DE2416048A1 - Neue peptide mit biologischer wirkung - Google Patents
Neue peptide mit biologischer wirkungInfo
- Publication number
- DE2416048A1 DE2416048A1 DE19742416048 DE2416048A DE2416048A1 DE 2416048 A1 DE2416048 A1 DE 2416048A1 DE 19742416048 DE19742416048 DE 19742416048 DE 2416048 A DE2416048 A DE 2416048A DE 2416048 A1 DE2416048 A1 DE 2416048A1
- Authority
- DE
- Germany
- Prior art keywords
- phe
- thr
- mmol
- peptide
- ser
- 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.)
- Pending
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 82
- 102000004196 processed proteins & peptides Human genes 0.000 title claims description 31
- 230000004071 biological effect Effects 0.000 title description 4
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- 239000000243 solution Substances 0.000 claims description 47
- -1 benzyl ester Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 239000000725 suspension Substances 0.000 claims description 16
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- 239000003755 preservative agent Substances 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 235000001014 amino acid Nutrition 0.000 claims description 11
- 229940024606 amino acid Drugs 0.000 claims description 11
- 150000001413 amino acids Chemical group 0.000 claims description 11
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 10
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- 238000006243 chemical reaction Methods 0.000 claims description 9
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- 239000011734 sodium Substances 0.000 claims description 9
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
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- 230000000694 effects Effects 0.000 claims description 6
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
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- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 102000007327 Protamines Human genes 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- 229950008679 protamine sulfate Drugs 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001433 C-terminal amino-acid group Chemical group 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
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- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000008282 halocarbons Chemical class 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 150000003751 zinc Chemical class 0.000 claims 2
- 101800001415 Bri23 peptide Proteins 0.000 claims 1
- 102400000107 C-terminal peptide Human genes 0.000 claims 1
- 101800000655 C-terminal peptide Proteins 0.000 claims 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 230000004907 flux Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 150000001875 compounds Chemical class 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 28
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 23
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- 239000002244 precipitate Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 12
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- 235000019445 benzyl alcohol Nutrition 0.000 description 11
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- NHXLMOGPVYXJNR-UHFFFAOYSA-N srif Chemical compound N1C(=O)C(C(C)O)NC(=O)C(CCCCN)NC(=O)C(CC=2C3=CC=CC=C3NC=2)NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC=2C=CC=CC=2)NC(=O)C(CC(N)=O)NC(=O)C(CCCCN)NC(=O)C(NC(=O)CNC(=O)C(C)N)CSSCC(C(O)=O)NC(=O)C(CO)NC(=O)C(C(O)C)NC(=O)C1CC1=CC=CC=C1 NHXLMOGPVYXJNR-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000375 suspending agent Substances 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 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
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Endocrinology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742416048 DE2416048A1 (de) | 1974-04-03 | 1974-04-03 | Neue peptide mit biologischer wirkung |
| NL7503724A NL7503724A (nl) | 1974-04-03 | 1975-03-27 | Nieuwe peptiden met biologische werking. |
| LU72178A LU72178A1 (enrdf_load_stackoverflow) | 1974-04-03 | 1975-04-01 | |
| DK140475A DK140475A (enrdf_load_stackoverflow) | 1974-04-03 | 1975-04-02 | |
| SE7503810A SE7503810L (sv) | 1974-04-03 | 1975-04-03 | Nya peptider med biologisk verkan. |
| JP4074775A JPS50154278A (enrdf_load_stackoverflow) | 1974-04-03 | 1975-04-03 | |
| BE155064A BE827530A (fr) | 1974-04-03 | 1975-04-03 | Nouveaux peptides a activite biologique, leur procede de preparation et leurs applications |
| FR7510392A FR2266516A1 (en) | 1974-04-03 | 1975-04-03 | Somatostatin peptide analogues having prolonged activity - inhibit secretion of pituitary growth hormone and glucagon and are used to treat diabetes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742416048 DE2416048A1 (de) | 1974-04-03 | 1974-04-03 | Neue peptide mit biologischer wirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2416048A1 true DE2416048A1 (de) | 1975-10-30 |
Family
ID=5911970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742416048 Pending DE2416048A1 (de) | 1974-04-03 | 1974-04-03 | Neue peptide mit biologischer wirkung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS50154278A (enrdf_load_stackoverflow) |
| BE (1) | BE827530A (enrdf_load_stackoverflow) |
| DE (1) | DE2416048A1 (enrdf_load_stackoverflow) |
| DK (1) | DK140475A (enrdf_load_stackoverflow) |
| FR (1) | FR2266516A1 (enrdf_load_stackoverflow) |
| LU (1) | LU72178A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7503724A (enrdf_load_stackoverflow) |
| SE (1) | SE7503810L (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859785A4 (en) * | 1995-09-29 | 1999-05-26 | Biomeasure Inc | SOMATOSTATIN CYCLIC PEPTIDE ANALOGS |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2313077A1 (fr) * | 1975-06-04 | 1976-12-31 | Ayerst Mckenna & Harrison | Analogues de la somatostatine et leur preparation |
| CA1083143A (en) * | 1976-01-02 | 1980-08-05 | Nedumparambil A. Abraham | Carba derivatives of somatostatin and process therefor |
| US4118380A (en) * | 1977-07-25 | 1978-10-03 | Ayerst, Mckenna & Harrison Limited | Decapeptide analogs of somatostatin |
| US4139526A (en) * | 1977-12-01 | 1979-02-13 | Merck & Co., Inc. | Somatostatin analogs |
| US4140767A (en) * | 1977-12-01 | 1979-02-20 | Merck & Co., Inc. | Somatostatin analogs |
| US4202802A (en) * | 1978-10-02 | 1980-05-13 | Eli Lilly And Company | Peptides related to somatostatin |
| IL60214A0 (en) * | 1979-06-11 | 1980-09-16 | Lilly Co Eli | Peptides related to somatostatin |
| US4244947A (en) * | 1979-08-13 | 1981-01-13 | Ayerst Mckenna And Harrison Inc. | Carba decapeptide derivatives of [TYR6 ]-somatostatin |
| US4485101A (en) * | 1983-10-11 | 1984-11-27 | Administrators Of The Tulane Educational Fund | Peptides |
-
1974
- 1974-04-03 DE DE19742416048 patent/DE2416048A1/de active Pending
-
1975
- 1975-03-27 NL NL7503724A patent/NL7503724A/xx unknown
- 1975-04-01 LU LU72178A patent/LU72178A1/xx unknown
- 1975-04-02 DK DK140475A patent/DK140475A/da not_active Application Discontinuation
- 1975-04-03 JP JP4074775A patent/JPS50154278A/ja active Pending
- 1975-04-03 FR FR7510392A patent/FR2266516A1/fr not_active Withdrawn
- 1975-04-03 SE SE7503810A patent/SE7503810L/ not_active Application Discontinuation
- 1975-04-03 BE BE155064A patent/BE827530A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859785A4 (en) * | 1995-09-29 | 1999-05-26 | Biomeasure Inc | SOMATOSTATIN CYCLIC PEPTIDE ANALOGS |
| US6001801A (en) * | 1995-09-29 | 1999-12-14 | Biomeasure, Inc. | Cyclic peptide analogs of somatostatin |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7503724A (nl) | 1975-10-07 |
| JPS50154278A (enrdf_load_stackoverflow) | 1975-12-12 |
| SE7503810L (sv) | 1975-10-06 |
| BE827530A (fr) | 1975-10-03 |
| DK140475A (enrdf_load_stackoverflow) | 1975-10-04 |
| LU72178A1 (enrdf_load_stackoverflow) | 1977-02-01 |
| FR2266516A1 (en) | 1975-10-31 |
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