RU2443421C2 - Производные стауроспорина для применения при лечении альвеолярной рабдомиосаркомы - Google Patents
Производные стауроспорина для применения при лечении альвеолярной рабдомиосаркомы Download PDFInfo
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- RU2443421C2 RU2443421C2 RU2008123382/15A RU2008123382A RU2443421C2 RU 2443421 C2 RU2443421 C2 RU 2443421C2 RU 2008123382/15 A RU2008123382/15 A RU 2008123382/15A RU 2008123382 A RU2008123382 A RU 2008123382A RU 2443421 C2 RU2443421 C2 RU 2443421C2
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- alkyl
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- phenyl
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- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical class C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 title description 9
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000002062 proliferating effect Effects 0.000 claims abstract description 18
- 102100035427 Forkhead box protein O1 Human genes 0.000 claims abstract description 14
- 101000877727 Homo sapiens Forkhead box protein O1 Proteins 0.000 claims abstract description 14
- 230000005945 translocation Effects 0.000 claims abstract description 9
- 101000613490 Homo sapiens Paired box protein Pax-3 Proteins 0.000 claims description 10
- 102100040891 Paired box protein Pax-3 Human genes 0.000 claims description 10
- 206010039491 Sarcoma Diseases 0.000 claims description 7
- 206010065867 alveolar rhabdomyosarcoma Diseases 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 2
- -1 hydroxy, hydroxy Chemical group 0.000 description 449
- 125000000217 alkyl group Chemical group 0.000 description 143
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 91
- 150000001875 compounds Chemical class 0.000 description 88
- 229910052757 nitrogen Inorganic materials 0.000 description 63
- 150000003254 radicals Chemical class 0.000 description 60
- 125000004432 carbon atom Chemical group C* 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 39
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 36
- 229910052739 hydrogen Inorganic materials 0.000 description 35
- 239000001257 hydrogen Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 29
- 150000003839 salts Chemical class 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 28
- 125000002252 acyl group Chemical group 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 125000005037 alkyl phenyl group Chemical group 0.000 description 22
- 125000003545 alkoxy group Chemical group 0.000 description 21
- 229910052736 halogen Inorganic materials 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 125000003277 amino group Chemical group 0.000 description 20
- 150000002367 halogens Chemical class 0.000 description 20
- 229950010895 midostaurin Drugs 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- BMGQWWVMWDBQGC-IIFHNQTCSA-N midostaurin Chemical compound CN([C@H]1[C@H]([C@]2(C)O[C@@H](N3C4=CC=CC=C4C4=C5C(=O)NCC5=C5C6=CC=CC=C6N2C5=C43)C1)OC)C(=O)C1=CC=CC=C1 BMGQWWVMWDBQGC-IIFHNQTCSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
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- 125000000623 heterocyclic group Chemical group 0.000 description 17
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000005842 heteroatom Chemical group 0.000 description 14
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- 125000003342 alkenyl group Chemical group 0.000 description 12
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- 238000002360 preparation method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- FSPQCTGGIANIJZ-UHFFFAOYSA-N 2-[[(3,4-dimethoxyphenyl)-oxomethyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=C(C(N)=O)C(CCCC2)=C2S1 FSPQCTGGIANIJZ-UHFFFAOYSA-N 0.000 description 9
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 7
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- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 7
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
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- 125000005956 isoquinolyl group Chemical group 0.000 description 7
- 125000000842 isoxazolyl group Chemical group 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 7
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
- 125000005493 quinolyl group Chemical group 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
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- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- RDOIQAHITMMDAJ-UHFFFAOYSA-N loperamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 RDOIQAHITMMDAJ-UHFFFAOYSA-N 0.000 description 1
- 229960001571 loperamide Drugs 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
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- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229960002700 octreotide Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000002025 prostate sarcoma Diseases 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229940072272 sandostatin Drugs 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 238000013414 tumor xenograft model Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73622205P | 2005-11-14 | 2005-11-14 | |
| US60/736,222 | 2005-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008123382A RU2008123382A (ru) | 2009-12-27 |
| RU2443421C2 true RU2443421C2 (ru) | 2012-02-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008123382/15A RU2443421C2 (ru) | 2005-11-14 | 2006-11-13 | Производные стауроспорина для применения при лечении альвеолярной рабдомиосаркомы |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7973032B2 (enExample) |
| EP (1) | EP1951255A1 (enExample) |
| JP (1) | JP5308820B2 (enExample) |
| KR (1) | KR20080067654A (enExample) |
| CN (1) | CN101304749A (enExample) |
| AU (1) | AU2006313724B2 (enExample) |
| BR (1) | BRPI0618571A2 (enExample) |
| CA (1) | CA2629478C (enExample) |
| RU (1) | RU2443421C2 (enExample) |
| WO (1) | WO2007054579A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025132479A1 (en) * | 2023-12-18 | 2025-06-26 | Institut National de la Santé et de la Recherche Médicale | Flt3 inhibitor for modulating macrophages polarization |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093330A (en) * | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| RU2004115472A (ru) * | 2004-05-24 | 2004-10-10 | Рашид Камиль Оглы Гусейнов | Способ проведения операции на сосудах и устройство для проведения операции на сосудах |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7132458B2 (en) * | 1994-08-10 | 2006-11-07 | Chemaphor Inc. | Oxidized carotenoid fractions and ketoaldehyde useful as cell-differentiation inducers, cytostatic agents, and anti-tumor agents |
| AU6714396A (en) * | 1995-07-28 | 1997-02-26 | Trustees Of Boston University | Methods and compositions for treating cell proliferative disorders |
| CA2253608A1 (en) * | 1996-05-01 | 1997-11-06 | Louis Vignati | Therapeutic treatment for vegf related diseases |
| PT1441737E (pt) * | 2001-10-30 | 2006-12-29 | Dana Farber Cancer Inst Inc | Derivados de estrutura como inibidores da actividade do receptor de tirosina cinase flt3 |
| TWI324604B (en) | 2003-06-18 | 2010-05-11 | Novartis Ag | New use of staurosporine derivatives |
| DE602004030265D1 (de) * | 2003-09-19 | 2011-01-05 | Novartis Ag | Behandlung von gastrointestinalen stromatumoren mit imatinib und midostaurin |
| RU2269315C2 (ru) * | 2004-05-24 | 2006-02-10 | Рашид Кямиль Оглы Гусейнов | Способ соединения сосудов и устройство для герметизации надреза сосуда и перерезания стенки сосуда |
-
2006
- 2006-11-13 JP JP2008539452A patent/JP5308820B2/ja not_active Expired - Fee Related
- 2006-11-13 WO PCT/EP2006/068410 patent/WO2007054579A1/en not_active Ceased
- 2006-11-13 BR BRPI0618571-1A patent/BRPI0618571A2/pt not_active IP Right Cessation
- 2006-11-13 CN CNA2006800384359A patent/CN101304749A/zh active Pending
- 2006-11-13 CA CA2629478A patent/CA2629478C/en not_active Expired - Fee Related
- 2006-11-13 AU AU2006313724A patent/AU2006313724B2/en not_active Ceased
- 2006-11-13 EP EP06829981A patent/EP1951255A1/en not_active Withdrawn
- 2006-11-13 RU RU2008123382/15A patent/RU2443421C2/ru not_active IP Right Cessation
- 2006-11-13 KR KR1020087011406A patent/KR20080067654A/ko not_active Ceased
- 2006-11-13 US US12/090,626 patent/US7973032B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5093330A (en) * | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| RU2004115472A (ru) * | 2004-05-24 | 2004-10-10 | Рашид Камиль Оглы Гусейнов | Способ проведения операции на сосудах и устройство для проведения операции на сосудах |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101304749A (zh) | 2008-11-12 |
| JP2009515858A (ja) | 2009-04-16 |
| US7973032B2 (en) | 2011-07-05 |
| EP1951255A1 (en) | 2008-08-06 |
| CA2629478C (en) | 2013-10-15 |
| US20080280880A1 (en) | 2008-11-13 |
| KR20080067654A (ko) | 2008-07-21 |
| WO2007054579A1 (en) | 2007-05-18 |
| BRPI0618571A2 (pt) | 2011-09-06 |
| JP5308820B2 (ja) | 2013-10-09 |
| CA2629478A1 (en) | 2007-05-18 |
| AU2006313724A1 (en) | 2007-05-18 |
| AU2006313724B2 (en) | 2010-12-23 |
| RU2008123382A (ru) | 2009-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20131114 |