AU2016302940B2 - Prodrugs of glutamine analogs - Google Patents

Prodrugs of glutamine analogs Download PDF

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AU2016302940B2
AU2016302940B2 AU2016302940A AU2016302940A AU2016302940B2 AU 2016302940 B2 AU2016302940 B2 AU 2016302940B2 AU 2016302940 A AU2016302940 A AU 2016302940A AU 2016302940 A AU2016302940 A AU 2016302940A AU 2016302940 B2 AU2016302940 B2 AU 2016302940B2
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compound
cancer
group
alkyl
mmol
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AU2016302940A1 (en
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Andrej JANCARIK
Pavel Majer
Rana RAIS
Barbara Slusher
Lukas TENORA
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Institute of Organic Chemistry and Biochemistry CAS
Johns Hopkins University
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Institute of Organic Chemistry and Biochemistry CAS
Johns Hopkins University
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Assigned to THE JOHNS HOPKINS UNIVERSITY, Ústav organické chemie a biochemie AV ČR, v. v. i. reassignment THE JOHNS HOPKINS UNIVERSITY Amend patent request/document other than specification (104) Assignors: INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I., THE JOHNS HOPKINS UNIVERSITY
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    • C07C281/20—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group the two nitrogen atoms of the functional groups being doubly-bound to each other, e.g. azoformamide
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    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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    • 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
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    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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AU2016302940A 2015-07-31 2016-07-29 Prodrugs of glutamine analogs Active AU2016302940B2 (en)

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US201562199566P 2015-07-31 2015-07-31
US62/199,566 2015-07-31
PCT/US2016/044767 WO2017023774A1 (en) 2015-07-31 2016-07-29 Prodrugs of glutamine analogs

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Families Citing this family (27)

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CA2994165A1 (en) 2015-07-31 2017-02-09 The Johns Hopkins University Methods for cancer and immunotherapy using glutamine analogues, including don
US10842763B2 (en) 2015-07-31 2020-11-24 The Johns Hopkins University Methods for cancer and immunotherapy using prodrugs of glutamine analogs
WO2017023791A1 (en) * 2015-07-31 2017-02-09 The Johns Hopkins University Glutamine antagonists for the treatment of cognitive deficits
DK3328827T3 (da) 2015-07-31 2023-10-02 Univ Johns Hopkins Prodrugs af glutaminanaloger
CN110520118A (zh) 2017-02-01 2019-11-29 约翰斯霍普金斯大学 谷氨酰胺类似物的前药
DK3692015T3 (da) * 2017-10-06 2022-11-21 Univ Johns Hopkins Hidtil ukendte glutaminantagonister og anvendelser deraf
BR112021014112A2 (pt) * 2019-01-18 2021-10-13 Dracen Pharmaceuticals, Inc. Usos de composto pró-fármaco de don e inibidor de ponto de controle imunológico para tratar câncer, bem como composto e composição farmacêutica compreendendo o mesmo
JP2022519530A (ja) * 2019-02-11 2022-03-24 ドラセン ファーマシューティカルズ インコーポレイテッド Ｌ－ピログルタミン酸からｄｏｎプロドラッグを調製する方法
EP3924330A4 (en) * 2019-02-11 2022-11-09 Dracen Pharmaceuticals, Inc. PROCESS FOR THE PREPARATION OF A DON-PRODRUGE FROM L-GLUTAMIC ACID
IL291850A (en) * 2019-10-03 2022-06-01 Dracen Pharmaceuticals Inc Lyophilized composition containing (s)-isopropyl 2-((s)-2-acetamido-3-(h1-indol-3-yl)propanamido)-6-diazo-5-oxohexanoate for intravenous administration and use thereof
CN110763792A (zh) * 2019-10-24 2020-02-07 湖北省宏源药业科技股份有限公司 一种鸟嘌呤有关物质检测方法
WO2021239049A1 (en) * 2020-05-27 2021-12-02 Jacobio Pharmaceuticals Co., Ltd. Novel glutamine analogs
WO2022022612A1 (en) * 2020-07-29 2022-02-03 Jacobio Pharmaceuticals Co., Ltd. Novel glutamine analogs
CN116601140A (zh) 2020-10-02 2023-08-15 羿尊生物医药股份有限公司 用于皮下施用的包含(s)-2-((s)-2-乙酰氨基-3-(1h-吲哚-3-基)丙酰氨基)-6-重氮基-5-氧代己酸异丙酯的冻干组合物及其用途
AU2021361970A1 (en) 2020-10-15 2023-06-15 Jacobio Pharmaceuticals Co., Ltd. Novel glutamine analogs
WO2022078462A1 (en) * 2020-10-15 2022-04-21 Jacobio Pharmaceuticals Co., Ltd. Novel glutamine analogs
CN114621120B (zh) * 2020-12-10 2023-11-03 深圳先进技术研究院 一种don前药分子、前药激活化合物和前药激活体系
WO2022232565A1 (en) * 2021-04-29 2022-11-03 The Johns Hopkins University Prodrugs of 6-diazo-5-oxo-l-norleucine
WO2022261117A1 (en) * 2021-06-07 2022-12-15 Dracen Pharmaceuticals, Inc. Combination therapy with a don prodrug and a tigit inhibitor
CN113461563B (zh) * 2021-07-27 2022-05-10 中国药科大学 Nqo1激活型6-重氮基-5-氧代-l-正亮氨酸前药及其制备方法和应用
CN114306620A (zh) * 2021-12-07 2022-04-12 深圳先进技术研究院 基于代谢检查点的人血清白蛋白纳米药物及其制备方法和应用
JP2025078888A (ja) * 2022-01-28 2025-05-21 国立大学法人富山大学 グルタミナーゼ阻害剤
CN114917230B (zh) * 2022-03-09 2023-03-24 山东第一医科大学附属眼科研究所(山东省眼科研究所、山东第一医科大学附属青岛眼科医院) Cb-839在制备抑制角膜新生血管生成的药物中的应用
TW202404938A (zh) * 2022-04-21 2024-02-01 大陸商北京加科思新藥研發有限公司 麩醯胺酸拮抗劑的多晶型及其用途
TW202406539A (zh) * 2022-04-21 2024-02-16 大陸商北京加科思新藥研發有限公司 藥物組合及其用途
CN114805138B (zh) * 2022-05-12 2023-10-10 中国科学院长春应用化学研究所 6-重氮-5-氧代-l-正亮氨酸的前药、其制备方法及应用
WO2024094526A1 (en) 2022-11-02 2024-05-10 Ecole Polytechnique Federale De Lausanne (Epfl) 6-diazo-5-oxo-l-norleucine prodrugs

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0123170A2 (en) * 1983-04-25 1984-10-31 American Cyanamid Company Antibiotic LL-D05139beta
WO2014138391A1 (en) * 2013-03-06 2014-09-12 The Johns Hopkins University Targeting glutamine metabolism in brain tumors

Family Cites Families (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US121179A (en) * 1871-11-21 Improvement in brick-kilns
US3773919A (en) 1969-10-23 1973-11-20 Du Pont Polylactide-drug mixtures
IE52535B1 (en) 1981-02-16 1987-12-09 Ici Plc Continuous release pharmaceutical compositions
US4485045A (en) 1981-07-06 1984-11-27 Research Corporation Synthetic phosphatidyl cholines useful in forming liposomes
EP0102324A3 (de) 1982-07-29 1984-11-07 Ciba-Geigy Ag Lipide und Tenside in wässriger Phase
US4568646A (en) * 1983-04-25 1986-02-04 American Cyanamid Company Preparation of antibiotic LL-D05139β from cultures of Glycomyces harbinensis, gen. nov., sp. nov.
US4544545A (en) 1983-06-20 1985-10-01 Trustees University Of Massachusetts Liposomes containing modified cholesterol for organ targeting
HUT35524A (en) 1983-08-02 1985-07-29 Hoechst Ag Process for preparing pharmaceutical compositions containing regulatory /regulative/ peptides providing for the retarded release of the active substance
US5328470A (en) 1989-03-31 1994-07-12 The Regents Of The University Of Michigan Treatment of diseases by site-specific instillation of cells or site-specific transformation of cells and kits therefor
WO1997038986A1 (en) * 1996-04-12 1997-10-23 G.D. Searle & Co. Substituted benzenesulfonamide derivatives as prodrugs of cox-2 inhibitors
WO2001041707A2 (en) 1999-12-08 2001-06-14 Vanderbilt University Modulation of in vivo glutamine and glycine levels in the treatment of autism
JP2004509171A (ja) 2000-09-29 2004-03-25 ゾーン、　ロバート　ズィー． 炎症及び免疫反応の治療方法及びその組成物
US8048917B2 (en) 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
AU2003234597A1 (en) 2002-05-14 2003-12-02 The Board Of Trustees Of The Leland Stanford Junior University Drug therapy for celiac sprue
AU2003294221A1 (en) * 2002-09-13 2004-04-19 Kenneth E. Miller Method of alleviating pain via inhibition of neurotransmitter synthesis
GB0314262D0 (en) * 2003-06-19 2003-07-23 Univ Nottingham Trent Novel compounds and methods of using the same
KR20110097942A (ko) 2003-08-20 2011-08-31 제노포트 인코포레이티드 아실옥시알킬 카르바메이트 프로드러그, 합성 및 사용 방법
US7579313B2 (en) 2003-11-18 2009-08-25 The Board Of Trustees Of The Leland Stanford Junior University Transglutaminase inhibitors and methods of use thereof
CA2552740A1 (en) 2004-01-19 2005-07-28 Novartis Ag Indolylmaleimde derivatives as pkc inhibitors
CA2560311A1 (en) 2004-04-08 2005-10-20 Novartis Ag Protein kinase c inhibitors for the treatment of autoimmune diseases and of transplant rejection
US20060276438A1 (en) 2004-10-04 2006-12-07 Natarajan Sethuraman Prevention and treatment of influenza with glutamine antagonist agents
CA2605749C (en) 2005-04-26 2015-06-30 Eisai Co., Ltd. Compositions and methods for cancer immunotherapy
MX2008011220A (es) 2006-03-07 2008-09-11 Array Biopharma Inc Compuestos de pirazol heterobiciclicos y metodos de uso.
EP2015743B1 (de) 2006-05-10 2016-08-17 New Medical Enzymes AG Glutadon
US7585996B2 (en) 2006-09-15 2009-09-08 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
US20080107623A1 (en) 2006-11-01 2008-05-08 Bristol-Myers Squibb Company Inhibitors of Hepatitis C Virus
US8343477B2 (en) 2006-11-01 2013-01-01 Bristol-Myers Squibb Company Inhibitors of hepatitis C virus
US20080160024A1 (en) 2006-12-07 2008-07-03 Board Of Trustees Of The University Of Arkansas Inhibition of cancer metastasis
WO2009029729A1 (en) 2007-08-31 2009-03-05 Genelabs Technologies, Inc. Amino tricyclic-nucleoside compounds, compositions, and methods of use
JP5649137B2 (ja) 2010-02-17 2015-01-07 国立大学法人神戸大学 放射線治療剤
WO2011163594A2 (en) 2010-06-24 2011-12-29 Alkermes, Inc. Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives
US9402916B2 (en) 2011-03-17 2016-08-02 The University Of Birmingham Re-directed immunotherapy
KR101900478B1 (ko) 2011-08-04 2018-09-20 한올바이오파마주식회사 암의 재발 또는 전이의 억제용 약제학적 조성물
WO2014160071A1 (en) 2013-03-14 2014-10-02 St. Jude Children's Research Hospital Methods and compositions for the treatment of glutamine-addicted cancers
US10966998B2 (en) 2013-09-05 2021-04-06 The Johns Hopkins University Cancer therapy via a combination of epigenetic modulation and immune modulation
IL292510A (en) 2013-11-05 2022-06-01 Cognate Bioservices Inc Combinations of checkpoint inhibitors and therapeutics to treat cancer
JP2017500313A (ja) * 2013-12-09 2017-01-05 ブレット バイオテクノロジー， インコーポレーテッドＢｕｌｌｅｔ Ｂｉｏｔｅｃｈｎｏｌｏｇｙ， Ｉｎｃ． 特異的ウイルス様粒子−ＣｐＧオリゴヌクレオチドワクチンおよびその使用
CA2934700A1 (en) 2014-01-06 2015-07-09 Rhizen Pharmaceuticals Sa Glutaminase inhibitors
US20150258082A1 (en) 2014-03-14 2015-09-17 Francesco Parlati Combination therapy with glutaminase inhibitors
EP3154590B1 (en) 2014-06-13 2021-04-14 Calithera Biosciences, Inc. Combination therapy with glutaminase inhibitors
US10864180B2 (en) 2015-04-23 2020-12-15 The Johns Hopkins University Combination of immunotherapy with local chemotherapy for the treatment of malignancies
WO2017023791A1 (en) 2015-07-31 2017-02-09 The Johns Hopkins University Glutamine antagonists for the treatment of cognitive deficits
CA2994165A1 (en) * 2015-07-31 2017-02-09 The Johns Hopkins University Methods for cancer and immunotherapy using glutamine analogues, including don
US10842763B2 (en) 2015-07-31 2020-11-24 The Johns Hopkins University Methods for cancer and immunotherapy using prodrugs of glutamine analogs
DK3328827T3 (da) 2015-07-31 2023-10-02 Univ Johns Hopkins Prodrugs af glutaminanaloger

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0123170A2 (en) * 1983-04-25 1984-10-31 American Cyanamid Company Antibiotic LL-D05139beta
WO2014138391A1 (en) * 2013-03-06 2014-09-12 The Johns Hopkins University Targeting glutamine metabolism in brain tumors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Mohamed Abo-Ghalia et al, Int. J. Peptide Protein Res., 1988, 32, 208-222 *

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