HUE033401T2 - Új 5-fluor-uracil-származék - Google Patents
Új 5-fluor-uracil-származék Download PDFInfo
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- HUE033401T2 HUE033401T2 HUE10826686A HUE10826686A HUE033401T2 HU E033401 T2 HUE033401 T2 HU E033401T2 HU E10826686 A HUE10826686 A HU E10826686A HU E10826686 A HUE10826686 A HU E10826686A HU E033401 T2 HUE033401 T2 HU E033401T2
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- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical class FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 title description 71
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 amino, benzoyl Chemical group 0.000 claims description 59
- 206010028980 Neoplasm Diseases 0.000 claims description 52
- 238000012360 testing method Methods 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 201000011510 cancer Diseases 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
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- 125000004429 atom Chemical group 0.000 claims description 7
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- 102100037214 Orotidine 5'-phosphate decarboxylase Human genes 0.000 description 15
- 108010055012 Orotidine-5'-phosphate decarboxylase Proteins 0.000 description 15
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- 102100022334 Dihydropyrimidine dehydrogenase [NADP(+)] Human genes 0.000 description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 12
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
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- 239000003814 drug Substances 0.000 description 12
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 12
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- 229940079593 drug Drugs 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- ZPLQIPFOCGIIHV-UHFFFAOYSA-N Gimeracil Chemical compound OC1=CC(=O)C(Cl)=CN1 ZPLQIPFOCGIIHV-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 9
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- CSGQJHQYWJLPKY-UHFFFAOYSA-N CITRAZINIC ACID Chemical compound OC(=O)C=1C=C(O)NC(=O)C=1 CSGQJHQYWJLPKY-UHFFFAOYSA-N 0.000 description 8
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- OBPLXMXAULXZHN-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;5-fluoro-1h-pyrimidine-2,4-dione Chemical compound FC1=CNC(=O)NC1=O.OC(=O)C1=CC=CC(C(O)=O)=C1 OBPLXMXAULXZHN-UHFFFAOYSA-N 0.000 description 8
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- WTSKMKRYHATLLL-UHFFFAOYSA-N (6-benzoyloxy-3-cyanopyridin-2-yl) 3-[3-(ethoxymethyl)-5-fluoro-2,6-dioxopyrimidine-1-carbonyl]benzoate Chemical compound O=C1N(COCC)C=C(F)C(=O)N1C(=O)C1=CC=CC(C(=O)OC=2C(=CC=C(OC(=O)C=3C=CC=CC=3)N=2)C#N)=C1 WTSKMKRYHATLLL-UHFFFAOYSA-N 0.000 description 7
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- KUMNAYAGASSDLP-UHFFFAOYSA-N [5-chloro-2-[3-[3-(ethoxymethyl)-5-fluoro-2,6-dioxopyrimidine-1-carbonyl]benzoyl]oxypyridin-4-yl] 2,6-bis(cyclopentanecarbonyloxy)pyridine-4-carboxylate Chemical compound O=C1N(COCC)C=C(F)C(=O)N1C(=O)C1=CC=CC(C(=O)OC=2N=CC(Cl)=C(OC(=O)C=3C=C(OC(=O)C4CCCC4)N=C(OC(=O)C4CCCC4)C=3)C=2)=C1 KUMNAYAGASSDLP-UHFFFAOYSA-N 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- GCRNGPNGNJSZCC-UHFFFAOYSA-N tert-butyl 3-amino-3a,4,6,6a-tetrahydro-1h-pyrrolo[3,4-c]pyrazole-5-carboxylate Chemical compound N1N=C(N)C2CN(C(=O)OC(C)(C)C)CC21 GCRNGPNGNJSZCC-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (4)
- ί, Az alábbi 0' ) képtetö 5·fluor-untcil·származékot: vagy «/.ok sónf Ï $ «hol R msemévé hidmgmuíosn mse,} hiórovu -topon uwi *opotí?u, R u iemvm t ' e{.mtKs 'agy elágazó láncú askoxv-C';..,, egyenes vag> elágazó lasmn -aîkilcsopon vagy mír&hmromrn-· nslesoporí. X jelentése szénatom sage nmogenatmo, es V jelem cm' h-tk--géruUím vagy eismocsssspoft; ahol a hidroaiesoport véddesoportját az alábbiakból allô csoportból választjuk: aeiiess|gppfe C>.·' egyenes vagy elágazó láncú alkoxbkashotúlmsopnrtok; CV& alksi csoporttal mono- vagy dtszubsztituálí karbamoilcsoporiük; szubsztuuált vagy szuhsztituálatlao Cm; i|yóils vágy V. >. tzo V tests a kdo'.ofw ov t ^eesvrse,m. ,as eaxaee'á w ummhCMmostok muhmohak vagy szubszútnáknlan henzilesoport, benzhkiólesopon vagy trrtücsoporí; szüli védócsopoctok; es ammnsav maradékok, ahol az «alcsoportokat az alábbiakból illó osópitbók yólasztjnki yznbáilitnalt vagy szttószlltssáknktn -, „ -, abus auksopmtek, \ njAmtstoaH s*.*gx mahvuomksilan. bmvosíCM.mmi n-rnüloilesopon, sags BmcdloikNopoh é,\ CV.,, dUovükU-karbonibesopotlok. alun a *m,omMuáH tht'm ,m;A«opoKok xagx a vabsrtUt^t^n^ilesoportyc^lsÄil^ö]^^ vagy ß-naftoilcsoport szub&zîitmnsei a C>^ egyenes vagy elágázó láitcó alillesopóil., a C^: egyenes vagy' elágazó láncú alkoxiesoport, a halogénatom, a és a .:|aÉ9^í^óióT|: közül választón 3*3 szobszótucns; áltól a s/ubs/htuák C^t egyenes vagy elágazó láncú alkliesonori szubszütucoseit 1-3, az alábbiakból álló csoportból választott,, szuhsziimens képezi: halogénatom és Ch^ lineáris vagy elágazó 1 even «Ikoxiesogest, aim; s sznkszíítualt best né söpört, besv/kidnlcMspoft \ ,-,ζ s -rmk sec, cl omovousenmn : -5 «/ alábbiakból álló csoportból választott, szabsz.?keens képezi; €>,* egyenes vagy elágazó láncú afküesmmu, Cí.\ egyenes sags elágazó loree alko^'c^opett. halogénatom, ntíFOOso'Vít e,\ cianocsepork és ahol a sziliI védocsoportokat az alábbiakból álló csoportból választjuk: trisnetü-szihb *csopon, tsrt-butd Psnsetd'szülhesssport, mess: -dm epropd-vnüK-eport, trumpropibszxm "Csoport, reiT^Iseoptxvp?I*d^*p<>rt cs difotiI * merii-szilií -csoport 3,: Λζ ! igénypont szerinti fi) képiíífea a.?, alábbi képiéül csoport:<C,C Pi-Ό *.gX ^f%Ct\C ' » keck*, Cn >o tállok W- pléotése bt#ó|É8iiÖ%. âîltleàoport, vagy bcnzik&oporu amely ^ziíbaklkéglilMg vagy az áilbbiakből âllé.ssoponbêl. válaszúm 1-5 szubsztiutemse! sznbsztituáli: Cigi ëgÿeMs vagy eiágazé lánei siliicsopon:, €$.$ egyenes yggy élágggp íáoeő aikoxics^porg itÉpesoporí os cianocsoport; egy következő kèpletô csoport:egy következő képleté csoport:ahol Rf jelentése líklrogeaaovo, abikwoeenü vap> henzilesopon. amek szubs/tbuaialkm vagy zz alábbiakból álló csoportbő! válaldelt 1-5 s/obsztituensael ézöbsztiíoált: €>.* Őgyétíekvógy elagazo láncú dkilcsopory * V, ebenes ekga/o Laten alkextesoporL hslo^naíoro, nhroesoport ős ctanoesoporő vagy egy következő képlett! csoport;|. Az I. vagy 2. igénypo# szerinti 5''fltior^ra«fN«ármazék vagy állnak sója, afel Íz pífniiSP hidrogénatom, aflieAopork henzilosopott, aUíös seilcsopprt, aromás Mlfcüprí;· fagy- nlictklusos aeilcsoprk R3 jelentése kis szciiatomszáJtm ilkökibmetíl· -csoport,, ahol a kís$zéii«tom*2ámü atkgzíesogert ! -6 sæna&#&$ -mgy voahiKvinntt kapott \ o^mk \ enmo^ no^eoaumn λ1) > ca os loot - or vag}· klóratom. 4 V ' 2 !„οιη\ν ok ht tvAtv. n^p s f "»cuks - <»n x»es "arp ónnak pia, ahol |1' jflppiép hidrogénatom. henziíeseport. acetíksoport, propiomksoport:, IgobutirilcsoppÉppt^Éptksoport, henzoiicsoport, p-klór-heoaxnl'.. vagy eiklogentánékarhomk c\opox„ k .JedCNt vo '-x or om-oan ,> akoM net, <,-όρο" a no' a k^n <oiíom\'<nm âlkoÂPpakî ki ;iitot08ú%' % jöléi&k t&ê»atom vagy nitrogénatom, és Y jelentése fi untatom vagy klóratom.
- 5, Sm. M* igéttypomok bármelyike szerinti S-'tluor-oracIkszarmaaik vagy annak: sója, áltól E* jpléitlp hldfogÉtaiüio vagy acetilesopon, R* jelentése kis száiapnnszápra ai koz Rimái besöpört, ahol a klssaéothnmszámö alkoxksopnri 1-6 saépaîomoâ, 3f jélintése szénatom vagy nitrogénatom, ès Y jelentése klóratom,
- 6. Az 1-5, igénypontok bármelyike szerinti S-Haor-ur^íl-származek vagy ararak gőfá. ahol R! jelentése hidrogénatom vagy acél besöpört, 14' jelentése kis szetudomszámú Slkoxi-meti l-csoport* ahol a kíss/énatomszámü dfcoxksoposi ki széna tömör, X s döntése szénatom, és Y jelentése klóralom. ?.. Az 1 X rgu'weiok Knmehke sxeo m ^ t uot oumn-szannazrl \ xgy annak 44, ahol R' jelentive hidrogénatom vagy aceii lesöpört R' jelentése etoxi-metil-vV'port, \ oo-utoo, - V .torn 1. > ’t lekntese dOramm !„ Gsogyszcr, amely az. 1-7. igénypontok bármelyike szerinti S-iluor-wiélE dztetrazilot vagy annak sóját hatóanyagként tartalmazza. f. Fontot ebem a et, aok.s az 'Ά ígcoxpornok íxat.vbike -.zent, fűm :*ÖÄ bsMrntazékt>t vag> annak sóiét hatóanyaóként tartalmazza. 10, Λ 9. igénypont szerinti tumor elleni szer, ahol a íi\MM éllélij IljÉSft.; a& alábbiakból álló csoportból választott legalább egy rákos megbetegedés kezelésére alkalmazzák: fej- és nyakrákok, nyelőcsői tikok, gyomorrakok, vastaghélrákok, véghélrákok. májrákok, epehólyag- és epevezetékrákok, eperends/errákok. hasnyámirigyfákt^Andórákok, mellrákok, pete-fészekr tikok, mchnyakrakok, m e h ny a 1 k ahàrt y arák ok, veserákok, hólyagrákok. posziaiarákok,, Ikrétimkrók ©sent és lágy szövet szajkóiba, leukémia, fóssaiklalMű tafömálg nnéitfm mgklpbjg bdrrâkakj agyiösmígky ©s mellhâAyAkkok. ! k Az I··?, igéögpakok Msiiflyiké szeriről S^CIáo^aíBdkszámiazkk vagy aguak sója ilkilAmááása,
- 12, Az l··?, IgihiypouHA bármelyik© szerimi 5-ÍíuüjmracH-^énnazék vagy aeaak sgláask alkatoaaása t»mft fllfni »r ©J©áliiMísára.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009246400 | 2009-10-27 |
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| Publication Number | Publication Date |
|---|---|
| HUE033401T2 true HUE033401T2 (hu) | 2017-11-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE10826686A HUE033401T2 (hu) | 2009-10-27 | 2010-10-26 | Új 5-fluor-uracil-származék |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8889699B2 (hu) |
| EP (1) | EP2495243B1 (hu) |
| JP (1) | JP5008778B2 (hu) |
| KR (1) | KR101441770B1 (hu) |
| CN (1) | CN102574837B (hu) |
| AU (1) | AU2010312594B2 (hu) |
| DK (1) | DK2495243T3 (hu) |
| ES (1) | ES2619937T3 (hu) |
| HK (1) | HK1168344A1 (hu) |
| HR (1) | HRP20170406T1 (hu) |
| HU (1) | HUE033401T2 (hu) |
| PL (1) | PL2495243T3 (hu) |
| PT (1) | PT2495243T (hu) |
| RU (1) | RU2503673C2 (hu) |
| TW (1) | TWI481604B (hu) |
| WO (1) | WO2011052554A1 (hu) |
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| CN105294575A (zh) * | 2015-12-03 | 2016-02-03 | 常州工程职业技术学院 | 一种乳清酸甲酯的制备方法 |
| WO2018008761A1 (ja) * | 2016-07-08 | 2018-01-11 | Ｙａｎｃｈｅｒｓ株式会社 | 固形癌治療剤 |
| EP3684408A1 (en) | 2017-09-19 | 2020-07-29 | Massachusetts Institute of Technology | Compositions for chimeric antigen receptor t cell therapy and uses thereof |
| KR20210068478A (ko) | 2018-09-28 | 2021-06-09 | 메사추세츠 인스티튜트 오브 테크놀로지 | 콜라겐-국재화된 면역조정성 분자 및 그의 방법 |
| JP7363805B2 (ja) | 2018-11-12 | 2023-10-18 | 株式会社レゾナック | オロト酸誘導体の製造方法 |
| WO2020263399A1 (en) | 2019-06-26 | 2020-12-30 | Massachusetts Institute Of Technology | Immunomodulatory fusion protein-metal hydroxide complexes and methods thereof |
| WO2021061648A1 (en) | 2019-09-23 | 2021-04-01 | Massachusetts Institute Of Technology | Methods and compositions for stimulation of endogenous t cell responses |
| WO2021183207A1 (en) | 2020-03-10 | 2021-09-16 | Massachusetts Institute Of Technology | COMPOSITIONS AND METHODS FOR IMMUNOTHERAPY OF NPM1c-POSITIVE CANCER |
| CN115768464A (zh) | 2020-03-10 | 2023-03-07 | 麻省理工学院 | 产生工程化记忆样nk细胞及其组合物的方法 |
| WO2021221782A1 (en) | 2020-05-01 | 2021-11-04 | Massachusetts Institute Of Technology | Chimeric antigen receptor-targeting ligands and uses thereof |
| CN112940152B (zh) * | 2021-01-31 | 2022-06-14 | 宁夏医科大学 | 5-氟尿嘧啶-1-甲氧羧烷基型环糊精衍生物及其制备方法 |
| WO2022208784A1 (ja) * | 2021-03-31 | 2022-10-06 | Ｄｅｌｔａ－Ｆｌｙ Ｐｈａｒｍａ株式会社 | 湿度に敏感な医薬用途物質を安定化する方法及び安定製剤 |
| TWI810543B (zh) * | 2021-03-31 | 2023-08-01 | 日商德爾塔菲製藥股份有限公司 | 使對濕度敏感之醫藥用途物質穩定化之方法及穩定製劑 |
| WO2023081715A1 (en) | 2021-11-03 | 2023-05-11 | Viracta Therapeutics, Inc. | Combination of car t-cell therapy with btk inhibitors and methods of use thereof |
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| SU574155A3 (ru) * | 1973-11-28 | 1977-09-25 | Мицуи Фармасьютикалз "Инкорпорейтед" (Фирма) | Способ получени 1-ацил-5-фторурацила |
| EP0323441B1 (en) * | 1984-10-30 | 1996-04-24 | Otsuka Pharmaceutical Co., Ltd. | 5-Fluorouracil derivatives |
| JPS63301880A (ja) * | 1985-09-03 | 1988-12-08 | Otsuka Pharmaceut Co Ltd | ５−フルオロウラシル誘導体 |
| EP0247381B1 (en) * | 1986-04-30 | 1993-08-04 | Otsuka Pharmaceutical Co., Ltd. | 5-flurorouracil derivatives |
| JPS63201127A (ja) * | 1987-02-17 | 1988-08-19 | Otsuka Pharmaceut Co Ltd | ５−フルオロウラシル誘導体を含有する制癌剤 |
| DK169520B1 (da) * | 1986-07-25 | 1994-11-21 | Otsuka Pharma Co Ltd | 5-fluoruracilderivater, fremgangsmåde til deres fremstilling, anticancerpræparat indeholdende et sådant derivat og anvendelse af et sådant derivat til fremstilling af et præparat til behandling af cancer |
| JP2706666B2 (ja) | 1987-07-31 | 1998-01-28 | 大鵬薬品工業株式会社 | ２’−デオキシ−５−フルオロウリジン誘導体及びその塩 |
| JP2700263B2 (ja) | 1988-12-16 | 1998-01-19 | 大塚製薬株式会社 | ５―フルオロウラシル誘導体の製造法 |
| US5047581A (en) * | 1989-08-25 | 1991-09-10 | Fmc Corporation | Isolation of cis-isomers from isomeric mixtures of cis/transcyclopropanecarboxylates |
| DE122011100040I2 (de) | 1991-05-27 | 2012-08-09 | Taiho Pharmaceutical Co Ltd | Zusammensetzung, verfahren und instrument zur potenzierung der antitumoraktivitat und zur behandlungvon tumoren. |
| JPH0580451A (ja) | 1991-09-19 | 1993-04-02 | Fuji Photo Film Co Ltd | レーザー露光用ハロゲン化銀写真感光材料及びその処 理方法 |
| RU2165761C1 (ru) * | 2000-06-05 | 2001-04-27 | Уральский научно-исследовательский институт фтизиопульмонологии | Способ лечения экспериментального туберкулеза |
| WO2005074029A1 (ja) | 2004-01-28 | 2005-08-11 | Matsushita Electric Industrial Co., Ltd. | モジュール及びこれを用いた実装構造体 |
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| Publication number | Publication date |
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| TWI481604B (zh) | 2015-04-21 |
| JP5008778B2 (ja) | 2012-08-22 |
| KR101441770B1 (ko) | 2014-09-17 |
| JPWO2011052554A1 (ja) | 2013-03-21 |
| DK2495243T3 (en) | 2017-03-27 |
| WO2011052554A1 (ja) | 2011-05-05 |
| AU2010312594B2 (en) | 2013-06-20 |
| US8889699B2 (en) | 2014-11-18 |
| CN102574837A (zh) | 2012-07-11 |
| TW201121953A (en) | 2011-07-01 |
| EP2495243A4 (en) | 2015-01-14 |
| KR20120083492A (ko) | 2012-07-25 |
| HRP20170406T1 (hr) | 2017-04-21 |
| ES2619937T3 (es) | 2017-06-27 |
| RU2503673C2 (ru) | 2014-01-10 |
| AU2010312594A1 (en) | 2012-04-12 |
| RU2012110380A (ru) | 2013-09-27 |
| HK1168344A1 (en) | 2012-12-28 |
| CN102574837B (zh) | 2013-11-27 |
| US20120232103A1 (en) | 2012-09-13 |
| PT2495243T (pt) | 2017-03-13 |
| EP2495243B1 (en) | 2016-12-28 |
| PL2495243T3 (pl) | 2017-07-31 |
| EP2495243A1 (en) | 2012-09-05 |
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