JPH051261B2 - - Google Patents
Info
- Publication number
- JPH051261B2 JPH051261B2 JP58013845A JP1384583A JPH051261B2 JP H051261 B2 JPH051261 B2 JP H051261B2 JP 58013845 A JP58013845 A JP 58013845A JP 1384583 A JP1384583 A JP 1384583A JP H051261 B2 JPH051261 B2 JP H051261B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- bis
- amino
- oxazolidinyl
- dihydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 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 claims description 15
- 150000004056 anthraquinones Chemical class 0.000 claims description 15
- -1 chloro, bromo, hydroxy, methoxy, methyl Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000012458 free base Substances 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 229960001156 mitoxantrone Drugs 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 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 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- RXIXODXUQIYSFA-UHFFFAOYSA-N 1,4-bis[2-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound CC1(C)OCCN1CCNC(C=1C(=O)C2=C(O)C=CC(O)=C2C(=O)C=11)=CC=C1NCCN1C(C)(C)OCC1 RXIXODXUQIYSFA-UHFFFAOYSA-N 0.000 claims description 2
- NIUBFFGJJMKEKR-UHFFFAOYSA-N 1,4-bis[2-[2-(2,4-dimethoxyphenyl)-1,3-oxazolidin-3-yl]ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound COC1=CC(OC)=CC=C1C1N(CCNC=2C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(NCCN3C(OCC3)C=3C(=CC(OC)=CC=3)OC)=CC=2)CCO1 NIUBFFGJJMKEKR-UHFFFAOYSA-N 0.000 claims description 2
- ZABQAUMIWIZBBF-UHFFFAOYSA-N 1,4-bis[2-[2-(furan-2-yl)-1,3-oxazolidin-3-yl]ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2OC=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=CO1 ZABQAUMIWIZBBF-UHFFFAOYSA-N 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- UEPWPXZQOFBKBF-UHFFFAOYSA-N 1,4-bis[2-(2-hexyl-1,3-oxazolidin-3-yl)ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound CCCCCCC1OCCN1CCNC(C=1C(=O)C2=C(O)C=CC(O)=C2C(=O)C=11)=CC=C1NCCN1C(CCCCCC)OCC1 UEPWPXZQOFBKBF-UHFFFAOYSA-N 0.000 claims 1
- KCUBCPHHRKZNAA-UHFFFAOYSA-N 1,4-bis[2-[2-(2,6-dichlorophenyl)-1,3-oxazolidin-3-yl]ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2C(=CC=CC=2Cl)Cl)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=C(Cl)C=CC=C1Cl KCUBCPHHRKZNAA-UHFFFAOYSA-N 0.000 claims 1
- GXVFBQXSHCTAOJ-UHFFFAOYSA-N 1,4-bis[2-[2-(3,5-dimethoxyphenyl)-1,3-oxazolidin-3-yl]ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound COC1=CC(OC)=CC(C2N(CCO2)CCNC=2C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(NCCN3C(OCC3)C=3C=C(OC)C=C(OC)C=3)=CC=2)=C1 GXVFBQXSHCTAOJ-UHFFFAOYSA-N 0.000 claims 1
- PGPPPRKYLUQKJZ-UHFFFAOYSA-N 1,4-bis[2-[2-(4-fluorophenyl)-1,3-oxazolidin-3-yl]ethylamino]-5,8-dihydroxyanthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2C=CC(F)=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=C(F)C=C1 PGPPPRKYLUQKJZ-UHFFFAOYSA-N 0.000 claims 1
- FKAVWEPRJBEKDY-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C3(CCCCC3)OCC2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC11CCCCC1 FKAVWEPRJBEKDY-UHFFFAOYSA-N 0.000 claims 1
- MPNDQVNJQHTJIB-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-methyl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound CC1OCCN1CCNC(C=1C(=O)C2=C(O)C=CC(O)=C2C(=O)C=11)=CC=C1NCCN1C(C)OCC1 MPNDQVNJQHTJIB-UHFFFAOYSA-N 0.000 claims 1
- RVXCRERORGPIJA-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-naphthalen-1-yl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC=C2C(C3OCCN3CCNC=3C=CC(NCCN4C(OCC4)C=4C5=CC=CC=C5C=CC=4)=C4C(=O)C=5C(O)=CC=C(C=5C(=O)C4=3)O)=CC=CC2=C1 RVXCRERORGPIJA-UHFFFAOYSA-N 0.000 claims 1
- XNTCPCSCPGPAMX-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-pyridin-2-yl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2N=CC=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=CC=N1 XNTCPCSCPGPAMX-UHFFFAOYSA-N 0.000 claims 1
- JHTBDCWSMNGJGS-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-pyridin-3-yl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2C=NC=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=CN=C1 JHTBDCWSMNGJGS-UHFFFAOYSA-N 0.000 claims 1
- TXGICSUEPVGSRV-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-pyridin-4-yl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2C=CN=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=NC=C1 TXGICSUEPVGSRV-UHFFFAOYSA-N 0.000 claims 1
- JCEAGMJRNIPJAI-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-(2-thiophen-2-yl-1,3-oxazolidin-3-yl)ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2SC=CC=2)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=CS1 JCEAGMJRNIPJAI-UHFFFAOYSA-N 0.000 claims 1
- SYSBKPCZJGBCCE-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-[2-(2-hydroxy-4-methoxyphenyl)-1,3-oxazolidin-3-yl]ethylamino]anthracene-9,10-dione Chemical compound OC1=CC(OC)=CC=C1C1N(CCNC=2C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(NCCN3C(OCC3)C=3C(=CC(OC)=CC=3)O)=CC=2)CCO1 SYSBKPCZJGBCCE-UHFFFAOYSA-N 0.000 claims 1
- LKMWVBKFEYMQPN-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-[2-(4-methoxyphenyl)-1,3-oxazolidin-3-yl]ethylamino]anthracene-9,10-dione Chemical compound C1=CC(OC)=CC=C1C1N(CCNC=2C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(NCCN3C(OCC3)C=3C=CC(OC)=CC=3)=CC=2)CCO1 LKMWVBKFEYMQPN-UHFFFAOYSA-N 0.000 claims 1
- YVMFOVJAMWWOKM-UHFFFAOYSA-N 1,4-dihydroxy-5,8-bis[2-[2-[3-(trifluoromethyl)phenyl]-1,3-oxazolidin-3-yl]ethylamino]anthracene-9,10-dione Chemical compound C1=CC(NCCN2C(OCC2)C=2C=C(C=CC=2)C(F)(F)F)=C2C(=O)C=3C(O)=CC=C(O)C=3C(=O)C2=C1NCCN1CCOC1C1=CC=CC(C(F)(F)F)=C1 YVMFOVJAMWWOKM-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 241001465754 Metazoa Species 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000004083 survival effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000013641 positive control Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 7
- 208000003747 lymphoid leukemia Diseases 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 201000001441 melanoma Diseases 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229960002949 fluorouracil Drugs 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003855 balanced salt solution Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 239000007928 intraperitoneal injection Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 238000011765 DBA/2 mouse Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003070 absorption delaying agent Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 210000003567 ascitic fluid Anatomy 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
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- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
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- 230000001580 bacterial effect Effects 0.000 description 1
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- 239000003899 bactericide agent Substances 0.000 description 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 229960004926 chlorobutanol Drugs 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZUKSLMGYYPZZJD-UHFFFAOYSA-N ethenimine Chemical group C=C=N ZUKSLMGYYPZZJD-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
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- 201000005787 hematologic cancer Diseases 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
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- 230000000684 melanotic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US345671 | 1982-02-04 | ||
| US345700 | 1982-02-04 | ||
| US06/345,671 US4375469A (en) | 1982-02-04 | 1982-02-04 | Oxaza heterocycle-anthraquinones, pharmaceutical compositions thereof and method of use thereof |
| US383363 | 1982-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58134083A JPS58134083A (ja) | 1983-08-10 |
| JPH051261B2 true JPH051261B2 (https=) | 1993-01-07 |
Family
ID=23355996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58013845A Granted JPS58134083A (ja) | 1982-02-04 | 1983-02-01 | 新規１，４−ビス（置換アミノ）−５，８−ジヒドロキシアントラキノン類、その製造法およびそれを含有する薬剤 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4375469A (https=) |
| JP (1) | JPS58134083A (https=) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3646072A (en) * | 1970-07-27 | 1972-02-29 | Du Pont | Turquoise biscationic anthraquinone dyes |
| US4197249A (en) * | 1977-08-15 | 1980-04-08 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
-
1982
- 1982-02-04 US US06/345,671 patent/US4375469A/en not_active Expired - Lifetime
-
1983
- 1983-02-01 JP JP58013845A patent/JPS58134083A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4375469A (en) | 1983-03-01 |
| JPS58134083A (ja) | 1983-08-10 |
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