LV12074B - Peptīds un tā iegūšanas paņēmiens - Google Patents

Peptīds un tā iegūšanas paņēmiens Download PDF

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Publication number
LV12074B
LV12074B LVP-97-266A LV970266A LV12074B LV 12074 B LV12074 B LV 12074B LV 970266 A LV970266 A LV 970266A LV 12074 B LV12074 B LV 12074B
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LV
Latvia
Prior art keywords
trp
glu
phe
leu
pro
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LVP-97-266A
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English (en)
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LV12074A (lv
Inventor
Vladislav Deigin
Andrei Korotkov
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Immunotech Developments Inc
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20168146&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV12074(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Immunotech Developments Inc filed Critical Immunotech Developments Inc
Publication of LV12074A publication Critical patent/LV12074A/lv
Publication of LV12074B publication Critical patent/LV12074B/lv

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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
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07—Tetrapeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • 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
    • 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
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • C07K5/0812—Tripeptides 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
    • C07K5/08—Tripeptides
    • C07K5/0819—Tripeptides with the first amino acid being acidic
    • 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
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Immunology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Description

t LV 12074 neirran h cnoco6 ero ποπγΗβΗΗΛ 06jiacn> tcxhhkh H3o€pereHHe othochtch k MezouiHHe. a hmchho k cnoco6aM ποπγ'ίβΗΗΧ 6HOJiomnecicH aKTHBHUx BemecTB. o6najiaioujHX HMMyHHoperyjiHpyioixiHMH CBOūciBaMH, h mobcct ηβητη rrpHMeHCHHe b MeztHUHHe, BerepHHapHH. a TaicKe b 3KcnepHMefrrajn,HOH 6hoxhmhh.
Ilpe,miiecTByiouiHH ypoeeHb tcxhhkh AKryajibHocn> pa3pa6oTXH ηοβμχ 6e3Bpe,anfaix HMMyHoperyjmpyīomHX narmsoB, otoco6hi>ix ocraBOBHTb nporpeccHpy»iQHfi pocr τεκηχ 3a6<uieBa-hhh, KaK 3JioKaMecTBeHHtie H0B006pa3OBaHHB, cencnc, χροΗΗΗβοαιβ η BHJicnreKy-ume ΗΗφααΐΗΗ, pa3BHBaromHCCH Ha φθΗβ ΗΜΜγΗΟΑβφΗΙΙΗΤΗΜΧ COCTOaHHU, nOflTBepBCnaeTCB 6ojIbUlHM KOJIHHeCTBOM HCCJieaOBaHHH. ΠρΟΒβϋβΗΗΜΧ B 3TOH o6jiacTM.
Hatf6onee pacnpocrpaHeMHbiM cnoco6oM BbMtBJieHHH ηοββιχ nenmaOB BBjīaeTca BuaejieHHe βκτηβημχ πεπτκΐΗΒΐχ φρβκιικδ H3 cyMMapHbix TKaHeBbnc 3XCTpaKTOB, φρΒΚΙΙΗΟΗΗρΟΒΒΗΗΙΟ H OHHCTKS BrUIOTb JXO BbLSfineHHB HHJIHBHiXy- ajiiHoro Beiaeeraa h ero ΗΑβΗΤΗφΗΧΒΐΐΗΗ (SU N1600047, SU N1638849, SU N1737798). B npaicTHĪecKofi MejmuHHe ιπΗροκο H3BecTHbi b Ka^ecrae peryj»TO-POB HMMyHHb!X npOUCCCOB THMyCHbie 3KCipaiCTbI. B aaCTHOCTH. THM03HH φρΕΚΙΙΗΛ 5 /Goldstein A.L.. Guna A.. Latz M.M., Hardy H.A., White AJ, THMajiHH /CH.N 659586/. 3th SKCTpaicru coctobt H3 KOMimeicca Bemecra nojiHneimucHOH πρπρο-λβι h nonyHeH»e hx h3 npnpoAHUX hctohhhkob orpaHHMeHO cjioacHOcrbio npo-H3BoncTBa, ManbīM βμχοαομ βκτηβημχ BemecTB h 3Ha*JHTejibHOH BapHa6enb-HOCTblO ΗΧ φΗ3ΗΚ0-ΧΗΜΗΒβεΧΗΧ XapaKTepHCTHK Η 6HOJIOrHHeCKHX CBOHCTB. KpoMe Toro, H3-3a npHcyrcTBHa b πρκροΰΗΒΐχ npenapaTax THMyca 6an;iacTHbix ΧΟΜΠΟΗβΗΤΟΒ ΠρΗ HX HCn0JIb30BaHHH y 6oJZI>HbIX ΗΗΟΓ,Μ B03HHKai0T noSoHHbie ΒΒΛβΗΗΒ. ΠοαιβΛΗββ o6croaTejibCTBO aBHJiocb CTHMyjxoM jum co3jiaHHB chhtcth-necxHX nenTHjiHbix npenapaTOB. B HacToamee ΒρβΜΒ ocymecTBJieH chhtsj pj«a neirnuiOB. o6jianaioiHHx HMMyHoperyjurropHbiMH οβοηοτββμη: PCT WO 089/06134. SU N1541821. SU N15189S6. EP N230052. EP N406931. US N 5021551, US N 5013723. Ka*awH H3 noJiyHeHHbix cmimnecKiui nerriH- ΛΟΒ C OrpaHHHCHHblM KOMIUieKCOM Ηβθ6χθΑΗΜΜΧ CBOHCTB o6jiaflaeT BbICOKOH ax-THBHOCTbK), HH3KOH TOKCHBHOCTbK), OTCyTCTBHCM ΠΟδΟΗΗΜΧ 3φφθ(ΤΟΒ, ΧΟΤΟρΜβ OnpenenBIOTHXB03MOB(HOe ΠρΗΜβΗβΗΗβ B MCOTUHHe. 2
II,III
PacKpbrTHe K3o6perreHHH B ocHOBy H3o6pereHHB nojionceHa 3ajia«ta co3jxaHH* ηοβογο CHirreTH’iecKo— ro δΗοποΓΗΗβοκϋ aKTKBHoro nermma, o6H2majomero HMMyHoperyjrapytoiiuiM cbohctbom, φαρΜγπΒΐ: 5 X-A-D-Trp-Y, rae A - D-Glu, iD-Glu; X - H hjih Gly, Aia, Leu, Ile, Vai, NVaI, Pro, Tyr, Phe. Trp, D-AJa, D-Leu. D-IIe. D-Val, D-NVal. D-Pro, D-Tyr, D-Phe, D-Trp, y-aMHHOMacnaHHaa KHcnoTa. ξ-aMHHOKanpoHOBaa khcjiote; 10 Y - Gly, Ala, Leu, Ile, Vai, NVal, Pro, Tyr, Phe, Trp, D-Ala. D-Leu, D-IIe, D-Val. D-NVal, D-Pro. D-Tyr, D-Phe, D-Tip, γ-aMHHOMacjMHHaa KHcnoTa. ξ-aMHHOKanpoHOBaa KMcnoTa. -OH hjih 3aMemeHHUH aMHH (Ci - C3).
Llenbio H3o6pereHHB 6buio Taioice cosnaHHe npHHUHmiajībHO ηοβογο τϊχ-HOJiorHMecKoro npouecca noji^emui BeineciBa ποπηοηοη npupojiu. κοτορυΗ 15 no3BOjnui 6u πρκ μηηημβλβηομ Kojuraecroe η προοτοτβ craaHit nojiyHaTb c bmcokhm ββιχοζιομ προ,αγκτ BbiuienpHBefleHHOH 4>opMyjn>i, «rro «BJmerca onpene-jisoouihm npH npoH3BoacTBe (JiapMaiieBTHHecKoro npenapaTa.
CymHOCTb ηοβογο cnoco6a coctoht b cjurreje rJijrraMHHCOAepBcauucc nen-thsob b pacraope nyreM pacKpbmu BHyrpeHHoro annupiiaa Tper6ynuioKCH-20 KapSOHHJl rJiyxaMHHOBOH (D HJIH L) KHCJIOTBI COOTBeTCTByiOUIHM npOH3BOJXHUM D-Trp-Y c nocjieayiomHM xpoMaTorpacj)H*iecKHM pa3aeaetmeu a- η γ-ιοοΜβροΒ. ZlajībHefiujHH CHHTe3 npoBOjnuiH nyreM HapamHBaHna nenraaHOā uctih c no-MOlUbK) aXTKBKpOBaHHblX 3φ»ρ0Β TpeT6ymUOKCMKap6oHHJiaMHHOKHCJIOT. pana aHanoroB coe^HHeuHH neirmna b Ta6jn«e 1 npHBeaeHbi 3Ha«ie-25 hhx Rn B CHcreMe (xaopocļ>opM-MeTaHon-32% yxcycHan KHOiOTa=60:45:20) h Rn b cHCTCMe (6yTaHOji- nHpHanH-Boaa-yKCycHaa KHCJi0Ta=5:5:4:l ).
Tafijnma I Πβπτπα Rn Ro Abu-D-Glu-D-TrpOH 0J2 0.53 Abu-iD-GIu-D-Trp-OH 0.29 0.49 Aca-D-Gl u-D-Trp-OH 0.31 0.52 Aca-iD-Glu-D-Trp-OH 0.28 0.49 AJa-D-Glu-D-TitJ-OH 0.34 0.61 Ala-iD-Glu-D-Trp-OH 0.32 0.55 D-Ala-D-Glu-D-Tro-D-Ala 0.22 0.41 D-Ala-D-Glu-D-Tro-OH 0.26 0.51 D-Ala-i D-Gl u-D-Trp-D-Ala 0.25 0.50 D-Aia-iD-Glu-D-Tro-OH 0.25 0.51 3
Ull I LV 12074
Ta6jiHOa_J nerrota Rn Rn D-Ile-D-Glu-D-Trp-D-Leu 0.35 0.53 D-Ile-D-Glu-D-Trp-OH 0.36 0.54 D-Ile-iD-Gl u-D-T rp-D-Leu 0.34 0.53 D-Ile-iD-Glu-D-Trp-OH 0.27 0.52 D-Leu-D-Glu-D-Trp-OH 0.36 0.53 D-Leu-iD-Glu-D-Trp-OH 0.35 0.52 D-N V al-D-Glu-D-Trp-OH 0.33 0.51 D-NVal-iD-Glu-D-Trp-OH 0.32 0-51 D-Phe-D-Glu-D-Trp-Aia 0.37 0.56 D-Phe-iD-Glu-D-Trp-Ala 0.36 0.55 D-Pro-D-Glu-D-Trp-OH 0.38 0.58 D-Pro-iD-Glu-D-T rp-OH 0.37 0.58 D-Trp-D-Glu-D-Trp-OH 0.41 0.59 D-Trp-iD-Glu-D-Trp-OH 0.40 0.59 D-Tyr-D-Giu-D-Trp-D-Tyr 0.39 0.58 D-T yr-iD-Glu-D-Trp-D-Tvr 0.38 0.58 D-V al-D-Glu-D-T rp-OH 0.34 0.51 D-V al-iD-Glu- D-Trp-OH 0.33 0.50 Glv-D-Glu-D-Trp-NVal 0.29 0.51 Glv-D-Glu-D-Trp-OH 0.30 0.54 GIv-iD-Glu-D-Trp-N Vai 0.32 0.53 Gly-iD-Glu-D-Trp-OH 0.29 0.53 H-D-Glu- D-T rp-Abu 0.33 0.52 H-D-Glu-D-T rp-Aca 0.30 0.53 H-D-Glu-D-T rp-D-Ile 0.35 0.58 H-D-Glu-D-T rp-D-Pro 0.37 0.61 H-D-Glu-D-Trp-Glv 0.29 . 0.54 H-D-Glu-D-Trp-Ile 0.36 0.58 H-D-Glu-D-Trp-Leu 0.36 0.59 H-D-Glu-D-Trp-Lvs 0.28 0.47 H-D-Glu-D-T rp-OH 0-36 0.56 H-D-Glu-D-T rp-Phe 0.39 0.61 H-D-Glu-D-Trp-Pro 0.38 0.59 H-D-Glu-D-T rp-Tyr 0.37 0.58 H-D-Glu-D-T rp-Vai 0.38 0.61 H-iD-Glu-D-Trp-Abu 0.34 0.51 H-iD-Gl u-D-T rp-Aca 0.33 0.50 H-iD-Gl u-D-T rp-D-IIe 0.34 0-55 H-iD-Glu-D-Trp-D-Pro 0.36 0.58 H-iD-Glu-D-Trp-Gly 0.28 0.52 H-iD-Glu-D-Trp-IIe 0.34 0.57 H-iD-Glu-D-Trp-Leu 0.35 0.58 H-iD-Glu-D-Trp-Lvs 0.27 0.45 H-i D-Glu- D-T rp-OH 0.30 0.52 H-iD-Glu-D-Trp-Phe 0.38 0.61 H-iD-Glu-D-Trp-Pro 0.37 0.60 H-iD-Gl u-D-Trp-Tyr 0.35 0.58 H-iD-Glu-D-Trp-Val 0.36 0.60 4 11111
TaSjtHua I ΠίπτΗϋ Rn Rn Ue-D-Glu-D-Tro-D-Phe 0.42 0.68 Ile-D-Glu-D-Tro-OH 0.38 0.56 Ile-iD-Glu-D-Tro-D-Phe 0.40 0.67 Ile-iD-Glu-D-Tro-OH 0.37 0.55 Leu-D-Glu-D-Tn)-OH 0.35 0.62 Leu-iD-Glu-D-Trū-OH 0.27 0.57 NVal-D-Glu-D-Trp-OH 0.35 0.61 NVal-iD-Glu-D-Tro-OH 0.34 0.60 Phe-D-Glu-D-Trp-OH 0.41 0.63 Phe-iD-GIu-D-Trp-OH 0.40 0.62 Pro-D-Glu-D-Trp-OH 0.43 0.63 Pro-iD-Glu-D-Tro-OH 0.42 0.62 Trp-D-Glu-D-Tro-OH 0.45 0.68 Trp-iD-Glu-D-Tro-OH 0.44 0.67 Tyr-D-Glu-D-T ip-OH 0.42 0.64 Tvr-iD-Glu-D-Tro-OH 0.41 0.63 V al-D-Glu-D-T ip-D-Val 0.46 0.68 Val-D-Glu-D-Tru-OH 0.33 0.50 V al-lD-Glu-D-T ro-D-V al 0.44 0.66 V al-iD-Glu-D-T rp-OH 0.34 0.52 JIyHinife BapHaHTbi ocyujecrBJieHHa H3o6peTeH«a. H3o6peTeHHe njinK3crpHpyeTca aieay»mHM πρΗΜβροΜ. ΠρΗΜβρ.
5 H-D-GIu-D-Trp-OH h H-iD-G1u-D-Ttp-OH
1. ΠοπγπβΗΗβ Boc-D-Glu-OH 14.7 (O.Imojiji) H-D-G!u-OH pacrBopajnf 200 mm ΛΗστκπΗροΒaHHoii bosu, OZtHOMOJUpHfcIM paCTBOpOM KOH iZOBOZtHJIH pH flO 10,2 Η ΓφΗ HHTeHCHBHOM ne-peMeuiHBaHHH Ao6aBJi)uiH pacrBop 33.0 r (0,3 mojm) BOC2O B jnioKcaiie. Ca«tH-
10 jm 3a BenHHHHOH pH Ha pH-craTe. Iīocne οκοημβηηλ peaKUHH cMecb noMonajm b ααηπΌ&κγιο ΒοροΗκγ, 3KCTparwpoBaJiH H3 ihcjiohhoh cpeou 3x150 mm 3th-. JiaueraTOM. bouhjto φ33γ mwuichho ηοϋκηαυυχΗ 0,2% paciBopoM cepHoii khc-izcmi αο pH-3.0 h 3KcipaTHpoBanH Boc-D-Glu-OH b opramnecxyio φβ3y (3x200mm). OpraHHHeacHfi cnofi npoMbiBajra 3x200 mm HacumeHHUM pacreopoM 15 NaaS04 λο HeSrpajn>HOH cpe;o»i. cyununt Hazi N^SO* ynapHBajm b BaxyyMe no Maoioo6pa3Horo coctobhhb. Buxoa: 16,7 r (68%).
2. IIojiyHeHHe cMecH Boc-D-Glu-D-Trp-OH m Boc-iD-Glu-D-Trp-OH 16.7 r (0,068 MOBb) Boc-D-Glu-OH pacTBOpJum b 200 mji ΑΗΜβπιπφορΜΒ-Mitna, oxjiaacuaan no 0° h np« ncpcMeiaHBaHHH ao6aBJi3UiH pacreop 20,6 r 20 (O.Imojib) N,N'-juimaaioreKCHjxKap6o2iiHMHaa b 100 Μπ ΑΗΜητυιφορΜ8ΜΗ- LV 12074 jia. Cinecb nepeMeuiHBajiH 4 naca npH +4eC m ocraanjuiH Ha 8 MacoB npn KOMftaT-hoh TeMnepaType. BtinaBiHHā ocanoK nHinuaioreKCHJiMOHeBHHbi οτφιιιπ>τροΒΜ-Bam. ocaAOK npoMbiBamt 2x50 mm ΛΗΜβτΗπφορΜΗΜΗΛΟΜ, φΗπΒτρΒτ ynapnBajm b BaKyyMe λο I/2 o6teMa κ aofiaBJUinH πρκ oxjia»neHHH λο +4°C h HHTeHCHBHOM 5 nepeMeuiHBaHHH 24,3 (0,l MOJib) H-D-Trp-OK. Paereop ocraBJuuiH nocreneHHo HarpeBaTbca λο κομηβτηοη TeMnepaTypw. 06 OKOHHaHHH peaioiMH αιβΛΗΠΗ no TCX b CHcreMe (χποροφορΜ: 3THnaueTaT: MCTaHon 6:3:1) λο ΗσκαΗΟΒβΗΗΛ njrraa BHjrrpeHHero aHrunpuāa Boc-D-Glu khciotīi. OcrancH nniiHKJioreKCHJi-MOHeBHHbl 0ΤφΗΛΒΤρθΒΜΒ3ΛΗ. ΛΗΜβΤΗΛφορΜΛΜΜΛ ynapHBanH b BaKyyMe. K Mac-10 jioo6pa30My ocTa-ncy AoSaBJUiJiH 200 mm amaaneraTa h 200 μλ 0.2% pacraopa CepHOfl KHCJIOTil. OpraHHHCCKMH CJIOH ΟΤΛβΛΗΛΗ, npOMbIBaJIH ΛΟ HeiiTpaJībHOH ερβΛΒΐ HacbiiueHHbiM pacrBopoM NaiS04. cyuiHnH Η3Λ Na^SO*, 3THnaueTaT-hmh pacTBOp ynapHBajiH b BaKyyMe. rtonyHeHHbifi Macnoo6pa3Hbiā ocanoK πρβΛοτΒΒΛΧΛ co6oh cMecb Boc-D-Glu-D-Trp-OH h Boc-iD-Glu-D-Trp-OH. 15 OSuihh βμχολ Maciia cocraBna 25.4 r (70%).
3. riojiyHeHHe H-D-Glu-D-Trp-OH h H-iD-Glu-D-Trp-OH 25,4 r (0,048 mojib) cmcch pacrBopjuiH B 200 μλ MypaBbHHOfi kmcjiotīi, ne-peMemKBajīH npH 40SC b TeneHHe 1 qaca m ynapHBajiH b BaxyyMe λο Macnoo6pa3-ΗΟΓΟ COCTOflHHB. Pa3AeHHe H OHKCTKy ΠβΠΤΗΛΟΒ ηρΟΒΟΛΗΛΗ C nOMOUIbtO HOHO-20 OČMeHHOH ΧρΟΜΒΤΟΓρΒφΗΗ Ha ΚΟΛΟΗΚε C ΟβφβΛβκεΟΜ B ΓρβΛΗβΗΤβ 0,01-0,2 Μ πΗρΗΛΗΗΒΐιβτΒΤΗΟΓΟ 6yφepa. Βμχολ: 5.7 r (35%) H-D-Glu-D-Trp-OH η 5,7 r (35%) H-iD-Glu-D-Trp-OH. B pe3yjn>TaTe H3yM6HKB φΗ3Ηκο-χκΜΗΗβεχΗχ cbohctb nermtna SbuiH nony-neHbi cnenyiouiHe ero xapaKTepucTHKn:
25 ΠβρΒΗΗΗΛΛ crpyKTypa - H-D-Glu-D-Trp-OH h H-iD-Glu-D-Trp-OH
BpyTTO φopMyΛa - CisHmNsOj
MoJiescyjMpHbiH sec - 334.35 BHeUJHHH ΒΗΛ - θβΠΗΗ C 5KCJTTOBaTblM OTTeHKOM HJ1H CepbJH ΠΟ- ροιηοκ. 30 PaCTBOpHMOCTb - ΛβΓΚΟ paCTBOpHM B ΒΟΛΟ, γΜβρβΗΗΟ B αΠφΤβ, npaKTHiecKH HepacrBopHM b χηοροφορΜβ Υ.Φ.- cnejcrp b o6aacra 250-300 hm hmcct MaiccHMyM 280±2 mm, nneno 287±2hm. 6 BHOJiorHHecKaa aKTHBHOCTb ηοβογο neirraaa H3yqanacb Ha Mbimax jihhhh Balb/c. ΚπβτκΗ cejie3eHKH Mbimefi cycneHjmpOBajiH b cpeae RPMI 1640 c 2 mm rJiyTaMHHa H 5% ΗΗ3ΚΤΗΒΙφΟΒΒΗΗΟΗ φ3Τ3ΐη>Ηθίί CbIBOpOTKH H BHOCHJIH B ruioc-KoaoHHbie rmaHinerbi b KOJinnecTBe 100 mkji. cooTBercTBeHHO. 200.000 kjictok Ha JiyHKy. HccneayeMbjā npenapaT bhochjih b Hanajie Kyjn>THBHpoBaHHa. B Ka-necTBe MHToreHa Hcnojn>30BajiH KOHKaHasajiHH A b kohchhoh KOHueHTpatiHH 2 ΜΚΓ Ha JiyHKy. njiaHuie-π,ι ΗΗκγδπροΒηπΗ irpH 37°C h 5% CO: b τβπβΗΗβ 48 qa-cob. npojmtļjepaumo kjictok oueHHBanH no BJcnoHeHHio 3H-THMH£HHa. bhoch-μογο 3 a 24 naca ao οκοηηβηηχ Kyjn>THBnpoBaHM b ao3e 5 mkt/mji. c πομοιοβιο CIIHHTHJIJUIlHOHHOrO CHCTHHKa H BbipaHCaJIH B KOJIHHeCTBe paCnattOB B MHHyry (CPM). ĪIoJiyHeHHbie pe3yjn>TaTbi cyMMHpoBaHbi B TaējiHiie 2.
Ta6jiHixa2 Πρθ3ΙΗφ€Ρ311Η)Ι cejie3CHOHHbg KJICTOK Mbirnefi_ IIpenapaT CPMI* Ū03a npenapaTa (mkt/mji) 1 5 10 20 iD-Glu-D-Trp 68594 63428 20043 13222 Cvclosporin A 67649 2698 574 569 Ccntrol 6 1467 * - cpesHee H3 τρβχ onpeaeneHHū ΥσπίΗΟΒπβΗΟ, hto hobmh netrran očjiaaaer cnoco6HOcn>io HKniSHpoBaTb npontKļiepamno cejie3eHOHHbix κπβτοκ. C uejibio H3yHeHHX GaonacHocTH neimuia irpoBOjuiAH H3yneHHe ero ocr-pOH TOKCHHHOCTH. Η3}ΉβΗΗβ OCipOH TOKCHHHOCTH npOBOiDUIH B COOTBCTCTBHH C MeTO-HHHecKHMH peKOMeHAamuiMH OapMaKOJioranecicoro KOMHTera ΡΦ "TpefiOBaHHB K ,HOKJIHHHHeCKOMy H3yHeHHK3 oSmeTOKCHHHOrO aeHCIBHB HOBbUC φβρΜβΚΟΛΟΓΗΗβΟΧΗΧ BemecTB", M.. 1985 Γ.
Pc3ynbTaTbi HccjieaoBaHHH noKa3ajiH. <rro πρκ ΒΗγτρκθριοαίΗΗΗΟΜ BBeae-hhh 1000 KpaTHoS j[03bi neiima He 0Ka3breaji ocrporo τοκογμογο hchctbhji h
IipH 3ΤΗΧ Λ033Χ OK33aJIOCb HeB03 MO^KHblM aOCTHTHyn> HX LO]0. IīpoMbiuuieHKafl npHMeHHUocrb. ΠδΠΤΗΛ. o6jiaiQOUIHH δΗΟπΟΓΗΗβΟΧΟΗ aKTHBHOCTb20 MOBCCT HaŪTH UIHpo-KOe npHMCHCHHC Β MCAHUHHe Η ΒβΤβρΗΗΒρΗΗ. 7 7LV 12074
tDopMjura H3o6pereHHH !. ΠαπΗΚ φορΜγιπ»! X-A-D-Trp-Y, rae A - D-Glu. iD-Glu: 5 X - H hjih Gly, Ala, Leu, Ile, Vai. NVal, Pro, Tyr, Phe, Trp. D-Ala. D-Leu. D-Ile, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aMHHOMaciuHHaa KHcnoTa. ξ-aMHHOKanpoHOBaji KHcnoTa: Y - Gly, Ala, Leu. Ile, Vai. NVal. Pro, Tyr, Phe. Trp. D-Ala. D-Leu. D-IIe, D-Val, D-NVal. D-Pro. D-Tyr, D-Phe, D-Tip, γ-aMHHOMaoiHHHas ιαιαιοτβ. 10 ξ-aMHHOKanpoHOBaa KHCJiora, -OH hjih 3aMeuieHHbiū aMtut (Ci - Cj). 2.Cnoco6 nojr^eHHH neimuia φορΜ>οπ>ι X-A-D-Trp-Y, rae A-D-Glu, iD-Glu: X - Η hjih Gly. Ala. Leu. Ile, Vai. NVal. Pro. Tyr. Phe. Trp. D-Ala. D-Leu. D-IIe. 15 D-Val. D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, y-aMHHOMaaixHHax KHcnoTa, ξ-aMHHOKanpoHOBaa KHcnoTa; Y - Gly, Ala. Leu, Ile. Vai, NVal. Pro, Tyr, Phe. Trp, D-Ala, D-Leu, D-IIe. D-Val. D-NVal. D-Pro, D-Tyr, D-Phe. D-Trp. γ-aMHHOMacjHHHaa KHcnoTa, ξ-aMHHOKanpoHOBaa KHcnoTa, -OH hjih 3aMeuieHHbiii aMKH (Ci - Cj), 20 3axjno<iaioiiuiHca b tom. «rro cmrre3 neimuia npoBOjurr b pactBope nyreM pac-KpuTHB BHjTpeHHoro aHrHzīpHna Tper6yTHJioKCHKap6oKitnn[yTaMHHOBO!f (D hjih L) KHCJioTbi K-cojibio D-Trp-Y, 3areM HapauiHBaioT neimmHyK> uenb mctoaom aKTHBHpoBaHHbix 3φκροΒ h mctojiom cMeiuaHHbix ΒΗΓΗΛρΗΛΟΒ c npenBapirrenb-hum OTiueruieKHeM TpeT€ynuiOKCHKap6oHHjn>Hofi rpynnu nyTCM o6pa6oneu My-25 paBbHHOŪ KHCJIOTOH Η ΧρθΜ3ΤΟΓρ3φΗΜβΟΚΗΜ pa3AejieHHeM α- Η γ-Η30Μβρ0Β. . 30 Ρ·φ*ρ·τ Η3θ6ρβτβΗκε OTHOCHTCS χ MejnniHHe, a HMeHHO k cnocočaM noJiyHemw 6HOJionraecKH βχτκβημχ eemeciB, o6jia£aiomHX HMMyHHoperyjmpyīomHMn CBOHCTBaMH, H MOHCeT ΗΒΗΤΗ ΠρΗΜβΗβΗΗβ B MejDfUHHe, BCTCpHHapHH, a TaiCKe B OKCnepHMeBlcUībHOfi 6HOXHMHH. B 0CH0By ιηοβρβτβΗΗα nojioaceHa 3aflana co3£aHHH ηοβογο CHHTeTHHecico-ro δΗΟΠΟΓΗΗβοκΗ βχτηβηογο neirrana, o6jiajraK>mero HMMyH0peryjrapyE0imiu CBOHCTBOM, φθρΜγ3ΙΒΐ: X-A-D-Trp-Y, rae A-D-Glu, iD-Glu; X - H hjih Gly, Ala, Leu, Ile, Vai, NVaI, Pro, Tyr, Phe, Tip. D-AIa, D-Leu, D-IIe, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aMHHOMaaiaHHaa iracjiOTa, ξ-aMHHOKanpoHOBaa KHOiOTa; Y - Gly, Ala, Leu, Ile, Vai, NVal, Pro, Tyr. Phe, Trp, D-Ala, D-Leu, D-IIe, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, y-aMHHOMaawHHaji KHdOTa, ξ-aMHHOKanpoHOBaa KHOiOTa, -OH hjih 3aMeiueHHbifi aMHfl (Ci - C3).
Cnoco6 nojxyHeHiw neirama coctoht b CHHTe3e rJiyTaMHJicoaepHcaEmix nennmoB b paciBope nyreM pacxpt»mM BHyrpeHHoro aimurpHfla τρβτδ^πωοκ- CHXap60HHJI rJiyTaMHHOBOH (D HJIH L) KHOIOTM COOTBeTCTBJTOIHHM D-
Tip-Y c nocjieayx5mHM χροΜΕτοΓρΒφΗΗβοκΗΜ pa3seneHHeM α- η γ-ιποΜβροβ.
JajIbHeHUIHH CHHTC3 ΠρθΒΟΛΗΠΗ HJOCM HapaiIIHBaHHH ΠβΠΤΗΛΗΟΗ uenH C ΠΟ-ΜΟΙΠΜΟ aKTHBHpOBaHHbIX 3φΗρθΒ TpeT6yTHJIOKCHXap6oHHJiaMHHOKHCJIOT.

Claims (2)

  1. Izgudrojuma formula 1. Peptīds ar formulu X-A-D-Trp-Y, kurā: A- D-Glu, iD-Glu: X- H vai Gly, Ala, Leu, lle, Vai, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-lle, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aminosviestskābe, ξ-aminokapronskābe: Y- Gly, Ala, Leu, lle, Vai, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-lle, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aminosviestskābe, ξ-amino kapronskābe, -OH vai (C1-C3) aizvietots amīds.
  2. 2. Paņēmiens peptīda ar formulu X-A-D-Trp-Y, kurā: A- D-Glu, iD-Glu: X- H vai Gly, Ala, Leu, lle, Vai, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-lle, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aminosviestskābe, ξ-aminokapronskābe: Y- Gly, Ala, Leu, lle, Vai, NVal, Pro, Tyr, Phe, Trp, D-Ala, D-Leu, D-lle, D-Val, D-NVal, D-Pro, D-Tyr, D-Phe, D-Trp, γ-aminosviestskābe, ξ-amino kapronskābe, -OH vai (C1-C3) aizvietots amīds iegūšanai, kas raksturojas ar to, ka peptīda sintēzi veic šķīdumā, ar K-sāli D-Trp-Y uzšķeļot t-butiloksikarbonilglutamīn (D vai L) skābes iekšējo anhidrīdu un tālāk pagarinot peptīda ķēdi ar aktivēto esteru un jaukto anhidrīdu metodēm, iepriekš atšķeļot t-butiloksikarbonīlgrupu, to apstrādājot ar skudrskābi un hromatogrāfiski sadalot a- un γ- izomērus.
LVP-97-266A 1995-06-07 1997-12-19 Peptīds un tā iegūšanas paņēmiens LV12074B (lv)

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SK166997A3 (en) 1998-04-08
HUP9801990A2 (hu) 1999-02-01
CA2222296A1 (en) 1996-12-19
SK281825B6 (sk) 2001-08-06
BR9609235B1 (pt) 2009-01-13
EP0832900A1 (en) 1998-04-01
HUP9801990A3 (en) 1999-06-28
LT4476B (lt) 1999-03-25
ES2217311T3 (es) 2004-11-01
CN1189837A (zh) 1998-08-05
EP0832900B1 (en) 2004-03-03
LT98004A (en) 1998-10-26
DK0832900T3 (da) 2004-06-21
BR9609235A (pt) 1999-12-21
HK1014965A1 (en) 1999-10-08
WO1996040740A1 (en) 1996-12-19
JP4082522B2 (ja) 2008-04-30
BRPI9609235B8 (pt) 2016-09-27
EP0832900A4 (en) 1999-10-06
AU724781B2 (en) 2000-09-28
ATE260933T1 (de) 2004-03-15

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