IL41313A - Preparation of the lh-and fsh-releasing hormone and compositions containing it - Google Patents
Preparation of the lh-and fsh-releasing hormone and compositions containing itInfo
- Publication number
- IL41313A IL41313A IL41313A IL4131373A IL41313A IL 41313 A IL41313 A IL 41313A IL 41313 A IL41313 A IL 41313A IL 4131373 A IL4131373 A IL 4131373A IL 41313 A IL41313 A IL 41313A
- Authority
- IL
- Israel
- Prior art keywords
- ester
- carboxy
- treating
- isolating
- prolyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 18
- 108700012941 GNRH1 Proteins 0.000 title claims 4
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 title claims 4
- 238000000034 method Methods 0.000 claims 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 36
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 32
- 239000002253 acid Substances 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 18
- 239000004471 Glycine Substances 0.000 claims 16
- 150000007530 organic bases Chemical class 0.000 claims 16
- 125000005907 alkyl ester group Chemical group 0.000 claims 13
- 239000003054 catalyst Substances 0.000 claims 13
- 229910000510 noble metal Inorganic materials 0.000 claims 13
- 150000002148 esters Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 239000012442 inert solvent Substances 0.000 claims 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 8
- 239000011707 mineral Substances 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- 150000008282 halocarbons Chemical class 0.000 claims 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 5
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 5
- 229910052763 palladium Inorganic materials 0.000 claims 5
- OHCMNYPOVOHMJR-BZSNNMDCSA-N (2s)-2-[[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)NC(=O)[C@H]1NC(=O)CC1)C1=CNC=N1 OHCMNYPOVOHMJR-BZSNNMDCSA-N 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 4
- -1 aralkyl ester Chemical class 0.000 claims 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 4
- 229960002429 proline Drugs 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 claims 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims 3
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical group [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 claims 2
- WVISONSNWGLKSK-YFKPBYRVSA-N (2s)-2-(carboxyamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC(O)=O WVISONSNWGLKSK-YFKPBYRVSA-N 0.000 claims 2
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- 229930182821 L-proline Natural products 0.000 claims 2
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 150000004292 cyclic ethers Chemical class 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- 238000004810 partition chromatography Methods 0.000 claims 2
- 229960004799 tryptophan Drugs 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- VNFJIBZRKDALBZ-UHFFFAOYSA-N 2-amino-n-tert-butylacetamide Chemical compound CC(C)(C)NC(=O)CN VNFJIBZRKDALBZ-UHFFFAOYSA-N 0.000 claims 1
- JXYACYYPACQCDM-UHFFFAOYSA-N Benzyl glycinate Chemical compound NCC(=O)OCC1=CC=CC=C1 JXYACYYPACQCDM-UHFFFAOYSA-N 0.000 claims 1
- 229920002307 Dextran Polymers 0.000 claims 1
- IBMVEYRWAWIOTN-UHFFFAOYSA-N L-Leucyl-L-Arginyl-L-Proline Natural products CC(C)CC(N)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(O)=O IBMVEYRWAWIOTN-UHFFFAOYSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims 1
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- 208000035752 Live birth Diseases 0.000 claims 1
- 101100091501 Mus musculus Ros1 gene Proteins 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000003957 anion exchange resin Substances 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- TYQYRKDGHAPZRF-INIZCTEOSA-N benzyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound O=C([C@H](CC=1C2=CC=CC=C2NC=1)N)OCC1=CC=CC=C1 TYQYRKDGHAPZRF-INIZCTEOSA-N 0.000 claims 1
- HBBRVEMMVUOSTL-UHFFFAOYSA-N butyl n-aminocarbamate Chemical compound CCCCOC(=O)NN HBBRVEMMVUOSTL-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 230000012173 estrus Effects 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000002267 hypothalamic effect Effects 0.000 claims 1
- 238000002513 implantation Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 229960003136 leucine Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000007257 malfunction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HQEIPVHJHZTMDP-JEDNCBNOSA-N methyl (2s)-pyrrolidine-2-carboxylate;hydrochloride Chemical group Cl.COC(=O)[C@@H]1CCCN1 HQEIPVHJHZTMDP-JEDNCBNOSA-N 0.000 claims 1
- 230000016087 ovulation Effects 0.000 claims 1
- 230000001817 pituitary effect Effects 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| IL41313A0 IL41313A0 (en) | 1973-03-30 |
| IL41313A true IL41313A (en) | 1976-08-31 |
Family
ID=26920599
Family Applications (3)
| 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 IL48514A (en) | 1972-02-15 | 1973-01-17 | Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone |
| 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 |
|---|---|---|---|
| IL48514A IL48514A (en) | 1972-02-15 | 1973-01-17 | Hexapeptide intermediate for the preparation of the lh-and fsh-releasing hormone |
| 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 (enExample) |
| CA (1) | CA1025441A (enExample) |
| CH (1) | CH589608A5 (enExample) |
| DE (1) | DE2307010C2 (enExample) |
| FR (1) | FR2181730B1 (enExample) |
| GB (3) | GB1425513A (enExample) |
| IL (3) | IL41313A (enExample) |
| NZ (1) | NZ169577A (enExample) |
| SE (1) | SE403772B (enExample) |
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 (enExample) * | 1971-10-04 | 1977-03-11 |
-
1973
- 1973-01-17 IL IL41313A patent/IL41313A/en unknown
- 1973-01-17 NZ NZ169577A patent/NZ169577A/xx unknown
- 1973-01-17 IL IL48514A patent/IL48514A/en unknown
- 1973-02-13 DE DE2307010A patent/DE2307010C2/de not_active Expired
- 1973-02-14 SE SE7302099A patent/SE403772B/xx unknown
- 1973-02-14 FR FR7305151A patent/FR2181730B1/fr not_active Expired
- 1973-02-14 GB GB3217475A patent/GB1425513A/en not_active Expired
- 1973-02-14 CH CH210773A patent/CH589608A5/xx not_active IP Right Cessation
- 1973-02-14 GB GB718073A patent/GB1425511A/en not_active Expired
- 1973-02-14 GB GB3217675A patent/GB1425512A/en not_active Expired
- 1973-02-15 JP JP1884473A patent/JPS5729462B2/ja not_active Expired
- 1973-02-15 CA CA163,972A patent/CA1025441A/en not_active Expired
-
1975
- 1975-11-21 IL IL48514A patent/IL48514A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5729462B2 (enExample) | 1982-06-23 |
| CA1025441A (en) | 1978-01-31 |
| DE2307010A1 (de) | 1973-08-23 |
| IL48514A (en) | 1976-08-31 |
| JPS4886868A (enExample) | 1973-11-15 |
| GB1425513A (en) | 1976-02-18 |
| IL41313A0 (en) | 1973-03-30 |
| NZ169577A (en) | 1984-09-28 |
| FR2181730B1 (enExample) | 1977-07-15 |
| DE2307010C2 (de) | 1986-08-21 |
| GB1425511A (en) | 1976-02-18 |
| GB1425512A (en) | 1976-02-18 |
| CH589608A5 (enExample) | 1977-07-15 |
| FR2181730A1 (enExample) | 1973-12-07 |
| SE403772B (sv) | 1978-09-04 |
| IL48514A0 (en) | 1976-01-30 |
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