NO122483B - - Google Patents

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Info

Publication number: NO122483B
Authority: NO; Norway
Prior art keywords: tert; tbu; butyl; water; hours
Prior art date: 1967-08-19

Application number

NO3099/68A

Other languages

English (en)

Norwegian (no)

Inventor

E Wuensch

G Wendelberger

Original Assignee

Hoechst Ag

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.)

1967-08-19

Filing date

1968-08-07

Publication date

1971-07-05

1968-08-07 Application filed by Hoechst Ag filed Critical Hoechst Ag

1971-07-05 Publication of NO122483B publication Critical patent/NO122483B/no

Links

MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical group C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 18
102000051325 Glucagon Human genes 0.000 claims description 14
108060003199 Glucagon Proteins 0.000 claims description 14
229960004666 glucagon Drugs 0.000 claims description 14
238000000034 method Methods 0.000 claims description 11
108090000765 processed proteins & peptides Proteins 0.000 claims description 10
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 4
150000001718 carbodiimides Chemical class 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 71
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 65
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 26
229960000583 acetic acid Drugs 0.000 description 25
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
239000000047 product Substances 0.000 description 16
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 12
239000012362 glacial acetic acid Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
229940024606 amino acid Drugs 0.000 description 9
150000001413 amino acids Chemical class 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000009833 condensation Methods 0.000 description 8
230000005494 condensation Effects 0.000 description 8
239000000052 vinegar Substances 0.000 description 8
235000021419 vinegar Nutrition 0.000 description 8
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
210000000496 pancreas Anatomy 0.000 description 4
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
102000007079 Peptide Fragments Human genes 0.000 description 2
108010033276 Peptide Fragments Proteins 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000012634 fragment Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 description 1
TXDGEONUWGOCJG-LBPRGKRZSA-N (2s)-3-[(2-methylpropan-2-yl)oxy]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound CC(C)(C)OC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 TXDGEONUWGOCJG-LBPRGKRZSA-N 0.000 description 1
NMJINEMBBQVPGY-RITPCOANSA-N (2s,3r)-2-azaniumyl-3-[(2-methylpropan-2-yl)oxy]butanoate Chemical compound CC(C)(C)O[C@H](C)[C@H]([NH3+])C([O-])=O NMJINEMBBQVPGY-RITPCOANSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
230000001174 ascending effect Effects 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000029087 digestion Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003517 fume Substances 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
-1 hydroxysuccinic acid imide Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000492 insulin antagonist Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
DVCSNHXRZUVYAM-BQBZGAKWSA-N leu-asp Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC(O)=O DVCSNHXRZUVYAM-BQBZGAKWSA-N 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
GZYHNIHHRYGVCV-UHFFFAOYSA-M potassium;hydrogen carbonate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [K+].OC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O GZYHNIHHRYGVCV-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001665 trituration 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
- C07K14/575—Hormones
- C07K14/605—Glucagons

Landscapes

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

NO3099/68A 1967-08-19 1968-08-07 NO122483B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0053291		1967-08-19

Publications (1)

Publication Number	Publication Date
NO122483B true NO122483B (de)	1971-07-05

Family

ID=7106172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3099/68A NO122483B (de)	1967-08-19	1968-08-07

Country Status (8)

Country	Link
US (1)	US3642763A (de)
AT (1)	AT285834B (de)
CH (1)	CH500167A (de)
DE (1)	DE1643345C3 (de)
DK (1)	DK124749B (de)
NL (1)	NL6811541A (de)
NO (1)	NO122483B (de)
SE (2)	SE376606B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3897551A (en) *	1971-04-05	1975-07-29	Lilly Co Eli	Iodoglucagons and process for prolonging the biological activity of glucagon
US4206199A (en) *	1977-07-22	1980-06-03	Takeda Chemical Industries, Ltd.	Novel glucagon fragment and its derivatives
JPS5657753A (en) *	1979-10-16	1981-05-20	Toyo Jozo Co Ltd	Novel glucagon fragment, and its use
DK283180A (da) *	1980-07-01	1982-01-02	Novo Industri As	Polypeptider og derivater deraf
US4423034A (en) *	1980-10-16	1983-12-27	Toyo Jozo Kabushiki Kaisha	Process for the preparation of antibodies
WO1983002271A1 (en) *	1981-12-28	1983-07-07	Novo Industri As	Use of peptides as a medicament
US4879273A (en) *	1987-05-22	1989-11-07	The Rockefeller University	Glucagon homologs and therapeutic use thereof
EP3864032B1 (de)	2018-10-09	2022-11-30	Fresenius Kabi iPSUM S.r.l.	Verfahren zur herstellung von glp-1-analoga
US20220324936A1 (en) *	2019-06-18	2022-10-13	Fresenius Kabi Ipsum S.R.L.	Process for the manufacture of glucagon
EP3753946A1 (de)	2019-06-18	2020-12-23	Fresenius Kabi iPSUM S.r.l.	Verbessertes verfahren zur herstellung von hochreinem glucagon
JP2026502671A (ja) *	2023-01-27	2026-01-23	バイオコン・リミテッド	グルカゴンの製造方法

1967
- 1967-08-19 DE DE1643345A patent/DE1643345C3/de not_active Expired
1968
- 1968-08-07 NO NO3099/68A patent/NO122483B/no unknown
- 1968-08-13 US US752129A patent/US3642763A/en not_active Expired - Lifetime
- 1968-08-14 NL NL6811541A patent/NL6811541A/xx unknown
- 1968-08-15 CH CH1225168A patent/CH500167A/de not_active IP Right Cessation
- 1968-08-16 DK DK399368AA patent/DK124749B/da unknown
- 1968-08-16 AT AT802468A patent/AT285834B/de not_active IP Right Cessation
- 1968-08-19 SE SE7113516A patent/SE376606B/xx unknown
- 1968-08-19 SE SE11133/68A patent/SE356294B/xx unknown

Also Published As

Publication number	Publication date
SE376606B (de)	1975-06-02
DE1643345C3 (de)	1975-09-25
AT285834B (de)	1970-11-10
SE356294B (de)	1973-05-21
NL6811541A (de)	1969-02-21
DK124749B (da)	1972-11-20
DE1643345A1 (de)	1971-06-24
CH500167A (de)	1970-12-15
DE1643345B2 (de)	1975-02-13
US3642763A (en)	1972-02-15

Publication	Publication Date	Title
US4395403A (en)	1983-07-26	Polypeptides, processes for their production, pharmaceutical compositions comprising said polypeptides and their use
US4435385A (en)	1984-03-06	N-Acyl-polypeptides and processes for the production thereof
US3705140A (en)	1972-12-05	Peptides related to the c-terminal sequence of cck-pz and caerulein
US3642763A (en)	1972-02-15	Protected glucagon and its hydrobromide salts
DE2315271B2 (de)	1975-01-30	L- Norleucin-13-Motllln, Verfahren zu dessen Herstellung und dasselbe enthaltendes Mittel
HU181843B (en)	1983-11-28	Process for producing acth derivatives of psichopharmacological activity
US3749703A (en)	1973-07-31	Asn15-bovine thyrocalcitonin
DE1935402A1 (de)	1970-01-22	Neue sulfonierte Peptide
US3299035A (en)	1967-01-17	L-aspartyl-l-alanyl-l-phenylalanyl-l-isoleucyl-glycyl-l-leucyl-l-methioninamide and its acid addition salts
FR2567524A1 (fr)	1986-01-17	Procede de synthese de la somatocrinine en phase liquide et peptides intermediaires
FR2557114A1 (fr)	1985-06-28	Nouveaux derives de la gonadoliberine, procede pour leur preparation et compositions pharmaceutiques les contenant
NO120478B (de)	1970-10-26
US3770715A (en)	1973-11-06	Acth active peptides having d serine as first aminoacid from n terminus and l ornithine as11 aminoacid
NO860752L (no)	1986-12-29	Pentapeptider med cellevekstregulerende virkning og fremgangsmaate for fremstilling derav.
CH658661A5 (de)	1986-11-28	Peptidverbindungen.
JPS59141549A (ja)	1984-08-14	ソマトスタチン作用を有する環状ペプチド
DE2327396A1 (de)	1973-12-13	Synthetisches polypeptid und verfahren zur herstellung desselben
US3247180A (en)	1966-04-19	Nonadecapeptides and intermediates for the preparation thereof
US4271152A (en)	1981-06-02	Psycho-pharmacological peptides
HU180787B (en)	1983-04-29	Process for preparing peptides containing cysteine
US3300468A (en)	1967-01-24	Octadecapeptides and intermediates in the preparation thereof
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DE2050434A1 (de)	1971-05-06	Neue Peptide und Verfahren zu ihrer Herstellung
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