JPS59225149A - 殺生物性多環化合物,その合成法,その中間体,それを含有する製剤および医薬としてのその使用 - Google Patents
殺生物性多環化合物,その合成法,その中間体,それを含有する製剤および医薬としてのその使用Info
- Publication number
- JPS59225149A JPS59225149A JP59099655A JP9965584A JPS59225149A JP S59225149 A JPS59225149 A JP S59225149A JP 59099655 A JP59099655 A JP 59099655A JP 9965584 A JP9965584 A JP 9965584A JP S59225149 A JPS59225149 A JP S59225149A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- propanediol
- amino
- group
- pyrenylmethyl
- 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.)
- Pending
Links
- -1 polycyclic compound Chemical class 0.000 title claims description 181
- 239000003814 drug Substances 0.000 title claims description 17
- 229940079593 drug Drugs 0.000 title description 11
- 230000000361 pesticidal effect Effects 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 139
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 38
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 36
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 32
- 229940035437 1,3-propanediol Drugs 0.000 claims description 32
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Chemical group C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- 229960004592 isopropanol Drugs 0.000 claims description 6
- 238000007911 parenteral administration Methods 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- PGULKQQPMATSHP-UHFFFAOYSA-N 2-ethyl-2-(pyren-1-ylmethylamino)propane-1,3-diol Chemical compound C1=C2C(CNC(CO)(CO)CC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 PGULKQQPMATSHP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- TZNXEWGKCWPLQI-UHFFFAOYSA-N pyren-1-ylmethanamine Chemical compound C1=C2C(CN)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 TZNXEWGKCWPLQI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QRKAYXCMKGJZHZ-UHFFFAOYSA-N 2-methyl-2-(phenanthren-4-ylmethylamino)propane-1,3-diol Chemical compound C1=CC=CC2=C3C(CNC(CO)(CO)C)=CC=CC3=CC=C21 QRKAYXCMKGJZHZ-UHFFFAOYSA-N 0.000 claims 1
- PBIHNSRRIKSORF-UHFFFAOYSA-N 2-methyl-2-(phenanthren-9-ylmethylamino)propane-1,3-diol Chemical compound C1=CC=C2C(CNC(CO)(CO)C)=CC3=CC=CC=C3C2=C1 PBIHNSRRIKSORF-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000005578 chrysene group Chemical group 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
- 238000002844 melting Methods 0.000 description 128
- 230000008018 melting Effects 0.000 description 128
- 238000000034 method Methods 0.000 description 112
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- 239000000203 mixture Substances 0.000 description 79
- 238000000921 elemental analysis Methods 0.000 description 68
- 238000004458 analytical method Methods 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 57
- 229910052799 carbon Inorganic materials 0.000 description 53
- 239000002904 solvent Substances 0.000 description 50
- 239000000126 substance Substances 0.000 description 48
- 238000000354 decomposition reaction Methods 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 238000006268 reductive amination reaction Methods 0.000 description 45
- 239000007787 solid Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 33
- 238000012360 testing method Methods 0.000 description 33
- 235000019441 ethanol Nutrition 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 206010028980 Neoplasm Diseases 0.000 description 26
- 229960004132 diethyl ether Drugs 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 150000001299 aldehydes Chemical group 0.000 description 22
- 229960004756 ethanol Drugs 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002390 rotary evaporation Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 230000000259 anti-tumor effect Effects 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 210000004881 tumor cell Anatomy 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241001024304 Mino Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 229940052303 ethers for general anesthesia Drugs 0.000 description 5
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- RVYNIIJBIAINNT-UHFFFAOYSA-N propane-1,3-diol;hydrochloride Chemical compound Cl.OCCCO RVYNIIJBIAINNT-UHFFFAOYSA-N 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- OARMMULWJINVQP-UHFFFAOYSA-N 1-chrysen-3-ylethanone Chemical compound C1=CC=CC2=CC=C(C=3C(=CC=C(C=3)C(=O)C)C=C3)C3=C21 OARMMULWJINVQP-UHFFFAOYSA-N 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 230000022244 formylation Effects 0.000 description 4
- 238000006170 formylation reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 201000005202 lung cancer Diseases 0.000 description 4
- 208000020816 lung neoplasm Diseases 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 3
- HFWVQJWTYKKQTE-UHFFFAOYSA-N 1-chrysen-2-ylethanone Chemical compound C1=CC=CC2=CC=C3C4=CC=C(C(=O)C)C=C4C=CC3=C21 HFWVQJWTYKKQTE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- ZFKMDRNOZXVYEW-UHFFFAOYSA-N 6-(chloromethyl)chrysene Chemical compound C1=CC=C2C(CCl)=CC3=C(C=CC=C4)C4=CC=C3C2=C1 ZFKMDRNOZXVYEW-UHFFFAOYSA-N 0.000 description 3
- IABVGDXQWWLUDA-UHFFFAOYSA-N 9-butoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=CC2=C1 IABVGDXQWWLUDA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 206010003445 Ascites Diseases 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
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- SFKTYEXKZXBQRQ-UHFFFAOYSA-J thorium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Th+4] SFKTYEXKZXBQRQ-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/20—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated the carbon skeleton being saturated and containing rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
- C07C205/15—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07C217/48—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 unsaturated and containing rings
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- 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
-
- 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
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered 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
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
-
- 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
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB838313571A GB8313571D0 (en) | 1983-05-17 | 1983-05-17 | Chemical compounds |
GB8313571 | 1983-05-17 | ||
APAP/P/1984/000003A AP1A (en) | 1983-05-17 | 1984-07-16 | Polycyclic aromatic compounds |
Publications (1)
Publication Number | Publication Date |
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JPS59225149A true JPS59225149A (ja) | 1984-12-18 |
Family
ID=39791481
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
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JP59099655A Pending JPS59225149A (ja) | 1983-05-17 | 1984-05-16 | 殺生物性多環化合物,その合成法,その中間体,それを含有する製剤および医薬としてのその使用 |
JP59099656A Granted JPS59225150A (ja) | 1983-05-17 | 1984-05-16 | 殺生物性芳香族化合物、その合成および医薬としてのその使用 |
JP2144246A Expired - Lifetime JPH0684336B2 (ja) | 1983-05-17 | 1990-06-01 | 殺生物性芳香族化合物、その合成および医薬としてのその使用 |
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Application Number | Title | Priority Date | Filing Date |
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JP59099656A Granted JPS59225150A (ja) | 1983-05-17 | 1984-05-16 | 殺生物性芳香族化合物、その合成および医薬としてのその使用 |
JP2144246A Expired - Lifetime JPH0684336B2 (ja) | 1983-05-17 | 1990-06-01 | 殺生物性芳香族化合物、その合成および医薬としてのその使用 |
Country Status (30)
Families Citing this family (51)
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US4803221A (en) * | 1977-03-15 | 1989-02-07 | Burroughs Wellcome Co. | Anthracene derivatives |
US4719046A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Crysene derivatives |
US4803226A (en) * | 1983-05-17 | 1989-02-07 | Burroughs Wellcome Co. | Anthracene derivatives |
US4810727A (en) * | 1983-05-17 | 1989-03-07 | Burroughs Wellcome Co. | Chrysene compound |
US4829090A (en) * | 1983-05-17 | 1989-05-09 | Burroughs Wellcome Co. | Chrysene derivatives |
US4719055A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4719048A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Crysene compound |
US4808625A (en) * | 1983-05-17 | 1989-02-28 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4808632A (en) * | 1983-05-17 | 1989-02-28 | Burroughs Wellcome Co. | Fluoranthene derivatives |
US4803222A (en) * | 1983-05-17 | 1989-02-07 | Burroughs Wellcome Co. | Fluoranthene derivatives |
GB8313571D0 (en) * | 1983-05-17 | 1983-06-22 | Wellcome Found | Chemical compounds |
US4717729A (en) * | 1983-05-31 | 1988-01-05 | Burroughs Wellcome Co. | Triphenylene derivatives |
GB8428931D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
GB8428932D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
KR900008814B1 (ko) * | 1984-11-15 | 1990-11-30 | 더 웰컴 파운데이숀 리미티드 | 살균성 폴리시클릭 화합물의 제조방법 |
GB8428930D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
US4808753A (en) * | 1985-11-22 | 1989-02-28 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4827034A (en) * | 1985-11-22 | 1989-05-02 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4818443A (en) * | 1985-11-22 | 1989-04-04 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4791232A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US5008286A (en) * | 1985-11-22 | 1991-04-16 | Burroughs Wellcome Co. | Certain substituted naphthofurans with anti-tumor properties |
US4791233A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4791231A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4810823A (en) * | 1985-11-22 | 1989-03-07 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4814502A (en) * | 1985-11-22 | 1989-03-21 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4882358A (en) * | 1985-11-22 | 1989-11-21 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US5435667A (en) * | 1986-02-20 | 1995-07-25 | Slickbar Products Corp. | Protection of piles |
JP2735609B2 (ja) * | 1989-03-31 | 1998-04-02 | 協和醗酵工業株式会社 | Ucn―1028d誘導体 |
US5416244A (en) * | 1991-09-30 | 1995-05-16 | Ohmeda Pharmaceutical Products Division Inc. | Preparation of isoflurane |
JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
EP1021397A4 (en) * | 1997-03-05 | 2000-10-04 | Trimeris Inc | BENZANTHRONE COMPOUNDS AND THEIR USE AGAINST VIRUSES |
FR2775286B1 (fr) * | 1998-02-20 | 2001-09-07 | Centre Nat Rech Scient | Derives du triphenylene contre le sida |
US6015811A (en) * | 1998-10-27 | 2000-01-18 | Board Of Regents, The University Of Texas System | Antitumor Chrysene derivatives |
AU777627B2 (en) * | 1999-12-30 | 2004-10-21 | Kimberly-Clark Worldwide, Inc. | An anti-viral lotion composition and a lotioned tissue product |
US6372785B1 (en) * | 2000-05-04 | 2002-04-16 | Keith Chan, President Globoasia, Llc | Synthesis of 1,8-dichloro-anthracene analogues and pharmaceutical compositions based thereon |
US20050107430A1 (en) * | 2003-10-29 | 2005-05-19 | Banik Bimal K. | Antimicrobial and antiviral compounds |
WO2005089094A2 (en) * | 2003-11-21 | 2005-09-29 | The Board Of Regents Of The University And Community College System Of Nevada | Materials and methods for the preparation of anisotropically-ordered solids |
WO2005119223A1 (en) * | 2004-04-14 | 2005-12-15 | Bioprocessors Corp. | Compositions of matter useful as ph indicators and related methods |
KR100872692B1 (ko) * | 2006-03-06 | 2008-12-10 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 |
RU2349311C1 (ru) * | 2007-08-02 | 2009-03-20 | Михаил Владимирович Кутушов | Применение дериватов нафталина в качестве средств для лечения онкологических заболеваний |
US20170313920A1 (en) | 2010-10-06 | 2017-11-02 | Thomas P. Daly | Biological Buffers with Wide Buffering Ranges |
US8334402B2 (en) * | 2008-04-17 | 2012-12-18 | Thomas Daly | Biological buffers with wide buffering ranges |
US8034951B2 (en) | 2008-04-17 | 2011-10-11 | Thomas Daly | Biological buffers with wide buffering ranges |
US8822728B2 (en) | 2008-04-17 | 2014-09-02 | Thomas Daly | Biological buffers with wide buffering ranges |
US9447310B2 (en) | 2008-04-17 | 2016-09-20 | Thomas P. Daly | Biological buffers with wide buffering ranges |
US9090638B2 (en) | 2008-04-17 | 2015-07-28 | Thomas Daly | Biological buffers with wide buffering ranges |
US7939659B2 (en) * | 2008-04-17 | 2011-05-10 | Thomas Daly | Biological buffers with wide buffering ranges |
US7635791B2 (en) * | 2008-04-17 | 2009-12-22 | Tpat Ip Llc | Biological buffers with wide buffering ranges |
US8519141B2 (en) | 2008-04-17 | 2013-08-27 | Thomas Daly | Biological buffers with wide buffering ranges |
US9475754B2 (en) | 2011-10-06 | 2016-10-25 | Thomas P. Daly | Biological buffers with wide buffering ranges |
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JPS5999656A (ja) * | 1982-11-30 | 1984-06-08 | Toshiba Corp | 筒形空気電池 |
GB8313571D0 (en) * | 1983-05-17 | 1983-06-22 | Wellcome Found | Chemical compounds |
US4511582A (en) * | 1983-06-01 | 1985-04-16 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4532344A (en) * | 1983-05-23 | 1985-07-30 | Burroughs Wellcome Co. | Fluoranthene derivatives |
US4551282A (en) * | 1983-05-31 | 1985-11-05 | Burroughs Wellcome Co. | Triphenylene derivatives |
US4997249A (en) * | 1990-02-26 | 1991-03-05 | The United States Of America As Represented By The Secretary Of The Navy | Variable weight fiber optic transversal filter |
-
1983
- 1983-05-17 GB GB838313571A patent/GB8313571D0/en active Pending
- 1983-06-01 US US06/499,813 patent/US4530800A/en not_active Expired - Lifetime
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1984
- 1984-05-16 PH PH30683A patent/PH22265A/en unknown
- 1984-05-16 IE IE120384A patent/IE58416B1/en unknown
- 1984-05-16 MC MC841705A patent/MC1595A1/xx unknown
- 1984-05-16 NZ NZ208168A patent/NZ208168A/en unknown
- 1984-05-16 DE DE8484105584T patent/DE3473141D1/de not_active Expired
- 1984-05-16 EP EP84105584A patent/EP0125701B1/en not_active Expired
- 1984-05-16 AU AU28098/84A patent/AU572509B2/en not_active Ceased
- 1984-05-16 JP JP59099655A patent/JPS59225149A/ja active Pending
- 1984-05-16 IL IL71854A patent/IL71851A/xx not_active IP Right Cessation
- 1984-05-16 GB GB08412485A patent/GB2140416B/en not_active Expired
- 1984-05-16 EP EP84105585A patent/EP0125702B1/en not_active Expired
- 1984-05-16 JP JP59099656A patent/JPS59225150A/ja active Granted
- 1984-05-16 EG EG315/84A patent/EG17595A/xx active
- 1984-05-16 DE DE8484105585T patent/DE3465296D1/de not_active Expired
- 1984-05-16 DK DK242284A patent/DK242284A/da not_active Application Discontinuation
- 1984-05-16 FI FI841966A patent/FI85263C/fi not_active IP Right Cessation
- 1984-05-16 KR KR1019840002647A patent/KR910000854B1/ko not_active Expired
- 1984-05-16 CA CA000454514A patent/CA1222750A/en not_active Expired
- 1984-05-16 DD DD84263086A patent/DD223439A5/de not_active IP Right Cessation
- 1984-05-16 SU SU843744951A patent/SU1535377A3/ru active
- 1984-05-16 CS CS364584A patent/CS273314B2/cs unknown
- 1984-05-16 NO NO841954A patent/NO157416C/no unknown
- 1984-05-16 GR GR74735A patent/GR82278B/el unknown
- 1984-05-16 ZA ZA843708A patent/ZA843708B/xx unknown
- 1984-05-16 PT PT78586A patent/PT78586A/pt not_active IP Right Cessation
- 1984-05-16 HU HU841886A patent/HU197875B/hu not_active IP Right Cessation
- 1984-05-16 ES ES532512A patent/ES8603376A1/es not_active Expired
- 1984-05-17 PL PL1984254245A patent/PL145421B1/pl unknown
- 1984-05-17 PL PL1984247759A patent/PL144294B1/pl unknown
- 1984-05-17 PL PL1984254244A patent/PL145420B1/pl unknown
- 1984-07-16 AP APAP/P/1984/000003A patent/AP1A/en active
- 1984-10-17 US US06/661,674 patent/US4720587A/en not_active Expired - Fee Related
- 1984-10-17 US US06/661,803 patent/US4719236A/en not_active Expired - Fee Related
- 1984-10-17 US US06/661,802 patent/US4719049A/en not_active Expired - Fee Related
-
1985
- 1985-02-06 ES ES540161A patent/ES540161A0/es active Granted
- 1985-02-06 ES ES540160A patent/ES8604487A1/es not_active Expired
- 1985-04-22 US US06/725,157 patent/US4719047A/en not_active Expired - Fee Related
- 1985-08-30 SU SU853947162A patent/SU1466648A3/ru active
- 1985-12-02 SU SU853982431A patent/SU1447277A3/ru active
-
1987
- 1987-09-28 US US07/102,275 patent/US4820873A/en not_active Expired - Fee Related
-
1988
- 1988-03-11 AU AU13052/88A patent/AU599215B2/en not_active Ceased
-
1989
- 1989-04-08 SG SG223/89A patent/SG22389G/en unknown
- 1989-06-01 HK HK450/89A patent/HK45089A/en not_active IP Right Cessation
- 1989-12-08 CY CY1486A patent/CY1486A/xx unknown
-
1990
- 1990-06-01 JP JP2144246A patent/JPH0684336B2/ja not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2865925A (en) * | 1956-03-23 | 1958-12-23 | Sterling Drug Inc | Process for preparing n-(2-hydroxyethyl)-n-(lower-alkyl)-9-aminomethylanthracenes and intermediates therein |
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