AR090955A1 - Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vih - Google Patents
Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vihInfo
- Publication number
- AR090955A1 AR090955A1 ARP130101545A ARP130101545A AR090955A1 AR 090955 A1 AR090955 A1 AR 090955A1 AR P130101545 A ARP130101545 A AR P130101545A AR P130101545 A ARP130101545 A AR P130101545A AR 090955 A1 AR090955 A1 AR 090955A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- coor2
- substituted
- nr2so2r3
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compuestos que tienen propiedades farmacológicas y que afectan el aspecto biológico, sus composiciones farmacéuticas y métodos de uso. En particular, las aminas bicíclicas C-17 de triterpenoides que tienen una actividad antiviral única se proveen como inhibidores de la maduración del VIH. Estos compuestos son útiles para el tratamiento del VIH y del SIDA. Reivindicación 1: Un compuesto, que incluye sales de este aceptables desde el punto de vista farmacéutico, caracterizado porque se selecciona del grupo de: un compuesto de la fórmula (1); un compuesto de la fórmula (2); y un compuesto de la fórmula (3); en donde R¹ es isopropenilo o isopropilo; J y E son, cada uno, independientemente -H o -CH₃, y E está ausente cuando el enlace doble está presente; X se selecciona del grupo de fenilo, anillo heteroarilo, anillo cicloalquilo C₄₋₈, cicloalquenilo C₄₋₈, spirocicloalquilo C₄₋₉, spirocicloalquenilo C₄₋₉, oxacicloalquilo C₄₋₈, dioxacicloalquilo C₄₋₈, oxacicloalquenilo C₆₋₈, dioxacicloalquenilo C₆₋₈, ciclodialquenilo C₆, oxaciclodialquenilo C₆, oxaspirocicloalquilo C₆₋₉ y oxaspirocicloalquenilo C₆₋₉; X también se puede seleccionar del grupo que consiste en los compuestos del grupo de fórmulas (4); y para los compuestos de las fórmulas (2) y (3), X también puede ser el compuesto de fórmula (5); en donde X se sustituye con A, y A es al menos un miembro seleccionado del grupo de -H, -halo, -hidroxilo, -alquilo C₁₋₆, -alcoxi C₁₋₆, -haloalquilo C₁₋₆, -NR²R², -COOR², -C(O)NR²R², -C(O)NR²SO₂R³, -SO₂NR²R², -NR²SO₂R², -SO₂NR²R², -cicloalquil C₁₋₆-COOR², -alquenil C₂₋₆-COOR², -alquinil C₂₋₆-COOR², -alquil C₁₋₆-COOR², -NHC(O)(CH₂)ₙ-COOR², -SO₂NR²C(O)R², -tetrazol y heteroaril-COOR² bicíclico; Y se selecciona del grupo de -COOR², -C(O)NR²SO₂R³, -C(O)NHSO₂NR²R², -NR²SO₂R³, -SO₂NR²R², -cicloalquil C₃₋₆-COOR², -alquenil C₂₋₆-COOR², -alquinil C₂₋₆-COOR², -alquil C₁₋₆-COOR², -NHC(O)(CH₂)ₙ-COOR², -SO₂NR²C(O)R², -tetrazol y -CONHOH; en donde n = 1 - 6; W es -CH₂ o -CO; Z se selecciona del grupo que consiste en los compuestos del grupo de fórmulas (6); V se selecciona del grupo de -CR⁸R⁹-, -SO₂-, -O- y -NR¹⁰-; U se selecciona del grupo de -CR⁸R⁹-, -SO₂- y -NR¹⁰-; M se selecciona del grupo de -CHR⁸R⁹, -SO₂R⁴, -SO₂NR³R³, -OH y -NR¹⁰R¹¹-; R² es -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo o alquilo C₁₋₆ sustituido con -arilo; R³ es -alquilo C₁₋₆ o alquilo C₁₋₆ sustituido con -alquilo; R⁴ se selecciona del grupo de -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -cicloalquilo C₃₋₆, -arilo y -heteroarilo; R⁵ se selecciona del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo y -alquilo C₁₋₆-OH; R⁶ y R⁷ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -CO₂R², -CH₂OH, -CHF₂ y -CF₃; R⁸ y R⁹ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -SO₂R³, -SO₂NR²R² o -OH, -NR²R², -NR²SO₂R³, -NR²COR³ y -NR²CONR²R²; siempre que solo uno de R⁸ y R⁹ se puedan seleccionar del grupo de -OH, -NR²R², -NR²SO₂R³, -NR²COR³ y -NR²CONR²R²; y R¹⁰ y R¹¹ se seleccionan, cada uno, independientemente del grupo de -H, -alquilo C₁₋₆, alquilo C₁₋₆ sustituido con -alquilo, -alquil C₁₋₃arilo, alquil C₁₋₃heteroarilo, -CO₂R² y -SO₂R³; siempre que solo uno de R¹⁰ y R¹¹ se pueda seleccionar del grupo de -COR² o -SO₂R³.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261643483P | 2012-05-07 | 2012-05-07 | |
US13/799,479 US8889854B2 (en) | 2012-05-07 | 2013-03-13 | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
Publications (1)
Publication Number | Publication Date |
---|---|
AR090955A1 true AR090955A1 (es) | 2014-12-17 |
Family
ID=49513043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP130101545A AR090955A1 (es) | 2012-05-07 | 2013-05-06 | Aminas biciclicas c-17 de triterpenoides con actividad inhibidora de la maduracion del vih |
Country Status (17)
Country | Link |
---|---|
US (1) | US8889854B2 (es) |
EP (1) | EP2847208B1 (es) |
JP (1) | JP6212545B2 (es) |
KR (1) | KR20150013157A (es) |
CN (1) | CN104540844B (es) |
AR (1) | AR090955A1 (es) |
AU (1) | AU2013259894B2 (es) |
BR (1) | BR112014027669A2 (es) |
CA (1) | CA2872891C (es) |
EA (1) | EA027133B1 (es) |
ES (1) | ES2652510T3 (es) |
IL (1) | IL235465A (es) |
MX (1) | MX354914B (es) |
PT (1) | PT2847208T (es) |
SG (1) | SG11201407189XA (es) |
TW (1) | TWI574973B (es) |
WO (1) | WO2013169578A1 (es) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
JP6186010B2 (ja) | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Hiv成熟阻害活性を有するc−19修飾トリテルペノイド類 |
WO2014130810A1 (en) | 2013-02-25 | 2014-08-28 | Bristol-Myers Squibb Company | C-3 alkyl and alkenyl modified betulinic acid derivatives useful in the treatment of hiv |
UA120927C2 (uk) | 2014-04-11 | 2020-03-10 | Віів Гелскер Юк (Но.4) Лімітед | Тритерпеноїди, заміщені в положенні 3 неароматичним кільцем, яке несе галогеналкільний замісник, з інгібуючою активністю щодо дозрівання віл |
US9920090B2 (en) | 2014-06-19 | 2018-03-20 | VIIV Healthcare UK (No.5) Limited | Betulinic acid derivatives with HIV maturation inhibitory activity |
RU2017134461A (ru) * | 2015-04-14 | 2019-05-14 | ВАЙВ ХЕЛТКЕР ЮКей (N4) ЛИМИТЕД | Способы получения ингибитора созревания HIV |
WO2017017607A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
CA2993753A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
JP2018528231A (ja) | 2015-09-24 | 2018-09-27 | グラクソスミスクライン、インテレクチュアル、プロパティー、(ナンバー2)、リミテッドGlaxosmithkline Intellectual Property (No.2) Limited | Hiv成熟阻害活性を有する化合物 |
CN108699103A (zh) | 2016-01-20 | 2018-10-23 | 葛兰素史克知识产权第二有限公司 | 具有hiv成熟抑制活性的羽扇烷类的胺衍生物 |
AR107512A1 (es) * | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
AU2018331280B2 (en) * | 2017-09-13 | 2023-05-25 | Emmyon, Inc. | Ursolic acid morpholine and diethanolamine salts |
US20210347813A1 (en) | 2018-04-24 | 2021-11-11 | Viiv Healthcare Uk (No. 5) Limited | Compounds with hiv maturation inhibitory activity |
CN109705189B (zh) * | 2018-12-29 | 2020-06-05 | 中国医学科学院药用植物研究所 | 具有式i所示结构的三萜衍生物及其制备方法和应用 |
MX2021009584A (es) * | 2019-02-11 | 2021-09-23 | Hetero Labs Ltd | Nuevos derivados de triterpeno como inhibidores del virus de la inmunodeficiencia humana (vih). |
Family Cites Families (24)
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US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
BR0313265A (pt) | 2002-08-09 | 2005-07-05 | Astrazeneca Ab | Compostos e respectivos processos de preparação, uso e formulações farmacêuticas e métodos de prevenção e/ou tratamento de distúrbios mediados por receptor mglur5 e de inbição da ativação de receptores mglu r5. |
US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
ZA200704806B (en) * | 2004-11-12 | 2008-09-25 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
US20090105203A1 (en) | 2006-10-16 | 2009-04-23 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
AU2009214779A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17beta lupane derivatives |
US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
SG181803A1 (en) | 2009-12-17 | 2012-07-30 | Merck Sharp & Dohme | Aminopyrimidines as syk inhibitors |
WO2011153315A1 (en) | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
EA026140B1 (ru) * | 2010-06-04 | 2017-03-31 | Бристол-Майерс Сквибб Компани | С-28 амиды модифицированных производных с-3 бетулиновой кислоты в качестве ингибиторов созревания вич |
AP2013006706A0 (en) | 2010-07-02 | 2013-02-28 | Gilead Sciences Inc | Napht-2-ylacetic acid derivatives to treat AIDS |
HUE026371T2 (en) * | 2011-01-31 | 2016-05-30 | Bristol Myers Squibb Co | C-28 amines from modified C-3 betulinic acid derivatives as anti-HIV matrices |
MY162186A (en) | 2011-01-31 | 2017-05-31 | Viiv Healthcare Uk (No 4) Ltd | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
EA023463B1 (ru) | 2011-09-21 | 2016-06-30 | Бристол-Майерс Сквибб Компани | Производные бетулиновой кислоты с противовирусной активностью |
US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
-
2013
- 2013-03-13 US US13/799,479 patent/US8889854B2/en active Active
- 2013-05-03 ES ES13722947.2T patent/ES2652510T3/es active Active
- 2013-05-03 CN CN201380023798.5A patent/CN104540844B/zh not_active Expired - Fee Related
- 2013-05-03 KR KR1020147031255A patent/KR20150013157A/ko not_active Application Discontinuation
- 2013-05-03 WO PCT/US2013/039389 patent/WO2013169578A1/en active Application Filing
- 2013-05-03 AU AU2013259894A patent/AU2013259894B2/en not_active Ceased
- 2013-05-03 MX MX2014013089A patent/MX354914B/es active IP Right Grant
- 2013-05-03 JP JP2015511548A patent/JP6212545B2/ja active Active
- 2013-05-03 PT PT137229472T patent/PT2847208T/pt unknown
- 2013-05-03 CA CA2872891A patent/CA2872891C/en not_active Expired - Fee Related
- 2013-05-03 EP EP13722947.2A patent/EP2847208B1/en active Active
- 2013-05-03 BR BR112014027669A patent/BR112014027669A2/pt not_active Application Discontinuation
- 2013-05-03 EA EA201492016A patent/EA027133B1/ru not_active IP Right Cessation
- 2013-05-03 SG SG11201407189XA patent/SG11201407189XA/en unknown
- 2013-05-06 AR ARP130101545A patent/AR090955A1/es unknown
- 2013-05-06 TW TW102116106A patent/TWI574973B/zh not_active IP Right Cessation
-
2014
- 2014-11-03 IL IL235465A patent/IL235465A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP2015516422A (ja) | 2015-06-11 |
US8889854B2 (en) | 2014-11-18 |
CN104540844A (zh) | 2015-04-22 |
MX2014013089A (es) | 2014-12-08 |
EA027133B1 (ru) | 2017-06-30 |
TWI574973B (zh) | 2017-03-21 |
CA2872891A1 (en) | 2013-11-14 |
TW201350499A (zh) | 2013-12-16 |
CN104540844B (zh) | 2016-12-07 |
PT2847208T (pt) | 2017-12-14 |
BR112014027669A2 (pt) | 2017-06-27 |
WO2013169578A1 (en) | 2013-11-14 |
EP2847208B1 (en) | 2017-10-04 |
AU2013259894B2 (en) | 2017-07-13 |
SG11201407189XA (en) | 2014-12-30 |
JP6212545B2 (ja) | 2017-10-11 |
MX354914B (es) | 2018-03-26 |
EA201492016A1 (ru) | 2015-02-27 |
EP2847208A1 (en) | 2015-03-18 |
AU2013259894A1 (en) | 2015-01-15 |
ES2652510T3 (es) | 2018-02-02 |
US20130296554A1 (en) | 2013-11-07 |
IL235465A (en) | 2015-11-30 |
CA2872891C (en) | 2018-10-23 |
KR20150013157A (ko) | 2015-02-04 |
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