HU210115B - Process for prepg. metoclopramid-hydroclorid solutions for peroral use - Google Patents

Process for prepg. metoclopramid-hydroclorid solutions for peroral use Download PDF

Info

Publication number: HU210115B
Authority: HU; Hungary
Prior art keywords: hydrochloride; solution; metoclopramide; solutions; weight
Prior art date: 1990-09-28

Application number

HU912896A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT58514A (en

Inventor

Rainhardt Klimek

Ingo Bonnacker

Berthold Stemmle

Original Assignee

Kali Chemie Pharma Gmbh

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.)

1990-09-28

Filing date

1991-09-09

Publication date

1995-02-28

1991-09-09 Application filed by Kali Chemie Pharma Gmbh filed Critical Kali Chemie Pharma Gmbh

1992-03-30 Publication of HUT58514A publication Critical patent/HUT58514A/hu

1995-02-28 Publication of HU210115B publication Critical patent/HU210115B/hu

Links

238000000034 method Methods 0.000 title claims description 8
TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 24
230000002335 preservative effect Effects 0.000 claims description 12
229960000923 metoclopramide hydrochloride Drugs 0.000 claims description 11
239000003755 preservative agent Substances 0.000 claims description 11
239000003765 sweetening agent Substances 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
235000003599 food sweetener Nutrition 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000004097 EU approved flavor enhancer Substances 0.000 claims description 4
235000013355 food flavoring agent Nutrition 0.000 claims description 4
235000019264 food flavour enhancer Nutrition 0.000 claims description 4
239000005454 flavour additive Substances 0.000 claims description 3
230000000813 microbial effect Effects 0.000 claims description 3
229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
IRQVJPHZDYMXNW-UHFFFAOYSA-N metoclopramide dihydrochloride monohydrate Chemical compound O.[Cl-].[Cl-].CC[NH+](CC)CCNC(=O)C1=CC(Cl)=C([NH3+])C=C1OC IRQVJPHZDYMXNW-UHFFFAOYSA-N 0.000 claims 2
239000012535 impurity Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 35
229960004503 metoclopramide Drugs 0.000 description 15
RVFUNJWWXKCWNS-UHFFFAOYSA-N 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxybenzamide;hydrochloride Chemical compound Cl.CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC RVFUNJWWXKCWNS-UHFFFAOYSA-N 0.000 description 11
244000005700 microbiome Species 0.000 description 10
239000000203 mixture Substances 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229920001817 Agar Polymers 0.000 description 7
239000008272 agar Substances 0.000 description 7
244000052616 bacterial pathogen Species 0.000 description 7
240000004808 Saccharomyces cerevisiae Species 0.000 description 6
239000003814 drug Substances 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
241000233866 Fungi Species 0.000 description 5
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 4
239000001888 Peptone Substances 0.000 description 4
108010080698 Peptones Proteins 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000002054 inoculum Substances 0.000 description 4
235000019319 peptone Nutrition 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
229960001462 sodium cyclamate Drugs 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
235000010199 sorbic acid Nutrition 0.000 description 3
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 2
241000228245 Aspergillus niger Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
241000222122 Candida albicans Species 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
230000003474 anti-emetic effect Effects 0.000 description 2
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 description 2
229910052791 calcium Inorganic materials 0.000 description 2
230000001332 colony forming effect Effects 0.000 description 2
238000011109 contamination Methods 0.000 description 2
239000012470 diluted sample Substances 0.000 description 2
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
229940126601 medicinal product Drugs 0.000 description 2
239000012569 microbial contaminant Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
229940085605 saccharin sodium Drugs 0.000 description 2
239000004334 sorbic acid Substances 0.000 description 2
229940075582 sorbic acid Drugs 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000021092 sugar substitutes Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000012085 test solution Substances 0.000 description 2
NVKQKAZYUPPRJX-UHFFFAOYSA-N 1,3,5-tribromo-2-(2,5-dibromophenyl)benzene Chemical compound BrC1=CC=C(Br)C(C=2C(=CC(Br)=CC=2Br)Br)=C1 NVKQKAZYUPPRJX-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
244000303258 Annona diversifolia Species 0.000 description 1
235000002198 Annona diversifolia Nutrition 0.000 description 1
108010011485 Aspartame Proteins 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000588921 Enterobacteriaceae Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
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 1
229930195725 Mannitol Natural products 0.000 description 1
-1 PHB esters Chemical class 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241001103617 Pseudomonas aeruginosa ATCC 15442 Species 0.000 description 1
101100519432 Rattus norvegicus Pdzd2 gene Proteins 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
239000000605 aspartame Substances 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
229960003438 aspartame Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 1
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 1
235000013361 beverage Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229940043202 calcium cyclamate Drugs 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
230000001408 fungistatic effect Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
239000007959 natural flavoring substance Substances 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
239000003186 pharmaceutical solution Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000004321 preservation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108010009004 proteose-peptone Proteins 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU912896A 1990-09-28 1991-09-09 Process for prepg. metoclopramid-hydroclorid solutions for peroral use HU210115B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4030735		1990-09-28

Publications (2)

Publication Number	Publication Date
HUT58514A HUT58514A (en)	1992-03-30
HU210115B true HU210115B (en)	1995-02-28

Family

ID=6415188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU912896A HU210115B (en)	1990-09-28	1991-09-09	Process for prepg. metoclopramid-hydroclorid solutions for peroral use

Country Status (4)

Country	Link
AT (1)	AT404796B (de)
CH (1)	CH681690A5 (de)
CZ (1)	CZ280606B6 (de)
HU (1)	HU210115B (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6770262B2 (en)	2000-03-30	2004-08-03	Questcor Pharmaceuticals, Inc.	Nasal administration of agents for the treatment of gastroparesis
US8334281B2 (en)	2008-12-22	2012-12-18	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11020361B2 (en)	2008-12-22	2021-06-01	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11517545B2 (en)	2016-12-15	2022-12-06	Evoke Pharma, Inc.	Treatment of moderate and severe gastroparesis

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1525M (fr) *	1961-07-25	1962-11-16	Ile De France	Médicaments antiémétiques nouveaux.
GB8412585D0 (en) *	1984-05-17	1984-06-20	Beecham Group Plc	Composition
US4624965A (en) *	1984-11-15	1986-11-25	Nastech Pharmaceutical Co., Inc.	Novel method of administering anti-nausea and anti-emetic pharmaceutical agents and novel dosage forms containing same

1991
- 1991-08-22 CH CH2467/91A patent/CH681690A5/de not_active IP Right Cessation
- 1991-09-09 HU HU912896A patent/HU210115B/hu not_active IP Right Cessation
- 1991-09-26 AT AT0193891A patent/AT404796B/de not_active IP Right Cessation
- 1991-09-27 CZ CS912963A patent/CZ280606B6/cs not_active IP Right Cessation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6770262B2 (en)	2000-03-30	2004-08-03	Questcor Pharmaceuticals, Inc.	Nasal administration of agents for the treatment of gastroparesis
US8334281B2 (en)	2008-12-22	2012-12-18	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11020361B2 (en)	2008-12-22	2021-06-01	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11628150B2 (en)	2008-12-22	2023-04-18	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11813231B2 (en)	2008-12-22	2023-11-14	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US12194008B2 (en)	2008-12-22	2025-01-14	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US12194009B2 (en)	2008-12-22	2025-01-14	Evoke Pharma, Inc.	Nasal formulations of metoclopramide
US11517545B2 (en)	2016-12-15	2022-12-06	Evoke Pharma, Inc.	Treatment of moderate and severe gastroparesis
US12377064B2 (en)	2016-12-15	2025-08-05	Evoke Pharma, Inc.	Treatment of moderate and severe gastroparesis

Also Published As

Publication number	Publication date
ATA193891A (de)	1998-07-15
CH681690A5 (en)	1993-05-14
CZ280606B6 (cs)	1996-03-13
AT404796B (de)	1999-02-25
CS296391A3 (en)	1992-04-15
HUT58514A (en)	1992-03-30

Legal Events

Date	Code	Title	Description
2010-06-28	MM4A	Lapse of definitive patent protection due to non-payment of fees

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