CH615194A5 - Process for the preparation of amidated immunoglobulins - Google Patents
Process for the preparation of amidated immunoglobulins Download PDFInfo
- Publication number
- CH615194A5 CH615194A5 CH1147275A CH1147275A CH615194A5 CH 615194 A5 CH615194 A5 CH 615194A5 CH 1147275 A CH1147275 A CH 1147275A CH 1147275 A CH1147275 A CH 1147275A CH 615194 A5 CH615194 A5 CH 615194A5
- Authority
- CH
- Switzerland
- Prior art keywords
- immunoglobulins
- carbodiimide
- reducing agent
- monoamine
- immunoglobulin
- Prior art date
Links
- 108060003951 Immunoglobulin Proteins 0.000 title claims description 62
- 102000018358 immunoglobulin Human genes 0.000 title claims description 62
- 229940072221 immunoglobulins Drugs 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001718 carbodiimides Chemical class 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 5
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
- 125000004036 acetal group Chemical group 0.000 claims description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229960002442 glucosamine Drugs 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- SJXULIRYGQTEJK-UHFFFAOYSA-N n'-(2-morpholin-4-ylethyl)methanediimine Chemical compound N=C=NCCN1CCOCC1 SJXULIRYGQTEJK-UHFFFAOYSA-N 0.000 claims 1
- 230000000295 complement effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 102000006395 Globulins Human genes 0.000 description 3
- 108010044091 Globulins Proteins 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 206010043376 Tetanus Diseases 0.000 description 2
- -1 aliphatic amines Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 206010013023 diphtheria Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 201000005404 rubella Diseases 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940027941 immunoglobulin g Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442655A DE2442655C3 (de) | 1974-09-06 | 1974-09-06 | Amidierte Immunglobuline und ihre Verwendung zur intravenösen Applikation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615194A5 true CH615194A5 (en) | 1980-01-15 |
Family
ID=5925019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1147275A CH615194A5 (en) | 1974-09-06 | 1975-09-04 | Process for the preparation of amidated immunoglobulins |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5161623A (sv) |
| AR (1) | AR212909A1 (sv) |
| AT (1) | AT342763B (sv) |
| AU (1) | AU499871B2 (sv) |
| BE (1) | BE833186A (sv) |
| BR (1) | BR7505721A (sv) |
| CA (1) | CA1056819A (sv) |
| CH (1) | CH615194A5 (sv) |
| DE (1) | DE2442655C3 (sv) |
| DK (1) | DK399175A (sv) |
| EG (1) | EG11813A (sv) |
| FR (1) | FR2283695A1 (sv) |
| GB (1) | GB1517026A (sv) |
| IE (1) | IE41671B1 (sv) |
| IL (1) | IL48049A (sv) |
| IT (1) | IT1048485B (sv) |
| LU (1) | LU73328A1 (sv) |
| NL (1) | NL7510289A (sv) |
| NZ (1) | NZ178580A (sv) |
| SE (1) | SE403704B (sv) |
| ZA (1) | ZA755687B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004697A (en) * | 1987-08-17 | 1991-04-02 | Univ. Of Ca | Cationized antibodies for delivery through the blood-brain barrier |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3704282A (en) * | 1971-04-09 | 1972-11-28 | Sidney Spector | Catecholamine antigens and antibodies specific therefor |
-
1974
- 1974-09-06 DE DE2442655A patent/DE2442655C3/de not_active Expired
-
1975
- 1975-09-01 NL NL7510289A patent/NL7510289A/xx not_active Application Discontinuation
- 1975-09-04 AU AU84536/75A patent/AU499871B2/en not_active Expired
- 1975-09-04 NZ NZ178580A patent/NZ178580A/xx unknown
- 1975-09-04 GB GB36451/75A patent/GB1517026A/en not_active Expired
- 1975-09-04 IL IL48049A patent/IL48049A/xx unknown
- 1975-09-04 IT IT26918/75A patent/IT1048485B/it active
- 1975-09-04 LU LU73328A patent/LU73328A1/xx unknown
- 1975-09-04 CH CH1147275A patent/CH615194A5/de not_active IP Right Cessation
- 1975-09-05 AT AT689475A patent/AT342763B/de not_active IP Right Cessation
- 1975-09-05 IE IE1944/75A patent/IE41671B1/en unknown
- 1975-09-05 BR BR7505721*A patent/BR7505721A/pt unknown
- 1975-09-05 FR FR7527354A patent/FR2283695A1/fr active Granted
- 1975-09-05 SE SE7509898A patent/SE403704B/sv unknown
- 1975-09-05 CA CA235,134A patent/CA1056819A/en not_active Expired
- 1975-09-05 DK DK399175A patent/DK399175A/da not_active Application Discontinuation
- 1975-09-05 ZA ZA00755687A patent/ZA755687B/xx unknown
- 1975-09-06 EG EG521/75A patent/EG11813A/xx active
- 1975-09-06 JP JP50107581A patent/JPS5161623A/ja active Pending
- 1975-09-08 BE BE159842A patent/BE833186A/xx unknown
- 1975-09-14 AR AR260263A patent/AR212909A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA755687B (en) | 1976-08-25 |
| IE41671L (en) | 1976-03-06 |
| NL7510289A (nl) | 1976-03-09 |
| DE2442655C3 (de) | 1979-09-20 |
| AU8453675A (en) | 1977-03-10 |
| CA1056819A (en) | 1979-06-19 |
| IT1048485B (it) | 1980-11-20 |
| IL48049A0 (en) | 1975-11-25 |
| LU73328A1 (sv) | 1977-05-11 |
| SE7509898L (sv) | 1976-03-08 |
| ATA689475A (de) | 1977-08-15 |
| BE833186A (fr) | 1976-03-08 |
| EG11813A (en) | 1978-09-30 |
| FR2283695B1 (sv) | 1978-09-22 |
| FR2283695A1 (fr) | 1976-04-02 |
| AR212909A1 (es) | 1978-11-15 |
| JPS5161623A (sv) | 1976-05-28 |
| NZ178580A (en) | 1978-03-06 |
| IL48049A (en) | 1978-08-31 |
| SE403704B (sv) | 1978-09-04 |
| BR7505721A (pt) | 1976-08-03 |
| AU499871B2 (en) | 1979-05-03 |
| GB1517026A (en) | 1978-07-05 |
| IE41671B1 (en) | 1980-02-27 |
| AT342763B (de) | 1978-04-25 |
| DE2442655B2 (de) | 1979-02-01 |
| DE2442655A1 (de) | 1976-03-18 |
| DK399175A (da) | 1976-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |