CA1191090A - Composes antitumoraux - Google Patents

Composes antitumoraux

Info

Publication number: CA1191090A
Authority: CA; Canada
Prior art keywords: amsa; sterile; nicotinamide; solution; salt
Prior art date: 1980-06-12
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

CA000454877A

Other languages

English (en)

Inventor

Murray A. Kaplan

Edward C. Shinal

Alphonse P. Granatek

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.)

Bristol Myers Co

Original Assignee

Bristol Myers 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.)

1980-06-12

Filing date

1984-05-22

Publication date

1985-07-30

1981-05-22 Priority claimed from CA000378081A external-priority patent/CA1188223A/fr

1984-05-22 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1985-07-30 Application granted granted Critical

1985-07-30 Publication of CA1191090A publication Critical patent/CA1191090A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 91
230000000259 anti-tumor effect Effects 0.000 title description 4
XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims abstract description 137
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
239000007787 solid Substances 0.000 claims abstract description 7
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract description 6
ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims abstract description 4
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 44
239000002253 acid Substances 0.000 claims description 14
239000008135 aqueous vehicle Substances 0.000 claims description 7
238000002156 mixing Methods 0.000 claims description 4
238000001990 intravenous administration Methods 0.000 abstract description 9
206010028980 Neoplasm Diseases 0.000 abstract description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 140
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 89
229960003966 nicotinamide Drugs 0.000 description 70
239000011570 nicotinamide Substances 0.000 description 70
235000005152 nicotinamide Nutrition 0.000 description 70
150000003839 salts Chemical class 0.000 description 64
239000013078 crystal Substances 0.000 description 41
150000007524 organic acids Chemical class 0.000 description 41
238000003756 stirring Methods 0.000 description 39
230000000694 effects Effects 0.000 description 36
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 34
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 26
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 26
239000000706 filtrate Substances 0.000 description 25
239000011521 glass Substances 0.000 description 24
239000002585 base Substances 0.000 description 21
239000004615 ingredient Substances 0.000 description 20
238000002360 preparation method Methods 0.000 description 19
229960000448 lactic acid Drugs 0.000 description 17
229910001220 stainless steel Inorganic materials 0.000 description 17
239000010935 stainless steel Substances 0.000 description 17
239000008223 sterile water Substances 0.000 description 16
239000002552 dosage form Substances 0.000 description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
239000012453 solvate Substances 0.000 description 13
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 12
238000002425 crystallisation Methods 0.000 description 12
230000008025 crystallization Effects 0.000 description 12
235000012208 gluconic acid Nutrition 0.000 description 12
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 11
DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 11
239000000174 gluconic acid Substances 0.000 description 11
JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
229960004106 citric acid Drugs 0.000 description 7
229940113088 dimethylacetamide Drugs 0.000 description 7
239000004310 lactic acid Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 6
-1 gluconate m-AMSA salts Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 5
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
229940050410 gluconate Drugs 0.000 description 5
229960003681 gluconolactone Drugs 0.000 description 5
229940093915 gynecological organic acid Drugs 0.000 description 5
235000005985 organic acids Nutrition 0.000 description 5
238000011146 sterile filtration Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
235000012209 glucono delta-lactone Nutrition 0.000 description 4
235000014655 lactic acid Nutrition 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000008247 solid mixture Substances 0.000 description 4
JVTAAEKCZFNVCJ-REOHCLBHSA-M (S)-lactate Chemical compound C[C@H](O)C([O-])=O JVTAAEKCZFNVCJ-REOHCLBHSA-M 0.000 description 3
CIFNWWSBOFZXJI-UHFFFAOYSA-N 2-hydroxypropanoic acid;propan-2-one Chemical compound CC(C)=O.CC(O)C(O)=O CIFNWWSBOFZXJI-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229930195725 Mannitol Natural products 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229960004543 anhydrous citric acid Drugs 0.000 description 3
238000003556 assay Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
235000010355 mannitol Nutrition 0.000 description 3
239000000594 mannitol Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
230000003381 solubilizing effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000010268 HPLC based assay Methods 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical class [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229940001468 citrate Drugs 0.000 description 2
230000002301 combined effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
229940001447 lactate Drugs 0.000 description 2
150000003893 lactate salts Chemical class 0.000 description 2
229940058352 levulinate Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000006201 parenteral dosage form Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229940043131 pyroglutamate Drugs 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
238000003828 vacuum filtration Methods 0.000 description 2
MNKRTDOUBUSQHX-UHFFFAOYSA-N 2,4-dihydroxy-2-methyl-3-oxopentanoic acid Chemical compound CC(O)C(=O)C(C)(O)C(O)=O MNKRTDOUBUSQHX-UHFFFAOYSA-N 0.000 description 1
OZZQHCBFUVFZGT-UHFFFAOYSA-N 2-(2-hydroxypropanoyloxy)propanoic acid Chemical compound CC(O)C(=O)OC(C)C(O)=O OZZQHCBFUVFZGT-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
WWCDLXGTIXEJRY-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;propan-2-one Chemical compound CC(C)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O WWCDLXGTIXEJRY-UHFFFAOYSA-N 0.000 description 1
AURKDQJEOYBJSQ-UHFFFAOYSA-N 2-hydroxypropanoyl 2-hydroxypropanoate Chemical class CC(O)C(=O)OC(=O)C(C)O AURKDQJEOYBJSQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
150000001251 acridines Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000012296 anti-solvent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229960002303 citric acid monohydrate Drugs 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
QAUVAKQRNGDLCF-UHFFFAOYSA-N ethanol;pyridine-3-carboxamide Chemical compound CCO.NC(=O)C1=CC=CN=C1 QAUVAKQRNGDLCF-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229940025708 injectable product Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000006207 intravenous dosage form Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000012792 lyophilization process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
NYGZSXVEKMITFN-UHFFFAOYSA-N n-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 NYGZSXVEKMITFN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000454877A 1980-06-12 1984-05-22 Composes antitumoraux Expired CA1191090A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US15678880A	1980-06-12	1980-06-12
US156,788		1980-06-12
CA000378081A CA1188223A (fr)	1980-06-12	1981-05-22	Composes antitumoraux

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000378081A Division CA1188223A (fr)	1980-06-12	1981-05-22	Composes antitumoraux

Publications (1)

Publication Number	Publication Date
CA1191090A true CA1191090A (fr)	1985-07-30

Family

ID=25669330

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000454877A Expired CA1191090A (fr)	1980-06-12	1984-05-22	Composes antitumoraux

Country Status (1)

Country	Link
CA (1)	CA1191090A (fr)

1984
- 1984-05-22 CA CA000454877A patent/CA1191090A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-07-30	MKEX	Expiry

Publication	Publication Date	Title
AU663471B2 (en)	1995-10-12	Mometasone furoate monohydrate, process for making same and pharmaceutical compositions
CA1209571A (fr)	1986-08-12	Sels cristallins de bioxyde de benzothiozine
EP0067666B1 (fr)	1985-10-30	Sels de composés microbicides de naphtyridine et quinoléine et leur préparation
US4861786A (en)	1989-08-29	Composition for a stable vein compatible injectable solution of torasemide process for the preparation and method of use
CA1188223A (fr)	1985-06-04	Composes antitumoraux
CA1160571A (fr)	1984-01-17	Compose antitumoral
JPH0525857B2 (fr)	1993-04-14
CA1191090A (fr)	1985-07-30	Composes antitumoraux
US4335244A (en)	1982-06-15	Monolactate salts of 4'-(9-acridinylamino)methanesulfon-m-anisidide
PT85612B (pt)	1990-05-31	Processo para a preparacao de composicoes farmaceuticas liofilizadas contendo acidos fenilquinolinocarboxilicos
SU1122225A3 (ru)	1984-10-30	Способ получени кристаллической водорастворимой негигроскопичной этилендиаминовой,моноэтаноламиновой или диэтаноламиновой соли @ -(2-пиридил)-2-метил-4-окси-2 @ -1,2-бензтиазин-3-карбоксамид-1,1-диоксида
CA1252103A (fr)	1989-04-04	Sel de gluconate cristallin a base de 4- (9-acridinylamino-methanesulfo-m-anisidide)
EP0443471A1 (fr)	1991-08-28	2'-Déoxy-2'-méthylidènecytidine-dihydrate, méthodes pour sa production et composition
CA1159368A (fr)	1983-12-27	Compose antitumoral
US4575509A (en)	1986-03-11	Water-soluble formulations of m-AMSA with pyroglutamic acid
US5420124A (en)	1995-05-30	Stable, painless piroxicam potassium injectable composition
US4425348A (en)	1984-01-10	Antitumor compositions
US5034397A (en)	1991-07-23	Stable, water soluble salt compositions of M-AMSA in 1-methyl-2-pyrrolidinone
US6060498A (en)	2000-05-09	Composition containing antitumor agent
CA1159369A (fr)	1983-12-27	Mono dl-lactate hemiacetonate de 4-(9-acridinylamino) methanesulfo-m-anisidine, sous forme cristallisee
IE50512B1 (en)	1986-04-30	Pharmaceutical injectable composition and two-pack container for said composition
KR810002136B1 (ko)	1981-12-29	아목시실린 나트륨 함유 주사용 약제조성물의 제조방법
CA1197845A (fr)	1985-12-10	Sels bioxydes cristallins de benzothiazine
US4626541A (en)	1986-12-02	Water soluble salt composition of m-AMSA