DE69103428T2 - Latente alkylierungsubstituenten enthaltende anthracycline-analoge. - Google Patents
Latente alkylierungsubstituenten enthaltende anthracycline-analoge.Info
- Publication number
- DE69103428T2 DE69103428T2 DE69103428T DE69103428T DE69103428T2 DE 69103428 T2 DE69103428 T2 DE 69103428T2 DE 69103428 T DE69103428 T DE 69103428T DE 69103428 T DE69103428 T DE 69103428T DE 69103428 T2 DE69103428 T2 DE 69103428T2
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- doxorubicin
- nmr
- compound
- compound according
- 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 - Fee Related
Links
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- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 229960004679 doxorubicin Drugs 0.000 claims abstract description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
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- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical class ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003683 cardiac damage Effects 0.000 description 1
- 230000035567 cellular accumulation Effects 0.000 description 1
- BLLIIPIJZPKUEG-HPTNQIKVSA-N chembl3304020 Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=N)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 BLLIIPIJZPKUEG-HPTNQIKVSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005385 correlation spectroscopy for long-range coupling Methods 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- DVSDDICSXBCMQJ-UHFFFAOYSA-N diethyl 2-acetylbutanedioate Chemical compound CCOC(=O)CC(C(C)=O)C(=O)OCC DVSDDICSXBCMQJ-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- WGTGQGJDNAGBCC-UHFFFAOYSA-N hex-5-ene-1,2-diol Chemical compound OCC(O)CCC=C WGTGQGJDNAGBCC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-UHFFFAOYSA-N 0.000 description 1
- 239000012023 mustard compounds Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 238000002638 palliative care Methods 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- RJXQSIKBGKVNRT-UHFFFAOYSA-N phosphoramide mustard Chemical compound ClCCN(P(O)(=O)N)CCCl RJXQSIKBGKVNRT-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 208000037965 uterine sarcoma Diseases 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (23)
1. Verbindung der Formel
Anthracyclin
in der
Anthracyclin Doxorubicin, Daunorubicin oder ein Derivat
derselben;
N das 3'-Stickstoffatom des Daunosamins;
Ra H oder Alkyl;
X O, S, CRc&sub2; oder NRc, wobei Rc H oder Alkyl ist;
Rb Alkyl oder Aryl;
n 1 bis 6; und
m 0 bis 6
bedeuten.
2. Verbindung nach Anspruch 1, bei der Rc H, Methyl, Ethyl,
Propyl oder Butyl bedeuten.
3. Verbindung nach Anspruch 1, bei der Ra H, Rb CH&sub3;, X CRc&sub2;,
Rc H, n 2 und m 1 bedeuten.
4. Verbindung nach Anspruch 1, bei CH&sub3; H, Rb CH&sub3;, X O,
n 2 und m 1 bedeuten.
5. Verbindung nach Anspruch 1, bei der Ra H, Rb CH&sub3;, x CRc&sub2;,
Rc H, n 2 und m 0 bedeuten.
6. Verbindung nach Anspruch 1, bei der Ra H, Rb CH&sub3;, x CRc&sub2;,
Rc H, n 2 und m 2 bedeuten.
7. Verbindung nach Anspruch 1, bei der Ra H, Rb CH&sub3;, X CRc&sub2;,
Rc H, n 2 und m 0 bedeuten.
8. Verbindung nach Anspruch 1, bei der Ra H, R CH&sub3;, X O, n 2
und m 2 bedeuten.
9. Verbindung nach Anspruch 1, bei der Ra H, Rb CH&sub3;, X CRc&sub2;,
Rc H, n 2 und m 4 bedeuten.
10. Verbindung nach Anspruch 1, bei der Ra H, Methyl, Ethyl,
Propyl oder Butyl bedeuten.
11. Verbindung nach Anspruch 1, bei der Rb Alkyl bedeutet.
12. Verbindung nach Anspruch 1, bei der Rb Alkyl, Methyl,
Ethyl, Propyl oder Butyl bedeutet.
13. Verbindung nach Anspruch 1, bei der Rb Methyl bedeutet.
14. Verbindung nach Anspruch 1, bei der X CRc&sub2;, Rc H, und m +
n von 1 bis 9 bedeuten.
15. Verbindung nach Anspruch 1, bei der X O, S oder NRc und Rc
H bedeuten.
16. Verbindung nach Anspruch 1, bei der Anthracyclin
Doxorubicin bedeutet.
17. N-(5,5-Diacetoxypentyl)-doxorubicin oder ein
pharmazeutisch verträgliches Salz desselben.
18. N-(2,2-Diacetoxyethyloxyethyl)-doxorubicin oder ein
pharmazeutisch verträgliches Salz desselben.
19. N-(4,4-Diacetoxybutyl)-doxorubicin oder ein pharmazeutisch
verträgliches Salz desselben.
20. N-(6,6-Diacetoxyhexyl)-doxorubicin oder ein pharmazeutisch
verträgliches Salz desselben.
21. N-(4,4-Diacetoxy-3,3-dimethylbutyl)-doxorubicin oder ein
pharmazeutisch verträgliches Salz desselben.
22. N-(3,3-Diacetoxypropyloxy-1-ethyl)-doxorubicin oder ein
pharmazeutisch verträgliches Salz desselben.
23. N-(8,8-Diacetoxyoctyl)-doxorubicin oder ein pharmazeutisch
verträgliches Salz desselben.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/608,149 US5196522A (en) | 1990-11-01 | 1990-11-01 | Anthracycline analogues bearing latent alkylating substituents |
| PCT/US1991/007687 WO1992007866A1 (en) | 1990-11-01 | 1991-10-16 | Anthracycline analogues bearing latent alkylating substituents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69103428D1 DE69103428D1 (de) | 1994-09-15 |
| DE69103428T2 true DE69103428T2 (de) | 1995-03-30 |
Family
ID=24435271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69103428T Expired - Fee Related DE69103428T2 (de) | 1990-11-01 | 1991-10-16 | Latente alkylierungsubstituenten enthaltende anthracycline-analoge. |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5196522A (de) |
| EP (1) | EP0555358B1 (de) |
| JP (1) | JP3051170B2 (de) |
| AT (1) | ATE109787T1 (de) |
| AU (1) | AU642798B2 (de) |
| CA (1) | CA2094914C (de) |
| DE (1) | DE69103428T2 (de) |
| DK (1) | DK0555358T3 (de) |
| WO (1) | WO1992007866A1 (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5196522A (en) * | 1990-11-01 | 1993-03-23 | Board Of Regents, The University Of Texas System | Anthracycline analogues bearing latent alkylating substituents |
| US5622929A (en) * | 1992-01-23 | 1997-04-22 | Bristol-Myers Squibb Company | Thioether conjugates |
| US6218519B1 (en) | 1996-04-12 | 2001-04-17 | Pro-Neuron, Inc. | Compounds and methods for the selective treatment of cancer and bacterial infections |
| US6677309B1 (en) | 1997-04-11 | 2004-01-13 | University Technology Corporation | Anti-cancer drug aldehyde conjugate drugs with enhanced cytotoxicity compounds, compositions and methods |
| US20040038904A1 (en) * | 2002-05-21 | 2004-02-26 | Angela Ogden | Method of treating multiple sclerosis |
| US20050208037A1 (en) * | 2003-10-21 | 2005-09-22 | Board Of Regents, The University Of Texas System | Thioredoxin increases redox-cycling of anticancer agents thereby sensitizes cancer cells to apoptosis |
| WO2005086951A2 (en) * | 2004-03-10 | 2005-09-22 | Threshold Pharmaceuticals, Inc. | Hypoxia-activated anti-cancer agents |
| US20070060534A1 (en) * | 2005-06-30 | 2007-03-15 | Threshold Pharmaceuticals, Inc. | Anthracycline analogs |
| US7470672B2 (en) | 2006-07-31 | 2008-12-30 | Savvipharm Inc. | Compositions and methods of reducing tissue levels of drugs when given as orotate derivatives |
| US7750018B2 (en) * | 2006-12-06 | 2010-07-06 | Tactical Therapeutics, Inc | Use of carboxiamidotriazole (CAI) orotate in macular degeneration |
| EP2538929A4 (de) | 2010-02-25 | 2014-07-09 | Univ Johns Hopkins | Verzögerte freisetzung von therapiemitteln in einen teil des auges |
| US10307372B2 (en) | 2010-09-10 | 2019-06-04 | The Johns Hopkins University | Rapid diffusion of large polymeric nanoparticles in the mammalian brain |
| US9327037B2 (en) | 2011-02-08 | 2016-05-03 | The Johns Hopkins University | Mucus penetrating gene carriers |
| AU2013209452B2 (en) | 2012-01-19 | 2015-11-05 | The Johns Hopkins University | Nanoparticle formulations with enhanced mucosal penetration |
| JP6138904B2 (ja) | 2012-03-16 | 2017-05-31 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 活性剤の送達のための非線状マルチブロックコポリマー薬物コンジュゲート |
| EP2825206A1 (de) | 2012-03-16 | 2015-01-21 | The Johns Hopkins University | Formulierungen mit kontrollierter freisetzung zur verabreichung von hif-1-hemmern |
| US9533068B2 (en) | 2012-05-04 | 2017-01-03 | The Johns Hopkins University | Drug loaded microfiber sutures for ophthalmic application |
| AU2013256008B2 (en) | 2012-05-04 | 2016-02-25 | The Johns Hopkins University | Lipid-based drug carriers for rapid penetration through mucus linings |
| US10568975B2 (en) | 2013-02-05 | 2020-02-25 | The Johns Hopkins University | Nanoparticles for magnetic resonance imaging tracking and methods of making and using thereof |
| CN105209068A (zh) | 2013-02-07 | 2015-12-30 | 免疫医疗公司 | 用于靶向癌症治疗的缀合至抗体的高效2-吡咯啉多柔比星的前药形式(p2pdox) |
| ES2947557T3 (es) | 2013-09-06 | 2023-08-11 | Vanda Pharmaceuticals Inc | Tratamiento de afecciones mediadas por CYR61 y VEGF |
| WO2015127368A1 (en) | 2014-02-23 | 2015-08-27 | The Johns Hopkins University | Hypotonic microbicidal formulations and methods of use |
| CA2961774C (en) | 2014-10-07 | 2023-05-23 | Immunomedics, Inc. | Neoadjuvant use of antibody-drug conjugates |
| AU2016211696B2 (en) | 2015-01-27 | 2018-05-10 | The Johns Hopkins University | Hypotonic hydrogel formulations for enhanced transport of active agents at mucosal surfaces |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035566A (en) * | 1975-09-25 | 1977-07-12 | Sidney Farber Cancer Institute, Inc. | N-trifluoroacetyladriamycin-14-alkanoates and therapeutic compositions containing same |
| US4109076A (en) * | 1977-09-08 | 1978-08-22 | Sri International | 5-iminodaunomycin |
| US4301277A (en) * | 1980-10-20 | 1981-11-17 | Sri International | 3-Deamino-3-(4-morpholinyl) derivatives of daunorubicin and doxorubicin |
| US4950738A (en) * | 1984-09-13 | 1990-08-21 | Cytogen Corporation | Amine derivatives of anthracycline antibiotics |
| US4464529A (en) * | 1982-07-20 | 1984-08-07 | Sri International | Analogues of morpholinyl daunorubicin and morpholinyl doxorubicin |
| US4826964A (en) * | 1982-07-20 | 1989-05-02 | Sri International | Bridged oxygen analogs of daunorubcin and doxorubicin |
| US4585859A (en) * | 1983-05-24 | 1986-04-29 | Sri International | Analogues of morpholinyl daunorubicin and morpholinyl doxorubicin |
| GB8508508D0 (en) * | 1985-04-01 | 1985-05-09 | Creighton A M | Pharmaceutical compositions |
| FR2591599B1 (fr) * | 1985-12-17 | 1988-08-05 | Hoechst Lab | Nouvelles anthracyclines et medicaments les contenant |
| US5091552A (en) | 1986-06-30 | 1992-02-25 | Board Of Regents, The University Of Texas System | Novel antitumor aldophosphamide analogs |
| US4841085A (en) * | 1986-06-30 | 1989-06-20 | Board Of Regents, University Of Texas System | Aldophosphamides |
| US5196522A (en) * | 1990-11-01 | 1993-03-23 | Board Of Regents, The University Of Texas System | Anthracycline analogues bearing latent alkylating substituents |
-
1990
- 1990-11-01 US US07/608,149 patent/US5196522A/en not_active Expired - Lifetime
-
1991
- 1991-10-16 WO PCT/US1991/007687 patent/WO1992007866A1/en active IP Right Grant
- 1991-10-16 CA CA002094914A patent/CA2094914C/en not_active Expired - Fee Related
- 1991-10-16 AU AU90292/91A patent/AU642798B2/en not_active Ceased
- 1991-10-16 AT AT91920574T patent/ATE109787T1/de not_active IP Right Cessation
- 1991-10-16 DK DK91920574.0T patent/DK0555358T3/da active
- 1991-10-16 EP EP91920574A patent/EP0555358B1/de not_active Expired - Lifetime
- 1991-10-16 JP JP3518598A patent/JP3051170B2/ja not_active Expired - Fee Related
- 1991-10-16 DE DE69103428T patent/DE69103428T2/de not_active Expired - Fee Related
-
1995
- 1995-05-15 US US08/441,240 patent/US6284737B1/en not_active Expired - Fee Related
-
2001
- 2001-03-02 US US09/796,606 patent/US6433150B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3051170B2 (ja) | 2000-06-12 |
| WO1992007866A1 (en) | 1992-05-14 |
| DK0555358T3 (da) | 1994-12-05 |
| US6284737B1 (en) | 2001-09-04 |
| US6433150B2 (en) | 2002-08-13 |
| CA2094914C (en) | 1998-02-10 |
| JPH06502417A (ja) | 1994-03-17 |
| AU642798B2 (en) | 1993-10-28 |
| EP0555358B1 (de) | 1994-08-10 |
| AU9029291A (en) | 1992-05-26 |
| US5196522A (en) | 1993-03-23 |
| US20010053845A1 (en) | 2001-12-20 |
| CA2094914A1 (en) | 1992-05-02 |
| DE69103428D1 (de) | 1994-09-15 |
| EP0555358A1 (de) | 1993-08-18 |
| ATE109787T1 (de) | 1994-08-15 |
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