C12 AFYHZAHUQTZQBC-UHFFFAOYSA-N 0.000 description 1
BUTKDFXHZXSXAY-UHFFFAOYSA-N (4-methoxyphenyl)-(6-methoxy-2-phenyl-1-benzothiophen-3-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)SC2=CC(OC)=CC=C12 BUTKDFXHZXSXAY-UHFFFAOYSA-N 0.000 description 1
XHQBIYCRFVVHFD-UHFFFAOYSA-N 1-benzothiophen-3-ol Chemical compound C1=CC=C2C(O)=CSC2=C1 XHQBIYCRFVVHFD-UHFFFAOYSA-N 0.000 description 1
FRJNKYGTHPUSJR-UHFFFAOYSA-N 1-benzothiophene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)C=CC2=C1 FRJNKYGTHPUSJR-UHFFFAOYSA-N 0.000 description 1
FNJAWWOVTKGZCV-UHFFFAOYSA-N 1-benzothiophene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(=O)O)SC2=C1 FNJAWWOVTKGZCV-UHFFFAOYSA-N 0.000 description 1
MRLUWCIEBHJONW-UHFFFAOYSA-N 1-phenyl-2-phenylsulfanylethanone Chemical compound C=1C=CC=CC=1C(=O)CSC1=CC=CC=C1 MRLUWCIEBHJONW-UHFFFAOYSA-N 0.000 description 1
YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
ADKCFCOXELVRJV-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-benzothiophene Chemical compound C1=CC(OC)=CC=C1C1=CC2=CC=CC=C2S1 ADKCFCOXELVRJV-UHFFFAOYSA-N 0.000 description 1
XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical compound OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
NIYAPGAPUFVRRF-UHFFFAOYSA-N 5-(benzylsulfanylmethyl)-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CSCC1=CC=CC=C1 NIYAPGAPUFVRRF-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
IWVUZJFFOKPQLJ-UHFFFAOYSA-N 6-hydroxy-2-(4-methylsulfanylphenyl)chromen-4-one Chemical compound C1=CC(SC)=CC=C1C1=CC(=O)C2=CC(O)=CC=C2O1 IWVUZJFFOKPQLJ-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000272201 Columbiformes Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
244000297179 Syringa vulgaris Species 0.000 description 1
235000004338 Syringa vulgaris Nutrition 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
VJWQKBDLTVGKQE-UHFFFAOYSA-N benzene;cadmium(2+) Chemical compound [Cd+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 VJWQKBDLTVGKQE-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
230000002401 inhibitory effect Effects 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
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
108700029318 rat female Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio 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
- C07D333/64—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

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

CS766974A 1975-10-28 1976-10-28 Method of producing novel 2-phenyl-3-aroylbenzothiophenone derivatives CS205047B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US62601075A	1975-10-28	1975-10-28

Publications (1)

Publication Number	Publication Date
CS205047B2 true CS205047B2 (en)	1981-04-30

Family

ID=24508581

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS766974A CS205047B2 (en)	1975-10-28	1976-10-28	Method of producing novel 2-phenyl-3-aroylbenzothiophenone derivatives
CS766974A CS205046B2 (en)	1975-10-28	1976-10-28	Method of producing new 2-phenyl-3-aroylbenzothiophenone derivatives

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS766974A CS205046B2 (en)	1975-10-28	1976-10-28	Method of producing new 2-phenyl-3-aroylbenzothiophenone derivatives

Country Status (31)

Country	Link
US (1)	US4133814A (de)
JP (1)	JPS5253851A (de)
AR (3)	AR222959A1 (de)
AT (1)	AT357520B (de)
AU (1)	AU505360B2 (de)
BE (1)	BE847719A (de)
BG (2)	BG28065A4 (de)
CA (1)	CA1090795A (de)
CH (3)	CH635336A5 (de)
CS (2)	CS205047B2 (de)
DD (1)	DD127461A5 (de)
DE (1)	DE2647907C2 (de)
DK (1)	DK152045C (de)
ES (2)	ES452694A1 (de)
FR (1)	FR2329271A1 (de)
GB (1)	GB1570610A (de)
GR (1)	GR61776B (de)
HU (1)	HU179012B (de)
IE (1)	IE44392B1 (de)
IL (1)	IL50773A (de)
MX (1)	MX4584E (de)
NL (1)	NL7611975A (de)
NZ (1)	NZ182429A (de)
PH (1)	PH14219A (de)
PL (2)	PL107979B1 (de)
PT (1)	PT65755B (de)
RO (1)	RO70769A (de)
SE (1)	SE426945B (de)
SU (2)	SU701539A3 (de)
YU (1)	YU262076A (de)
ZA (1)	ZA766440B (de)

Families Citing this family (308)

* Cited by examiner, † Cited by third party
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1976
- 1976-09-17 US US05/724,203 patent/US4133814A/en not_active Expired - Lifetime
- 1976-10-08 JP JP51121787A patent/JPS5253851A/ja active Granted
- 1976-10-15 HU HU76EI707A patent/HU179012B/hu unknown
- 1976-10-21 MX MX7614994U patent/MX4584E/es unknown
- 1976-10-21 CA CA263,844A patent/CA1090795A/en not_active Expired
- 1976-10-22 DE DE2647907A patent/DE2647907C2/de not_active Expired
- 1976-10-25 GB GB44188/76A patent/GB1570610A/en not_active Expired
- 1976-10-25 SU SU762414465A patent/SU701539A3/ru active
- 1976-10-25 ES ES452694A patent/ES452694A1/es not_active Expired
- 1976-10-25 PT PT65755A patent/PT65755B/pt unknown
- 1976-10-25 GR GR52005A patent/GR61776B/el unknown
- 1976-10-25 ES ES452695A patent/ES452695A1/es not_active Expired
- 1976-10-26 SU SU762414462A patent/SU764610A3/ru active
- 1976-10-26 RO RO7688224A patent/RO70769A/ro unknown
- 1976-10-26 AU AU19005/76A patent/AU505360B2/en not_active Expired
- 1976-10-27 NZ NZ182429A patent/NZ182429A/xx unknown
- 1976-10-27 IL IL50773A patent/IL50773A/xx unknown
- 1976-10-27 DK DK484876A patent/DK152045C/da not_active IP Right Cessation
- 1976-10-27 CH CH1355676A patent/CH635336A5/de not_active IP Right Cessation
- 1976-10-27 PL PL1976193308A patent/PL107979B1/pl unknown
- 1976-10-27 YU YU02620/76A patent/YU262076A/xx unknown
- 1976-10-27 PL PL1976212113A patent/PL114190B1/pl unknown
- 1976-10-27 ZA ZA00766440A patent/ZA766440B/xx unknown
- 1976-10-27 IE IE2372/76A patent/IE44392B1/en unknown
- 1976-10-27 SE SE7611955A patent/SE426945B/xx not_active IP Right Cessation
- 1976-10-28 BG BG036899A patent/BG28065A4/xx unknown
- 1976-10-28 BE BE1007725A patent/BE847719A/xx not_active IP Right Cessation
- 1976-10-28 DD DD195508A patent/DD127461A5/xx unknown
- 1976-10-28 AT AT800876A patent/AT357520B/de not_active IP Right Cessation
- 1976-10-28 CS CS766974A patent/CS205047B2/cs unknown
- 1976-10-28 FR FR7632514A patent/FR2329271A1/fr active Granted
- 1976-10-28 CS CS766974A patent/CS205046B2/cs unknown
- 1976-10-28 AR AR265277A patent/AR222959A1/es active
- 1976-10-28 BG BG034550A patent/BG27553A3/xx unknown
- 1976-10-28 NL NL7611975A patent/NL7611975A/xx not_active Application Discontinuation
1978
- 1978-05-12 AR AR272153A patent/AR222796A1/es active
- 1978-05-12 AR AR272154A patent/AR215930A1/es active
1979
- 1979-06-15 PH PH22655A patent/PH14219A/en unknown
1982
- 1982-01-11 CH CH13982A patent/CH635582A5/de not_active IP Right Cessation
- 1982-11-15 CH CH25582A patent/CH634316A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA1090795A (en)	1980-12-02
PH14219A (en)	1981-04-02
CH635582A5 (de)	1983-04-15
DK152045B (da)	1988-01-25
SE426945B (sv)	1983-02-21
NL7611975A (nl)	1977-05-02
HU179012B (en)	1982-08-28
ZA766440B (en)	1978-06-28
PT65755A (en)	1976-11-01
DD127461A5 (de)	1977-09-28
IL50773A (en)	1980-03-31
SU764610A3 (ru)	1980-09-15
PL114190B1 (en)	1981-01-31
CS205046B2 (en)	1981-04-30
ES452694A1 (es)	1977-11-16
IE44392B1 (en)	1981-11-18
ATA800876A (de)	1979-12-15
MX4584E (es)	1982-06-25
US4133814A (en)	1979-01-09
AU505360B2 (en)	1979-11-15
BE847719A (fr)	1977-04-28
JPS5253851A (en)	1977-04-30
CH635336A5 (de)	1983-03-31
NZ182429A (en)	1978-11-13
AU1900576A (en)	1978-05-04
DE2647907C2 (de)	1985-01-24
GB1570610A (en)	1980-07-02
GR61776B (en)	1979-01-16
AR222796A1 (es)	1981-06-30
DK484876A (da)	1977-04-29
SE7611955L (sv)	1977-04-29
AR215930A1 (es)	1979-11-15
BG27553A3 (en)	1979-11-12
IE44392L (en)	1977-04-28
FR2329271A1 (fr)	1977-05-27
DE2647907A1 (de)	1977-05-12
AT357520B (de)	1980-07-10
ES452695A1 (es)	1977-11-16
YU262076A (en)	1983-01-21
JPS61343B2 (de)	1986-01-08
BG28065A4 (en)	1980-02-25
SU701539A3 (ru)	1979-11-30
DK152045C (da)	1988-06-20
IL50773A0 (en)	1976-12-31
AR222959A1 (es)	1981-07-15
RO70769A (ro)	1982-10-26
PL193308A1 (pl)	1978-03-28
CH634316A5 (de)	1983-01-31
PL107979B1 (pl)	1980-03-31
PT65755B (en)	1978-04-27
FR2329271B1 (de)	1979-07-27

Publication	Publication Date	Title
CS205046B2 (en)	1981-04-30	Method of producing new 2-phenyl-3-aroylbenzothiophenone derivatives
US4418068A (en)	1983-11-29	Antiestrogenic and antiandrugenic benzothiophenes
GB2097788A (en)	1982-11-10	Benzothiophene compounds and process for preparing them
CS196328B2 (en)	1980-03-31	Method of preparing novel derivatives of 2-aroyl-3-phenyl-benzothiophene
CZ285937B6 (cs)	1999-12-15	Arylcykloalkylové deriváty, způsob přípravy těchto derivátů a jejich použití
EA004931B1 (ru)	2004-10-28	3, 4, 5-тризамещенные арилнитроны и содержащие их фармацевтические композиции
CS196305B2 (en)	1980-03-31	Process for preparing derivatives of benzophenones
US4229467A (en)	1980-10-21	Alkoxy benzofuran carboxylic acids and salts and esters thereof as hypolipidemic agents
CZ189295A3 (en)	1996-02-14	Process of enhanced preparation of 3-(4-aminoethoxy-benzoyl)benzo/b/-thiophenes
US4153719A (en)	1979-05-08	Aromatic diketones
KR880001320B1 (ko)	1988-07-23	2-시클릭아미노-2-(1, 2-벤지속사졸-3-일)아세트산 에스테르 유도체들의 제조방법
US4154743A (en)	1979-05-15	3-Oxobenzofuranyl-2-idenyl, haloacetic acids
US4075223A (en)	1978-02-21	Novel antifertility agents
CA1204440A (en)	1986-05-13	Isoxazole¬5,4-b\|pyridines
US4000307A (en)	1976-12-28	Alkanoyl isoindolinylmethyl alkylphenones
PL111987B1 (en)	1980-09-30	Method of preparation of novel derivatives of aroylphenylonaphthalenes
JPS5929077B2 (ja)	1984-07-18	プロスタグランジン−ブロツキング活性を有するフエニル−およびベンジルホスホネ−トエステル
US4171371A (en)	1979-10-16	Diketones
GB2212153A (en)	1989-07-19	Phenyl hydroxamic acids
US4283404A (en)	1981-08-11	Aroylethenylpiperidinobutyrophenone antipsychotic agents
US4284636A (en)	1981-08-18	Cinnamoylpiperidinobutyrophenone antipsychotic agents
NO171499B (no)	1992-12-14	Analogifremgangsmaate for fremstilling av terapeutisk aktive 5,6-dihydro-4h-cyklo-penta(b)tiofen-6-karboksylsyre-derivater
KR800001036B1 (ko)	1980-09-26	새로운 항수정제의 제조방법
PL146350B1 (en)	1989-01-31	Method of obtaining oxazine(5,6-c)1,2-benzothiazine
US5508280A (en)	1996-04-16	5H-Dibenzo (A,D) cycloheptenes as muscarinic receptor antagonists