CH657861A5 - Lysin-tryptophan-oligopeptide und verfahren zur herstellung solcher verbindungen. - Google Patents

Lysin-tryptophan-oligopeptide und verfahren zur herstellung solcher verbindungen. Download PDF

Info

Publication number: CH657861A5
Authority: CH; Switzerland
Prior art keywords: lys; conh; formula; stage; compound
Prior art date: 1981-04-23

Application number

CH2266/82A

Other languages

German (de)

English (en)

Inventor

Puigsubira Jose Maria Jorba

Original Assignee

Puigsubira Jose Maria Jorba

Priority date (The priority date 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 date listed.)

1981-04-23

Filing date

1982-04-15

Publication date

1986-09-30

1982-04-15 Application filed by Puigsubira Jose Maria Jorba filed Critical Puigsubira Jose Maria Jorba

1986-09-30 Publication of CH657861A5 publication Critical patent/CH657861A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 20
102000015636 Oligopeptides Human genes 0.000 title description 2
108010038807 Oligopeptides Proteins 0.000 title description 2
239000006035 Tryptophane Substances 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
229960004799 tryptophan Drugs 0.000 title 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 23
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 12
108090000765 processed proteins & peptides Proteins 0.000 claims description 10
-1 amino acid ester Chemical class 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
239000004472 Lysine Substances 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 6
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 5
102000004196 processed proteins & peptides Human genes 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
238000006386 neutralization reaction Methods 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
125000005454 tryptophanyl group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
230000003078 antioxidant effect Effects 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000006242 amine protecting group Chemical group 0.000 claims 2
239000000243 solution Substances 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
239000002585 base Substances 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
239000012047 saturated solution Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
239000002243 precursor Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000006340 racemization Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 1
AYGXDXVGROLVJK-UHFFFAOYSA-N 1-chloro-2-nitrosobenzene Chemical compound ClC1=CC=CC=C1N=O AYGXDXVGROLVJK-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
XNFNGGQRDXFYMM-PPHPATTJSA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 XNFNGGQRDXFYMM-PPHPATTJSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 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
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
- 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
- C07K5/06086—Dipeptides with the first amino acid being basic
- 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
- C07K5/1019—Tetrapeptides with the first amino acid being basic
- 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)
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)

CH2266/82A 1981-04-23 1982-04-15 Lysin-tryptophan-oligopeptide und verfahren zur herstellung solcher verbindungen. CH657861A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES501583A ES501583A0 (es)	1981-04-23	1981-04-23	Un procedimiento para la preparacion de oligopeptidos lisi- na-triptofano y de sus derivados y sales fisiologicamente aprovechables

Publications (1)

Publication Number	Publication Date
CH657861A5 true CH657861A5 (de)	1986-09-30

Family

ID=8482278

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH2266/82A CH657861A5 (de)	1981-04-23	1982-04-15	Lysin-tryptophan-oligopeptide und verfahren zur herstellung solcher verbindungen.

Country Status (10)

Country	Link
BE (1)	BE892932A (it)
CH (1)	CH657861A5 (it)
DE (1)	DE3213501A1 (it)
DK (1)	DK179682A (it)
ES (1)	ES501583A0 (it)
FR (1)	FR2504525B1 (it)
GB (1)	GB2097404B (it)
IT (1)	IT1151728B (it)
NL (1)	NL8201649A (it)
SE (1)	SE8202414L (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3823464A1 (de) *	1988-07-11	1990-01-18	Asta Pharma Ag	Neue tryptophandipeptide
ITMI20061607A1 (it) *	2006-08-09	2008-02-10	Maria Vincenza Carriero	Peptidi con attivita farmacologica

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5116667A (it) *	1974-07-30	1976-02-10	Shionogi Seiyaku Kk

1981
- 1981-04-23 ES ES501583A patent/ES501583A0/es active Granted
1982
- 1982-04-10 DE DE19823213501 patent/DE3213501A1/de not_active Withdrawn
- 1982-04-15 CH CH2266/82A patent/CH657861A5/de not_active IP Right Cessation
- 1982-04-19 SE SE8202414A patent/SE8202414L/ not_active Application Discontinuation
- 1982-04-19 GB GB8211276A patent/GB2097404B/en not_active Expired
- 1982-04-20 IT IT20834/82A patent/IT1151728B/it active
- 1982-04-21 NL NL8201649A patent/NL8201649A/nl not_active Application Discontinuation
- 1982-04-22 FR FR8206966A patent/FR2504525B1/fr not_active Expired
- 1982-04-22 DK DK179682A patent/DK179682A/da not_active Application Discontinuation
- 1982-04-22 BE BE0/207896A patent/BE892932A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2097404B (en)	1985-05-30
NL8201649A (nl)	1982-11-16
IT1151728B (it)	1986-12-24
GB2097404A (en)	1982-11-03
FR2504525B1 (fr)	1986-10-24
SE8202414L (sv)	1982-10-24
ES8202788A1 (es)	1982-02-16
IT8220834A0 (it)	1982-04-20
FR2504525A1 (fr)	1982-10-29
ES501583A0 (es)	1982-02-16
DE3213501A1 (de)	1982-11-11
BE892932A (fr)	1982-08-16
DK179682A (da)	1982-10-24

Legal Events

Date	Code	Title	Description
1988-12-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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