SK3272000A3 - Acid salts of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l- -phenylalanine 1-methyl ester - Google Patents

Acid salts of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l- -phenylalanine 1-methyl ester Download PDF

Info

Publication number: SK3272000A3
Authority: SK; Slovakia
Prior art keywords: salt; dimethylbutyl; phenylalanine; methyl ester; aspartyl
Prior art date: 1997-09-11

Application number

SK327-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Indra Prakash

Kurt L Wachholder

Original Assignee

Nutrasweet Co

Priority date (The priority date 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 date listed.)

1997-09-11

Filing date

1998-09-11

Publication date

2000-10-09

1998-09-11 Application filed by Nutrasweet Co filed Critical Nutrasweet Co

2000-10-09 Publication of SK3272000A3 publication Critical patent/SK3272000A3/sk

Links

150000003839 salts Chemical class 0.000 title claims abstract description 37
HLIAVLHNDJUHFG-HOTGVXAUSA-N neotame Chemical class CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-HOTGVXAUSA-N 0.000 title abstract description 3
239000002253 acid Substances 0.000 title description 10
-1 maleiate Chemical compound 0.000 claims abstract description 16
235000013615 non-nutritive sweetener Nutrition 0.000 claims abstract description 10
239000007788 liquid Substances 0.000 claims abstract description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims abstract description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 6
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims abstract description 6
229940050410 gluconate Drugs 0.000 claims abstract description 6
229940049920 malate Drugs 0.000 claims abstract description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract 4
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract 4
235000010357 aspartame Nutrition 0.000 claims description 42
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 claims description 34
YHHAZJVJJCTGLB-GJZGRUSLSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-(3,3-dimethylbutylamino)-4-oxobutanoic acid Chemical compound CC(C)(C)CCN[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YHHAZJVJJCTGLB-GJZGRUSLSA-N 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical class 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 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
229940022663 acetate Drugs 0.000 claims description 5
229940050390 benzoate Drugs 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
229940095064 tartrate Drugs 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
150000008043 acidic salts Chemical group 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
235000003599 food sweetener Nutrition 0.000 abstract description 12
239000003765 sweetening agent Substances 0.000 abstract description 12
108010016626 Dipeptides Proteins 0.000 abstract description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 9
108010011485 Aspartame Proteins 0.000 description 8
239000000605 aspartame Substances 0.000 description 8
229960003438 aspartame Drugs 0.000 description 8
229960005190 phenylalanine Drugs 0.000 description 8
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
235000013305 food Nutrition 0.000 description 4
238000000034 method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000000007 visual effect Effects 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
235000009508 confectionery Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000013361 beverage Nutrition 0.000 description 2
239000000428 dust Substances 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
239000004384 Neotame Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
235000012174 carbonated soft drink Nutrition 0.000 description 1
150000004653 carbonic acids Chemical class 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000003841 chloride salts Chemical class 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
235000019412 neotame Nutrition 0.000 description 1
108010070257 neotame Proteins 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000008961 swelling Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Nutrition Science (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Seasonings (AREA)
Peptides Or Proteins (AREA)

SK327-2000A 1997-09-11 1998-09-11 Acid salts of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l- -phenylalanine 1-methyl ester SK3272000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5850597P	1997-09-11	1997-09-11
PCT/US1998/018902 WO1999012956A1 (fr)	1997-09-11	1998-09-11	SELS ACIDES DE N-[N-3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER

Publications (1)

Publication Number	Publication Date
SK3272000A3 true SK3272000A3 (en)	2000-10-09

Family

ID=22017224

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK327-2000A SK3272000A3 (en)	1997-09-11	1998-09-11	Acid salts of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l- -phenylalanine 1-methyl ester

Country Status (18)

Country	Link
US (1)	US6180156B1 (fr)
EP (1)	EP1012168A1 (fr)
CN (1)	CN1278827A (fr)
AU (1)	AU753013B2 (fr)
BG (1)	BG104323A (fr)
BR (1)	BR9812635A (fr)
CA (1)	CA2303436A1 (fr)
EE (1)	EE200000119A (fr)
HU (1)	HUP0003573A3 (fr)
ID (1)	ID27534A (fr)
IL (1)	IL134914A0 (fr)
LT (1)	LT4759B (fr)
NO (1)	NO20001270L (fr)
PL (1)	PL339207A1 (fr)
SI (1)	SI20330A (fr)
SK (1)	SK3272000A3 (fr)
TR (1)	TR200000730T2 (fr)
WO (1)	WO1999012956A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6692778B2 (en)	1998-06-05	2004-02-17	Wm. Wrigley Jr. Company	Method of controlling release of N-substituted derivatives of aspartame in chewing gum
AU3914200A (en) *	1999-03-25	2000-10-09	Nutrasweet Company, The	Edible gels sweetened with n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester
US6365216B1 (en)	1999-03-26	2002-04-02	The Nutrasweet Company	Particles of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
AU4994700A (en) *	1999-05-13	2000-12-05	Nutrasweet Company, The	Modification of the taste and physicochemical properties of neotame using hydrophobic acid additives
WO2000069283A1 (fr) *	1999-05-13	2000-11-23	The Nutrasweet Company	UTILISATION D'ADDITIFS POUR MODIFIER LES CARACTERISTIQUES GUSTATIVES DE N-NEOHEXYL $G(a)-ASPARTYL-L-PHENYLALANINE METHYLESTER
US7326430B2 (en) *	2000-07-18	2008-02-05	The Nutrasweet Company	Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems
US20080008790A1 (en) *	2006-06-30	2008-01-10	Michael Jensen	Seasoned food, seasoning, and method for seasoning a food product
US7923047B2 (en) *	2006-06-30	2011-04-12	Conagra Foods Rdm, Inc.	Seasoning and method for seasoning a food product while reducing dietary sodium intake
US20080038411A1 (en) *	2006-06-30	2008-02-14	Michael Jensen	Seasoning and method for enhancing and potentiating food flavor
US20110097449A1 (en) *	2006-06-30	2011-04-28	Conagra Foods Rdm, Inc.	Seasoning and method for seasoning a food product while reducing dietary sodium intake
NZ575995A (en) *	2006-09-27	2011-03-31	Conagra Foods Rdm Inc	Seasoning and method for enhancing and potentiating food flavor utilizing microencapsulation
CN109180914B (zh) *	2018-04-05	2021-02-02	河南金丹乳酸科技股份有限公司	利用l-乳酸经寡聚、熔融缩聚和固相缩聚生产聚l-乳酸的方法
CN112321676B (zh) *	2020-12-12	2022-06-14	山东诚汇双达药业有限公司	一种纽甜的成盐方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1431057A (en) *	1972-03-30	1976-04-07	Gen Foods Corp	Sweetining compositions
US4031258A (en)	1972-03-30	1977-06-21	General Foods Corporation	Inorganic salts of dipeptide sweeteners
US4029701A (en)	1972-03-30	1977-06-14	General Foods Corporation	Sweetening with hydrohalide salts of dipeptide sweeteners
CA1028197A (fr)	1973-04-02	1978-03-21	Jeffrey H. Berg	Edulcorant concentre a faible teneur en calories
US4448716A (en)	1982-03-04	1984-05-15	G. D. Searle & Co.	Dipeptide sweetener-metal complexes
FR2697844B1 (fr)	1992-11-12	1995-01-27	Claude Nofre	Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation.
FR2719590B1 (fr)	1994-05-09	1996-07-26	Claude Nofre	Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant.
AU3075195A (en)	1994-06-28	1996-01-25	Twinklestar Investments N.V.	A communication system for supplying information on objects on display by means of hand-held devices
US5728862A (en)	1997-01-29	1998-03-17	The Nutrasweet Company	Method for preparing and purifying an N-alkylated aspartame derivative
JPH10259194A (ja) *	1997-03-18	1998-09-29	Ajinomoto Co Inc	新規ジペプチド誘導体及び甘味剤

1998
- 1998-09-04 US US09/146,964 patent/US6180156B1/en not_active Expired - Fee Related
- 1998-09-11 IL IL13491498A patent/IL134914A0/xx unknown
- 1998-09-11 EE EEP200000119A patent/EE200000119A/xx unknown
- 1998-09-11 CN CN98811056A patent/CN1278827A/zh active Pending
- 1998-09-11 SI SI9820062A patent/SI20330A/sl unknown
- 1998-09-11 HU HU0003573A patent/HUP0003573A3/hu unknown
- 1998-09-11 BR BR9812635-0A patent/BR9812635A/pt not_active Application Discontinuation
- 1998-09-11 WO PCT/US1998/018902 patent/WO1999012956A1/fr not_active Ceased
- 1998-09-11 TR TR2000/00730T patent/TR200000730T2/xx unknown
- 1998-09-11 PL PL98339207A patent/PL339207A1/xx unknown
- 1998-09-11 AU AU93844/98A patent/AU753013B2/en not_active Ceased
- 1998-09-11 CA CA002303436A patent/CA2303436A1/fr not_active Abandoned
- 1998-09-11 SK SK327-2000A patent/SK3272000A3/sk unknown
- 1998-09-11 ID IDW20000471D patent/ID27534A/id unknown
- 1998-09-11 EP EP98946938A patent/EP1012168A1/fr not_active Ceased
2000
- 2000-03-10 NO NO20001270A patent/NO20001270L/no not_active Application Discontinuation
- 2000-04-06 LT LT2000026A patent/LT4759B/lt not_active IP Right Cessation
- 2000-04-10 BG BG104323A patent/BG104323A/xx unknown

Also Published As

Publication number	Publication date
US6180156B1 (en)	2001-01-30
WO1999012956A1 (fr)	1999-03-18
EP1012168A1 (fr)	2000-06-28
LT2000026A (en)	2000-09-25
IL134914A0 (en)	2001-05-20
NO20001270D0 (no)	2000-03-10
ID27534A (id)	2001-04-12
EE200000119A (et)	2000-12-15
SI20330A (sl)	2001-02-28
HUP0003573A3 (en)	2001-08-28
CA2303436A1 (fr)	1999-03-18
BG104323A (en)	2001-02-28
AU753013B2 (en)	2002-10-03
AU9384498A (en)	1999-03-29
PL339207A1 (en)	2000-12-04
NO20001270L (no)	2000-05-10
TR200000730T2 (tr)	2001-06-21
LT4759B (lt)	2001-02-26
BR9812635A (pt)	2000-08-22
HUP0003573A2 (hu)	2001-05-28
CN1278827A (zh)	2001-01-03

Publication	Publication Date	Title
US6291004B1 (en)	2001-09-18	Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester
SK3272000A3 (en)	2000-10-09	Acid salts of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l- -phenylalanine 1-methyl ester
US6129942A (en)	2000-10-10	Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
US6146680A (en)	2000-11-14	Metal complexes of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
CZ2000815A3 (cs)	2000-10-11	Kyselé soli 1-metylesteru N-[N-(3,3- dimetylbutyl)-L-alfa-aspartyl]-L-fenylalaninu
MXPA00002540A (en)	2001-11-21	ACID SALTS OF N-[N-(3,3-DIMETHYLBUTYL)-L-&agr;-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
MXPA00002539A (en)	2001-11-21	BASIC SALTS OF N-[N-(3,3-DIMETHYLBUTYL)-L-&agr;-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
MXPA00002552A (en)	2001-11-21	METAL COMPLEXES OF N-[N-(3,3-DIMETHYLBUTYL) -L-&agr;-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
CZ2000814A3 (cs)	2000-10-11	Zásadité soli 1-metylesteru N-[N-(3,3- dimetylbutyl)-L-alfa-aspartyl]-L-fenylalaninu
CZ2000818A3 (cs)	2000-10-11	Komplexy 1-metylesteru N-[N-(3,3-dimetylbutyl)- L-alfa-aspartyl]-L-fenylalaninu s kovy
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