AU2021241625B2 - Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity - Google Patents

Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity Download PDF

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Publication number
AU2021241625B2
AU2021241625B2 AU2021241625A AU2021241625A AU2021241625B2 AU 2021241625 B2 AU2021241625 B2 AU 2021241625B2 AU 2021241625 A AU2021241625 A AU 2021241625A AU 2021241625 A AU2021241625 A AU 2021241625A AU 2021241625 B2 AU2021241625 B2 AU 2021241625B2
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oligopeptide
animal
feed
substituted
composition
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AU2021241625A1 (en
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Bernhard Kaltenboeck
Horace Disston NALLE Jr.
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Nutrivert Inc
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Nutrivert Inc
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    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A23K20/147—Polymeric derivatives, e.g. peptides or proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
    • A61K2039/55511—Organic adjuvants
    • A61K2039/5555—Muramyl dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Fodder In General (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
AU2021241625A 2020-03-26 2021-03-25 Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity Active AU2021241625B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202063000364P 2020-03-26 2020-03-26
US63/000,364 2020-03-26
PCT/US2021/024142 WO2021195372A1 (en) 2020-03-26 2021-03-25 Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity

Publications (2)

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AU2021241625A1 AU2021241625A1 (en) 2022-11-10
AU2021241625B2 true AU2021241625B2 (en) 2025-04-24

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AU2021241625A Active AU2021241625B2 (en) 2020-03-26 2021-03-25 Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity

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US (1) US12492222B2 (enExample)
EP (1) EP4126040B1 (enExample)
JP (1) JP7667177B2 (enExample)
KR (1) KR102897673B1 (enExample)
CN (1) CN115605226A (enExample)
AU (1) AU2021241625B2 (enExample)
BR (1) BR112022019202A2 (enExample)
CA (1) CA3172936A1 (enExample)
ES (1) ES3014076T3 (enExample)
MX (1) MX2022011751A (enExample)
PL (1) PL4126040T3 (enExample)
WO (1) WO2021195372A1 (enExample)
ZA (1) ZA202210586B (enExample)

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EP3929293A3 (en) 2015-04-03 2022-03-16 University Of Massachusetts Fully stabilized asymmetric sirna
WO2017030973A1 (en) 2015-08-14 2017-02-23 University Of Massachusetts Bioactive conjugates for oligonucleotide delivery
WO2017132669A1 (en) 2016-01-31 2017-08-03 University Of Massachusetts Branched oligonucleotides
WO2018237245A1 (en) 2017-06-23 2018-12-27 University Of Massachusetts TWO TAIL SELF-ADMINISTRATION SIRNA AND ASSOCIATED METHODS
BR112021002440A2 (pt) 2018-08-10 2021-05-04 University Of Massachusetts oligonucleotídeos modificados visando snps
WO2020041769A1 (en) 2018-08-23 2020-02-27 University Of Massachusetts O-methyl rich fully stabilized oligonucleotides
CN113614232A (zh) 2019-01-18 2021-11-05 马萨诸塞大学 动态药代动力学修饰锚
EP3946369A4 (en) 2019-03-26 2023-10-18 University Of Massachusetts MODIFIED OLIGONUCLEOTIDES WITH INCREASED STABILITY
KR20220047989A (ko) 2019-08-09 2022-04-19 유니버시티 오브 매사추세츠 Snp를 표적화하는 화학적으로 변형된 올리고뉴클레오타이드
US12365894B2 (en) 2019-09-16 2025-07-22 University Of Massachusetts Branched lipid conjugates of siRNA for specific tissue delivery
AU2021244600A1 (en) 2020-03-26 2022-11-03 University Of Massachusetts Synthesis of modified oligonucleotides with increased stability
CN115605226A (zh) 2020-03-26 2023-01-13 纽特莱特公司（Us） 具有抗炎和生长促进活性的去乙酰基葡糖胺胞壁酰二肽的亲脂对映异构体
CA3174079A1 (en) 2020-05-26 2021-12-02 Anastasia Khvorova Synthetic oligonucleotides having regions of block and cluster modifications
WO2024102639A1 (en) * 2022-11-08 2024-05-16 The Scripps Research Institute N-arylpyrazole nod2 agonists as promoters of immune checkpoint inhibitor therapy

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0635026B1 (en) * 1992-04-03 1999-11-10 Biochem Pharma Inc Novel lipophilic oligopeptides with immunomodulating activity
WO2016008946A1 (en) * 2014-07-16 2016-01-21 The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin Novel compounds
US20180371023A1 (en) * 2015-12-10 2018-12-27 Bharat Biotech International Limited Novel muramyl peptide derivative compound, synthesis and uses thereof
US20190125873A1 (en) * 2017-10-28 2019-05-02 Far Eastern Memorial Hospital Glucosamine peptide compounds for treating liver metabolic disorders

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FR2428051A1 (fr) * 1978-06-05 1980-01-04 Anvar Nouveaux composes du type muramyl-peptide et medicaments les contenant
SI9011830B (sl) 1990-09-27 1999-12-31 Univerza V Ljubljani, Fakulteta Za Farmacijo Novi N-acildipeptidi, postopki za njihovo pripravo in farmacevtski pripravki, ki jih vsebujejo
JPH0655107B2 (ja) 1991-03-13 1994-07-27 全国農業協同組合連合会 家畜，家禽，および魚介類用の抗仮性狂犬病ならびに抗病性飼料および飼料用添加物
WO1993013791A1 (en) 1992-01-20 1993-07-22 Peptech (Uk) Limited Use of muramyl peptides for enhancing animal production
CN1162920A (zh) * 1994-09-21 1997-10-22 英国佩普技术有限公司 胞壁酰肽化合物的应用
US5976580A (en) 1995-06-07 1999-11-02 Novus International, Inc. Nutrient formulation and process for enhancing the health, livability, cumulative weight gain or feed efficiency in poultry and other animals
GB9618673D0 (en) * 1996-09-06 1996-10-16 Peptech Uk Ltd The use of muramyl peptides
RU2375047C2 (ru) 2004-03-26 2009-12-10 Лек Фармасьютиклз Д.Д. Фармацевтическая лекарственная форма, устойчивая к действию желудочного сока, включающая n-(2-(2-фталимидоэтокси)ацетил)-l-аланил-d-глутаминовую кислоту (lk 423)
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WO2008070564A1 (en) 2006-12-01 2008-06-12 The Government Of The U.S.A, As Represented By The Secretary, Departmentof Health And Human Services Uses of muramyl dipeptide (mdp) for treating inflammation
KR20100059863A (ko) 2007-09-11 2010-06-04 몬도바이오테크 래보래토리즈 아게 치료제로서의 펩티드 티모신 베타 ４ 단독 또는 세크로핀 ａ와의 배합물의 용도
CN101918001B (zh) 2007-12-06 2016-11-16 英特威国际有限公司 使用醋酸美仑孕酮和齐帕特罗或其盐的联合治疗
CN101756026A (zh) 2008-12-11 2010-06-30 天津瑞贝特科技发展有限公司 增强虾、蟹硬壳速度的营养组合物及其制备方法、应用
DE102009002044A1 (de) 2009-03-31 2010-10-07 Evonik Degussa Gmbh Dipeptide als Futtermitteladditive
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CN102578414B (zh) 2012-02-23 2014-01-01 青岛绿曼生物工程有限公司 促进猪生长育肥、提高免疫力的复方蜂胶饲料添加剂及其制备方法
WO2013172517A1 (ko) 2012-05-16 2013-11-21 서울대학교산학협력단 뮤라밀-다이펩타이드를 포함하는 골소실 예방, 골재생 또는 골형성 촉진용 약학 조성물
WO2017068149A1 (en) 2015-10-21 2017-04-27 Cysal Gmbh Aspartyl-dipeptides for aquaculture
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WO2020019128A1 (zh) 2018-07-23 2020-01-30 深圳市健元医药科技有限公司 丙氨酸—赖氨酸—谷氨酸三肽衍生物及其应用
CN115605226A (zh) 2020-03-26 2023-01-13 纽特莱特公司（Us） 具有抗炎和生长促进活性的去乙酰基葡糖胺胞壁酰二肽的亲脂对映异构体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0635026B1 (en) * 1992-04-03 1999-11-10 Biochem Pharma Inc Novel lipophilic oligopeptides with immunomodulating activity
WO2016008946A1 (en) * 2014-07-16 2016-01-21 The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin Novel compounds
US20180371023A1 (en) * 2015-12-10 2018-12-27 Bharat Biotech International Limited Novel muramyl peptide derivative compound, synthesis and uses thereof
US20190125873A1 (en) * 2017-10-28 2019-05-02 Far Eastern Memorial Hospital Glucosamine peptide compounds for treating liver metabolic disorders

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NZ792610A (en) 2025-07-25
KR102897673B1 (ko) 2025-12-09
ZA202210586B (en) 2023-05-31
JP7667177B2 (ja) 2025-04-22
AU2021241625A1 (en) 2022-11-10
JP2023518973A (ja) 2023-05-09
EP4126040A4 (en) 2024-04-24
EP4126040A1 (en) 2023-02-08
US20230174577A1 (en) 2023-06-08
WO2021195372A1 (en) 2021-09-30
EP4126040C0 (en) 2025-02-19
ES3014076T3 (en) 2025-04-16
BR112022019202A2 (pt) 2022-11-08
PL4126040T3 (pl) 2025-04-28
KR20220158773A (ko) 2022-12-01
CA3172936A1 (en) 2021-09-30
EP4126040B1 (en) 2025-02-19
CN115605226A (zh) 2023-01-13
US12492222B2 (en) 2025-12-09
MX2022011751A (es) 2022-12-02

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