SK621990A3 - Derivative of 1,5-diiodo-£2s,r|-3-oxapentane and method for producing the same - Google Patents
Derivative of 1,5-diiodo-£2s,r|-3-oxapentane and method for producing the same Download PDFInfo
- Publication number
- SK621990A3 SK621990A3 SK6219-90A SK621990A SK621990A3 SK 621990 A3 SK621990 A3 SK 621990A3 SK 621990 A SK621990 A SK 621990A SK 621990 A3 SK621990 A3 SK 621990A3
- Authority
- SK
- Slovakia
- Prior art keywords
- oxapentane
- derivative
- diiodo
- preparation
- methoxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000002083 iodinating effect Effects 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 229960004679 doxorubicin Drugs 0.000 abstract 1
- 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 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- 238000004809 thin layer chromatography Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229940022682 acetone Drugs 0.000 description 6
- 229940045799 anthracyclines and related substance Drugs 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 4
- 229930182470 glycoside Natural products 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- PADZQGJLBROXLI-YFKPBYRVSA-N (2s)-2-(2-hydroxyethoxy)-2-methoxyethanol Chemical compound CO[C@H](CO)OCCO PADZQGJLBROXLI-YFKPBYRVSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- XOFIBYLQFDNQQG-LJQANCHMSA-N 2-[(1r)-1-methoxy-2-(4-methylphenyl)sulfonyloxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C([C@H](OC)OCCOS(=O)(=O)C=1C=CC(C)=CC=1)OS(=O)(=O)C1=CC=C(C)C=C1 XOFIBYLQFDNQQG-LJQANCHMSA-N 0.000 description 3
- XOFIBYLQFDNQQG-IBGZPJMESA-N 2-[(1s)-1-methoxy-2-(4-methylphenyl)sulfonyloxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C([C@@H](OC)OCCOS(=O)(=O)C=1C=CC(C)=CC=1)OS(=O)(=O)C1=CC=C(C)C=C1 XOFIBYLQFDNQQG-IBGZPJMESA-N 0.000 description 3
- ALEDGHAEHAUNTA-RUZDIDTESA-N 2-[(1s)-2-(4-methylphenyl)sulfonyloxy-1-phenylmethoxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCO[C@H](OCC=1C=CC=CC=1)COS(=O)(=O)C1=CC=C(C)C=C1 ALEDGHAEHAUNTA-RUZDIDTESA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003118 aryl group Chemical group 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
- 239000000543 intermediate Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- -1 periodate compound Chemical class 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- YEZXEWXONCOWQT-SSDOTTSWSA-N 2-[(1r)-2-iodo-1-(2-iodoethoxy)ethoxy]propane Chemical compound CC(C)O[C@H](CI)OCCI YEZXEWXONCOWQT-SSDOTTSWSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- YWAIDTJFALVPHL-RXMQYKEDSA-N (1r)-2-iodo-1-(2-iodoethoxy)-1-methoxyethane Chemical compound CO[C@@H](CI)OCCI YWAIDTJFALVPHL-RXMQYKEDSA-N 0.000 description 1
- YWAIDTJFALVPHL-YFKPBYRVSA-N (1s)-2-iodo-1-(2-iodoethoxy)-1-methoxyethane Chemical compound CO[C@H](CI)OCCI YWAIDTJFALVPHL-YFKPBYRVSA-N 0.000 description 1
- PADZQGJLBROXLI-RXMQYKEDSA-N (2r)-2-(2-hydroxyethoxy)-2-methoxyethanol Chemical compound CO[C@@H](CO)OCCO PADZQGJLBROXLI-RXMQYKEDSA-N 0.000 description 1
- OIYPNUBAMNZWAB-SSDOTTSWSA-N (2r)-2-(2-hydroxyethoxy)-2-propan-2-yloxyethanol Chemical compound CC(C)O[C@H](CO)OCCO OIYPNUBAMNZWAB-SSDOTTSWSA-N 0.000 description 1
- WZOMEFALYDMUDO-LLVKDONJSA-N (2s)-2-(2-hydroxyethoxy)-2-phenylmethoxyethanol Chemical compound OCCO[C@@H](CO)OCC1=CC=CC=C1 WZOMEFALYDMUDO-LLVKDONJSA-N 0.000 description 1
- CUOMYDZNJOUCKP-YFKPBYRVSA-N (2s)-2-methoxy-2-(2-oxoethoxy)acetaldehyde Chemical compound CO[C@H](C=O)OCC=O CUOMYDZNJOUCKP-YFKPBYRVSA-N 0.000 description 1
- WZOMEFALYDMUDO-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-2-phenylmethoxyethanol Chemical compound OCCOC(CO)OCC1=CC=CC=C1 WZOMEFALYDMUDO-UHFFFAOYSA-N 0.000 description 1
- BCVJOHKWNDSWKX-OAQYLSRUSA-N 2-[(1r)-2-(4-methylphenyl)sulfonyloxy-1-propan-2-yloxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C([C@@H](OC(C)C)OCCOS(=O)(=O)C=1C=CC(C)=CC=1)OS(=O)(=O)C1=CC=C(C)C=C1 BCVJOHKWNDSWKX-OAQYLSRUSA-N 0.000 description 1
- LFSFHTZBPADHSO-FQEVSTJZSA-N 2-[(1s)-1-ethoxy-2-(4-methylphenyl)sulfonyloxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C([C@@H](OCC)OCCOS(=O)(=O)C=1C=CC(C)=CC=1)OS(=O)(=O)C1=CC=C(C)C=C1 LFSFHTZBPADHSO-FQEVSTJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JDHAEJZFBVAHTJ-SCSAIBSYSA-N IC(O[C@H](C)OC)(C)I Chemical compound IC(O[C@H](C)OC)(C)I JDHAEJZFBVAHTJ-SCSAIBSYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- NFGJXFFDMVOUCD-LLVKDONJSA-N [(1s)-2-iodo-1-(2-iodoethoxy)ethoxy]methylbenzene Chemical compound ICCO[C@@H](CI)OCC1=CC=CC=C1 NFGJXFFDMVOUCD-LLVKDONJSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000010792 warming Methods 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)
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 |
|---|---|
| SK278994B6 SK278994B6 (sk) | 1998-05-06 |
| SK621990A3 true SK621990A3 (en) | 1998-05-06 |
Family
ID=26296395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK6219-90A SK621990A3 (en) | 1989-12-19 | 1990-12-12 | Derivative of 1,5-diiodo-£2s,r|-3-oxapentane and method for producing the same |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP0434960B1 (enExample) |
| JP (1) | JP3300342B2 (enExample) |
| KR (1) | KR0183033B1 (enExample) |
| CN (2) | CN1024922C (enExample) |
| AT (1) | ATE143023T1 (enExample) |
| AU (1) | AU636429B2 (enExample) |
| CA (1) | CA2046857C (enExample) |
| CZ (1) | CZ281949B6 (enExample) |
| DE (1) | DE69028610T2 (enExample) |
| DK (1) | DK0434960T3 (enExample) |
| ES (1) | ES2094136T3 (enExample) |
| FI (1) | FI97389C (enExample) |
| GR (1) | GR3021557T3 (enExample) |
| HR (1) | HRP921226B1 (enExample) |
| HU (2) | HU209433B (enExample) |
| IE (1) | IE81174B1 (enExample) |
| IL (3) | IL111527A (enExample) |
| MY (1) | MY119192A (enExample) |
| NO (2) | NO175533C (enExample) |
| NZ (1) | NZ243695A (enExample) |
| PT (1) | PT96226B (enExample) |
| RU (1) | RU2100366C1 (enExample) |
| SI (1) | SI9012379B (enExample) |
| SK (1) | SK621990A3 (enExample) |
| TW (1) | TW208019B (enExample) |
| UA (1) | UA27108A1 (enExample) |
| WO (1) | WO1991009046A1 (enExample) |
| YU (1) | YU48136B (enExample) |
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 |
| ES2274823T3 (es) * | 1999-12-29 | 2007-06-01 | Immunogen, Inc. | Agentes cototoxicos que comprenden doxorrubicinas y daunorrubicinas y su utilizacion terapeutica. |
| CA2484761C (en) | 2002-05-24 | 2010-11-09 | Angiotech International Ag | Compositions and methods for coating medical implants |
| JP2006515186A (ja) | 2002-09-26 | 2006-05-25 | 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 | 血管周囲ラップ |
| US20040225077A1 (en) | 2002-12-30 | 2004-11-11 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| EP1605951A1 (en) * | 2003-03-18 | 2005-12-21 | Pharmacia Italia S.p.A. | Combined therapy comprising nemorubicin and a cyclooxygenase-2-inhibitor |
| EA200970116A1 (ru) * | 2006-07-12 | 2009-08-28 | НЕРВИАНО МЕДИКАЛ САЙЕНСИЗ С.р.л. | Кристаллический гидрохлорид неморубицина |
| 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 |
| ES2533710T3 (es) * | 2010-12-02 | 2015-04-14 | Nerviano Medical Sciences S.R.L. | Proceso para la preparación de derivados de morfolinil antraciclina |
| US9828405B2 (en) | 2013-04-29 | 2017-11-28 | Nerviano Medical Sciences S.R.L. | Morpholinyl anthracycline derivatives |
| EP3779446A1 (en) | 2013-12-11 | 2021-02-17 | University of Massachusetts | Compositions and methods for treating disease using salmonella t3ss effector protein (sipa) |
| WO2016071418A1 (en) | 2014-11-05 | 2016-05-12 | Nerviano Medical Sciences S.R.L. | Functionalized morpholinyl anthracycline derivatives |
| 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 |
| WO2024038065A1 (en) * | 2022-08-15 | 2024-02-22 | Synaffix B.V. | Anthracyclins and conjugates thereof |
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 |
-
1990
- 1990-11-15 ES ES90121905T patent/ES2094136T3/es not_active Expired - Lifetime
- 1990-11-15 DE DE69028610T patent/DE69028610T2/de not_active Expired - Fee Related
- 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 DK DK90121905.5T patent/DK0434960T3/da active
- 1990-12-12 IL IL111527A patent/IL111527A/en not_active IP Right Cessation
- 1990-12-12 NZ NZ243695A patent/NZ243695A/xx unknown
- 1990-12-12 SK SK6219-90A patent/SK621990A3/sk unknown
- 1990-12-12 CZ CS906219A patent/CZ281949B6/cs not_active IP Right Cessation
- 1990-12-12 IL IL9664390A patent/IL96643A/en not_active IP Right Cessation
- 1990-12-14 TW TW079110518A patent/TW208019B/zh active
- 1990-12-17 IE IE454390A patent/IE81174B1/en not_active IP Right Cessation
- 1990-12-17 MY MYPI94001426A patent/MY119192A/en unknown
- 1990-12-17 PT PT96226A patent/PT96226B/pt not_active IP Right Cessation
- 1990-12-17 YU YU237990A patent/YU48136B/sh unknown
- 1990-12-17 SI SI9012379A patent/SI9012379B/sl not_active IP Right Cessation
- 1990-12-18 AU AU69194/91A patent/AU636429B2/en not_active Ceased
- 1990-12-18 CN CN90110144A patent/CN1024922C/zh not_active Expired - Fee Related
- 1990-12-18 CA CA002046857A patent/CA2046857C/en not_active Expired - Fee Related
- 1990-12-18 UA UA5001540A patent/UA27108A1/uk unknown
- 1990-12-18 HU HU9200656A patent/HU209433B/hu unknown
- 1990-12-18 RU SU915001540A patent/RU2100366C1/ru not_active IP Right Cessation
- 1990-12-18 HU HU912994A patent/HU208148B/hu not_active IP Right Cessation
- 1990-12-18 KR KR1019910700930A patent/KR0183033B1/ko not_active Expired - Fee Related
- 1990-12-18 WO PCT/EP1990/002229 patent/WO1991009046A1/en not_active Ceased
- 1990-12-18 JP JP50124491A patent/JP3300342B2/ja not_active Expired - Fee Related
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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
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1996
- 1996-11-06 GR GR960402934T patent/GR3021557T3/el unknown
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