GB2004891A - Tetrapeptide amides - Google Patents
Tetrapeptide amidesInfo
- Publication number
- GB2004891A GB2004891A GB7836208A GB7836208A GB2004891A GB 2004891 A GB2004891 A GB 2004891A GB 7836208 A GB7836208 A GB 7836208A GB 7836208 A GB7836208 A GB 7836208A GB 2004891 A GB2004891 A GB 2004891A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- met
- formula
- chr
- 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.)
- Granted
Links
- 150000001408 amides Chemical class 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 241000700199 Cavia porcellus Species 0.000 abstract 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 abstract 1
- AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 abstract 1
- 102000003840 Opioid Receptors Human genes 0.000 abstract 1
- 108090000137 Opioid Receptors Proteins 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 210000003405 ileum Anatomy 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Tetrapeptide amides of the formula <IMAGE> wherein R<1> is H, C1-C4 alkyl, C3-C5 alkenyl, propargyl, C4-C8 cycloalkyl- methyl or phenyl (C1-C3)alkyl; R<2> is H or C1-C4 alkyl; A is D-Ser or D-Thr (each optionally substituted on the beta -hydroxyl by C1-C4 alkyl) or D-Met, D-Met(O) or D-Met(O2) or a D-radical of formula NH.CHR<4>.CO(R<4> is C1-C5 alkyl); B is an L-radical of formula NR<6>.CHR<8>.CO (R<6> is H or C1-C4 alkyl; R<8> is CH2Ar wherein Ar is phenyl optionally substituted by Cl, CH3, OH or CH3O); R<3> is H, C1-C10 alkyl, phenyl or phenyl (C1-C6) alkyl; n is 2-5, p is 1-5 and r is 1 or 2. The compounds exhibit pharmacological activity when tested in the transmurally stimulated guinea pig ileum preparation indicating their affinity for opiate receptor sites and their utility for example as analgesics.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7836208A GB2004891B (en) | 1977-09-29 | 1978-09-08 | Organic compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4047677 | 1977-09-29 | ||
| GB7836208A GB2004891B (en) | 1977-09-29 | 1978-09-08 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2004891A true GB2004891A (en) | 1979-04-11 |
| GB2004891B GB2004891B (en) | 1982-02-24 |
Family
ID=26264417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7836208A Expired GB2004891B (en) | 1977-09-29 | 1978-09-08 | Organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2004891B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030845A3 (en) * | 1979-12-17 | 1981-11-04 | Eli Lilly And Company | Pharmacologically active peptides, their preparation and pharmaceutical compositions containing them |
-
1978
- 1978-09-08 GB GB7836208A patent/GB2004891B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030845A3 (en) * | 1979-12-17 | 1981-11-04 | Eli Lilly And Company | Pharmacologically active peptides, their preparation and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2004891B (en) | 1982-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |