CA1148567A - Basic ethers of 7-oxo-7h-benzo/c/fluorene and a process for their production - Google Patents
Basic ethers of 7-oxo-7h-benzo/c/fluorene and a process for their productionInfo
- Publication number
- CA1148567A CA1148567A CA000370028A CA370028A CA1148567A CA 1148567 A CA1148567 A CA 1148567A CA 000370028 A CA000370028 A CA 000370028A CA 370028 A CA370028 A CA 370028A CA 1148567 A CA1148567 A CA 1148567A
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- fluorene
- benzo
- dimethylamino
- ethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims description 21
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- CMGHSVGJLXOGMT-UHFFFAOYSA-N 5-hydroxybenzo[c]fluoren-7-one Chemical compound C12=CC=CC=C2C(O)=CC2=C1C1=CC=CC=C1C2=O CMGHSVGJLXOGMT-UHFFFAOYSA-N 0.000 claims abstract 7
- USYWCEDYVLPNHH-UHFFFAOYSA-N benzo[c]fluoren-7-one Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C12 USYWCEDYVLPNHH-UHFFFAOYSA-N 0.000 claims abstract 7
- 238000007281 aminoalkylation reaction Methods 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 22
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000004820 halides Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 claims description 2
- IALAUUKEGMAATC-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]benzo[c]fluoren-7-one Chemical compound C12=CC=CC=C2C(OCCN(C)C)=CC2=C1C1=CC=CC=C1C2=O IALAUUKEGMAATC-UHFFFAOYSA-N 0.000 claims 9
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 claims 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229960000443 hydrochloric acid Drugs 0.000 claims 3
- 235000011167 hydrochloric acid Nutrition 0.000 claims 3
- GCGNIHJLBYAAHW-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-[2-(dimethylamino)ethoxy]benzo[c]fluoren-7-one Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2C(OCCN(C)C)=CC2=C1C1=CC=CC=C1C2=O GCGNIHJLBYAAHW-BTJKTKAUSA-N 0.000 claims 2
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 claims 2
- YFULOKPMQSJFEA-UHFFFAOYSA-N 3,9-diethyl-5-hydroxybenzo[c]fluoren-7-one Chemical compound C1=C(CC)C=CC2=C3C4=CC=C(CC)C=C4C(=O)C3=CC(O)=C21 YFULOKPMQSJFEA-UHFFFAOYSA-N 0.000 claims 2
- CJJIGZKABUHREN-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-3,9-diethylbenzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C12=CC=C(CC)C=C2C(OCCN(CC)CC)=CC2=C1C1=CC=C(CC)C=C1C2=O CJJIGZKABUHREN-UHFFFAOYSA-N 0.000 claims 2
- WEHXRNCFDWYEPL-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-3,9-dimethylbenzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C12=CC=C(C)C=C2C(OCCN(CC)CC)=CC2=C1C1=CC=C(C)C=C1C2=O WEHXRNCFDWYEPL-UHFFFAOYSA-N 0.000 claims 2
- FWEFGCANMRZXEA-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-3,9-diethylbenzo[c]fluoren-7-one Chemical compound C1=C(CC)C=CC2=C3C4=CC=C(CC)C=C4C(=O)C3=CC(OCCN(C)C)=C21 FWEFGCANMRZXEA-UHFFFAOYSA-N 0.000 claims 2
- VFCSSXLVWGPFLS-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-3,9-dimethylbenzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C12=CC=C(C)C=C2C(OCCN(C)C)=CC2=C1C1=CC=C(C)C=C1C2=O VFCSSXLVWGPFLS-UHFFFAOYSA-N 0.000 claims 2
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 claims 1
- QLCHXZVEEOWYHL-UHFFFAOYSA-N 3-chloro-n,n,2,2-tetramethylpropan-1-amine;hydrochloride Chemical compound Cl.CN(C)CC(C)(C)CCl QLCHXZVEEOWYHL-UHFFFAOYSA-N 0.000 claims 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 claims 1
- ZMRXPEZLFYLMTF-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-3,9-diethylbenzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C1=C(CC)C=CC2=C3C4=CC=C(CC)C=C4C(=O)C3=CC(OCCN(C)C)=C21 ZMRXPEZLFYLMTF-UHFFFAOYSA-N 0.000 claims 1
- QDICPURQHOGPKE-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-3,9-dimethylbenzo[c]fluoren-7-one Chemical compound C12=CC=C(C)C=C2C(OCCN(C)C)=CC2=C1C1=CC=C(C)C=C1C2=O QDICPURQHOGPKE-UHFFFAOYSA-N 0.000 claims 1
- OFWSUMVWAUPJTK-UHFFFAOYSA-N 5-[3-(dimethylamino)-2,2-dimethylpropoxy]benzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OCC(C)(C)CN(C)C)=CC2=C1C1=CC=CC=C1C2=O OFWSUMVWAUPJTK-UHFFFAOYSA-N 0.000 claims 1
- DKQZYURYTXKHOS-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]benzo[c]fluoren-7-one Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=CC2=C1C1=CC=CC=C1C2=O DKQZYURYTXKHOS-UHFFFAOYSA-N 0.000 claims 1
- AVLMCFFMUBNZAS-UHFFFAOYSA-N 5-hydroxy-3,9-dimethylbenzo[c]fluoren-7-one Chemical compound C1=C(C)C=CC2=C3C4=CC=C(C)C=C4C(=O)C3=CC(O)=C21 AVLMCFFMUBNZAS-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- LAKCFPPNDVNRFI-UHFFFAOYSA-N Cl.C(C)N(CCOC1=CC=2C(C=3C=CC=CC3C2C2=C1C=CC=C2)=O)CC Chemical compound Cl.C(C)N(CCOC1=CC=2C(C=3C=CC=CC3C2C2=C1C=CC=C2)=O)CC LAKCFPPNDVNRFI-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- FEDBYSNFQHOGCJ-UHFFFAOYSA-N dimethyl-[2-(7-oxobenzo[c]fluoren-5-yl)oxyethyl]azanium;chloride Chemical compound [Cl-].C12=CC=CC=C2C(OCC[NH+](C)C)=CC2=C1C1=CC=CC=C1C2=O FEDBYSNFQHOGCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000004436 sodium atom Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 9
- 150000007522 mineralic acids Chemical class 0.000 abstract description 4
- 150000007524 organic acids Chemical class 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 3
- 208000032839 leukemia Diseases 0.000 abstract description 3
- 235000005985 organic acids Nutrition 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 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 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 e.g. Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229960000643 adenine Drugs 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004474 valine Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- USYYTAZBXJZVHZ-UHFFFAOYSA-N ethanesulfonic acid;methane Chemical compound C.CCS(O)(=O)=O USYYTAZBXJZVHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- GTVRLHPVICIJFQ-UHFFFAOYSA-N hexane;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.CCCCCC GTVRLHPVICIJFQ-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/24—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CSPV753-80 | 1980-02-04 | ||
| CS80753A CS212669B1 (en) | 1980-02-04 | 1980-02-04 | Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1148567A true CA1148567A (en) | 1983-06-21 |
Family
ID=5340229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000370028A Expired CA1148567A (en) | 1980-02-04 | 1981-02-04 | Basic ethers of 7-oxo-7h-benzo/c/fluorene and a process for their production |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4661297A (en, 2012) |
| JP (1) | JPS56122335A (en, 2012) |
| AR (1) | AR227171A1 (en, 2012) |
| AT (1) | AT368127B (en, 2012) |
| BE (1) | BE887327A (en, 2012) |
| CA (1) | CA1148567A (en, 2012) |
| CH (1) | CH647227A5 (en, 2012) |
| CS (1) | CS212669B1 (en, 2012) |
| DE (1) | DE3102597A1 (en, 2012) |
| DK (1) | DK157676C (en, 2012) |
| ES (1) | ES8200633A1 (en, 2012) |
| FI (1) | FI73664C (en, 2012) |
| FR (1) | FR2475038B1 (en, 2012) |
| GB (1) | GB2068374B (en, 2012) |
| SE (1) | SE453186B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS212669B1 (en) * | 1980-02-04 | 1982-03-26 | Jiri Krepelka | Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof |
| TW200530373A (en) * | 2003-12-12 | 2005-09-16 | Sumitomo Chemical Co | Polymer and light-emitting element using said polymer |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
| US3350405A (en) * | 1964-10-16 | 1967-10-31 | Sterling Drug Inc | Amino-lower-alkoxy-dibenzo [a, d] cyclohepten-5-ones and 10, 11-dihydro derivatives thereof |
| IL33573A (en) * | 1968-12-30 | 1973-10-25 | Richardson Merrell Inc | Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene |
| US3707471A (en) * | 1970-04-27 | 1972-12-26 | Richardson Merrell Inc | Fluoranthene bis-basic ethers and thioethers |
| DE2123992C3 (de) * | 1971-05-14 | 1981-03-19 | Richardson-Merrell Inc., New York, N.Y. | 3,9-Bis-äther des Fluoranthens und deren Herstellung |
| US3869496A (en) * | 1972-12-21 | 1975-03-04 | Richardson Merrell Inc | 2,7-bis-basic esters and ethers of 9-benzylidenefluorence |
| US4169897A (en) * | 1972-12-21 | 1979-10-02 | Richardson-Merrell Inc. | 2,7-bis-basic ethers of 9-phenanthrol and 9-loweralkoxy phenanthrol |
| US3892776A (en) * | 1974-03-08 | 1975-07-01 | Richardson Merrell Inc | N-oxides of bis-basic tricyclic ethers |
| CS212669B1 (en) * | 1980-02-04 | 1982-03-26 | Jiri Krepelka | Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof |
-
1980
- 1980-02-04 CS CS80753A patent/CS212669B1/cs unknown
-
1981
- 1981-01-16 AT AT0015981A patent/AT368127B/de not_active IP Right Cessation
- 1981-01-22 FR FR8101162A patent/FR2475038B1/fr not_active Expired
- 1981-01-27 DE DE3102597A patent/DE3102597A1/de active Granted
- 1981-01-29 SE SE8100616A patent/SE453186B/sv not_active IP Right Cessation
- 1981-01-29 AR AR284121A patent/AR227171A1/es active
- 1981-01-30 BE BE0/203665A patent/BE887327A/fr unknown
- 1981-01-30 GB GB8102938A patent/GB2068374B/en not_active Expired
- 1981-02-02 CH CH669/81A patent/CH647227A5/de not_active IP Right Cessation
- 1981-02-03 FI FI810303A patent/FI73664C/fi not_active IP Right Cessation
- 1981-02-03 ES ES499696A patent/ES8200633A1/es not_active Expired
- 1981-02-04 JP JP1448181A patent/JPS56122335A/ja active Granted
- 1981-02-04 CA CA000370028A patent/CA1148567A/en not_active Expired
- 1981-02-04 DK DK048881A patent/DK157676C/da active
-
1982
- 1982-09-14 US US06/417,834 patent/US4661297A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SE453186B (sv) | 1988-01-18 |
| GB2068374A (en) | 1981-08-12 |
| JPS56122335A (en) | 1981-09-25 |
| JPS636059B2 (en, 2012) | 1988-02-08 |
| ATA15981A (de) | 1982-01-15 |
| DE3102597A1 (de) | 1982-01-07 |
| CH647227A5 (de) | 1985-01-15 |
| SE8100616L (sv) | 1981-08-05 |
| FR2475038A1 (fr) | 1981-08-07 |
| BE887327A (fr) | 1981-05-14 |
| US4661297A (en) | 1987-04-28 |
| CS212669B1 (en) | 1982-03-26 |
| AR227171A1 (es) | 1982-09-30 |
| GB2068374B (en) | 1983-06-02 |
| ES499696A0 (es) | 1981-12-01 |
| FI810303L (fi) | 1981-08-05 |
| DK48881A (da) | 1981-08-05 |
| FI73664C (fi) | 1987-11-09 |
| DE3102597C2 (en, 2012) | 1990-07-05 |
| DK157676C (da) | 1990-07-16 |
| FI73664B (fi) | 1987-07-31 |
| ES8200633A1 (es) | 1981-12-01 |
| AT368127B (de) | 1982-09-10 |
| DK157676B (da) | 1990-02-05 |
| FR2475038B1 (fr) | 1985-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |