BG63537B1 - Креатинови пирувати и метод за тяхното получаване - Google Patents

Креатинови пирувати и метод за тяхното получаване Download PDF

Info

Publication number: BG63537B1
Authority: BG; Bulgaria
Prior art keywords: creatine; pyruvates; pyruvic acid; pyruvate; creatine pyruvates
Prior art date: 1996-12-20

Application number

BG102932A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102932A (en

Inventor

Ivo Pischel

Stefan Weiss

Original Assignee

Skw Trostberg Aktiengesellschaft

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.)

1996-12-20

Filing date

1998-11-18

Publication date

2002-04-30

1996-12-20 Priority claimed from DE19653225A external-priority patent/DE19653225A1/de

1998-11-18 Application filed by Skw Trostberg Aktiengesellschaft filed Critical Skw Trostberg Aktiengesellschaft

1999-09-30 Publication of BG102932A publication Critical patent/BG102932A/xx

2002-04-30 Publication of BG63537B1 publication Critical patent/BG63537B1/bg

Links

CVSVTCORWBXHQV-UHFFFAOYSA-N anhydrous creatine Natural products NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract description 77
229960003624 creatine Drugs 0.000 title claims abstract description 48
239000006046 creatine Substances 0.000 title claims abstract description 48
-1 Creatine pyruvates Chemical class 0.000 title claims abstract description 29
238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims abstract description 38
238000006243 chemical reaction Methods 0.000 claims abstract description 7
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims abstract description 5
208000008589 Obesity Diseases 0.000 claims abstract description 4
206010033307 Overweight Diseases 0.000 claims abstract description 4
235000020824 obesity Nutrition 0.000 claims abstract description 4
208000028867 ischemia Diseases 0.000 claims abstract description 3
229940107700 pyruvic acid Drugs 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 10
229940076788 pyruvate Drugs 0.000 claims description 8
235000015872 dietary supplement Nutrition 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 6
150000001413 amino acids Chemical class 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 3
150000001720 carbohydrates Chemical class 0.000 claims description 3
235000014633 carbohydrates Nutrition 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
235000010755 mineral Nutrition 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000011782 vitamin Substances 0.000 claims description 3
235000013343 vitamin Nutrition 0.000 claims description 3
229940088594 vitamin Drugs 0.000 claims description 3
229930003231 vitamin Natural products 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
235000001014 amino acid Nutrition 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims description 2
229940123457 Free radical scavenger Drugs 0.000 claims 1
210000000577 adipose tissue Anatomy 0.000 claims 1
230000002708 enhancing effect Effects 0.000 claims 1
230000007774 longterm Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000002516 radical scavenger Substances 0.000 claims 1
210000003205 muscle Anatomy 0.000 abstract description 6
206010021143 Hypoxia Diseases 0.000 abstract description 2
235000013373 food additive Nutrition 0.000 abstract description 2
239000002778 food additive Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
DLNGCCQFGNSBOP-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;2-oxopropanoic acid Chemical compound CC(=O)C(O)=O.NC(=N)N(C)CC(O)=O DLNGCCQFGNSBOP-UHFFFAOYSA-N 0.000 description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000004728 pyruvic acid derivatives Chemical class 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000004682 monohydrates Chemical class 0.000 description 3
239000004570 mortar (masonry) Substances 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
229940018333 calcium pyruvate Drugs 0.000 description 1
UZWMCCLZMHPPKW-UHFFFAOYSA-L calcium;2-oxopropanoate Chemical compound [Ca+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O UZWMCCLZMHPPKW-UHFFFAOYSA-L 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229940109239 creatinine Drugs 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
210000000663 muscle cell Anatomy 0.000 description 1
230000004220 muscle function Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
JKVUQLWTIZFTMF-UHFFFAOYSA-M potassium;2-oxopropanoate Chemical compound [K+].CC(=O)C([O-])=O JKVUQLWTIZFTMF-UHFFFAOYSA-M 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
230000014616 translation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/19—Pyruvic acid

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Hematology (AREA)
Obesity (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Child & Adolescent Psychology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)
Extrusion Moulding Of Plastics Or The Like (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

BG102932A 1996-12-20 1998-11-18 Креатинови пирувати и метод за тяхното получаване BG63537B1 (bg)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19653225A DE19653225A1 (de)	1996-12-20	1996-12-20	Kreatin-pyruvate und Verfahren zu deren Herstellung
US08/893,423 US6166249A (en)	1996-12-20	1997-07-11	Creatine pyruvates
PCT/EP1997/007121 WO1998028263A1 (fr)	1996-12-20	1997-12-18	Creatine pyruvates et leur procede de preparation

Publications (2)

Publication Number	Publication Date
BG102932A BG102932A (en)	1999-09-30
BG63537B1 true BG63537B1 (bg)	2002-04-30

Family

ID=26032506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG102932A BG63537B1 (bg)	1996-12-20	1998-11-18	Креатинови пирувати и метод за тяхното получаване

Country Status (22)

Country	Link
US (1)	US6172111B1 (fr)
EP (1)	EP0894083B1 (fr)
JP (1)	JP3090960B2 (fr)
CN (1)	CN1076343C (fr)
AT (1)	ATE186295T1 (fr)
AU (1)	AU727524B2 (fr)
BG (1)	BG63537B1 (fr)
BR (1)	BR9711954A (fr)
CA (1)	CA2255665C (fr)
CZ (1)	CZ293282B6 (fr)
DE (1)	DE59700666D1 (fr)
DK (1)	DK0894083T3 (fr)
ES (1)	ES2139465T3 (fr)
GR (1)	GR3031754T3 (fr)
IL (1)	IL127148A (fr)
NO (1)	NO311354B1 (fr)
NZ (1)	NZ332830A (fr)
PL (1)	PL330279A1 (fr)
RU (1)	RU2179970C2 (fr)
SK (1)	SK283195B6 (fr)
TR (1)	TR199900470T2 (fr)
WO (1)	WO1998028263A1 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1051914A1 (fr) *	1999-05-08	2000-11-15	DSM Fine Chemicals Austria GmbH	Utilisation de la créatine comme additif pour l'alimentation animale
US6242491B1 (en) *	1999-06-25	2001-06-05	Rima Kaddurah-Daouk	Use of creatine or creatine compounds for skin preservation
DE19929995B4 (de)	1999-06-30	2004-06-03	Skw Trostberg Ag	Verwendung von Kreatin und/oder Kreatin-Derivaten zur Behandlung von Befindlichkeitsstörungen bei Frauen
AU6153200A (en) *	1999-06-30	2001-01-22	Skw Trostberg Aktiengesellschaft	Use of creatine and/or creatine derivatives for treating feelings of ill-health in women
DE10003835A1 (de) *	2000-01-28	2001-08-16	Sueddeutsche Kalkstickstoff	Formulierungen bei Dehydratationszuständen
US20030212136A1 (en)	2001-09-14	2003-11-13	Vennerstrom Jonathan L.	Creatine ester pronutrient compounds and formulations
EP1688139A1 (fr) *	2000-09-14	2006-08-09	Board of Regents of the University of Nebraska	Composés et formulations d'esters de créatine
DE10064312C2 (de) *	2000-12-22	2003-05-22	Degussa	Cholinpyruvat-Hydrat, Verfahren zu dessen Herstellung, Cholinpyruvat-Hydrat enthaltende Formulierung sowie deren Verwendung
US6838562B2 (en) *	2003-04-01	2005-01-04	Sal Abraham	Process for preparing a creatine heterocyclic acid salt and method of use
DE10355716A1 (de) *	2003-11-26	2005-06-23	Beiersdorf Ag	Kosmetische Zubereitungen mit einem Gehalt Kreatin und/oder Kreatinderivaten und/oder Kreatinin und/oderKreatininderivaten und organischen Verdickern
RS50556B (sr)	2004-06-09	2010-05-07	Alzchem Trostberg Gmbh.	Guanidino sirćetna kiselina kao dodatak hrani za životinje
DE102006031441B4 (de) *	2006-07-05	2011-12-29	Hans Matt	Orales Creatin-Supplement, sowie Verfahren zur Herstellung desselben
DE102007004781A1 (de)	2007-01-31	2008-08-07	Alzchem Trostberg Gmbh	Verwendung von Guanidinoessigsäure(-Salzen) zur Herstellung eines gesundheitsfördernden Mittels
DE102007030495A1 (de)	2007-06-30	2009-01-15	Alzchem Trostberg Gmbh	Verwendung einer eine Kreatin-Komponente enthaltende Zusammensetzung zur Verbesserung der Gedächtnisleistung, der Merkfähigkeit, des Langzeitgedächtnisses und zur Vorbeugung geistiger Ermüdungszustände
DE102007053369A1 (de)	2007-11-09	2009-07-02	Alzchem Trostberg Gmbh	Verwendung einer eine Kreatin-Komponente enthaltende Zusammensetzung zur Verbesserung der männlichen Fruchtbarkeit
DE102007062288A1 (de)	2007-12-21	2009-06-25	Alzchem Trostberg Gmbh	Kreatin-Zubereitung und Verfahren zu deren Herstellung
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1997
- 1997-12-18 CN CN97195889A patent/CN1076343C/zh not_active Expired - Fee Related
- 1997-12-18 ES ES97954423T patent/ES2139465T3/es not_active Expired - Lifetime
- 1997-12-18 JP JP10528354A patent/JP3090960B2/ja not_active Expired - Lifetime
- 1997-12-18 BR BR9711954A patent/BR9711954A/pt not_active IP Right Cessation
- 1997-12-18 CZ CZ19983626A patent/CZ293282B6/cs not_active IP Right Cessation
- 1997-12-18 IL IL12714897A patent/IL127148A/en not_active IP Right Cessation
- 1997-12-18 AT AT97954423T patent/ATE186295T1/de not_active IP Right Cessation
- 1997-12-18 EP EP97954423A patent/EP0894083B1/fr not_active Expired - Lifetime
- 1997-12-18 NZ NZ332830A patent/NZ332830A/xx unknown
- 1997-12-18 SK SK1556-98A patent/SK283195B6/sk unknown
- 1997-12-18 TR TR1999/00470T patent/TR199900470T2/xx unknown
- 1997-12-18 AU AU58576/98A patent/AU727524B2/en not_active Ceased
- 1997-12-18 WO PCT/EP1997/007121 patent/WO1998028263A1/fr not_active Ceased
- 1997-12-18 DK DK97954423T patent/DK0894083T3/da active
- 1997-12-18 PL PL97330279A patent/PL330279A1/xx unknown
- 1997-12-18 DE DE59700666T patent/DE59700666D1/de not_active Expired - Fee Related
- 1997-12-18 RU RU98122207/04A patent/RU2179970C2/ru not_active IP Right Cessation
- 1997-12-18 CA CA002255665A patent/CA2255665C/fr not_active Expired - Fee Related
1998
- 1998-11-18 BG BG102932A patent/BG63537B1/bg unknown
1999
- 1999-05-12 US US09/310,323 patent/US6172111B1/en not_active Expired - Fee Related
- 1999-05-31 NO NO19992603A patent/NO311354B1/no not_active IP Right Cessation
- 1999-11-04 GR GR990402819T patent/GR3031754T3/el unknown

Also Published As

Publication number	Publication date
EP0894083B1 (fr)	1999-11-03
PL330279A1 (en)	1999-05-10
NO311354B1 (no)	2001-11-19
HK1020718A1 (en)	2000-05-19
US6172111B1 (en)	2001-01-09
JP3090960B2 (ja)	2000-09-25
SK155698A3 (en)	1999-05-07
CZ362698A3 (cs)	1999-03-17
NO992603D0 (no)	1999-05-31
CZ293282B6 (cs)	2004-03-17
ES2139465T3 (es)	2000-02-01
SK283195B6 (sk)	2003-03-04
BG102932A (en)	1999-09-30
ATE186295T1 (de)	1999-11-15
NZ332830A (en)	2000-04-28
CA2255665A1 (fr)	1998-07-02
TR199900470T2 (xx)	1999-06-21
WO1998028263A1 (fr)	1998-07-02
DK0894083T3 (da)	2000-04-03
AU727524B2 (en)	2000-12-14
JPH11509560A (ja)	1999-08-24
GR3031754T3 (en)	2000-02-29
CA2255665C (fr)	2002-05-14
IL127148A0 (en)	1999-09-22
CN1224416A (zh)	1999-07-28
NO992603L (no)	1999-05-31
EP0894083A1 (fr)	1999-02-03
AU5857698A (en)	1998-07-17
DE59700666D1 (de)	1999-12-09
BR9711954A (pt)	1999-08-24
CN1076343C (zh)	2001-12-19
IL127148A (en)	2002-11-10
RU2179970C2 (ru)	2002-02-27

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AU727524B2 (en)	2000-12-14	Creatine pyruvates and a method of producing them
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JP4796493B2 (ja)	2011-10-19	Ｌ−リジン・クエン酸塩結晶
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EP0839459A1 (fr)	1998-05-06	Composition contenant du calcium facilement absorbable et son procede de fabrication
FR2752423A1 (fr)	1998-02-20	Procede de preparation d'une forme cristalline therapeutiquement active du sulfate de glucosamine et sulfate de glucosamine ainsi obtenu
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MXPA98010488A (en)	1999-07-06	Creatine pyruvates and method for their production
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EP0923932B1 (fr)	2011-06-29	Compositions contenant un agent antitumoral
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GB2344996A (en)	2000-06-28	A solid stable aggregate formed from a pyruvate component and a carbohydrate component
HK1020718B (en)	2002-05-31	Creatine pyruvates and method for their production
KR100461572B1 (ko)	2004-12-14	Ｌ-카르니틴 칼슘 염과 이의 제조방법
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US2478984A (en)	1949-08-16	Medicinal preparation containing available calcium and phosphorus
US3041345A (en)	1962-06-26	Process of preparation of isonicotinyl hydrazones and hydrazides
KR900000747B1 (ko)	1990-02-15	비경구용 세파만돌 나페이트 제제의 제조방법
MXPA99011864A (en)	2000-05-01	Method for producing calcium pyruvates
CZ457499A3 (cs)	2000-05-17	Způsob výroby vápenatých pyruvátů