NL8006440A - Verbindingen en preparaten met anti-tumorwerking; werkwijze voor het bereiden daarvan. - Google Patents
Verbindingen en preparaten met anti-tumorwerking; werkwijze voor het bereiden daarvan. Download PDFInfo
- Publication number
- NL8006440A NL8006440A NL8006440A NL8006440A NL8006440A NL 8006440 A NL8006440 A NL 8006440A NL 8006440 A NL8006440 A NL 8006440A NL 8006440 A NL8006440 A NL 8006440A NL 8006440 A NL8006440 A NL 8006440A
- Authority
- NL
- Netherlands
- Prior art keywords
- amsa
- crystalline
- acetone
- solution
- msa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 14
- 230000000259 anti-tumor effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 title description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 114
- 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 description 79
- 239000000243 solution Substances 0.000 claims description 64
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- CIFNWWSBOFZXJI-UHFFFAOYSA-N 2-hydroxypropanoic acid;propan-2-one Chemical compound CC(C)=O.CC(O)C(O)=O CIFNWWSBOFZXJI-UHFFFAOYSA-N 0.000 claims description 23
- 239000002552 dosage form Substances 0.000 claims description 15
- 150000003893 lactate salts Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 8
- 239000004310 lactic acid Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 7
- 235000014655 lactic acid Nutrition 0.000 claims description 7
- JVTAAEKCZFNVCJ-REOHCLBHSA-M (S)-lactate Chemical compound C[C@H](O)C([O-])=O JVTAAEKCZFNVCJ-REOHCLBHSA-M 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims description 4
- 239000008135 aqueous vehicle Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 35
- 239000013078 crystal Substances 0.000 description 32
- 229960000448 lactic acid Drugs 0.000 description 17
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 14
- 239000011521 glass Substances 0.000 description 12
- 238000001990 intravenous administration Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 8
- 239000008223 sterile water Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- 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 3
- -1 9-acridinylamino Chemical group 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940113088 dimethylacetamide Drugs 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229940028564 potassium bromide pill Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000006207 intravenous dosage form Substances 0.000 description 2
- 239000006201 parenteral dosage form Substances 0.000 description 2
- 238000011146 sterile filtration Methods 0.000 description 2
- 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
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XYJQBHCHAZPWHA-UHFFFAOYSA-N CC(C)C([CH2-])=O Chemical compound CC(C)C([CH2-])=O XYJQBHCHAZPWHA-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940025708 injectable product Drugs 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-UHFFFAOYSA-N lactitol Chemical compound OCC(O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O VQHSOMBJVWLPSR-UHFFFAOYSA-N 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9916379A | 1979-11-30 | 1979-11-30 | |
| US9916379 | 1979-11-30 | ||
| US06/150,401 US4335244A (en) | 1979-11-30 | 1980-05-23 | Monolactate salts of 4'-(9-acridinylamino)methanesulfon-m-anisidide |
| US15040180 | 1980-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8006440A true NL8006440A (nl) | 1981-07-01 |
Family
ID=26795677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006440A NL8006440A (nl) | 1979-11-30 | 1980-11-26 | Verbindingen en preparaten met anti-tumorwerking; werkwijze voor het bereiden daarvan. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4335244A (fr) |
| AT (1) | AT380473B (fr) |
| AU (1) | AU533846B2 (fr) |
| CA (1) | CA1158650A (fr) |
| CH (1) | CH648302A5 (fr) |
| DE (1) | DE3044736A1 (fr) |
| DK (1) | DK509780A (fr) |
| FI (1) | FI80023C (fr) |
| FR (1) | FR2470765A1 (fr) |
| GB (1) | GB2064534B (fr) |
| GR (1) | GR71926B (fr) |
| IE (1) | IE50445B1 (fr) |
| IT (1) | IT1143199B (fr) |
| LU (1) | LU82965A1 (fr) |
| NL (1) | NL8006440A (fr) |
| NZ (1) | NZ195343A (fr) |
| SE (1) | SE457257B (fr) |
| YU (1) | YU42986B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4399283A (en) * | 1980-03-11 | 1983-08-16 | Warner Lambert Company | Pharmaceutical salts of 4'-(9-acridinylamino)-methanesulfon-m-anisidide |
| HU186383B (en) * | 1981-02-27 | 1985-07-29 | Biogal Gyogyszergyar | Process for producing new citostatic amni-acridie-alpha, beta-bracket-d-bracket closed, or aracket-l-bracket closed-n-glycoside derivatives and salts |
| US4575509A (en) * | 1983-01-31 | 1986-03-11 | Bristol-Myers Company | Water-soluble formulations of m-AMSA with pyroglutamic acid |
| US4626541A (en) * | 1985-09-12 | 1986-12-02 | Bristol-Myers Company | Water soluble salt composition of m-AMSA |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3332991A (en) * | 1965-03-22 | 1967-07-25 | Lilly Co Eli | Soluble salts of heterocyclic iodinecontaining bactericides |
| PL106752B1 (pl) * | 1976-02-25 | 1980-01-31 | Politechnika Gdanska | Sposob otrzymywania nowych 1-nitro-9-alkiloaminoalkiloaminoakrydyn lub ich soli |
| PL101032B1 (pl) * | 1976-04-06 | 1978-11-30 | Sposob otrzymywania 1-nitro-9-dwualkilo-aminoizoalkiloamiroakrydyn lub ich soli |
-
1980
- 1980-05-23 US US06/150,401 patent/US4335244A/en not_active Expired - Lifetime
- 1980-10-22 NZ NZ195343A patent/NZ195343A/xx unknown
- 1980-10-22 AU AU63604/80A patent/AU533846B2/en not_active Ceased
- 1980-10-27 CA CA000363356A patent/CA1158650A/fr not_active Expired
- 1980-10-27 YU YU2742/80A patent/YU42986B/xx unknown
- 1980-11-05 GR GR63290A patent/GR71926B/el unknown
- 1980-11-25 FR FR8024990A patent/FR2470765A1/fr active Granted
- 1980-11-26 FI FI803674A patent/FI80023C/fi not_active IP Right Cessation
- 1980-11-26 NL NL8006440A patent/NL8006440A/nl not_active Application Discontinuation
- 1980-11-27 AT AT0580480A patent/AT380473B/de not_active IP Right Cessation
- 1980-11-27 IT IT50258/80A patent/IT1143199B/it active
- 1980-11-27 DE DE19803044736 patent/DE3044736A1/de active Granted
- 1980-11-28 IE IE2475/80A patent/IE50445B1/en unknown
- 1980-11-28 SE SE8008399A patent/SE457257B/sv not_active IP Right Cessation
- 1980-11-28 CH CH8861/80A patent/CH648302A5/fr not_active IP Right Cessation
- 1980-11-28 DK DK509780A patent/DK509780A/da not_active Application Discontinuation
- 1980-11-28 GB GB8038277A patent/GB2064534B/en not_active Expired
- 1980-11-28 LU LU82965A patent/LU82965A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR71926B (fr) | 1983-08-18 |
| DE3044736C2 (fr) | 1989-08-17 |
| IE50445B1 (en) | 1986-04-16 |
| AU6360480A (en) | 1981-06-04 |
| DE3044736A1 (de) | 1981-08-27 |
| GB2064534A (en) | 1981-06-17 |
| SE457257B (sv) | 1988-12-12 |
| FR2470765B1 (fr) | 1983-12-30 |
| AU533846B2 (en) | 1983-12-15 |
| DK509780A (da) | 1981-05-31 |
| YU274280A (en) | 1984-02-29 |
| FI80023C (fi) | 1990-04-10 |
| IT1143199B (it) | 1986-10-22 |
| YU42986B (en) | 1989-02-28 |
| FR2470765A1 (fr) | 1981-06-12 |
| IE802475L (en) | 1981-05-30 |
| FI803674L (fi) | 1981-05-31 |
| LU82965A1 (fr) | 1981-06-04 |
| CH648302A5 (fr) | 1985-03-15 |
| AT380473B (de) | 1986-05-26 |
| ATA580480A (de) | 1985-10-15 |
| FI80023B (fi) | 1989-12-29 |
| SE8008399L (sv) | 1981-05-31 |
| CA1158650A (fr) | 1983-12-13 |
| IT8050258A0 (it) | 1980-11-27 |
| US4335244A (en) | 1982-06-15 |
| GB2064534B (en) | 1983-09-28 |
| NZ195343A (en) | 1983-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: BRISTOL-MYERS SQUIBB COMPANY |
|
| BV | The patent application has lapsed |