SU430546A1 - - Google Patents

Info

Publication number: SU430546A1
Authority: SU; USSR - Soviet Union
Prior art keywords: tre; gly; solution; asn; fal
Prior art date: 1969-10-14

Application number

SU1370715A

Other languages

English (en)

Russian (ru)

Other versions

SU430546A3 (2

Inventor

Иностранцы изобретени

Макс Бруггер Бруно Камбер Бернхард Риннкер Вернер Риттел

Зибер Петер

Хендрик Мари Гревен

фирма вительИностранна

Гейги Циба

Filing date

1969-10-14

Publication date

1974-05-30

1968-10-15 Priority claimed from CH1540168A external-priority patent/CH550774A/de

1969-10-14 Application filed filed Critical

1974-05-30 Application granted granted Critical

1974-05-30 Publication of SU430546A1 publication Critical patent/SU430546A1/ru

1974-05-30 Publication of SU430546A3 publication Critical patent/SU430546A3/ru

Links

ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 7
108090000765 processed proteins & peptides Proteins 0.000 description 7
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
102000004196 processed proteins & peptides Human genes 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
229960004015 calcitonin Drugs 0.000 description 5
229960003136 leucine Drugs 0.000 description 5
238000000034 method Methods 0.000 description 5
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000012634 fragment Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 3
239000004395 L-leucine Substances 0.000 description 3
235000019454 L-leucine Nutrition 0.000 description 3
SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000001184 hypocalcaemic effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
229960004295 valine Drugs 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
102000055006 Calcitonin Human genes 0.000 description 2
108060001064 Calcitonin Proteins 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 2
125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229940124277 aminobutyric acid Drugs 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
101000741445 Homo sapiens Calcitonin Proteins 0.000 description 1
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 1
QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-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
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
108010087924 alanylproline Proteins 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
150000001408 amides Chemical class 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
-1 chlorine ions Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
CXISHPLSAAGNQA-UHFFFAOYSA-N ethyl acetate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound CCOC(C)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O CXISHPLSAAGNQA-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
229940045644 human calcitonin Drugs 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
XGZVNVFLUGNOJQ-UHFFFAOYSA-N n,n-dimethylformamide;ethyl acetate Chemical compound CN(C)C=O.CCOC(C)=O XGZVNVFLUGNOJQ-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

SU1370715A 1968-10-15 1969-10-14 SU430546A3 (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1540168A CH550774A (de)	1968-10-15	1968-10-15	Verfahren zur herstellung neuer hypocalcaemischer peptide.

Publications (2)

Publication Number	Publication Date
SU430546A1 true SU430546A1 (2)	1974-05-30
SU430546A3 SU430546A3 (2)	1974-05-30

Family

ID=4408799

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1370715A SU430546A3 (2)	1968-10-15	1969-10-14

Country Status (3)

Country	Link
BR (1)	BR6913330D0 (2)
CH (1)	CH550774A (2)
SU (1)	SU430546A3 (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK0423326T3 (da) *	1989-04-21	1999-05-25	Tsumura & Co	Hidtil ukendt fysiologisk aktivt peptid og calcium-metabolisme-regulerende middel, der omfatter peptidet som effektiv besta
CN110343146B (zh) *	2019-07-12	2022-09-30	上海应用技术大学	一种蟹味菇呈味肽及其制备方法和应用

1968
- 1968-10-15 CH CH1540168A patent/CH550774A/de not_active IP Right Cessation
1969
- 1969-10-14 SU SU1370715A patent/SU430546A3/ru active
- 1969-10-15 BR BR21333069A patent/BR6913330D0/pt unknown

Publication	Publication Date	Title
Sarges et al.	1965	Gramicidin A. VI. The synthesis of valine-and isoleucine-gramicidin A
US4271068A (en)	1981-06-02	Process for the manufacture of cystine-containing peptides
US3705140A (en)	1972-12-05	Peptides related to the c-terminal sequence of cck-pz and caerulein
Zervas et al.	1965	On Cysteine and Cystine Peptides. III. Synthesis of a Fragment of Insulin Containing the Intrachain Disulfide Bridge1, 2
JPS58116443A (ja)	1983-07-11	新規ペプチドおよびその製法
CA1137467A (en)	1982-12-14	Process for the preparation of somatostatin
DK148085B (da)	1985-02-25	Dipeptidet pyrglu-his(2,4-dinitrophenyl)-oh og fremgangsmaade til fremstilling af lh-rh og lh-rh-analoge peptider under anvendelse af dette dipeptid
US3856770A (en)	1974-12-24	Psychopharmacologically active tetra-, penta-, hexa-, and heptapeptides
SU430546A1 (2)	1974-05-30
US3642763A (en)	1972-02-15	Protected glucagon and its hydrobromide salts
JPS5811941B2 (ja)	1983-03-05	ブラディキニン環状類似体
SU793385A3 (ru)	1980-12-30	Способ получени полипептида
Stoffel et al.	1961	Synthesis of structures related to bacitracin A
FR2557114A1 (fr)	1985-06-28	Nouveaux derives de la gonadoliberine, procede pour leur preparation et compositions pharmaceutiques les contenant
US4038282A (en)	1977-07-26	Pyridyl-4-methyl-succinimidocarbonate and process for its preparation
Blout et al.	1971	Synthesis of polypeptides and oligopeptides with the repeating sequence L-alanyl-L-prolylglycine
Katsoyannis	1961	Insulin Peptides. I. Synthesis of Cysteine-Containing Peptides Related to the A-Chain of Sheep Insulin
JPS61191696A (ja)	1986-08-26	血清胸腺因子ペプチド類似体
SU490284A3 (ru)	1975-10-30	Способ получени пептидов с последовательностью актг-человека,содержащих в -конечном положении аминооксикислоту
Brand et al.	1952	Optical Rotation of Peptides. V. Alanine Tetra-, Penta-and Hexapeptides1
Hase et al.	1973	SYMMETRICAL DISULFIDE BONDS AS S‐PROTECTING GROUPS AND THEIR CLEAVAGE BY DITHIOTHREITOL: SYNTHESIS OF OXYTOCIN WITH HIGH BIOLOGICAL ACTIVITY
Schattenkerk et al.	1973	Studies on polypeptides xiv synthesis of possible rennin substrates
Brand et al.	1951	Optical Rotation of Peptides. IV. Lysine Tripeptides1
JPH0157109B2 (2)	1989-12-04
Kitagawa et al.	1990	Solution synthesis of human peptide YY (hPYY)