CH624093A5 - Process for the preparation of biologically active polypeptides - Google Patents
Process for the preparation of biologically active polypeptides Download PDFInfo
- Publication number
- CH624093A5 CH624093A5 CH409276A CH409276A CH624093A5 CH 624093 A5 CH624093 A5 CH 624093A5 CH 409276 A CH409276 A CH 409276A CH 409276 A CH409276 A CH 409276A CH 624093 A5 CH624093 A5 CH 624093A5
- Authority
- CH
- Switzerland
- Prior art keywords
- polypeptide
- asp
- ige
- ser
- pro
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 130
- 102000004196 processed proteins & peptides Human genes 0.000 title claims description 80
- 229920001184 polypeptide Polymers 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 19
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- 229920005989 resin Polymers 0.000 claims description 58
- 150000001413 amino acids Chemical class 0.000 claims description 40
- -1 cycloalkyl urethane Chemical compound 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 25
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 210000003630 histaminocyte Anatomy 0.000 claims description 18
- KQDIGHIVUUADBZ-PEDHHIEDSA-N pentigetide Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O KQDIGHIVUUADBZ-PEDHHIEDSA-N 0.000 claims description 18
- 206010020751 Hypersensitivity Diseases 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
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- 150000001408 amides Chemical class 0.000 claims description 13
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- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
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- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
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- 230000001079 digestive effect Effects 0.000 claims 1
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 229960001317 isoprenaline Drugs 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 210000004896 polypeptide structure Anatomy 0.000 claims 1
- 230000002797 proteolythic effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000009121 systemic therapy Methods 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 25
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- 239000000203 mixture Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
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- 238000010511 deprotection reaction Methods 0.000 description 10
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 7
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- 241000700199 Cavia porcellus Species 0.000 description 6
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- 125000003275 alpha amino acid group Chemical group 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
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- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000003549 soybean oil Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
- C07K16/06—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies from serum
- C07K16/065—Purification, fragmentation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1013—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56542575A | 1975-04-04 | 1975-04-04 | |
| DE19762602443 DE2602443A1 (de) | 1975-04-04 | 1976-01-23 | Biologisch aktive polypeptide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624093A5 true CH624093A5 (en) | 1981-07-15 |
Family
ID=25769954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH409276A CH624093A5 (en) | 1975-04-04 | 1976-04-01 | Process for the preparation of biologically active polypeptides |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU514308B2 (show.php) |
| CA (1) | CA1087171A (show.php) |
| CH (1) | CH624093A5 (show.php) |
| FR (1) | FR2305989A1 (show.php) |
| GB (1) | GB1539102A (show.php) |
| MX (1) | MX3790E (show.php) |
| NL (1) | NL7603384A (show.php) |
| SE (1) | SE430058B (show.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2162133T3 (en) * | 2007-07-09 | 2016-10-24 | Nestec Sa | Approaches to reduce allergies caused by environmental allergens |
| US9388236B2 (en) | 2007-07-09 | 2016-07-12 | Nestec Sa | Methods for reducing allergies caused by environmental allergens |
| US11912785B2 (en) | 2017-12-06 | 2024-02-27 | Steven W. Bailey | Peptide compositions for slowing degradation of vitamin mineral supplements, foods, pharmaceutical and cosmetics |
-
1976
- 1976-03-18 MX MX7696U patent/MX3790E/es unknown
- 1976-03-29 GB GB12632/76A patent/GB1539102A/en not_active Expired
- 1976-03-30 FR FR7609232A patent/FR2305989A1/fr active Granted
- 1976-03-30 CA CA249,207A patent/CA1087171A/en not_active Expired
- 1976-04-01 CH CH409276A patent/CH624093A5/de not_active IP Right Cessation
- 1976-04-01 SE SE7603897A patent/SE430058B/xx not_active IP Right Cessation
- 1976-04-01 NL NL7603384A patent/NL7603384A/xx not_active Application Discontinuation
-
1978
- 1978-03-24 AU AU12303/76A patent/AU514308B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU1230376A (en) | 1977-09-29 |
| NL7603384A (nl) | 1976-10-06 |
| MX3790E (es) | 1981-07-20 |
| CA1087171A (en) | 1980-10-07 |
| SE7603897L (sv) | 1976-10-05 |
| FR2305989A1 (fr) | 1976-10-29 |
| AU514308B2 (en) | 1981-02-05 |
| SE430058B (sv) | 1983-10-17 |
| GB1539102A (en) | 1979-01-24 |
| FR2305989B1 (show.php) | 1979-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |