CA2593866C - Synthesis of peptide t-1249 using peptide intermediate fragments - Google Patents
Synthesis of peptide t-1249 using peptide intermediate fragments Download PDFInfo
- Publication number
- CA2593866C CA2593866C CA2593866A CA2593866A CA2593866C CA 2593866 C CA2593866 C CA 2593866C CA 2593866 A CA2593866 A CA 2593866A CA 2593866 A CA2593866 A CA 2593866A CA 2593866 C CA2593866 C CA 2593866C
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- Prior art keywords
- peptide
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- nmp
- reactor
- seq
- Prior art date
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- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZRZKFGDGIPLXIB-UHFFFAOYSA-N fluoroform;sulfuric acid Chemical compound FC(F)F.OS(O)(=O)=O ZRZKFGDGIPLXIB-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000034217 membrane fusion Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 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
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000003809 water extraction 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
- C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16111—Human Immunodeficiency Virus, HIV concerning HIV env
- C12N2740/16122—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64071604P | 2004-12-30 | 2004-12-30 | |
| US60/640,716 | 2004-12-30 | ||
| PCT/EP2005/013854 WO2006069729A1 (en) | 2004-12-30 | 2005-12-22 | Synthesis of peptide t-1249 using peptide intermediate fragments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2593866A1 CA2593866A1 (en) | 2006-07-06 |
| CA2593866C true CA2593866C (en) | 2013-08-06 |
Family
ID=36001047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2593866A Expired - Fee Related CA2593866C (en) | 2004-12-30 | 2005-12-22 | Synthesis of peptide t-1249 using peptide intermediate fragments |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7544665B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1856142B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4886703B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN101133076B (cg-RX-API-DMAC7.html) |
| AT (1) | ATE439371T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2593866C (cg-RX-API-DMAC7.html) |
| DE (1) | DE602005016024D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2329270T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006069729A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007007917A (es) * | 2004-12-30 | 2007-08-14 | Hoffmann La Roche | Sintesis del peptido t-20 utilizando fragmentos peptidicos intermediarios. |
| CA2703113A1 (en) * | 2007-10-27 | 2009-04-30 | F. Hoffmann-La Roche Ag | Insulinotropic peptide synthesis using solid and solution phase combination techniques |
| CA2707132A1 (en) * | 2007-12-11 | 2009-06-18 | F. Hoffmann-La Roche Ag | Insulinotropic peptide synthesis using solid and solution phase combination techniques |
| DE102008017645A1 (de) | 2008-04-04 | 2009-10-08 | Carl Zeiss Smt Ag | Vorrichtung zur mikrolithographischen Projektionsbelichtung sowie Vorrichtung zur Inspektion einer Oberfläche eines Substrats |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4010560B2 (ja) | 1992-07-20 | 2007-11-21 | ドューク ユニバーシティー | Ｈｉｖ複製を阻害する化合物 |
| US6281335B1 (en) | 1993-10-08 | 2001-08-28 | Coulter Corporation | Hybridoma and anti-KC-4 humanized monoclonal antibody |
| US6479055B1 (en) | 1993-06-07 | 2002-11-12 | Trimeris, Inc. | Methods for inhibition of membrane fusion-associated events, including respiratory syncytial virus transmission |
| US5464933A (en) | 1993-06-07 | 1995-11-07 | Duke University | Synthetic peptide inhibitors of HIV transmission |
| US6281331B1 (en) * | 1998-03-23 | 2001-08-28 | Trimeris, Inc. | Methods and compositions for peptide synthesis |
| US6469136B1 (en) * | 1999-07-07 | 2002-10-22 | Trimeris, Inc. | Methods and composition for peptide synthesis |
| US20040209999A1 (en) * | 2002-08-16 | 2004-10-21 | Bohling James Charles | Method of manufacturing polypeptides, including T-20 and T-1249, at commercial scale, and polypeptide compositions related thereto |
| AU2004200485A1 (en) * | 2003-02-25 | 2004-09-09 | Rohm And Haas Company | Method of manufacturing T-20 and T-1249 peptides at commercial scale, and T-20 and T-1249 compositions related thereto |
| MX2007007917A (es) | 2004-12-30 | 2007-08-14 | Hoffmann La Roche | Sintesis del peptido t-20 utilizando fragmentos peptidicos intermediarios. |
-
2005
- 2005-12-22 CA CA2593866A patent/CA2593866C/en not_active Expired - Fee Related
- 2005-12-22 WO PCT/EP2005/013854 patent/WO2006069729A1/en not_active Ceased
- 2005-12-22 JP JP2007548733A patent/JP4886703B2/ja not_active Expired - Fee Related
- 2005-12-22 DE DE602005016024T patent/DE602005016024D1/de not_active Expired - Lifetime
- 2005-12-22 ES ES05821840T patent/ES2329270T3/es not_active Expired - Lifetime
- 2005-12-22 EP EP05821840A patent/EP1856142B1/en not_active Expired - Lifetime
- 2005-12-22 CN CN2005800488419A patent/CN101133076B/zh not_active Expired - Fee Related
- 2005-12-22 AT AT05821840T patent/ATE439371T1/de not_active IP Right Cessation
- 2005-12-30 US US11/322,394 patent/US7544665B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7544665B2 (en) | 2009-06-09 |
| JP2008526699A (ja) | 2008-07-24 |
| CN101133076A (zh) | 2008-02-27 |
| ES2329270T3 (es) | 2009-11-24 |
| CA2593866A1 (en) | 2006-07-06 |
| CN101133076B (zh) | 2011-07-13 |
| US20060173163A1 (en) | 2006-08-03 |
| DE602005016024D1 (de) | 2009-09-24 |
| ATE439371T1 (de) | 2009-08-15 |
| EP1856142A1 (en) | 2007-11-21 |
| WO2006069729A1 (en) | 2006-07-06 |
| JP4886703B2 (ja) | 2012-02-29 |
| EP1856142B1 (en) | 2009-08-12 |
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| EP1701969B1 (en) | Process for peptide synthesis using a reduced amount of deprotection agent | |
| WO2005063799A2 (en) | Peptide synthesis and deprotection with co-solvent | |
| CA2593866C (en) | Synthesis of peptide t-1249 using peptide intermediate fragments | |
| CA2592438C (en) | Synthesis of peptide t-20 using peptide intermediate fragments | |
| EP1701972B1 (en) | Process and systems for recovery of peptides | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20171222 |