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)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (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)
  • Peptides Or Proteins (AREA)
  • Plural Heterocyclic Compounds (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

Family

ID=57836622

Family Applications (3)

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

Country Status (24)

Country Link
US (4) US9732035B2 (enExample)
EP (4) EP3324958B1 (enExample)
JP (4) JP6842429B2 (enExample)
KR (2) KR20180086300A (enExample)
CN (2) CN111004167B (enExample)
AU (1) AU2016298471C1 (enExample)
BR (1) BR112018000225A2 (enExample)
CA (3) CA2992016C (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 (3) ES3051614T3 (enExample)
HK (2) HK1247837A1 (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 (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PE20180928A1 (es) 2015-07-24 2018-06-08 Newlink Genetics Corp Sales y profarmacos de 1-metil-d-triptofano
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
CN118286450A (zh) 2019-11-12 2024-07-05 纳米医疗有限公司 用于治疗癌症的含有ido拮抗剂前药的调配的和/或共同调配的脂质体组合物及其方法
US11833209B2 (en) 2020-09-11 2023-12-05 Nammi Therapeutics, Inc. Formulated and/or co-formulated liposome compositions containing PD-1 antagonist prodrugs useful in the treatment of cancer and methods thereof
KR20230158044A (ko) 2021-03-18 2023-11-17 남미 테라퓨틱스, 인크. 암의 치료에 유용한 A2aR 길항제 전구약물을 함유하는 제제화된 및/또는 공동-제제화된 리포솜 조성물 및 그의 방법
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
US6395876B1 (en) 1997-12-05 2002-05-28 Medical College Of Georgia Research Institute, Inc. High-affinity tryptophan transporter
JP3938689B2 (ja) * 2000-03-16 2007-06-27 エフ．ホフマン−ラ ロシュ アーゲー Ｉｐアンタゴニストとしてのカルボン酸誘導体
WO2002098877A1 (en) * 2001-06-05 2002-12-12 Lilly Icos Llc Pyrazino 1',2':1,6 pyrido 3,4-b indole1,4-dione derivatives
WO2004094409A1 (en) 2003-03-27 2004-11-04 Lankenau Institute For Medical Research Novel ido inhibitors and methods of use
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
WO2005073180A1 (ja) 2003-12-25 2005-08-11 Kureha Corporation 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
DK1879573T3 (da) 2005-05-10 2013-02-25 Incyte Corp Modulatorer af indolamin 2,3-dioxygenase og fremgangsmåder til anvendelse deraf
WO2007081878A2 (en) * 2006-01-07 2007-07-19 Medical College Of Georgia Research Institute, Inc. Indoleamine 2,3-dioxygenase pathways in the generation of regulatory t cells
US7705022B2 (en) 2005-10-27 2010-04-27 Lankenau Institute For Medical Research IDO inhibitors and methods of use thereof
ES2540561T3 (es) 2005-12-20 2015-07-10 Incyte Corporation N-hidroxiamidinoheterociclos como moduladores de indolamina 2,3-dioxigenasa
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
EP2137168B1 (en) 2007-03-16 2016-09-14 Lankenau Institute for Medical Research Novel ido inhibitors and methods of use thereof
WO2009073620A2 (en) 2007-11-30 2009-06-11 Newlink Genetics Ido inhibitors
ATE514671T1 (de) * 2008-02-01 2011-07-15 Firmenich & Cie Substituierte cyclohexenone
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
CA3012229C (en) 2008-07-08 2020-11-10 Incyte Holdings Corporation 1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase
SG176015A1 (en) 2009-05-13 2011-12-29 Gilead Sciences Inc Antiviral compounds
EP2493862B1 (en) 2009-10-28 2016-10-05 Newlink Genetics Corporation Imidazole derivatives as ido inhibitors
CA2788284A1 (en) * 2010-02-09 2011-08-18 Georgia Health Sciences University 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
EP2922847A1 (en) 2012-11-20 2015-09-30 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of indoleamine 2,3-dioxygenase
WO2014141110A2 (en) 2013-03-14 2014-09-18 Curadev Pharma Pvt. Ltd. Aminonitriles as kynurenine pathway inhibitors
CA2902174A1 (en) 2013-03-14 2014-10-02 Newlink Genetics Corporation Tricyclic compounds as inhibitors of immunosuppression mediated by tryptophan metabolization
JP6603649B2 (ja) 2013-03-14 2019-11-06 キュラデブ ファーマ プライベート リミテッド キヌレニン経路の阻害剤
HUE039339T2 (hu) 2013-03-15 2018-12-28 Bristol Myers Squibb Co Indolamin-2,3-dioxigenáz (IDO) inhibitorai
BR112015022462A8 (pt) 2013-03-15 2019-11-26 Bristol Myers Squibb Co inibidores de ido, composição farmacêutica, método de inibição de atividade de indolamina 2,3-dioxigenase e uso dos referidos inibidores
CN105473550B (zh) 2013-07-01 2019-02-15 百时美施贵宝公司 Ido抑制剂
CN105517999B (zh) 2013-07-11 2019-06-28 百时美施贵宝公司 Ido抑制剂
PE20180928A1 (es) 2015-07-24 2018-06-08 Newlink Genetics Corp Sales y profarmacos de 1-metil-d-triptofano
BR112018068177B1 (pt) 2016-03-09 2024-02-27 Emory University Composto, uso do composto e composição para eliminação do vírus da hepatite b com agentes antivirais
US10741094B2 (en) 2016-06-30 2020-08-11 Timpson Electrical & Aerial Services, LLC High voltage training device and system and method thereof

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US20200283385A1 (en) 2020-09-10
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