ZA200100370B - Processes for coupling amino acids using Bis-Trichloromethyl) carbonate. - Google Patents
Processes for coupling amino acids using Bis-Trichloromethyl) carbonate. Download PDFInfo
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- ZA200100370B ZA200100370B ZA200100370A ZA200100370A ZA200100370B ZA 200100370 B ZA200100370 B ZA 200100370B ZA 200100370 A ZA200100370 A ZA 200100370A ZA 200100370 A ZA200100370 A ZA 200100370A ZA 200100370 B ZA200100370 B ZA 200100370B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino acid
- peptide
- coupling
- ala
- blocked
- Prior art date
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- 238000010168 coupling process Methods 0.000 title claims description 115
- 238000005859 coupling reaction Methods 0.000 title claims description 115
- 230000008878 coupling Effects 0.000 title claims description 114
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title 1
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- 238000006243 chemical reaction Methods 0.000 claims description 38
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- 239000002253 acid Substances 0.000 claims description 21
- 125000001151 peptidyl group Chemical group 0.000 claims description 21
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- 239000002904 solvent Substances 0.000 claims description 19
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
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- 150000001875 compounds Chemical class 0.000 claims description 7
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- 210000004357 third molar Anatomy 0.000 claims 1
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- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- MGHMWKZOLAAOTD-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NC(C(=O)O)CC1=CNC2=CC=CC=C12 MGHMWKZOLAAOTD-UHFFFAOYSA-N 0.000 description 1
- WTOFYLAWDLQMBZ-UHFFFAOYSA-N 2-azaniumyl-3-thiophen-2-ylpropanoate Chemical compound OC(=O)C(N)CC1=CC=CS1 WTOFYLAWDLQMBZ-UHFFFAOYSA-N 0.000 description 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
- GSWYUZQBLVUEPH-UHFFFAOYSA-N 3-(azaniumylmethyl)benzoate Chemical compound NCC1=CC=CC(C(O)=O)=C1 GSWYUZQBLVUEPH-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- CMUHFUGDYMFHEI-QMMMGPOBSA-N 4-amino-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N)C=C1 CMUHFUGDYMFHEI-QMMMGPOBSA-N 0.000 description 1
- ZZOKVYOCRSMTSS-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl carbamate Chemical class C1=CC=C2C(COC(=O)N)C3=CC=CC=C3C2=C1 ZZOKVYOCRSMTSS-UHFFFAOYSA-N 0.000 description 1
- TYMIFYJJOPYXBG-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl piperidine-1-carboxylate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N1CCCCC1 TYMIFYJJOPYXBG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000998969 Homo sapiens Inositol-3-phosphate synthase 1 Proteins 0.000 description 1
- 102100036881 Inositol-3-phosphate synthase 1 Human genes 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 description 1
- GLUBLISJVJFHQS-VIFPVBQESA-N Phe-Gly Chemical compound OC(=O)CNC(=O)[C@@H](N)CC1=CC=CC=C1 GLUBLISJVJFHQS-VIFPVBQESA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 241000201776 Steno Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- POORJMIIHXHXAV-SOYHJAILSA-N [(3ar,5r,5as,8as,8br)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydro-3ah-di[1,3]dioxolo[4,5-a:5',4'-d]pyran-5-yl]methanol Chemical compound O1[C@H](CO)[C@@H]2OC(C)(C)O[C@@H]2[C@H]2OC(C)(C)O[C@H]21 POORJMIIHXHXAV-SOYHJAILSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- DLAMVQGYEVKIRE-UHFFFAOYSA-N alpha-(methylamino)isobutyric acid Chemical compound CNC(C)(C)C(O)=O DLAMVQGYEVKIRE-UHFFFAOYSA-N 0.000 description 1
- AYJPQGDWEDBSTK-UHFFFAOYSA-N amino-(2-amino-2-oxoethyl)carbamic acid Chemical group OC(=O)N(N)CC(N)=O AYJPQGDWEDBSTK-UHFFFAOYSA-N 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000002256 galaktoses Chemical class 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000007335 nucleophilic acyl substitution reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 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
- 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
- C07K1/06—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- 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
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- 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
- C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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
- C07K5/1019—Tetrapeptides with the first amino acid being basic
-
- 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)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12531498A IL125314A (en) | 1998-07-12 | 1998-07-12 | Processes for attaching amino acids using a bite - (trichloromethyl) carbonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200100370B true ZA200100370B (en) | 2001-07-26 |
Family
ID=11071733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200100370A ZA200100370B (en) | 1998-07-12 | 2001-01-12 | Processes for coupling amino acids using Bis-Trichloromethyl) carbonate. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6512092B2 (cs) |
| EP (1) | EP1097164A4 (cs) |
| JP (1) | JP2002520331A (cs) |
| KR (1) | KR20010071853A (cs) |
| CN (1) | CN1317011A (cs) |
| AU (1) | AU754560B2 (cs) |
| CA (1) | CA2334076A1 (cs) |
| CZ (1) | CZ296014B6 (cs) |
| HU (1) | HUP0102884A3 (cs) |
| IL (1) | IL125314A (cs) |
| NZ (1) | NZ509304A (cs) |
| PL (1) | PL345532A1 (cs) |
| WO (1) | WO2000002898A1 (cs) |
| ZA (1) | ZA200100370B (cs) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040091451A1 (en) * | 2000-05-29 | 2004-05-13 | Marie-Therese Charreyre | Biocompatible polymer for fixing biological ligands |
| EP1373190A2 (de) | 2001-03-28 | 2004-01-02 | Bayer Chemicals AG | Verfahren zur herstellung von carbonsäureamiden |
| US7205385B2 (en) * | 2004-11-12 | 2007-04-17 | General Electric Company | Polymerization method for the synthesis of polypeptide imaging agents |
| CN101203527A (zh) * | 2005-05-31 | 2008-06-18 | 耶路撒冷希伯来大学伊森姆研究发展公司 | 主链环化的促黑皮质素激素（αMSH）类似物 |
| FI20055653L (fi) * | 2005-12-08 | 2007-06-09 | Wallac Oy | Leimausreagenssi |
| KR100831858B1 (ko) | 2006-05-23 | 2008-05-22 | 한기종 | 새로운 펩타이드결합 생성방법 |
| GB2472563B (en) * | 2009-04-28 | 2013-02-27 | Univ Leicester | Method of preparing hairpin and cyclic polyamides |
| WO2011024175A1 (en) | 2009-08-28 | 2011-03-03 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Macrocyclic compounds, compositions comprising them and methods for preventing or treating hiv infection |
| WO2013111129A1 (en) | 2012-01-23 | 2013-08-01 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Stabilized peptide helices for inhibiting dimerization of chemokine c motif receptor 2 (ccr2) |
| WO2015087334A1 (en) | 2013-12-15 | 2015-06-18 | Yissum Research Develoment Company Of The Hebrew University Of Jerusalem Ltd. | Viperistatin-derived peptides and uses thereof |
| US10662225B2 (en) | 2016-06-07 | 2020-05-26 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Backbone cyclized inhibitory peptides of myeloid differentiation factor 88 (MyD88) |
| KR20250007021A (ko) | 2017-06-09 | 2025-01-13 | 추가이 세이야쿠 가부시키가이샤 | N-치환 아미노산을 포함하는 펩타이드의 합성 방법 |
| EP3684794B1 (en) | 2017-09-19 | 2025-08-06 | Yissum Research and Development Company of the Hebrew University of Jerusalem Ltd. | Somatostatin prodrugs |
| WO2019197466A1 (en) * | 2018-04-10 | 2019-10-17 | Sanofi-Aventis Deutschland Gmbh | Method for cleavage of solid phase-bound peptides from the solid phase |
| CN110818771B (zh) * | 2018-08-14 | 2023-01-17 | 陈铭 | 使用氨基酸离子液体的羰基硫介导多肽合成 |
| KR20210098476A (ko) | 2018-11-30 | 2021-08-10 | 추가이 세이야쿠 가부시키가이샤 | 펩티드 화합물 또는 아마이드 화합물의 탈보호법 및 고상 반응에 있어서의 탈수지 방법, 및 펩티드 화합물의 제조 방법 |
| EP3927737A1 (en) | 2019-02-21 | 2021-12-29 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Par4 derived peptides, analogs and uses thereof |
| WO2022003673A1 (en) | 2020-06-30 | 2022-01-06 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Humanin analogs and uses thereof |
| CN114047269B (zh) * | 2022-01-13 | 2022-04-15 | 浙江湃肽生物有限公司南京分公司 | 一种乙酰基六肽-8的检测方法 |
| WO2025141573A1 (en) | 2023-12-27 | 2025-07-03 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Calreticulin peptidomimetic inhibitors and prodrugs |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3440141A1 (de) * | 1984-11-02 | 1986-05-07 | Heiner Dipl.-Chem. Dr. 8000 München Eckert | Verwendung von kohlensaeure-bis-trichlormethylester als proreagens fuer phosgen |
| TW304957B (cs) | 1991-06-18 | 1997-05-11 | Lilly Co Eli | |
| US5198548A (en) * | 1992-01-30 | 1993-03-30 | Warner-Lambert Company | Process for the preparation of D(-) and L(+)-3,3-diphenylalanine and D(-) and L(+)-substituted 3,3-diphenylalanines and derivatives thereof |
-
1998
- 1998-07-12 IL IL12531498A patent/IL125314A/en not_active IP Right Cessation
-
1999
- 1999-07-11 CN CN99810807A patent/CN1317011A/zh active Pending
- 1999-07-11 WO PCT/IL1999/000378 patent/WO2000002898A1/en not_active Application Discontinuation
- 1999-07-11 CZ CZ2001159A patent/CZ296014B6/cs not_active IP Right Cessation
- 1999-07-11 NZ NZ509304A patent/NZ509304A/xx unknown
- 1999-07-11 AU AU46454/99A patent/AU754560B2/en not_active Ceased
- 1999-07-11 KR KR1020017000457A patent/KR20010071853A/ko not_active Ceased
- 1999-07-11 JP JP2000559127A patent/JP2002520331A/ja active Pending
- 1999-07-11 CA CA002334076A patent/CA2334076A1/en not_active Abandoned
- 1999-07-11 HU HU0102884A patent/HUP0102884A3/hu unknown
- 1999-07-11 PL PL99345532A patent/PL345532A1/xx not_active Application Discontinuation
- 1999-07-11 EP EP99929678A patent/EP1097164A4/en not_active Withdrawn
-
2001
- 2001-01-09 US US09/756,223 patent/US6512092B2/en not_active Expired - Fee Related
- 2001-01-12 ZA ZA200100370A patent/ZA200100370B/en unknown
-
2002
- 2002-12-18 US US10/321,648 patent/US7045592B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002520331A (ja) | 2002-07-09 |
| EP1097164A1 (en) | 2001-05-09 |
| US6512092B2 (en) | 2003-01-28 |
| WO2000002898A1 (en) | 2000-01-20 |
| AU754560B2 (en) | 2002-11-21 |
| AU4645499A (en) | 2000-02-01 |
| NZ509304A (en) | 2003-01-31 |
| EP1097164A4 (en) | 2005-05-25 |
| CZ296014B6 (cs) | 2005-12-14 |
| IL125314A (en) | 2004-07-25 |
| CZ2001159A3 (cs) | 2001-09-12 |
| IL125314A0 (en) | 1999-03-12 |
| CN1317011A (zh) | 2001-10-10 |
| HUP0102884A3 (en) | 2002-02-28 |
| HUP0102884A2 (hu) | 2002-01-28 |
| US7045592B2 (en) | 2006-05-16 |
| KR20010071853A (ko) | 2001-07-31 |
| US20010007037A1 (en) | 2001-07-05 |
| US20030195331A1 (en) | 2003-10-16 |
| CA2334076A1 (en) | 2000-01-20 |
| PL345532A1 (en) | 2001-12-17 |
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