SE444946B - Peptider, som inhiberar frigorandet av steroider - Google Patents
Peptider, som inhiberar frigorandet av steroiderInfo
- Publication number
- SE444946B SE444946B SE7812255A SE7812255A SE444946B SE 444946 B SE444946 B SE 444946B SE 7812255 A SE7812255 A SE 7812255A SE 7812255 A SE7812255 A SE 7812255A SE 444946 B SE444946 B SE 444946B
- Authority
- SE
- Sweden
- Prior art keywords
- trp
- pro
- leu
- peptides
- peptide
- Prior art date
Links
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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
-
- 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
- C07K7/16—Oxytocins; Vasopressins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85583777A | 1977-11-30 | 1977-11-30 | |
| US05/950,301 US4215038A (en) | 1978-10-16 | 1978-10-16 | Peptides which inhibit gonadal function |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7812255L SE7812255L (sv) | 1979-05-31 |
| SE444946B true SE444946B (sv) | 1986-05-20 |
Family
ID=27127312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7812255A SE444946B (sv) | 1977-11-30 | 1978-11-28 | Peptider, som inhiberar frigorandet av steroider |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU520419B2 (de) |
| CA (1) | CA1116594A (de) |
| CH (1) | CH639942A5 (de) |
| DE (1) | DE2851630A1 (de) |
| FR (1) | FR2410642A1 (de) |
| GB (1) | GB2009182B (de) |
| NL (1) | NL7811723A (de) |
| NZ (1) | NZ188987A (de) |
| SE (1) | SE444946B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292313A (en) * | 1980-04-15 | 1981-09-29 | The Salk Institute For Biological Studies | LRF Antagonists |
| NZ196558A (en) * | 1980-04-15 | 1984-10-19 | Salk Inst For Biological Studi | Lrf antagonists and pharmaceutical compositions |
| US4409208A (en) * | 1980-04-15 | 1983-10-11 | The Salk Institute For Biological Studies | GnRH antagonists |
| ATE8988T1 (de) * | 1980-06-02 | 1984-09-15 | Andrew Victor Schally | Lh-rh antagonisten. |
| IL70888A0 (en) * | 1983-03-10 | 1984-05-31 | Salk Inst For Biological Studi | Gn rh antagonist peptides and pharmaceutical compositions containing them |
| US4530920A (en) * | 1983-11-07 | 1985-07-23 | Syntex (U.S.A.) Inc. | Nonapeptide and decapeptide analogs of LHRH, useful as LHRH agonist |
| US4547370A (en) * | 1983-11-29 | 1985-10-15 | The Salk Institute For Biological Studies | GnRH Antagonists |
| IL74827A (en) * | 1984-05-21 | 1989-06-30 | Salk Inst For Biological Studi | Peptides active as gnrh antagonists and pharmaceutical compositions containing them |
| US4632979A (en) * | 1984-06-18 | 1986-12-30 | Tulane Educational Fund | Therapeutic LHRH analogs |
| ZA862570B (en) * | 1985-04-09 | 1986-12-30 | Univ Tulane | Therapeutic decapeptides |
| US4866160A (en) * | 1985-04-09 | 1989-09-12 | The Administrators Of The Tulane Educational Fund | Therapeutic decapeptides |
| EP0225746A3 (de) * | 1985-11-14 | 1989-12-20 | The Administrators of The Tulane Educational Fund | Therapeutische Dekapeptide |
| DE3634435A1 (de) * | 1986-10-09 | 1988-04-14 | Hoechst Ag | Analoga von gonadoliberin mit verbesserter loeslichkeit, verfahren zu deren herstellung, diese enthaltende mittel und ihre verwendung |
| DE68928278T2 (de) * | 1988-02-10 | 1998-03-12 | Tap Pharmaceuticals Inc | Lhrh-analog |
| US5110904A (en) * | 1989-08-07 | 1992-05-05 | Abbott Laboratories | Lhrh analogs |
| US5084443A (en) * | 1989-12-04 | 1992-01-28 | Biomeasure, Inc. | Promoting expression of acetylcholine receptors with lhrh antagonist |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928307A (en) * | 1974-11-04 | 1975-12-23 | American Home Prod | P-Glu-D-Phe-Trp-Ser-Tyr-D-Phee-Leu-Arg-Pro-Gly-NH2 and intermediates |
| US3933782A (en) * | 1974-11-14 | 1976-01-20 | American Home Products Corporation | (N-Acetyl)-Pro-D-Phe-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-NHEt and intermediates |
| US4089946A (en) * | 1976-06-07 | 1978-05-16 | American Home Products Corporation | Claudogenic-interceptive nonapeptides |
-
1978
- 1978-11-22 NZ NZ188987A patent/NZ188987A/xx unknown
- 1978-11-27 AU AU41948/78A patent/AU520419B2/en not_active Expired
- 1978-11-28 SE SE7812255A patent/SE444946B/sv not_active IP Right Cessation
- 1978-11-28 CA CA000317018A patent/CA1116594A/en not_active Expired
- 1978-11-29 NL NL7811723A patent/NL7811723A/xx not_active Application Discontinuation
- 1978-11-29 DE DE19782851630 patent/DE2851630A1/de not_active Withdrawn
- 1978-11-29 FR FR7833756A patent/FR2410642A1/fr active Granted
- 1978-11-30 CH CH1225878A patent/CH639942A5/de not_active IP Right Cessation
- 1978-11-30 GB GB7846680A patent/GB2009182B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2009182A (en) | 1979-06-13 |
| NL7811723A (nl) | 1979-06-01 |
| CA1116594A (en) | 1982-01-19 |
| GB2009182B (en) | 1982-02-24 |
| DE2851630A1 (de) | 1979-05-31 |
| SE7812255L (sv) | 1979-05-31 |
| AU4194878A (en) | 1979-06-07 |
| AU520419B2 (en) | 1982-01-28 |
| FR2410642A1 (fr) | 1979-06-29 |
| CH639942A5 (de) | 1983-12-15 |
| FR2410642B1 (de) | 1983-10-21 |
| NZ188987A (en) | 1982-02-23 |
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