WO1988002993A1 - Process for producing effervescent granulates, effervescent granulates thus produced and their use - Google Patents
Process for producing effervescent granulates, effervescent granulates thus produced and their use Download PDFInfo
- Publication number
- WO1988002993A1 WO1988002993A1 PCT/EP1987/000618 EP8700618W WO8802993A1 WO 1988002993 A1 WO1988002993 A1 WO 1988002993A1 EP 8700618 W EP8700618 W EP 8700618W WO 8802993 A1 WO8802993 A1 WO 8802993A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- reaction
- coating
- carnitine
- effervescent
- Prior art date
Links
- 239000008187 granular material Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 11
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000013078 crystal Substances 0.000 claims abstract description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000007524 organic acids Chemical class 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 8
- 238000000576 coating method Methods 0.000 claims abstract 8
- -1 alkaline earth metal carbonate Chemical class 0.000 claims abstract 7
- 239000011248 coating agent Substances 0.000 claims abstract 7
- 239000011247 coating layer Substances 0.000 claims abstract 7
- 239000007787 solid Substances 0.000 claims abstract 4
- 239000010410 layer Substances 0.000 claims abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000007864 aqueous solution Substances 0.000 claims abstract 2
- 238000002156 mixing Methods 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- 239000002344 surface layer Substances 0.000 claims abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007938 effervescent tablet Substances 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000003826 tablet Substances 0.000 description 5
- 229960004203 carnitine Drugs 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000001354 calcium citrate Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- OWFJMGQSOHDIPP-UHFFFAOYSA-L monocalcium citrate Chemical compound [Ca+2].OC(=O)CC(O)(C(O)=O)CC([O-])=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O OWFJMGQSOHDIPP-UHFFFAOYSA-L 0.000 description 2
- 235000012663 monocalcium citrate Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Classifications
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/40—Effervescence-generating compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
Definitions
- the invention relates to a method for producing a shower granulate according to the preamble of the claim
- L-carnitine which plays an important role in human metabolism, to effervescent granules has hitherto not been practical because of the strong hygroscopicity of this substance been at.
- L-carnitine fulfills an essential function for the utilization of fatty acids and for the transport of metabolic energy.
- the betaine character i.e. the formation of an inner salt between the positively charged nitrogen and the negatively charged COO group in carnitine is the reason for its reactivity with acids and its strong hygroscopicity.
- the commercially available pharmaceutical carnitine preparations therefore mix carnitine with inert substances in order to prevent the possible reactions.
- Inert substances have also mainly been proposed for tableting. High doses, e.g. Oral administration of about 1 g of carnitine in the form of a tablet or a capsule is hardly possible due to the volume.
- a dilution of sugar, carbohydrates and other inert substances for the purpose of creating a basis for the preparation of a drinking solution also results in excessive overall volumes and weights. This basis is not acceptable in terms of taste and is not rational.
- the invention is therefore based on the object p , despite the acid reactivity of L-carnitine, to produce stable forms of administration with organic acids which are temperature-stable and not very hygroscopic, but which dissolve quickly in water.
- a buffer solution of mono-calcium citrate is used in concentrated form, then it is possible to bind larger amounts of anhydrous sodium carbonate to the surface of the citric acid crystals without the sodium carbonate being able to absorb water of crystallization.
- the installation of crystal water in sodium carbonate takes a long time, and on the other hand, the installation of crystal water is hindered by the concentrated solution of mono-calcium citrate.
- Particle granulation of the surfaces of citric acid crystals and subsequent application of anhydrous sodium carbonate can thus be used to produce particles which, even when pressed into tablets, have an externally alkaline reaction, but which dissolve rapidly on contact with water.
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Glanulating (AREA)
- Soy Sauces And Products Related Thereto (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE8787907312T DE3767473D1 (de) | 1986-10-22 | 1987-10-21 | Verfahren zum herstellen eines brausegranulates, danach hergestelltes brausegranulat sowie dessen verwendung. |
| AT87907312T ATE59943T1 (de) | 1986-10-22 | 1987-10-21 | Verfahren zum herstellen eines brausegranulates, danach hergestelltes brausegranulat sowie dessen verwendung. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3635864.9 | 1986-10-22 | ||
| DE19863635864 DE3635864A1 (de) | 1986-06-26 | 1986-10-22 | Verfahren zum herstellen eines brausegranulates, danach hergestelltes brausegranulat sowie dessen verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1988002993A1 true WO1988002993A1 (en) | 1988-05-05 |
Family
ID=6312198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1987/000618 WO1988002993A1 (en) | 1986-10-22 | 1987-10-21 | Process for producing effervescent granulates, effervescent granulates thus produced and their use |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2037758B1 (en) | 2006-07-12 | 2018-09-19 | PURAC Biochem BV | Partially neutralized acid coated food-grade particles |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3627475A1 (de) * | 1986-06-26 | 1988-01-14 | Gergely Gerhard | Verfahren zum herstellen eines brausegranulates, danach hergestelltes brausegranulat sowie dessen verwendung |
| DE4027927A1 (de) * | 1990-09-04 | 1992-03-05 | Bayer Ag | Brausekomponente und verfahren zu ihrer herstellung |
| DE4290300T1 (de) * | 1991-01-30 | 1993-10-07 | Wellcome Found | Wasserdispergierbare Tabletten |
| US5629016A (en) * | 1991-01-30 | 1997-05-13 | Glaxo Wellcome Inc. | Water-dispersible tablets |
| GB9215908D0 (en) * | 1992-07-27 | 1992-09-09 | Wellcome Found | Water dispersible tablets |
| US5698226A (en) * | 1993-07-13 | 1997-12-16 | Glaxo Wellcome Inc. | Water-dispersible tablets |
| US5560928A (en) * | 1995-06-23 | 1996-10-01 | Defelice; Stephen L. | Nutritional and/or dietary composition and method of using the same |
| US6974595B1 (en) * | 1996-05-17 | 2005-12-13 | Proethic Pharmaceuticals, Inc. | Pharmaceutical compositions based on Diclofenae |
| US5997901A (en) * | 1998-10-22 | 1999-12-07 | Mills; Robert G. | Method of manufacturing scented molded products |
| AT407111B (de) * | 1998-12-22 | 2000-12-27 | Gergely Dr & Co | Zucker- und/oder zuckeralkoholhältiges matrixmaterial und verfahren zu seiner herstellung |
| GR1006148B (el) * | 2007-12-07 | 2008-11-10 | Uni-Pharma Κλεων Τσετης, Φαρμακευτικα Εργαστηρια Αβεε | Αναβραζοντα δισκια και αναβραζοντα κοκκια που περιεχουν τρυγικη καρνιτινη |
| AU2009356961B2 (en) * | 2009-12-14 | 2016-05-19 | Jubilent Global Limited | Effervescent L-carnitine-based composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359119A (en) * | 1964-03-27 | 1967-12-19 | Reynolds Tobacco Co R | Method of preparing an agglomerated food product |
| DE3149517A1 (de) * | 1980-12-15 | 1982-07-22 | Gerhard Dr.-Ing. 1050 Wien Gergely | Verfahren und vorrichtung zum granulieren eines pulvergemisches |
| FR2552308A1 (fr) * | 1983-09-28 | 1985-03-29 | Gergely Gerhard | Melange effervescent convenant en particulier pour des comprimes effervescents, comprimes effervescents prepares a l'aide de ce melange et procede pour sa preparation |
| US4602039A (en) * | 1983-12-28 | 1986-07-22 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Salts of-carnitine and alkanoyl L-carnitines and process for preparing same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2784100A (en) * | 1955-03-01 | 1957-03-05 | Abbott Lab | Calcium cyclamate tablet and process of making the same |
| US3480185A (en) * | 1966-06-20 | 1969-11-25 | Johnson & Johnson | Charged effervescing agent and medicament dispensing metering valve-actuated aerosol container producing a dose of medicament and carbonation in water |
| US3653914A (en) * | 1970-03-20 | 1972-04-04 | Alberto Culver Co | Production of tablets |
| IT1133010B (it) * | 1980-05-15 | 1986-07-09 | Sigma Tau Ind Farmaceuti | Metodo terapuetico per il trattamento del diabete mellito a insorgenza giovanile e composizione farmaceutica per tale metodo |
| EP0076340B1 (de) * | 1981-10-06 | 1984-08-15 | Gerhard Dr. Gergely | Verfahren zur Herstellung von gewünschtenfalls zu Brausetabletten verarbeitbaren Brausegranulaten |
| US4687782A (en) * | 1984-12-10 | 1987-08-18 | Nutri-Fuels Systems, Inc. | Nutritional composition for enhancing skeletal muscle adaptation to exercise training |
| IT1177384B (it) * | 1984-12-12 | 1987-08-26 | Boeehringer Biochemia Robin Sp | Prodotti dietetici granulari a base di amminoacidi e procedimento per la loro preparazione |
-
1986
- 1986-10-22 DE DE19863635864 patent/DE3635864A1/de active Granted
-
1987
- 1987-10-21 US US07/221,788 patent/US4968517A/en not_active Expired - Lifetime
- 1987-10-21 AT AT87907312T patent/ATE59943T1/de not_active IP Right Cessation
- 1987-10-21 AU AU81739/87A patent/AU8173987A/en not_active Abandoned
- 1987-10-21 EP EP87907312A patent/EP0287647B1/de not_active Expired - Lifetime
- 1987-10-21 WO PCT/EP1987/000618 patent/WO1988002993A1/de active IP Right Grant
- 1987-10-21 DE DE8787907312T patent/DE3767473D1/de not_active Expired - Fee Related
- 1987-10-22 CA CA000550012A patent/CA1302148C/en not_active Expired - Lifetime
- 1987-10-22 PT PT85972A patent/PT85972B/pt not_active IP Right Cessation
- 1987-10-22 ES ES8703024A patent/ES2008285A6/es not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359119A (en) * | 1964-03-27 | 1967-12-19 | Reynolds Tobacco Co R | Method of preparing an agglomerated food product |
| DE3149517A1 (de) * | 1980-12-15 | 1982-07-22 | Gerhard Dr.-Ing. 1050 Wien Gergely | Verfahren und vorrichtung zum granulieren eines pulvergemisches |
| FR2552308A1 (fr) * | 1983-09-28 | 1985-03-29 | Gergely Gerhard | Melange effervescent convenant en particulier pour des comprimes effervescents, comprimes effervescents prepares a l'aide de ce melange et procede pour sa preparation |
| US4602039A (en) * | 1983-12-28 | 1986-07-22 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Salts of-carnitine and alkanoyl L-carnitines and process for preparing same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2037758B1 (en) | 2006-07-12 | 2018-09-19 | PURAC Biochem BV | Partially neutralized acid coated food-grade particles |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0287647B1 (de) | 1991-01-16 |
| PT85972B (pt) | 1990-07-31 |
| ES2008285A6 (es) | 1989-07-16 |
| US4968517A (en) | 1990-11-06 |
| CA1302148C (en) | 1992-06-02 |
| DE3767473D1 (de) | 1991-02-21 |
| DE3635864A1 (de) | 1988-05-05 |
| ATE59943T1 (de) | 1991-02-15 |
| AU8173987A (en) | 1988-05-25 |
| DE3635864C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-04-06 |
| PT85972A (de) | 1987-11-01 |
| EP0287647A1 (de) | 1988-10-26 |
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