FI91075B - Förfarande för framställning av nya terapeutiskt användbara peptider - Google Patents

Förfarande för framställning av nya terapeutiskt användbara peptider Download PDF

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Publication number
FI91075B
FI91075B FI883388A FI883388A FI91075B FI 91075 B FI91075 B FI 91075B FI 883388 A FI883388 A FI 883388A FI 883388 A FI883388 A FI 883388A FI 91075 B FI91075 B FI 91075B
Authority
FI
Finland
Prior art keywords
phe
peptide
nal
pro
cit
Prior art date
Application number
FI883388A
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English (en)
Finnish (fi)
Other versions
FI883388A (sv
FI91075C (sv
FI883388A0 (sv
Inventor
Andrew V Schally
Sandor Bajusz
Original Assignee
Asta Medica Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asta Medica Ag filed Critical Asta Medica Ag
Publication of FI883388A0 publication Critical patent/FI883388A0/sv
Publication of FI883388A publication Critical patent/FI883388A/sv
Priority to FI933629A priority Critical patent/FI101884B/sv
Application granted granted Critical
Publication of FI91075B publication Critical patent/FI91075B/sv
Publication of FI91075C publication Critical patent/FI91075C/sv

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04Linear peptides containing only normal peptide links
    • C07K7/23Luteinising hormone-releasing hormone [LHRH]; Related peptides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18Feminine contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00Peptide or protein sequence
    • Y10S930/01Peptide or protein sequence
    • Y10S930/11Gonadotropin; related peptides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00Peptide or protein sequence
    • Y10S930/01Peptide or protein sequence
    • Y10S930/12Growth hormone, growth factor other than t-cell or b-cell growth factor, and growth hormone releasing factor; related peptides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00Peptide or protein sequence
    • Y10S930/01Peptide or protein sequence
    • Y10S930/13Luteinizing hormone-releasing hormone; related peptides

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Endocrinology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Reproductive Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (7)

1. Förfarande för framställning av en terapeutiskt användbar peptid med formeln 5 X-R1-R2-R3-Ser-Tyr-R6-Leu-Arg-Pro-R10-NH2 (I) i vilken X är en acylgrupp, som har erh&llits frän ogrenade 10 eller grenade kedjor av alifatlska eller alicykliska kar-boxylsyror som innehäller 1-7 kolatomer, eller en kar-bamoylgrupp, R1 är D- eller L-Pro, D- eller L-A3-Pro, D-Phe, D-Phe(4-H1), D-Ser, D-Thr, D-Ala, D-Nal(l) eller 15 D-Nal(2), R2 är D-Phe eller D-Phe(4-Hl), R3 är D-Trp, D-Phe, D-Pal(3), D-Nal(l) eller D-Nal(2), R6 är D-Cit, D-Hci, D-Cit(Q) eller D-Hci(Q) och 20 R10 är Gly eller D-Ala, varvid Hl är fluor, klor eller brom och Q är C1.3-alkyl, eller för framställning av ett farmaceutiskt godtagbart syraadditionssalt därav, kännetecknat därav, att 25 motsvarande peptidfragment kondenseras med hjälp av 1 peptidkeml vanlig fragmentkondensation eller peptiden bildas gradvis av utgängsaminosyror med hjälp av i peptidkemi vanlig fragmentkondensation eller 1 peptiden med formeln I, i vilken R6 är D-Orn el-30 ler D-Lys, förvandlas den fria aminogruppen av D-Orn eller D-Lys genom att bringa den att reagera med alkalicya-nat eller med en förening som alstrar cyanat, eller med C1.3-alkyl-isocyanat tili en ureidogrupp och de erhällna peptiderna acyleras eventuellt och/el-i 35 ler förvandlas tili amider och II 91075 förvandlas eventuellt till fysiologiskt ofarliga syrasalt.
2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att ett gradvist bildande utförs, 5 varvid aminosyran i karboxyländan, glysin eller D-alanin, eller en amid därav, i vilka den stabila a-aminogruppen har skyddats, binds först kovalent pä en för detta ända-mäl konventionell syntetisk bärare, skyddsgruppen i α-amino-gruppen spjälks av, pä den sä erhällna fria ami-10 nogruppen binds den närmast följande skyddade aminosyran via dess karboxylgrupp, därefter spjälks skyddsgruppen i a-amino i denna andra aminosyra av, pä denna binds den närmast följande aminosyran ooh pä detta sätt steg för steg kopplas de övriga aminosyrorna i peptiden som skall 15 syntetiseras i rätt ordning, och när alla aminosyror har kopplats, spjälks den färdiga peptiden frän bäraren och eventuellt spjälks även de närvarande skyddsgrupperna i sidogrupperna av.
3. Förfarande enligt patentkrav 1, känne-20 tecknat därav, att X är en acetyl- eller karba- moylgrupp, R1 är D-Nal(2), D- eller L-Pro, D-Phe eller D-Phe(4-C1), R2 är D-Phe(4-Cl) eller D-Phe(4-F) och R3 är D-Trp eller D-Pal(3).
4. Förfarande enligt nägot av patentkraven 1-3, 25 kännetecknat därav, att X är acetyl, R1 är D-Nal(2) eller D-Phe(4-Cl), R2 är D-Phe(4-Cl), R3 är D-Trp eller D-Pal(3) och R10 är D-Ala.
5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att X är acetyl. 30
6. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att X är karbamoyl.
7. Förfarande enligt nägot av patentkraven 1-6, kännetecknat därav, att R6 är D-Cit eller D-Hci.
FI883388A 1987-07-17 1988-07-15 Förfarande för framställning av nya terapeutiskt användbara peptider FI91075C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI933629A FI101884B (sv) 1987-07-17 1993-08-17 Antagonistpeptider till hormon som frigör luteiniserande hormon (LHRH)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7412687 1987-07-17
US07/074,126 US4800191A (en) 1987-07-17 1987-07-17 LHRH antagonists

Publications (4)

Publication Number Publication Date
FI883388A0 FI883388A0 (sv) 1988-07-15
FI883388A FI883388A (sv) 1989-01-18
FI91075B true FI91075B (sv) 1994-01-31
FI91075C FI91075C (sv) 1994-05-10

Family

ID=22117877

Family Applications (1)

Application Number Title Priority Date Filing Date
FI883388A FI91075C (sv) 1987-07-17 1988-07-15 Förfarande för framställning av nya terapeutiskt användbara peptider

Country Status (18)

Country Link
US (2) US4800191A (sv)
EP (1) EP0299402B1 (sv)
JP (1) JP2944669B2 (sv)
AT (1) ATE90362T1 (sv)
BR (1) BR1100478A (sv)
CA (1) CA1339623C (sv)
DE (3) DE3881592D1 (sv)
DK (1) DK173375B1 (sv)
ES (1) ES2054741T3 (sv)
FI (1) FI91075C (sv)
HK (1) HK21194A (sv)
HU (1) HU206376B (sv)
IE (1) IE62744B1 (sv)
LU (1) LU90425I2 (sv)
LV (1) LV5795B4 (sv)
NL (1) NL990029I2 (sv)
PT (1) PT87998B (sv)
ZA (1) ZA885147B (sv)

Families Citing this family (51)

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US4800191A (en) * 1987-07-17 1989-01-24 Schally Andrew Victor LHRH antagonists
US5171835A (en) * 1988-10-21 1992-12-15 The Administrators Of The Tulane Educational Fund LHRH antagonists
US5169932A (en) * 1989-10-30 1992-12-08 The Salk Institute For Biological Studies Gnrh analogs
US5064939A (en) * 1990-02-06 1991-11-12 The Salk Institute For Biological Studies Cyclic gnrh antagonists
HU208158B (en) * 1990-02-20 1993-08-30 Syntex Inc Process for the synthesis of 1h-rh analogs by temporary protection
US5516887A (en) * 1991-04-25 1996-05-14 Romano Deghenghi Luteinizing hormone releasing hormone antagonist peptides
DE4117507A1 (de) * 1991-05-24 1992-11-26 Schering Ag Verfahren zur herstellung von n(pfeil hoch)6(pfeil hoch)-substituierten lysin-derivaten
CH683149A5 (fr) * 1991-07-22 1994-01-31 Debio Rech Pharma Sa Procédé pour la préparation de microsphères en matériau polymère biodégradable.
WO1993003752A1 (en) * 1991-08-19 1993-03-04 The Arizona Board Of Regents On Behalf Of The University Of Arizona Decapeptide having dopamine stimulating activity
US6468959B1 (en) * 1991-12-05 2002-10-22 Alfatec-Pharm Gmbh Peroral dosage form for peptide containing medicaments, in particular insulin
BE1005720A3 (fr) * 1992-03-20 1993-12-28 Solvay Procede de synthese peptidique et nouveaux intermediaires de synthese.
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DE4320201A1 (de) * 1993-06-18 1995-01-12 Asta Medica Ag Verwendung von Cetrorelix und weiteren Nona- und Dekapeptiden zur Herstellung eines Arzneimittels zur Bekämpfung von Aids und zur Wachstumsstimulation
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US5550212A (en) * 1993-12-17 1996-08-27 The Administrators Of The Tulane Educational Fund Analogues of hGH-RH(1-29)NH2 having antagonistic activity
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US6407205B1 (en) * 1997-06-04 2002-06-18 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College FSH-releasing peptides
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US7214662B2 (en) 2001-11-27 2007-05-08 Zentaris Gmbh Injectable solution of an LHRH antagonist
CN101647772A (zh) * 2008-08-12 2010-02-17 中国人民解放军军事医学科学院毒物药物研究所 Lhrh拮抗剂类物质的注射用缓释制剂及其制备
EP2379099A1 (en) 2009-01-22 2011-10-26 Maatschap Interne Geneeskunde Rijnstate Method for the prophylaxis or treatment of flushing
CN101863960B (zh) * 2009-04-15 2013-03-06 无锡市凯利药业有限公司 西曲瑞克的制备方法
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JP2014502282A (ja) 2010-12-06 2014-01-30 アストロン リサーチ リミテッド 安定な使用準備済みセトロレリックス注射液
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CN112175043A (zh) * 2020-10-12 2021-01-05 湖南津安生物科技有限公司 一种改进的鲑鱼促性腺激素释放激素的固相合成方法

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Also Published As

Publication number Publication date
US5198533A (en) 1993-03-30
BR1100478A (pt) 2000-03-14
FI883388A (sv) 1989-01-18
IE882185L (en) 1989-01-17
HUT47311A (en) 1989-02-28
US4800191A (en) 1989-01-24
LV5795A4 (lv) 1997-02-20
JPS6434997A (en) 1989-02-06
DK395688A (da) 1989-01-18
DK173375B1 (da) 2000-09-11
FI91075C (sv) 1994-05-10
DE19975052I2 (de) 2009-01-02
HK21194A (en) 1994-03-18
JP2944669B2 (ja) 1999-09-06
DE3881592D1 (de) 1993-07-15
LV5795B4 (lv) 1997-08-20
HU206376B (en) 1992-10-28
EP0299402B1 (de) 1993-06-09
EP0299402A2 (de) 1989-01-18
ZA885147B (en) 1989-04-26
PT87998A (pt) 1989-06-30
DK395688D0 (da) 1988-07-15
NL990029I2 (nl) 2000-03-01
DE3823590A1 (de) 1989-01-26
NL990029I1 (nl) 1999-12-01
CA1339623C (en) 1998-01-06
ES2054741T3 (es) 1994-08-16
LU90425I2 (fr) 1999-10-04
PT87998B (pt) 1995-03-01
FI883388A0 (sv) 1988-07-15
ATE90362T1 (de) 1993-06-15
EP0299402A3 (en) 1990-06-06
IE62744B1 (en) 1995-02-22

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