JP2010006831A5 - - Google Patents
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- Publication number
- JP2010006831A5 JP2010006831A5 JP2009197462A JP2009197462A JP2010006831A5 JP 2010006831 A5 JP2010006831 A5 JP 2010006831A5 JP 2009197462 A JP2009197462 A JP 2009197462A JP 2009197462 A JP2009197462 A JP 2009197462A JP 2010006831 A5 JP2010006831 A5 JP 2010006831A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- aliphatic
- tricarboxylic
- pentenoic
- 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.)
- Pending
Links
- -1 carboxylate anion Chemical class 0.000 claims 56
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 21
- 125000001931 aliphatic group Chemical group 0.000 claims 20
- 238000000034 method Methods 0.000 claims 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 18
- 229930194542 Keto Natural products 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000000468 ketone group Chemical group 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 15
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 claims 12
- CQJHAULYLJXJNL-UHFFFAOYSA-N 4-methylpent-3-enoic acid Chemical compound CC(C)=CCC(O)=O CQJHAULYLJXJNL-UHFFFAOYSA-N 0.000 claims 12
- 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 claims 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 12
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 7
- 235000011054 acetic acid Nutrition 0.000 claims 7
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 7
- 239000001630 malic acid Substances 0.000 claims 7
- 235000011090 malic acid Nutrition 0.000 claims 7
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 6
- JNZBHHQBPHSOMU-WNQIDUERSA-N 5-amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NC1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=CC3=C1 JNZBHHQBPHSOMU-WNQIDUERSA-N 0.000 claims 6
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 6
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 6
- 239000001361 adipic acid Substances 0.000 claims 6
- 235000011037 adipic acid Nutrition 0.000 claims 6
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 6
- 235000015165 citric acid Nutrition 0.000 claims 6
- 235000019253 formic acid Nutrition 0.000 claims 6
- 239000001530 fumaric acid Substances 0.000 claims 6
- 235000011087 fumaric acid Nutrition 0.000 claims 6
- 239000000174 gluconic acid Substances 0.000 claims 6
- 235000012208 gluconic acid Nutrition 0.000 claims 6
- 239000004310 lactic acid Substances 0.000 claims 6
- 235000014655 lactic acid Nutrition 0.000 claims 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 6
- 239000011976 maleic acid Substances 0.000 claims 6
- 229960002510 mandelic acid Drugs 0.000 claims 6
- 235000019260 propionic acid Nutrition 0.000 claims 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 6
- 239000011975 tartaric acid Substances 0.000 claims 6
- 235000002906 tartaric acid Nutrition 0.000 claims 6
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims 6
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims 6
- XXVLKDRPHSFIIB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=CC3=C1 XXVLKDRPHSFIIB-UHFFFAOYSA-N 0.000 claims 5
- 229950001745 mitonafide Drugs 0.000 claims 5
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 claims 5
- 239000007858 starting material Substances 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
- 235000003704 aspartic acid Nutrition 0.000 claims 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 4
- 235000013922 glutamic acid Nutrition 0.000 claims 4
- 239000004220 glutamic acid Substances 0.000 claims 4
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 3
- UPALIKSFLSVKIS-UHFFFAOYSA-N 5-amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione Chemical compound NC1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=CC3=C1 UPALIKSFLSVKIS-UHFFFAOYSA-N 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 229960004701 amonafide Drugs 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 150000007942 carboxylates Chemical class 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- BJEPYKJPYRNKOW-UWTATZPHSA-M malate ion Chemical compound [O-]C(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-M 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 claims 2
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 2
- 229940009098 aspartate Drugs 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- 229940049906 glutamate Drugs 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 229940076788 pyruvate Drugs 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 229940107700 pyruvic acid Drugs 0.000 claims 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/128,129 US6693198B2 (en) | 2002-04-22 | 2002-04-22 | Amonafide salts |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002197809A Division JP4630518B2 (ja) | 2002-04-22 | 2002-07-05 | アモナフィド塩 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010006831A JP2010006831A (ja) | 2010-01-14 |
| JP2010006831A5 true JP2010006831A5 (enExample) | 2010-10-21 |
Family
ID=29248438
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002197809A Expired - Fee Related JP4630518B2 (ja) | 2002-04-22 | 2002-07-05 | アモナフィド塩 |
| JP2009197462A Pending JP2010006831A (ja) | 2002-04-22 | 2009-08-27 | アモナフィド塩 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002197809A Expired - Fee Related JP4630518B2 (ja) | 2002-04-22 | 2002-07-05 | アモナフィド塩 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6693198B2 (enExample) |
| EP (1) | EP1499595B1 (enExample) |
| JP (2) | JP4630518B2 (enExample) |
| AT (1) | ATE359273T1 (enExample) |
| AU (1) | AU2003221771B2 (enExample) |
| CA (1) | CA2482445A1 (enExample) |
| DE (1) | DE60313156T2 (enExample) |
| ES (1) | ES2287463T3 (enExample) |
| WO (1) | WO2003089415A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050239816A1 (en) * | 2002-04-22 | 2005-10-27 | Xanthus Life Sciences, Inc. | Amonafide salts |
| US6693198B2 (en) | 2002-04-22 | 2004-02-17 | Xanthus Life Sciences, Inc. | Amonafide salts |
| WO2004004716A1 (en) * | 2002-07-08 | 2004-01-15 | Chemgenex Pharmaceuticals Limited | Naphthalimide synthesis including amonafide synthesis and pharmaceutical preparations thereof |
| AU2005209845A1 (en) * | 2004-01-30 | 2005-08-18 | Chemgenex Pharmaceuticals, Inc. | Naphthalimide dosing by N-acetyl transferase genotyping |
| BRPI0510719A (pt) * | 2004-05-05 | 2007-11-20 | Unibioscreen Sa | derivados de naftalimida, composição farmacêutica, uso e método de preparação dos mesmos |
| AU2005249593A1 (en) * | 2004-06-04 | 2005-12-15 | Chemgenex Pharmaceuticals Inc. | Methods of treating cellular proliferative disease using naphthalimide and PARP-1 inhibitors |
| FR2898902B1 (fr) * | 2006-03-24 | 2010-09-10 | Oreal | Colorants particuliers de type naphtalimide, composition tinctoriale comprenant au moins un tel colorant, procede de mise en oeuvre et utilisations |
| ES2338193B8 (es) * | 2008-02-25 | 2011-07-19 | Centro Atlantico Del Medicamento, S.A. | Nuevas sales de amonafide. |
| EA038195B1 (ru) | 2009-01-16 | 2021-07-22 | Экселиксис, Инк. | Малатная соль n-(4-{[6,7-бис-(метилокси)хинолин-4-ил]окси}фенил)-n'-(4-фторфенил)циклопропан-1,1-дикарбоксамида и ее применение для лечения рака почек и печени |
| CN102718709A (zh) * | 2011-03-30 | 2012-10-10 | 北京德众万全药物技术开发有限公司 | 一种制备氨萘非特的新方法 |
| CN109490291B (zh) * | 2018-11-20 | 2021-05-11 | 上海应用技术大学 | 基于吸电子基取代的1,8-萘酰亚胺类化合物作为氟离子的显色试剂的用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES459497A1 (es) * | 1977-06-04 | 1978-04-16 | Made Labor Sa | Un metodo para la preparacion industrial de naftalimidas y sus derivados. |
| US4499266A (en) * | 1983-04-01 | 1985-02-12 | Warner-Lambert Company | 3,6-Dinitro-1,8-naphthalimides |
| US4614820A (en) * | 1983-04-01 | 1986-09-30 | Warner-Lambert Co. | 3,6-disubstituted-1,8-naphthalimides |
| US5183821A (en) | 1983-09-19 | 1993-02-02 | Laboratories Knoll, S.A. | Method for treating leukemias using N-(2-dimethylaminoethyl)-3-amino-1,8-naphthalimide for treating leukemias and solid tumors |
| US4665071A (en) | 1984-02-21 | 1987-05-12 | Warner-Lambert Company | 3,6-disubstituted-1,8-naphthalimides and methods for their production and use |
| DE3614414A1 (de) * | 1986-04-29 | 1987-11-05 | Knoll Ag | Neue benzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| DE3635711A1 (de) * | 1986-10-21 | 1988-04-28 | Knoll Ag | 5-nitrobenzo(de)isochinolin-1,3-dione, ihre herstellung und verwendung |
| DE3922771A1 (de) * | 1989-07-11 | 1991-01-24 | Knoll Ag | Amonafide-salze |
| US5420137A (en) | 1989-07-11 | 1995-05-30 | Knoll Ag | Amonafide salts |
| DE4106122A1 (de) * | 1991-02-27 | 1992-09-03 | Bayer Ag | Neue naphthalimide, diese enthaltende toner und die verwendung der neuen naphthalimide als additive fuer toner |
| BR9915648A (pt) * | 1998-11-25 | 2001-08-14 | Merck Patent Gmbh | Benzo [de] isoquinolina-1,3-dionas substituìdas |
| ATE305312T1 (de) | 2000-04-12 | 2005-10-15 | Chemgenex Pharmaceuticals Inc | Zusammensetzungen welche ein naphthalmid und ein antiproliferatives mittel enthalten |
| US6693198B2 (en) | 2002-04-22 | 2004-02-17 | Xanthus Life Sciences, Inc. | Amonafide salts |
-
2002
- 2002-04-22 US US10/128,129 patent/US6693198B2/en not_active Expired - Fee Related
- 2002-07-05 JP JP2002197809A patent/JP4630518B2/ja not_active Expired - Fee Related
-
2003
- 2003-04-22 CA CA002482445A patent/CA2482445A1/en not_active Abandoned
- 2003-04-22 DE DE60313156T patent/DE60313156T2/de not_active Expired - Lifetime
- 2003-04-22 AT AT03718511T patent/ATE359273T1/de not_active IP Right Cessation
- 2003-04-22 WO PCT/US2003/012619 patent/WO2003089415A1/en not_active Ceased
- 2003-04-22 EP EP03718511A patent/EP1499595B1/en not_active Expired - Lifetime
- 2003-04-22 AU AU2003221771A patent/AU2003221771B2/en not_active Ceased
- 2003-04-22 ES ES03718511T patent/ES2287463T3/es not_active Expired - Lifetime
- 2003-10-20 US US10/690,458 patent/US6989390B2/en not_active Expired - Fee Related
-
2009
- 2009-08-27 JP JP2009197462A patent/JP2010006831A/ja active Pending
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