IE33835B1 - New peptides and process for their manufacture - Google Patents
New peptides and process for their manufactureInfo
- Publication number
- IE33835B1 IE33835B1 IE1403/69A IE140369A IE33835B1 IE 33835 B1 IE33835 B1 IE 33835B1 IE 1403/69 A IE1403/69 A IE 1403/69A IE 140369 A IE140369 A IE 140369A IE 33835 B1 IE33835 B1 IE 33835B1
- Authority
- IE
- Ireland
- Prior art keywords
- thr
- gly
- ala
- phe
- boc
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 6
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 108010079364 N-glycylalanine Proteins 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- VPZXBVLAVMBEQI-UHFFFAOYSA-N glycyl-DL-alpha-alanine Natural products OC(=O)C(C)NC(=O)CN VPZXBVLAVMBEQI-UHFFFAOYSA-N 0.000 abstract 3
- 108010037850 glycylvaline Proteins 0.000 abstract 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 2
- FHOAKXBXYSJBGX-YFKPBYRVSA-N (2s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O FHOAKXBXYSJBGX-YFKPBYRVSA-N 0.000 abstract 1
- 229940121799 Hypocalcaemic agent Drugs 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- XZONQWUEBAFQPO-HJGDQZAQSA-N Pro-Gln-Thr Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O XZONQWUEBAFQPO-HJGDQZAQSA-N 0.000 abstract 1
- PXQUBKWZENPDGE-CIQUZCHMSA-N Thr-Ala-Ile Chemical compound CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)N PXQUBKWZENPDGE-CIQUZCHMSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001371 alpha-amino acids Chemical class 0.000 abstract 1
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 125000000539 amino acid group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 210000004899 c-terminal region Anatomy 0.000 abstract 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical class N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- 108010092114 histidylphenylalanine Proteins 0.000 abstract 1
- BPISBTXISIPAEQ-XPUUQOCRSA-N methyl 2-[[(2s,3s)-2-amino-3-methylpentanoyl]amino]acetate Chemical compound CC[C@H](C)[C@H](N)C(=O)NCC(=O)OC BPISBTXISIPAEQ-XPUUQOCRSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GEMSXPOJLIUVKT-IUCAKERBSA-N tert-butyl (2s)-1-[(2s)-2-aminopropanoyl]pyrrolidine-2-carboxylate Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C GEMSXPOJLIUVKT-IUCAKERBSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 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
- C07K14/585—Calcitonins
-
- 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
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Endocrinology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
1287125 Calcitonin derivatives CIBAGEIGY AG 13 Oct 1969 [15 Oct 1968 20 Nov 1968] 50087/69 Heading C2C Peptides (I) in which at least one and at the most 16 of the amino acids in positions 2, 8, 10, 11, 12, 13, 14, 16, 18, 21, 23, 24, 25, 26, 27, 29, 30 and 31 are replaced by other natural α-amino acids or their homologues their dimers and derivatives (especially their N-acylated and desamino<SP>1</SP>- peptides) of the mono- or di-meric peptides as well as their acid addition salts and complexes are prepared (1) by removing the blocking groups from a compound (I) in which any free amino or carboxylic acid group is blocked or (2) by oxidizing the linear peptide corresponding to (I) and wherein the mercapto groups may be tritylated or (3) by condensing a compound (III) or (IV) or where Y is Gly or Ser, A is 1-21 of the amino acid residues following upon Cys<SP>7</SP> and R is H or an acylated amino group, with the remaining amidated C-terminal sequence of the peptide in which any side chain amino group is protected. The following starting materials are prepared: Z- and H-Ala-Pro-OtBu, Z- and H-Qly-Ala- ProOtBu, Z - Val - Gly - Ala - ProOtBu and -OH and -NH 2 , H-Val- Gly - Ala - Pro - NH 2 , Z. and H - Ile - Gly OMe, Z- and H -Ala-Ile- Gly OMe, BOC - Thr - Ala - Ile-Gly-OMe and -NHNH 2 , BOC and H - Thr - Ala - He - Gly- Val - Gly - Ala - ProNH 2 , Z- and H - Pro - Gln- NHNHBOC, Z- and H - Phe - Pro - Gln- NHNHBOC, Z- and H - Thr - Phe - Pro - Gln- NHNHBOC, Z - His - Thr - Phe - Pro - Gln- NHNHBOC and -NHNH 2 , Z - His - Thr- Phe - Pro - Gln - Thr - Ala - lie - Gly - Val - Gly- Ala - ProNH 2 Z - Lys (BOC) - Phe - OBzl, H- lys(BOC)PheOH, Z- and H - Asn - Lys(BOC}- Phe - OH, Z - Asp(OtBu) - Phe - OMe and -NHNH 2 , Z- and H - Asp(OtBu) - Phe - Asn- Lys(BOC} - Phe - OH, BOC- and H - Tyr - Thr- ONB, Z - Thr - Tyr - Thr - ONB and -NHNH 2 , Z - Thr - Tyr - Thr - Gln - NHNHBOC and - NHNH Z , Z- and H - His - Thr - Phe - Pro- Gln . Thr - Ala - Ile - Gly - Val - Gly - Ala - Pro- NH 2 , Z- and. H - Thr - Tyr - Thr - Gln -Asp- (OtBu) - Phe - Asn - Lys(BOC) - Phe - His - Thr- Phe . Pro - Gln - Thr - Ala - lie - Gly - Val - Gly- Ala - Pro - NH 2 , BOC - Ser - Thr - OBzl, HSer - Thr - OBzl, BOC- and H - Leu - Ser - Thr OBzl, BOC- and H - Asn - Leu - Ser - Thr- OBzl, BOC - Gly - Asn - Leu - Ser - Thr - OBzl and OH BOC and H-Gly-Asn-Leu-Ser-Thr- Thr(tBu) - Phe - Pro - Gln - Thr(tBu) - Ala - Ile- Gly - Val - Gly - Ala - Pro - NH 2 . Pharmaceutical compositions useful as hypocalcaemic agents comprise compounds (I) and a carrier and are in forms suitable for oral and parenteral administration.
[GB1287125A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1540168A CH550774A (en) | 1968-10-15 | 1968-10-15 | Dotriacontapeptide calcitonin analogues - with hypocalcaemic activity |
| CH1728668 | 1968-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33835L IE33835L (en) | 1970-04-15 |
| IE33835B1 true IE33835B1 (en) | 1974-11-13 |
Family
ID=25716344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1403/69A IE33835B1 (en) | 1968-10-15 | 1969-10-10 | New peptides and process for their manufacture |
Country Status (11)
| Country | Link |
|---|---|
| AT (2) | AT313491B (en) |
| BE (1) | BE740256A (en) |
| CS (1) | CS155219B2 (en) |
| DE (1) | DE1950711A1 (en) |
| DK (1) | DK129338B (en) |
| FR (1) | FR2020730B1 (en) |
| GB (1) | GB1287125A (en) |
| HU (1) | HU166686B (en) |
| IE (1) | IE33835B1 (en) |
| NL (1) | NL6915540A (en) |
| SE (2) | SE374913B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50117791A (en) * | 1974-03-07 | 1975-09-16 | ||
| US3929758A (en) * | 1974-09-12 | 1975-12-30 | Armour Pharma | Cyclization of cysteine-containing peptides |
| DE2602443A1 (en) | 1975-04-04 | 1976-10-21 | Univ California | BIOLOGICALLY ACTIVE POLYPEPTIDES |
| US4401593A (en) * | 1982-02-12 | 1983-08-30 | Armour Pharmaceutical Company | Glycine - 8 calcitonin |
| DE3822394A1 (en) * | 1988-07-01 | 1990-01-04 | Walter Frenkel | Massaging device with removable handle |
| CS89491A3 (en) * | 1990-04-09 | 1992-01-15 | Chugai Pharmaceutical Co Ltd | Hybrid calcitonin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE684858A (en) * | 1965-07-30 | 1967-01-30 | ||
| GB1230631A (en) * | 1967-05-12 | 1971-05-05 | ||
| CA919590A (en) * | 1967-05-24 | 1973-01-23 | Neher Robert | Process for the manufacture of thyrocalcitonin |
-
1969
- 1969-10-08 DE DE19691950711 patent/DE1950711A1/en active Pending
- 1969-10-10 IE IE1403/69A patent/IE33835B1/en unknown
- 1969-10-13 SE SE7216700A patent/SE374913B/xx unknown
- 1969-10-13 SE SE14000/69A patent/SE366543B/xx unknown
- 1969-10-13 GB GB50087/69A patent/GB1287125A/en not_active Expired
- 1969-10-14 BE BE740256D patent/BE740256A/xx unknown
- 1969-10-14 AT AT172971A patent/AT313491B/en not_active IP Right Cessation
- 1969-10-14 NL NL6915540A patent/NL6915540A/xx unknown
- 1969-10-14 AT AT966769A patent/AT300210B/en not_active IP Right Cessation
- 1969-10-14 FR FR6935098A patent/FR2020730B1/fr not_active Expired
- 1969-10-14 DK DK545669AA patent/DK129338B/en unknown
- 1969-10-14 HU HUCI929A patent/HU166686B/hu unknown
- 1969-10-15 CS CS686369A patent/CS155219B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE374913B (en) | 1975-03-24 |
| NL6915540A (en) | 1970-04-17 |
| SE366543B (en) | 1974-04-29 |
| GB1287125A (en) | 1972-08-31 |
| FR2020730A1 (en) | 1970-07-17 |
| DK129338B (en) | 1974-09-30 |
| DE1950711A1 (en) | 1970-04-30 |
| HU166686B (en) | 1975-05-28 |
| AT313491B (en) | 1974-02-25 |
| FR2020730B1 (en) | 1974-04-12 |
| AT300210B (en) | 1972-07-25 |
| DK129338C (en) | 1975-02-17 |
| BE740256A (en) | 1970-04-14 |
| CS155219B2 (en) | 1974-05-30 |
| IE33835L (en) | 1970-04-15 |
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