NO771032L - Dibenzotiofen-derivater. - Google Patents
Dibenzotiofen-derivater.Info
- Publication number
- NO771032L NO771032L NO771032A NO771032A NO771032L NO 771032 L NO771032 L NO 771032L NO 771032 A NO771032 A NO 771032A NO 771032 A NO771032 A NO 771032A NO 771032 L NO771032 L NO 771032L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- lower alkoxy
- alkylamino
- amino
- hydroxy
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 118
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000003545 alkoxy group Chemical group 0.000 claims description 76
- -1 nitro, amino Chemical group 0.000 claims description 55
- 238000002360 preparation method Methods 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- DJOWHYLXBIPXAK-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)acetic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 DJOWHYLXBIPXAK-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- FMEKJVJLZKALPJ-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)ethanol Chemical compound C1=C(Cl)C=C2C3=CC=C(CCO)C=C3SC2=C1 FMEKJVJLZKALPJ-UHFFFAOYSA-N 0.000 claims description 5
- LYUKZRJWZUTRJV-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)propanoic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3SC2=C1 LYUKZRJWZUTRJV-UHFFFAOYSA-N 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 5
- VALLCBPLPVWPLP-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)acetamide Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)N)C=C3SC2=C1 VALLCBPLPVWPLP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 230000003356 anti-rheumatic effect Effects 0.000 claims description 4
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 4
- HJGQRFOXAYHUHQ-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)propan-1-ol Chemical compound C1=C(Cl)C=C2C3=CC=C(C(CO)C)C=C3SC2=C1 HJGQRFOXAYHUHQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 154
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 63
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 238000010992 reflux Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 239000012259 ether extract Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- ZIYOAMMZCMIUDK-UHFFFAOYSA-N ethyl 2-(3-bromo-4-oxocyclohexyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)C(Br)C1 ZIYOAMMZCMIUDK-UHFFFAOYSA-N 0.000 description 7
- JHHTWYQHGGLWRX-UHFFFAOYSA-N ethyl 2-(8-chlorodibenzothiophen-3-yl)acetate Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 JHHTWYQHGGLWRX-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 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 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- FAMKYYGHYXYRPU-UHFFFAOYSA-N ethyl 2-(7-chlorodibenzothiophen-3-yl)acetate Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 FAMKYYGHYXYRPU-UHFFFAOYSA-N 0.000 description 4
- IGOWSOGBQMBHIY-UHFFFAOYSA-N ethyl 3-bromo-4-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCC(=O)C(Br)C1 IGOWSOGBQMBHIY-UHFFFAOYSA-N 0.000 description 4
- VFMOMKJKSKUWGU-UHFFFAOYSA-N ethyl 7-aminodibenzothiophene-3-carboxylate;hydrochloride Chemical compound Cl.NC1=CC=C2C3=CC=C(C(=O)OCC)C=C3SC2=C1 VFMOMKJKSKUWGU-UHFFFAOYSA-N 0.000 description 4
- ULEDJSBHBHXSBA-UHFFFAOYSA-N ethyl 7-nitro-5-oxodibenzothiophene-3-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2S(=O)C3=CC(C(=O)OCC)=CC=C3C2=C1 ULEDJSBHBHXSBA-UHFFFAOYSA-N 0.000 description 4
- FKVNRQGGNSXIDN-UHFFFAOYSA-N ethyl dibenzothiophene-3-carboxylate Chemical compound C1=CC=C2C3=CC=C(C(=O)OCC)C=C3SC2=C1 FKVNRQGGNSXIDN-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UQODKSRRNBKAGH-UHFFFAOYSA-N 2-(8-methyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(C)=CC=C3SC2=C1 UQODKSRRNBKAGH-UHFFFAOYSA-N 0.000 description 3
- UPJJOXZYFPZPCP-UHFFFAOYSA-N 2-(9-chlorodibenzothiophen-3-yl)acetic acid Chemical compound C1=CC(Cl)=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 UPJJOXZYFPZPCP-UHFFFAOYSA-N 0.000 description 3
- RJYRJPVTQFXMFV-UHFFFAOYSA-N 2-diazonio-1-(8-methyldibenzothiophen-3-yl)ethenolate Chemical compound [N-]=[N+]=CC(=O)C1=CC=C2C3=CC(C)=CC=C3SC2=C1 RJYRJPVTQFXMFV-UHFFFAOYSA-N 0.000 description 3
- OPRCCOHUHQXRAA-UHFFFAOYSA-N 2-dibenzothiophen-3-ylacetic acid Chemical compound C1=CC=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 OPRCCOHUHQXRAA-UHFFFAOYSA-N 0.000 description 3
- HKNIVZRGKVNBNF-UHFFFAOYSA-N 7-(dimethylamino)dibenzothiophene-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2C3=CC=C(N(C)C)C=C3SC2=C1 HKNIVZRGKVNBNF-UHFFFAOYSA-N 0.000 description 3
- RVZYJGNJFOHNHW-UHFFFAOYSA-N 7-chlorodibenzothiophene-3-carbonyl chloride Chemical compound ClC1=CC=C2C3=CC=C(C(=O)Cl)C=C3SC2=C1 RVZYJGNJFOHNHW-UHFFFAOYSA-N 0.000 description 3
- XHDTZUKTOGKDRA-UHFFFAOYSA-N 8-methyldibenzothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC(C)=CC=C3SC2=C1 XHDTZUKTOGKDRA-UHFFFAOYSA-N 0.000 description 3
- JHRDKDPBNWCBFI-UHFFFAOYSA-N C1=CC(CCCC)=CC=C1SC1C(=O)CCC(CC(=O)OCC)C1 Chemical compound C1=CC(CCCC)=CC=C1SC1C(=O)CCC(CC(=O)OCC)C1 JHRDKDPBNWCBFI-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- SRGIZIYHJGNDMB-UHFFFAOYSA-N ethyl 2-(6-chlorodibenzothiophen-3-yl)acetate Chemical compound C1=CC=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1Cl SRGIZIYHJGNDMB-UHFFFAOYSA-N 0.000 description 3
- SJZCYGZAJGYIIN-UHFFFAOYSA-N ethyl 2-(8-chloro-1,2,3,4-tetrahydrodibenzothiophen-3-yl)acetate Chemical compound S1C2=CC=C(Cl)C=C2C2=C1CC(CC(=O)OCC)CC2 SJZCYGZAJGYIIN-UHFFFAOYSA-N 0.000 description 3
- OXRGWKLEJCKNHN-UHFFFAOYSA-N ethyl 2-(8-methyldibenzothiophen-3-yl)acetate Chemical compound C1=C(C)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 OXRGWKLEJCKNHN-UHFFFAOYSA-N 0.000 description 3
- RKDPOMRZAUQPSH-UHFFFAOYSA-N ethyl 2-(9-chloro-1,2,3,4-tetrahydrodibenzothiophen-3-yl)acetate Chemical compound S1C2=CC=CC(Cl)=C2C2=C1CC(CC(=O)OCC)CC2 RKDPOMRZAUQPSH-UHFFFAOYSA-N 0.000 description 3
- MOBYURAWDLMHIU-UHFFFAOYSA-N ethyl 2-(9-chlorodibenzothiophen-3-yl)acetate Chemical compound C1=CC(Cl)=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 MOBYURAWDLMHIU-UHFFFAOYSA-N 0.000 description 3
- HKYOCZIMWLNDCN-UHFFFAOYSA-N ethyl 2-dibenzothiophen-3-ylacetate Chemical compound C1=CC=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 HKYOCZIMWLNDCN-UHFFFAOYSA-N 0.000 description 3
- AREKCHFYRDYSSC-UHFFFAOYSA-N ethyl 3-(4-methylphenyl)sulfanyl-4-oxocyclohexane-1-carboxylate Chemical compound C1C(C(=O)OCC)CCC(=O)C1SC1=CC=C(C)C=C1 AREKCHFYRDYSSC-UHFFFAOYSA-N 0.000 description 3
- LFOXDBYWLIAZEC-UHFFFAOYSA-N ethyl 5-oxodibenzothiophene-3-carboxylate Chemical compound C1=CC=C2S(=O)C3=CC(C(=O)OCC)=CC=C3C2=C1 LFOXDBYWLIAZEC-UHFFFAOYSA-N 0.000 description 3
- RWFRBVFLMOUDAI-UHFFFAOYSA-N ethyl 7-(dimethylamino)dibenzothiophene-3-carboxylate Chemical compound CN(C)C1=CC=C2C3=CC=C(C(=O)OCC)C=C3SC2=C1 RWFRBVFLMOUDAI-UHFFFAOYSA-N 0.000 description 3
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- 201000011510 cancer Diseases 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- FFJWAUPFPXZMDP-UHFFFAOYSA-N dibenzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C=C3SC2=C1 FFJWAUPFPXZMDP-UHFFFAOYSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- YFMGHVQBAINRBB-UHFFFAOYSA-L disodium hydrogen carbonate chloride hydrate Chemical compound C([O-])(O)=O.[Na+].Cl.[OH-].[Na+] YFMGHVQBAINRBB-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- ZXUNBMDEZYTURL-UHFFFAOYSA-N ethyl 1,2,3,4-tetrahydrodibenzothiophene-3-carboxylate Chemical compound S1C2=CC=CC=C2C2=C1CC(C(=O)OCC)CC2 ZXUNBMDEZYTURL-UHFFFAOYSA-N 0.000 description 1
- XHNJFNLTFMAPQB-UHFFFAOYSA-N ethyl 2-(4-oxocyclohexyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)CC1 XHNJFNLTFMAPQB-UHFFFAOYSA-N 0.000 description 1
- JHYHLOZMRWPRTD-UHFFFAOYSA-N ethyl 2-(8-acetamidodibenzothiophen-3-yl)acetate Chemical compound C1=C(NC(C)=O)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 JHYHLOZMRWPRTD-UHFFFAOYSA-N 0.000 description 1
- HTWCOMSCNSWTJJ-UHFFFAOYSA-N ethyl 2-(8-butyl-1,2,3,4-tetrahydrodibenzothiophen-3-yl)acetate Chemical compound C1C(CC(=O)OCC)CCC2=C1SC1=CC=C(CCCC)C=C12 HTWCOMSCNSWTJJ-UHFFFAOYSA-N 0.000 description 1
- NLRCOOXFQNANLX-UHFFFAOYSA-N ethyl 2-(8-chlorodibenzothiophen-3-yl)hexanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(=O)OCC)CCCC)C=C3SC2=C1 NLRCOOXFQNANLX-UHFFFAOYSA-N 0.000 description 1
- WSXWYZFWKHSGHJ-UHFFFAOYSA-N ethyl 2-(8-chlorodibenzothiophen-3-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)C(=O)OCC)C=C3SC2=C1 WSXWYZFWKHSGHJ-UHFFFAOYSA-N 0.000 description 1
- JZAYBZIZSJEJGP-UHFFFAOYSA-N ethyl 2-(8-fluorodibenzothiophen-3-yl)acetate Chemical compound C1=C(F)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 JZAYBZIZSJEJGP-UHFFFAOYSA-N 0.000 description 1
- IIMHDGLQSLVKCC-UHFFFAOYSA-N ethyl 2-(8-methylsulfanyldibenzothiophen-3-yl)acetate Chemical compound C1=C(SC)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 IIMHDGLQSLVKCC-UHFFFAOYSA-N 0.000 description 1
- RFYBOCRTKBZTMY-UHFFFAOYSA-N ethyl 2-(8-nitrodibenzothiophen-3-yl)acetate Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 RFYBOCRTKBZTMY-UHFFFAOYSA-N 0.000 description 1
- APXGHFQNRZNCOL-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenyl)sulfanyl-4-oxocyclohexyl]acetate Chemical compound C1C(CC(=O)OCC)CCC(=O)C1SC1=CC=CC=C1Cl APXGHFQNRZNCOL-UHFFFAOYSA-N 0.000 description 1
- RTXAOBNAIAGNOZ-UHFFFAOYSA-N ethyl 2-[8-(trifluoromethyl)dibenzothiophen-3-yl]acetate Chemical compound C1=C(C(F)(F)F)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 RTXAOBNAIAGNOZ-UHFFFAOYSA-N 0.000 description 1
- ZBDAMDWKXGTKBT-UHFFFAOYSA-N ethyl 2-cyclohexylacetate Chemical compound CCOC(=O)CC1CCCCC1 ZBDAMDWKXGTKBT-UHFFFAOYSA-N 0.000 description 1
- FZBNQIWPYCUPAP-UHFFFAOYSA-N ethyl 2-thiophen-3-ylacetate Chemical compound CCOC(=O)CC=1C=CSC=1 FZBNQIWPYCUPAP-UHFFFAOYSA-N 0.000 description 1
- UQNSTAZZAWUVLI-UHFFFAOYSA-N ethyl 3-(8-chlorodibenzothiophen-3-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(CCC(=O)OCC)C=C3SC2=C1 UQNSTAZZAWUVLI-UHFFFAOYSA-N 0.000 description 1
- IHWZEZJLIDKXEJ-UHFFFAOYSA-N ethyl 7-aminodibenzothiophene-3-carboxylate Chemical compound NC1=CC=C2C3=CC=C(C(=O)OCC)C=C3SC2=C1 IHWZEZJLIDKXEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ZBUQPAJRQXISTC-UHFFFAOYSA-N n-(chloromethyl)-n-ethylethanamine Chemical compound CCN(CC)CCl ZBUQPAJRQXISTC-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-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
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- RVXNIFYJPYSWSC-UHFFFAOYSA-M potassium;7-chlorodibenzothiophene-3-carboxylate Chemical compound [K+].ClC1=CC=C2C3=CC=C(C(=O)[O-])C=C3SC2=C1 RVXNIFYJPYSWSC-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 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
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D333/76—Dibenzothiophenes
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)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66994076A | 1976-03-24 | 1976-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771032L true NO771032L (no) | 1977-09-27 |
Family
ID=24688362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771032A NO771032L (no) | 1976-03-24 | 1977-03-23 | Dibenzotiofen-derivater. |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS52116461A (de) |
| AT (1) | AT360003B (de) |
| AU (1) | AU508330B2 (de) |
| BE (1) | BE852778A (de) |
| CA (1) | CA1104144A (de) |
| CH (1) | CH628045A5 (de) |
| DE (1) | DE2712045A1 (de) |
| DK (1) | DK129277A (de) |
| ES (1) | ES457132A1 (de) |
| FI (1) | FI770930A (de) |
| FR (1) | FR2345443A1 (de) |
| GB (1) | GB1572358A (de) |
| GR (1) | GR62464B (de) |
| IE (1) | IE44727B1 (de) |
| IL (1) | IL51718A (de) |
| LU (1) | LU76997A1 (de) |
| MC (1) | MC1133A1 (de) |
| NL (1) | NL7703143A (de) |
| NO (1) | NO771032L (de) |
| NZ (1) | NZ183656A (de) |
| PH (1) | PH13274A (de) |
| PT (1) | PT66343B (de) |
| SE (1) | SE436496B (de) |
| ZA (1) | ZA771722B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8428930D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
| GB2380192B8 (en) * | 2001-02-09 | 2005-09-14 | Sumitomo Chemical Co | Phenylacetylene compounds liquid crystal compositions polymers optically anisotropic products & optical & liquid crystal elements derived therefrom |
| EP1742931B1 (de) * | 2004-04-14 | 2014-04-23 | Merck Patent GmbH | Dibenzofuran-, dibenzothiophen- und fluorenderivate als komponenten in flüssigkristallmischungen |
| WO2018061409A1 (ja) * | 2016-09-27 | 2018-04-05 | 保土谷化学工業株式会社 | 増感色素、光電変換用増感色素およびそれを用いた光電変換素子ならびに色素増感太陽電池 |
-
1977
- 1977-03-11 CH CH310177A patent/CH628045A5/de not_active IP Right Cessation
- 1977-03-18 DE DE19772712045 patent/DE2712045A1/de not_active Ceased
- 1977-03-22 FR FR7708489A patent/FR2345443A1/fr active Granted
- 1977-03-22 IL IL51718A patent/IL51718A/xx unknown
- 1977-03-22 MC MC771236A patent/MC1133A1/xx unknown
- 1977-03-22 ZA ZA00771722A patent/ZA771722B/xx unknown
- 1977-03-22 NZ NZ183656A patent/NZ183656A/xx unknown
- 1977-03-22 LU LU76997A patent/LU76997A1/xx unknown
- 1977-03-23 AT AT203577A patent/AT360003B/de not_active IP Right Cessation
- 1977-03-23 GR GR53069A patent/GR62464B/el unknown
- 1977-03-23 NO NO771032A patent/NO771032L/no unknown
- 1977-03-23 CA CA274,592A patent/CA1104144A/en not_active Expired
- 1977-03-23 ES ES457132A patent/ES457132A1/es not_active Expired
- 1977-03-23 PT PT66343A patent/PT66343B/pt unknown
- 1977-03-23 PH PH19581A patent/PH13274A/en unknown
- 1977-03-23 BE BE176030A patent/BE852778A/xx not_active IP Right Cessation
- 1977-03-23 SE SE7703353A patent/SE436496B/xx unknown
- 1977-03-23 GB GB12224/77A patent/GB1572358A/en not_active Expired
- 1977-03-23 DK DK129277A patent/DK129277A/da not_active Application Discontinuation
- 1977-03-23 NL NL7703143A patent/NL7703143A/xx not_active Application Discontinuation
- 1977-03-23 IE IE615/77A patent/IE44727B1/en unknown
- 1977-03-23 JP JP3121977A patent/JPS52116461A/ja active Pending
- 1977-03-24 FI FI770930A patent/FI770930A/fi not_active Application Discontinuation
- 1977-03-24 AU AU23572/77A patent/AU508330B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA203577A (de) | 1980-05-15 |
| AU508330B2 (en) | 1980-03-20 |
| NZ183656A (en) | 1979-01-11 |
| DE2712045A1 (de) | 1977-09-29 |
| DK129277A (da) | 1977-09-25 |
| CH628045A5 (en) | 1982-02-15 |
| ES457132A1 (es) | 1978-08-16 |
| NL7703143A (nl) | 1977-09-27 |
| AU2357277A (en) | 1978-09-28 |
| IE44727L (en) | 1977-09-24 |
| FI770930A (de) | 1977-09-25 |
| MC1133A1 (fr) | 1977-11-18 |
| PT66343A (en) | 1977-04-01 |
| AT360003B (de) | 1980-12-10 |
| IL51718A0 (en) | 1977-05-31 |
| CA1104144A (en) | 1981-06-30 |
| IL51718A (en) | 1980-11-30 |
| JPS52116461A (en) | 1977-09-29 |
| ZA771722B (en) | 1978-02-22 |
| PH13274A (en) | 1980-02-27 |
| PT66343B (en) | 1979-01-18 |
| GB1572358A (en) | 1980-07-30 |
| BE852778A (fr) | 1977-09-23 |
| SE7703353L (sv) | 1977-11-07 |
| FR2345443B1 (de) | 1979-03-09 |
| SE436496B (sv) | 1984-12-17 |
| LU76997A1 (de) | 1978-06-01 |
| GR62464B (en) | 1979-04-13 |
| IE44727B1 (en) | 1982-03-10 |
| FR2345443A1 (fr) | 1977-10-21 |
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