DE3303345A1 - Cyclische peptide mit somatostatin-wirkung - Google Patents
Cyclische peptide mit somatostatin-wirkungInfo
- Publication number
- DE3303345A1 DE3303345A1 DE19833303345 DE3303345A DE3303345A1 DE 3303345 A1 DE3303345 A1 DE 3303345A1 DE 19833303345 DE19833303345 DE 19833303345 DE 3303345 A DE3303345 A DE 3303345A DE 3303345 A1 DE3303345 A1 DE 3303345A1
- Authority
- DE
- Germany
- Prior art keywords
- phe
- trp
- lys
- formula iii
- compound
- 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.)
- Withdrawn
Links
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- QUHKDFBPIFJBQU-UHFFFAOYSA-N cyclopenta[b]pyrrole-2-carboxylic acid Chemical compound C1=CC2=NC(C(=O)O)=CC2=C1 QUHKDFBPIFJBQU-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000030304 gastrointestinal bleeding Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N indolyl-2-carboxylic acid Natural products C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- VBUWHHLIZKOSMS-RIWXPGAOSA-N invicorp Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)C)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 VBUWHHLIZKOSMS-RIWXPGAOSA-N 0.000 description 1
- 210000004153 islets of langerhan Anatomy 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229960002101 secretin Drugs 0.000 description 1
- OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002325 somatostatin-secreting cell Anatomy 0.000 description 1
- 230000003294 somatostatinlike Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/16—Somatostatin; related peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833303345 DE3303345A1 (de) | 1983-02-02 | 1983-02-02 | Cyclische peptide mit somatostatin-wirkung |
| US06/575,703 US4621073A (en) | 1983-02-02 | 1984-01-31 | Cyclic peptides having somatostatin activity |
| KR1019840000444A KR850000468A (ko) | 1983-02-02 | 1984-01-31 | 사이클릭 펩타이드의 제조방법 |
| ES529301A ES8500219A1 (es) | 1983-02-02 | 1984-01-31 | Procedimiento para preparar un hexapeptido ciclico |
| AT84100934T ATE31314T1 (de) | 1983-02-02 | 1984-01-31 | Cyclische peptide mit somatostatin-wirkung. |
| EP84100934A EP0117447B1 (de) | 1983-02-02 | 1984-01-31 | Cyclische Peptide mit Somatostatin-Wirkung |
| DE8484100934T DE3468031D1 (en) | 1983-02-02 | 1984-01-31 | Cyclic peptides with somatostatin activity |
| GR73673A GR79752B (https=) | 1983-02-02 | 1984-02-01 | |
| ZA84739A ZA84739B (en) | 1983-02-02 | 1984-02-01 | Cyclic peptides having somatostatin activity |
| AU23997/84A AU566208B2 (en) | 1983-02-02 | 1984-02-01 | Cyclic peptides having somatostatin activity |
| CA000446519A CA1245638A (en) | 1983-02-02 | 1984-02-01 | Cyclic peptides having somatostatin activity |
| PT78046A PT78046B (de) | 1983-02-02 | 1984-02-01 | Cyclische peptide mit somatostatin-wirkung |
| IL70848A IL70848A (en) | 1983-02-02 | 1984-02-01 | Cyclic peptides having somatostatin activity,their preparation and pharmaceutical compositions comprising them |
| DK45784A DK45784A (da) | 1983-02-02 | 1984-02-01 | Cyclisk hexapeptid, dets fremstilling og anvendelse |
| IE243/84A IE56718B1 (en) | 1983-02-02 | 1984-02-01 | Cyclic peptides having somatostatin activity |
| JP59015296A JPS59141549A (ja) | 1983-02-02 | 1984-02-01 | ソマトスタチン作用を有する環状ペプチド |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833303345 DE3303345A1 (de) | 1983-02-02 | 1983-02-02 | Cyclische peptide mit somatostatin-wirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3303345A1 true DE3303345A1 (de) | 1984-08-02 |
Family
ID=6189751
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833303345 Withdrawn DE3303345A1 (de) | 1983-02-02 | 1983-02-02 | Cyclische peptide mit somatostatin-wirkung |
| DE8484100934T Expired DE3468031D1 (en) | 1983-02-02 | 1984-01-31 | Cyclic peptides with somatostatin activity |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484100934T Expired DE3468031D1 (en) | 1983-02-02 | 1984-01-31 | Cyclic peptides with somatostatin activity |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4621073A (https=) |
| EP (1) | EP0117447B1 (https=) |
| JP (1) | JPS59141549A (https=) |
| KR (1) | KR850000468A (https=) |
| AT (1) | ATE31314T1 (https=) |
| AU (1) | AU566208B2 (https=) |
| CA (1) | CA1245638A (https=) |
| DE (2) | DE3303345A1 (https=) |
| DK (1) | DK45784A (https=) |
| ES (1) | ES8500219A1 (https=) |
| GR (1) | GR79752B (https=) |
| IE (1) | IE56718B1 (https=) |
| IL (1) | IL70848A (https=) |
| PT (1) | PT78046B (https=) |
| ZA (1) | ZA84739B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505897A (en) * | 1983-04-18 | 1985-03-19 | The Administrators Of The Tulane Educational Fund | Cyclic pentapeptides displaying somatostatin antagonism and method of treatment of mammals therewith |
| US4612366A (en) * | 1985-06-17 | 1986-09-16 | Merck & Co., Inc. | Cyclic hexapeptide somatostatin analogs |
| US5073541A (en) * | 1987-11-18 | 1991-12-17 | Administrators Of The Tulane Educational Fund | Treatment of small cell lung cancer with somatostatin analogs |
| US5965694A (en) * | 1992-09-01 | 1999-10-12 | The Trustees Of The University Of Pennsylvania | Somatostatin mimics and synthetic methods therefor |
| US5700905A (en) * | 1992-09-01 | 1997-12-23 | The Trustees Of The University Of Pennsylvania | Synthetic somatostatin mimics |
| US6001960A (en) * | 1992-09-01 | 1999-12-14 | The Trustees Of The University Of Pennsylvania | Synthetic somatostatin mimics |
| GB0318682D0 (en) * | 2003-08-08 | 2003-09-10 | Novartis Ag | Organic compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4303583A (en) * | 1979-08-13 | 1981-12-01 | American Home Products Corporation | 1H,5H-[1,4]Thiazepino[4,3-a]indole-1,5-diones |
| NZ195303A (en) * | 1979-10-31 | 1984-10-19 | Merck & Co Inc | Cyclic hexapeptide somatostatin analogues,and pharmaceutical compositions |
| US4235886A (en) * | 1979-10-31 | 1980-11-25 | Merck & Co., Inc. | Cyclic hexapeptide somatostatin analogs |
| US4310518A (en) * | 1979-10-31 | 1982-01-12 | Merck & Co., Inc. | Cyclic hexapeptide somatostatin analogs |
| US4360516A (en) * | 1981-04-13 | 1982-11-23 | Merck & Co., Inc. | Modified D-retro cyclic hexapeptide somatostatin analogs |
-
1983
- 1983-02-02 DE DE19833303345 patent/DE3303345A1/de not_active Withdrawn
-
1984
- 1984-01-31 KR KR1019840000444A patent/KR850000468A/ko not_active Ceased
- 1984-01-31 AT AT84100934T patent/ATE31314T1/de not_active IP Right Cessation
- 1984-01-31 US US06/575,703 patent/US4621073A/en not_active Expired - Fee Related
- 1984-01-31 DE DE8484100934T patent/DE3468031D1/de not_active Expired
- 1984-01-31 ES ES529301A patent/ES8500219A1/es not_active Expired
- 1984-01-31 EP EP84100934A patent/EP0117447B1/de not_active Expired
- 1984-02-01 IL IL70848A patent/IL70848A/xx unknown
- 1984-02-01 GR GR73673A patent/GR79752B/el unknown
- 1984-02-01 ZA ZA84739A patent/ZA84739B/xx unknown
- 1984-02-01 CA CA000446519A patent/CA1245638A/en not_active Expired
- 1984-02-01 AU AU23997/84A patent/AU566208B2/en not_active Ceased
- 1984-02-01 JP JP59015296A patent/JPS59141549A/ja active Pending
- 1984-02-01 PT PT78046A patent/PT78046B/pt not_active IP Right Cessation
- 1984-02-01 DK DK45784A patent/DK45784A/da not_active Application Discontinuation
- 1984-02-01 IE IE243/84A patent/IE56718B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0117447A1 (de) | 1984-09-05 |
| CA1245638A (en) | 1988-11-29 |
| PT78046A (de) | 1984-03-01 |
| ES529301A0 (es) | 1984-10-01 |
| AU2399784A (en) | 1984-08-09 |
| ATE31314T1 (de) | 1987-12-15 |
| GR79752B (https=) | 1984-10-31 |
| IE56718B1 (en) | 1991-11-20 |
| JPS59141549A (ja) | 1984-08-14 |
| AU566208B2 (en) | 1987-10-15 |
| US4621073A (en) | 1986-11-04 |
| IE840243L (en) | 1984-08-02 |
| PT78046B (de) | 1986-07-15 |
| IL70848A0 (en) | 1984-05-31 |
| DK45784A (da) | 1984-08-03 |
| ZA84739B (en) | 1984-09-26 |
| IL70848A (en) | 1987-10-30 |
| EP0117447B1 (de) | 1987-12-09 |
| DK45784D0 (da) | 1984-02-01 |
| KR850000468A (ko) | 1985-02-27 |
| ES8500219A1 (es) | 1984-10-01 |
| DE3468031D1 (en) | 1988-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |