KR850003417A - 폴리펩티드의 제조방법 - Google Patents
폴리펩티드의 제조방법 Download PDFInfo
- Publication number
- KR850003417A KR850003417A KR1019830005067A KR830005067A KR850003417A KR 850003417 A KR850003417 A KR 850003417A KR 1019830005067 A KR1019830005067 A KR 1019830005067A KR 830005067 A KR830005067 A KR 830005067A KR 850003417 A KR850003417 A KR 850003417A
- Authority
- KR
- South Korea
- Prior art keywords
- gln
- ala
- leu
- arg
- ser
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims 8
- 238000000034 method Methods 0.000 title claims 2
- 229920001184 polypeptide Polymers 0.000 title 1
- 102000004196 processed proteins & peptides Human genes 0.000 title 1
- 125000006239 protecting group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 239000011347 resin Substances 0.000 claims 4
- 229920005989 resin Polymers 0.000 claims 4
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- -1 2-chlorobenzyloxy Chemical group 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/60—Growth hormone-releasing factor [GH-RF], i.e. somatoliberin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/827—Proteins from mammals or birds
- Y10S530/843—Digestive system
- Y10S530/845—Pancreas
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/12—Growth hormone, growth factor other than t-cell or b-cell growth factor, and growth hormone releasing factor; related peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Gastroenterology & Hepatology (AREA)
- Analytical Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- External Artificial Organs (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Prostheses (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Machine Tool Sensing Apparatuses (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- (a) 1개 이상의 보호기를 갖는 펩티드와 다음 일반식(II)의 펩티드로 구성되고, 또 (b) 다음 일반식(II)의 펩티드로부터 보호기 또는 보호기들 또는 연결결합을 잘라내고, 또 (c) 필요한 경우 수득펩티드를 비독성 산부가염으로 전환시키는 단계로 구성되는 다음 일반식(I)의 화합물을 제조하는 방법.H-Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-D-Ala-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-Gln-Gln-Gly-Glu-Ser-Asn-Gln-Glu-Arg-Gly-R40-y (Ⅰ)X1-Tyr(X2)-Ala-Asp(X3)-Ala-Ile-Phe-Thr(X4)-Asn(X5)-Ser(X4)-Tyr(X2)-Arg(X6)-Lys(X7)-Val-Leu-D-Ala-Gln(X5)-Leu-Ser(X4)-Ala-Arg(X6)-Lys(X7)-Leu-Leu-Gln(X5)-Asp(X3)-Ile-Met-Ser(X4)-Arg(X6)-Gln(X5)-Gln(X5)-Gln(X5)-Gly-Glu(X3)-Ser(X4)-Asn(X5)-Gln(X5)-Glu(X3)-Arg(X6)-Gly-R40-X8(Ⅱ)상기 일반식(I) 및 (II)에서, R40은 Ala 또는 탈 -R40이고, 또 Y는 C-말단에서 아미노산개체의 카복시잔기를 나타내며, -COOR1, -CR1O, -CONHNHR1-CON(R1)(R2) 또는 -CH2OR1으로서, 이때 R1및 R2는 저급알킬 또는 수소이고, X1, X2, X3, X4, X5, X6및 X7은 각각 수소 또는 보호기이며, 또 X8은 보호기 또는 수지지지체의 연결 결합손중 하나이거나 또는 C-말단개체가 카복시잔기 Y를 갖는 경우는 말-X8이다.
- 제1항에 있어서, R40가 Ala인 일반식(I) 화합물의 제조방법.
- 제1항 또는 제2항에 있어서, Y가 CONH2인 일반식(I) 화합물의 제조방법.
- (a) 1개 이상의 보호기를 갖는 펩티드와 다음 일반식(II)의 화합물로 형성되고, 또 (b) 일반식(II)의 펩티드로부터 보호기 또는 보호기들 또는 연결 결합체을 제거하고, 또 (c) 필요한 경우, 수득펩티드를 비독성 부가염으로 전환시키는 단계로 구성되는 다음 일반식(I)의 화합물을 제조하는 방법.H-Tyr-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-R15-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-Gln-Gln-Gly-Y (Ⅰ)X1-Tyr(X2)-Ala-Asp(X3)-Ala-Ile-Phe-Thr(X4)-Asn(X5)-Ser(X4)-Tyr(X2)-Arg(X6)-Lys(X7)-Val-Leu-R15-Gln(X5)-Leu-Ser(X4)-Ala-Arg(X6)-Lys(X7)-Leu-Leu-Gln(X5)-Asp(X3)-Ile-Met-Ser(X4)-Arg(X6)-Gln(X5)-Gln(X5)-Gly-X8(Ⅱ)상기 일반식(I), (II)에서, R15는 Gly 또는 D-Ala이고, 개체 23 내지 32의 어느것 또는 모두는 제거될 수도 있으며, 또 Y는 C-말단에서 아미노산 개체의 카복실잔기를 나타내며 R1및 R2가 저급알킬 또는 수소인 -CON(R1)(R2)레디칼이고, X1, X2, X3, X4, X5, X6및 X7은 각각 수소이거나 또는 보호기이며, 또 X8은 보호기 또는 수지지지체의 연결 결합손이고, C-말단에서의 개체가 카복시잔기 Y를 갖는 경우는 탈-X8이다.
- 제4항에 있어서, 개체 30 내지 33가 삭제된 일반식(I) 화합물의 제조방법.
- 제4항에 있어서, 개체 28 내지 32가 삭제된 일반식(I) 화합물의 제조방법.
- 제5항 또는 제6항에 있어서, Y가 -CONH2인 일반식(I) 화합물의 제조방법.
- 제5항 또는 제7항중 어느 하나에 있어서, R15가 D-Ala인 일반식(I) 화합물의 제조방법.
- 제1항 내지 제4항중 어느 하나에 있어서, X1이 수소 또는 α-아미노보호기이고;X2가 수소 또는 Jyr의 페놀성 하이드록시기의 보호기이며;X3가 수소 또는 Asp 또는 Glu의 카복시기의 보호기이고;X4가 수소 또는 Ser 및 의 알콜성 하이드록시기의 보호기이며; X5가 수소 또는 AsN 또는 Gln의 보호기이고; X6는 수소 또는 ArG의 구아니디노기의 보호기이며; X7은 수소 또는 Lys의 측쇄아미노기의 보호기이고; 또 1개 이상의 X-기가 보호기이거나 또는 수지지지체를 일반식(I) 화합물의 제조방법.
- 제9항에 있어서, X1이 Boc이고, X2가 DCB이며, X3가 OBzl이고, X4가 Bzl이며, X5가 Xan이고, X6가 TOS이며, X7이 2-클로로 벤실옥시카보닐이고, X8가 -NH-수지지지체인 일반식(I)의 화합물의 제조 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US432663 | 1982-10-04 | ||
US06/432,663 US4563352A (en) | 1982-10-04 | 1982-10-04 | Human pancreatic GRF |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850003417A true KR850003417A (ko) | 1985-06-17 |
KR900006712B1 KR900006712B1 (ko) | 1990-09-17 |
Family
ID=23717095
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830005067A KR900006712B1 (ko) | 1982-10-04 | 1983-10-26 | 폴리펩티드의 제조방법 |
Country Status (25)
Country | Link |
---|---|
US (1) | US4563352A (ko) |
EP (1) | EP0105759B1 (ko) |
JP (1) | JPS59501951A (ko) |
KR (1) | KR900006712B1 (ko) |
AT (1) | ATE24919T1 (ko) |
AU (1) | AU566180B2 (ko) |
CA (1) | CA1243016A (ko) |
DE (1) | DE3369144D1 (ko) |
DK (1) | DK269284D0 (ko) |
ES (1) | ES8606399A1 (ko) |
FI (1) | FI83660C (ko) |
GR (1) | GR79698B (ko) |
HU (1) | HU191263B (ko) |
IE (1) | IE56175B1 (ko) |
IL (1) | IL69897A (ko) |
MX (1) | MX7701E (ko) |
NO (1) | NO167866C (ko) |
NZ (1) | NZ205745A (ko) |
PH (1) | PH20333A (ko) |
PT (1) | PT77453B (ko) |
RO (1) | RO91186B (ko) |
SU (1) | SU1426455A3 (ko) |
WO (1) | WO1984001379A1 (ko) |
YU (1) | YU45575B (ko) |
ZA (1) | ZA837208B (ko) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4728726A (en) * | 1982-10-04 | 1988-03-01 | The Salk Institute For Biological Studies | GRF analogs IIIb |
US4703035A (en) * | 1982-10-04 | 1987-10-27 | The Salk Institute For Biological Studies | Human pancreatic GRF amidated fragments |
US4581168A (en) * | 1983-02-21 | 1986-04-08 | Sanofi | Synthesis of hpGRF (Somatocrinin) in liquid phase and intermediate peptides |
ZA844380B (en) * | 1983-07-05 | 1985-01-30 | Salk Inst For Biological Studi | Dna encoding a grf precursor |
AU575843B2 (en) * | 1983-08-10 | 1988-08-11 | The Administrators Of The Tulane Eductional Fund | Growth hormone releasing peptides |
US4617149A (en) * | 1983-09-21 | 1986-10-14 | Eli Lilly And Company | Growth hormone release factor analogs |
US4528190A (en) * | 1983-10-25 | 1985-07-09 | The Salk Institute For Biological Studies | GRF Analogs IV |
FR2567524B1 (fr) * | 1984-07-10 | 1987-11-27 | Sanofi Sa | Procede de synthese de la somatocrinine en phase liquide et peptides intermediaires |
US4649131A (en) * | 1984-09-24 | 1987-03-10 | Hoffmann-La Roche Inc. | Growth hormone releasing factor analogs |
EP0189673B1 (en) * | 1984-12-24 | 1990-09-26 | Sumitomo Pharmaceuticals Company, Limited | Stable growth hormone releasing factor preparation |
US4734399A (en) * | 1985-08-06 | 1988-03-29 | Hoffmann-La Roche Inc. | Growth hormone releasing factor analogs |
US4880778A (en) * | 1986-05-12 | 1989-11-14 | Eastman Kodak Company | Combinations having synergistic growth hormone releasing activity and methods for use thereof |
FR2599038B1 (fr) * | 1986-05-26 | 1990-06-29 | Sanofi Sa | Procede de preparation de nonacosapeptides et peptides intermediaires |
IL84758A (en) * | 1987-01-13 | 1992-03-29 | Salk Inst For Biological Studi | Peptides stimulating the release of pituitary growth hormone in fish and amphibians,and pharmaceutical compositions containing them |
US4839344A (en) * | 1987-06-12 | 1989-06-13 | Eastman Kodak Company | Polypeptide compounds having growth hormone releasing activity |
US4801456A (en) * | 1987-07-09 | 1989-01-31 | International Minerals & Chemical Corp. | Growth hormone-releasing factor analogs |
USRE33699E (en) * | 1987-07-09 | 1991-09-24 | International Minerals & Chemical Corp. | Growth hormone-releasing factor analogs |
US4880777A (en) * | 1987-09-01 | 1989-11-14 | Eastman Kodak Company | Synthetic peptides having growth hormone releasing activity |
EP0400051B1 (en) * | 1988-01-28 | 1995-05-10 | Polygen Holding Corporation | Polypeptide compounds having growth hormone releasing activity |
US5043322A (en) * | 1988-07-22 | 1991-08-27 | The Salk Institute For Biological Studies | Cyclic GRF analogs |
US5153175A (en) * | 1989-05-25 | 1992-10-06 | University Of Tennesee Research Corporation | Method of inducing sleep with GHRH complementary peptide compositions |
US5756458A (en) * | 1989-06-16 | 1998-05-26 | Pharmacia & Upjohn Company | Stabilized potent GRF analogs |
AU656144B2 (en) * | 1990-06-29 | 1995-01-27 | F. Hoffmann-La Roche Ag | Histidine substituted growth hormone releasing factor analogs |
DK0490249T3 (da) * | 1990-12-10 | 1995-05-29 | Hoffmann La Roche | Fremgangsmåde til enzymatisk fremstilling af GRF(1-44)-NH2 |
WO1992018531A1 (en) * | 1991-04-09 | 1992-10-29 | F. Hoffmann-La Roche Ag | Growth hormone releasing factor analogs |
US5246920A (en) * | 1992-06-15 | 1993-09-21 | University Of South Florida | Treatment of hyperprolactinemia |
US5811074A (en) * | 1992-06-29 | 1998-09-22 | University Of South Florida | Method of diagnosing pituitary dependent growth hormone deficiency |
US5631225A (en) * | 1994-10-13 | 1997-05-20 | Novo Nordisk A/S | Pharmaceutical formulation |
EP0880969A1 (en) * | 1997-05-28 | 1998-12-02 | Applied Research Systems ARS Holdings N.V. | Pharmaceutical compositions of peptides having low solubility in physiological medium |
EP0922446A1 (en) * | 1997-12-03 | 1999-06-16 | Applied Research Systems Ars Holding N.V. | Solution-phase site-specific preparation of GRF-PEG conjugates |
BR0206919A (pt) * | 2001-02-02 | 2004-07-06 | Conjuchem Inc | Derivados de fator de liberação de hormÈnio de crescimento de longa duração |
CN1688696A (zh) * | 2002-09-18 | 2005-10-26 | 蒙特利尔大学医疗中心 | Ghrh类似物 |
US20090088380A1 (en) * | 2007-07-12 | 2009-04-02 | Pierrette Gaudreau | Ghrh analogs and therapeutic uses thereof |
CN107936090B (zh) * | 2017-12-08 | 2021-09-24 | 陕西慧康生物科技有限责任公司 | 一种低成本合成ARK-Cu的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3664925A (en) * | 1970-02-20 | 1972-05-23 | Martin Sonenberg | Clinically active bovine growth hormone fraction |
US3904753A (en) * | 1970-02-20 | 1975-09-09 | Research Corp | Clinically active bovine growth hormone fraction |
US3853833A (en) * | 1971-04-27 | 1974-12-10 | Hormone Res Foundation | Synthetic human growth-promoting and lactogenic hormones and method of producing same |
US4056520A (en) * | 1972-03-31 | 1977-11-01 | Research Corporation | Clinically active bovine growth hormone fraction |
PH14681A (en) * | 1977-11-30 | 1981-11-10 | Pfizer | Phenylglycinamides useful in the treatment of ischaemic heart disease |
-
1982
- 1982-10-04 US US06/432,663 patent/US4563352A/en not_active Expired - Lifetime
-
1983
- 1983-09-26 NZ NZ205745A patent/NZ205745A/en unknown
- 1983-09-27 ZA ZA837208A patent/ZA837208B/xx unknown
- 1983-10-03 PH PH29648A patent/PH20333A/en unknown
- 1983-10-03 WO PCT/US1983/001564 patent/WO1984001379A1/en active IP Right Grant
- 1983-10-03 IE IE2333/83A patent/IE56175B1/en not_active IP Right Cessation
- 1983-10-03 ES ES526201A patent/ES8606399A1/es not_active Expired
- 1983-10-03 JP JP83503459A patent/JPS59501951A/ja active Pending
- 1983-10-03 AU AU21269/83A patent/AU566180B2/en not_active Expired
- 1983-10-03 GR GR72605A patent/GR79698B/el unknown
- 1983-10-03 HU HU8497A patent/HU191263B/hu unknown
- 1983-10-04 PT PT77453A patent/PT77453B/pt not_active IP Right Cessation
- 1983-10-04 AT AT83306008T patent/ATE24919T1/de not_active IP Right Cessation
- 1983-10-04 EP EP83306008A patent/EP0105759B1/en not_active Expired
- 1983-10-04 MX MX831019U patent/MX7701E/es unknown
- 1983-10-04 CA CA000438354A patent/CA1243016A/en not_active Expired
- 1983-10-04 DE DE8383306008T patent/DE3369144D1/de not_active Expired
- 1983-10-04 YU YU200083A patent/YU45575B/sh unknown
- 1983-10-04 IL IL69897A patent/IL69897A/xx not_active IP Right Cessation
- 1983-10-26 KR KR1019830005067A patent/KR900006712B1/ko not_active IP Right Cessation
-
1984
- 1984-05-30 FI FI842166A patent/FI83660C/fi not_active IP Right Cessation
- 1984-05-30 NO NO84842148A patent/NO167866C/no not_active IP Right Cessation
- 1984-05-30 DK DK269284A patent/DK269284D0/da not_active Application Discontinuation
- 1984-06-01 RO RO114739A patent/RO91186B/ro unknown
- 1984-06-01 SU SU843750475A patent/SU1426455A3/ru active
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