SK280544B6 - Spôsob prípravy kreatínu alebo monohydrátu kreatín - Google Patents

Spôsob prípravy kreatínu alebo monohydrátu kreatín Download PDF

Info

Publication number: SK280544B6
Authority: SK; Slovakia
Prior art keywords: creatine; water; cyanamide; process according; sodium
Prior art date: 1995-07-18

Application number

SK939-96A

Other languages

English (en)

Slovak (sk)

Other versions

SK93996A3 (en

Inventor

Stefan Weiss

Helmut Krommer

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.)

1995-07-18

Filing date

1996-07-18

Publication date

2000-03-13

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7767164&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK280544(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-07-18 Application filed by Skw Trostberg Aktiengesellschaft filed Critical Skw Trostberg Aktiengesellschaft

1997-03-05 Publication of SK93996A3 publication Critical patent/SK93996A3/sk

2000-03-13 Publication of SK280544B6 publication Critical patent/SK280544B6/sk

Links

CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract description 48
239000006046 creatine Substances 0.000 title claims abstract description 23
229960004826 creatine monohydrate Drugs 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims abstract description 23
MEJYXFHCRXAUIL-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;hydrate Chemical compound O.NC(=N)N(C)CC(O)=O MEJYXFHCRXAUIL-UHFFFAOYSA-N 0.000 title claims abstract description 22
229960003624 creatine Drugs 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims abstract description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 28
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 claims abstract description 18
239000011734 sodium Substances 0.000 claims abstract description 18
229910052708 sodium Inorganic materials 0.000 claims abstract description 18
VILYDVYHBMHOSG-UHFFFAOYSA-M potassium;2-(methylamino)acetate Chemical compound [K+].CNCC([O-])=O VILYDVYHBMHOSG-UHFFFAOYSA-M 0.000 claims abstract description 16
239000003960 organic solvent Substances 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims abstract description 4
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 16
108010077895 Sarcosine Proteins 0.000 claims description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
239000007864 aqueous solution Substances 0.000 claims description 10
239000007795 chemical reaction product Substances 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
229940043230 sarcosine Drugs 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
238000010979 pH adjustment Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
150000004682 monohydrates Chemical class 0.000 claims 1
238000001035 drying Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
229940048098 sodium sarcosinate Drugs 0.000 description 7
ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 7
238000003756 stirring Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000002253 acid Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000001816 cooling Methods 0.000 description 3
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
239000008188 pellet Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229940071089 sarcosinate Drugs 0.000 description 3
238000005406 washing Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
-1 aromatic carboxylic acids Chemical class 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012620 biological material Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004927 clay Substances 0.000 description 1
229940109239 creatinine Drugs 0.000 description 1
XPQRZQHNWFOKMS-UHFFFAOYSA-N cyanamide;potassium Chemical compound [K].NC#N XPQRZQHNWFOKMS-UHFFFAOYSA-N 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000007603 infrared drying Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/02—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from cyanamide, calcium cyanamide or dicyandiamides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK939-96A 1995-07-18 1996-07-18 Spôsob prípravy kreatínu alebo monohydrátu kreatín SK280544B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19526236A DE19526236A1 (de)	1995-07-18	1995-07-18	Verfahren zur Herstellung von Kreatin bzw. Kreatin-monohydrat

Publications (2)

Publication Number	Publication Date
SK93996A3 SK93996A3 (en)	1997-03-05
SK280544B6 true SK280544B6 (sk)	2000-03-13

Family

ID=7767164

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK939-96A SK280544B6 (sk)	1995-07-18	1996-07-18	Spôsob prípravy kreatínu alebo monohydrátu kreatín

Country Status (16)

Country	Link
US (1)	US5719319A (cs)
EP (1)	EP0754679B1 (cs)
JP (1)	JP3056416B2 (cs)
CN (1)	CN1061647C (cs)
AT (1)	ATE172715T1 (cs)
CA (1)	CA2181026C (cs)
CZ (1)	CZ290563B6 (cs)
DE (2)	DE19526236A1 (cs)
DK (1)	DK0754679T3 (cs)
ES (1)	ES2126355T3 (cs)
HU (1)	HU218820B (cs)
NO (1)	NO305200B1 (cs)
PL (1)	PL184404B1 (cs)
RU (1)	RU2163233C2 (cs)
SI (1)	SI0754679T1 (cs)
SK (1)	SK280544B6 (cs)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU7718798A (en) *	1997-05-30	1998-12-30	Kellogg Company	Creatine containing cereal-based food product, processes for making these, and uses thereof
US6465018B1 (en) *	1997-08-22	2002-10-15	B. David Tuttle	Dietary supplement for increasing energy, strength, and immune function
DE19748695A1 (de) *	1997-11-04	1999-05-06	Basf Ag	Verfahren zur Herstellung von substituierten Guanidinderivaten
DE19748694A1 (de) *	1997-11-04	1999-05-06	Basf Ag	Verfahren zur Herstellung von substituierten Guanidinderivaten
DE19748697A1 (de) *	1997-11-04	1999-05-06	Basf Ag	Verfahren zur Herstellung von substituierten Guanidinderivaten
DE19748696A1 (de) *	1997-11-04	1999-05-06	Basf Ag	Verfahren zur Herstellung von substituierten Guanidinderivaten
CN1097578C (zh) *	1998-06-19	2003-01-01	李森	高纯度肌酸及其一水合物的生产工艺
DE19841525A1 (de) *	1998-09-10	2000-03-16	Basf Ag	Verfahren zur Herstellung von Kreatin oder Kreatin-monohydrat
DE19860048A1 (de) *	1998-12-23	2000-06-29	Basf Ag	Verfahren zur Herstellung von Guanidinderivaten
DE19905711A1 (de) *	1999-02-11	2000-08-17	Basf Ag	Verfahren zur Herstellung von Guanidinderivaten
CN1098251C (zh) *	1999-09-07	2003-01-08	天津天成制药有限公司	制备肌酸或肌酸-水合物的方法
DE19962227A1 (de) *	1999-12-22	2001-06-28	Basf Ag	Verfahren zur Reinigung von Kreatin
AU2003273939A1 (en) *	2002-10-04	2004-04-23	Flexsys B.V.	Process for the synthesis of guanidine derivatives
DE10331481A1 (de) *	2003-07-11	2005-02-24	Degussa Ag	Verfahren zur Reduzierung der Formaldehyd- und Cyanid-Gehalte in Lösungen von Sarkosinsalzen
DE102006016227A1 (de) *	2006-04-06	2007-10-11	Degussa Gmbh	Verfahren zur Herstellung von Kreatin, Kreatin-Monohydrat oder Guanidinoessigsäure
CN101434563B (zh) *	2008-12-15	2011-06-22	太仓市新毛涤纶化工有限公司	肌酸一水物的制备方法
CN102329249A (zh) *	2011-07-22	2012-01-25	周彬	胍基丙酸的化学合成方法
CN104080448B (zh) *	2011-11-10	2018-02-13	西泽广久	肌酸组合物的摄取方法及在该摄取方法中使用的肌酸组合物以及使用所述肌酸组合物制成的含肌酸的药剂及食品
WO2014121648A1 (zh) *	2013-02-05	2014-08-14	江苏远洋药业股份有限公司	一种肌酸的合成方法
CN104086461B (zh) *	2014-07-07	2016-02-24	上海宝穗化工有限公司	一水肌酸的制备方法
CN107721882A (zh) *	2016-08-11	2018-02-23	宁夏天成生化科技有限公司	一种n‑甲基胍基丙酸的制备方法
CN106831495A (zh) *	2016-12-28	2017-06-13	安徽省虹升生物股份有限公司	一种一水肌酸的化工合成方法
CN110596269B (zh) *	2019-09-20	2022-03-04	汤臣倍健股份有限公司	一种同时检测肌酸粉中多种成分的含量测定方法
DK4208436T3 (da) *	2020-09-01	2024-07-22	Evonik Operations Gmbh	Fremgangsmåde til fremstilling af guanidinoeddikesyre
CN115322122A (zh) *	2022-09-14	2022-11-11	宁夏太康药业有限公司	一种肌氨酸螯合钙水溶液制备一水肌酸的方法
CN116041226B (zh) *	2022-12-16	2024-06-11	山东阳谷华泰化工股份有限公司	一种连续合成一水肌酸的方法
EP4455123A1 (en) *	2023-09-20	2024-10-30	Qiangjiang Yongan Pharmaceutical Co., Ltd.	Novel preparation method for sarcosine and derivatives thereof
CN119039182A (zh) *	2024-08-15	2024-11-29	河北博泽化工有限责任公司	一种连续生产高纯度一水肌酸的制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE494918C (de) *	1926-10-29	1930-03-31	Schering Kahlbaum Akt Ges	Verfahren zur Darstellung von Guanidinen
US1967400A (en) *	1930-03-27	1934-07-24	Schering Kahlbaum Ag	Production of guanidino fatty acids
US2574510A (en) *	1947-02-04	1951-11-13	American Cyanamid Co	Cationic surface active agents and method of preparation
US2654779A (en) *	1950-12-23	1953-10-06	Int Minerals & Chem Corp	Method of preparation of guanidino fatty acids
US2620354A (en) *	1951-01-12	1952-12-02	Int Minerals & Chem Corp	Production of guanidino fatty acids
CH401989A (fr) *	1958-09-26	1965-11-15	Kuhlmann Ets	Procédé de préparation de la phosphocréatine
FR1210435A (fr) *	1958-09-26	1960-03-08	Cfmc	Procédé de synthèse de la phosphocréatine
JPS59500B2 (ja) *	1978-06-28	1984-01-07	富郎岩井	クレアチンの製造法
SU1708810A1 (ru) *	1989-10-18	1992-01-30	Ленинградский государственный университет	Сол нокислые соли эфиров гуанидинэнантовой кислоты в качестве гидрофобных анионообменников
EP0646573A1 (en) *	1993-09-30	1995-04-05	Hoechst Aktiengesellschaft	Preparation of protected and unprotected guanidino-substituted carboxylic acids

1995
- 1995-07-18 DE DE19526236A patent/DE19526236A1/de not_active Withdrawn
1996
- 1996-06-26 CZ CZ19961885A patent/CZ290563B6/cs not_active IP Right Cessation
- 1996-06-28 JP JP8169945A patent/JP3056416B2/ja not_active Expired - Fee Related
- 1996-07-09 US US08/677,073 patent/US5719319A/en not_active Expired - Lifetime
- 1996-07-10 CN CN96110631A patent/CN1061647C/zh not_active Expired - Lifetime
- 1996-07-11 CA CA002181026A patent/CA2181026C/en not_active Expired - Lifetime
- 1996-07-17 DE DE59600727T patent/DE59600727D1/de not_active Expired - Lifetime
- 1996-07-17 SI SI9630027T patent/SI0754679T1/xx not_active IP Right Cessation
- 1996-07-17 NO NO962984A patent/NO305200B1/no not_active IP Right Cessation
- 1996-07-17 RU RU96115328/04A patent/RU2163233C2/ru not_active IP Right Cessation
- 1996-07-17 AT AT96111542T patent/ATE172715T1/de active
- 1996-07-17 HU HU9601954A patent/HU218820B/hu not_active IP Right Cessation
- 1996-07-17 ES ES96111542T patent/ES2126355T3/es not_active Expired - Lifetime
- 1996-07-17 PL PL96315319A patent/PL184404B1/pl unknown
- 1996-07-17 EP EP96111542A patent/EP0754679B1/de not_active Expired - Lifetime
- 1996-07-17 DK DK96111542T patent/DK0754679T3/da active
- 1996-07-18 SK SK939-96A patent/SK280544B6/sk not_active IP Right Cessation

Also Published As

Publication number	Publication date
US5719319A (en)	1998-02-17
DE59600727D1 (de)	1998-12-03
JPH0931043A (ja)	1997-02-04
DE19526236A1 (de)	1997-01-23
RU2163233C2 (ru)	2001-02-20
HU218820B (hu)	2000-12-28
ATE172715T1 (de)	1998-11-15
CN1061647C (zh)	2001-02-07
HU9601954D0 (en)	1996-09-30
CA2181026A1 (en)	1997-01-19
HUP9601954A1 (en)	1997-05-28
JP3056416B2 (ja)	2000-06-26
CZ290563B6 (cs)	2002-08-14
NO962984D0 (no)	1996-07-17
NO305200B1 (no)	1999-04-19
PL184404B1 (pl)	2002-10-31
NO962984L (no)	1997-01-20
EP0754679B1 (de)	1998-10-28
SK93996A3 (en)	1997-03-05
EP0754679A1 (de)	1997-01-22
SI0754679T1 (en)	1998-12-31
ES2126355T3 (es)	1999-03-16
PL315319A1 (en)	1997-01-20
HUP9601954A3 (en)	1998-07-28
CZ188596A3 (en)	1997-02-12
DK0754679T3 (da)	1999-07-12
CA2181026C (en)	2004-04-27
CN1140707A (zh)	1997-01-22

Legal Events

Date	Code	Title	Description
2011-04-05	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20100718

Publication	Publication Date	Title
US5719319A (en)	1998-02-17	Process for the preparation of a creatine or creatine monohydrate
US6326513B1 (en)	2001-12-04	Process for producing creatine or creatine-monohydrate
US3539629A (en)	1970-11-10	Process for producing tetraacetyl derivatives of diamines
CA1299584C (en)	1992-04-28	Process for producing 1,6-di(n -cyano-n -guanidino) hexane
US6509497B1 (en)	2003-01-21	Process for preparing guanidine derivatives
US6143929A (en)	2000-11-07	Process for preparing guanidine derivatives
US6147258A (en)	2000-11-14	Preparation of substituted guanidine derivatives
US5672702A (en)	1997-09-30	Process for preparing 3 amino 1, 2, 4-benzotriazine dioxide
EP0343597B1 (en)	1993-03-03	Preparation of tris (2-cyanoethyl) amine
US4929727A (en)	1990-05-29	Improved process for precipitating cytosine from alkaline solutions with sulfuric acid
CN121064108B (zh)	2026-03-27	一种2-氨基苯并咪唑的制备方法
SU532340A3 (ru)	1976-10-15	Способ получени 3-(5нитро-1-метил2-имидазолил)- -триазоло(4,3-в) пиридазинов или их солей
US4476306A (en)	1984-10-09	Method of preparing 2,4-dihydroxypyrimidine
US5097030A (en)	1992-03-17	Process for the preparation of 2-(methylthio)barbituric acid
SU1641815A1 (ru)	1991-04-15	Способ получени метилового эфира изоциануровой кислоты
SU1432059A1 (ru)	1988-10-23	Способ получени транс-1,4,5,8-тетраазадекалина
CN111333664A (zh)	2020-06-26	生物素交联剂、应用及其制备方法
WO1998022450A1 (en)	1998-05-28	Process for the preparation of 2-imino-5-phenyl-4-oxazolidinone and its intermediates
JPH05132468A (ja)	1993-05-28	５−／／４−／（４′，６′−ジメチル−２−ピリミジニル）スルフアモイル／フエニル／アゾ／アセチルサリチル酸およびその製造方法
JPS6121472B2 (cs)	1986-05-27
Studentsov et al.	1971	The synthesis of xanthine-8-acetic acid and some of its derivatives
JPH0138103B2 (cs)	1989-08-11
CS257248B1 (cs)	1988-04-15	Způsob výroby 2-(2'-furyl )-benzimidazolu
JPH0335308B2 (cs)	1991-05-27
PL136596B2 (en)	1986-03-31	Process for preparing novel 2,7-dibromo-10-carboxymethyl-acridone