CS207570B2 - Method of making the tetradecapeptide - Google Patents
Method of making the tetradecapeptide Download PDFInfo
- Publication number
- CS207570B2 CS207570B2 CS763695A CS369576A CS207570B2 CS 207570 B2 CS207570 B2 CS 207570B2 CS 763695 A CS763695 A CS 763695A CS 369576 A CS369576 A CS 369576A CS 207570 B2 CS207570 B2 CS 207570B2
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- CS
- Czechoslovakia
- Prior art keywords
- gly
- phe
- boc
- ala
- lys
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001944 cysteine derivatives Chemical class 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- VLIPDCLJOLBAIX-PMERELPUSA-N decyl (2R)-2-amino-3-tritylsulfanylpropanoate Chemical compound C(CCCCCCCCC)OC([C@@H](N)CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O VLIPDCLJOLBAIX-PMERELPUSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 108010050848 glycylleucine Proteins 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- XZKKRKCYSDIECD-JEDNCBNOSA-N methyl 2-[[(2s)-2-[(2-aminoacetyl)amino]propanoyl]amino]acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC(=O)CNC(=O)[C@H](C)NC(=O)CN XZKKRKCYSDIECD-JEDNCBNOSA-N 0.000 description 1
- QFHVQBBMXXVIPU-QMMMGPOBSA-N methyl 2-[[(2s)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)OC(C)(C)C QFHVQBBMXXVIPU-QMMMGPOBSA-N 0.000 description 1
- PBCPQORBPLWCFO-VIFPVBQESA-N methyl 2-[[(2s)-2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]propanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)CNC(=O)OC(C)(C)C PBCPQORBPLWCFO-VIFPVBQESA-N 0.000 description 1
- FGARWWXOVGWRAB-KBPBESRZSA-N methyl 2-[[(2s)-2-[[2-[[2-[[(2s)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetyl]amino]acetyl]amino]propanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C FGARWWXOVGWRAB-KBPBESRZSA-N 0.000 description 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 108091005601 modified peptides Proteins 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- OSAFIXGIDDHGSR-UHFFFAOYSA-N o-(2,3,4,5,6-pentachlorophenyl) 4,4,4-triphenylbutanethioate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=S)CCC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OSAFIXGIDDHGSR-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 108010073025 phenylalanylphenylalanine Proteins 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229940075620 somatostatin analogue Drugs 0.000 description 1
- 108010043680 somatostatin(7-10) Proteins 0.000 description 1
- 230000003294 somatostatinlike Effects 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JBAUZPKHNMHHJJ-QMMMGPOBSA-N tert-butyl n-[2-[[2-[[(2s)-1-[(2-hydrazinyl-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate Chemical compound NNC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)CNC(=O)OC(C)(C)C JBAUZPKHNMHHJJ-QMMMGPOBSA-N 0.000 description 1
- KVBMPSVKQLYEDF-VIFPVBQESA-N tert-butyl n-[2-[[2-[[2-[[(2s)-1-[(2-hydrazinyl-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate Chemical compound NNC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)CNC(=O)CNC(=O)OC(C)(C)C KVBMPSVKQLYEDF-VIFPVBQESA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 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
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides 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
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/583,947 US4081530A (en) | 1975-06-04 | 1975-06-04 | Extended chain derivatives of somatostatin |
| US59415875A | 1975-07-08 | 1975-07-08 | |
| US05/594,159 US4020157A (en) | 1975-07-08 | 1975-07-08 | Shortened analogs of somatostatin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207570B2 true CS207570B2 (en) | 1981-08-31 |
Family
ID=27416418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS763695A CS207570B2 (en) | 1975-06-04 | 1976-06-03 | Method of making the tetradecapeptide |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115043928A (zh) * | 2022-06-22 | 2022-09-13 | 四川吉晟生物医药有限公司 | 一种生长抑素的制备方法 |
| FR3155702A1 (fr) | 2023-11-27 | 2025-05-30 | Id4Us | Dispositif de capture à ultrasons et à dispense de lubrifiant sur sa surface de capture |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904594A (en) * | 1973-07-02 | 1975-09-09 | Salk Inst For Biological Studi | Somatostatin and acylated des-(ala' 1', gly' 2') derivatives thereof |
| DE2416048A1 (de) * | 1974-04-03 | 1975-10-30 | Hoechst Ag | Neue peptide mit biologischer wirkung |
| DE2519656A1 (de) * | 1974-05-13 | 1975-11-27 | Sandoz Ag | Neue peptide und verfahren zu ihrer herstellung |
| US3931140A (en) * | 1975-01-27 | 1976-01-06 | American Home Products Corporation | (H-gly-gly-tyr-ala)1 -somatostatin |
-
1976
- 1976-06-03 FR FR7616823A patent/FR2313077A1/fr active Granted
- 1976-06-03 GB GB22906/76A patent/GB1545818A/en not_active Expired
- 1976-06-03 CH CH706676A patent/CH616402A5/fr not_active IP Right Cessation
- 1976-06-03 SU SU762366254A patent/SU639446A3/ru active
- 1976-06-03 CS CS763695A patent/CS207570B2/cs unknown
- 1976-06-03 NL NL7606008A patent/NL7606008A/xx not_active Application Discontinuation
- 1976-06-03 SE SE7606314A patent/SE7606314L/xx not_active Application Discontinuation
- 1976-06-04 DE DE19762625330 patent/DE2625330A1/de not_active Withdrawn
- 1976-06-04 JP JP51066408A patent/JPS5236682A/ja active Pending
- 1976-06-06 IL IL49731A patent/IL49731A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU639446A3 (ru) | 1978-12-25 |
| SE7606314L (sv) | 1976-12-05 |
| IL49731A0 (en) | 1976-08-31 |
| CH616402A5 (en) | 1980-03-31 |
| JPS5236682A (en) | 1977-03-22 |
| FR2313077A1 (fr) | 1976-12-31 |
| GB1545818A (en) | 1979-05-16 |
| FR2313077B1 (enrdf_load_stackoverflow) | 1978-11-17 |
| DE2625330A1 (de) | 1976-12-16 |
| NL7606008A (nl) | 1976-12-07 |
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