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 (xx) |
| AT (1) | AT360003B (xx) |
| AU (1) | AU508330B2 (xx) |
| BE (1) | BE852778A (xx) |
| CA (1) | CA1104144A (xx) |
| CH (1) | CH628045A5 (xx) |
| DE (1) | DE2712045A1 (xx) |
| DK (1) | DK129277A (xx) |
| ES (1) | ES457132A1 (xx) |
| FI (1) | FI770930A (xx) |
| FR (1) | FR2345443A1 (xx) |
| GB (1) | GB1572358A (xx) |
| GR (1) | GR62464B (xx) |
| IE (1) | IE44727B1 (xx) |
| IL (1) | IL51718A (xx) |
| LU (1) | LU76997A1 (xx) |
| MC (1) | MC1133A1 (xx) |
| NL (1) | NL7703143A (xx) |
| NO (1) | NO771032L (xx) |
| NZ (1) | NZ183656A (xx) |
| PH (1) | PH13274A (xx) |
| PT (1) | PT66343B (xx) |
| SE (1) | SE436496B (xx) |
| ZA (1) | ZA771722B (xx) |
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 |
| WO2005105772A1 (de) * | 2004-04-14 | 2005-11-10 | Merck Patent Gmbh | Dibenzofuran-, dibenzothiophen- und fluorenderivate |
| KR102448440B1 (ko) * | 2016-09-27 | 2022-09-27 | 호도가야 가가쿠 고교 가부시키가이샤 | 증감 색소, 광전 변환용 증감 색소 및 그것을 사용한 광전 변환 소자 그리고 색소 증감 태양 전지 |
-
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 LU LU76997A patent/LU76997A1/xx unknown
- 1977-03-22 NZ NZ183656A patent/NZ183656A/xx unknown
- 1977-03-22 MC MC771236A patent/MC1133A1/xx unknown
- 1977-03-22 ZA ZA00771722A patent/ZA771722B/xx unknown
- 1977-03-23 GR GR53069A patent/GR62464B/el unknown
- 1977-03-23 BE BE176030A patent/BE852778A/xx not_active IP Right Cessation
- 1977-03-23 NO NO771032A patent/NO771032L/no unknown
- 1977-03-23 CA CA274,592A patent/CA1104144A/en not_active Expired
- 1977-03-23 NL NL7703143A patent/NL7703143A/xx not_active Application Discontinuation
- 1977-03-23 AT AT203577A patent/AT360003B/de not_active IP Right Cessation
- 1977-03-23 ES ES457132A patent/ES457132A1/es not_active Expired
- 1977-03-23 JP JP3121977A patent/JPS52116461A/ja active Pending
- 1977-03-23 SE SE7703353A patent/SE436496B/xx unknown
- 1977-03-23 PH PH19581A patent/PH13274A/en unknown
- 1977-03-23 GB GB12224/77A patent/GB1572358A/en not_active Expired
- 1977-03-23 PT PT66343A patent/PT66343B/pt unknown
- 1977-03-23 DK DK129277A patent/DK129277A/da not_active Application Discontinuation
- 1977-03-23 IE IE615/77A patent/IE44727B1/en unknown
- 1977-03-24 AU AU23572/77A patent/AU508330B2/en not_active Expired
- 1977-03-24 FI FI770930A patent/FI770930A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE436496B (sv) | 1984-12-17 |
| FR2345443B1 (xx) | 1979-03-09 |
| IL51718A (en) | 1980-11-30 |
| IE44727L (en) | 1977-09-24 |
| PT66343B (en) | 1979-01-18 |
| SE7703353L (sv) | 1977-10-07 |
| AT360003B (de) | 1980-12-10 |
| MC1133A1 (fr) | 1977-11-18 |
| PH13274A (en) | 1980-02-27 |
| DE2712045A1 (de) | 1977-09-29 |
| NL7703143A (nl) | 1977-09-27 |
| IL51718A0 (en) | 1977-05-31 |
| CA1104144A (en) | 1981-06-30 |
| FR2345443A1 (fr) | 1977-10-21 |
| JPS52116461A (en) | 1977-09-29 |
| GR62464B (en) | 1979-04-13 |
| AU2357277A (en) | 1978-09-28 |
| FI770930A (xx) | 1977-09-25 |
| LU76997A1 (xx) | 1978-06-01 |
| ES457132A1 (es) | 1978-08-16 |
| ZA771722B (en) | 1978-02-22 |
| CH628045A5 (en) | 1982-02-15 |
| ATA203577A (de) | 1980-05-15 |
| AU508330B2 (en) | 1980-03-20 |
| GB1572358A (en) | 1980-07-30 |
| BE852778A (fr) | 1977-09-23 |
| IE44727B1 (en) | 1982-03-10 |
| PT66343A (en) | 1977-04-01 |
| NZ183656A (en) | 1979-01-11 |
| DK129277A (da) | 1977-09-25 |
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