CH429754A - Verfahren zur Herstellung eines neuen Hexapeptids - Google Patents

Verfahren zur Herstellung eines neuen Hexapeptids

Info

Publication number: CH429754A
Authority: CH; Switzerland
Prior art keywords: solution; glycyl; leucyl; carbobenzoxy; alanyl
Prior art date: 1961-10-05

Application number

CH1155562A

Other languages

German (de)

English (en)

Inventor

Chillemi Francesco

Original Assignee

Farmaceutici Italia

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.)

1961-10-05

Filing date

1962-10-02

Publication date

1967-02-15

1962-10-02 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1967-02-15 Publication of CH429754A publication Critical patent/CH429754A/de

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 3
125000006239 protecting group Chemical group 0.000 claims description 7
YSDLIYZLOTZZNP-UWVGGRQHSA-N Gly-Leu-Met Chemical compound CSCC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)CN YSDLIYZLOTZZNP-UWVGGRQHSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
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 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
229920001184 polypeptide Polymers 0.000 description 6
108090000765 processed proteins & peptides Proteins 0.000 description 6
102000004196 processed proteins & peptides Human genes 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
-1 carbobenzoxy, carbo-t-butoxy Chemical group 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010020772 Hypertension Diseases 0.000 description 3
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 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
GSYTVXOARWSQSV-BYPYZUCNSA-N L-methioninamide Chemical compound CSCC[C@H](N)C(N)=O GSYTVXOARWSQSV-BYPYZUCNSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
UIHPNZDZCOEZEN-YFKPBYRVSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound COC(=O)[C@@H](N)CCSC UIHPNZDZCOEZEN-YFKPBYRVSA-N 0.000 description 2
YXMMTUJDQTVJEN-WDSKDSINSA-N methyl (2s,3s)-2-amino-3-methylpentanoate Chemical compound CC[C@H](C)[C@H](N)C(=O)OC YXMMTUJDQTVJEN-WDSKDSINSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
239000000047 product Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
230000001148 spastic effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
230000002792 vascular Effects 0.000 description 2
RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
XUXRXWLKUYPGMZ-UHFFFAOYSA-N 2-(tritylamino)acetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCC(=O)O)C1=CC=CC=C1 XUXRXWLKUYPGMZ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
201000004569 Blindness Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000012458 free base Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
239000000810 peripheral vasodilating agent Substances 0.000 description 1
229960002116 peripheral vasodilator Drugs 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
210000001210 retinal vessel Anatomy 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
230000000304 vasodilatating effect Effects 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
- C07K7/22—Tachykinins, e.g. Eledoisins, Substance P; Related peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
- A61K38/095—Oxytocins; Vasopressins; Related peptides
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Epidemiology (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Gastroenterology & Hepatology (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CH1155562A 1961-10-05 1962-10-02 Verfahren zur Herstellung eines neuen Hexapeptids CH429754A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT1798361		1961-10-05
IT216162		1962-02-05

Publications (1)

Publication Number	Publication Date
CH429754A true CH429754A (de)	1967-02-15

Family

ID=26325222

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1155562A CH429754A (de)	1961-10-05	1962-10-02	Verfahren zur Herstellung eines neuen Hexapeptids

Country Status (7)

Country	Link
CH (1)	CH429754A (fr)
DE (1)	DE1518133B1 (fr)
DK (2)	DK104307C (fr)
ES (1)	ES281304A1 (fr)
FR (1)	FR2822M (fr)
GB (1)	GB984810A (fr)
SE (1)	SE302617B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1681495B (zh)	2002-08-19	2010-05-12	辉瑞产品公司	用于治疗过度增生性疾病的组合物
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
US8383660B2 (en)	2006-03-10	2013-02-26	Pfizer Inc.	Dibenzyl amine compounds and derivatives
US7919506B2 (en)	2006-03-10	2011-04-05	Pfizer Inc.	Dibenzyl amine compounds and derivatives
US8404896B2 (en)	2006-12-01	2013-03-26	Bristol-Myers Squibb Company	N-((3-benzyl)-2,2-(bis-phenyl)-propan-1-amine derivatives as CETP inhibitors for the treatment of atherosclerosis and cardiovascular diseases
BR112015026513A2 (pt)	2013-04-17	2017-07-25	Pfizer	derivados de n-piperidin-3-ilbenzamida para tratar as doenças cardiovasculares
WO2016055901A1 (fr)	2014-10-08	2016-04-14	Pfizer Inc.	Composés d'amide substitué
RS66416B1 (sr)	2019-01-18	2025-02-28	Astrazeneca Ab	6'-[[(1s,3s)-3-[[5-(difluorometoksi)-2-pirimidinil]amino]ciklopentil]amino][1(2h),3'-bipiridin]-2-on kao inhibitor pcsk9 i metode njegove primene

1962
- 1962-10-01 GB GB37178/62A patent/GB984810A/en not_active Expired
- 1962-10-01 DE DE19621518133 patent/DE1518133B1/de active Pending
- 1962-10-02 CH CH1155562A patent/CH429754A/de unknown
- 1962-10-03 DK DK428662AA patent/DK104307C/da active
- 1962-10-03 FR FR911147A patent/FR2822M/fr not_active Expired
- 1962-10-03 DK DK352664AA patent/DK108976C/da active
- 1962-10-04 SE SE10643/62A patent/SE302617B/xx unknown
- 1962-10-04 ES ES281304A patent/ES281304A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2822M (fr)	1964-10-05
DK104307C (da)	1966-05-02
SE302617B (fr)	1968-07-29
DE1518133B1 (de)	1970-08-20
DK108976C (da)	1968-03-04
GB984810A (en)	1965-03-03
ES281304A1 (es)	1963-04-16

Publication	Publication Date	Title
EP0150263B1 (fr)	1990-06-20	Dérivés de l'acide cis, endo-2-azabicyclo-[3.3.0]-octane-3-carboxylique, procédé pour leur préparation, médicaments les contenant et leur application
US4053588A (en)	1977-10-11	Pharmaceutical preparations having psychotropic activity and process for their manufacture
EP0119161B1 (fr)	1989-06-28	Dérivés de benzazocinone et benzazoninon, leur procédé de préparation, préparations pharmaceutiques contenant ces composés, et leur application thérapeutique
DE68926804T2 (de)	1996-12-12	Neuropeptid Y-Agonisten und partielle Agonisten
CH629475A5 (de)	1982-04-30	Verfahren zur herstellung von polypeptiden.
EP0046953A2 (fr)	1982-03-10	Dérivés des acides aminés, leurs procédés de préparation, compositions les contenant et leur application
DE3122479A1 (de)	1982-06-16	N-(vinblastin-23-oyl)-aminosaeurederivate
DE3508251A1 (de)	1986-09-11	Dipeptide
EP0111873A1 (fr)	1984-06-27	Dérivés de l'acide cis, endo-aza-2 bicyclo(5.3.0)décane-carboxylique-3, procédé pour leur préparation, compositions les contenant et leur application
DE2946909A1 (de)	1981-06-04	Neue tetrahydroisochinolinderivate
EP0051301A1 (fr)	1982-05-12	Acides 1-carboxy-azaalcoyl-indoline-2-carboxyliques, procédé pour les préparer, compositions pharmaceutiques les contienant, ainsi que leur application thérapeutique
CH650519A5 (de)	1985-07-31	Auf das zentrale nervensystem wirkende tripeptide und verfahren zur herstellung derselben.
EP0025897A2 (fr)	1981-04-01	Peptides et procédé pour leur préparation
CH429754A (de)	1967-02-15	Verfahren zur Herstellung eines neuen Hexapeptids
DE2730549A1 (de)	1978-01-19	Peptidderivate und deren herstellung
DE2632396C2 (de)	1982-11-25	Bestatin-Analoga, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
EP1483285B1 (fr)	2008-05-07	INHIBITEURS DU FACTEUR DE COAGULATION Xa, LEUR PRODUCTION ET LEUR UTILISATION
DE3446997C2 (fr)	1989-12-07
DE69431603T2 (de)	2003-03-13	Oligopeptide hergeleitet von fragmenten des c-reaktiven proteins
EP0267179B1 (fr)	1993-02-17	Composés de cystéine, leur préparation et leur emploi
DE2633976A1 (de)	1977-02-10	Tripeptidderivate, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
DE3700166A1 (de)	1987-07-09	In der 6-stellung einen aromatischen aminocarbonsaeurerest aufweisende nonapeptidaethylamide beziehungsweise decapeptidamide, verfahren zur herstellung derselben und diese enthaltende arzneimittel beziehungsweise vermehrungsbiologisch wirksame mittel sowie ihre verwendung
CH434286A (de)	1967-04-30	Verfahren zur Herstellung eines neuen Hendekapeptids
DE3245269A1 (de)	1983-07-21	N-(vinblastinoyl-23)-derivate von aminosaeuren, ihre herstellung und therapeutische anwendung
DE68913936T2 (de)	1994-07-07	Retro-Inverso-Thrymopentin-Analoge, Verfahren zu deren Herstellung und deren Verwendung für die Zubereitung von pharmazeutischen Zusammensetzungen.