NO326377B1 - Fremgangsmate for fremstilling av forbindelser - Google Patents
Fremgangsmate for fremstilling av forbindelser Download PDFInfo
- Publication number
- NO326377B1 NO326377B1 NO20023445A NO20023445A NO326377B1 NO 326377 B1 NO326377 B1 NO 326377B1 NO 20023445 A NO20023445 A NO 20023445A NO 20023445 A NO20023445 A NO 20023445A NO 326377 B1 NO326377 B1 NO 326377B1
- Authority
- NO
- Norway
- Prior art keywords
- amine
- anion
- protecting group
- groups
- cleaning agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 22
- 150000001450 anions Chemical class 0.000 claims description 20
- 239000012459 cleaning agent Substances 0.000 claims description 16
- 238000010511 deprotection reaction Methods 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 150000003141 primary amines Chemical group 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
- 239000011780 sodium chloride Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 13
- -1 (substituted) benzyl Chemical group 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 238000000605 extraction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 108010038807 Oligopeptides Proteins 0.000 description 5
- 102000015636 Oligopeptides Human genes 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- USPFMEKVPDBMCG-LBPRGKRZSA-N N-benzyloxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 USPFMEKVPDBMCG-LBPRGKRZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- 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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202751 | 2001-07-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023445D0 NO20023445D0 (no) | 2002-07-18 |
| NO20023445L NO20023445L (no) | 2003-01-20 |
| NO326377B1 true NO326377B1 (no) | 2008-11-17 |
Family
ID=8180655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023445A NO326377B1 (no) | 2001-07-19 | 2002-07-18 | Fremgangsmate for fremstilling av forbindelser |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US6864357B2 (es) |
| EP (1) | EP1277761B1 (es) |
| JP (1) | JP3579038B2 (es) |
| KR (1) | KR100869520B1 (es) |
| CN (1) | CN1254482C (es) |
| AR (1) | AR035258A1 (es) |
| AT (1) | ATE531724T1 (es) |
| AU (1) | AU2002300166C1 (es) |
| BR (1) | BRPI0202779B1 (es) |
| CA (1) | CA2394216C (es) |
| DK (1) | DK1277761T3 (es) |
| EC (1) | ECSP024292A (es) |
| ES (1) | ES2374389T3 (es) |
| HK (1) | HK1050905A1 (es) |
| HR (1) | HRP20020608A2 (es) |
| HU (1) | HUP0202370A2 (es) |
| IL (1) | IL150600A (es) |
| MX (1) | MXPA02006997A (es) |
| NO (1) | NO326377B1 (es) |
| PE (1) | PE20030215A1 (es) |
| PL (1) | PL355126A1 (es) |
| RU (1) | RU2242457C2 (es) |
| SG (1) | SG120874A1 (es) |
| TW (1) | TWI243826B (es) |
| ZA (1) | ZA200205408B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI247012B (en) * | 2001-07-19 | 2006-01-11 | Akzo Nobel Nv | Process for rapid solution synthesis of peptides |
| US7393277B2 (en) * | 2003-08-25 | 2008-07-01 | Igt | Horseshoe payline system and games using that system |
| EP1790656A1 (en) | 2005-11-25 | 2007-05-30 | Nanokem S.A. | Solution-phase synthesis of leuprolide |
| ATE461208T1 (de) * | 2006-01-17 | 2010-04-15 | Organon Nv | Selektive enzymatische hydrolyse von c-terminalen tert-butyl-peptidestern |
| JP4684124B2 (ja) * | 2006-02-16 | 2011-05-18 | 富士通株式会社 | 移動局装置及び同装置における送信電力制御方法 |
| ES2729197T3 (es) | 2006-03-01 | 2019-10-30 | Kaneka Corp | Método de producción de péptidos |
| US7601062B2 (en) * | 2006-11-06 | 2009-10-13 | Igt | Gaming device and method including moving paylines |
| US8124372B2 (en) * | 2007-06-25 | 2012-02-28 | N.V. Organon | Selective enzymatic amidation of C-terminal esters or acids of peptides |
| EP2755690B1 (en) | 2011-08-04 | 2020-04-01 | Merck Sharp & Dohme B.V. | Kisspeptide-pentasaccharide conjugates |
| US9177447B2 (en) | 2012-09-25 | 2015-11-03 | Igt | Gaming system and method for providing a symbol matrix with a moveable symbol display window |
| PT2907809T (pt) * | 2014-02-14 | 2019-01-16 | Corden Pharma Int Gmbh | Processo sem base para a preparação de intermediários de cetona utilizáveis para fabrico de nebivolol |
| CN115362144A (zh) * | 2020-03-27 | 2022-11-18 | 株式会社钟化 | 含酰胺键化合物的制造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5221754A (en) * | 1989-06-09 | 1993-06-22 | Research Corporation Technologies, Inc. | Reagents for rapid peptide synthesis |
| US5101059A (en) * | 1989-12-05 | 1992-03-31 | Research Corporation Technologies, Inc. | Amino acid protecting groups |
| US5516892A (en) * | 1992-12-28 | 1996-05-14 | Indiana University Foundation | Polymer-bound mixed carboxylic anhdrides as a stable form of activated carboxylic acids |
| US6310180B1 (en) * | 1993-06-21 | 2001-10-30 | Vanderbilt University | Method for synthesis of proteins |
| US5516639A (en) * | 1993-07-22 | 1996-05-14 | Mayo Foundation For Medical Education And Research | Antibodies specific for human prostate glandular kallkrein |
| US5849954A (en) * | 1996-01-18 | 1998-12-15 | Research Corporation Technologies, Inc. | Method of peptide synthesis |
| NZ332116A (en) * | 1996-05-03 | 2000-06-23 | Warner Lambert Co | Rapid purification of synthetic intermediates and products by polymer supported quench reagents |
| US6121488A (en) * | 1997-09-24 | 2000-09-19 | Warner-Lambert Company | Quenching reagents for solution phase synthesis |
| JPH11217397A (ja) * | 1997-11-27 | 1999-08-10 | Saburo Aimoto | ペプチドチオールエステルの製造方法 |
| FR2780061B1 (fr) * | 1998-06-22 | 2001-09-07 | Rhone Poulenc Rorer Sa | Nouveau procede de preparation de derives de cyclosporine |
| WO2000071567A2 (en) * | 1999-05-06 | 2000-11-30 | Human Genome Sciences, Inc. | Fibroblast growth factor 13 |
| MXPA01012082A (es) * | 1999-05-26 | 2002-07-22 | Abbott Lab | Proceso de sintesis de peptidos de aislamiento minimo, usando resinas de intercambio de iones como agentes depuradores. |
| US20020127219A1 (en) * | 1999-12-30 | 2002-09-12 | Okkels Jens Sigurd | Lysosomal enzymes and lysosomal enzyme activators |
| DE60134230D1 (de) * | 2000-07-19 | 2008-07-10 | Pharmacia & Upjohn Co Llc | Substraten und nachweise zur wirksamkeit von beta-secretase |
-
2002
- 2002-07-04 IL IL15060002A patent/IL150600A/xx unknown
- 2002-07-04 TW TW091114833A patent/TWI243826B/zh active
- 2002-07-05 ZA ZA200205408A patent/ZA200205408B/xx unknown
- 2002-07-05 JP JP2002197549A patent/JP3579038B2/ja not_active Expired - Lifetime
- 2002-07-15 SG SG200204299A patent/SG120874A1/en unknown
- 2002-07-15 DK DK02077875.9T patent/DK1277761T3/da active
- 2002-07-15 ES ES02077875T patent/ES2374389T3/es not_active Expired - Lifetime
- 2002-07-15 AT AT02077875T patent/ATE531724T1/de active
- 2002-07-15 EP EP02077875A patent/EP1277761B1/en not_active Expired - Lifetime
- 2002-07-17 MX MXPA02006997A patent/MXPA02006997A/es active IP Right Grant
- 2002-07-18 CA CA002394216A patent/CA2394216C/en not_active Expired - Lifetime
- 2002-07-18 HU HU0202370A patent/HUP0202370A2/hu unknown
- 2002-07-18 NO NO20023445A patent/NO326377B1/no not_active IP Right Cessation
- 2002-07-18 BR BRPI0202779A patent/BRPI0202779B1/pt active IP Right Grant
- 2002-07-18 AR ARP020102686A patent/AR035258A1/es active IP Right Grant
- 2002-07-18 CN CNB021261903A patent/CN1254482C/zh not_active Expired - Lifetime
- 2002-07-18 AU AU2002300166A patent/AU2002300166C1/en not_active Expired
- 2002-07-18 RU RU2002119631/04A patent/RU2242457C2/ru not_active IP Right Cessation
- 2002-07-18 KR KR1020020041897A patent/KR100869520B1/ko not_active IP Right Cessation
- 2002-07-18 PE PE2002000640A patent/PE20030215A1/es not_active Application Discontinuation
- 2002-07-19 PL PL02355126A patent/PL355126A1/xx not_active IP Right Cessation
- 2002-07-19 HR HR20020608A patent/HRP20020608A2/hr not_active Application Discontinuation
- 2002-07-19 EC EC2002004292A patent/ECSP024292A/es unknown
- 2002-07-19 US US10/199,785 patent/US6864357B2/en not_active Expired - Lifetime
-
2003
- 2003-04-29 HK HK03103038.5A patent/HK1050905A1/xx not_active IP Right Cessation
-
2004
- 2004-12-14 US US11/012,439 patent/US20050101764A1/en not_active Abandoned
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
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