CA2992016C - Salts and prodrugs of 1-methyl-d-tryptophan - Google Patents

Salts and prodrugs of 1-methyl-d-tryptophan Download PDF

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Publication number
CA2992016C
CA2992016C CA2992016A CA2992016A CA2992016C CA 2992016 C CA2992016 C CA 2992016C CA 2992016 A CA2992016 A CA 2992016A CA 2992016 A CA2992016 A CA 2992016A CA 2992016 C CA2992016 C CA 2992016C
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Canada
Prior art keywords
indoximod
methyl
salt
nlg
cancer
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CA2992016A
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English (en)
French (fr)
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CA2992016A1 (en
Inventor
Mario Mautino
Sanjeev Kumar
Firoz Jaipuri
Jesse Waldo
Hima Potturi
Hong Zhuang
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Lumos Pharma Inc
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NewLink Genetics Corp
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Priority to CA3051388A priority Critical patent/CA3051388C/en
Publication of CA2992016A1 publication Critical patent/CA2992016A1/en
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    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • 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
    • A61K31/28—Compounds containing heavy metals
    • A61K31/285—Arsenic compounds
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
CA2992016A 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan Active CA2992016C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3051388A CA3051388C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201562196671P 2015-07-24 2015-07-24
US62/196,671 2015-07-24
US201662305748P 2016-03-09 2016-03-09
US62/305,748 2016-03-09
PCT/US2016/035391 WO2017019175A1 (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3051388A Division CA3051388C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan

Publications (2)

Publication Number Publication Date
CA2992016A1 CA2992016A1 (en) 2017-02-02
CA2992016C true CA2992016C (en) 2019-10-22

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CA3132620A Active CA3132620C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan
CA2992016A Active CA2992016C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan
CA3051388A Active CA3051388C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan

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CA3132620A Active CA3132620C (en) 2015-07-24 2016-06-02 Salts and prodrugs of 1-methyl-d-tryptophan

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Country Status (24)

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US (4) US9732035B2 (enExample)
EP (4) EP4659747A2 (enExample)
JP (4) JP6842429B2 (enExample)
KR (2) KR20180030825A (enExample)
CN (2) CN107847486A (enExample)
AU (1) AU2016298471C1 (enExample)
BR (1) BR112018000225A2 (enExample)
CA (3) CA3132620C (enExample)
CL (1) CL2018000082A1 (enExample)
CO (1) CO2017013724A2 (enExample)
CR (1) CR20180023A (enExample)
DO (1) DOP2018000011A (enExample)
EA (1) EA201792256A1 (enExample)
EC (1) ECSP18002561A (enExample)
ES (2) ES2923184T3 (enExample)
HK (2) HK1247844A1 (enExample)
IL (2) IL255625B (enExample)
MA (1) MA43294A1 (enExample)
MX (1) MX2018001014A (enExample)
NZ (1) NZ736978A (enExample)
PE (1) PE20180928A1 (enExample)
PH (1) PH12017502046A1 (enExample)
WO (1) WO2017019175A1 (enExample)
ZA (1) ZA201800208B (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017019175A1 (en) 2015-07-24 2017-02-02 Newlink Genetics Corporation Salts and prodrugs of 1-methyl-d-tryptophan
CN109400517A (zh) * 2017-08-17 2019-03-01 上海时莱生物技术有限公司 1-甲基-色氨酸类化合物及其制备方法和用途
EP4176876A1 (en) 2017-09-14 2023-05-10 Lankenau Institute for Medical Research Methods and compositions for the treatment of cancer
CN109646683A (zh) * 2019-02-27 2019-04-19 武汉理工大学 一种1-mt-羧甲基壳聚糖药物的制备方法
JP2023502182A (ja) 2019-11-12 2023-01-20 ナミ セラピューティクス， インコーポレイテッド がんの処置において有用なｉｄｏアンタゴニストプロドラッグを含有する製剤化および／または共製剤化されたリポソーム組成物およびその方法
WO2022055542A1 (en) 2020-09-10 2022-03-17 Nammi Therapeutics, Inc. Formulated and/or co-formulated liposome compositions containing pd-1 antagonist prodrugs useful in the treatment of cancer and methods thereof
KR20250029575A (ko) 2023-08-23 2025-03-05 한국과학기술원 카메라 시스템의 동적 환경에 강인한 자기 위치 추정 장치 및 그 방법

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US14139A (en) 1856-01-22 Method oe ventilating railroad-cabs
GB1330573A (en) * 1970-09-12 1973-09-19 Ajinomoto Kk Optical resolution of dl-tryptophan derivatives
US4072691A (en) * 1974-01-12 1978-02-07 Tanabe Seiyaku Co., Ltd. Process for the resolution of DL-6-chlorotryptophan
US5185157A (en) * 1990-05-02 1993-02-09 Caston John C Treatment of refractory Eosinophilia-Myalgia Syndrome with L-tryptophan composition
WO1996011927A1 (en) 1994-10-12 1996-04-25 Abbott Laboratories Endothelin antagonists
AU1628599A (en) 1997-12-05 1999-06-28 Medical College Of Georgia Research Institute, Inc. Regulation of t cell-mediated immunity by tryptophan
KR100523119B1 (ko) * 2000-03-16 2005-10-20 에프. 호프만-라 로슈 아게 Ｉｐ 길항제로서의 카복실산 유도체
ATE397606T1 (de) * 2001-06-05 2008-06-15 Lilly Icos Llc Pyrazino(1',2':1,6)-pyrido(3,4-b) indole-1,4- dionderivate
EP2260846B1 (en) 2003-03-27 2018-11-28 Lankenau Institute for Medical Research Novel methods for the treatment of cancer
US7598287B2 (en) * 2003-04-01 2009-10-06 Medical College Of Georgia Research Institute, Inc. Use of inhibitors of indoleamine-2,3-dioxygenase in combination with other therapeutic modalities
JO2625B1 (en) 2003-06-24 2011-11-01 ميرك شارب اند دوم كوربوريشن Phosphoric acid salts of dipeptidyl betidase inhibitor 4
JPWO2005073180A1 (ja) 2003-12-25 2008-01-10 株式会社クレハ ヒドロキサム酸誘導体、及び該誘導体を含むａｇｅ生成阻害剤
ME02461B (me) 2005-05-10 2017-02-20 Incyte Holdings Corp Modulatori indoleamina 2,3-dioksigenaze i metode za upotrebu istih
US7705022B2 (en) 2005-10-27 2010-04-27 Lankenau Institute For Medical Research IDO inhibitors and methods of use thereof
EP1971583B1 (en) 2005-12-20 2015-03-25 Incyte Corporation N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase
EP1981534A4 (en) * 2006-01-07 2012-04-04 Med College Georgia Res Inst INDOLAMINE-2,3-DIOXYGENASE WAYS IN GENERATING REGULATORY T CELLS
CA2569204A1 (en) * 2006-11-28 2008-05-28 Apotex Technologies Inc. Crystalline d-isoglutamyl-d-tryptophan and the mono ammonium salt of d-isoglutamyl-d-tryptophan
US20100055111A1 (en) * 2007-02-14 2010-03-04 Med. College Of Georgia Research Institute, Inc. Indoleamine 2,3-dioxygenase, pd-1/pd-l pathways, and ctla4 pathways in the activation of regulatory t cells
WO2008115804A1 (en) 2007-03-16 2008-09-25 Lankenau Institute For Medical Research Novel ido inhibitors and methods of use thereof
EP2227233B1 (en) 2007-11-30 2013-02-13 Newlink Genetics Ido inhibitors
US8173846B2 (en) * 2008-02-01 2012-05-08 Firmenich Sa Substituted cyclohexenones
JP2011518841A (ja) 2008-04-24 2011-06-30 ニューリンク ジェネティクス， インコーポレイテッド Ｉｄｏ阻害剤
SG10201805844QA (en) 2008-07-08 2018-08-30 Incyte Holdings Corp 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase
HUE036906T2 (hu) 2009-05-13 2018-08-28 Antivirális vegyületek
EP2493862B1 (en) 2009-10-28 2016-10-05 Newlink Genetics Corporation Imidazole derivatives as ido inhibitors
WO2011100295A2 (en) * 2010-02-09 2011-08-18 Medical College Of Georgia Research Institute, Inc. Alpha-methyl-tryptophan as an inhibitor of indoleamine dioxygenase
NO2694640T3 (enExample) 2011-04-15 2018-03-17
JO3353B1 (ar) 2012-04-20 2019-03-13 Ono Pharmaceutical Co شكل صلب معزول من أحادي هيدروكلوريد أناموريلين بنسبة مولارية منخفضة من الكلوريد: أناموريلين ومحتوى منخفض من مذيب عضوي متبقي
KR20150087400A (ko) 2012-11-20 2015-07-29 버텍스 파마슈티칼스 인코포레이티드 인돌아민 2,3-디옥시게나제의 억제제로서 유용한 화합물
PE20151719A1 (es) 2013-03-14 2015-11-19 Curadev Pharma Private Ltd Inhibidores de la ruta de quinurenina
PE20151593A1 (es) 2013-03-14 2015-11-05 Newlink Genetics Corp Compuestos triciclicos como inhibidores de la inmunosupresion mediada por el metabolismo del triptofano
WO2014141110A2 (en) 2013-03-14 2014-09-18 Curadev Pharma Pvt. Ltd. Aminonitriles as kynurenine pathway inhibitors
PL2970155T3 (pl) 2013-03-15 2018-09-28 Bristol-Myers Squibb Company Inhibitory 2,3-dioksygenazy indoloaminy (ido)
JP6313415B2 (ja) 2013-03-15 2018-04-18 ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ Ｉｄｏ阻害剤
EA029126B1 (ru) 2013-07-01 2018-02-28 Бристол-Майерс Сквибб Компани Ингибиторы ido
CA2917964A1 (en) 2013-07-11 2015-01-15 Bristol-Myers Squibb Company Ido inhibitors
WO2017019175A1 (en) 2015-07-24 2017-02-02 Newlink Genetics Corporation Salts and prodrugs of 1-methyl-d-tryptophan
KR102390675B1 (ko) 2016-03-09 2022-04-26 에모리 유니버시티 항바이러스제에 의한 b형 간염 바이러스의 제거
WO2018006035A1 (en) 2016-06-30 2018-01-04 Timpson Electrical & Aerial Services, LLC High voltage training device and system and method thereof

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