DE2207460C2 - Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen Lungenveränderungen - Google Patents
Verwendung von Hydroxycylohexylaminderivaten bei der Behandlung von ödematös atelektatischen LungenveränderungenInfo
- Publication number
- DE2207460C2 DE2207460C2 DE2207460A DE2207460A DE2207460C2 DE 2207460 C2 DE2207460 C2 DE 2207460C2 DE 2207460 A DE2207460 A DE 2207460A DE 2207460 A DE2207460 A DE 2207460A DE 2207460 C2 DE2207460 C2 DE 2207460C2
- Authority
- DE
- Germany
- Prior art keywords
- treatment
- edematous
- hydroxycylohexylamine
- derivatives
- alveoli
- 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.)
- Expired
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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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 |
| AU52272/73A AU475165B2 (en) | 1972-02-17 | 1973-02-16 | Treatment of respiration conditions using hydroxycyclohexylamino compounds |
| FR7305578A FR2181742B1 (enrdf_load_stackoverflow) | 1972-02-17 | 1973-02-16 | |
| IL41564A IL41564A (en) | 1972-02-17 | 1973-02-16 | Pharmaceutical compositions containing n-cyclohexylbenzylamine derivatives |
| 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 |
| 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 |
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 (enrdf_load_stackoverflow) |
| BE (1) | BE795585A (enrdf_load_stackoverflow) |
| DE (1) | DE2207460C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2181742B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1420976A (enrdf_load_stackoverflow) |
| IE (1) | IE37288B1 (enrdf_load_stackoverflow) |
| IL (1) | IL41564A (enrdf_load_stackoverflow) |
| ZA (1) | ZA731068B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| 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)
| 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/xx 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 IL IL41564A patent/IL41564A/en unknown
- 1973-02-16 IE IE245/73A patent/IE37288B1/xx unknown
- 1973-02-16 GB GB779573A patent/GB1420976A/en not_active Expired
- 1973-02-16 AU AU52272/73A patent/AU475165B2/en not_active Expired
- 1973-02-16 FR FR7305578A patent/FR2181742B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL41564A0 (en) | 1973-04-30 |
| BE795585A (fr) | 1973-08-16 |
| IE37288B1 (en) | 1977-06-22 |
| FR2181742B1 (enrdf_load_stackoverflow) | 1976-10-22 |
| AU475165B2 (en) | 1976-08-12 |
| ZA731068B (en) | 1974-11-27 |
| GB1420976A (en) | 1976-01-14 |
| IL41564A (en) | 1976-02-29 |
| AU5227273A (en) | 1974-08-22 |
| FR2181742A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| IE37288L (en) | 1973-08-17 |
| DE2207460A1 (de) | 1973-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |