GB2083749A - Drug combination comprising ambroxol and an antibiotic for the treatment of infectious diseases of the respiratory tract - Google Patents
Drug combination comprising ambroxol and an antibiotic for the treatment of infectious diseases of the respiratory tract Download PDFInfo
- Publication number
- GB2083749A GB2083749A GB8127983A GB8127983A GB2083749A GB 2083749 A GB2083749 A GB 2083749A GB 8127983 A GB8127983 A GB 8127983A GB 8127983 A GB8127983 A GB 8127983A GB 2083749 A GB2083749 A GB 2083749A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- compositions
- antibiotic
- trans
- dibromo
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
Abstract
Pharmaceutical compositions comprising, in combination, an antibiotic or a physiologically acceptable salt thereof and trans-4-[(2-amino-3,5- dibromo-benzyl)-amino]cyclohexanol or a physiologically acceptable acid addition salt thereof (e.g. the hydrochloride, ambroxol), optionally in association with a pharmaceutical carrier or excipient for use in combating bacterial infections of the respiratory tract. The antibiotic is preferably erythromycin, doxycycline, oxytetracycline, chloramphenicol, cephalexin, ampicillin or amoxycillin.
Description
SPECIFICATION
Drug combination for the treatment of infectious diseases of the respiratory tract
British Patent Specification No. 1178034 describes the compound trans-4[(2-amino-3,5-dibrnmobenzyl).
amino]cyclohexanol and physiologically acceptable acid addition salts thereof with inorganic or organic acids, which have expectorant properties. These compounds, and particularly the hydrochloride (generic rrame: ambroxol), are therefore used for the treatment of acute and chronic diseases of the respiratory tract which are accompanied by pathological changes in secretion. They are used especially in intensive medicine for preventing pulmonary complications.
- Antibiotics such as, for example, erythromycin, doxycycline, oxytetracycline, chloramphenicol, cephalexin, ampicillin and amoxicillin, have also proved effective in combating bacterial diseases of the respiratory tract.
Surprisingly, we have now found that the simultaneous administration of an antibiotic or a salt thereof and trans-4-[(2-amino-3,5-dibromobenzyl)-amino]cyclohexanol or a physiologically acceptable acid addition salt thereof increases the bronchopulmonary antibiotic concentrations of the antibiotic used by more than 20%.
The levels of antibiotic activity which can be obtained with this new combination thus permit successful treatment even with severe, acute clinical cases. However, a particularly important point is that, even when the acute stage of the disease has passed and the dosage of antibiotics is relatively low, sufficiently high levels of antibiotic activity can be maintained in the bronchopulmonary region, so that relapses are extremely rare.
This invention thus relates to pharmaceutical compositions comprising, in combination, an antibiotic or a physiologically acceptable salt thereof and trans.4-[2-amino-3,5-dibromobenzyl)amino]cyclohexanol or a physiologically acceptable acid addition salt thereof, optionally in association with a pharmaceutical carrier or excipient. The compositions according to the invention may be used for the treatment of infectious diseases of the respiratory tract.
The antibiotics in question are, in particular, those which are suitable for combating bacterial diseases of the respiratory tract, e.g. erythromycin, doxycycline, cephalexin, ampicillin and amoxicillin.
By way of example, the effect of trans-4-[(2-amino-3,5-dibrnmobenzyl)aminojcyclohexanol hydrochloride (ambroxol) on the bronchopulmonary antibiotic concentrations of ampicillin, erythromycin and amoxicillin was investigated as follows:
All the substances were administered, in a single dose, to Wistar rats weighing between 300 and 400 g, by oesophageal tube. The dosage of antibiotics tested was 50 mg/kg in each case, whilst the dosage of ambroxol was 10 mg/kg. The rats were fed with Cargill Dieta R-R pellets and water and the animals were kept under test conditions at a temperature of between 20 and 24"C.
Groups of 20 rats were treated with the antibiotic to be tested and ambroxol, in comparison with a control group (same antibiotic but no ambroxol). The animals were killed 90 minutes after the administration of the test substances and both lungs were removed. The lungs were homogenised and centrifuged at 5000 r.p.m.
The concentration of antibiotic was determined microbiologically in the supernatant portion.
The addition of ambroxol caused the antibiotic levels measured to rise as follows:
ampicillin + 23%
erythromycin + 27%
amoxicillin + 27%
It should also be mentioned that the active substances used according to the invention are practically non-toxic; in the mouse, the LDs0 of the active substances are as follows:
ambroxol 2,720 mg/kg p.o.,
doxycycline 1,650 mg/kg p.o.,
cephalexin 1,600-6,200 mg/kg p.o.,
ampicillin 3,340 mg/kg p.o.,
erythromycin 3,000 mg/kg p.o. and
amoxycillin 1,000 mg/kg p.o.
The compositions according to the invention may be administered, in adults, 1 to 4 times daily, generally as a single dose of from 100 to 750 mg of antibiotic or physiologically acceptable salt thereof + 2 to 100 mg, preferably 7.5 to 75 mg oftrans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol of physiologically acceptable acid addition salt thereof. The daily dose is thus generally 0.1 to 3.0 g of antibiotic or physiologically acceptable salt thereof + 7.5 to 150 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)amino]cyclohexanol or physiologically acceptable acid addition salt thereof. The children's dose is normally one quarter to one half that of the adult dose.
In adults, the single doses for the drug combinations according to the invention are, for example, as follows: combination of ambroxol/doxycycline: about 75 mg of ambroxol + about 100 mg of doxycycline once a day (but double the dose on the first day of treatment), combination of ambroxol/cephalexin: 15 to 30 mg of ambroxol + 250 to 500 mg of cephalexin 2 to 4 times daily, combination of ambroxol/ampicillin: 15 to 30 mg of ambroxol + 250 to 500 mg of ampicillin 2 to 4times daily, combination of ambroxol/erythromycin: 15 to 30 mg of ambroxol + 300 to 600 mg of erythromycin 2 to 4 times daily, combination of ambroxol/amoxicillin: 15 to 30 mg of ambroxol + 500 to 750 mg of amoxicillin 2 to 4 times daily.
For pharmaceutical use, the compositions according to the invention may be made into the usual galenic preparations such as e.g. plain tablets, film-coated tablets, oblong tablets, coated tablets or capsules and delayed release forms, ampoules, dry ampoules, dry granules or dry syrups, using conventional galenic excipients such as e.g. lactose, mannitol, corn starch, methylcellulose, hydroxyethylcellulose, polyethylene oxide, finely dispersed aluminium oxide, magnesium aluminium silicate, magnesium oxide, magnesium stearate, sodium laurylsulphate, sodium citrate, tartaric acid, sodium pyrosulphite, dioctyl sodium sulphosuccinate, sodium salt of methyl p-hydroxybenzoate, sodium salt of propyl p-hydroxybenzoate, sodium saccharin, flavourings and defoaming agents.
The following non-limiting Examples are intended to illustrate the invention:
EXAMPLE 1 Film-coated tablets containing 30 mg of ambroxol to 500 mg ofcephalexin Composition:
1 film-coated tablet contains:
ambroxol 30.0 mg
cephalexin 500.0 mg
lactose 100.0 mg
dried corn starch 80.0 mg
polyvinyl pyrrolidone 16.0 mg
magnesium stearate 4.0 mg
730.0 mg
Preparation
The first four ingredients are mixed together and moistened with a 10% solution of the polyvinyl pyrrolidone in 70% ethanol. The moist mixture is passed through a screen with a mesh size of 1.5 mm, then dried and passed through the same screen again. The magnesium stearate is then added and tablets are produced from the mixture using a tablet press.
Coating
A coating consisting of a solution of ethylcellulose in ethanol is applied to the tablets. The weight is increased by 1.5% by this film coating.
- Weight of tablets: 730 mg
Punch: 13 mm.
EXAMPLE 2
Dry granulate forsyrup containing 15 mg ofambroxol + 250 mg ofcephalexin per 5 my Composition:
5 ml contain:
ambroxol 15.0 mg
cephalexin 250.0 mg
sodium citrate 50.0 mg
dioctyl sodium sulphosuccinate 1.0 mg
polyvinyl pyrrolidone 50.0 mg
magnesium aluminium silicate 10.0 mg
sodium saccharin 5.0 mg
sodium salt of methyl p-hydroxy
benzoate 6.0 mg sodium salt of propyl p-hydroxy
benzoate 1.5 mg powdered flavouring 10.0 mg
silicon defoaming agent 0.25 mg
mannitol ad 2.0 g
Method ofpreparation: Granulate solution: Dioctyl sodium sulphosuccinate, silicon defoaming agent and some of the
polyvinyl pyrrolidone are dissolved or dispersed in sufficient water for the
granulation.
Mixture ofpowders: All the remaining components, with the exception of the flavouring, are
homogeneously mixed.
Granulation: The mixture of powders is homogeneously moistened with the granulation
liquid. The moist mixture is screened through a mesh with a maximum size of 2
mm, then dried and screened again.
Final mixture: The flavouring is added to the granulate and homogeneously distributed
therein.
40 g of granulate + 75 ml of water yield about 100 ml of syrup ready for use.
5 ml ( 1 dose) contain 15 mg of ambroxol and 250mg of cephalexin.
EXAMPLE 3
EXAMPLE 3
Dry granulate for drop suspension containing 15 mg ofambroxol + 250 mg ofcephalexin per I ml
1 mi contains:
ambroxol 15.0 mg cephaiexin 250.0 mg
sodium citrate 30.0 mg
methyl cellulose 2.0 mg
polyethylene oxide 2.0 mg
sodium salt of methyl p-hydroxy
benzoate 1.2 mg
sodium salt of propyl p-hydroxy
benzoate 0.3 mg
powdered flavouring 3.0 mg
silicon defoaming agent 0.05 mg
powdered sugar ad 0.4 g
Method ofpreparation: Granulate solution: Polyethylene oxide, silicon defoaming agent and some of the methylceilulose
are dissolved or dispersed in sufficient water for the granulation. The
preparation process is continued as in Example 2.
40 g of granulate + 75 ml of water yield about 100 ml of drop suspension ready for use.
1 ml (~ 1 dose) contains 15 mg of ambroxol and 250 mg of cephalexin.
EXAMPLE 4
Oblong tablets containing 15 mg ofambroxol + 500 mg ofampiclllin 1 tablet contains:
ambroxol 15.0 mg
ampicillin 500.0 mg
powdered lactose 380.0 mg
dried corn starch 180.0 mg
polyvinyl pyrrolidone 21.0 mg
magnesium stearate 4.0 mg
1,100.0 mg
Preparation:
The first four ingredients are mixed together and moistened with a 10% solution of polyvinyl pyrrolidone in 70% ethanol. The moist mixture is further treated as in Example 1.
Weight of tablets: 1,100 mg
Shape: 8 x 17mm oblong.
EXAMPLE 5
Ampoules containing 15 mg ofambroxol + 500 mg of ampicillin per 5 ml
1 ampoule of solution contains:
ambroxol 15.0 mg
sodium hydroxide solution 2.5 mg
tartaric acid 5.0 mg
polyethylene oxide 75.0 mg Waterforinjection ad 5 ml
Dry ampoule:
Sodium ampicillin 500.0 mg
Preparation:
The ambroxol and tartaric acid are dissolved, then the polyethylene oxide is dissolved, with stirring, and adjusted to pH 4.0 with sodium hydroxide solution. The solution is sterilised by filtration through membrane filters, transferred into ampoules and sterilised by filtration at 120 C for 10 minutes.
EXAMPLE 6
Ampoules containing 75 mg ofambroxol + 100 mg of doxycycline per 5 ml
1 ampoule contains:
doxycycline hydrochloride 100.0 mg
ambroxol 75.0 mg
magnesium oxide 9.1 mg
sodium pyrosulphite 500.0 mg
polyethylene oxide 500.0 mg Waterforinjection ad 5 ml
Preparation:
The substances are dissolved in the water one after the other and filtered through membrane filters. As the solution is transferred into ampoules, it is treated with a nitrogen current. The solution cannot be sterilised.
EXAMPLE 7
Capsules containing 75 mg ofambroxol + 100 mg of doxycycline
1 capsule contains:
20% spray pellets, consisting of
-water mixture and active
substance 375.0 mg
starch 50.0 mg
lactose 50.0 mg
highly dispersed silicon dioxide 7.0 mg
magnesium stearate 8.0 mg
490.0 mg
*) the active ingredient is suspended in the melt, heated to 70"C, by means of Ultra-Turrax and is
sprayed in a suitable apparatus.
Preparation:
The mixture is transferred into a suitable automatic capsule-making apparatus fitted with a tablet insertion station, and packaged in size 0 long gelatine capsules together with a coated 6 mm core containing 100 mg of doxycycline and conventional tablet excipients.
Weight of capsule: 490 mg.
EXAMPLE 8
Tablets containing 30 mg ofambroxol + 600 mg oferythromycin 1 tablet contains:
ambroxol 30.0 mg
erythromycin 600.0 mg
powdered lactose 380.0 mg
dried corn starch 265.0 mg
polyvinyl pyrrolidone 21.0 mg
magnesium stearate 4.0 mg
1,300.0 mg
Preparation:
The first four ingredients are mixed together and moistened with a 10% solution of the polyvinyl pyrrplidone in ethanol. The moist mixture is further treated as in Example 1.
Weight of tablets: 1,300 mg
Shape: 8.5 x 18 mm, oblong.
EXAMPLE 9
Children 's tablets containing 7.5 mg ofambroxol + 150 mg oferythromycin 1 tablet contains:
ambroxol 7.5 mg
erythromycin 150.0 mg
powdered lactose 95.0 mg
dried corn starch 66.25 mg
polyvinyl pyrrolidone 5.25 mg
Magnesium stearate 1.0 mg
325.0 mg
Preparation:
The first four ingredients are mixed together and moistened with a 10% solution of the polyvinyl pyrrolidone in ethanol. The moist mixture is further treated as in Example 1.
Weight of tablets: 325 mg
Diameter of punch: 10 mm
EXAMPLE 10
Dry granulate for drop suspensions containing 15 mg of ambroxol + 300 mg oferythromycin per 1 ml
1 ml of drops solution contains:
ambroxol 15.0 mg
erthromycin-base equivalent 300.0 mg
sodium citrate 30.0 mg
sodium lauryl sulphate 1.0 mg
methyl cellulose 2.0 mg
sodium saccharin 1.0 mg
sodium salt of methyl
p-hydroxybenzoate 1.2 mg
sodium salt of propyl
p-hydroxybenzoate 0.3 mg
polyvinyl pyrrolidone 3.0 mg
powdered flavouring 3.0 mg
silicon defoaming agent 0.05 mg
powdered sugar ad 0.4 g
Preparation:
The method of preparation is analogous to that of Example 3.
40 g of granulate + 75 ml of water yield about 100 ml of drop suspension ready for use.
1 ml ( 1 dose) contains 15 mg of ambroxol and 300 mg of erythromycin-base equivalent.
EXAMPLE 11
Dry granulate forsyrup containing 30 mg ofambroxol + 600 mg of erythromycin per 5 ml
5 ml contain:
ambroxol 30.0 mg
erythromycin-base equivalent 600.0 mg
sodium citrate 100.0 mg
hydroxyethyl cellulose 15.0 mg
magnesium aluminium silicate 15.0 mg
aluminium oxide 15.0 mg
sodium saccharin 4.0 mg
sodium salt of methyl p-hydroxybenzoate 6.0 mg
sodium salt of propyl p-hydroxybenzoate 1.5 mg
powdered flavouring 10.0 mg
silicon defoaming agent 0.15 mg
powdered sugar ad 2.0 g
Preparation:
Unlike in Example 2, some of the hydroxyethyl cellulose, instead of polyvinyl pyrrolidone, is dissolved in water together with the silicon defoaming agent. Otherwise, the method of preparation is analogous to
Example2.
40 g of granulate + 75 ml ofwateryield about 100 ml of syrup ready for use.
5 ml (= 1 dose) contain 30 mg of Ambroxol and 600 mg of erythromycin-base equivalent.
EXAMPLE 12
Tablets containing 75 mg ofambroxol + 750 mg ofamoxicillin 1 tablet contains:
ambroxol 15.0 mg
amoxicillin 750.0 mg
lactose 400.0 mg
dried corn starch 305.0 mg
polyvinyl pyrrolidone 25.0 mg
magnesium stearate 5.0 mg
1,500.0 mg
Preparation:
The first four ingredients are mixed together and moistened with a 10% solution of the polyvinyl pyrrolidone in ethanol. The moist mixture is further treated analogously to Example 1.
Weight of tablets: 1,500 mg
Shape: 8 x 17 mm, oblong.
Claims (18)
1. Pharmaceutical compositions comprising, in combination, an antibiotic or a physiologically acceptable salt thereof and trans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol or a physiologically acceptable acid addition salt thereof, optionally in association with a pharmaceutical carrier or excipient.
2. Compositions as claimed in claim 1 wherein the antibiotic or physiologically acceptable salt thereof is suitable for combating bacterial infections of the respiratory tract.
3. Compositions as claimed in claim 2 containing erythromycin, doxycycline, cephalexin, ampicillin or amoxicillin as the antibiotic.
4. Compositions as claimed in any preceding claim in the form of dosage units.
5. Compositions as claimed in claim 4wherein each dosage unit contains from 100 to 750 mg of the antibiotic or physiologically acceptable salt thereof.
6. Compositions as claimed in claim 4 or claim 5 wherein each dosage unit contains from 2 to 100 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)-aminojcyclohexanol or a physiologically acceptable acid addition salt thereof.
7. Compositions as claimed in claim 6 wherein each dosage unit contains from 7.5 to 75 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol or a physicologically acceptable acid addition salt thereof.
8. Compositions as claimed in claim 7 wherein each dosage unit contains about 75 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol hydrochloride and about 100 mg of doxycycline.
9. Compositions as claimed in claim 7 wherein each dosage unit contains 15 to 30 mg of trans-4-[2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol hydrochloride and 250 to 500 mg of cephalexin.
10. Compositions as claimed in claim 7 wherein each dosage unit contains 15 to 30 mg of trans-4[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol hydrochloride and 250 to 500 mg of ampicillin.
11. Compositions as claimed in claim 7 wherein each dosage unit contains 15 to 30 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol hydrochloride and 500 to 750 mg of amoxicillin.
12. Compositions as claimed in claim 7 wherein each dosage unit contains 15 to 30 mg of trans-4-[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol hydrochloride and 500 to 750 mg of amoxicillin.
13. Compositions as claimed in claim 6 wherein each dosage unit contains from 1/4 to 1/2 the amount of trans-4-[(2-amino-3,5-dibromo-benzyl)-aminojcyclohexanol hydrochloride and of antibiotic specified in claim 8.
14. Pharmaceutical compositions as claimed in claim 1 substantially as herein described.
15. Pharmaceutical compositions substantially as herein described in any one of Examples 1 to 12.
16. A synergistic combination of an antibiotic or a physiologically acceptable salt thereof and trans-4[(2-amino-3,5-dibromo-benzyl)-amino]cyclohexanol or a physiologically acceptable acid addition salt thereof for use in the treatment of infections of the respiratory tract.
17. A method of treating a patient suffering from or susceptible to an infection of the respiratory tract which comprises administering to the said patient substantially simultaneously an effective amount of an antibiotic or a physiologically acceptable salt thereof and trans-4-[(2-amino-3,5-dibromo-benzyl)amino]cyclohexanol or a physiologically acceptable acid addition salt thereof.
18. Each and every novel method, process, composition and product herein disclosed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3034975A DE3034975C2 (en) | 1980-09-17 | 1980-09-17 | Drug combination used to treat infectious respiratory diseases |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2083749A true GB2083749A (en) | 1982-03-31 |
GB2083749B GB2083749B (en) | 1984-05-23 |
Family
ID=6112126
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8127983A Expired GB2083749B (en) | 1980-09-17 | 1981-09-16 | Drug combination comprising ambroxol and an antibiotic for the treatment of infectious diseases of the respiratory tract |
Country Status (8)
Country | Link |
---|---|
CH (1) | CH648209A5 (en) |
DE (1) | DE3034975C2 (en) |
FR (1) | FR2493145A1 (en) |
GB (1) | GB2083749B (en) |
HK (1) | HK20785A (en) |
IE (1) | IE51517B1 (en) |
SG (1) | SG785G (en) |
ZA (1) | ZA816417B (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2516795A1 (en) * | 1981-11-20 | 1983-05-27 | Teijin Ltd | MEDICAMENT FOR THE TREATMENT OF RESPIRATORY DISEASES COMPRISING A MEDICAMENT AGAINST RESPIRATORY DISEASES AND A HYDROXYCYCLOHEXYLAMINE OR ONE OF ITS SALTS |
WO1996025155A1 (en) * | 1995-02-15 | 1996-08-22 | Bioscreen Pty. Limited | Diagnosis of and compositions and methods for the treatment of disease |
CN1323662C (en) * | 2004-06-18 | 2007-07-04 | 江苏恒瑞医药股份有限公司 | Pharmaceutical composition containing ambroxol and erdosteine or acetylcysteine and application thereof |
CN100434078C (en) * | 2005-05-16 | 2008-11-19 | 天津药物研究院 | Ambroxol hydrochloride compound slow-release tablet and its preparing method |
US20100330176A1 (en) * | 2002-02-27 | 2010-12-30 | Boehringer Ingelheim Pharma Gmbh And Co. Kg | Ambroxol for the treatment of painful conditions in the mouth and pharyngeal cavity |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19933148A1 (en) | 1999-07-20 | 2001-01-25 | Boehringer Ingelheim Int | Lozenge containing ambroxol |
RU2749902C2 (en) * | 2018-10-31 | 2021-06-18 | Общество С Ограниченной Ответственностью "Валента-Интеллект" | Pharmaceutical composition for treatment of infectious and inflammatory diseases |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795585A (en) * | 1972-02-17 | 1973-08-16 | Thomae Gmbh Dr K | NEW PULMONARY MEDICINE |
-
1980
- 1980-09-17 DE DE3034975A patent/DE3034975C2/en not_active Expired
-
1981
- 1981-09-15 CH CH5962/81A patent/CH648209A5/en not_active IP Right Cessation
- 1981-09-16 GB GB8127983A patent/GB2083749B/en not_active Expired
- 1981-09-16 ZA ZA816417A patent/ZA816417B/en unknown
- 1981-09-16 IE IE2147/81A patent/IE51517B1/en not_active IP Right Cessation
- 1981-09-17 FR FR8117603A patent/FR2493145A1/en active Granted
-
1985
- 1985-01-04 SG SG7/85A patent/SG785G/en unknown
- 1985-03-21 HK HK207/85A patent/HK20785A/en not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2516795A1 (en) * | 1981-11-20 | 1983-05-27 | Teijin Ltd | MEDICAMENT FOR THE TREATMENT OF RESPIRATORY DISEASES COMPRISING A MEDICAMENT AGAINST RESPIRATORY DISEASES AND A HYDROXYCYCLOHEXYLAMINE OR ONE OF ITS SALTS |
WO1996025155A1 (en) * | 1995-02-15 | 1996-08-22 | Bioscreen Pty. Limited | Diagnosis of and compositions and methods for the treatment of disease |
US20100330176A1 (en) * | 2002-02-27 | 2010-12-30 | Boehringer Ingelheim Pharma Gmbh And Co. Kg | Ambroxol for the treatment of painful conditions in the mouth and pharyngeal cavity |
CN1323662C (en) * | 2004-06-18 | 2007-07-04 | 江苏恒瑞医药股份有限公司 | Pharmaceutical composition containing ambroxol and erdosteine or acetylcysteine and application thereof |
CN100434078C (en) * | 2005-05-16 | 2008-11-19 | 天津药物研究院 | Ambroxol hydrochloride compound slow-release tablet and its preparing method |
Also Published As
Publication number | Publication date |
---|---|
DE3034975C2 (en) | 1986-11-27 |
IE812147L (en) | 1982-03-17 |
CH648209A5 (en) | 1985-03-15 |
FR2493145A1 (en) | 1982-05-07 |
IE51517B1 (en) | 1987-01-07 |
DE3034975A1 (en) | 1982-04-29 |
ZA816417B (en) | 1983-05-25 |
FR2493145B1 (en) | 1984-12-21 |
SG785G (en) | 1985-06-14 |
HK20785A (en) | 1985-03-29 |
GB2083749B (en) | 1984-05-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PE20 | Patent expired after termination of 20 years |
Effective date: 20010915 |