NO875312L - Fremgangsmaate for fremstilling av alfa-l-aspartyl-l-fenylalanin-methylester med lav hygroskopisitet. - Google Patents
Fremgangsmaate for fremstilling av alfa-l-aspartyl-l-fenylalanin-methylester med lav hygroskopisitet.Info
- Publication number
- NO875312L NO875312L NO875312A NO875312A NO875312L NO 875312 L NO875312 L NO 875312L NO 875312 A NO875312 A NO 875312A NO 875312 A NO875312 A NO 875312A NO 875312 L NO875312 L NO 875312L
- Authority
- NO
- Norway
- Prior art keywords
- apm
- cake
- organic solvent
- aspartyl
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 239000003960 organic solvent Substances 0.000 claims description 42
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 14
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000001035 drying Methods 0.000 description 28
- 239000013078 crystal Substances 0.000 description 26
- 230000004580 weight loss Effects 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- -1 diketopiperazine compound Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 235000013373 food additive Nutrition 0.000 description 3
- 239000002778 food additive Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WYYUBJAMROQJSF-QWRGUYRKSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-formamido-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 WYYUBJAMROQJSF-QWRGUYRKSA-N 0.000 description 1
- YSCNREZXFSZAQO-ROUUACIJSA-N (3s)-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxo-3-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@H](CC(O)=O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 YSCNREZXFSZAQO-ROUUACIJSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- VNHJXYUDIBQDDX-UHFFFAOYSA-N L-cis-Cyclo(aspartylphenylalanyl) Chemical compound N1C(=O)C(CC(=O)O)NC(=O)C1CC1=CC=CC=C1 VNHJXYUDIBQDDX-UHFFFAOYSA-N 0.000 description 1
- MQUUQXIFCBBFDP-VKHMYHEASA-N N-formyl-L-aspartic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC=O MQUUQXIFCBBFDP-VKHMYHEASA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006198 deformylation Effects 0.000 description 1
- 238000006344 deformylation reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- 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
- C07K1/14—Extraction; Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61301469A JPH0832719B2 (ja) | 1986-12-19 | 1986-12-19 | 吸湿性の小さいα−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO875312D0 NO875312D0 (no) | 1987-12-18 |
| NO875312L true NO875312L (no) | 1988-06-20 |
Family
ID=17897271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO875312A NO875312L (no) | 1986-12-19 | 1987-12-18 | Fremgangsmaate for fremstilling av alfa-l-aspartyl-l-fenylalanin-methylester med lav hygroskopisitet. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4962222A (ja) |
| EP (1) | EP0272062B1 (ja) |
| JP (1) | JPH0832719B2 (ja) |
| KR (1) | KR900008013B1 (ja) |
| AU (1) | AU589053B2 (ja) |
| BR (1) | BR8706921A (ja) |
| CA (1) | CA1318458C (ja) |
| DE (1) | DE3787082T2 (ja) |
| NO (1) | NO875312L (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0718306B1 (en) * | 1994-12-22 | 2001-05-30 | Holland Sweetener Company V.O.F. | Crystallization of alpha-L-aspartyl-L-phenylalanine methyl ester from aqueous solution |
| DE69521110T2 (de) * | 1994-12-22 | 2002-03-07 | Holland Sweetener Co. V.O.F., Maastricht | Crystallisierung vom Alpha-L-Aspartyl-L-phenylalanylmethylester aus wässrigen Lösungen |
| EP0751146B1 (en) * | 1995-06-30 | 2002-03-13 | Holland Sweetener Company V.o.F. | Crystallization of alpha-L-aspartyl-L-phenylalanine methyl ester from aqueous solution |
| US6293692B1 (en) * | 1999-11-05 | 2001-09-25 | M. William Bowsher | Multipurpose container structure |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791544A (fr) * | 1971-11-19 | 1973-05-17 | Stamicarbon | Preparation d'esters alkyliques de dipeptide |
| JPS4896557A (ja) * | 1972-03-22 | 1973-12-10 | ||
| CA1028197A (en) * | 1973-04-02 | 1978-03-21 | Jeffrey H. Berg | Concentrated liquid low calorie sweetener |
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| JPS5140069A (ja) * | 1974-10-02 | 1976-04-03 | Hitachi Ltd | |
| JPS5823380B2 (ja) * | 1974-12-05 | 1983-05-14 | 味の素株式会社 | ホルミルキノ ダツリホウ |
| JPS51113841A (en) * | 1975-03-28 | 1976-10-07 | Ajinomoto Co Inc | Process for preparing lower alkyl esters of n-formyl-alpha -l-aspartyl-l-phenylalanine |
| US4088649A (en) * | 1975-07-02 | 1978-05-09 | Firmenich S.A. | Process for preparing a diketo-piperazine |
| JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
| MX4704E (es) * | 1976-12-27 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de ester metilico de alfa-l-aspartil-l-fenilalanina |
| JPS58185545A (ja) * | 1982-04-22 | 1983-10-29 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルまたはその塩酸塩の製法 |
| GB2133409B (en) * | 1983-01-13 | 1986-03-05 | Erba Farmitalia | Aspartame synthesis |
| GB8300810D0 (en) * | 1983-01-13 | 1983-02-16 | Erba Farmitalia | Aspartame synthesis |
| JPH0631312B2 (ja) * | 1983-03-18 | 1994-04-27 | 味の素株式会社 | ジペプチド結晶及びその製造方法 |
| JPH0622457B2 (ja) * | 1983-08-10 | 1994-03-30 | 味の素株式会社 | ジペプチド甘味料含有錠剤又は顆粒及びその製造法 |
| JPS59219258A (ja) * | 1983-05-28 | 1984-12-10 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 |
| JPS59225152A (ja) * | 1983-06-02 | 1984-12-18 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 |
| JPH0613550B2 (ja) * | 1983-06-03 | 1994-02-23 | 味の素株式会社 | α―Ｌ―アスパルチル―Ｌ―フェニルアラニン―低級アルキルエステルの製造法 |
| JPS59227849A (ja) * | 1983-06-08 | 1984-12-21 | Ajinomoto Co Inc | Ｌ―α―アスパルチル―Ｌ―フェニルアラニンメチルエステル束状晶の晶析分離法 |
| JPS6050200A (ja) * | 1983-08-30 | 1985-03-19 | Nippon Kokan Kk <Nkk> | 金属ストリップのクリーニング洗浄液の浄化装置 |
| JPS60174799A (ja) * | 1984-02-21 | 1985-09-09 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造法 |
| JPH0710878B2 (ja) * | 1986-07-28 | 1995-02-08 | 東ソー株式会社 | 溶解性の改善されたα−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造方法 |
| US4835303A (en) * | 1986-08-12 | 1989-05-30 | Toyo Soda Manufacturing Company, Ltd. | Process for producing dry α-L-aspartyl-L-phenylalanine methyl ester |
| JPS6345298A (ja) * | 1986-08-13 | 1988-02-26 | Tosoh Corp | 安定なα−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造方法 |
| JPH07103154B2 (ja) * | 1986-08-13 | 1995-11-08 | 東ソー株式会社 | 安定なα−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造方法 |
-
1986
- 1986-12-19 JP JP61301469A patent/JPH0832719B2/ja not_active Expired - Lifetime
-
1987
- 1987-12-09 CA CA000553915A patent/CA1318458C/en not_active Expired - Fee Related
- 1987-12-10 AU AU82291/87A patent/AU589053B2/en not_active Ceased
- 1987-12-11 EP EP87310909A patent/EP0272062B1/en not_active Expired - Lifetime
- 1987-12-11 DE DE87310909T patent/DE3787082T2/de not_active Expired - Fee Related
- 1987-12-18 BR BR8706921A patent/BR8706921A/pt unknown
- 1987-12-18 NO NO875312A patent/NO875312L/no unknown
- 1987-12-18 KR KR1019870014475A patent/KR900008013B1/ko not_active IP Right Cessation
-
1989
- 1989-01-25 US US07/300,724 patent/US4962222A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0272062A2 (en) | 1988-06-22 |
| EP0272062A3 (en) | 1990-04-25 |
| KR900008013B1 (ko) | 1990-10-29 |
| KR880007561A (ko) | 1988-08-27 |
| EP0272062B1 (en) | 1993-08-18 |
| CA1318458C (en) | 1993-05-25 |
| JPS63156800A (ja) | 1988-06-29 |
| JPH0832719B2 (ja) | 1996-03-29 |
| DE3787082T2 (de) | 1994-04-07 |
| AU589053B2 (en) | 1989-09-28 |
| US4962222A (en) | 1990-10-09 |
| BR8706921A (pt) | 1988-07-26 |
| DE3787082D1 (de) | 1993-09-23 |
| NO875312D0 (no) | 1987-12-18 |
| AU8229187A (en) | 1988-06-23 |
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