CS212669B1 - Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof - Google Patents
Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof Download PDFInfo
- Publication number
- CS212669B1 CS212669B1 CS80753A CS75380A CS212669B1 CS 212669 B1 CS212669 B1 CS 212669B1 CS 80753 A CS80753 A CS 80753A CS 75380 A CS75380 A CS 75380A CS 212669 B1 CS212669 B1 CS 212669B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxo
- formula
- benzo
- ethoxy
- dimethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title description 8
- 150000002148 esters Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 7
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 150000002170 ethers Chemical class 0.000 claims abstract description 4
- 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 description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- -1 methylmethyl Chemical group 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 229910052700 potassium Chemical group 0.000 claims description 3
- 239000011591 potassium Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical group CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical group CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 229940049964 oleate Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 abstract description 10
- 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 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 238000007281 aminoalkylation reaction Methods 0.000 abstract 1
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 230000001506 immunosuppresive effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000004083 survival effect Effects 0.000 description 13
- 230000002035 prolonged effect Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 206010003445 Ascites Diseases 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 238000002474 experimental method Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HEEACTTWORLLPM-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)ethanol Chemical compound OCCC1=CNC=N1 HEEACTTWORLLPM-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
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 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 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
- FRIJWEQBTIZQMD-UHFFFAOYSA-N Benzo[c]fluorene Chemical compound C1=CC2=CC=CC=C2C2=C1CC1=CC=CC=C12 FRIJWEQBTIZQMD-UHFFFAOYSA-N 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- 241001611408 Nebo Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 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
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 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 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- GTVRLHPVICIJFQ-UHFFFAOYSA-N hexane;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.CCCCCC GTVRLHPVICIJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- 230000004614 tumor growth Effects 0.000 description 1
- 239000008096 xylene Substances 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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)
Priority Applications (15)
| 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 |
| AT0015981A AT368127B (de) | 1980-02-04 | 1981-01-16 | Verfahren zur herstellung neuer basischer aether von 7-oxo-7h-benzo/c/fluoren |
| FR8101162A FR2475038B1 (fr) | 1980-02-04 | 1981-01-22 | Ethers basiques de 8-oxo-7h-benzo/c/fluorene, et procede pour la preparation de ces produits |
| DE3102597A DE3102597A1 (de) | 1980-02-04 | 1981-01-27 | Basische aether des 7-oxo-7h-benzo(c)fluorens, ihre herstellung und pharmazeutische mittel |
| SE8100616A SE453186B (sv) | 1980-02-04 | 1981-01-29 | Basiska etrar av 7-oxo-7h-benso/ c / fluoren och sett for framstellning derav |
| AR284121A AR227171A1 (es) | 1980-02-04 | 1981-01-29 | Procedimiento de preparacion de eteres basicos de 7-oxo-7h-benzo/c/fluoreno |
| GB8102938A GB2068374B (en) | 1980-02-04 | 1981-01-30 | Basic ethers of 7-oxo-7h-benzo(c)fluorene |
| BE0/203665A BE887327A (fr) | 1980-02-04 | 1981-01-30 | Ethers basiques de 7-oxo-7h-benzo(c) fluorene et leur procede de preparation |
| CH669/81A CH647227A5 (de) | 1980-02-04 | 1981-02-02 | Basische aether von 7-oxo-7h-benzo-(c)-fluoren und verfahren zu deren herstellung. |
| ES499696A ES8200633A1 (es) | 1980-02-04 | 1981-02-03 | Procedimiento para la produccion de eteres basicos de 7-oxo-7h-benzo(c)fluoreno |
| FI810303A FI73664C (sv) | 1980-02-04 | 1981-02-03 | Förfarande för framställning av farmakologiskt aktiva basiska etrar av 7-oxo-7H-benso/c/fluoren. |
| CA000370028A CA1148567A (en) | 1980-02-04 | 1981-02-04 | Basic ethers of 7-oxo-7h-benzo/c/fluorene and a process for their production |
| DK048881A DK157676C (da) | 1980-02-04 | 1981-02-04 | Analogifremgangsmaade til fremstilling af basiske ethere af 7-oxo-7h-benzooecaa fluoren |
| JP1448181A JPS56122335A (en) | 1980-02-04 | 1981-02-04 | Basic ethers of 77oxoo7hhbenzo*c*fluorene and manufacture |
| US06/417,834 US4661297A (en) | 1980-02-04 | 1982-09-14 | Basic ethers of 7-oxo-7H-benzo(c) fluorene and a process for their production |
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 |
|---|---|
| CS212669B1 true CS212669B1 (en) | 1982-03-26 |
Family
ID=5340229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS80753A CS212669B1 (en) | 1980-02-04 | 1980-02-04 | Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4661297A (sv) |
| JP (1) | JPS56122335A (sv) |
| AR (1) | AR227171A1 (sv) |
| AT (1) | AT368127B (sv) |
| BE (1) | BE887327A (sv) |
| CA (1) | CA1148567A (sv) |
| CH (1) | CH647227A5 (sv) |
| CS (1) | CS212669B1 (sv) |
| DE (1) | DE3102597A1 (sv) |
| DK (1) | DK157676C (sv) |
| ES (1) | ES8200633A1 (sv) |
| FI (1) | FI73664C (sv) |
| FR (1) | FR2475038B1 (sv) |
| GB (1) | GB2068374B (sv) |
| SE (1) | SE453186B (sv) |
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 |
| US4169897A (en) * | 1972-12-21 | 1979-10-02 | Richardson-Merrell Inc. | 2,7-bis-basic ethers of 9-phenanthrol and 9-loweralkoxy phenanthrol |
| US3869496A (en) * | 1972-12-21 | 1975-03-04 | Richardson Merrell Inc | 2,7-bis-basic esters and ethers of 9-benzylidenefluorence |
| 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 ES ES499696A patent/ES8200633A1/es not_active Expired
- 1981-02-03 FI FI810303A patent/FI73664C/sv not_active IP Right Cessation
- 1981-02-04 DK DK048881A patent/DK157676C/da active
- 1981-02-04 JP JP1448181A patent/JPS56122335A/ja active Granted
- 1981-02-04 CA CA000370028A patent/CA1148567A/en not_active Expired
-
1982
- 1982-09-14 US US06/417,834 patent/US4661297A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SE8100616L (sv) | 1981-08-05 |
| DK48881A (da) | 1981-08-05 |
| GB2068374B (en) | 1983-06-02 |
| DK157676B (da) | 1990-02-05 |
| FR2475038B1 (fr) | 1985-06-28 |
| SE453186B (sv) | 1988-01-18 |
| US4661297A (en) | 1987-04-28 |
| JPS636059B2 (sv) | 1988-02-08 |
| DE3102597C2 (sv) | 1990-07-05 |
| CA1148567A (en) | 1983-06-21 |
| FI810303L (fi) | 1981-08-05 |
| FI73664C (sv) | 1987-11-09 |
| ES499696A0 (es) | 1981-12-01 |
| GB2068374A (en) | 1981-08-12 |
| ATA15981A (de) | 1982-01-15 |
| FI73664B (fi) | 1987-07-31 |
| BE887327A (fr) | 1981-05-14 |
| AT368127B (de) | 1982-09-10 |
| FR2475038A1 (fr) | 1981-08-07 |
| AR227171A1 (es) | 1982-09-30 |
| DE3102597A1 (de) | 1982-01-07 |
| JPS56122335A (en) | 1981-09-25 |
| ES8200633A1 (es) | 1981-12-01 |
| CH647227A5 (de) | 1985-01-15 |
| DK157676C (da) | 1990-07-16 |
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