CH628045A5 - Process for the preparation of dibenzothiophene derivatives - Google Patents

Process for the preparation of dibenzothiophene derivatives Download PDF

Info

Publication number: CH628045A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; lower alkoxy; hydroxy; acetic acid
Prior art date: 1976-03-24

Application number

CH310177A

Other languages

German (de)

English (en)

Inventor

Leo Berger

John Thomas Plati

Albert Ziering

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-03-24

Filing date

1977-03-11

Publication date

1982-02-15

1977-03-11 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1982-02-15 Publication of CH628045A5 publication Critical patent/CH628045A5/de

Links

238000000034 method Methods 0.000 title claims description 51
238000002360 preparation method Methods 0.000 title claims description 18
230000008569 process Effects 0.000 title claims description 15
IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 65
125000003545 alkoxy group Chemical group 0.000 claims description 44
-1 nitro, amino Chemical group 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
150000001350 alkyl halides Chemical class 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
239000000243 solution Substances 0.000 description 80
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
238000010992 reflux Methods 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
230000008018 melting Effects 0.000 description 27
238000002844 melting Methods 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
150000002148 esters Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012259 ether extract Substances 0.000 description 9
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000009835 boiling Methods 0.000 description 7
230000004044 response Effects 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
206010030113 Oedema Diseases 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000012360 testing method Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
239000002585 base Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001704 evaporation Methods 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
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
229920000137 polyphosphoric acid Polymers 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
238000003756 stirring Methods 0.000 description 4
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 4
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 description 3
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 description 3
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 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
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 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
210000002683 foot Anatomy 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
ZIXXRXGPBFMPFD-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)disulfanyl]benzene Chemical compound C1=CC(Cl)=CC=C1SSC1=CC=C(Cl)C=C1 ZIXXRXGPBFMPFD-UHFFFAOYSA-N 0.000 description 2
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 2
IAAVPSNSNJYAAU-UHFFFAOYSA-N 2-(2-chlorophenyl)sulfanylcyclohexan-1-one;ethyl acetate Chemical compound CCOC(C)=O.ClC1=CC=CC=C1SC1C(=O)CCCC1 IAAVPSNSNJYAAU-UHFFFAOYSA-N 0.000 description 2
DFCDSCDYDNIBRN-UHFFFAOYSA-N 2-(6-chlorodibenzothiophen-3-yl)acetic acid Chemical compound C1=CC=C2C3=CC=C(CC(=O)O)C=C3SC2=C1Cl DFCDSCDYDNIBRN-UHFFFAOYSA-N 0.000 description 2
YSHTUOOXOIFOJG-UHFFFAOYSA-N 2-(7-chlorodibenzothiophen-3-yl)acetic acid Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 YSHTUOOXOIFOJG-UHFFFAOYSA-N 0.000 description 2
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 description 2
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 2
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 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
230000001760 anti-analgesic effect Effects 0.000 description 2
239000003435 antirheumatic agent Substances 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
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 2
KWRIYWKCYJWBQA-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)sulfanyl-4-oxocyclohexyl]acetate Chemical compound C1C(CC(=O)OCC)CCC(=O)C1SC1=CC=C(Cl)C=C1 KWRIYWKCYJWBQA-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
RIQNHDQHFNFGSA-UHFFFAOYSA-N 2-(6,7-dichlorodibenzothiophen-3-yl)acetic acid Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)O)C=C3SC2=C1Cl RIQNHDQHFNFGSA-UHFFFAOYSA-N 0.000 description 1
WDKLEDBKKUNMGF-UHFFFAOYSA-N 2-(7,8-dichlorodibenzothiophen-3-yl)acetic acid Chemical compound ClC1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 WDKLEDBKKUNMGF-UHFFFAOYSA-N 0.000 description 1
KREBBTBGIJROSS-UHFFFAOYSA-N 2-(7-methoxydibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC=C(OC)C=C3SC2=C1 KREBBTBGIJROSS-UHFFFAOYSA-N 0.000 description 1
HPVYDRLPRBMLLY-UHFFFAOYSA-N 2-(7-methyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC=C(C)C=C3SC2=C1 HPVYDRLPRBMLLY-UHFFFAOYSA-N 0.000 description 1
HORHNSYXEBXTSG-UHFFFAOYSA-N 2-(8,9-dichlorodibenzothiophen-3-yl)acetic acid Chemical compound C1=C(Cl)C(Cl)=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 HORHNSYXEBXTSG-UHFFFAOYSA-N 0.000 description 1
QSTHXMDBFAQADW-UHFFFAOYSA-N 2-(8-acetyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(C(=O)C)=CC=C3SC2=C1 QSTHXMDBFAQADW-UHFFFAOYSA-N 0.000 description 1
LXIXATBFJHHJQH-UHFFFAOYSA-N 2-(8-benzoyldibenzothiophen-3-yl)acetic acid Chemical compound C=1C(CC(=O)O)=CC=C(C2=C3)C=1SC2=CC=C3C(=O)C1=CC=CC=C1 LXIXATBFJHHJQH-UHFFFAOYSA-N 0.000 description 1
XEFFMHPXBKVNIK-UHFFFAOYSA-N 2-(8-butyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(CCCC)=CC=C3SC2=C1 XEFFMHPXBKVNIK-UHFFFAOYSA-N 0.000 description 1
PKLFZFYECMGXFM-UHFFFAOYSA-N 2-(8-chloro-7-methyldibenzothiophen-3-yl)acetic acid Chemical compound S1C2=CC(CC(O)=O)=CC=C2C2=C1C=C(C)C(Cl)=C2 PKLFZFYECMGXFM-UHFFFAOYSA-N 0.000 description 1
WURMZSLHPNWJNM-UHFFFAOYSA-N 2-(8-chloro-9-methyldibenzothiophen-3-yl)acetic acid Chemical compound S1C2=CC(CC(O)=O)=CC=C2C2=C1C=CC(Cl)=C2C WURMZSLHPNWJNM-UHFFFAOYSA-N 0.000 description 1
MUGMFWLHGURFJE-UHFFFAOYSA-N 2-(8-chlorodibenzothiophen-3-yl)-n,n-dimethylacetamide Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)N(C)C)C=C3SC2=C1 MUGMFWLHGURFJE-UHFFFAOYSA-N 0.000 description 1
YZRPCHNMFWMLFD-UHFFFAOYSA-N 2-(8-cyanodibenzothiophen-3-yl)acetic acid Chemical compound C1=C(C#N)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 YZRPCHNMFWMLFD-UHFFFAOYSA-N 0.000 description 1
SHJVGBHYXMVHBV-UHFFFAOYSA-N 2-(8-ethyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(CC)=CC=C3SC2=C1 SHJVGBHYXMVHBV-UHFFFAOYSA-N 0.000 description 1
YGXOGUQDHJVKDS-UHFFFAOYSA-N 2-(8-fluorodibenzothiophen-3-yl)acetic acid Chemical compound C1=C(F)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 YGXOGUQDHJVKDS-UHFFFAOYSA-N 0.000 description 1
UQENZWCTYKQQNU-UHFFFAOYSA-N 2-(8-hydroxydibenzothiophen-3-yl)acetic acid Chemical compound C1=C(O)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 UQENZWCTYKQQNU-UHFFFAOYSA-N 0.000 description 1
KRQZGZHKIMKKQH-UHFFFAOYSA-N 2-(8-iododibenzothiophen-3-yl)acetic acid Chemical compound C1=C(I)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 KRQZGZHKIMKKQH-UHFFFAOYSA-N 0.000 description 1
UAUIQCMZDUUUSK-UHFFFAOYSA-N 2-(8-methoxydibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(OC)=CC=C3SC2=C1 UAUIQCMZDUUUSK-UHFFFAOYSA-N 0.000 description 1
ZTIPHGJJFPJCNY-UHFFFAOYSA-N 2-(8-methylsulfanyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(SC)=CC=C3SC2=C1 ZTIPHGJJFPJCNY-UHFFFAOYSA-N 0.000 description 1
NPJYFNIUHMWSSQ-UHFFFAOYSA-N 2-(8-nitrodibenzothiophen-3-yl)acetic acid Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 NPJYFNIUHMWSSQ-UHFFFAOYSA-N 0.000 description 1
UJHOKDZBWFANLN-UHFFFAOYSA-N 2-(8-phenylmethoxydibenzothiophen-3-yl)acetic acid Chemical compound C=1C(CC(=O)O)=CC=C(C2=C3)C=1SC2=CC=C3OCC1=CC=CC=C1 UJHOKDZBWFANLN-UHFFFAOYSA-N 0.000 description 1
UIMJIEFGLACZJY-UHFFFAOYSA-N 2-(9-chloro-8-sulfamoyldibenzothiophen-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=C(Cl)C(S(=O)(=O)N)=CC=C3SC2=C1 UIMJIEFGLACZJY-UHFFFAOYSA-N 0.000 description 1
XCVBVHYNIQKUCE-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-(8-chlorodibenzothiophen-3-yl)acetate Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)OCCN(C)C)C=C3SC2=C1 XCVBVHYNIQKUCE-UHFFFAOYSA-N 0.000 description 1
BFFDWWGXTIETOO-UHFFFAOYSA-N 2-[8-(dimethylsulfamoyl)dibenzothiophen-3-yl]acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(S(=O)(=O)N(C)C)=CC=C3SC2=C1 BFFDWWGXTIETOO-UHFFFAOYSA-N 0.000 description 1
WVCDRFIKCHQVSF-UHFFFAOYSA-N 2-[8-(trifluoromethyl)dibenzothiophen-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C=C2C3=CC=C(CC(=O)O)C=C3SC2=C1 WVCDRFIKCHQVSF-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
CRZZYXUUPZTFGR-UHFFFAOYSA-N 2-bromo-n-methylethanamine Chemical compound CNCCBr CRZZYXUUPZTFGR-UHFFFAOYSA-N 0.000 description 1
PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
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 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical compound OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
VRGCYEIGVVTZCC-UHFFFAOYSA-N 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione Chemical compound ClC1=C(Cl)C(=O)C(=O)C(Cl)=C1Cl VRGCYEIGVVTZCC-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
CQJDYPZUDYXHLM-UHFFFAOYSA-N 3-chlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1 CQJDYPZUDYXHLM-UHFFFAOYSA-N 0.000 description 1
DKGGRHVKKQWAPT-UHFFFAOYSA-N 4-(2-methylpropyl)benzenethiol Chemical compound CC(C)CC1=CC=C(S)C=C1 DKGGRHVKKQWAPT-UHFFFAOYSA-N 0.000 description 1
VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
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 1
IHHJUGWRJIWCNI-UHFFFAOYSA-N CCC1=CC(CC(O)=O)=CC2=C1C(C(Cl)=CC=C1)=C1S2 Chemical compound CCC1=CC(CC(O)=O)=CC2=C1C(C(Cl)=CC=C1)=C1S2 IHHJUGWRJIWCNI-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
239000002841 Lewis acid Substances 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005011 alkyl ether group Chemical group 0.000 description 1
125000005012 alkyl thioether group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
CEALXSHFPPCRNM-UHFFFAOYSA-L disodium;carboxylato carbonate Chemical class [Na+].[Na+].[O-]C(=O)OC([O-])=O CEALXSHFPPCRNM-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 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
XZSWULLUAMXCEW-UHFFFAOYSA-N ethyl 2-(6,7-dichlorodibenzothiophen-3-yl)acetate Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1Cl XZSWULLUAMXCEW-UHFFFAOYSA-N 0.000 description 1
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 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
MBWDJPKKRDZNOQ-UHFFFAOYSA-N ethyl 2-(8-bromodibenzothiophen-3-yl)acetate Chemical compound C1=C(Br)C=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 MBWDJPKKRDZNOQ-UHFFFAOYSA-N 0.000 description 1
HUFYVOQIBXUNQX-UHFFFAOYSA-N ethyl 2-(8-butyldibenzothiophen-3-yl)acetate Chemical compound CCOC(=O)CC1=CC=C2C3=CC(CCCC)=CC=C3SC2=C1 HUFYVOQIBXUNQX-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
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 1
KNAIERZJSMJTLG-UHFFFAOYSA-N ethyl 2-[3-(3-chlorophenyl)sulfanyl-4-oxocyclohexyl]acetate Chemical compound C1C(CC(=O)OCC)CCC(=O)C1SC1=CC=CC(Cl)=C1 KNAIERZJSMJTLG-UHFFFAOYSA-N 0.000 description 1
XORNQTGMVXWYLD-UHFFFAOYSA-N ethyl 2-[7-(dimethylamino)dibenzothiophen-3-yl]acetate Chemical compound CN(C)C1=CC=C2C3=CC=C(CC(=O)OCC)C=C3SC2=C1 XORNQTGMVXWYLD-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
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
125000004494 ethyl ester group Chemical group 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
230000005496 eutectics Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 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
210000000548 hind-foot Anatomy 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
150000002823 nitrates Chemical class 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases 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
229910052763 palladium Inorganic materials 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
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent 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
238000001556 precipitation Methods 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer 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
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-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

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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)

CH310177A 1976-03-24 1977-03-11 Process for the preparation of dibenzothiophene derivatives CH628045A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US66994076A	1976-03-24	1976-03-24

Publications (1)

Publication Number	Publication Date
CH628045A5 true CH628045A5 (en)	1982-02-15

Family

ID=24688362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH310177A CH628045A5 (en)	1976-03-24	1977-03-11	Process for the preparation of dibenzothiophene derivatives

Country Status (24)

Country	Link
JP (1)	JPS52116461A (fr)
AT (1)	AT360003B (fr)
AU (1)	AU508330B2 (fr)
BE (1)	BE852778A (fr)
CA (1)	CA1104144A (fr)
CH (1)	CH628045A5 (fr)
DE (1)	DE2712045A1 (fr)
DK (1)	DK129277A (fr)
ES (1)	ES457132A1 (fr)
FI (1)	FI770930A7 (fr)
FR (1)	FR2345443A1 (fr)
GB (1)	GB1572358A (fr)
GR (1)	GR62464B (fr)
IE (1)	IE44727B1 (fr)
IL (1)	IL51718A (fr)
LU (1)	LU76997A1 (fr)
MC (1)	MC1133A1 (fr)
NL (1)	NL7703143A (fr)
NO (1)	NO771032L (fr)
NZ (1)	NZ183656A (fr)
PH (1)	PH13274A (fr)
PT (1)	PT66343B (fr)
SE (1)	SE436496B (fr)
ZA (1)	ZA771722B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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
CN1942461B (zh) *	2004-04-14	2011-11-09	默克专利股份有限公司	二苯并呋喃、二苯并噻吩和芴衍生物
WO2018061409A1 (fr) *	2016-09-27	2018-04-05	保土谷化学工業株式会社	Colorant sensibilisateur, colorant sensibilisateur pour conversion photoélectrique et transducteur photoélectrique l'utilisant, et cellule solaire à colorant sensibilisateur

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 MC MC771236A patent/MC1133A1/fr unknown
- 1977-03-22 ZA ZA00771722A patent/ZA771722B/xx unknown
- 1977-03-22 NZ NZ183656A patent/NZ183656A/xx unknown
- 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
- 1977-03-23 PT PT66343A patent/PT66343B/pt unknown
- 1977-03-23 DK DK129277A patent/DK129277A/da not_active Application Discontinuation
- 1977-03-23 CA CA274,592A patent/CA1104144A/fr not_active Expired
- 1977-03-23 ES ES457132A patent/ES457132A1/es not_active Expired
- 1977-03-23 PH PH19581A patent/PH13274A/en unknown
- 1977-03-23 BE BE176030A patent/BE852778A/fr not_active IP Right Cessation
- 1977-03-23 NL NL7703143A patent/NL7703143A/xx not_active Application Discontinuation
- 1977-03-23 GR GR53069A patent/GR62464B/el unknown
- 1977-03-23 JP JP3121977A patent/JPS52116461A/ja active Pending
- 1977-03-23 IE IE615/77A patent/IE44727B1/en unknown
- 1977-03-23 GB GB12224/77A patent/GB1572358A/en not_active Expired
- 1977-03-23 NO NO771032A patent/NO771032L/no unknown
- 1977-03-23 SE SE7703353A patent/SE436496B/xx unknown
- 1977-03-23 AT AT203577A patent/AT360003B/de not_active IP Right Cessation
- 1977-03-24 AU AU23572/77A patent/AU508330B2/en not_active Expired
- 1977-03-24 FI FI770930A patent/FI770930A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
MC1133A1 (fr)	1977-11-18
FR2345443B1 (fr)	1979-03-09
DK129277A (da)	1977-09-25
IE44727B1 (en)	1982-03-10
AU2357277A (en)	1978-09-28
NL7703143A (nl)	1977-09-27
AT360003B (de)	1980-12-10
BE852778A (fr)	1977-09-23
IE44727L (en)	1977-09-24
IL51718A (en)	1980-11-30
ZA771722B (en)	1978-02-22
PT66343B (en)	1979-01-18
IL51718A0 (en)	1977-05-31
CA1104144A (fr)	1981-06-30
AU508330B2 (en)	1980-03-20
GR62464B (en)	1979-04-13
SE7703353L (sv)	1977-11-07
NZ183656A (en)	1979-01-11
ES457132A1 (es)	1978-08-16
FI770930A7 (fr)	1977-09-25
GB1572358A (en)	1980-07-30
DE2712045A1 (de)	1977-09-29
SE436496B (sv)	1984-12-17
PT66343A (en)	1977-04-01
JPS52116461A (en)	1977-09-29
ATA203577A (de)	1980-05-15
NO771032L (no)	1977-09-27
PH13274A (en)	1980-02-27
FR2345443A1 (fr)	1977-10-21
LU76997A1 (fr)	1978-06-01

Legal Events

Date	Code	Title	Description
1986-11-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0004279B1 (fr)	1982-12-29	Procédé pour la préparation d'acides 4-pyridone-3-carboxyliques, dérivés d'acides 1-cyclopropyl-4-pyridone-3-carboxyliques et médicament les contenant
EP0005528B1 (fr)	1983-03-23	Dérivés de l'imidazole, leur préparation et compositions pharmaceutiques
DE3324034C2 (fr)	1993-07-01
EP0026848B1 (fr)	1983-05-04	Dérivés de tétraline, leur préparation et médicaments contenant ces composés
DD229116A5 (de)	1985-10-30	Verfahren zur herstellung von phenylverbindungen
DD201793A5 (de)	1983-08-10	Verfahren zur herstellung von 6-hydroxy-2-(4-hydroxy-phenyl) 3-(4-(2-aminoethoxy)benzoyl)benzo(b)thiophenen
DE2537070C2 (fr)	1987-06-25
EP0071935B1 (fr)	1985-11-13	Composés du 1-phényl-2-aminocarbonylindole, procédé de préparation et intermédiaires et médicaments contenant ces composés
CH632495A5 (de)	1982-10-15	Verfahren zur herstellung neuer substituierter pyridine.
DE3304019A1 (de)	1984-08-09	3-acyloxy-1-phenyl-2-aminocarbonylindol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH628045A5 (en)	1982-02-15	Process for the preparation of dibenzothiophene derivatives
DE2118315C3 (de)	1975-04-03	2-(1H)-Chinazolinonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2315148A1 (de)	1973-10-18	Neue chinolinderivate, verfahren zu ihrer herstellung und ihre verwendung
DE2623314C2 (de)	1984-08-02	1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
US4219657A (en)	1980-08-26	Dibenzothiophenes
DE2131330A1 (de)	1972-01-05	Imidazo-[1,2-a]-benzimidazolderivate und Verfahren zur Herstellung derselben
DE3300522C2 (fr)	1992-01-09
DE2811312A1 (de)	1979-09-27	Neue isochinolinderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von arzneimitteln
EP0371342B1 (fr)	1994-12-14	2-Halogéno N-indolyléthyl sulfonamides, procédé pour leur préparation et leur utilisation en thérapeutique
DE2635064C2 (de)	1986-07-24	Arzneimittel, enthaltend ein 2-(1-Hydroxyäthyl)-benzofuranderivat, 2-(1-Hydroxyäthyl)-benzofuranderivate als solche und Verfahren zu ihrer Herstellung
DD210266A5 (de)	1984-06-06	Verfahren zur herstellung von 3-(ureidocyclohexylamino)-propan-1,2-diolderivaten
DE3331612A1 (de)	1984-03-08	Substituierte 1-pyridyloxy-3-indolylalkylamino-2-propanole, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische mittel
DE2711656A1 (de)	1978-09-21	Neue pyridin-3-ole
DE2827824A1 (de)	1979-01-18	Alpha-acetylenische aminosaeuren
DE3217206C2 (fr)	1992-05-14