FI89499B - Foerfarande foer framstaellning av terapeutiskt anvaendbar peptid - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbar peptid Download PDFInfo
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- FI89499B FI89499B FI882305A FI882305A FI89499B FI 89499 B FI89499 B FI 89499B FI 882305 A FI882305 A FI 882305A FI 882305 A FI882305 A FI 882305A FI 89499 B FI89499 B FI 89499B
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000002260 hypophysiotrophic effect Effects 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 230000037189 immune system physiology Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- UPXAZUFKXWLNMF-UHFFFAOYSA-N n'-propan-2-ylmethanediimine Chemical compound CC(C)N=C=N UPXAZUFKXWLNMF-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 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
- C07K14/475—Growth factors; Growth regulators
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Claims (8)
1. Förfarande för framställning av en terapeutiskt användbar peptid och giftfria salter av denna, vilken pep- 5 tid har sekvensen (I): (N"Me) Tyr-Ala-Asp-Ala-Ile-Phe-Thr-R>,-Ser-Tyr-Arg-Lys-Val-Leu-R15-Gln-Leu-Ser-Ala-Arg-R2l-Leu-Leu-Gln-Asp-Ile-Nle-R2i,-Arg-NH2, i vilken Rs är Asn, Lys eller Asp, R,s är Gly eller Ala, R21 10 är Lys eller D-Lys, R28 är Asn eller Ser, under förutsätt-ning, att R* är Lys eller Asp och/eller R21 är D-Lys, kännetecknat därav, att (i) enskilda aminosy-ror eller korta peptider kopplas ätminstone delvis medelst ett fastfasförfarande för bildning av en förening innehäl-15 lande ätmistone en skyddsgrupp och med följande formel (II) : X1-(iTMe) Tyr (X2) - A la-Asp (X3) - Ala-I le-Phe-Thr (X4) -R^X8) -Ser (X4) -Tyr (X2) -Arg(X6) -Lys (X7) -Val-Leu-R,5-Gln (Xs) -Leu-Ser (X2) -Ala-Arg (X6) -R21 (X7) -Leu-Leu-Gin(X5) -Asp(X3) -Ile-Nle-2 0 R2S(X4 eller Xs)-Arg (X5) -X9, i vilken (X), (X'), (X2), (X3), (X4), (Xs), (Xft) , (X7) och (Xs) vardera är antingen väte eller en skyddsgrupp och (X9) är en förankrande bindning tili ett harts, (ii) föreningen 25 behandlas med ett lämpligt reagens för avlägsnande av skyddsgruppen eller -grupperna frän nämnda förening med formeln (II) och för spjälkning av denna frän den förankrande bindningen, varvid en peptid med sekvensen (I) bil-das, och, om sä önskas, (iii) bringas den erhällna pepti-30 den att reagera med en lämplig syra eller motsvarande för framställning av ett giftfritt additionssalt av peptiden.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att R8 är Asp.
3. Förfarande enligt patentkravet 1, k ä n n e -35 tecknat därav, att R21 är D-lys. Il ; 33 8 9 4 9 9
4. Förfarande enligt patentkravet 1, kanne-t e c k n a t därav, att R* är Lys.
5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att R28 är Asn. 5
6. Förfarande enligt patentkravet 1, känne tecknat därav, att peptidens formel är en av föl-jande: [N'MeTyr1, Asp8, Ala15, Nle27, Asn28]-hGRF (1-29)-NH2, [NaMeTyr‘, Lys8, Ala15, Nle27, Asn28]-hGRF (1-29)-NH2 och 10 [NaMeTyr‘, D-Lys21, Nle27]-hGRF (1-29)-NH2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5323587 | 1987-05-22 | ||
| US07/053,235 US5002931A (en) | 1987-05-22 | 1987-05-22 | GRF analogs VII |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI882305A0 FI882305A0 (fi) | 1988-05-17 |
| FI882305A FI882305A (fi) | 1988-11-23 |
| FI89499B true FI89499B (fi) | 1993-06-30 |
| FI89499C FI89499C (sv) | 1993-10-11 |
Family
ID=21982813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI882305A FI89499C (sv) | 1987-05-22 | 1988-05-17 | Förfarande för framställning av terapeutiskt användbar peptid |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5002931A (sv) |
| EP (1) | EP0292334A3 (sv) |
| JP (1) | JP2758901B2 (sv) |
| KR (1) | KR0143913B1 (sv) |
| AU (1) | AU1647788A (sv) |
| CA (1) | CA1312704C (sv) |
| DK (1) | DK280088A (sv) |
| FI (1) | FI89499C (sv) |
| HU (1) | HUT46932A (sv) |
| IL (1) | IL86166A0 (sv) |
| NO (1) | NO882184L (sv) |
| PT (1) | PT87529B (sv) |
| SU (1) | SU1598881A3 (sv) |
| ZA (1) | ZA882832B (sv) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734399A (en) * | 1985-08-06 | 1988-03-29 | Hoffmann-La Roche Inc. | Growth hormone releasing factor analogs |
| US5098995A (en) * | 1987-05-22 | 1992-03-24 | The Salk Institute For Biological Studies | GRF Analogs VIIA |
| EP0307860B1 (en) * | 1987-09-18 | 1994-06-08 | F. Hoffmann-La Roche Ag | Cyclic GRF-analogs |
| AU4955490A (en) * | 1989-01-27 | 1990-08-24 | Upjohn Company, The | Stabilized, potent grf analogs |
| ZA914983B (en) * | 1990-06-29 | 1992-03-25 | Hoffmann La Roche | His-grf-analogs |
| EP0490249B1 (en) * | 1990-12-10 | 1995-03-15 | F. Hoffmann-La Roche Ag | Process for the enzymatic preparation of GRF(1-44)NH2 |
| JPH05507939A (ja) * | 1991-04-09 | 1993-11-11 | エフ・ホフマン―ラ ロシユ アーゲー | 成長ホルモン放出因子の類似体 |
| US5262519A (en) * | 1991-05-15 | 1993-11-16 | The Salk Institute For Biological Studies | GRF analogs XI |
| CA2158782C (en) * | 1994-09-23 | 2010-01-12 | Pierrette Gaudreau | Marker for growth hormone-releasing factor receptors |
| AU5441096A (en) * | 1995-04-14 | 1996-10-30 | The Administrators Of The Tulane Eductional Fund | Analogs of growth hormone-releasing factor |
| US7963352B2 (en) * | 2003-08-18 | 2011-06-21 | Engineering Recreation (2008) Limited | Powered unicycle |
| US8800697B2 (en) | 2009-09-01 | 2014-08-12 | Ryno Motors, Inc. | Electric-powered self-balancing unicycle with steering linkage between handlebars and wheel forks |
| AU2013305694A1 (en) | 2012-08-22 | 2015-04-09 | Ryno Motors, Inc. | Electric-powered self-balancing unicycle |
| USD739307S1 (en) | 2013-04-30 | 2015-09-22 | Ryno Motors, Inc. | One-wheeled vehicle |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595676A (en) * | 1983-04-26 | 1986-06-17 | The Salk Institute For Biological Studies | Rat hypothalamic GRF |
| US4518586A (en) * | 1983-01-13 | 1985-05-21 | The Salk Institute For Biological Studies | GRF Analogs III |
| AU575843B2 (en) * | 1983-08-10 | 1988-08-11 | The Administrators Of The Tulane Eductional Fund | Growth hormone releasing peptides |
| US4626523A (en) | 1983-09-13 | 1986-12-02 | The Salk Institute For Biological Studies | GRF analogs II |
| US4528190A (en) * | 1983-10-25 | 1985-07-09 | The Salk Institute For Biological Studies | GRF Analogs IV |
| CA1271600A (en) * | 1985-01-07 | 1990-07-10 | David Howard Coy | Growth hormone-releasing peptides and method of treating mammals therewith |
| US4689318A (en) * | 1985-08-29 | 1987-08-25 | The Salk Institute For Biological Studies | GRF analogs |
| US4784987A (en) * | 1987-01-13 | 1988-11-15 | The Salk Institute For Biological Studies | GRF analogs VI |
| US4801456A (en) * | 1987-07-09 | 1989-01-31 | International Minerals & Chemical Corp. | Growth hormone-releasing factor analogs |
-
1987
- 1987-05-22 US US07/053,235 patent/US5002931A/en not_active Expired - Lifetime
-
1988
- 1988-04-21 ZA ZA882832A patent/ZA882832B/xx unknown
- 1988-04-25 IL IL86166A patent/IL86166A0/xx not_active IP Right Cessation
- 1988-05-16 SU SU884355674A patent/SU1598881A3/ru active
- 1988-05-17 FI FI882305A patent/FI89499C/sv not_active IP Right Cessation
- 1988-05-19 PT PT87529A patent/PT87529B/pt not_active IP Right Cessation
- 1988-05-19 NO NO882184A patent/NO882184L/no unknown
- 1988-05-20 CA CA000567405A patent/CA1312704C/en not_active Expired - Fee Related
- 1988-05-20 HU HU882610A patent/HUT46932A/hu unknown
- 1988-05-20 AU AU16477/88A patent/AU1647788A/en not_active Abandoned
- 1988-05-20 DK DK280088A patent/DK280088A/da not_active Application Discontinuation
- 1988-05-21 KR KR1019880006050A patent/KR0143913B1/ko not_active IP Right Cessation
- 1988-05-23 EP EP88304663A patent/EP0292334A3/en not_active Withdrawn
- 1988-05-23 JP JP63125602A patent/JP2758901B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR880013974A (ko) | 1988-12-22 |
| CA1312704C (en) | 1993-01-12 |
| EP0292334A3 (en) | 1990-06-27 |
| FI882305A (fi) | 1988-11-23 |
| NO882184D0 (no) | 1988-05-19 |
| US5002931A (en) | 1991-03-26 |
| NO882184L (no) | 1988-11-23 |
| DK280088A (da) | 1988-11-23 |
| IL86166A0 (en) | 1988-11-15 |
| SU1598881A3 (ru) | 1990-10-07 |
| KR0143913B1 (ko) | 1998-07-01 |
| PT87529B (pt) | 1992-09-30 |
| ZA882832B (en) | 1988-11-11 |
| DK280088D0 (da) | 1988-05-20 |
| AU1647788A (en) | 1988-11-24 |
| EP0292334A2 (en) | 1988-11-23 |
| HUT46932A (en) | 1988-12-28 |
| JPS649999A (en) | 1989-01-13 |
| PT87529A (pt) | 1989-05-31 |
| JP2758901B2 (ja) | 1998-05-28 |
| FI89499C (sv) | 1993-10-11 |
| FI882305A0 (fi) | 1988-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: THE SALK INSTITUTE FOR BIOLOGICAL |