CH644840A5 - Basisch substituierte anthrachinone und dihydroanthrachinone, ihre herstellung und pharmazeutische zubereitungen. - Google Patents
Basisch substituierte anthrachinone und dihydroanthrachinone, ihre herstellung und pharmazeutische zubereitungen. Download PDFInfo
- Publication number
- CH644840A5 CH644840A5 CH862778A CH862778A CH644840A5 CH 644840 A5 CH644840 A5 CH 644840A5 CH 862778 A CH862778 A CH 862778A CH 862778 A CH862778 A CH 862778A CH 644840 A5 CH644840 A5 CH 644840A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- hydrogen
- formula
- carbon atoms
- bis
- Prior art date
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 10
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 74
- -1 morpholino, thiomorpholino, piperazino Chemical group 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 229960001156 mitoxantrone Drugs 0.000 claims description 49
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- BWFLZLUYYWVXHY-UHFFFAOYSA-N 5-(2-aminoethylamino)-1,4-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C=CC=C2NCCN BWFLZLUYYWVXHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- OYELEBBISJGNHJ-UHFFFAOYSA-N 1,3-oxazinan-2-one Chemical compound O=C1NCCCO1 OYELEBBISJGNHJ-UHFFFAOYSA-N 0.000 claims 1
- CLVFWRBVFBUDQU-UHFFFAOYSA-N 1,4-bis(2-aminoethylamino)-5,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN CLVFWRBVFBUDQU-UHFFFAOYSA-N 0.000 claims 1
- FJSGMFGNISZAGK-UHFFFAOYSA-N 5,8-bis[2-(dimethylamino)ethylamino]-1,2-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C(O)=CC=C2C(=O)C2=C1C(NCCN(C)C)=CC=C2NCCN(C)C FJSGMFGNISZAGK-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 126
- 239000000047 product Substances 0.000 description 73
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 72
- 239000007787 solid Substances 0.000 description 72
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 70
- 229960002949 fluorouracil Drugs 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 238000003756 stirring Methods 0.000 description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000004056 anthraquinones Chemical class 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 230000004083 survival effect Effects 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000003826 tablet Substances 0.000 description 19
- 206010028980 Neoplasm Diseases 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 14
- 229920002261 Corn starch Polymers 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000008120 corn starch Substances 0.000 description 14
- 229940099112 cornstarch Drugs 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 14
- QJQPINQAQJTYMH-UHFFFAOYSA-N 5,8,9,10-tetrahydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound O=C1CCC(=O)C2=C1C(O)=C1C(O)=CC=C(O)C1=C2O QJQPINQAQJTYMH-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 239000004519 grease Substances 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- FVXPBEUYCCZFJT-UHFFFAOYSA-N 9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound C1=CC=C2C(O)=C(C(=O)CCC3=O)C3=C(O)C2=C1 FVXPBEUYCCZFJT-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 210000004698 lymphocyte Anatomy 0.000 description 6
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- 239000008215 water for injection Substances 0.000 description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- OXWAFRBPEMIBOA-UHFFFAOYSA-N 5-(3-aminopropylamino)-1,4-dihydroxyanthracene-9,10-dione Chemical compound NCCCNC1=CC=CC=2C(C3=C(C=CC(=C3C(C12)=O)O)O)=O OXWAFRBPEMIBOA-UHFFFAOYSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
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- 239000004299 sodium benzoate Substances 0.000 description 5
- 235000010234 sodium benzoate Nutrition 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 208000008342 Leukemia P388 Diseases 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 4
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 4
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- 238000004809 thin layer chromatography Methods 0.000 description 4
- XXOFSLDVRYQVSV-UHFFFAOYSA-N 1,4-bis(2-aminoethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN XXOFSLDVRYQVSV-UHFFFAOYSA-N 0.000 description 3
- VYVJXUYUIRSTAJ-UHFFFAOYSA-N 1,4-bis[2-(dimethylamino)ethylamino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCN(C)C)=CC=C2NCCN(C)C VYVJXUYUIRSTAJ-UHFFFAOYSA-N 0.000 description 3
- UXFYNFPNBZUUIB-UHFFFAOYSA-N 1-(2-aminoethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCCN UXFYNFPNBZUUIB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
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- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- C08G59/623—Aminophenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Pathology (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82487277A | 1977-08-15 | 1977-08-15 | |
| US87304078A | 1978-01-30 | 1978-01-30 | |
| US87304178A | 1978-01-30 | 1978-01-30 | |
| US87317478A | 1978-01-30 | 1978-01-30 | |
| US05/903,292 US4138415A (en) | 1978-05-05 | 1978-05-05 | 1,4-Bis(aminoalkylamino)-anthraquinones and leuco derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH644840A5 true CH644840A5 (de) | 1984-08-31 |
Family
ID=27542240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH862778A CH644840A5 (de) | 1977-08-15 | 1978-08-14 | Basisch substituierte anthrachinone und dihydroanthrachinone, ihre herstellung und pharmazeutische zubereitungen. |
Country Status (22)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275009A (en) * | 1979-05-29 | 1981-06-23 | American Cyanamid Company | 1-(Aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones |
| US4275010A (en) * | 1979-10-24 | 1981-06-23 | American Cyanamid Company | 5,8-Dihydroxy-1,4-bis(guanidinylamino)anthraquinones |
| US4296030A (en) * | 1980-04-09 | 1981-10-20 | American Cyanamid Company | Metal chelates of 1,4-bis(substituted-amino-5,8-dihydroxy-anthraquinones |
| US4278605A (en) * | 1980-06-30 | 1981-07-14 | American Cyanamid Company | Heteroalkylenebisanthraquinones |
| EP0052853A1 (de) * | 1980-11-24 | 1982-06-02 | Hoechst Aktiengesellschaft | Bis-Aminomethyl-anthrachinon-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung |
| EP0083683A1 (en) * | 1981-10-26 | 1983-07-20 | American Cyanamid Company | Method of preparing 1,4-bis(substituted-amino)-5,8-dihydroxyanthraquinones and pharmaceutical compositions containing them |
| ATE48942T1 (de) * | 1984-02-27 | 1990-01-15 | American Cyanamid Co | Verwendung von 1,4 bisubstituierten anthrachinonen zur herstellung von immunsuppressiva. |
| EP0182135A3 (en) * | 1984-11-19 | 1987-08-05 | American Cyanamid Company | Novel bis-(substituted amino) anthraquinones |
| US5436243A (en) * | 1993-11-17 | 1995-07-25 | Research Triangle Institute Duke University | Aminoanthraquinone derivatives to combat multidrug resistance |
| GB9815910D0 (en) | 1998-07-21 | 1998-09-23 | Btg Int Ltd | Synthetic method |
| CA2550839A1 (en) * | 2003-12-23 | 2005-07-07 | Somanta Limited | Antharquinone compounds as anti cancer compounds |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| JP6104504B2 (ja) | 2008-12-23 | 2017-03-29 | ギリアド ファーマセット エルエルシー | ヌクレオシド類似体 |
| CL2009002206A1 (es) | 2008-12-23 | 2011-08-26 | Gilead Pharmasset Llc | Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales. |
| CN102695513A (zh) | 2008-12-23 | 2012-09-26 | 吉利德制药有限责任公司 | 核苷氨基磷酸酯 |
| PT2752422T (pt) | 2010-03-31 | 2017-11-07 | Gilead Pharmasset Llc | Síntese estereosseletiva de princípios ativos contendo fósforo |
| DE102012203981A1 (de) * | 2012-03-14 | 2013-09-19 | Henkel Ag & Co. Kgaa | Mittel zum Färben und/oder Mattieren von keratinhaltigen Fasern enthaltend neuartige1,4-Diaminoanthrachinonfarbstoffe |
| GB201214169D0 (en) | 2012-08-08 | 2012-09-19 | Biostatus Ltd | New compounds and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1422016A (fr) * | 1962-10-29 | 1965-12-24 | Oreal | Nouveaux colorants anthraquinoniques et leur application à la teinture des cheveux |
| GB1157506A (en) * | 1965-09-10 | 1969-07-09 | Ilford Ltd | Anthraquinone Dye Colour Couplers and their use in Colour Photographic Materials |
| US3646072A (en) * | 1970-07-27 | 1972-02-29 | Du Pont | Turquoise biscationic anthraquinone dyes |
| US3700398A (en) * | 1970-07-27 | 1972-10-24 | Du Pont | Process for dyeing acid-modified nylon fibers |
| US4051155A (en) * | 1975-12-15 | 1977-09-27 | Allied Chemical Corporation | Anthraquinone dyes |
-
1978
- 1978-07-19 SE SE7807987A patent/SE445996B/sv not_active IP Right Cessation
- 1978-07-26 IL IL55218A patent/IL55218A/xx active IP Right Grant
- 1978-07-27 NZ NZ187989A patent/NZ187989A/xx unknown
- 1978-08-03 AR AR273195A patent/AR225884A1/es active
- 1978-08-07 GR GR56957A patent/GR74415B/el unknown
- 1978-08-09 AU AU38776/78A patent/AU527103B2/en not_active Expired
- 1978-08-09 FR FR7823503A patent/FR2400504A1/fr active Granted
- 1978-08-11 BE BE78189842A patent/BE869688A/xx not_active IP Right Cessation
- 1978-08-11 IE IE1636/78A patent/IE47253B1/en not_active IP Right Cessation
- 1978-08-14 DE DE19782835661 patent/DE2835661A1/de active Granted
- 1978-08-14 AT AT590678A patent/AT359484B/de not_active IP Right Cessation
- 1978-08-14 PT PT68420A patent/PT68420A/pt unknown
- 1978-08-14 CH CH862778A patent/CH644840A5/de not_active IP Right Cessation
- 1978-08-14 DK DK358678A patent/DK158836C/da not_active IP Right Cessation
- 1978-08-14 NO NO782756A patent/NO148777C/no unknown
- 1978-08-14 IT IT50730/78A patent/IT1107773B/it active
- 1978-08-15 FI FI782481A patent/FI70882C/fi not_active IP Right Cessation
- 1978-08-15 GB GB7833365A patent/GB2004293B/en not_active Expired
- 1978-08-15 PL PL1978209065A patent/PL122586B1/pl unknown
- 1978-08-15 DD DD78207292A patent/DD139256A5/xx unknown
- 1978-08-15 NL NLAANVRAGE7808475,A patent/NL188981C/xx not_active IP Right Cessation
-
1982
- 1982-02-01 NO NO820290A patent/NO150482C/no unknown
-
1987
- 1987-12-16 JP JP62316353A patent/JPS6463556A/ja active Granted
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCF | Supplementary protection certificate filed |
Free format text: IKS 46574/850816, 960229 |
|
| SPCG | Supplementary protection certificate granted |
Free format text: IKS 46574/850816, 960229, EXPIRES:20000816 |
|
| PL | Patent ceased |