CH403788A - Verfahren zur Herstellung neuer Heptapeptide - Google Patents

Verfahren zur Herstellung neuer Heptapeptide

Info

Publication number: CH403788A
Authority: CH; Switzerland
Prior art keywords: amino; valyl; lower alkyl; histidyl; tyrosyl
Prior art date: 1958-06-13

Application number

CH6053958A

Other languages

German (de)

English (en)

Inventor

Schwyzer Robert Dr Prof

Bernhard Dr Riniker

Original Assignee

Ciba Geigy

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.)

1958-06-13

Filing date

1958-06-13

Publication date

1965-12-15

1958-06-13 Application filed by Ciba Geigy filed Critical Ciba Geigy

1958-06-13 Priority to CH6053958A priority Critical patent/CH403788A/de

1959-05-18 Priority to ES0249444A priority patent/ES249444A1/es

1960-08-05 Priority to FR835057A priority patent/FR110M/fr

1965-12-15 Publication of CH403788A publication Critical patent/CH403788A/de

Links

238000000034 method Methods 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
-1 alkyl acetic acid Chemical compound 0.000 claims description 8
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 5
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229960002449 glycine Drugs 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
229960004441 tyrosine Drugs 0.000 claims description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 2
229930064664 L-arginine Natural products 0.000 claims description 2
235000014852 L-arginine Nutrition 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
229960005190 phenylalanine Drugs 0.000 claims description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
150000007514 bases Chemical class 0.000 claims 1
150000001718 carbodiimides Chemical class 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
108090000765 processed proteins & peptides Proteins 0.000 description 8
108010072661 Angiotensin Amide Proteins 0.000 description 7
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 7
150000001413 amino acids Chemical group 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000843 powder Substances 0.000 description 4
102000004196 processed proteins & peptides Human genes 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229960002885 histidine Drugs 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
229930182821 L-proline Natural products 0.000 description 2
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229960005261 aspartic acid Drugs 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000009826 distribution Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
229960002429 proline Drugs 0.000 description 2
QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
229930182844 L-isoleucine Natural products 0.000 description 1
235000019454 L-leucine Nutrition 0.000 description 1
239000004395 L-leucine Substances 0.000 description 1
DKQDBUYHLFIUTC-UHFFFAOYSA-N [Na].O.C(C)(C)O Chemical compound [Na].O.C(C)(C)O DKQDBUYHLFIUTC-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
229960002319 barbital Drugs 0.000 description 1
IBJSYFJUWZNNKN-UHFFFAOYSA-N benzene;chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl.C1=CC=CC=C1 IBJSYFJUWZNNKN-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000012888 bovine serum Substances 0.000 description 1
KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
229950003188 isovaleryl diethylamide Drugs 0.000 description 1
229960003136 leucine Drugs 0.000 description 1
125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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 description 1
239000000463 material Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 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
OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
125000002233 tyrosyl group Chemical group 0.000 description 1
229960004295 valine Drugs 0.000 description 1
125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 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
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/14—Angiotensins: Related peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Life Sciences & Earth Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Vascular Medicine (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CH6053958A 1958-06-13 1958-06-13 Verfahren zur Herstellung neuer Heptapeptide CH403788A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH6053958A CH403788A (de)	1958-06-13	1958-06-13	Verfahren zur Herstellung neuer Heptapeptide
ES0249444A ES249444A1 (es)	1958-06-13	1959-05-18	Procedimiento para la obtenciën de nuevos polipepturos
FR835057A FR110M (fr)	1958-06-13	1960-08-05	Nouvel heptapeptide de la formule l-arginyl-l-valyl-l-tyrosyl-l-α-alcoyl(inférieur)-α-amino-acétyl-l-histidyl-l-propyl-l-phénylalanine utilisable en thérapeutique.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6053958A CH403788A (de)	1958-06-13	1958-06-13	Verfahren zur Herstellung neuer Heptapeptide

Publications (1)

Publication Number	Publication Date
CH403788A true CH403788A (de)	1965-12-15

Family

ID=4523029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6053958A CH403788A (de)	1958-06-13	1958-06-13	Verfahren zur Herstellung neuer Heptapeptide

Country Status (3)

Country	Link
CH (1)	CH403788A (fr)
ES (1)	ES249444A1 (fr)
FR (1)	FR110M (fr)

1958
- 1958-06-13 CH CH6053958A patent/CH403788A/de unknown
1959
- 1959-05-18 ES ES0249444A patent/ES249444A1/es not_active Expired
1960
- 1960-08-05 FR FR835057A patent/FR110M/fr not_active Expired

Also Published As

Publication number	Publication date
FR110M (fr)	1961-01-09
ES249444A1 (es)	1960-01-16

Publication	Publication Date	Title
DE2321174C2 (de)	1982-04-15	Nonapeptidamid und Verfahren zu ihrer Herstellung
DE2446005C2 (de)	1982-03-18	Nonapeptidamide und Verfahren zu ihrer Herstellung
DE2435027C2 (de)	1981-11-26	Nonapeptidamide und Verfahren zu ihrer Herstellung
DE69217763T2 (de)	1997-07-10	Hexapeptide
DD139710A5 (de)	1980-01-16	Verfahren zur herstellung von peptiden
CH615904A5 (en)	1980-02-29	Process for the preparation of L-leucine-13-motilin
DE3888718T2 (de)	1994-07-14	Chemische Derivate von GHL-Cu.
DD255164A5 (de)	1988-03-23	Verfahren zur herstellung von gonadoliberin-derivaten
DE2633976A1 (de)	1977-02-10	Tripeptidderivate, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
EP0003028B1 (fr)	1981-08-05	Analogues de la bêta h-endorphine, préparations les contenant et leur procédé de préparation
CH429754A (de)	1967-02-15	Verfahren zur Herstellung eines neuen Hexapeptids
CH403788A (de)	1965-12-15	Verfahren zur Herstellung neuer Heptapeptide
DE1518282C3 (de)	1974-05-02	Phe hoch 2 -Om hoch 8 -Oxytocin und Verfahren zu dessen Herstellung
DE2343035A1 (de)	1975-03-06	Tripeptide mit antidepressiver und prolactinausschuettender wirkung und verfahren zu ihrer herstellung
DE2158123A1 (de)	1972-06-08	Neue pharmazeutische Präparate
AT234922B (de)	1964-07-27	Verfahren zur Herstellung neuer Polypeptide
DE2532823A1 (de)	1976-02-12	Neue polypeptide
DE1130816B (de)	1962-06-07	Verfahren zur Herstellung neuer hypertensinwirksamer Heptapeptide
DE2341775A1 (de)	1974-02-28	Verfahren zur herstellung von neuen, in n-terminaler stellung alpha-aminooxysaeuren enthaltenden peptiden mit acthwirkung
CH499497A (de)	1970-11-30	Verfahren zur Herstellung neuer Polypeptide
CH437337A (de)	1967-06-15	Verfahren zur Herstellung von Peptiden
CH402879A (de)	1965-11-30	Verfahren zur Herstellung neuer Oktapeptide
DE2311786A1 (de)	1973-09-20	Verfahren zur herstellung von peptiden
DE1130817B (de)	1962-06-07	Verfahren zur Herstellung neuer hypertensinwirksamer Oktapeptide
EP0424670B1 (fr)	1995-02-22	Hexapeptides à activité ZNS exerçant une action antiamnestique