IL96643A - 3' - דהמינו -'s) - 2" ) - 3( - מתוקסי - " 4 - מורפוליניל( -דוקסורוביצין כירלי, הכנתו ותכשירי רוקחות המכילים אותו - Google Patents
3' - דהמינו -'s) - 2" ) - 3( - מתוקסי - " 4 - מורפוליניל( -דוקסורוביצין כירלי, הכנתו ותכשירי רוקחות המכילים אותוInfo
- Publication number
- IL96643A IL96643A IL9664390A IL9664390A IL96643A IL 96643 A IL96643 A IL 96643A IL 9664390 A IL9664390 A IL 9664390A IL 9664390 A IL9664390 A IL 9664390A IL 96643 A IL96643 A IL 96643A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- doxorubicin
- compound
- derivative
- deamino
- Prior art date
Links
- 229960004679 doxorubicin Drugs 0.000 title claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 9
- AOJJSUZBOXZQNB-TZSSRYMLSA-N doxorubicine Natural products O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims abstract description 31
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000002246 antineoplastic agent Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 229930182470 glycoside Natural products 0.000 claims description 9
- 150000002338 glycosides Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical class N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229960002918 doxorubicin hydrochloride Drugs 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 2
- 230000002083 iodinating effect Effects 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- SXCIMUIAZXOVIR-PUCKCBAPSA-N (7s,9s)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2r,4s,5s,6s)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1 SXCIMUIAZXOVIR-PUCKCBAPSA-N 0.000 claims 1
- 239000003817 anthracycline antibiotic agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 2
- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000013096 assay test Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 230000006364 cellular survival Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 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
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL111527A IL111527A (he) | 1989-12-19 | 1990-12-12 | 1,5-דייודו-)s(2-אלקוקסי )או בנזילוקסי(-3-אוקסא-פנטאנים והכנתם |
| IL11152794A IL111527A0 (en) | 1989-12-19 | 1994-11-04 | 1,5-Diiodo-2(s)-alkoxy (or benzyloxy)-3-oxa-pentanes and their preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898928654A GB8928654D0 (en) | 1989-12-19 | 1989-12-19 | Preparation of 2-methoxy-4-morpholinyl anthracyclines |
| GB909007513A GB9007513D0 (en) | 1990-04-03 | 1990-04-03 | Morpholinyl derivatives of doxorubicin and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96643A0 IL96643A0 (en) | 1991-09-16 |
| IL96643A true IL96643A (he) | 1995-01-24 |
Family
ID=26296395
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9664390A IL96643A (he) | 1989-12-19 | 1990-12-12 | 3' - דהמינו -'s) - 2" ) - 3( - מתוקסי - " 4 - מורפוליניל( -דוקסורוביצין כירלי, הכנתו ותכשירי רוקחות המכילים אותו |
| IL111527A IL111527A (he) | 1989-12-19 | 1990-12-12 | 1,5-דייודו-)s(2-אלקוקסי )או בנזילוקסי(-3-אוקסא-פנטאנים והכנתם |
| IL11152794A IL111527A0 (en) | 1989-12-19 | 1994-11-04 | 1,5-Diiodo-2(s)-alkoxy (or benzyloxy)-3-oxa-pentanes and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL111527A IL111527A (he) | 1989-12-19 | 1990-12-12 | 1,5-דייודו-)s(2-אלקוקסי )או בנזילוקסי(-3-אוקסא-פנטאנים והכנתם |
| IL11152794A IL111527A0 (en) | 1989-12-19 | 1994-11-04 | 1,5-Diiodo-2(s)-alkoxy (or benzyloxy)-3-oxa-pentanes and their preparation |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP0434960B1 (he) |
| JP (1) | JP3300342B2 (he) |
| KR (1) | KR0183033B1 (he) |
| CN (2) | CN1024922C (he) |
| AT (1) | ATE143023T1 (he) |
| AU (1) | AU636429B2 (he) |
| CA (1) | CA2046857C (he) |
| CZ (1) | CZ281949B6 (he) |
| DE (1) | DE69028610T2 (he) |
| DK (1) | DK0434960T3 (he) |
| ES (1) | ES2094136T3 (he) |
| FI (1) | FI97389C (he) |
| GR (1) | GR3021557T3 (he) |
| HR (1) | HRP921226B1 (he) |
| HU (2) | HU209433B (he) |
| IE (1) | IE81174B1 (he) |
| IL (3) | IL96643A (he) |
| MY (1) | MY119192A (he) |
| NO (2) | NO175533C (he) |
| NZ (1) | NZ243695A (he) |
| PT (1) | PT96226B (he) |
| RU (1) | RU2100366C1 (he) |
| SI (1) | SI9012379B (he) |
| SK (1) | SK621990A3 (he) |
| TW (1) | TW208019B (he) |
| UA (1) | UA27108A1 (he) |
| WO (1) | WO1991009046A1 (he) |
| YU (1) | YU48136B (he) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5843903A (en) * | 1995-11-27 | 1998-12-01 | The Administrators Of The Tulane Educational Fund | Targeted cytotoxic anthracycline analogs |
| DK1242438T3 (da) * | 1999-12-29 | 2007-02-12 | Immunogen Inc | Cytotoksiske midler omfattende modificerede doxorubiciner og daunorubiciner og deres terapeutiske anvendelse |
| MXPA04011651A (es) | 2002-05-24 | 2005-03-07 | Angiotech Pharm Inc | Composiciones y metodo para recubrir implantes medicos. |
| DE60325240D1 (de) | 2002-09-26 | 2009-01-22 | Angiotech Int Ag | Perivaskuläre hüllen |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| AU2004222527A1 (en) * | 2003-03-18 | 2004-09-30 | Pharmacia Italia Spa | Combined therapy comprising nemorubicin and a cyclooxygenase-2-inhibitor |
| JP2009542765A (ja) * | 2006-07-12 | 2009-12-03 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | 結晶性ネモルビシン塩酸塩 |
| AU2009235897B2 (en) * | 2008-04-11 | 2012-04-12 | Tianjin Hemay Oncology Pharmaceutical Co., Ltd | Anthracycline antibiotic derivatives with high activity, preparation methods and uses thereof |
| CN101353361B (zh) * | 2008-08-08 | 2011-06-01 | 中国人民解放军第四军医大学 | 一种阿霉素前体药物的制备方法及其应用 |
| WO2012073217A1 (en) * | 2010-12-02 | 2012-06-07 | Nerviano Medical Sciences S.R.L. | Process for the preparation of morpholinyl anthracycline derivatives |
| WO2014177441A1 (en) | 2013-04-29 | 2014-11-06 | Nerviano Medical Sciences S.R.L. | New morpholinyl anthracycline derivatives |
| EP3084445B1 (en) | 2013-12-11 | 2020-10-28 | University of Massachusetts | Compositions and methods for treating disease using salmonella t3ss effector protein (sipa) |
| RU2715902C2 (ru) | 2014-11-05 | 2020-03-04 | НЕРВИАНО МЕДИКАЛ САЙЕНСИЗ С.р.л. | Функционализированные производные морфолинилантрациклина |
| CN115043895A (zh) * | 2022-07-15 | 2022-09-13 | 戊言医药科技（上海）有限公司 | 一种pnu-159682及其中间体的制备方法 |
| JP2025526869A (ja) * | 2022-08-15 | 2025-08-15 | シンアフィックス ビー．ブイ． | アントラサイクリン及びそのコンジュゲート |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883443A (en) * | 1956-07-13 | 1959-04-21 | Ruetschi Karl | Lead-acid storage battery |
| US4423123A (en) * | 1980-04-17 | 1983-12-27 | Shin-Kobe Electric Machinery Co., Ltd. | Electric storage battery and a method of making the same |
| JPS57163393A (en) * | 1981-03-27 | 1982-10-07 | Microbial Chem Res Found | Novel anthracyclin derivative and its preparation |
| US4363857A (en) * | 1981-10-16 | 1982-12-14 | General Motors Corporation | Laminated metal-plastic battery grid |
| US4710564A (en) * | 1985-01-18 | 1987-12-01 | Microbial Chemistry Research Foundation | Anthracycline compounds |
| GB2172594B (en) * | 1985-03-22 | 1988-06-08 | Erba Farmitalia | New morpholino derivatives of daunorubicin and doxorubicin |
| JPS6215323A (ja) * | 1986-02-14 | 1987-01-23 | Dainippon Ink & Chem Inc | 微多孔中空繊維の製造法 |
| US4861836A (en) * | 1986-12-23 | 1989-08-29 | Daikin Industries Ltd. | Novel, iodine-containing compound, preparation thereof and block copolymer comprising the same |
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1990
- 1990-11-15 ES ES90121905T patent/ES2094136T3/es not_active Expired - Lifetime
- 1990-11-15 DK DK90121905.5T patent/DK0434960T3/da active
- 1990-11-15 EP EP90121905A patent/EP0434960B1/en not_active Expired - Lifetime
- 1990-11-15 AT AT90121905T patent/ATE143023T1/de not_active IP Right Cessation
- 1990-11-15 DE DE69028610T patent/DE69028610T2/de not_active Expired - Fee Related
- 1990-12-12 NZ NZ243695A patent/NZ243695A/xx unknown
- 1990-12-12 CZ CS906219A patent/CZ281949B6/cs not_active IP Right Cessation
- 1990-12-12 SK SK6219-90A patent/SK621990A3/sk unknown
- 1990-12-12 IL IL9664390A patent/IL96643A/he not_active IP Right Cessation
- 1990-12-12 IL IL111527A patent/IL111527A/he not_active IP Right Cessation
- 1990-12-14 TW TW079110518A patent/TW208019B/zh active
- 1990-12-17 MY MYPI94001426A patent/MY119192A/en unknown
- 1990-12-17 YU YU237990A patent/YU48136B/sh unknown
- 1990-12-17 PT PT96226A patent/PT96226B/pt not_active IP Right Cessation
- 1990-12-17 SI SI9012379A patent/SI9012379B/sl not_active IP Right Cessation
- 1990-12-17 IE IE454390A patent/IE81174B1/en not_active IP Right Cessation
- 1990-12-18 CA CA002046857A patent/CA2046857C/en not_active Expired - Fee Related
- 1990-12-18 CN CN90110144A patent/CN1024922C/zh not_active Expired - Fee Related
- 1990-12-18 WO PCT/EP1990/002229 patent/WO1991009046A1/en not_active Ceased
- 1990-12-18 AU AU69194/91A patent/AU636429B2/en not_active Ceased
- 1990-12-18 JP JP50124491A patent/JP3300342B2/ja not_active Expired - Fee Related
- 1990-12-18 HU HU9200656A patent/HU209433B/hu unknown
- 1990-12-18 UA UA5001540A patent/UA27108A1/uk unknown
- 1990-12-18 HU HU912994A patent/HU208148B/hu not_active IP Right Cessation
- 1990-12-18 RU SU915001540A patent/RU2100366C1/ru not_active IP Right Cessation
- 1990-12-18 KR KR1019910700930A patent/KR0183033B1/ko not_active Expired - Fee Related
-
1991
- 1991-08-14 NO NO913176A patent/NO175533C/no unknown
- 1991-08-16 FI FI913887A patent/FI97389C/fi active
-
1992
- 1992-11-11 HR HRP-2379/90A patent/HRP921226B1/xx not_active IP Right Cessation
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1993
- 1993-03-05 CN CN93102413A patent/CN1039708C/zh not_active Expired - Fee Related
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1994
- 1994-03-09 NO NO940831A patent/NO176911C/no unknown
- 1994-11-04 IL IL11152794A patent/IL111527A0/xx unknown
-
1996
- 1996-11-06 GR GR960402934T patent/GR3021557T3/el unknown
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