BE724772A - - Google Patents

Info

Publication number: BE724772A
Authority: BE; Belgium
Prior art keywords: val; lys; pro; denotes; tyr
Prior art date: 1967-12-01

Application number

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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.)

1967-12-01

Filing date

1968-12-02

Publication date

1969-06-02

1967-12-01 Priority claimed from DE19671643378 external-priority patent/DE1643378A1/de

1968-12-02 Application filed filed Critical

1969-06-02 Publication of BE724772A publication Critical patent/BE724772A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 18
108090000765 processed proteins & peptides Proteins 0.000 claims description 18
JKHXYJKMNSSFFL-IUCAKERBSA-N Val-Lys Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN JKHXYJKMNSSFFL-IUCAKERBSA-N 0.000 claims description 11
108010073969 valyllysine Proteins 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 8
102000004196 processed proteins & peptides Human genes 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
VPGCVZRRBYOGCD-AVGNSLFASA-N Val-Lys-Val Chemical compound CC(C)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(O)=O VPGCVZRRBYOGCD-AVGNSLFASA-N 0.000 claims description 3
YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 claims description 3
150000001718 carbodiimides Chemical class 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
108010065920 Insulin Lispro Proteins 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
238000000746 purification Methods 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
-1 hydroxy, mercapto Chemical class 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
101800000414 Corticotropin Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229960000258 corticotropin Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
239000000275 Adrenocorticotropic Hormone Substances 0.000 description 1
GEWGINLVERFBCI-UHFFFAOYSA-N C=1([ClH]C[ClH][ClH]C1)O Chemical compound C=1([ClH]C[ClH][ClH]C1)O GEWGINLVERFBCI-UHFFFAOYSA-N 0.000 description 1
101100178983 Caenorhabditis elegans hyl-1 gene Proteins 0.000 description 1
101100098216 Caenorhabditis elegans rars-1 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102400000739 Corticotropin Human genes 0.000 description 1
MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
229930195711 D-Serine Natural products 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
102100027467 Pro-opiomelanocortin Human genes 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
150000001408 amides Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000008384 inner phase Substances 0.000 description 1
238000003754 machining Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000005292 vacuum distillation Methods 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
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/695—Corticotropin [ACTH]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

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

BE724772D 1967-12-01 1968-12-02 BE724772A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19671643378 DE1643378A1 (de)	1967-12-01	1967-12-01	Verfahren zur Herstellung von Peptiden mit ACTH-Aktivitaet

Publications (1)

Publication Number	Publication Date
BE724772A true BE724772A (de)	1969-06-02

Family

ID=5684305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE724772D BE724772A (de)	1967-12-01	1968-12-02

Country Status (1)

Country	Link
BE (1)	BE724772A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2070182A1 (de) *	1969-10-31	1971-09-10	Hoechst Ag
FR2085734A1 (de) *	1970-03-24	1971-12-31	Shionogi & Co

1968
- 1968-12-02 BE BE724772D patent/BE724772A/fr unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2070182A1 (de) *	1969-10-31	1971-09-10	Hoechst Ag
FR2085734A1 (de) *	1970-03-24	1971-12-31	Shionogi & Co

Publication	Publication Date	Title
EP0097071A1 (de)	1983-12-28	Benzhydrylsulfinylacetamid-Derivate und deren Verwendung in der Therapeutik
FR2460291A1 (fr)	1981-01-23	Nouveaux tripeptides agissant sur le systeme nerveux central et leur procede de preparation
LU83843A1 (fr)	1982-07-07	Nouveaux tri-, tetra- et pentapeptides, leur preparation et les medicaments qui les contiennent
Patel et al.	1970	Asymmetric syntheses of optically active α-amino acids by hydrocyanic acid addition to the optically active Schiff base
EP2816028B1 (de)	2019-11-27	Verfahren zur synthese von ramalin mittels eines glutaminsäurederivates und hydroxyanilin oder hydroxyanilin mit geschützter hydroxygruppe
PAUL et al.	1961	Some side reactions of nitro-L-arginine
BE897844A (fr)	1984-01-16	Alkylamides de tripeptides et de tetrapeptides biologiquement actifs, procede pour leur preparation et compositions
BE724772A (de)	1969-06-02
CH630892A5 (en)	1982-07-15	Process for preparing bestatin compounds.
US4028410A (en)	1977-06-07	Process of preparing 1,3-bis(2-chloroethyl)-1-nitrosourea
BE1005720A3 (fr)	1993-12-28	Procede de synthese peptidique et nouveaux intermediaires de synthese.
CH655727A5 (fr)	1986-05-15	Derives n-(vinblastinoyl-23) d'acides amines et composition pharmaceutique les contenant.
LU82079A1 (fr)	1980-04-23	Nouveau procede de synthese de la vindesine
FR2559764A1 (fr)	1985-08-23	Nouveaux carbonates a-chlores, leur procede de fabrication et leur application a la protection des fonctions amine des amino-acides
BE1001684A3 (fr)	1990-02-06	Procede pour la fabrication de monoglyceride-monosulfates detergents.
Borrows et al.	1949	S 44. The synthesis of thyroxine and related substances. Part III. The synthesis of thyroxine from 2: 6-dinitrodiphenyl ethers
Johnston et al.	1984	Studies on synthesis and anticancer activity of selected N-(2-fluoroethyl)-N-nitrosoureas
Harada et al.	1973	Sterically Controlled Syntheses of Optically Active Organic Compounds. XVII. Asymmetric Syntheses of Amino Acids by Addition of Benzoyl Cyanide to the Azomethine Compounds
Camp et al.	1955	A New Synthesis of Pentaerythritol Trinitrate
FR2515177A1 (fr)	1983-04-29	Nouveaux derives de 1-(aminophenyl)-2-amino-1-ethanol, leur procede de preparation et leur utilisation en therapeutique
CA1064033A (fr)	1979-10-09	Derives de tetrahydro m.oxazines substitutes, leur procede de preparation et leur application en therapeutique
EP0290313B1 (de)	1992-03-04	Verfahren zur Herstellung von aktivierten Nitrosocarbamaten
FR2505329A1 (fr)	1982-11-12	Esters 2-methoxyphenyliques d'amino-acides n-substitues, procede pour leur preparation et compositions pharmaceutiques les contenant
CH395961A (fr)	1965-07-31	Procédé de fabrication de carbamates organiques
Fedorov et al.	2014	Synthesis and antiischemic activity of dicarboxylic nitroxyalkylamides and nitroxyalkylimides

BE724772A - - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=5684305

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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