CA1099213A - Agents antitumoraux - Google Patents

Agents antitumoraux

Info

Publication number: CA1099213A
Authority: CA; Canada
Prior art keywords: compositions; dosage unit; active ingredient; dosage; bis
Prior art date: 1978-01-30
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

Application number

CA308,224A

Other languages

English (en)

Inventor

Keith C. Murdock

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1978-01-30

Filing date

1978-07-26

Publication date

1981-04-14

1978-07-26 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-04-14 Application granted granted Critical

1981-04-14 Publication of CA1099213A publication Critical patent/CA1099213A/fr

Status Expired legal-status Critical Current

Links

239000002246 antineoplastic agent Substances 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 24
206010028980 Neoplasm Diseases 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 9
241000124008 Mammalia Species 0.000 claims abstract description 6
230000001939 inductive effect Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 18
230000037396 body weight Effects 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
239000004480 active ingredient Substances 0.000 abstract description 20
231100000252 nontoxic Toxicity 0.000 abstract description 6
230000003000 nontoxic effect Effects 0.000 abstract description 6
BDYRCLTVDLUGLN-UHFFFAOYSA-N 1,4-bis(3-aminopropylamino)-5,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCCN)=CC=C2NCCCN BDYRCLTVDLUGLN-UHFFFAOYSA-N 0.000 abstract description 4
208000032839 leukemia Diseases 0.000 abstract description 4
238000000034 method Methods 0.000 abstract description 3
230000004614 tumor growth Effects 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
229920002261 Corn starch Polymers 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
230000004083 survival effect Effects 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
-1 troches Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000167854 Bourreria succulenta Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000011149 active material Substances 0.000 description 3
235000019693 cherries Nutrition 0.000 description 3
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239000002612 dispersion medium Substances 0.000 description 3
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235000019359 magnesium stearate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
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229960001156 mitoxantrone Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
208000008342 Leukemia P388 Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
238000010521 absorption reaction Methods 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
229940121375 antifungal agent Drugs 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
239000002585 base Substances 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
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000036210 malignancy Effects 0.000 description 2
201000001441 melanoma Diseases 0.000 description 2
230000000684 melanotic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000013641 positive control Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
NDZUMKRLIPIEQP-UHFFFAOYSA-N 4,10-dihydroxyperylene-3,9-dione Chemical compound C1=CC2=C(C=CC3=O)C4C3=C(O)C=CC4C(C=CC3=O)=C2C3=C1O NDZUMKRLIPIEQP-UHFFFAOYSA-N 0.000 description 1
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 1
241000894006 Bacteria Species 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000233866 Fungi Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
241000238367 Mya arenaria Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229940046545 animal allergen extract Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
210000003567 ascitic fluid Anatomy 0.000 description 1
239000003855 balanced salt solution Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000006189 buccal tablet Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007958 cherry flavor Substances 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 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
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007951 isotonicity adjuster Substances 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
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
201000005296 lung carcinoma Diseases 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000001044 red dye Substances 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001179 sorption measurement Methods 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
238000001291 vacuum drying Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA308,224A 1978-01-30 1978-07-26 Agents antitumoraux Expired CA1099213A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US87304178A	1978-01-30	1978-01-30
US873,041		1978-01-30

Publications (1)

Publication Number	Publication Date
CA1099213A true CA1099213A (fr)	1981-04-14

Family

ID=25360874

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA308,224A Expired CA1099213A (fr)	1978-01-30	1978-07-26	Agents antitumoraux

Country Status (2)

Country	Link
CA (1)	CA1099213A (fr)
PH (1)	PH16830A (fr)

1978
- 1978-07-26 CA CA308,224A patent/CA1099213A/fr not_active Expired
- 1978-08-11 PH PH21483A patent/PH16830A/en unknown

Also Published As

Publication number	Publication date
PH16830A (en)	1984-03-06

Legal Events

Date	Code	Title	Description
1998-04-14	MKEX	Expiry

Publication	Publication Date	Title
US4197249A (en)	1980-04-08	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
CN101898995B (zh)	2013-05-01	卡维地洛磷酸盐和/或其溶剂合物相应的组合物和/或治疗方法
KR840001965B1 (ko)	1984-10-26	안트라센-9,10-비스-카르보닐-히드라존 유도체 제조방법
US4914105A (en)	1990-04-03	Anti-cancer compositions for delivering 5-fluorouracil
US4526989A (en)	1985-07-02	1,4-Bis (substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
CN117247319A (zh)	2023-12-19	一类5,6-二羟基萘甲酸酯化合物及其制备方法与用途
US4278689A (en)	1981-07-14	1,4-Bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
CA1099213A (fr)	1981-04-14	Agents antitumoraux
JPS5916869A (ja)	1984-01-28	新規なｏ−フエニレンジアミン誘導体
US4820738A (en)	1989-04-11	1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
US4456552A (en)	1984-06-26	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4418078A (en)	1983-11-29	Method of treating tumors in warm-blooded animals
US4540519A (en)	1985-09-10	1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4275009A (en)	1981-06-23	1-(Aminoalkylamino)-5,8-dihydroxy-4-substituted-anthraquinones
US4614618A (en)	1986-09-30	1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof
SE436208B (sv)	1984-11-19	Sett att framstella 5-fluoro-uracilderivat
US4430501A (en)	1984-02-07	1,4-Bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
US3463861A (en)	1969-08-26	Compositions and method of treating mycobacterium tuberculosis with 2,2'-(ethylenediimino)-di-1-butanols
EP0131787A2 (fr)	1985-01-23	Bases de Schiff d'(aminoalkyle ou aminoalkyle substitué)-amino-9,10-anthracènediones
JP2511709B2 (ja)	1996-07-03	キサントシリンｘモノメチルエ―テル誘導体及びそれを含有する抗腫瘍剤
JPH06501032A (ja)	1994-01-27	薬剤組成物
US4600573A (en)	1986-07-15	Compositions and method for alleviating the toxic effects of 1,3-bis(2-chloroethyl)-1-nitrosourea
GB2036554A (en)	1980-07-02	Anthraquinones for use in therapy
CA1116522A (fr)	1982-01-19	Agents antitumoraux
JPS59222417A (ja)	1984-12-14	Ｎ，Ｎ−ジエチル−５−メチル−２Ｈ−１−ベンゾチオピラノ−〔４，３，２−ｃｄ〕−インダゾ−ル−２−エタナミン組成物