DE2207460C2 - Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen - Google Patents

Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen

Info

Publication number: DE2207460C2
Authority: DE; Germany
Prior art keywords: treatment; edematous; hydroxycylohexylamine; derivatives; alveoli
Prior art date: 1972-02-17
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.): Expired

Application number

DE2207460A

Other languages

German (de)

English (en)

Other versions

DE2207460A1 (de

Inventor

Johannes Dipl.-Chem. Dr. 7950 Biberach Keck

Sigfrid Dr. Püschmann

Hans-Dietrich Dr. Renovanz

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

Dr Karl Thomae 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.)

1972-02-17

Filing date

1972-02-17

Publication date

1985-06-20

Priority to BE795585D priority Critical patent/BE795585A/fr

1972-02-17 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1972-02-17 Priority to DE2207460A priority patent/DE2207460C2/de

1973-02-15 Priority to ZA731068A priority patent/ZA731068B/xx

1973-02-16 Priority to IL41564A priority patent/IL41564A/en

1973-02-16 Priority to IE245/73A priority patent/IE37288B1/xx

1973-02-16 Priority to FR7305578A priority patent/FR2181742B1/fr

1973-02-16 Priority to AU52272/73A priority patent/AU475165B2/en

1973-02-16 Priority to GB779573A priority patent/GB1420976A/en

1973-08-23 Publication of DE2207460A1 publication Critical patent/DE2207460A1/de

1985-06-20 Application granted granted Critical

1985-06-20 Publication of DE2207460C2 publication Critical patent/DE2207460C2/de

Status Expired legal-status Critical Current

Links

210000004072 lung Anatomy 0.000 title claims description 8
230000002497 edematous effect Effects 0.000 title 1
238000004519 manufacturing process Methods 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
241001465754 Metazoa Species 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002775 capsule Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
239000004480 active ingredient Substances 0.000 description 4
-1 ampoules Substances 0.000 description 4
235000002906 tartaric acid Nutrition 0.000 description 4
239000011975 tartaric acid Substances 0.000 description 4
JBDGDEWWOUBZPM-UHFFFAOYSA-N 4-[(2-amino-3,5-dibromophenyl)methylamino]-1-cyclohexanol Chemical compound NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1 JBDGDEWWOUBZPM-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000008298 dragée Substances 0.000 description 3
235000003642 hunger Nutrition 0.000 description 3
230000000241 respiratory effect Effects 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
239000001828 Gelatine Substances 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 2
239000003708 ampul Substances 0.000 description 2
229940124584 antitussives Drugs 0.000 description 2
QNVKOSLOVOTXKF-PFWPSKEQSA-N chembl1514634 Chemical compound Cl.NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 QNVKOSLOVOTXKF-PFWPSKEQSA-N 0.000 description 2
230000002950 deficient Effects 0.000 description 2
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
230000037351 starvation Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 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
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
UERRZQCPQRIPHN-HAQNSBGRSA-N NC1=C(CN[C@@H]2CC[C@H](CC2)O)C=CC=C1 Chemical compound NC1=C(CN[C@@H]2CC[C@H](CC2)O)C=CC=C1 UERRZQCPQRIPHN-HAQNSBGRSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
241000219289 Silene Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000003419 expectorant effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000001744 histochemical effect Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000001965 increasing effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229940116108 lactase Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical compound ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 description 1
201000002652 newborn respiratory distress syndrome Diseases 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
238000012859 sterile filling Methods 0.000 description 1
238000011146 sterile filtration Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000012360 testing method Methods 0.000 description 1

Classifications

- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
- 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

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)

DE2207460A 1972-02-17 1972-02-17 Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen Expired DE2207460C2 (de)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
BE795585D BE795585A (fr)	1972-02-17		Nouveau medicament pulmonaire
DE2207460A DE2207460C2 (de)	1972-02-17	1972-02-17	Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen
ZA731068A ZA731068B (en)	1972-02-17	1973-02-15	Novel pulmonary remedy
IE245/73A IE37288B1 (en)	1972-02-17	1973-02-16	Pharmaceutical compositions for use in the treatment of certain respiratory diseases or conditions in prematurely born children
IL41564A IL41564A (en)	1972-02-17	1973-02-16	Pharmaceutical compositions containing n-cyclohexylbenzylamine derivatives
FR7305578A FR2181742B1 (fr)	1972-02-17	1973-02-16
AU52272/73A AU475165B2 (en)	1972-02-17	1973-02-16	Treatment of respiration conditions using hydroxycyclohexylamino compounds
GB779573A GB1420976A (en)	1972-02-17	1973-02-16	Pharmaceutical compositions for use in the treatment of certain respiratory diseases or conditions in prematurely born children

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2207460A DE2207460C2 (de)	1972-02-17	1972-02-17	Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen

Publications (2)

Publication Number	Publication Date
DE2207460A1 DE2207460A1 (de)	1973-08-23
DE2207460C2 true DE2207460C2 (de)	1985-06-20

Family

ID=5836238

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2207460A Expired DE2207460C2 (de)	1972-02-17	1972-02-17	Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen

Country Status (8)

Country	Link
AU (1)	AU475165B2 (fr)
BE (1)	BE795585A (fr)
DE (1)	DE2207460C2 (fr)
FR (1)	FR2181742B1 (fr)
GB (1)	GB1420976A (fr)
IE (1)	IE37288B1 (fr)
IL (1)	IL41564A (fr)
ZA (1)	ZA731068B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3034975C2 (de) *	1980-09-17	1986-11-27	Dr. Karl Thomae Gmbh, 7950 Biberach	Arzneimittelkombination zur Behandlung infektiöser Atemwegerkrankungen
JPS5888311A (ja) *	1981-11-20	1983-05-26	Teijin Ltd	呼吸器疾患治療剤
CN102516096B (zh) *	2011-11-28	2013-09-25	海南灵康制药有限公司	一种盐酸氨溴索化合物的精制法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1593579B1 (de) *	1966-05-10	1972-02-03	Thomae Gmbh Dr K	Hydroxy-cyclohexylamine,deren physiologisch vertraeglichen Saeureadditionssalze und Verfahren zu ihrer Herstellung

0
- BE BE795585D patent/BE795585A/fr not_active IP Right Cessation
1972
- 1972-02-17 DE DE2207460A patent/DE2207460C2/de not_active Expired
1973
- 1973-02-15 ZA ZA731068A patent/ZA731068B/xx unknown
- 1973-02-16 IE IE245/73A patent/IE37288B1/xx unknown
- 1973-02-16 FR FR7305578A patent/FR2181742B1/fr not_active Expired
- 1973-02-16 AU AU52272/73A patent/AU475165B2/en not_active Expired
- 1973-02-16 IL IL41564A patent/IL41564A/en unknown
- 1973-02-16 GB GB779573A patent/GB1420976A/en not_active Expired

Also Published As

Publication number	Publication date
IE37288L (en)	1973-08-17
FR2181742A1 (fr)	1973-12-07
IL41564A0 (en)	1973-04-30
AU475165B2 (en)	1976-08-12
ZA731068B (en)	1974-11-27
AU5227273A (en)	1974-08-22
IE37288B1 (en)	1977-06-22
DE2207460A1 (de)	1973-08-23
GB1420976A (en)	1976-01-14
BE795585A (fr)	1973-08-16
FR2181742B1 (fr)	1976-10-22
IL41564A (en)	1976-02-29

Legal Events

Date	Code	Title
1978-11-16	OD	Request for examination
1985-06-20	D2	Grant after examination
1985-12-19	8364	No opposition during term of opposition

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