KR850001772A - 성장 호르몬 방출펩티드의 제조방법 - Google Patents
성장 호르몬 방출펩티드의 제조방법 Download PDFInfo
- Publication number
- KR850001772A KR850001772A KR1019840004730A KR840004730A KR850001772A KR 850001772 A KR850001772 A KR 850001772A KR 1019840004730 A KR1019840004730 A KR 1019840004730A KR 840004730 A KR840004730 A KR 840004730A KR 850001772 A KR850001772 A KR 850001772A
- Authority
- KR
- South Korea
- Prior art keywords
- resin
- peptide
- iii
- acid
- asparaginyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- 102100033367 Appetite-regulating hormone Human genes 0.000 title 1
- 108010077689 gamma-aminobutyryl-2-methyltryptophyl-2-methyltryptophyl-2-methyltryptophyl-lysinamide Proteins 0.000 title 1
- 239000011347 resin Substances 0.000 claims 12
- 229920005989 resin Polymers 0.000 claims 12
- 108090000765 processed proteins & peptides Proteins 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims 3
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims 3
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000002849 D-tyrosine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical group 0.000 claims 2
- -1 aspartyl Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 2
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims 1
- 125000001379 D-asparagine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C(N([H])[H])=O 0.000 claims 1
- 125000002237 D-aspartyl group Chemical group [H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])C(*)=O 0.000 claims 1
- 125000004077 D-glutamic acid group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 claims 1
- 125000002437 D-histidyl group Chemical group N[C@@H](C(=O)*)CC=1N=CNC1 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229960004717 insulin aspart Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- VOMXSOIBEJBQNF-UTTRGDHVSA-N novorapid Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CS)NC(=O)[C@H](CS)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CC=C(O)C=C1.C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 VOMXSOIBEJBQNF-UTTRGDHVSA-N 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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 factors (GH-RF) (Somatoliberin)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (2)
- C-말단보호 아미노산을 커플링시약존재하에 수지에 결합시키고, 불활성 용매로 세척하고, 산 존재하에 탈보호하고, 이 과정을 구조식(Ⅰ),(Ⅱ) 및 (Ⅲ)에서 정의한 바와 같이 보호된 아미노산에 대해 펩티드의 C-말단으로부터 단계적으로 반복하고, 최종적으로 상기 수지가 BHA 또는 p-ME-BHA인 경우 산 존재하에 수지로부터 펩티드를 분리시켜 구조식(Ⅰ),(Ⅱ) 및 (Ⅲ)의 펩티드를 얻거나, 상기 수지가 클로로메틸화 또는 하이드록시메틸화수지인 경우 암모니아, 알킬아민 또는 디알킬아민을 사용하여 수지로부터 펩티드를 분리시킨 다음 산을 사용하여 탈보호시켜 구조식(Ⅰ),(Ⅱ) 및 (Ⅲ)의 펩티드를 얻거나, 상기 수지가 클로로메틸화 또는 하이드록시메틸화 수지인 경우엔 산 존재하에 수지로부터 펩티드를 분리시켜 구조식(Ⅰ),(Ⅱ) 또는 (Ⅲ)의 펩티드를 얻거나, R3가 C1~6직쇄 또는 분지쇄알킬기이고 상기 수지가 클로로메틸화 또는 하이드록시메틸화 수지인 경우엔 염기와 R3OH 알콜존재하에 수지로부터 펩티드를 분리한 후 산 처리하여 구조식(Ⅰ),(Ⅱ) 또는 (Ⅲ)의 펩티드를 얻는 것으로 구성된 하기구조식(Ⅰ),(Ⅱ) 또는 (Ⅲ)의 펩티드 및 그의 제약상 허용되는 염의 제조방법.상기식들에서 R1은 수소 또는 C1-C6직쇄 또는 분지쇄알카노일이며, R2는 NR3N4또는 OR3이며, R3와 R4는 수소, C1~6직쇄 또는 분지쇄알킬기로 구성된 군으로부터 선택되며, A는 티로실, D-티로실, 히스티딜, D-히스티딜이며, B는 알라닐, D-알라닐, 로이실, D-로이실이며, C는 아스파르틸, D-아스파르틸, 글루타밀 및 D-글루타밀이며, X는 아스파라기닐 또는 D-아스파라기닐이며, Y는 노르로이실 또는 메티오닐이며, 단 R1이 수소이고 B가 알라닐이고 C가 아스파트틸이며 X가 아스파라기닐이고 Y가 메티오닐인 경우 A는 구조식(Ⅰ),(Ⅱ) 또는 (Ⅲ)에서 티로실일 수 없으며 R1이 수소, 또는 알카노일이고, B가 알라닐이고 C가 아스파르틸이고, X가 아스파라기닐이고, Y가 메티오닐인 경우 구조식(Ⅰ),(Ⅱ) 또는 (Ⅲ)에서 A는 페닐알라닌, 트리프로필, 히스티딜 또는 D-티로실일 수 없다.
- 제9항에 있어서 상기 펩티드가 하기 구조식을 가짐을 특징으로 하는 펩티드의 제조방법.허용되는 염.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52206783A | 1983-08-10 | 1983-08-10 | |
| US522067 | 1983-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850001772A true KR850001772A (ko) | 1985-04-01 |
Family
ID=24079327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004730A KR850001772A (ko) | 1983-08-10 | 1984-08-08 | 성장 호르몬 방출펩티드의 제조방법 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0136475B1 (ko) |
| JP (1) | JPH0684400B2 (ko) |
| KR (1) | KR850001772A (ko) |
| AT (1) | ATE60062T1 (ko) |
| AU (1) | AU575843B2 (ko) |
| CA (1) | CA1268898A (ko) |
| DE (1) | DE3483931D1 (ko) |
| DK (1) | DK167361B1 (ko) |
| ES (2) | ES8606400A1 (ko) |
| FI (1) | FI86432C (ko) |
| HK (1) | HK73692A (ko) |
| IL (1) | IL72630A (ko) |
| NO (1) | NO165804C (ko) |
| NZ (1) | NZ209078A (ko) |
| PT (1) | PT79055B (ko) |
| SG (1) | SG28692G (ko) |
| ZA (1) | ZA846191B (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518586A (en) * | 1983-01-13 | 1985-05-21 | The Salk Institute For Biological Studies | GRF Analogs III |
| IL70530A (en) * | 1983-01-13 | 1986-09-30 | Salk Inst For Biological Studi | Synthetic peptides having growth hormone releasing factor activity and compositions containing them |
| PT79094B (en) * | 1983-08-29 | 1986-08-14 | Salk Inst For Biological Studi | Grf analogs |
| US4528190A (en) * | 1983-10-25 | 1985-07-09 | The Salk Institute For Biological Studies | GRF Analogs IV |
| DE3436819A1 (de) * | 1984-10-06 | 1986-04-17 | Hoechst Ag, 6230 Frankfurt | Arzneimittel mit grf-wirkung |
| CA1271600A (en) * | 1985-01-07 | 1990-07-10 | David Howard Coy | Growth hormone-releasing peptides and method of treating mammals therewith |
| EP0193910A3 (en) * | 1985-03-06 | 1988-11-23 | Sumitomo Pharmaceuticals Company, Limited | Synthesis of a derivative of grf and intermediate peptides |
| FR2594832B1 (fr) * | 1986-02-24 | 1990-05-25 | Sanofi Sa | Derives du facteur de liberation de l'hormone de croissance (grf) possedant des aminoacides modifies |
| FR2599038B1 (fr) * | 1986-05-26 | 1990-06-29 | Sanofi Sa | Procede de preparation de nonacosapeptides et peptides intermediaires |
| DE3742633A1 (de) * | 1987-12-16 | 1989-06-29 | Hoechst Ag | Peptide mit beeinflussender wirkung auf die hypophyse von saeugern |
| US5565606A (en) * | 1986-10-21 | 1996-10-15 | Hoechst Aktiengesellschaft | Synthesis of peptide aminoalkylamides and peptide hydrazides by the solid-phase method |
| IL86102A (en) * | 1987-05-11 | 1994-04-12 | Univ Tulane | Alkylated peptides that release growth hormone and their use |
| US5002931A (en) * | 1987-05-22 | 1991-03-26 | The Salk Institute For Biological Studies | GRF analogs VII |
| 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 |
| US4959352A (en) * | 1987-09-18 | 1990-09-25 | Hoffmann-La Roche Inc. | Cyclic growth hormone releasing factor analogs and method for the manufacture thereof |
| ES2054754T3 (es) * | 1987-09-18 | 1994-08-16 | Hoffmann La Roche | Analogos ciclicos del grf. |
| US5756458A (en) * | 1989-06-16 | 1998-05-26 | Pharmacia & Upjohn Company | Stabilized potent GRF analogs |
| DK0477217T3 (da) * | 1989-06-16 | 1995-04-03 | Upjohn Co | Stabiliserede, potente GRF-analoge |
| 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 |
|---|---|---|---|---|
| NZ204456A (en) * | 1982-06-16 | 1987-05-29 | Salk Inst For Biological Studi | Synthetic pancreatic growth-hormone releasing factor |
| US4563352A (en) * | 1982-10-04 | 1986-01-07 | The Salk Institute For Biological Studies | Human pancreatic GRF |
| IL70530A (en) * | 1983-01-13 | 1986-09-30 | Salk Inst For Biological Studi | Synthetic peptides having growth hormone releasing factor activity and compositions containing them |
| US4518586A (en) * | 1983-01-13 | 1985-05-21 | The Salk Institute For Biological Studies | GRF Analogs III |
| ATE53220T1 (de) * | 1983-03-07 | 1990-06-15 | Hoffmann La Roche | Polypeptide. |
-
1984
- 1984-07-31 AU AU31334/84A patent/AU575843B2/en not_active Ceased
- 1984-08-01 NZ NZ209078A patent/NZ209078A/xx unknown
- 1984-08-06 DE DE8484109312T patent/DE3483931D1/de not_active Expired - Lifetime
- 1984-08-06 EP EP84109312A patent/EP0136475B1/en not_active Expired - Lifetime
- 1984-08-06 AT AT84109312T patent/ATE60062T1/de not_active IP Right Cessation
- 1984-08-08 CA CA000460517A patent/CA1268898A/en not_active Expired - Lifetime
- 1984-08-08 KR KR1019840004730A patent/KR850001772A/ko not_active Application Discontinuation
- 1984-08-09 DK DK384084A patent/DK167361B1/da not_active IP Right Cessation
- 1984-08-09 FI FI843141A patent/FI86432C/fi not_active IP Right Cessation
- 1984-08-09 ZA ZA846191A patent/ZA846191B/xx unknown
- 1984-08-09 NO NO843195A patent/NO165804C/no unknown
- 1984-08-09 PT PT79055A patent/PT79055B/pt not_active IP Right Cessation
- 1984-08-09 IL IL72630A patent/IL72630A/xx not_active IP Right Cessation
- 1984-08-09 ES ES535032A patent/ES8606400A1/es not_active Expired
- 1984-08-10 JP JP59166634A patent/JPH0684400B2/ja not_active Expired - Lifetime
-
1985
- 1985-07-31 ES ES545760A patent/ES8608540A1/es not_active Expired
-
1992
- 1992-03-09 SG SG286/92A patent/SG28692G/en unknown
- 1992-09-24 HK HK736/92A patent/HK73692A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI86432B (fi) | 1992-05-15 |
| JPS6057000A (ja) | 1985-04-02 |
| CA1268898A (en) | 1990-05-08 |
| EP0136475A2 (en) | 1985-04-10 |
| EP0136475A3 (en) | 1987-03-11 |
| FI843141A (fi) | 1985-02-11 |
| PT79055B (en) | 1986-08-12 |
| DK167361B1 (da) | 1993-10-18 |
| AU3133484A (en) | 1985-02-14 |
| AU575843B2 (en) | 1988-08-11 |
| JPH0684400B2 (ja) | 1994-10-26 |
| IL72630A (en) | 1988-11-30 |
| IL72630A0 (en) | 1984-11-30 |
| NO165804B (no) | 1991-01-02 |
| ES8606400A1 (es) | 1986-05-01 |
| ES8608540A1 (es) | 1986-07-16 |
| ES545760A0 (es) | 1986-07-16 |
| NZ209078A (en) | 1989-03-29 |
| HK73692A (en) | 1992-10-02 |
| FI843141A0 (fi) | 1984-08-09 |
| DE3483931D1 (de) | 1991-02-21 |
| ES535032A0 (es) | 1986-05-01 |
| PT79055A (en) | 1984-09-01 |
| ATE60062T1 (de) | 1991-02-15 |
| ZA846191B (en) | 1985-03-27 |
| DK384084A (da) | 1985-02-11 |
| NO165804C (no) | 1991-04-10 |
| SG28692G (en) | 1992-05-15 |
| DK384084D0 (da) | 1984-08-09 |
| NO843195L (no) | 1985-02-11 |
| FI86432C (fi) | 1992-08-25 |
| EP0136475B1 (en) | 1991-01-16 |
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