GB1243035A - New hypocalcaemic peptides and processes for their manufacture - Google Patents
New hypocalcaemic peptides and processes for their manufactureInfo
- Publication number
- GB1243035A GB1243035A GB52391/68A GB5239168A GB1243035A GB 1243035 A GB1243035 A GB 1243035A GB 52391/68 A GB52391/68 A GB 52391/68A GB 5239168 A GB5239168 A GB 5239168A GB 1243035 A GB1243035 A GB 1243035A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tbu
- asn
- ser
- leu
- phe
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract 4
- 102000004196 processed proteins & peptides Human genes 0.000 title abstract 3
- 230000001184 hypocalcaemic effect Effects 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 108010070783 alanyltyrosine Proteins 0.000 abstract 9
- 108010051242 phenylalanylserine Proteins 0.000 abstract 9
- 108010036320 valylleucine Proteins 0.000 abstract 7
- 108010079413 glycyl-prolyl-glutamic acid Proteins 0.000 abstract 6
- 108010092114 histidylphenylalanine Proteins 0.000 abstract 6
- JBCLFWXMTIKCCB-UHFFFAOYSA-N H-Gly-Phe-OH Natural products NCC(=O)NC(C(O)=O)CC1=CC=CC=C1 JBCLFWXMTIKCCB-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 BOC- Chemical class 0.000 abstract 3
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- AOHKLEBWKMKITA-IHRRRGAJSA-N Arg-Phe-Ser Chemical compound C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CO)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)N AOHKLEBWKMKITA-IHRRRGAJSA-N 0.000 abstract 2
- NVGWESORMHFISY-SRVKXCTJSA-N Asn-Asn-Phe Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O NVGWESORMHFISY-SRVKXCTJSA-N 0.000 abstract 2
- YXQDRIRSAHTJKM-IMJSIDKUSA-N Cys-Ser Chemical compound SC[C@H](N)C(=O)N[C@@H](CO)C(O)=O YXQDRIRSAHTJKM-IMJSIDKUSA-N 0.000 abstract 2
- KZZYVYWSXMFYEC-DCAQKATOSA-N Cys-Val-Leu Chemical compound [H]N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O KZZYVYWSXMFYEC-DCAQKATOSA-N 0.000 abstract 2
- 229910004373 HOAc Inorganic materials 0.000 abstract 2
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 abstract 2
- 108010070643 prolylglutamic acid Proteins 0.000 abstract 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- BVBKBQRPOJFCQM-DCAQKATOSA-N Arg-Asn-Leu Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(O)=O BVBKBQRPOJFCQM-DCAQKATOSA-N 0.000 abstract 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 1
- ZMUQQMGITUJQTI-CIUDSAMLSA-N Asn-Leu-Asn Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O ZMUQQMGITUJQTI-CIUDSAMLSA-N 0.000 abstract 1
- KVCJEMHFLGVINV-ZLUOBGJFSA-N Cys-Ser-Asn Chemical compound SC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@H](C(O)=O)CC(N)=O KVCJEMHFLGVINV-ZLUOBGJFSA-N 0.000 abstract 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N Cysteine Chemical compound SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract 1
- 239000001828 Gelatine Substances 0.000 abstract 1
- 229940121799 Hypocalcaemic agent Drugs 0.000 abstract 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 abstract 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 abstract 1
- SUPVSFFZWVOEOI-UHFFFAOYSA-N Leu-Ala-Tyr Natural products CC(C)CC(N)C(=O)NC(C)C(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 SUPVSFFZWVOEOI-UHFFFAOYSA-N 0.000 abstract 1
- XGDCYUQSFDQISZ-BQBZGAKWSA-N Leu-Ser Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CO)C(O)=O XGDCYUQSFDQISZ-BQBZGAKWSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
- LQMHZERGCQJKAH-STQMWFEESA-N Met-Gly-Phe Chemical compound CSCC[C@H](N)C(=O)NCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 LQMHZERGCQJKAH-STQMWFEESA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- KZNQNBZMBZJQJO-UHFFFAOYSA-N N-glycyl-L-proline Natural products NCC(=O)N1CCCC1C(O)=O KZNQNBZMBZJQJO-UHFFFAOYSA-N 0.000 abstract 1
- FJJWGZOCZQHVEO-RQJHMYQMSA-N O-t-butyl-l-threonine methyl ester Chemical compound COC(=O)[C@@H](N)[C@@H](C)OC(C)(C)C FJJWGZOCZQHVEO-RQJHMYQMSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 108010020346 Polyglutamic Acid Proteins 0.000 abstract 1
- BTWMICVCQLKKNR-DCAQKATOSA-N Val-Leu-Ser Chemical compound CC(C)[C@H]([NH3+])C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C([O-])=O BTWMICVCQLKKNR-DCAQKATOSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 1
- 235000011180 diphosphates Nutrition 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 abstract 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 abstract 1
- 108010077435 glycyl-phenylalanyl-glycine Proteins 0.000 abstract 1
- 108010077515 glycylproline Proteins 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 abstract 1
- PKLDYUWADSNDGB-IRXDYDNUSA-N methyl (2S)-4-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoate Chemical compound COC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1 PKLDYUWADSNDGB-IRXDYDNUSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229920002643 polyglutamic acid Polymers 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000004474 valine Substances 0.000 abstract 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 abstract 1
- 229910000165 zinc phosphate Inorganic materials 0.000 abstract 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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/067—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for sulfur-containing functions
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or 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
- C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Endocrinology (AREA)
- Analytical Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
1,243,035. Thyrocalcitons. CIBA GEIGY A.G. 5 Nov., 1968 [9 Nov., 1967; 6 Feb., 1968; 29 April, 1968; 4 May, 1968; 10 May, 1968; 21 May; 1968], No. 52391/68. Heading C2C. Compounds of the formula HCys - Ser - Asn - Leu - Ser - Thr - Cys - Val- Leu - Ala - Tyr - Try - Arg - Asn - Leu - Asn- Asn - Phe - His - .Arg - Phe - Ser - Gly - Met- Gly - Phe - Gly - Pro - Glu - Thr - Pro - OH and the corresponding compound where one or more asparaginine residues are replaced by aspartic acid residues and/or the glutamic acid residue by the glutamine residue and/or methionine residue by the valine, norvaline, leucine, isoleucine or norsleucine residue, and their salts derivatives (including esters, amides, N-acyl derivatives desamino<SP>1</SP>-peptides and Met<SP>25</SP>-sulphoxides) and complexes, are prepared in a per se conventional manner for forming polypeptides from amino acids or smaller peptide units. N-acylated peptides include N-acetyl, N- phenylthiocarbamoyl- and N-pyroglutamylpeptides and complexes are those formed with zinc phosphate, pyrophosphate, or hydroxide, gelatine, polyphloretine phosphate or polyglutamic acid. Pharmaceutical compositions containing the compounds of the invention in forms suitable for enteral and parenteral administration. The compounds are hypocalcaemic agents and compositions may contain other drugs. The following starting materials and intermediates are prepared: H-Thr(tBu)-OMe, DPC- - Ser (tBu) - Thr[tBu) - OMe, Z - Val - Leu - OMe, DPC - Ser(tBu) - Thr(tBu)NHNH 2 H - Val- Leu - OMe, HCl, TR1 - and H - Cys(TR1)- Val - Leu - OMe, DPC - Ser(tBu) - Thr(tBu)- Cys(TR1)- Val - Leu - OMe and -OH - H - Ser (tBu) - Thr(tBu) - Cys(TR1) - Val - Leu - OH, Z - Asn - Leu - OMe, H - Asn - Leu - OMe, Z and H - Ser(tBu) - Asn - Leu - OMe, BOC - Cys (TR1) - Ser(tBu) - Asn - Leu - OMe and -NHNH 2 , BOC - Cys(TR1) - Ser(tBu) - Asn- Leu - Ser(tBu) - Thr(tBu) - -Cys(TR1) - Val - Leu- OH, BOC- # Cys-Ser-(tBu)-Asn-Leu-Ser(tBu)-Thr(tBu)Cys- Val - Leu OH, H - and Z - Tyr(tBu)-Try- OMe, H - and Z - Ala - Tyr(tBu) - Try - OMe, DPC - Ser(tBu) - Ala - Tyr(tBu)Try - OMe and -NHNH 2 Z - and H - Asn - Phe - NHNHBOC, Z - and H - Asn - Asn - Phe - NHNHBOC Z- and H Asn - Asn - Phe NHNHBOC, Z - and H - Leu- Asn - Asn - Phe - NHNH - BOC, Z - and H - "Asn - Leu - Asn - Asn, Phe- NHNHBOC, Z - Arg - Asn - Leu - Asn, - Asn- Phe - NHNHBOC, HCl and - NHNH 2 HCl, Z - Phe - Ser(tBu) - OMe and - NHNH 2 Z and H - Phe - Ser(tBu) - GlyOMe, Z - and HArg - Phe - Ser(tBu) - Sly - OMe, HBr, Z - and H - His - Arg - Phe - Ser(tBu) - Gly - OMe, HHis Arg Phe - Ser(tBu) - GlyOH, HOAc, Z- and H - Arg - Asn - Leu - Asn - Asn - Phe - His- Arg - Phe - Ser(tBu) - GlyOH, HOAc, DPCSer(tBu) - Ala - Tyr(tBu) - Try - Arg - Asn - Leu- Asn - Asn - Phe - His - Arg - Phe - Ser(tBu) - -Gly- OH, Z - Sly - Phe - Gly - Pro - OtBu and - OHZ - and H - Thr(tBu) - ProNH 2 , Z - and HGlu(OtBu)Thr(tBu) - ProNH 2 , Z - and H - Gly, Phe - Sly - Pro - Glu(OtBu) - Thr(tBu) - ProNH 2 - DPC - and H - Met - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - ProNH 2 , DPC - Ser (tBu) - Ala - Tyr(tBu) - Try - Arg - Asn - Leu, Asn - Asn - Phe - His - Arg - Phe - Ser(tBu-) Gly - OH ditosylate DPC - and H - Ser(tBu)- Ala - Tyr(tBu) - Try - Arg - Asn - Leu - Asn- Asn - Phe - His - Arg - Phe - Ser(tBu) - Gly- Met - Gly - Phe - Gly - Pro - Glu(OtBu) - Thr (tBu)ProNH 2 , BOCCys-Ser(tBu)-Asn-Leu-Ser.(tBu)-Thr(tBu)Cys Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try- Arg- Asn - Leu - Ash - Asn - Phe - His - Arg - Phe- Ser(tBu) - Gly - Met - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - ProNH 2 and BOC- # Cys-Ser (tBu) -Asn-Leu-Ser (tBu) - Thr (tBu) - Cys - Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try- Arg - Asn - Leu - Ash - Asn - Phe - His - Arg- Phe - Ser(tBu) - GlyOH; BOC and H - Val- Leu - OBzl, BOC - and H - Cys(Bzl) - Val- Leu - OBzl, BOC - and H - Ser - Thr - OBzl, BOC - and H - Asn - Leu - NHNHZ, BOCSer - Ash - Leu - NHNHZ and - NHNH 2 , BOC - Ser - Ash - Leu - Ser - Thr - OBzl and - OH, H - Ser - Asn. Leu - Ser , ,; Thr OH, BOC - Cys(Bzl) - Ser - Asn - Lent - Ser - Thr OH, BOC - Cys(Bzl) - Ser - Asn - Leu - Ser - Thr- Cys(Bzl) - Val - Leu OH, BOC - Cys - Ser- Asn - Leu - Ser - Thr - Cys - Val - Left OH, BOCI I Cys-Ser-Asn-Leu-Ser-Thr-Cys Val - Left OH and BOGCys-Ser-Asn-Leu-Ser-Thr-Cys Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try - Arg- Asn Len - Asn - Asn - Phe - His - Arg - Phe- Ser(tBu) - Gly - Met - Gly - Phe - ,- Gly - Pro- Glu(OtBu), Thr(tBu)ProNH 2 ; N - acetyl- # Cys Ser Asn - Leu - Ser - Thr - Cys - Val- Leu - OH, H - Ser - Ala - Tyr - Try - Arg - Asn- Leu - Asn - Asn - Phe - His - Arg - Phe - Ser- Oly Met - Gly - Phe - Gly - Pro - Olu - Thr- ProNH 2 diacetate; Z- and HThr(tBu) -Pro- OtBu; Z - and H - Glu(OtBu) - Thr(tBu)- Pro(OtBu), Z - and H - Gly - Phe - Gly - Pro- Glu(OtBu) - Thr(tBu) - Pro OtBu, DPC - and H - Met - Gly - Phe - Gly - Pro - Glu(OtBu)- Thr(tBu) - Pro OtBu; and BOC- # Cys-Ser(tBn)-Asn-Leu-Ser(tBn)-Thr-(tBu)-Cys- Val - Leu - Ser(tBu) - Ala - Tyr(tBu) - Try Arg- Asn - Leu - Asn - Asn - Phe - His - Arg - Phe - Ser(tBu) - Gly - Met - Gly - Phe - Gly - Pro - Olu(OtBu) - Thr(tBu) -Pro -OtBu.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1566167A CH517074A (en) | 1967-11-09 | 1967-11-09 | Hypocalcaemic peptides - with anti-inflammatory activity |
| CH176368A CH529105A (en) | 1968-02-06 | 1968-02-06 | Preparation of hypocalcaemic peptides |
| CH634768 | 1968-04-29 | ||
| CH666668 | 1968-05-04 | ||
| CH699968A CH498805A (en) | 1968-05-10 | 1968-05-10 | Prepn. of cystine-contg. peptides - used in the synthesis of long-chain peptides |
| CH750968 | 1968-05-21 | ||
| US81810969A | 1969-04-24 | 1969-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1243035A true GB1243035A (en) | 1971-08-18 |
Family
ID=27561059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52391/68A Expired GB1243035A (en) | 1967-11-09 | 1968-11-05 | New hypocalcaemic peptides and processes for their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE723588A (en) |
| CA (1) | CA992958A (en) |
| DE (1) | DE1806135A1 (en) |
| FR (1) | FR1593126A (en) |
| GB (1) | GB1243035A (en) |
| NL (1) | NL6815962A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003122A1 (en) * | 1978-01-12 | 1979-07-25 | Hoechst Aktiengesellschaft | Process for the preparation of cystein-containing peptides |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU673237B2 (en) * | 1992-12-31 | 1996-10-31 | University Of Washington | Derivatized calcitonins |
| US5698672A (en) * | 1995-04-04 | 1997-12-16 | Zymogenetics, Inc. | Synthetic calcitonin mimetics |
-
1968
- 1968-10-30 DE DE19681806135 patent/DE1806135A1/en active Pending
- 1968-11-05 GB GB52391/68A patent/GB1243035A/en not_active Expired
- 1968-11-06 CA CA034,471A patent/CA992958A/en not_active Expired
- 1968-11-07 FR FR1593126D patent/FR1593126A/fr not_active Expired
- 1968-11-08 NL NL6815962A patent/NL6815962A/xx unknown
- 1968-11-08 BE BE723588D patent/BE723588A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0003122A1 (en) * | 1978-01-12 | 1979-07-25 | Hoechst Aktiengesellschaft | Process for the preparation of cystein-containing peptides |
Also Published As
| Publication number | Publication date |
|---|---|
| CA992958A (en) | 1976-07-13 |
| BE723588A (en) | 1969-05-08 |
| FR1593126A (en) | 1970-05-25 |
| DE1806135A1 (en) | 1969-07-17 |
| NL6815962A (en) | 1969-05-13 |
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