KR100190673B1 - 벤조푸란, 벤조 티오펜, 인돌 및 인돌리진의 유도체, 그것들의 제조방법 및 그것들을 함유한 조성물 - Google Patents
벤조푸란, 벤조 티오펜, 인돌 및 인돌리진의 유도체, 그것들의 제조방법 및 그것들을 함유한 조성물 Download PDFInfo
- Publication number
- KR100190673B1 KR100190673B1 KR1019910013726A KR910013726A KR100190673B1 KR 100190673 B1 KR100190673 B1 KR 100190673B1 KR 1019910013726 A KR1019910013726 A KR 1019910013726A KR 910013726 A KR910013726 A KR 910013726A KR 100190673 B1 KR100190673 B1 KR 100190673B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- benzoyl
- derivative
- compound
- general formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 18
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 title claims abstract description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 53
- 238000002360 preparation method Methods 0.000 title description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 203
- -1 indolizin compound Chemical class 0.000 claims abstract description 117
- 210000000748 cardiovascular system Anatomy 0.000 claims abstract description 5
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 153
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 128
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 99
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 74
- 229910052721 tungsten Inorganic materials 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 38
- 239000012458 free base Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 34
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 32
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 150000007524 organic acids Chemical class 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 150000007522 mineralic acids Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- ZQTNQVWKHCQYLQ-UHFFFAOYSA-N dronedarone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 ZQTNQVWKHCQYLQ-UHFFFAOYSA-N 0.000 claims description 8
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 8
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910003445 palladium oxide Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- VIHDVFYVOLNGJX-UHFFFAOYSA-N (5-amino-2-butyl-1h-indol-3-yl)-[4-[3-(dibutylamino)propoxy]phenyl]methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)NC2=CC=C(N)C=C12 VIHDVFYVOLNGJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- KAGOEWVNTGUFGW-UHFFFAOYSA-N indolizine-1-carboxylic acid Chemical class C1=CC=CC2=C(C(=O)O)C=CN21 KAGOEWVNTGUFGW-UHFFFAOYSA-N 0.000 claims 1
- AUIPWLGKEGFMNJ-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-propan-2-yl-1-benzofuran-5-yl]methanesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(C(C)C)OC2=CC=C(NS(C)(=O)=O)C=C12 AUIPWLGKEGFMNJ-UHFFFAOYSA-N 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 239
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 238000004128 high performance liquid chromatography Methods 0.000 description 95
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 82
- 229940093499 ethyl acetate Drugs 0.000 description 80
- 235000019439 ethyl acetate Nutrition 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 69
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000377 silicon dioxide Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000004587 chromatography analysis Methods 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000003480 eluent Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 230000036982 action potential Effects 0.000 description 10
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OVJKFJDEVKABNF-UHFFFAOYSA-N 2-butyl-1-benzofuran Chemical compound C1=CC=C2OC(CCCC)=CC2=C1 OVJKFJDEVKABNF-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
- SPIIBUQYWNFELT-UHFFFAOYSA-N (5-amino-2-butyl-1-benzofuran-3-yl)-[4-[3-(dibutylamino)propoxy]phenyl]methanone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(N)C=C12 SPIIBUQYWNFELT-UHFFFAOYSA-N 0.000 description 7
- XGAJABPTUOLUAE-UHFFFAOYSA-N 2-butyl-5-nitro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC(CCCC)=CC2=C1 XGAJABPTUOLUAE-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229960005260 amiodarone Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 210000004413 cardiac myocyte Anatomy 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- RGPUXXZXJIPTFR-UHFFFAOYSA-N 2-butyl-1-methyl-5-nitroindole Chemical compound [O-][N+](=O)C1=CC=C2N(C)C(CCCC)=CC2=C1 RGPUXXZXJIPTFR-UHFFFAOYSA-N 0.000 description 5
- OPYVJLHNHMDRKU-UHFFFAOYSA-N 2-butyl-5-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=C2NC(CCCC)=CC2=C1 OPYVJLHNHMDRKU-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 206010003119 arrhythmia Diseases 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229940050411 fumarate Drugs 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- ANLMKUQEPXRMGV-UHFFFAOYSA-N n-butyl-n-(3-chloropropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCCCl ANLMKUQEPXRMGV-UHFFFAOYSA-N 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
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- ZQWCWZUDQFYETN-UHFFFAOYSA-N n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1h-indol-5-yl]methanesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)NC2=CC=C(NS(C)(=O)=O)C=C12 ZQWCWZUDQFYETN-UHFFFAOYSA-N 0.000 description 1
- JKHWBDFITAJDCJ-UHFFFAOYSA-N n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1h-indol-5-yl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)NC2=CC=C(NS(C)(=O)=O)C=C12 JKHWBDFITAJDCJ-UHFFFAOYSA-N 0.000 description 1
- TZRRDASVYWEXQR-UHFFFAOYSA-N n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]indolizin-7-yl]-2-methylbenzenesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)C=C2N1C=CC(NS(=O)(=O)C=1C(=CC=CC=1)C)=C2 TZRRDASVYWEXQR-UHFFFAOYSA-N 0.000 description 1
- FYMRDEBSASDNDG-UHFFFAOYSA-N n-[2-butyl-3-[4-[3-(diethylamino)propoxy]benzoyl]-1-benzofuran-5-yl]methanesulfonamide Chemical compound CCCCC=1OC2=CC=C(NS(C)(=O)=O)C=C2C=1C(=O)C1=CC=C(OCCCN(CC)CC)C=C1 FYMRDEBSASDNDG-UHFFFAOYSA-N 0.000 description 1
- XRSIPYRSCQMROF-UHFFFAOYSA-N n-[2-butyl-3-[4-[5-(dibutylamino)pentoxy]benzoyl]-1-benzofuran-5-yl]methanesulfonamide Chemical compound C1=CC(OCCCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 XRSIPYRSCQMROF-UHFFFAOYSA-N 0.000 description 1
- MUJWUMPNQKTCJR-UHFFFAOYSA-N n-[2-butyl-3-[[4-[3-(dibutylamino)propoxy]phenyl]methyl]-1-benzofuran-5-yl]methanesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1CC1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 MUJWUMPNQKTCJR-UHFFFAOYSA-N 0.000 description 1
- UXCSHRKLBMRBOZ-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-ethyl-1-benzothiophen-5-yl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)SC2=CC=C(NS(C)(=O)=O)C=C12 UXCSHRKLBMRBOZ-UHFFFAOYSA-N 0.000 description 1
- KGDGLMYQULAQRS-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-ethyl-1-methylindol-4-yl]methanesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)N(C)C2=CC=CC(NS(C)(=O)=O)=C12 KGDGLMYQULAQRS-UHFFFAOYSA-N 0.000 description 1
- YTRJQAHVTLYTTE-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-methyl-1-benzofuran-5-yl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(C)OC2=CC=C(NS(C)(=O)=O)C=C12 YTRJQAHVTLYTTE-UHFFFAOYSA-N 0.000 description 1
- JNULNECEKFTCPD-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-phenylindolizin-7-yl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC(NS(C)(=O)=O)=C2 JNULNECEKFTCPD-UHFFFAOYSA-N 0.000 description 1
- KXDSNSVKKMXGPW-UHFFFAOYSA-N n-[3-[4-[3-(dibutylamino)propoxy]benzoyl]-2-propyl-1-benzofuran-5-yl]methanesulfonamide Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCC)OC2=CC=C(NS(C)(=O)=O)C=C12 KXDSNSVKKMXGPW-UHFFFAOYSA-N 0.000 description 1
- RTDQBEVJAPBBFR-UHFFFAOYSA-N n-[3-butyl-2-[4-[3-(dibutylamino)propoxy]benzoyl]-1-benzothiophen-5-yl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)C2=CC(NS(C)(=O)=O)=CC=C2S1 RTDQBEVJAPBBFR-UHFFFAOYSA-N 0.000 description 1
- GZDPUGUZQIECQW-UHFFFAOYSA-N n-[4-(2-butyl-5-nitro-1-benzofuran-3-carbonyl)phenyl]-3-(dibutylamino)propanamide Chemical compound C1=CC(NC(=O)CCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C([N+]([O-])=O)C=C12 GZDPUGUZQIECQW-UHFFFAOYSA-N 0.000 description 1
- ZICIDBKYNUPDGJ-UHFFFAOYSA-N n-[4-(2-butyl-5-nitro-1-benzofuran-3-carbonyl)phenyl]-4-(dibutylamino)butanamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(NC(=O)CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C([N+]([O-])=O)C=C12 ZICIDBKYNUPDGJ-UHFFFAOYSA-N 0.000 description 1
- RBCQDSVOLZWPEH-UHFFFAOYSA-N n-[4-(2-butyl-5-nitro-1-benzofuran-3-carbonyl)phenyl]-4-chlorobutanamide Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=C(NC(=O)CCCCl)C=C1 RBCQDSVOLZWPEH-UHFFFAOYSA-N 0.000 description 1
- ABWHZAKMWHHFGF-UHFFFAOYSA-N n-[4-[2-butyl-5-(methanesulfonamido)-1-benzofuran-3-carbonyl]phenyl]-3-(dibutylamino)propanamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(NC(=O)CCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 ABWHZAKMWHHFGF-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- WCGIGOVLOFXAMG-UHFFFAOYSA-N silver;trifluoromethanesulfonic acid Chemical compound [Ag].OS(=O)(=O)C(F)(F)F WCGIGOVLOFXAMG-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000011426 transformation method Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General 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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9010036 | 1990-08-06 | ||
| FR9010036A FR2665444B1 (fr) | 1990-08-06 | 1990-08-06 | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR920004371A KR920004371A (ko) | 1992-03-27 |
| KR100190673B1 true KR100190673B1 (ko) | 1999-06-01 |
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ID=9399463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910013726A Expired - Lifetime KR100190673B1 (ko) | 1990-08-06 | 1991-08-06 | 벤조푸란, 벤조 티오펜, 인돌 및 인돌리진의 유도체, 그것들의 제조방법 및 그것들을 함유한 조성물 |
Country Status (32)
Families Citing this family (183)
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| ES2114566T3 (es) * | 1991-08-09 | 1998-06-01 | Nycomed Innovation Ab | Uso de radicales libres persistentes en formacion de imagenes por resonancia magnetica nuclear. |
| US6756388B1 (en) * | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| DE4420925A1 (de) * | 1994-06-16 | 1995-12-21 | Bayer Ag | Verfahren zur Herstellung von Benzthiophenderivaten |
| US5596106A (en) * | 1994-07-15 | 1997-01-21 | Eli Lilly And Company | Cannabinoid receptor antagonists |
| GB9416219D0 (en) * | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
| US5510357A (en) * | 1995-02-28 | 1996-04-23 | Eli Lilly And Company | Benzothiophene compounds as anti-estrogenic agents |
| US5856339A (en) * | 1995-02-28 | 1999-01-05 | Eli Lilly And Company | Benzothiophene compounds, intermediates, compositions, and methods |
| US5998441A (en) * | 1995-02-28 | 1999-12-07 | Eli Lilly And Company | Benzothiophene compounds, intermediates, compositions, and methods |
| US5977093A (en) * | 1995-02-28 | 1999-11-02 | Eli Lilly And Company | Benzothiophene compounds, intermediates, compositions, and methods |
| US5856340A (en) * | 1995-02-28 | 1999-01-05 | Eli Lilly And Company | Method of treating estrogen dependent cancers |
| US5998401A (en) | 1995-02-28 | 1999-12-07 | Eli Lilly And Company | Naphthyl compounds, intermediates, compositions, and methods |
| US5919800A (en) * | 1995-02-28 | 1999-07-06 | Eli Lilly And Company | Benzothiophene compounds, intermediates, compositions, and methods |
| US6391892B1 (en) * | 1995-03-10 | 2002-05-21 | Eli Lilly And Company | Naphthyl pharmaceutical compounds |
| US6395755B1 (en) * | 1995-03-10 | 2002-05-28 | Eli Lilly And Company | Benzothiophene pharmaceutical compounds |
| US6417199B1 (en) * | 1995-03-10 | 2002-07-09 | Eli Lilly And Company | 3-benzyl-benzothiophenes |
| WO1996028156A1 (en) * | 1995-03-13 | 1996-09-19 | Eli Lilly And Company | Novel benzothiophene compounds and methods |
| FR2735365B1 (fr) * | 1995-06-14 | 1997-09-05 | Sanofi Sa | Utilisation d'un antagoniste de l'angiotensine ii et d'un derive du benzofurane pour la preparation d'un medicament utile dans le traitement des affections cardiovasculaires |
| US6432982B1 (en) * | 1996-02-21 | 2002-08-13 | Eli Lilly And Company | Benzothiophenes, and formulations and methods using same |
| FR2746013B1 (fr) * | 1996-03-18 | 1998-05-29 | Sanofi Sa | Utilisation de composes antiarythmiques dans la prevention de la mortalite post infarctus |
| AU5258696A (en) * | 1996-03-19 | 1997-10-10 | Eli Lilly And Company | Synthesis of 3-{4-(2-aminoethoxy)-benzoyl}-2-aryl-6-hydroxy-benzo{b}thiop henes |
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| TR201501970A2 (en) | 2015-02-19 | 2016-09-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Pharmaceutical combinations of dronedarone. |
| TR201502223A2 (tr) | 2015-02-25 | 2016-09-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dronedaron ve dabigatranın farmasötik kombinasyonları. |
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