DE69409500T2 - Alkylierung von aminosäuren - Google Patents
Alkylierung von aminosäurenInfo
- Publication number
- DE69409500T2 DE69409500T2 DE69409500T DE69409500T DE69409500T2 DE 69409500 T2 DE69409500 T2 DE 69409500T2 DE 69409500 T DE69409500 T DE 69409500T DE 69409500 T DE69409500 T DE 69409500T DE 69409500 T2 DE69409500 T2 DE 69409500T2
- Authority
- DE
- Germany
- Prior art keywords
- amino acid
- process according
- acid
- reaction
- aspartic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 49
- 238000005804 alkylation reaction Methods 0.000 title description 3
- 230000029936 alkylation Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical group 0.000 claims abstract description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000004064 recycling Methods 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000003862 amino acid derivatives Chemical class 0.000 claims abstract description 4
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 129
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 65
- 229960005261 aspartic acid Drugs 0.000 claims description 65
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 62
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 62
- 229940024606 amino acid Drugs 0.000 claims description 43
- 235000001014 amino acid Nutrition 0.000 claims description 43
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 11
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical group CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- -1 calcium cations Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 150000001576 beta-amino acids Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
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- 239000000047 product Substances 0.000 description 30
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000012452 mother liquor Substances 0.000 description 10
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 9
- 239000000920 calcium hydroxide Substances 0.000 description 9
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 9
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- 238000009835 boiling Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
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- 229960002989 glutamic acid Drugs 0.000 description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- 229960005190 phenylalanine Drugs 0.000 description 5
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 235000011148 calcium chloride Nutrition 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910001622 calcium bromide Inorganic materials 0.000 description 3
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- WTYGAUXICFETTC-UHFFFAOYSA-N cyclobarbital Chemical group C=1CCCCC=1C1(CC)C(=O)NC(=O)NC1=O WTYGAUXICFETTC-UHFFFAOYSA-N 0.000 description 2
- IGBSXRIJNMDLFB-UHFFFAOYSA-N ethane-1,2-diamine;pentanedioic acid Chemical compound NCCN.OC(=O)CCCC(O)=O.OC(=O)CCCC(O)=O IGBSXRIJNMDLFB-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012465 retentate Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- NYPYHUZRZVSYKL-UHFFFAOYSA-N -3,5-Diiodotyrosine Natural products OC(=O)C(N)CC1=CC(I)=C(O)C(I)=C1 NYPYHUZRZVSYKL-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
- COESHZUDRKCEPA-ZETCQYMHSA-N 3,5-dibromo-L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC(Br)=C(O)C(Br)=C1 COESHZUDRKCEPA-ZETCQYMHSA-N 0.000 description 1
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- LKZIEAUIOCGXBY-AOIFVJIMSA-N 3-hydroxy-L-glutamic acid Chemical compound OC(=O)[C@@H](N)C(O)CC(O)=O LKZIEAUIOCGXBY-AOIFVJIMSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 230000010736 Chelating Activity Effects 0.000 description 1
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
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- 229960004799 tryptophan Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939322648A GB9322648D0 (en) | 1993-11-03 | 1993-11-03 | Process for the production of s.s.e.d.d.s |
| PCT/GB1994/002397 WO1995012570A2 (en) | 1993-11-03 | 1994-11-02 | Alkylation of amino acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69409500D1 DE69409500D1 (de) | 1998-05-14 |
| DE69409500T2 true DE69409500T2 (de) | 1998-09-24 |
Family
ID=10744563
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69409500T Expired - Lifetime DE69409500T2 (de) | 1993-11-03 | 1994-11-02 | Alkylierung von aminosäuren |
| DE69422643T Expired - Lifetime DE69422643T2 (de) | 1993-11-03 | 1994-11-02 | Alkylierung von Aminosäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69422643T Expired - Lifetime DE69422643T2 (de) | 1993-11-03 | 1994-11-02 | Alkylierung von Aminosäuren |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US5849948A (enExample) |
| EP (2) | EP0677037B1 (enExample) |
| JP (2) | JP2888494B2 (enExample) |
| AT (2) | ATE164829T1 (enExample) |
| AU (1) | AU683948B2 (enExample) |
| CA (1) | CA2151043C (enExample) |
| DE (2) | DE69409500T2 (enExample) |
| GB (2) | GB9322648D0 (enExample) |
| ID (1) | ID24668A (enExample) |
| IL (1) | IL111444A0 (enExample) |
| IN (1) | IN185844B (enExample) |
| MY (2) | MY119883A (enExample) |
| NZ (1) | NZ274912A (enExample) |
| TW (1) | TW381071B (enExample) |
| WO (1) | WO1995012570A2 (enExample) |
| ZA (1) | ZA948623B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9322648D0 (en) | 1993-11-03 | 1993-12-22 | Ass Octel | Process for the production of s.s.e.d.d.s |
| US5554791A (en) * | 1994-07-11 | 1996-09-10 | Albemarle Corporation | Process for producing [S,S]-ethylenediamine-N,N'-disuccinic acid |
| GB9422761D0 (en) * | 1994-11-11 | 1995-01-04 | Ass Octel | Use of a compound |
| GB9422762D0 (en) * | 1994-11-11 | 1995-01-04 | Ass Octel | Use of a compound |
| GB9507659D0 (en) * | 1995-04-13 | 1995-05-31 | Ass Octel | Alkylation process |
| WO1996035662A1 (en) * | 1995-05-09 | 1996-11-14 | Nitto Chemical Industry Co., Ltd. | Process for producing alkylenediaminediorganic acid and salts thereof |
| BR9610178A (pt) | 1995-08-30 | 1998-08-11 | Dow Chemical Co | Composição de detergente para lavanderia composição para lava-louças automático método para lavar tecidos processo para remover nox de um fluido método para deposição não elétrica de cobre e composição para quelar um mental |
| EP0783034B1 (en) | 1995-12-22 | 2010-08-18 | Mitsubishi Rayon Co., Ltd. | Chelating agent and detergent comprising the same |
| DE19620644A1 (de) | 1996-05-22 | 1997-11-27 | Ciba Geigy Ag | Verwendung von stickstoffhaltigen Komplexbildnern zur Desodorierung und antimikrobiellen Behandlung der Haut und textilen Fasermaterialien |
| US5731468A (en) * | 1997-04-03 | 1998-03-24 | The Dow Chemical Company | Preparation of disodium ethylenediamine-N,N'-disuccinate |
| GB9721394D0 (en) * | 1997-10-09 | 1997-12-10 | Ass Octel | Anti-microbial compound |
| CN1177809C (zh) * | 1998-08-12 | 2004-12-01 | 味之素株式会社 | 新型聚氨基酸衍生物 |
| EP1660433A2 (en) * | 2003-07-24 | 2006-05-31 | The Queen's Medical Center | Preparation and use of alkylating agents |
| KR101595614B1 (ko) | 2013-05-16 | 2016-02-18 | 코오롱인더스트리 주식회사 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
| WO2022169930A1 (en) * | 2021-02-03 | 2022-08-11 | Spero Renewables, Llc | Integrated process for making diastereopure ethylenediamine disuccinic acid (edds) from ethylene and aspartic acid using bromine as an intermediate |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2564092A (en) * | 1948-05-12 | 1951-08-14 | Frederick C Bersworth | Poly-ethylene poly-amino acid compounds |
| US3077487A (en) * | 1959-06-17 | 1963-02-12 | Victor Chemical Works | Lower alkylene and lower alkylenephenylene-lower alkylene polyamine bis n, n'-lower alkylene di and tri carboxylic acids, esters, salts, and chelates |
| US3158636A (en) * | 1963-10-29 | 1964-11-24 | Ethyl Corp | Manufacture of mixed alkyllead compounds |
| US4299978A (en) * | 1979-04-04 | 1981-11-10 | Showa Denko Kabushiki Kaisha | Process for separating iminodiacetic acid from aqueous glycine solution |
| US4704233A (en) * | 1986-11-10 | 1987-11-03 | The Procter & Gamble Company | Detergent compositions containing ethylenediamine-N,N'-disuccinic acid |
| US5629020A (en) | 1994-04-22 | 1997-05-13 | Emisphere Technologies, Inc. | Modified amino acids for drug delivery |
| JP3034969B2 (ja) | 1991-03-01 | 2000-04-17 | 旭化成工業株式会社 | アンモニア、α−アミノ酸類またはα−ケト酸の高感度定量法および高感度定量用組成物 |
| WO1993005014A1 (en) | 1991-09-05 | 1993-03-18 | Pharno-Wedropharm Gmbh | Aromatic sulfonamide derivatives, their use as enzyme inhibitors and pharmaceutical compositions containing them |
| GB9216409D0 (en) * | 1992-08-01 | 1992-09-16 | Procter & Gamble | Detergent compositions |
| GB9322648D0 (en) | 1993-11-03 | 1993-12-22 | Ass Octel | Process for the production of s.s.e.d.d.s |
| US5587512A (en) * | 1994-07-11 | 1996-12-24 | Albemarle Corporation | Process for obtaining [S,S]-ethylenediamine-n,n'-disuccinic acid from a salt solution of such acid and l-aspartic acid |
| US5550285A (en) * | 1994-07-11 | 1996-08-27 | Albemarle Corp | Method for producing calcium salts of [S,S]-ethylenediamine-N,N'-disuccinic acid |
| US5554791A (en) * | 1994-07-11 | 1996-09-10 | Albemarle Corporation | Process for producing [S,S]-ethylenediamine-N,N'-disuccinic acid |
| US5466867A (en) * | 1994-07-11 | 1995-11-14 | Albemarle Corporation | Method for producing [S,S]-ethylenediamine-N,N'-disuccinic acid from its calcium salt |
| US5660701A (en) | 1996-02-29 | 1997-08-26 | Bio-Rad Laboratories, Inc. | Protein separations by capillary electrophoresis using amino acid-containing buffers |
-
1993
- 1993-11-03 GB GB939322648A patent/GB9322648D0/en active Pending
-
1994
- 1994-10-28 IL IL11144494A patent/IL111444A0/xx not_active IP Right Cessation
- 1994-11-01 MY MYPI20002231A patent/MY119883A/en unknown
- 1994-11-01 MY MYPI94002899A patent/MY114136A/en unknown
- 1994-11-01 IN IN1059MA1994 patent/IN185844B/en unknown
- 1994-11-01 ID IDP20000376D patent/ID24668A/id unknown
- 1994-11-02 WO PCT/GB1994/002397 patent/WO1995012570A2/en not_active Ceased
- 1994-11-02 DE DE69409500T patent/DE69409500T2/de not_active Expired - Lifetime
- 1994-11-02 EP EP94931141A patent/EP0677037B1/en not_active Expired - Lifetime
- 1994-11-02 GB GB9513302A patent/GB2291423B/en not_active Expired - Fee Related
- 1994-11-02 JP JP7513083A patent/JP2888494B2/ja not_active Expired - Lifetime
- 1994-11-02 DE DE69422643T patent/DE69422643T2/de not_active Expired - Lifetime
- 1994-11-02 AU AU80017/94A patent/AU683948B2/en not_active Ceased
- 1994-11-02 AT AT94931141T patent/ATE164829T1/de not_active IP Right Cessation
- 1994-11-02 ZA ZA948623A patent/ZA948623B/xx unknown
- 1994-11-02 CA CA002151043A patent/CA2151043C/en not_active Expired - Fee Related
- 1994-11-02 US US08/481,286 patent/US5849948A/en not_active Expired - Lifetime
- 1994-11-02 EP EP96203178A patent/EP0765863B1/en not_active Expired - Lifetime
- 1994-11-02 NZ NZ274912A patent/NZ274912A/en not_active IP Right Cessation
- 1994-11-02 AT AT96203178T patent/ATE188686T1/de active
- 1994-11-03 TW TW083110156A patent/TW381071B/zh not_active IP Right Cessation
-
1998
- 1998-07-23 US US09/121,295 patent/US6075164A/en not_active Expired - Lifetime
- 1998-10-14 JP JP29262898A patent/JP3294559B2/ja not_active Expired - Fee Related
-
2000
- 2000-05-05 US US09/566,217 patent/US6278020B1/en not_active Expired - Lifetime
-
2001
- 2001-06-25 US US09/891,042 patent/US20020019566A1/en not_active Abandoned
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: INNOSPEC LTD., ELLESMERE PORT, CHESHIRE, GB |