NO133590B - - Google Patents
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- Publication number
- NO133590B NO133590B NO440/71A NO44071A NO133590B NO 133590 B NO133590 B NO 133590B NO 440/71 A NO440/71 A NO 440/71A NO 44071 A NO44071 A NO 44071A NO 133590 B NO133590 B NO 133590B
- Authority
- NO
- Norway
- Prior art keywords
- insulin
- phenylalanine
- des
- acid
- tert
- Prior art date
Links
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Substances N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 30
- 229940125396 insulin Drugs 0.000 claims description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 102000004877 Insulin Human genes 0.000 claims description 11
- 108090001061 Insulin Proteins 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- -1 butyloxycarbonyl azide Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 3
- 239000012062 aqueous buffer Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 108010005991 Pork Regular Insulin Proteins 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 101001011741 Bos taurus Insulin Proteins 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- IXIBAKNTJSCKJM-BUBXBXGNSA-N bovine insulin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 IXIBAKNTJSCKJM-BUBXBXGNSA-N 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000001962 electrophoresis Methods 0.000 description 2
- 239000004026 insulin derivative Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JOMYOCCEANTNON-UHFFFAOYSA-N (4-nitrophenyl)carbamothioic s-acid Chemical compound [O-][N+](=O)C1=CC=C(NC(S)=O)C=C1 JOMYOCCEANTNON-UHFFFAOYSA-N 0.000 description 1
- MZZVFXMTZTVUFO-UHFFFAOYSA-N 1-chloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1 MZZVFXMTZTVUFO-UHFFFAOYSA-N 0.000 description 1
- GFEPANUKFYVALF-UHFFFAOYSA-N 1-isothiocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=S)=C1 GFEPANUKFYVALF-UHFFFAOYSA-N 0.000 description 1
- NXHSSIGRWJENBH-UHFFFAOYSA-N 1-isothiocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=S)C=C1 NXHSSIGRWJENBH-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- LGUHADBEXWHGIZ-UHFFFAOYSA-N butyl n-diazocarbamate Chemical compound CCCCOC(=O)N=[N+]=[N-] LGUHADBEXWHGIZ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000007306 turnover Effects 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
- C07K14/62—Insulins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Endocrinology (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Diabetes (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702005658 DE2005658C (de) | 1970-02-07 | Verfahren zur Herstellung von Des-Phenylalanin hoch B 1-Insulin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133590B true NO133590B (da) | 1976-02-16 |
| NO133590C NO133590C (da) | 1976-05-26 |
Family
ID=5761705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO440/71A NO133590C (da) | 1970-02-07 | 1971-02-05 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3801564A (da) |
| JP (1) | JPS5136276B1 (da) |
| AT (1) | AT308293B (da) |
| BE (1) | BE762575A (da) |
| BG (1) | BG17979A3 (da) |
| CA (1) | CA945143A (da) |
| CH (1) | CH569700A5 (da) |
| CS (1) | CS155966B2 (da) |
| DK (1) | DK139577C (da) |
| EG (1) | EG10440A (da) |
| ES (1) | ES387934A1 (da) |
| FI (1) | FI53304C (da) |
| FR (1) | FR2104735B1 (da) |
| GB (1) | GB1340924A (da) |
| IE (1) | IE34934B1 (da) |
| IL (1) | IL36124A (da) |
| NL (1) | NL168502C (da) |
| NO (1) | NO133590C (da) |
| PL (1) | PL81164B1 (da) |
| RO (1) | RO58860A (da) |
| SE (1) | SE370935B (da) |
| SU (1) | SU385436A3 (da) |
| YU (1) | YU34786B (da) |
| ZA (1) | ZA71673B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2256215C3 (de) * | 1972-11-16 | 1981-01-08 | Hoechst Ag, 6000 Frankfurt | Insulin-Zubereitung mit einem Gehalt an kristallinem Insulin und amorphem Desphenylalanin8' -insulin |
| DE3333640A1 (de) * | 1983-09-17 | 1985-04-25 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von insulin-derivaten, deren b-kette c-terminal verlaengert ist, neue basisch modifizierte insulin-derivate diese enthaltende mittel und ihre verwendung |
-
1971
- 1971-02-01 EG EG49/71A patent/EG10440A/xx active
- 1971-02-02 IL IL36124A patent/IL36124A/xx unknown
- 1971-02-02 NL NLAANVRAGE7101360,A patent/NL168502C/xx not_active IP Right Cessation
- 1971-02-03 ZA ZA710673A patent/ZA71673B/xx unknown
- 1971-02-03 SU SU1619741A patent/SU385436A3/ru active
- 1971-02-04 CH CH166371A patent/CH569700A5/xx not_active IP Right Cessation
- 1971-02-04 ES ES387934A patent/ES387934A1/es not_active Expired
- 1971-02-04 YU YU256/71A patent/YU34786B/xx unknown
- 1971-02-05 SE SE7101434A patent/SE370935B/xx unknown
- 1971-02-05 AT AT99271A patent/AT308293B/de not_active IP Right Cessation
- 1971-02-05 FR FR7103898A patent/FR2104735B1/fr not_active Expired
- 1971-02-05 NO NO440/71A patent/NO133590C/no unknown
- 1971-02-05 FI FI310/71A patent/FI53304C/fi active
- 1971-02-05 BE BE762575A patent/BE762575A/xx not_active IP Right Cessation
- 1971-02-05 IE IE137/71A patent/IE34934B1/xx unknown
- 1971-02-05 CA CA104,546A patent/CA945143A/en not_active Expired
- 1971-02-05 US US00113097A patent/US3801564A/en not_active Expired - Lifetime
- 1971-02-05 CS CS87271*#A patent/CS155966B2/cs unknown
- 1971-02-05 DK DK53071A patent/DK139577C/da active
- 1971-02-06 BG BG16760A patent/BG17979A3/xx unknown
- 1971-02-06 PL PL1971146070A patent/PL81164B1/pl unknown
- 1971-02-08 JP JP46005174A patent/JPS5136276B1/ja active Pending
- 1971-02-08 RO RO65848A patent/RO58860A/ro unknown
- 1971-04-19 GB GB2126071A patent/GB1340924A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE762575A (fr) | 1971-08-05 |
| JPS5136276B1 (da) | 1976-10-07 |
| IE34934L (en) | 1971-08-07 |
| DE2005658A1 (de) | 1971-09-02 |
| ZA71673B (en) | 1971-10-27 |
| PL81164B1 (da) | 1975-08-30 |
| DK139577B (da) | 1979-03-12 |
| GB1340924A (en) | 1973-12-19 |
| BG17979A3 (da) | 1974-03-05 |
| CH569700A5 (da) | 1975-11-28 |
| IL36124A0 (en) | 1971-04-28 |
| NL168502C (nl) | 1982-04-16 |
| FI53304C (fi) | 1978-04-10 |
| AT308293B (de) | 1973-06-25 |
| CA945143A (en) | 1974-04-09 |
| CS155966B2 (da) | 1974-06-24 |
| ES387934A1 (es) | 1973-06-01 |
| IL36124A (en) | 1975-02-10 |
| SU385436A3 (da) | 1973-05-29 |
| FI53304B (da) | 1977-12-30 |
| US3801564A (en) | 1974-04-02 |
| DE2005658B2 (de) | 1973-01-11 |
| EG10440A (en) | 1977-09-30 |
| NL168502B (nl) | 1981-11-16 |
| NL7101360A (da) | 1971-08-10 |
| IE34934B1 (en) | 1975-10-01 |
| FR2104735A1 (da) | 1972-04-21 |
| SE370935B (da) | 1974-11-04 |
| YU25671A (en) | 1979-09-10 |
| RO58860A (da) | 1975-10-15 |
| NO133590C (da) | 1976-05-26 |
| FR2104735B1 (da) | 1975-04-18 |
| DK139577C (da) | 1979-09-03 |
| YU34786B (en) | 1980-03-15 |
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