CH647227A5 - Basische aether von 7-oxo-7h-benzo-(c)-fluoren und verfahren zu deren herstellung. - Google Patents
Basische aether von 7-oxo-7h-benzo-(c)-fluoren und verfahren zu deren herstellung. Download PDFInfo
- Publication number
- CH647227A5 CH647227A5 CH669/81A CH66981A CH647227A5 CH 647227 A5 CH647227 A5 CH 647227A5 CH 669/81 A CH669/81 A CH 669/81A CH 66981 A CH66981 A CH 66981A CH 647227 A5 CH647227 A5 CH 647227A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzo
- oxo
- fluorene
- ethoxy
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000002170 ethers Chemical class 0.000 title claims description 3
- 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 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 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 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- -1 5- [2- (diethylamino) ethoxy] -7-oxo-7H-benzo (c) -fluorene Chemical compound 0.000 claims 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 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 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 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 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 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229950006327 napsilate Drugs 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- JFKKPPBTDHLGCA-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-3,9-diethylbenzo[c]fluoren-7-one Chemical compound C12=CC=C(CC)C=C2C(OCCN(CC)CC)=CC2=C1C1=CC=C(CC)C=C1C2=O JFKKPPBTDHLGCA-UHFFFAOYSA-N 0.000 claims 1
- WNLNIVVFWRVLTM-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-3,9-dimethylbenzo[c]fluoren-7-one Chemical compound C12=CC=C(C)C=C2C(OCCN(CC)CC)=CC2=C1C1=CC=C(C)C=C1C2=O WNLNIVVFWRVLTM-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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
- 238000006386 neutralization reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 206010028980 Neoplasm Diseases 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960000643 adenine Drugs 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 238000002054 transplantation Methods 0.000 description 5
- 239000004474 valine Substances 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 229930024421 Adenine Natural products 0.000 description 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 230000004083 survival effect 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
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
- RQTVOHLUMUHECE-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]benzo[c]fluoren-7-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OCCCN(C)C)=CC2=C1C1=CC=CC=C1C2=O RQTVOHLUMUHECE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108010006464 Hemolysin Proteins Proteins 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
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000000185 hemagglutinin Substances 0.000 description 2
- 239000003228 hemolysin Substances 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PLPDHGOODMBBGN-VOTSOKGWSA-N (e)-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-VOTSOKGWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 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 description 1
- 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 description 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 description 1
- 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 description 1
- DXKZEUUVPWJJCX-UHFFFAOYSA-N 9h-fluorene;hydrochloride Chemical compound Cl.C1=CC=C2CC3=CC=CC=C3C2=C1 DXKZEUUVPWJJCX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 101710154606 Hemagglutinin Proteins 0.000 description 1
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 1
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101710176177 Protein A56 Proteins 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
- 239000002253 acid Substances 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- MPMFCABZENCRHV-UHFFFAOYSA-N tilorone Chemical compound C1=C(OCCN(CC)CC)C=C2C(=O)C3=CC(OCCN(CC)CC)=CC=C3C2=C1 MPMFCABZENCRHV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000003799 water insoluble solvent Substances 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| CH647227A5 true CH647227A5 (de) | 1985-01-15 |
Family
ID=5340229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH669/81A CH647227A5 (de) | 1980-02-04 | 1981-02-02 | Basische aether von 7-oxo-7h-benzo-(c)-fluoren und verfahren zu deren herstellung. |
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 |
| CA1148567A (en) | 1983-06-21 |
| 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 |
| 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 |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |