CA2459493A1 - New pharmaceutical compositions for inhalation - Google Patents

New pharmaceutical compositions for inhalation Download PDF

Info

Publication number
CA2459493A1
CA2459493A1 CA002459493A CA2459493A CA2459493A1 CA 2459493 A1 CA2459493 A1 CA 2459493A1 CA 002459493 A CA002459493 A CA 002459493A CA 2459493 A CA2459493 A CA 2459493A CA 2459493 A1 CA2459493 A1 CA 2459493A1
Authority
CA
Canada
Prior art keywords
acid
hydroxy
phenylbutoxy
benzenedimethanol
hexyl
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.)
Granted
Application number
CA002459493A
Other languages
French (fr)
Other versions
CA2459493C (en
Inventor
Guenter Linz
Rainer Soyka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Individual
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.)
Filing date
Publication date
Priority claimed from DE2001145438 external-priority patent/DE10145438A1/en
Priority claimed from DE2002109243 external-priority patent/DE10209243A1/en
Application filed by Individual filed Critical Individual
Publication of CA2459493A1 publication Critical patent/CA2459493A1/en
Application granted granted Critical
Publication of CA2459493C publication Critical patent/CA2459493C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Otolaryngology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to novel medicament compositions based on tiotropium salts and poorly soluble salmeterol salts. The invention also relates to a method for the production of said compositions and to the use thereof for treating diseases of the respiratory tract.

Claims (15)

1) Pharmaceutical composition, characterised in that it contains one or more tiotropium salts (1) combined with one or more salmeterol salts (2) of limited solubility, the salmeterol salts 2 having a solubility in water of 0.1 mg/ml or less.
2) Pharmaceutical composition according to claim 1, characterised in that the active substances 1 and 2 are present either together in a single preparation or in two separate preparations.
3) Pharmaceutical composition according to one of claims 1 or 2, characterised in that 1 is present in the form of the chloride, bromide, iodide, methanesulphonate, para-toluenesulphonate or methylsulphate, preferably in the form of the bromide.
4) Pharmaceutical composition according to one of claims 1 to 3, characterised in that 2 is selected from the acid addition salts of salmeterol 2' with one of the following acids: 2-hydroxy-1-naphthoic acid, 3,5-dichlorosalicylic acid, furan-carboxylic acid, 2,5-dihydroxy-terephthalic acid, cinnamic acid, triphenylacetic acid, 4-phenylcinnamic acid, biphenyl-2-carboxylic acid, 4-trifluoromethylcinnamic acid, 9-fluorenylideneacetic acid, 3-(2-naphthyl)acrylic acid, 3-(1-naphthyl)acrylic acid, 1-naphthoic acid, 2,6-dichlorobenzoic acid, 3,4-dichlorobenzoic acid, 3,5-dichlorobenzoic acid, 4-bromobenzoic acid, 4-trifluoromethylbenzoic acid, 4-isopropylbenzoic acid, 4-tert.-butylbenzoic acid, 3-(3-indolyl)acrylic acid, 2,4-dichlorocinnamic acid, 2,6-dichlorocinnamic acid, 2,5-dimethoxy-cinnamic acid, 2-trifluoromethylcinnamic acid, 3-trifluoromethylcinnamic acid, 3-chlorocinnamic acid, 3,4-dichlorocinnamic acid, 4-bromocinnamic acid, 4-chlorocinnamic acid, 4-methoxycinnamic acid, 4-fluorocinnamic acid, 4-isopropylcinnamic acid, 4-tert.-butylcinnamic acid, 2,6-difluorocinnamic acid, 2,4-difluorocinnamic acid, 3,4-difluorocinnamic acid, 2,4,5-trifluorocinnamic acid, 3,4,5-trifluorocinnamic acid, 3-methoxysalicylic acid, 4-methoxysalicylic acid, 5-methoxysalicylic acid, 4-methylsalicylic acid,
5-aminosalicylic acid, 3-chlorosalicylic acid, 5-sulphosalicylic acid, 5-acetylsalicylic acid, 3,5-diiodosalicylic acid, isoquinoline-1-carboxylic acid, 9-fluorenecarboxylic acid, 9-fluorenone-1-carboxylic acid, 3,5-diisopropyl-salicylic acid or diflunisal.

5) Pharmaceutical composition according to one of claims 1 to 3, characterised in that 2 is selected from among the following salts:

4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-phenylcinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-trifluoromethyl-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,4-dichloro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,4-dichloro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-(2-naphthyl)acrylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-(1-naphthyl)acrylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,6-dichloro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,5-dimethoxy-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2-trifluoromethyl-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-trifluoromethyl-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-chloro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-bromo-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-chloro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-methoxy-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-fluoro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-isopropyl-cinnamate salt;

4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-tert-butyl-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,4-difluoro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,4-difluoro-cinnamate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,4,5-trifluoro-cinnamate salt;
and 4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,4,5-trifluoro-cinnamate salt.
6) Pharmaceutical composition according to one of claims 1 to 3, characterised in that 2 is selected from among the following salts:
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-5-(2,4-difluorophenyl)salicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,5-diisopropyl-salicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-chloro-salicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,5-dichloro-salicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-2,5-dihydroxyterephthalate salt (base : acid = 1:2);
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-methoxysalicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-methoxysalicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-5-methoxysalicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-4-methylsalicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-5-aminosalicylate salt;
4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3-chlorosalicylate salt;

4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-5-sulpho-salicylate salt;
4-Hydroxy-.alpha.1-[([6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-5-acetylsalicylate salt;
and 4-Hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)-hexyl]-amino]-methyl]-1,3-benzenedimethanol-3,5-diiodosalicylate salt.
7) Pharmaceutical composition according to one of claims 1 to 6, characterised in that the weight ratios of tiotropium 1' to salmeterol 2' are in the range from 1:300 to 30:1, preferably from 1:230 to 20:1.
8) Pharmaceutical composition according to one of claims 1 to 7, characterised in that a single application corresponds to a dosage of the combination of active substances 1' and 2' of 0.01 to 1000 µg, preferably 0.1 to 200 µg.
9) Pharmaceutical composition according to one of claims 1 to 8, characterised in that it is in the form of a powder suitable for inhalation.
10) Pharmaceutical composition according to claim 9, characterised in that it is an inhalable powder which contains 1 and 2 in admixture with suitable physiologically acceptable excipients selected from among the monosaccharides, disaccharides, oligo- and polysaccharides, polyalcohols, salts, or mixtures of these excipients with one another.
11) Inhalable powder according to claim 10, characterised in that the excipient has a maximum mean particle size of up to 250 µm, preferably between 10 and 150 µm.
12) Capsules, characterised in that they contain an inhalable powder according to claim 10 or 11.
13) Pharmaceutical composition according to claim 9, characterised in that it is an inhalable powder which contains only the active substances 1 and 2 as its sole ingredients.
14) Use of a composition according to one of claims 1 to 13 for preparing a medicament for the treatment of respiratory complaints.
15) Use according to claim 14 for preparing a medicament for the treatment of asthma or COPD.
CA2459493A 2001-09-14 2002-09-06 New pharmaceutical compositions for inhalation Expired - Fee Related CA2459493C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE2001145438 DE10145438A1 (en) 2001-09-14 2001-09-14 New salts of salmeterol with substituted salicylic acid, useful as well tolerated beta-mimetic agents for treating asthma or chronic obstructive pulmonary disease
DE10145438.4 2001-09-14
DE2002109243 DE10209243A1 (en) 2002-03-04 2002-03-04 Synergistic, well tolerated medicament combination of tiotropium salt and sparingly water-soluble salmeterol salt, useful for treating asthma or chronic obstructive pulmonary disease
DE10209243.5 2002-03-04
PCT/EP2002/009974 WO2003024452A1 (en) 2001-09-14 2002-09-06 Novel medicaments for inhalation

Publications (2)

Publication Number Publication Date
CA2459493A1 true CA2459493A1 (en) 2003-03-27
CA2459493C CA2459493C (en) 2011-08-02

Family

ID=26010149

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2459493A Expired - Fee Related CA2459493C (en) 2001-09-14 2002-09-06 New pharmaceutical compositions for inhalation

Country Status (8)

Country Link
EP (1) EP1429768B1 (en)
JP (1) JP2005504076A (en)
AR (1) AR036518A1 (en)
CA (1) CA2459493C (en)
MX (1) MXPA04002401A (en)
PE (1) PE20030646A1 (en)
UY (1) UY27445A1 (en)
WO (1) WO2003024452A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9687478B2 (en) 1999-07-14 2017-06-27 Almirall, S.A. Quinuclidine derivatives and medicinal compositions containing the same
US9737520B2 (en) 2011-04-15 2017-08-22 Almirall, S.A. Aclidinium for use in improving the quality of sleep in respiratory patients
US10085974B2 (en) 2008-03-13 2018-10-02 Almirall, S.A. Dosage and formulation

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10351663A1 (en) * 2002-12-20 2004-07-01 Boehringer Ingelheim Pharma Gmbh & Co. Kg Stable, accurately dosable inhalable powder medicament for treating asthma or chronic obstructive pulmonary disease, containing tiotropium, specific form of salmeterol xinafoate and auxiliary
EP1803469A3 (en) * 2003-07-29 2011-10-26 Boehringer Ingelheim Pharma GmbH & Co. KG Medicaments for inhalation comprising betamimetics and an anticholinergic
CA2617897A1 (en) * 2005-08-06 2007-02-15 Boehringer Ingelheim International Gmbh Method for the treatment of dyspnea comprising combined administration of tiotropium salts and salts of salmeterol
US20080114063A1 (en) * 2006-08-16 2008-05-15 Action Medicines Use of 2,5-Dihydroxybenzene Derivatives for the Treatment of Tissue Reactive Diseases
EP2100598A1 (en) 2008-03-13 2009-09-16 Laboratorios Almirall, S.A. Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1172663B (en) * 1961-04-28 1964-06-25 Maggioni & C Spa Process for the production of bismuth tri- (p-phenylcinnamate)
GB8310477D0 (en) * 1983-04-18 1983-05-25 Glaxo Group Ltd Chemical compounds
DE19726871C1 (en) * 1997-06-24 1999-03-04 Werner Kreutz Synergistic compositions for the selective control of tumor tissue
DE19921693A1 (en) * 1999-05-12 2000-11-16 Boehringer Ingelheim Pharma Pharmaceutical composition for treating respiratory disorders, e.g. asthma, comprises combination of anticholinergic and beta-mimetic agents having synergistic bronchospasmolytic activity and reduced side-effects
ATE233084T1 (en) * 1999-04-14 2003-03-15 Glaxo Group Ltd PHARMACEUTICAL AEROSOL FORMULATION
DE10056104A1 (en) * 2000-11-13 2002-05-23 Boehringer Ingelheim Pharma Drug compositions useful for treatment of respiratory diseases, especially asthma and chronic obstructive pulmonary disease comprises tiotropium salts and salmeterol salts

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9687478B2 (en) 1999-07-14 2017-06-27 Almirall, S.A. Quinuclidine derivatives and medicinal compositions containing the same
US10034867B2 (en) 1999-07-14 2018-07-31 Almirall, S.A. Quinuclidine derivatives and medicinal compositions containing the same
US10588895B2 (en) 1999-07-14 2020-03-17 Almirall, S.A. Quinuclidine derivatives and medicinal compositions containing the same
US10085974B2 (en) 2008-03-13 2018-10-02 Almirall, S.A. Dosage and formulation
US11000517B2 (en) 2008-03-13 2021-05-11 Almirall, S.A. Dosage and formulation
US9737520B2 (en) 2011-04-15 2017-08-22 Almirall, S.A. Aclidinium for use in improving the quality of sleep in respiratory patients

Also Published As

Publication number Publication date
MXPA04002401A (en) 2004-05-31
CA2459493C (en) 2011-08-02
PE20030646A1 (en) 2003-07-23
EP1429768A1 (en) 2004-06-23
EP1429768B1 (en) 2016-11-16
WO2003024452A1 (en) 2003-03-27
JP2005504076A (en) 2005-02-10
UY27445A1 (en) 2003-04-30
AR036518A1 (en) 2004-09-15

Similar Documents

Publication Publication Date Title
US7368104B2 (en) Treatment of respiratory diseases
US6835389B1 (en) Powder Composition for nasal administration
TWI282286B (en) Pharmaceutical composition a bilayer tablet having an immediate release phase of paracetamol and a sustained release phase of paracetamol
KR20120112644A (en) Loxoprofen-containing pharmaceutical composition
KR20090023650A (en) Compositions of glycopyrronium salt for inhalation
KR20150108816A (en) Ultra low density pulmonary powders
JP2019019132A (en) Stable pharmaceutical composition
JP2016106153A (en) Loxoprofen-containing pharmaceutical preparation
JP2014514271A5 (en)
CA2459493A1 (en) New pharmaceutical compositions for inhalation
JP6607508B2 (en) Orally disintegrating solid pharmaceutical dosage unit containing parturition control substances
JP5624367B2 (en) Loxoprofen-containing pharmaceutical preparation
KR101697773B1 (en) Modified release composition comprising doxofylline
JP6073231B2 (en) Stable pharmaceutical composition
JP2016169235A (en) Loxoprofen-containing pharmaceutical composition
JP2014159377A (en) Sublimation inhibition method for sublimable medicine
WO2013018766A1 (en) Stable pharmaceutical composition
JPH06227995A (en) Stabilized solid preparation
JP2021520397A (en) Pharmaceutical dry powder composition for inhalation containing thyroid hormone
JP2023018887A (en) Escitalopram oxalate-containing tablet
JP2021176903A (en) Inhaled preparation of isoglycyrrhizic acid or salt thereof, and applications thereof in preparing drugs for treating respiratory diseases
JP2024050466A (en) Solid Composition
JPH1017473A (en) Antitussive agent for cold
JP2005232128A (en) Pharmaceutical composition for rhinitis
WO2012115946A1 (en) Treating human male copd patients with oral bedoradrine

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20180906