BRPI0509745A - compostos de difenil ox-indol-2-ona e seu uso no tratamento de cáncer - Google Patents
compostos de difenil ox-indol-2-ona e seu uso no tratamento de cáncerInfo
- Publication number
- BRPI0509745A BRPI0509745A BRPI0509745-2A BRPI0509745A BRPI0509745A BR PI0509745 A BRPI0509745 A BR PI0509745A BR PI0509745 A BRPI0509745 A BR PI0509745A BR PI0509745 A BRPI0509745 A BR PI0509745A
- Authority
- BR
- Brazil
- Prior art keywords
- compounds
- indol
- cancer
- diphenyl
- dihydro
- Prior art date
Links
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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/407—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 condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Abstract
COMPOSTOS DE DIFENIL OX-INDOL-2-ONA E SEU USO NO TRATAMENTO DE CáNCER. A presente invenção refere-se aos compostos de 3,3-difenil-1 ,3-diidro-indol-2-ona substituídos, e ao uso de tais compostos para a preparação de um medicamento para o tratamento de câncer, em um mamífero. Postula-se que o tratamento de cânceres nos quais a inibição da síntese protéica e/ou a inibição da ativação da via de mTOR é um método efetivo para a redução do crescimento celular. Os exemplos de tais cânceres são o câncer de mama, o câncer renal, o mieloma múltiplo, a leucemia, o glioblastoma, o rabdomiossarcoma, a próstata, o sarcoma de tecido mole, o sarcoma colorretal, o carcinoma gástrico, o carcinoma de células escamosas da cabeça e do pescoço, o uterino, o cervical, o melanoma, o linfoma, e o câncer pancreático. Uma subclasse particular dos compostos é representada pela fórmula (II), em que pelo menos um de X¬ 1¬ e X¬ 2¬ é um heteroátomo substituído, por exemplo, a 6-cloro-3,3-bis-(4-hidróxi-fenil-7-metil-1,3-diidro-indol-2-ana.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200400576 | 2004-04-08 | ||
DKPA200400693 | 2004-05-01 | ||
DKPA200401153 | 2004-07-27 | ||
DKPA200401216 | 2004-08-11 | ||
PCT/DK2005/000244 WO2005097107A2 (en) | 2004-04-08 | 2005-04-08 | Diphenyl - indol-2-on compounds and their use in the treatment of cancer |
Publications (1)
Publication Number | Publication Date |
---|---|
BRPI0509745A true BRPI0509745A (pt) | 2007-09-25 |
Family
ID=34965522
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BRPI0509745-2A BRPI0509745A (pt) | 2004-04-08 | 2005-04-08 | compostos de difenil ox-indol-2-ona e seu uso no tratamento de cáncer |
Country Status (15)
Country | Link |
---|---|
US (1) | US20070299102A1 (pt) |
EP (1) | EP1734951A2 (pt) |
JP (1) | JP2007532496A (pt) |
KR (1) | KR20060130781A (pt) |
CN (1) | CN1953747A (pt) |
AU (1) | AU2005230232A1 (pt) |
BR (1) | BRPI0509745A (pt) |
CA (1) | CA2562399A1 (pt) |
CR (1) | CR8673A (pt) |
EA (1) | EA013209B1 (pt) |
EC (1) | ECSP066913A (pt) |
IL (1) | IL178012A0 (pt) |
NO (1) | NO20065034L (pt) |
NZ (1) | NZ550222A (pt) |
WO (1) | WO2005097107A2 (pt) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4989976B2 (ja) * | 2004-02-13 | 2012-08-01 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | 翻訳開始阻害剤としての3−3−二置換オキシインドール |
MY144968A (en) | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
MY145694A (en) | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
AR053713A1 (es) * | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
CA2626456C (en) | 2005-10-18 | 2018-01-09 | George Mason Intellectual Properties, Inc. | Mtor pathway theranostic |
WO2008046049A1 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro (furo [3, 2-c] pyridine-3-3 ' -indol) -2' (1'h)-one derivatives and related compounds for the treatment of sodium-channel mediated diseases, such as pain |
MX2009003874A (es) * | 2006-10-12 | 2009-04-22 | Xenon Pharmaceuticals Inc | Derivados de espiro-oxindol triciclicos y sus usos como agentes terapeuticos. |
WO2008060789A2 (en) * | 2006-10-12 | 2008-05-22 | Xenon Pharmaceuticals Inc. | Use of spiro-oxindole compounds as therapeutic agents |
US20100029646A1 (en) * | 2006-12-11 | 2010-02-04 | Topo Target A/S | Prodrugs of diphenyl ox-indol-2-one compounds |
WO2008129075A1 (en) * | 2007-04-24 | 2008-10-30 | Topotarget A/S | Substituted 3-(4-hydroxyphenyl)-indolin-2-one-compounds |
GEP20125664B (en) | 2008-02-26 | 2012-10-10 | Takeda Pharmaceuticals Co | Condensed heterocyclic derivatives and application thereof |
US20100048913A1 (en) | 2008-03-14 | 2010-02-25 | Angela Brodie | Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens;Synthesis In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity |
JP5647098B2 (ja) | 2008-03-21 | 2014-12-24 | ザ ユニヴァーシティー オヴ シカゴ | オピオイド拮抗薬とmTOR阻害薬を用いた治療 |
EP2350091B1 (en) | 2008-10-17 | 2015-06-03 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
SG10201703086VA (en) | 2008-10-17 | 2017-05-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their use as therapeutic agents |
US8110578B2 (en) * | 2008-10-27 | 2012-02-07 | Signal Pharmaceuticals, Llc | Pyrazino[2,3-b]pyrazine mTOR kinase inhibitors for oncology indications and diseases associated with the mTOR/PI3K/Akt pathway |
AU2010210422A1 (en) | 2009-02-05 | 2011-08-18 | Tokai Pharmaceuticals, Inc. | Novel prodrugs of steroidal CYP17 inhibitors/antiandrogens |
WO2010109008A1 (en) | 2009-03-26 | 2010-09-30 | Topotarget A/S | Prodrugs of substituted 3-(4-hydroxyphenyl)-indolin-2-ones |
AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
RU2544852C2 (ru) * | 2009-10-14 | 2015-03-20 | Ксенон Фармасьютикалз Инк. | Способы синтеза спиро-оксиндольных соединений |
WO2011047173A2 (en) * | 2009-10-14 | 2011-04-21 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
CN102573472A (zh) | 2009-10-23 | 2012-07-11 | 健康研究公司 | 治疗雄激素受体阳性癌症的方法 |
US9504671B2 (en) | 2010-02-26 | 2016-11-29 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents |
EP2945646A4 (en) * | 2013-01-18 | 2016-09-21 | David J Shapiro | ESTROGEN RECEPTOR INHIBITORS |
BR112015023098A2 (pt) | 2013-03-14 | 2017-07-18 | Univ Jefferson | agentes de infrarregulação do receptor de andrógeno e usos dos mesmos |
CN105636594A (zh) | 2013-08-12 | 2016-06-01 | 托凯药业股份有限公司 | 使用雄激素靶向疗法用于***性疾病的生物标记物 |
WO2015108912A1 (en) | 2014-01-16 | 2015-07-23 | MUSC Foundation for Research and Development | Targeted nanocarriers for the administration of immunosuppressive agents |
TW201636017A (zh) | 2015-02-05 | 2016-10-16 | 梯瓦製藥國際有限責任公司 | 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法 |
WO2019157300A1 (en) * | 2018-02-08 | 2019-08-15 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A method of treating triple-negative breast cancer |
CR20210060A (es) | 2018-07-03 | 2021-04-08 | Univ Illinois | Activadores de la respuesta a proteínas desplegadas |
EP3912625A1 (en) * | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
CN114213396B (zh) * | 2022-01-27 | 2023-03-24 | 深圳市乐土生物医药有限公司 | 一种吲哚-2-酮类化合物及其制备方法与用途 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2258505A1 (de) * | 1971-12-02 | 1973-06-07 | Ciba Geigy Ag | Oxindoldiamine und verfahren zu ihrer herstellung |
ES426436A1 (es) * | 1974-05-18 | 1976-07-01 | Andreu Sa Dr | Procedimiento para la obtencion de derivados de la 3,3-bis (4-hidroxifenil)-2-indolinona. |
JPS5590943A (en) * | 1978-12-28 | 1980-07-10 | Fuji Photo Film Co Ltd | Photosensitive material and image forming method applicable thereto |
DE3510730A1 (de) * | 1985-03-08 | 1986-09-11 | Möve-Werk GmbH & Co KG, 7410 Reutlingen | Verfahren zur herstellung eines baumwollgewebes |
US6800658B2 (en) * | 1997-11-20 | 2004-10-05 | Children's Medical Center Corporation | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment of prevention of diseases characterized by abnormal cell proliferation |
EP1047411B1 (en) * | 1997-11-20 | 2004-02-11 | President And Fellows Of Harvard College | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation |
US6391907B1 (en) * | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
EP1487792A1 (en) * | 2002-03-15 | 2004-12-22 | Eli Lilly And Company | Dihydroindol-2-one derivatives as steroid hormone nuclear receptor modulators |
JP4989976B2 (ja) * | 2004-02-13 | 2012-08-01 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | 翻訳開始阻害剤としての3−3−二置換オキシインドール |
-
2005
- 2005-04-08 KR KR1020067023439A patent/KR20060130781A/ko not_active Application Discontinuation
- 2005-04-08 EA EA200601879A patent/EA013209B1/ru not_active IP Right Cessation
- 2005-04-08 AU AU2005230232A patent/AU2005230232A1/en not_active Abandoned
- 2005-04-08 WO PCT/DK2005/000244 patent/WO2005097107A2/en active Application Filing
- 2005-04-08 BR BRPI0509745-2A patent/BRPI0509745A/pt not_active IP Right Cessation
- 2005-04-08 CA CA002562399A patent/CA2562399A1/en not_active Abandoned
- 2005-04-08 US US10/599,121 patent/US20070299102A1/en not_active Abandoned
- 2005-04-08 JP JP2007506660A patent/JP2007532496A/ja active Pending
- 2005-04-08 CN CNA2005800102502A patent/CN1953747A/zh active Pending
- 2005-04-08 EP EP05715161A patent/EP1734951A2/en not_active Withdrawn
- 2005-04-08 NZ NZ550222A patent/NZ550222A/en unknown
-
2006
- 2006-09-11 IL IL178012A patent/IL178012A0/en unknown
- 2006-10-05 CR CR8673A patent/CR8673A/es not_active Application Discontinuation
- 2006-10-10 EC EC2006006913A patent/ECSP066913A/es unknown
- 2006-11-02 NO NO20065034A patent/NO20065034L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2005097107A2 (en) | 2005-10-20 |
WO2005097107A8 (en) | 2006-02-16 |
KR20060130781A (ko) | 2006-12-19 |
CN1953747A (zh) | 2007-04-25 |
AU2005230232A1 (en) | 2005-10-20 |
WO2005097107A3 (en) | 2006-03-30 |
EA013209B1 (ru) | 2010-04-30 |
NZ550222A (en) | 2010-09-30 |
US20070299102A1 (en) | 2007-12-27 |
CA2562399A1 (en) | 2005-10-20 |
IL178012A0 (en) | 2006-12-31 |
JP2007532496A (ja) | 2007-11-15 |
EA200601879A1 (ru) | 2007-04-27 |
CR8673A (es) | 2007-07-19 |
ECSP066913A (es) | 2007-02-28 |
NO20065034L (no) | 2006-11-02 |
EP1734951A2 (en) | 2006-12-27 |
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