IT9020562A1 - Agente antitussivo e mucoregolatore, sua preparazione e composizioni farmaceutiche - Google Patents
Agente antitussivo e mucoregolatore, sua preparazione e composizioni farmaceuticheInfo
- Publication number
- IT9020562A1 IT9020562A1 IT020562A IT2056290A IT9020562A1 IT 9020562 A1 IT9020562 A1 IT 9020562A1 IT 020562 A IT020562 A IT 020562A IT 2056290 A IT2056290 A IT 2056290A IT 9020562 A1 IT9020562 A1 IT 9020562A1
- Authority
- IT
- Italy
- Prior art keywords
- benzylamine
- hydroxycyclohexyl
- dibromo
- preparation
- pct
- Prior art date
Links
- 229940124584 antitussives Drugs 0.000 title claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000003434 antitussive agent Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 230000000954 anitussive effect Effects 0.000 claims abstract description 4
- 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 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- GRQLANNZNDOPST-UHFFFAOYSA-N 4-[(3,5-dibromophenyl)methylamino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NCC1=CC(Br)=CC(Br)=C1 GRQLANNZNDOPST-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- MEYUFEONQBWJKB-UHFFFAOYSA-N n-[2,4-dibromo-6-[[(4-hydroxycyclohexyl)amino]methyl]phenyl]benzamide Chemical compound C1CC(O)CCC1NCC1=CC(Br)=CC(Br)=C1NC(=O)C1=CC=CC=C1 MEYUFEONQBWJKB-UHFFFAOYSA-N 0.000 claims 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 210000003097 mucus Anatomy 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229960005174 ambroxol Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010044314 Tracheobronchitis Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- -1 ampoules or vials Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- 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
- A61P11/10—Expectorants
-
- 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
- A61P11/14—Antitussive agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Paper (AREA)
Description
Descrizione dell'invenzione industriale avente per titolo: "AGENTE ANTITUSSIVO E MUCOREGOLATORE, SUA PREPARAZIONE E COM-POSIZIONI FARMACEUTICHE"
La presente invenzione ha per oggetto la 2-benzoilammino-3,5-dibrano-N-(4-idrossicicloesil)benzilamina di fannula I
ed i suoi sali oon acidi farmaceuticamente accettabili.
Un sale particolarmente preferito è il cloridrato, usato per le prove farmacologiche e indicato nel seguito per brevità con la sigla YS 912.
La 2-ammino -3,5-dibromo-N-(4-idrossicicloesil)benzilammina è un noto farmaco (denominazione comune inter azionale Ambroxol) da tempo impiegato in terapia umana, il composto oggetto della presente invenzione è il derivato benzoilico dell'Ambroxol e presenta rispetto al composto capostipite migliorate caratteristiche farmacologiche e farmacocinetiche.
Il composto I o un suo sale (ad esempio YS 912), per il previsto inpiego terapeutico cerne agente antitosse e/o mucoregolatore, è opportunamente formulato con tecniche ed eccipienti convenzionali in formulazioni farmaceutiche atte alla somministrazione arale, parenterale o rettale, quelli capsule, compresse, sciroppo, granulare, fiale o flaconcini, supposte. La quantità di principio attivo somministrabile al giorno dipenderà da più fattori (peso, sesso ed età del paziente e gravità della patologia da trattare) ma sarà una linea di massima compresa tra 5 e 100 mg al giorno, in una o più somministrazioni. Le composizioni dell'invenzione seno particolarmente utili nel trattamento di bronchiti, tracheobronchiti, asma, enfisema, sinusiti, otiti, polmoniti di natura sia acuta che cronica.
Il composto I viene preparato per reazione di un derivato attivo dell'acido benzoico (cloruro, anidride mista, imidazolide ecc.) con Ambroxolo in solventi adatti e utilizzando opportune condizioni di reazione.
Occorre infatti considerare che l'acilazione interessa anche il più basico gruppo amminico secondario: il prodotto ivi acilato può tuttavia trasporre al prodotto di formula I per trattamento con HC1 gassoso a caldo. Si preferisce in particolare impiegare il cloruro cene derivato attivato dell'acido benzoico: in tal caso si opera di preferenza in toluene in presenza di piridina.
Il prodotto ottenuto viene quindi trattato con HC1 gassoso a una temperatura conpresa tra 30 e 70°C in un solvente quale etanolo o acetone.
Il seguente Esempio illustra ulteriormente l'invenzione senza per altro limitarla.
ESEMPIO
Ad una soluzione di 3,5—dibromo-N-{4'-cicloesanol)-benzilammina (30 g - 0,079 moli) in Toluolo (150 ml), si aggiunge benzoli cloruro (9,2 cc - 0,079 moli).
Mantenendo la temperatura al di sotto dei 20°C si gocciola Piridina (6,5 oc - 0,079 moli).
Si lascia a temperatura ambiente per 3 ore si lava con 150 ml di acqua. La fase organica, seccata su è evaporata.
Il residuo è cristallizzato da Etanolo.
Si scioglie in Acetone e si aggiunge Acetone gasato con HC1, fino a pH acido.
Si lascia a tenperatura ambiente per 2 ore. Si filtra il solido e si lava con Acetone,
p.f. 278-280°C
Claims (6)
- RIVENDICAZIONI 1. 2-benzoilammino-3,5-dibromo-N- (4-idrossicicloesil)benzilammina di formula Ie suoi sali con acidi farmaceuticamente accettabili.
- 2. Cloridrato di 2-benzoilanmino-3 ,5-dibromo-N-(4-idrossicicloesil) benzilammina.
- 3. Procedimento per la preparazione del composto della rivendicazione 1, caratterizzato dal fatto che si fa reagire un derivato attivo dell'acido benzoico con 3,5-dibromo -N-(4-idrossicicloesil)benzilammina .
- 4. Procedimento secondo la rivendicazione 3, in cui il derivato attivo è il cloruro acido.
- 5. Procedimento secondo la rivendicazione 4 o 5, in cui il prodotto di acilazione è trattato a caldo con HC1 gassoso.
- 6. Composizioni farmaceutiche ad attività antitussiva e mucoregolatrice contenente come principio attivo il composto della rivendicazione 1 o 2.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02056290A IT1248702B (it) | 1990-06-06 | 1990-06-06 | Agente antitussivo e mucoregolatore,sua preparazione e composizioni farmaceutiche |
| DE69104723T DE69104723T2 (de) | 1990-06-06 | 1991-06-03 | Hustenstillendes und schleimregulierendes mittel, verfahren zu seiner herstellung und dieses enthaltende pharmazeutische zusammensetzungen. |
| PCT/EP1991/001023 WO1991018865A1 (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
| AT91911446T ATE113029T1 (de) | 1990-06-06 | 1991-06-03 | Hustenstillendes und schleimregulierendes mittel, verfahren zu seiner herstellung und dieses enthaltende pharmazeutische zusammensetzungen. |
| US07/952,838 US5352703A (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
| EP91911446A EP0532644B1 (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
| CA002083597A CA2083597A1 (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
| ES91911446T ES2061252T3 (es) | 1990-06-06 | 1991-06-03 | Agente antitusivo y regulador de la mucosa, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| JP91510028A JPH05506450A (ja) | 1990-06-06 | 1991-06-03 | 鎮咳および粘液正常化活性を有する物質、その製造方法およびこれを含有する薬剤組成物 |
| AU79564/91A AU644452B2 (en) | 1990-06-06 | 1991-06-03 | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02056290A IT1248702B (it) | 1990-06-06 | 1990-06-06 | Agente antitussivo e mucoregolatore,sua preparazione e composizioni farmaceutiche |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IT9020562A0 IT9020562A0 (it) | 1990-06-06 |
| IT9020562A1 true IT9020562A1 (it) | 1991-12-06 |
| IT1248702B IT1248702B (it) | 1995-01-26 |
Family
ID=11168835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT02056290A IT1248702B (it) | 1990-06-06 | 1990-06-06 | Agente antitussivo e mucoregolatore,sua preparazione e composizioni farmaceutiche |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5352703A (it) |
| EP (1) | EP0532644B1 (it) |
| JP (1) | JPH05506450A (it) |
| AT (1) | ATE113029T1 (it) |
| CA (1) | CA2083597A1 (it) |
| DE (1) | DE69104723T2 (it) |
| ES (1) | ES2061252T3 (it) |
| IT (1) | IT1248702B (it) |
| WO (1) | WO1991018865A1 (it) |
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|---|---|---|---|---|
| US20030166732A1 (en) * | 2002-02-27 | 2003-09-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ambroxol for the treatment of painful conditions in the mouth and pharyngeal cavity |
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| US9765020B2 (en) | 2012-05-23 | 2017-09-19 | Cellix Bio Private Limited | Dichlorophenyl-imino compounds and compositions, and methods for the treatment of mucositis |
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| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432904A (en) * | 1973-08-24 | 1976-04-22 | Uriach & Cia Sa J | N-2-n-cyclohexyl-n-methylaminomethyl-4,6-dibromo-phenyl-benzamides methods for their preparation and compositions containing them |
| FR2399276A1 (fr) * | 1977-08-03 | 1979-03-02 | Rhone Poulenc Ind | Procede de fabrication de billes d'alumine |
| CA1117546A (en) * | 1978-03-02 | 1982-02-02 | John D. Spivack | Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions |
| IT1094864B (it) * | 1978-05-29 | 1985-08-10 | Tosi Franco Ist | Derivati della bromexina e procedimento per la loro preparazione |
| DK110582A (da) * | 1981-03-19 | 1982-09-20 | Hokuriku Pharmaceutical | 2-benzoylamino-substituerede benzylaminderivater samt fremgangsmaade til fremstilling af samme |
| IT1213132B (it) * | 1984-02-02 | 1989-12-14 | Yason Srl | Agente antibroncopneumopatico. |
-
1990
- 1990-06-06 IT IT02056290A patent/IT1248702B/it active IP Right Grant
-
1991
- 1991-06-03 WO PCT/EP1991/001023 patent/WO1991018865A1/en not_active Application Discontinuation
- 1991-06-03 ES ES91911446T patent/ES2061252T3/es not_active Expired - Lifetime
- 1991-06-03 JP JP91510028A patent/JPH05506450A/ja active Pending
- 1991-06-03 EP EP91911446A patent/EP0532644B1/en not_active Revoked
- 1991-06-03 AT AT91911446T patent/ATE113029T1/de not_active IP Right Cessation
- 1991-06-03 DE DE69104723T patent/DE69104723T2/de not_active Revoked
- 1991-06-03 US US07/952,838 patent/US5352703A/en not_active Expired - Fee Related
- 1991-06-03 CA CA002083597A patent/CA2083597A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IT1248702B (it) | 1995-01-26 |
| EP0532644B1 (en) | 1994-10-19 |
| JPH05506450A (ja) | 1993-09-22 |
| DE69104723D1 (de) | 1994-11-24 |
| WO1991018865A1 (en) | 1991-12-12 |
| ES2061252T3 (es) | 1994-12-01 |
| ATE113029T1 (de) | 1994-11-15 |
| DE69104723T2 (de) | 1995-02-23 |
| US5352703A (en) | 1994-10-04 |
| EP0532644A1 (en) | 1993-03-24 |
| CA2083597A1 (en) | 1991-12-07 |
| IT9020562A0 (it) | 1990-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 0001 | Granted | ||
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19960627 |