CA2257381A1 - Method for producing peptides - Google Patents
Method for producing peptidesInfo
- Publication number
- CA2257381A1 CA2257381A1 CA002257381A CA2257381A CA2257381A1 CA 2257381 A1 CA2257381 A1 CA 2257381A1 CA 002257381 A CA002257381 A CA 002257381A CA 2257381 A CA2257381 A CA 2257381A CA 2257381 A1 CA2257381 A1 CA 2257381A1
- Authority
- CA
- Canada
- Prior art keywords
- pro
- peptide
- trp
- formula
- oxo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
A peptide of the formula (I): 5-oxo-Pro-R1-Trp-Ser-R2--R3-R4-Arg-Pro-R6, wherein R1 represents His, Tyr, Trp or p-NH2-Phe, R2 represents Tyr or Phe, R3 represents an optionally substituted Gly or an optionally substituted .alpha.-D-amino acid residue, R4 represents Leu, Ile or Nle, R6 represents (1) Gly-NH-R7, wherein R7 represents a hydrogen atom or an alkyl group which may optionally be substituted with a hydroxyl group, or (2) NH-R8, wherein R8 represents a hydrogen atom, an alkyl group which may optionally be substituted with a hydroxyl group or an ureido group (-NH-CO-NH2), is produced advantageously in an industrial scale by reacting a peptide of the the formula (II): 5-oxo-Pro-R1-Trp-Ser-R2--R3-OH, wherein R1, R2 and R3 have the same meanings as defined above or its salts, with a peptide of the formula (III):
H-R4-R5-Pro-R6, wherein R4 and R6 have the same meaning as defined above and R5 represents Arg which has been protected or its salts, to produce a peptide of the formula (I'): 5-oxo-Pro-R1-Trp-Ser-R2-R3-R4-R5-Pro-R6, wherein RI, R2, R3, R4, R5 and R6 have the same meanings as defined above or its salt, and then subjecting thus obtained peptide (I') to a de-protecting group reaction.
H-R4-R5-Pro-R6, wherein R4 and R6 have the same meaning as defined above and R5 represents Arg which has been protected or its salts, to produce a peptide of the formula (I'): 5-oxo-Pro-R1-Trp-Ser-R2-R3-R4-R5-Pro-R6, wherein RI, R2, R3, R4, R5 and R6 have the same meanings as defined above or its salt, and then subjecting thus obtained peptide (I') to a de-protecting group reaction.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16179196 | 1996-06-21 | ||
JP8-161791 | 1996-06-21 | ||
PCT/JP1997/002097 WO1997048726A1 (en) | 1996-06-21 | 1997-06-19 | Method for producing peptides |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2257381A1 true CA2257381A1 (en) | 1997-12-24 |
CA2257381C CA2257381C (en) | 2007-08-21 |
Family
ID=15741986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002257381A Expired - Lifetime CA2257381C (en) | 1996-06-21 | 1997-06-19 | Method for producing peptides |
Country Status (13)
Country | Link |
---|---|
US (1) | US6211333B1 (en) |
EP (1) | EP0910575B1 (en) |
KR (1) | KR100459978B1 (en) |
CN (1) | CN1129607C (en) |
AT (1) | ATE224912T1 (en) |
AU (1) | AU3189997A (en) |
CA (1) | CA2257381C (en) |
DE (1) | DE69715860T2 (en) |
DK (1) | DK0910575T3 (en) |
ES (1) | ES2184096T3 (en) |
IL (3) | IL163521A0 (en) |
PT (1) | PT910575E (en) |
WO (1) | WO1997048726A1 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6939855B2 (en) | 1997-07-31 | 2005-09-06 | Elan Pharmaceuticals, Inc. | Anti-inflammatory compositions and method |
US6559127B1 (en) | 1997-07-31 | 2003-05-06 | Athena Neurosciences, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
EA006301B1 (en) | 1999-01-22 | 2005-10-27 | Элан Фармасьютикалз, Инк. | Acyl derivatives which treat vla-4 related disorders |
ES2262504T3 (en) * | 1999-01-26 | 2006-12-01 | Elan Pharm Inc | DERIVATIVES OF THE PYROGLUTAMIC ACID AND RELATED COMPOUNDS THAT INHIBIT THE ADHESION OF LEUKOCYTES THROUGH THE VLA-4. |
US6407066B1 (en) | 1999-01-26 | 2002-06-18 | Elan Pharmaceuticals, Inc. | Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4 |
ATE341562T1 (en) * | 1999-06-30 | 2006-10-15 | Takeda Pharmaceutical | METHOD FOR PREPARING LH-RH DERIVATIVES |
TWI281470B (en) | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
TW200307671A (en) | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
NZ537997A (en) * | 2002-07-29 | 2008-04-30 | Aminotech As | Method for recovering peptides/amino acids and oil/fat from one or more protein-containing raw materials, products produced by the method, and use of the products |
DE602006011099D1 (en) | 2005-05-03 | 2010-01-28 | Novetide Ltd | PROCESS FOR THE PREPARATION OF PEPTIDE DERIVATIVES |
US7727996B2 (en) | 2005-09-29 | 2010-06-01 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by VLA-4 |
CA2624450C (en) | 2005-09-29 | 2014-02-04 | Elan Pharmaceuticals, Inc. | Pyrimidinyl amide compounds which inhibit leukocyte adhesion mediated by vla-4 |
TWI389904B (en) | 2006-02-27 | 2013-03-21 | Elan Pharm Inc | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated by vla-4 |
CA2760151A1 (en) | 2009-04-27 | 2010-11-04 | Elan Pharmaceuticals, Inc. | Pyridinone antagonists of alpha-4 integrins |
JP6564539B1 (en) | 2018-09-14 | 2019-08-21 | 長瀬産業株式会社 | Peptide purification method using sulfonic acid compound |
CN113527438A (en) * | 2021-08-30 | 2021-10-22 | 湖南三太药业有限公司 | Method for synthesizing alarelin in full liquid phase |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3947569A (en) * | 1972-04-12 | 1976-03-30 | American Home Products Corporation | Process for preparing the releasing hormone of luteinizing hormone (LH) and of follicle stimulating hormone (FSH), salts and compositions thereof, and intermediates therefor |
US3855198A (en) | 1972-09-29 | 1974-12-17 | American Home Prod | Novel intermediates for synthesis of l-(5-oxoprolyl)-l-histidy-l-tryptophyl-l-seryl-l-tyrosyl-l-glycyl-l-leucyl-l-arginyl-l-prolyl-glycine amide |
JPS49100081A (en) | 1973-01-30 | 1974-09-20 | ||
CA1023350A (en) | 1974-01-21 | 1977-12-27 | Manfred K. Gotz | Derivatives of the lh- and fsh-releasing hormone |
US3997516A (en) * | 1974-07-04 | 1976-12-14 | Takeda Chemical Industries, Ltd. | Method for protecting guanidino group and restoring the same |
DE3163800D1 (en) | 1980-02-12 | 1984-07-05 | Takeda Chemical Industries Ltd | Method for protecting guanidino group and restoring the same |
IT1178775B (en) * | 1983-12-23 | 1987-09-16 | Konzponti Valto Es Hitelbank R | GONADOLIBERINE DERIVATIVES AND PROCEDURE FOR THEIR PREPARATION |
DE68928278T2 (en) | 1988-02-10 | 1998-03-12 | Tap Pharmaceuticals Inc | LHRH ANALOG |
-
1997
- 1997-06-19 KR KR10-1998-0710409A patent/KR100459978B1/en not_active IP Right Cessation
- 1997-06-19 WO PCT/JP1997/002097 patent/WO1997048726A1/en active IP Right Grant
- 1997-06-19 CA CA002257381A patent/CA2257381C/en not_active Expired - Lifetime
- 1997-06-19 ES ES97927386T patent/ES2184096T3/en not_active Expired - Lifetime
- 1997-06-19 DE DE69715860T patent/DE69715860T2/en not_active Expired - Lifetime
- 1997-06-19 AT AT97927386T patent/ATE224912T1/en active
- 1997-06-19 IL IL16352197A patent/IL163521A0/en active IP Right Grant
- 1997-06-19 US US09/202,621 patent/US6211333B1/en not_active Expired - Lifetime
- 1997-06-19 PT PT97927386T patent/PT910575E/en unknown
- 1997-06-19 AU AU31899/97A patent/AU3189997A/en not_active Abandoned
- 1997-06-19 DK DK97927386T patent/DK0910575T3/en active
- 1997-06-19 IL IL12731297A patent/IL127312A0/en not_active IP Right Cessation
- 1997-06-19 CN CN97195678A patent/CN1129607C/en not_active Expired - Lifetime
- 1997-06-19 EP EP97927386A patent/EP0910575B1/en not_active Expired - Lifetime
-
2004
- 2004-08-12 IL IL163521A patent/IL163521A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CN1222916A (en) | 1999-07-14 |
EP0910575A1 (en) | 1999-04-28 |
IL163521A0 (en) | 2005-12-18 |
CN1129607C (en) | 2003-12-03 |
WO1997048726A1 (en) | 1997-12-24 |
CA2257381C (en) | 2007-08-21 |
AU3189997A (en) | 1998-01-07 |
KR20000016798A (en) | 2000-03-25 |
US6211333B1 (en) | 2001-04-03 |
KR100459978B1 (en) | 2005-01-15 |
IL127312A0 (en) | 1999-09-22 |
DE69715860D1 (en) | 2002-10-31 |
DE69715860T2 (en) | 2003-08-07 |
DK0910575T3 (en) | 2003-02-03 |
PT910575E (en) | 2003-02-28 |
ATE224912T1 (en) | 2002-10-15 |
ES2184096T3 (en) | 2003-04-01 |
EP0910575B1 (en) | 2002-09-25 |
IL163521A (en) | 2007-07-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20170619 |