IL48514A - Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone - Google Patents
Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormoneInfo
- Publication number
- IL48514A IL48514A IL48514A IL4851473A IL48514A IL 48514 A IL48514 A IL 48514A IL 48514 A IL48514 A IL 48514A IL 4851473 A IL4851473 A IL 4851473A IL 48514 A IL48514 A IL 48514A
- Authority
- IL
- Israel
- Prior art keywords
- ester
- isolating
- treating
- mixture
- solution
- Prior art date
Links
- 108700012941 GNRH1 Proteins 0.000 title 2
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 title 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- -1 aralkyl ester Chemical class 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000012442 inert solvent Substances 0.000 claims 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 5
- 239000011707 mineral Substances 0.000 claims 5
- 229910000510 noble metal Inorganic materials 0.000 claims 3
- 150000007530 organic bases Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
-
- 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
-
- 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)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (1)
1. i v i A process preparing the hexapeptide y I hydrazide i uoroacetate which comprises treating a solution of y i st dy hydrazide an inert anh drous solvent with a strong mineral acid and an organic nitrite at a temperature of from about to about making the alkaline by addition of a strong organic adding a solution of ester in an inert anhydrous agitating the mixture at a temperature within the range about to about to obtain treating said trifluoroacetic and isolating the hexapeptide named A process as claimed in the anhydrous inert solvent is dinethylformamide or a mixture of and A process in Claim in which the strong mineral acid is hydrogen A process as claimed in 1 in which strong organic base is A process as claimed in Claim I in which the organic nitrite is nitrite or 1 i v i s i ona process as claimed in Claim 1 in which the hydrazide is prepared by treating a solution of hydrazide in an inert anhydrous solvent with a strong Mineral acid and an organic nitrite at a temperature of from about to about making the mixture alkaline by addition of a strong organic adding a solution of a lower alkyl or aralkyl ester of in an inert anhydrous agitating the mixture at a temperature within the range from about about and isolating the corresponding lower alkyl or aralkyl treating said compound with hydrazine and isolating hydrazide0 process as claimed in Claim 6 in which the anhydrous inert solvent is dimethylformamide or a mixture of dimethylformamide and Λ process as claimed in Claim 6 in which the strong mineral acid is hydxogen A process as claimed in Claim in which the strong organic base is triethylaminee process as claimed in Claim 6 in which the nitrite is nitrite or isoainyl A process as claimed in Claim 6 in which the ester of ryptophan is the benzyl A process the hexapeptide lycine hydrnzide trifluoroacetate which comprises treating benzyl ester with hydrogen and a noble and isolating treating said compound in solution in an anhydrous inert solvent with lycine ester and at a within the range of about to room and isolating lycine treating said compound with trifluoroacetic and isolating the hexapeptide named A process as claimed in Claim 12 in which the noble metal catalyst is A process as claimed in Claim 12 in which the inert solvent is process as claimed in Claim 1 or 12 in which the lycine ester by treating a lower alkyl ester of ester an aqueous alkali metal hydroxide followed by acidification of the isolating treating said compound in solution in an or cyclic ether first with ethyl and then with and isolating ester treating said with hydrogen and a noble and isolating adding said compound in solution in a halogenated hydrocarbon to an activated ester of keeping the mixture at about for several and isolating ester treating said compound with hydrogen and a noble metal and isolating A process as claimed in Claim 15 in which the lower alkyl ester of ester is the methyl A process claimed in in which the noble metal catalyst is A process as in Claim 15 in which halogenated hydrocarbon is A process as claimed in Claim 15 i which the A process as claimed in Claim 12 in which the an benzyl ester is prepared by treating a solution of hydrazide in an inert anhydrous solvent with a strong acid and an organic nitrite at a temperature of from about to about making the mixture alkaline by addition of a strong organic adding a solution of benzyl ester in an inert anhydrous agitating the mixture at a temperature within the range from about to about and isolating the corresponding benzyl A process as claimed in Claim 20 in which the anhydrous inert solvent is dimethylformanide or a mixture of dimethylformamide and process as claimed in Claim 20 in which the strong mineral acid is hydrogen A process as claimed in Claim 20 in which the strong organic base is triethylaminee A process as claimed in Claim 20 in which the organic nitrite is nitrite or isoamyl I I lyci ne hydrazide insufficientOCRQuality
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00226508A US3835108A (en) | 1972-02-15 | 1972-02-15 | Process for preparing the releasing hormone of luteinizing hormone(lh)and of follicle stimulating hormone(fsh),salts and compositions thereof,and intermediates therefor |
| US24346572A | 1972-04-12 | 1972-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL48514A true IL48514A (en) | 1976-08-31 |
Family
ID=26920599
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL48514A IL48514A (en) | 1972-02-15 | 1973-01-17 | Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone |
| IL41313A IL41313A (en) | 1972-02-15 | 1973-01-17 | Preparation of the lh-and fsh-releasing hormone and compositions containing it |
| IL48514A IL48514A0 (en) | 1972-02-15 | 1975-11-21 | Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41313A IL41313A (en) | 1972-02-15 | 1973-01-17 | Preparation of the lh-and fsh-releasing hormone and compositions containing it |
| IL48514A IL48514A0 (en) | 1972-02-15 | 1975-11-21 | Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5729462B2 (en) |
| CA (1) | CA1025441A (en) |
| CH (1) | CH589608A5 (en) |
| DE (1) | DE2307010C2 (en) |
| FR (1) | FR2181730B1 (en) |
| GB (3) | GB1425513A (en) |
| IL (3) | IL48514A (en) |
| NZ (1) | NZ169577A (en) |
| SE (1) | SE403772B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL68992A (en) * | 1982-06-29 | 1991-06-10 | Astra Laekemedel Ab | Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS528831B2 (en) * | 1971-10-04 | 1977-03-11 |
-
1973
- 1973-01-17 IL IL48514A patent/IL48514A/en unknown
- 1973-01-17 NZ NZ169577A patent/NZ169577A/en unknown
- 1973-01-17 IL IL41313A patent/IL41313A/en unknown
- 1973-02-13 DE DE2307010A patent/DE2307010C2/en not_active Expired
- 1973-02-14 GB GB3217475A patent/GB1425513A/en not_active Expired
- 1973-02-14 FR FR7305151A patent/FR2181730B1/fr not_active Expired
- 1973-02-14 GB GB718073A patent/GB1425511A/en not_active Expired
- 1973-02-14 GB GB3217675A patent/GB1425512A/en not_active Expired
- 1973-02-14 CH CH210773A patent/CH589608A5/xx not_active IP Right Cessation
- 1973-02-14 SE SE7302099A patent/SE403772B/en unknown
- 1973-02-15 CA CA163,972A patent/CA1025441A/en not_active Expired
- 1973-02-15 JP JP1884473A patent/JPS5729462B2/ja not_active Expired
-
1975
- 1975-11-21 IL IL48514A patent/IL48514A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH589608A5 (en) | 1977-07-15 |
| FR2181730A1 (en) | 1973-12-07 |
| IL41313A0 (en) | 1973-03-30 |
| GB1425511A (en) | 1976-02-18 |
| JPS5729462B2 (en) | 1982-06-23 |
| SE403772B (en) | 1978-09-04 |
| FR2181730B1 (en) | 1977-07-15 |
| CA1025441A (en) | 1978-01-31 |
| NZ169577A (en) | 1984-09-28 |
| DE2307010A1 (en) | 1973-08-23 |
| JPS4886868A (en) | 1973-11-15 |
| GB1425512A (en) | 1976-02-18 |
| DE2307010C2 (en) | 1986-08-21 |
| IL41313A (en) | 1976-08-31 |
| IL48514A0 (en) | 1976-01-30 |
| GB1425513A (en) | 1976-02-18 |
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