CH630885A5 - Process for preparing tricyclic compounds, and the use of these compounds. - Google Patents
Process for preparing tricyclic compounds, and the use of these compounds. Download PDFInfo
- Publication number
- CH630885A5 CH630885A5 CH1316472A CH1316472A CH630885A5 CH 630885 A5 CH630885 A5 CH 630885A5 CH 1316472 A CH1316472 A CH 1316472A CH 1316472 A CH1316472 A CH 1316472A CH 630885 A5 CH630885 A5 CH 630885A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- alkyl
- compounds
- formula
- acyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 77
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 claims description 80
- 239000000243 solution Substances 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 51
- 239000007787 solid Substances 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 44
- XMIFYVJZYNTBTI-UHFFFAOYSA-N 9-oxofluorene-2,7-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)C3=CC(C(=O)O)=CC=C3C2=C1 XMIFYVJZYNTBTI-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- -1 N-substituted carboxamide group Chemical group 0.000 claims description 19
- 150000001768 cations Chemical class 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 11
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- RIRYGERFWHUZBT-UHFFFAOYSA-N 1-(7-acetyl-9h-fluoren-2-yl)ethanone Chemical compound CC(=O)C1=CC=C2C3=CC=C(C(=O)C)C=C3CC2=C1 RIRYGERFWHUZBT-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229940117975 chromium trioxide Drugs 0.000 claims description 8
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 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 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 150000007942 carboxylates Chemical group 0.000 claims 5
- 239000011575 calcium Substances 0.000 claims 4
- 229910052791 calcium Inorganic materials 0.000 claims 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical class [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
- 229940096405 magnesium cation Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- ZUTFCPOKQHJATC-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ZUTFCPOKQHJATC-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000004604 Blowing Agent Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 201000009961 allergic asthma Diseases 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 150000004682 monohydrates Chemical class 0.000 description 6
- 230000002685 pulmonary effect Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- 239000003341 Bronsted base Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000004683 dihydrates Chemical class 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010039085 Rhinitis allergic Diseases 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 201000010105 allergic rhinitis Diseases 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 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
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- JHMVPGWDPZHTSF-UHFFFAOYSA-N 1-(7-ethyl-9h-fluoren-2-yl)ethanone Chemical compound CC(=O)C1=CC=C2C3=CC=C(CC)C=C3CC2=C1 JHMVPGWDPZHTSF-UHFFFAOYSA-N 0.000 description 2
- AYRABHFHMLXKBT-UHFFFAOYSA-N 2,6-dimethylanthracene Chemical compound C1=C(C)C=CC2=CC3=CC(C)=CC=C3C=C21 AYRABHFHMLXKBT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- KKGMWTBOMVOLEQ-UHFFFAOYSA-N 2-butyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CCCC)C=C3CC2=C1 KKGMWTBOMVOLEQ-UHFFFAOYSA-N 0.000 description 2
- IAGPYKKRRMNDCQ-UHFFFAOYSA-N 2-ethyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CC)C=C3CC2=C1 IAGPYKKRRMNDCQ-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- XNKPQVUJZSWOAR-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 XNKPQVUJZSWOAR-UHFFFAOYSA-N 0.000 description 2
- BJCTXUUKONLPPK-UHFFFAOYSA-N 9-oxofluorene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C2=C1 BJCTXUUKONLPPK-UHFFFAOYSA-N 0.000 description 2
- IJIGJAXLVRAISI-UHFFFAOYSA-N 9-oxoxanthene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)C3=CC=C(C(=O)O)C=C3OC2=C1 IJIGJAXLVRAISI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 239000001488 sodium phosphate Substances 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
- C07C49/653—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
- C07C65/36—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C66/00—Quinone carboxylic acids
- C07C66/02—Anthraquinone carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4185271 | 1971-09-08 | ||
GB861072 | 1972-02-24 | ||
GB860972 | 1972-02-24 | ||
GB860872*[A GB1414621A (en) | 1971-09-08 | 1972-02-24 | Tricyclic compounds having antiallergic properties and pharmaceuti cal compositions thereof |
GB1490972 | 1972-03-29 | ||
GB3581872 | 1972-08-01 | ||
GB4007972 | 1972-08-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH630885A5 true CH630885A5 (en) | 1982-07-15 |
Family
ID=27562567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1316472A CH630885A5 (en) | 1971-09-08 | 1972-09-07 | Process for preparing tricyclic compounds, and the use of these compounds. |
Country Status (11)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007012254A1 (en) | 2005-07-11 | 2007-02-01 | Jiangsu Lianchuang Pharmaceutical Technology Co., Ltd | Rhein conjugates, preparation method thereof and their uses in producing medicines for treating diabetic nephrosis, intestinal adhesion and osteoarthritis |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS55122785A (en) * | 1979-03-15 | 1980-09-20 | Yoshitomi Pharmaceut Ind Ltd | Preparation of benzopyranopyridine derivative |
FR2464937A1 (fr) * | 1979-09-13 | 1981-03-20 | Interox | Procede pour la fabrication d'anthraquinones substituees |
US4585876A (en) * | 1982-11-25 | 1986-04-29 | Ciba-Geigy Corporation | Novel xanthones and thioxanthones |
JPS59175840A (ja) * | 1983-03-24 | 1984-10-04 | イカリ消毒株式会社 | 土中小動物の駆除方法 |
JPS6034901A (ja) * | 1984-06-04 | 1985-02-22 | Nippon Nohyaku Co Ltd | 害虫等の予防及び駆除方法 |
US4714669A (en) * | 1985-04-11 | 1987-12-22 | Ciba-Geigy Corporation | Radiation-sensitive polycondensates, their preparation, material coated therewith and the use thereof |
TW200301698A (en) | 2001-12-21 | 2003-07-16 | Bristol Myers Squibb Co | Acridone inhibitors of IMPDH enzyme |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1833272A (en) * | 1928-06-21 | 1931-11-24 | Gen Aniline Works Inc | Beta-anthraquinone-carboxylic acids and the esters thereof and process of preparing them |
DE495100C (de) * | 1928-06-22 | 1930-04-07 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von ª‰-Anthrachinoncarbonsaeuren und deren Estern |
NL7008621A (enrdf_load_stackoverflow) * | 1969-06-25 | 1970-12-29 | ||
US3642997A (en) * | 1969-06-25 | 1972-02-15 | Merck & Co Inc | Tricyclic carboxylic acids in the treatment of inflammation |
US3873538A (en) * | 1970-08-05 | 1975-03-25 | Allen & Hanburys Ltd | Amino-9,10-dihydro-9,10-dioxo-2-anthroic acids |
-
1972
- 1972-09-07 FR FR7231756A patent/FR2154476B1/fr not_active Expired
- 1972-09-07 LU LU66018A patent/LU66018A1/xx unknown
- 1972-09-07 IL IL40320A patent/IL40320A/en unknown
- 1972-09-07 BE BE788514D patent/BE788514A/xx not_active IP Right Cessation
- 1972-09-07 NL NL7212174A patent/NL7212174A/xx not_active Application Discontinuation
- 1972-09-07 DD DD179483*A patent/DD114946A5/xx unknown
- 1972-09-07 DE DE2243997A patent/DE2243997A1/de not_active Ceased
- 1972-09-07 JP JP47089979A patent/JPS4834865A/ja active Pending
- 1972-09-07 DD DD165511A patent/DD106263A5/xx unknown
- 1972-09-07 CH CH1316472A patent/CH630885A5/de not_active IP Right Cessation
- 1972-09-07 IE IE1220/72A patent/IE37007B1/xx unknown
- 1972-09-07 AR AR243958A patent/AR209571A1/es active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007012254A1 (en) | 2005-07-11 | 2007-02-01 | Jiangsu Lianchuang Pharmaceutical Technology Co., Ltd | Rhein conjugates, preparation method thereof and their uses in producing medicines for treating diabetic nephrosis, intestinal adhesion and osteoarthritis |
EP1913940A4 (en) * | 2005-07-11 | 2010-03-31 | Xiaodong Cong | RHEIN CONJUGATES, PREPARATION METHOD AND ITS USE IN THE MANUFACTURE OF MEDICAMENTS FOR THE TREATMENT OF DIABETIC NEPHROSIS, DARMADHESION AND OSTEOARTHRITIS |
RU2416596C2 (ru) * | 2005-07-11 | 2011-04-20 | Джиангсу Лианчуанг Фармацёйтикал Текнолоджи Ко., Лтд | Конъюгат хризофанола, способ его получения, применение его в качестве лекарственного средства для лечения диабетической нефропатии, спаек кишок, остеоартрита |
Also Published As
Publication number | Publication date |
---|---|
JPS4834865A (enrdf_load_stackoverflow) | 1973-05-22 |
BE788514A (fr) | 1973-03-07 |
DD106263A5 (enrdf_load_stackoverflow) | 1974-06-12 |
LU66018A1 (enrdf_load_stackoverflow) | 1973-03-12 |
AU4640672A (en) | 1974-03-14 |
AR209571A1 (es) | 1977-05-13 |
DE2243997A1 (de) | 1973-03-15 |
DD114946A5 (enrdf_load_stackoverflow) | 1975-09-05 |
NL7212174A (enrdf_load_stackoverflow) | 1973-03-12 |
FR2154476B1 (enrdf_load_stackoverflow) | 1975-10-17 |
IE37007L (en) | 1973-03-08 |
FR2154476A1 (enrdf_load_stackoverflow) | 1973-05-11 |
IE37007B1 (en) | 1977-04-13 |
IL40320A0 (en) | 1972-11-28 |
IL40320A (en) | 1976-12-31 |
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