ES2524331T3 - Ésteres del ácido betulónico y derivados del polialquilenglicol y el ácido betulónico para el tratamiento de infección viral y cáncer - Google Patents
Ésteres del ácido betulónico y derivados del polialquilenglicol y el ácido betulónico para el tratamiento de infección viral y cáncer Download PDFInfo
- Publication number
- ES2524331T3 ES2524331T3 ES07712472.5T ES07712472T ES2524331T3 ES 2524331 T3 ES2524331 T3 ES 2524331T3 ES 07712472 T ES07712472 T ES 07712472T ES 2524331 T3 ES2524331 T3 ES 2524331T3
- Authority
- ES
- Spain
- Prior art keywords
- cells
- rpmi
- betulonic acid
- unsubstituted
- alkenyl
- 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.)
- Active
Links
- SLJTWDNVZKIDAU-SVAFSPIFSA-N Betulonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C SLJTWDNVZKIDAU-SVAFSPIFSA-N 0.000 title 2
- SLJTWDNVZKIDAU-CKURCAGRSA-N Betulonic acid Natural products CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O SLJTWDNVZKIDAU-CKURCAGRSA-N 0.000 title 2
- 206010028980 Neoplasm Diseases 0.000 title 1
- 208000036142 Viral infection Diseases 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 229920001515 polyalkylene glycol Polymers 0.000 title 1
- 230000009385 viral infection Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000004122 cyclic group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004419 alkynylene group Chemical group 0.000 abstract 1
- 125000005018 aryl alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 26
- 102000004882 Lipase Human genes 0.000 description 11
- 108090001060 Lipase Proteins 0.000 description 11
- 239000004367 Lipase Substances 0.000 description 11
- 235000019421 lipase Nutrition 0.000 description 11
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 101710084373 Lipase 1 Proteins 0.000 description 2
- 239000006143 cell culture medium Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Un compuesto que tiene la estructura (I), (II) o (2b):**Fórmula** en donde R es un grupo alquilo, alquenilo, alquinilo, arilo, arilalquilo, arilalquenilo, arilalquinilo, alquilarilo, alquenilarilo o alquinilarilo, que opcionalmente puede incluir uno o más heteroátomos de N, O o S en su esqueleto de carbono, y que opcionalmente puede incluir uno o más grupos -CO- en su esqueleto de carbono, siempre y cuando R comprenda un sistema de anillo fusionado, en donde el sistema de anillo fusionado tiene una estructura de esterano como se muestra:**Fórmula** que puede comprender uno o más enlaces dobles; R y/o el sistema de anillo fusionado opcionalmente puede ser sustituido con uno o más de -F, -Cl, -Br, -I, -CF3, -CCl3, - CBr3, -CI3, -OH, -SH, -NH2, -CN, -NO2, -COOH, -R1-O-R2, -R1-S-R2, -R1-SO-R2, -R1-SO2-R2, -R1-SO2-OR2, -R1O-SO2-R2, -R1- SO2-N(R2)2, -R1-NR2-SO2-R2, -R1O-SO2-OR2, -R1O-SO2-N(R2)2, -R1-NR2-SO2-OR2, -R1-NR2-SO2-N(R2)2, -R1-N(R2)2, -R1- N(R2)3 +, -R1-P(R2)2,- R1-Si(R2)3, -R1-CO-R2, -R1-CO-OR2, -R1O-CO-R2, -R1-CO-N(R2)21 -R1-NR2-CO-R2, -R1O-CO-OR2, -R1OCO- N(R2)2, -R1-NR2-CO-OR2, -R1-NR2-CO-N(R2)2, -R1-CS-R2, -R1-CSOR2, -R1O-CS-R2, -R1-CS-N(R2)2, -R1-NR2-CS-R2, - R1O-CS-OR2, -R1O-CS-N(R2)2, -R1-NR2-CS-OR2, -R1-NR2-CS-N(R2)2 o -R2; - R1- es independientemente un enlace químico, un grupo alquileno C1-10, alquenileno C1-10 o alquinileno C1-10; - R2 es independientemente hidrógeno, alquilo C1-6 no sustituido, alquenilo C1-6 no sustituido, alquinilo C1-6 no sustituido o arilo C6-10 no sustituido; y cualquier grupo alquilo, alquenilo o alquinilo puede ser de cadena lineal o ramificada, o tener o incluir uno o más grupos cíclicos.
Description
Se siguió el siguiente protocolo:
En el día 0: Se preparó una placa multi-pozos por voluntario, que comprende cada una 0.5 x 106 células/pozo en un volumen total de 1.5 ml. Se adicionaron las células, RPMI (medio de cultivo celular), PHA, lipasa y el compuesto de ensayo 5 4a-p de acuerdo con la tabla 5 (todos los experimentos se hicieron por triplicado). El compuesto de ensayo disuelto en RPMI se adicionó en las siguientes cantidades: 125 Jl = 0.5 mM y 250 Jl = 1 mM.
10
- Placa
- Voluntario 1 (JCL) Voluntario 2 (SVT) Voluntario 3 (JMB)
- 1 (control)
- 1 Jl células + 500 Jl RPMI 1 Jl células + 500 Jl RPMI 1 Jl células + 500 Jl RPMI
- 2 (control)
- 1 Jl células + 450 Jl RPMI + 50 Jl PHA 1 Jl células + 450 Jl RPMI + 50 Jl PHA 1 Jl células + 450 Jl RPMI + 50 Jl PHA
- 3
- 1 Jl células + 375 Jl RPMI + 125 Jl compuesto 4a-p 1 Jl células + 375 Jl RPMI + 125 Jl compuesto 4a-p 1 Jl células + 375 Jl RPMI + 125 Jl compuesto 4a-p
- 4
- 1 Jl células + 250 Jl RPMI + 250 Jl compuesto 4a-p 1 Jl células + 250 Jl RPMI + 250 Jl compuesto 4a-p 1 Jl células + 250 Jl RPMI + 250 Jl compuesto 4a-p
- 5 (control)
- 1 Jl células + 470 Jl RPMI + 30 Jl lipasa 1 Jl células + 470 Jl RPMI + 30 Jl lipasa 1 Jl células + 470 Jl RPMI + 30 Jl lipasa
- 6 (control)
- 1 Jl células + 420 Jl RPMI + 30 Jl lipasa + 50 Jl PHA 1 Jl células + 420 Jl RPMI + 30 Jl lipasa + 50 Jl PHA 1 Jl células + 420 Jl RPMI + 30 Jl lipasa + 50 Jl PHA
- 7
- 1 Jl células + 345 Jl RPMI + 30 Jl lipasa + 125 Jl compuesto 4a-p 1 Jl células + 345 Jl RPMI + 30 Jl lipasa + 125 Jl compuesto 4a-p 1 Jl células + 345 Jl RPMI + 30 Jl lipasa + 125 Jl compuesto 4a-p
- 8
- 1 Jl células + 220 Jl RPMI + 30 Jl lipasa + 250 Jl compuesto 4a-p 1 Jl células + 220 Jl RPMI + 30 Jl lipasa + 250 Jl compuesto 4a-p 1 Jl células + 220 Jl RPMI + 30 Jl lipasa + 250 Jl compuesto 4a-p
En el día 1:
- 2 x 500 Jl fueron tomadas de cada pozo de la placa 1 y se colocaron en un pozo de las placas de 2 y 3. 15 - Placa 2: las células fueron tritiadas con 3H-timidina durante 4 horas; después de 4 horas de incubación en presencia de
radioactividad, la placa 2 se recogió y se contó la radioactividad.
- Placa 1: se adicionaron 50 Jl de PHA a los 500 Jl de cada pozo de la placa 1.
20 En el día 2:
- Placa 1: las células fueron tritiadas con 3H-timidina durante 4 horas; después de 4 horas de incubación en presencia de radioactividad,
- la placa 1 se recogió y se contó la radioactividad.
- Placa 3: células fueron tritiadas con 3H-timidina durante 4 horas; después de 4 horas de incubación en presencia de 25 radioactividad, la placa 3 se recogió y se contó la radioactividad.
Los resultados experimentales se resumen en las Figuras 5a-c y 6a-c.
45
Claims (1)
-
imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 imagen7 imagen8 imagen9 imagen10 imagen11 imagen12 imagen13 imagen14
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0604535.5A GB0604535D0 (en) | 2006-03-07 | 2006-03-07 | Betulonic acid derivatives |
| GB0604535 | 2006-03-07 | ||
| PCT/EP2007/052154 WO2007101873A2 (en) | 2006-03-07 | 2007-03-07 | Betulonic acid esters and betulinic acid polyalkylene-glycol derivatives for the treatment of viral infection and cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2524331T3 true ES2524331T3 (es) | 2014-12-05 |
Family
ID=36219262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07712472.5T Active ES2524331T3 (es) | 2006-03-07 | 2007-03-07 | Ésteres del ácido betulónico y derivados del polialquilenglicol y el ácido betulónico para el tratamiento de infección viral y cáncer |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8586569B2 (es) |
| EP (1) | EP1999139B1 (es) |
| DK (1) | DK1999139T3 (es) |
| ES (1) | ES2524331T3 (es) |
| GB (1) | GB0604535D0 (es) |
| WO (1) | WO2007101873A2 (es) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2260052A4 (en) | 2008-02-26 | 2013-01-16 | Univ Emory | STEROIDANALOGA FOR NEUROPROTEKTION |
| KR100941595B1 (ko) | 2008-06-05 | 2010-02-11 | 주식회사 알앤엘바이오 | 바이러스 억제제로서 유용한 트리테르페노이드계 화합물 |
| CZ301158B6 (cs) * | 2008-09-01 | 2009-11-18 | Univerzita Karlova v Praze, Prírodovedecká fakulta | Deriváty triterpenoidu pro lécbu nádorových onemocnení a farmaceutická kompozice je obsahující |
| PL2335675T3 (pl) | 2009-12-10 | 2015-08-31 | Neubourg Skin Care Gmbh & Co Kg | Wolne od emulgatorów, stabilizowane polimerem formulacje pianki |
| US9238815B2 (en) | 2009-12-11 | 2016-01-19 | Icahn School of Medicine at Mounta Sinai | Compositions and methods for inhibiting human host factors required for influenza virus replication |
| US8435972B2 (en) * | 2010-09-02 | 2013-05-07 | Emory University | Method for the treatment of central nervous system cancers and compositions related thereto |
| CN102167720B (zh) * | 2011-03-11 | 2012-11-14 | 华东师范大学 | 抑制破骨细胞分化的桦木酮酸衍生物及其制备和应用 |
| US8633178B2 (en) | 2011-11-23 | 2014-01-21 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US20130338122A1 (en) | 2012-06-18 | 2013-12-19 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| WO2014071507A1 (en) * | 2012-11-09 | 2014-05-15 | Bioniche Life Sciences Inc. | Plant compositions and methods and uses thereof for treating elevated glucocorticoid related disorders, and anxiety |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| EP3145489A1 (en) | 2014-05-22 | 2017-03-29 | TherapeuticsMD, Inc. | Natural combination hormone replacement formulations and therapies |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| WO2017173044A1 (en) | 2016-04-01 | 2017-10-05 | Therapeuticsmd Inc. | Steroid hormone compositions in medium chain oils |
| WO2017173071A1 (en) | 2016-04-01 | 2017-10-05 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
| US10729735B1 (en) | 2016-09-14 | 2020-08-04 | Phoenix Biotechnology, Inc. | Method and compostitions for treating coronavirus infection |
| US10702567B2 (en) | 2016-09-14 | 2020-07-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infection |
| US10596186B2 (en) | 2016-09-14 | 2020-03-24 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infections |
| MX2020002884A (es) | 2017-09-14 | 2020-10-05 | Phoenix Biotechnology Inc | Método y composición neuroprotectora mejorada para tratar afecciones neurológicas. |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| KR20220151038A (ko) | 2020-03-31 | 2022-11-11 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 예방를 위한 조성물 |
| US11806359B2 (en) | 2020-03-31 | 2023-11-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating Coronavirus infection |
| US20240262860A1 (en) * | 2020-07-07 | 2024-08-08 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pentacyclic triterpenoid glycoside compound, and preparation method therefor and use thereof |
| CN114848652A (zh) * | 2022-05-31 | 2022-08-05 | 澳门大学 | 白桦脂醛在制备用于预防或治疗神经退行性疾病的药物中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6403816B1 (en) * | 1997-09-30 | 2002-06-11 | Dabur Research Foundation | Betulinic acid derivatives having antiangiogenic activity, processes for producing such derivatives and their use for treating tumor associated angiogenesis |
| US6670345B1 (en) * | 1997-09-30 | 2003-12-30 | Dabur Research Foundation | Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid |
| WO2000046235A1 (en) * | 1998-11-18 | 2000-08-10 | Dabur Research Foundation | Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors |
| ATE267837T1 (de) * | 1999-09-09 | 2004-06-15 | Dabur Res Foundation | Betulinsäure-derivate mit antiangiogener wirkung, verfahren zur herstellung solcher derivate und deren verwendung für die behandlung tumorassoziierter angiogenese |
| AU8494601A (en) * | 2000-08-18 | 2002-03-04 | Univ Illinois | Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV |
-
2006
- 2006-03-07 GB GBGB0604535.5A patent/GB0604535D0/en not_active Ceased
-
2007
- 2007-03-07 DK DK07712472.5T patent/DK1999139T3/en active
- 2007-03-07 WO PCT/EP2007/052154 patent/WO2007101873A2/en not_active Ceased
- 2007-03-07 ES ES07712472.5T patent/ES2524331T3/es active Active
- 2007-03-07 EP EP07712472.5A patent/EP1999139B1/en active Active
-
2008
- 2008-09-04 US US12/204,354 patent/US8586569B2/en active Active
-
2013
- 2013-11-08 US US14/075,093 patent/US9303058B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9303058B2 (en) | 2016-04-05 |
| EP1999139B1 (en) | 2014-08-20 |
| WO2007101873A2 (en) | 2007-09-13 |
| GB0604535D0 (en) | 2006-04-12 |
| US20140066416A1 (en) | 2014-03-06 |
| US20090068257A1 (en) | 2009-03-12 |
| EP1999139A2 (en) | 2008-12-10 |
| US8586569B2 (en) | 2013-11-19 |
| DK1999139T3 (en) | 2014-12-01 |
| WO2007101873A3 (en) | 2008-01-17 |
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