NO852760L - Fremgangsmaate ved fremstilling av benzotiofenderivater - Google Patents
Fremgangsmaate ved fremstilling av benzotiofenderivaterInfo
- Publication number
- NO852760L NO852760L NO852760A NO852760A NO852760L NO 852760 L NO852760 L NO 852760L NO 852760 A NO852760 A NO 852760A NO 852760 A NO852760 A NO 852760A NO 852760 L NO852760 L NO 852760L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- thiophene
- phenyl
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 46
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- YVTSCBBDSXVLNL-UHFFFAOYSA-N 3-phenyl-1-benzothiophene-2-carbaldehyde Chemical compound O=CC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 YVTSCBBDSXVLNL-UHFFFAOYSA-N 0.000 claims description 6
- -1 halogen ion Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- SSLURIRZNIDSSG-UHFFFAOYSA-M 3-(dimethylamino)propyl-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCN(C)C)C1=CC=CC=C1 SSLURIRZNIDSSG-UHFFFAOYSA-M 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- MYCORMJNIFJWQW-UHFFFAOYSA-N n,n-dimethyl-4-(3-phenyl-1-benzothiophen-2-yl)butan-1-amine Chemical compound CN(C)CCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 MYCORMJNIFJWQW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 36
- 239000000203 mixture Substances 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 206010012735 Diarrhoea Diseases 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 101710146739 Enterotoxin Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000147 enterotoxin Substances 0.000 description 4
- 231100000655 enterotoxin Toxicity 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 3
- WFMKJINLRUEQIP-UHFFFAOYSA-N 5-(3-phenyl-1-benzothiophen-2-yl)pentan-1-amine Chemical compound NCCCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 WFMKJINLRUEQIP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000003891 oxalate salts Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HZYRPUKLUAUOMF-UHFFFAOYSA-N 3-phenyl-1-benzothiophene Chemical class C=1SC2=CC=CC=C2C=1C1=CC=CC=C1 HZYRPUKLUAUOMF-UHFFFAOYSA-N 0.000 description 2
- AWMNCTJZVNZUDD-UHFFFAOYSA-N 3-phenyl-1-benzothiophene-7-carbaldehyde Chemical compound C=1SC=2C(C=O)=CC=CC=2C=1C1=CC=CC=C1 AWMNCTJZVNZUDD-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- SGZTXFPUYUJKCD-UHFFFAOYSA-N 5-(3-phenyl-1-benzothiophen-2-yl)pentanenitrile Chemical compound N#CCCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 SGZTXFPUYUJKCD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001142 anti-diarrhea Effects 0.000 description 2
- 229940125714 antidiarrheal agent Drugs 0.000 description 2
- 239000003793 antidiarrheal agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
- LRXAUPDKGXIRKM-UHFFFAOYSA-N 1-[4-(3-phenyl-1-benzothiophen-2-yl)but-3-enyl]piperidine Chemical compound S1C2=CC=CC=C2C(C=2C=CC=CC=2)=C1C=CCCN1CCCCC1 LRXAUPDKGXIRKM-UHFFFAOYSA-N 0.000 description 1
- PCGAPOZFJFUPAT-UHFFFAOYSA-N 1-[4-(3-phenyl-1-benzothiophen-2-yl)but-3-enyl]piperidine;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2C(C=2C=CC=CC=2)=C1C=CCCN1CCCCC1 PCGAPOZFJFUPAT-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- OSMIKBUMHDSMJT-UHFFFAOYSA-M 2-(dimethylamino)ethyl-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCN(C)C)C1=CC=CC=C1 OSMIKBUMHDSMJT-UHFFFAOYSA-M 0.000 description 1
- SRWDQSRTOOMPMO-UHFFFAOYSA-N 3-bromo-1-benzothiophene Chemical compound C1=CC=C2C(Br)=CSC2=C1 SRWDQSRTOOMPMO-UHFFFAOYSA-N 0.000 description 1
- PAOHMIPLGDOHBB-UHFFFAOYSA-M 3-cyanopropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC#N)C1=CC=CC=C1 PAOHMIPLGDOHBB-UHFFFAOYSA-M 0.000 description 1
- CINUJWAAXPLQFV-UHFFFAOYSA-N 4-phenyl-1-benzothiophene-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=CC2=C1C1=CC=CC=C1 CINUJWAAXPLQFV-UHFFFAOYSA-N 0.000 description 1
- HKVDSIRXJQVORE-UHFFFAOYSA-N 5-(3-phenyl-1-benzothiophen-2-yl)pent-4-enenitrile Chemical compound N#CCCC=CC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 HKVDSIRXJQVORE-UHFFFAOYSA-N 0.000 description 1
- BTJRSKLOPVFSCP-UHFFFAOYSA-N 5-bromo-3-phenyl-1-benzothiophene-2-carbaldehyde Chemical compound C12=CC(Br)=CC=C2SC(C=O)=C1C1=CC=CC=C1 BTJRSKLOPVFSCP-UHFFFAOYSA-N 0.000 description 1
- QMAOBCYAEIOEKC-UHFFFAOYSA-N 7-(bromomethyl)-3-phenyl-1-benzothiophene Chemical compound C=1SC=2C(CBr)=CC=CC=2C=1C1=CC=CC=C1 QMAOBCYAEIOEKC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SGFMKLOIJMTZBK-UHFFFAOYSA-N CC1=CC=C(S(O)(=O)=O)C=C1.CN(C)CCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CN(C)CCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 SGFMKLOIJMTZBK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000032754 Infant Death Diseases 0.000 description 1
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000006007 Sommelet synthesis reaction Methods 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
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- 231100000517 death Toxicity 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000002011 intestinal secretion Anatomy 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- OPUXBILHXPFJHX-UHFFFAOYSA-N n,n-dimethyl-3-(3-phenyl-1-benzothiophen-2-yl)prop-2-en-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CC=CC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 OPUXBILHXPFJHX-UHFFFAOYSA-N 0.000 description 1
- WPXSGMODSFBMEQ-UHFFFAOYSA-N n,n-dimethyl-3-(3-phenyl-1-benzothiophen-2-yl)propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 WPXSGMODSFBMEQ-UHFFFAOYSA-N 0.000 description 1
- HEWFKELMQZRCKD-UHFFFAOYSA-N n,n-dimethyl-4-(3-phenyl-1-benzothiophen-2-yl)but-3-en-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCC=CC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 HEWFKELMQZRCKD-UHFFFAOYSA-N 0.000 description 1
- FZIBHQDTPXQRGZ-UHFFFAOYSA-N n,n-dimethyl-5-(3-phenyl-1-benzothiophen-2-yl)pentan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCCCC=1SC2=CC=CC=C2C=1C1=CC=CC=C1 FZIBHQDTPXQRGZ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 208000026775 severe diarrhea Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- JREQLVFLFVWQIA-UHFFFAOYSA-M triphenyl(3-piperidin-1-ylpropyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCN1CCCCC1 JREQLVFLFVWQIA-UHFFFAOYSA-M 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- C07D333/54—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
- C07D333/58—Radicals substituted by nitrogen 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
- C07D333/54—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
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848417559A GB8417559D0 (en) | 1984-07-10 | 1984-07-10 | Anti-diarrhoeal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852760L true NO852760L (no) | 1986-01-13 |
Family
ID=10563672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852760A NO852760L (no) | 1984-07-10 | 1985-07-09 | Fremgangsmaate ved fremstilling av benzotiofenderivater |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4654352A (ja) |
| EP (1) | EP0169012A1 (ja) |
| JP (1) | JPS6136281A (ja) |
| KR (1) | KR860001094A (ja) |
| CN (1) | CN85105193A (ja) |
| AU (1) | AU556058B2 (ja) |
| CS (1) | CS249545B2 (ja) |
| DD (1) | DD238792A5 (ja) |
| DK (1) | DK312485A (ja) |
| ES (1) | ES8604557A1 (ja) |
| FI (1) | FI852691L (ja) |
| GB (1) | GB8417559D0 (ja) |
| GR (1) | GR851688B (ja) |
| HU (1) | HUT38330A (ja) |
| IL (1) | IL75740A0 (ja) |
| NO (1) | NO852760L (ja) |
| PL (1) | PL254445A1 (ja) |
| PT (1) | PT80786B (ja) |
| YU (1) | YU113985A (ja) |
| ZA (1) | ZA855153B (ja) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4128690A1 (de) * | 1991-08-29 | 1993-03-04 | Boehringer Mannheim Gmbh | Bicyclische sulfone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| ATE214059T1 (de) * | 1994-04-11 | 2002-03-15 | Chugai Pharmaceutical Co Ltd | 4,6-di-t-butyl-2,3-dihydrobenzothiophene, die ldl oxidation hemmen |
| CA2207141A1 (en) * | 1996-07-15 | 1998-01-15 | David Thompson Berg | Benzothiophene compounds, and uses and formulations thereof |
| CA2207083A1 (en) * | 1996-07-15 | 1998-01-15 | Brian William Grinnell | Benzothiophene compounds, and uses and formulations thereof |
| US5792798A (en) * | 1996-07-29 | 1998-08-11 | Eli Lilly And Company | Method for inhibiting plasminogen activator inhibitor 1 |
| CN1251577A (zh) * | 1997-02-21 | 2000-04-26 | 武田药品工业株式会社 | 稠环化合物及其生产和应用 |
| BR9911779A (pt) * | 1998-05-12 | 2001-02-06 | American Home Prod | Benzotiofenos, benzofuranos e indóis úteis no tratamento de resistência à insulina e hiperglicemia |
| US6251936B1 (en) | 1998-05-12 | 2001-06-26 | American Home Products Corporation | Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia |
| MXPA03003845A (es) * | 2000-11-02 | 2003-07-28 | Hoffmann La Roche | Benzo'b! tiofenos y benzo'd! isotiazoles bajos en colesterol. |
| US6969730B2 (en) | 2001-03-16 | 2005-11-29 | Abbott Laboratories | Amines as histamine-3 receptor ligands and their therapeutic applications |
| US7393865B2 (en) * | 2004-06-17 | 2008-07-01 | Neurocrine Biosciences, Inc. | Sleep inducing compounds and methods relating thereto |
| JP5180807B2 (ja) | 2008-12-24 | 2013-04-10 | 三菱重工業株式会社 | １段静翼の冷却構造、及びガスタービン |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1174411A (en) * | 1966-03-02 | 1969-12-17 | Aspro Nicholas Ltd | Novel Benzothiophen Compounds, Compositions containing them and processes for their manufacture |
| US3598839A (en) * | 1969-06-30 | 1971-08-10 | Parke Davis & Co | Phenylbenzothiophene compounds |
| US3944672A (en) * | 1972-12-13 | 1976-03-16 | Schering Corporation | Method for treating microbial infections |
| ZA753324B (en) * | 1974-05-28 | 1976-04-28 | Scherico Ltd | Antimicrobial compounds and compositions containing them |
| US4018893A (en) * | 1974-05-28 | 1977-04-19 | Schering Corporation | Methods for treating microbial infections |
| US4137414A (en) * | 1977-09-26 | 1979-01-30 | G. D. Searle & Co. | 5-Substituted-2-phenylbenzo[b]thiophene-3-alkylamines and related compounds |
-
1984
- 1984-07-10 GB GB848417559A patent/GB8417559D0/en active Pending
-
1985
- 1985-06-28 US US06/750,115 patent/US4654352A/en not_active Expired - Lifetime
- 1985-07-05 EP EP85304793A patent/EP0169012A1/en not_active Withdrawn
- 1985-07-08 PL PL25444585A patent/PL254445A1/xx unknown
- 1985-07-08 IL IL75740A patent/IL75740A0/xx unknown
- 1985-07-08 CN CN198585105193A patent/CN85105193A/zh active Pending
- 1985-07-08 GR GR851688A patent/GR851688B/el unknown
- 1985-07-08 ES ES544970A patent/ES8604557A1/es not_active Expired
- 1985-07-08 PT PT80786A patent/PT80786B/pt unknown
- 1985-07-08 CS CS855105A patent/CS249545B2/cs unknown
- 1985-07-08 FI FI852691A patent/FI852691L/fi not_active Application Discontinuation
- 1985-07-09 JP JP15117785A patent/JPS6136281A/ja active Pending
- 1985-07-09 DK DK312485A patent/DK312485A/da not_active Application Discontinuation
- 1985-07-09 KR KR1019850004875A patent/KR860001094A/ko not_active Application Discontinuation
- 1985-07-09 DD DD85278412A patent/DD238792A5/de unknown
- 1985-07-09 YU YU01139/85A patent/YU113985A/xx unknown
- 1985-07-09 NO NO852760A patent/NO852760L/no unknown
- 1985-07-09 AU AU44713/85A patent/AU556058B2/en not_active Ceased
- 1985-07-09 ZA ZA855153A patent/ZA855153B/xx unknown
- 1985-07-09 HU HU852658A patent/HUT38330A/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8604557A1 (es) | 1986-02-01 |
| CS249545B2 (en) | 1987-03-12 |
| GB8417559D0 (en) | 1984-08-15 |
| DK312485D0 (da) | 1985-07-09 |
| DD238792A5 (de) | 1986-09-03 |
| AU556058B2 (en) | 1986-10-23 |
| YU113985A (en) | 1987-08-31 |
| ES544970A0 (es) | 1986-02-01 |
| GR851688B (ja) | 1985-11-26 |
| JPS6136281A (ja) | 1986-02-20 |
| US4654352A (en) | 1987-03-31 |
| FI852691L (fi) | 1986-01-11 |
| KR860001094A (ko) | 1986-02-22 |
| IL75740A0 (en) | 1985-11-29 |
| ZA855153B (en) | 1987-02-25 |
| AU4471385A (en) | 1986-01-16 |
| PT80786B (en) | 1987-03-26 |
| DK312485A (da) | 1986-01-11 |
| EP0169012A1 (en) | 1986-01-22 |
| HUT38330A (en) | 1986-05-28 |
| PT80786A (en) | 1985-08-01 |
| CN85105193A (zh) | 1987-01-28 |
| FI852691A0 (fi) | 1985-07-08 |
| PL254445A1 (en) | 1986-07-15 |
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