1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(isopropyl)-3-azetidinol and α-naphthol were reacted in the same manner as in Example 6 to form 1-(α-naphthoxy)-3-(iso-propylamino)-2-propanol. Then the propanol was dissolved in anhydrous ether and was converted to a hydrochloride by blowing a hydrochloric acid gas into the resulting solution. As a result 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol hydrochloride melting at 162°-164° C was obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(isopropyl)-3-azetidinol and α-naphthol were reacted in the same manner as in Example 6 to form 1-(α-naphthoxy)-3-(iso-propylamino)-2-propanol. Then the propanol was dissolved in anhydrous ether and was converted to a hydrochloride by blowing a hydrochloric acid gas into the resulting solution. As a result 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol hydrochloride melting at 162°-164° C was obtained.

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 11.5 parts of 1-(iso-propyl)-3-azetidinol and 15.8 parts of α-naphthol 0.2 part of 182°- potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 20 hours. The reaction mixture was cooled and then extracted with ether. The ether extract was washed with 2N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized for cyclohexane or subjected to distillation under reduced pressure. As a result 19.6 parts of 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol having a melting point of 94°-96° C. and a boiling point of 158°-159° C. under 2.5 mm Hg were obtained. The yield was 76%. The residue of infra-red spectrum analysis of the product are as follows: was added The reaction mixture was cooled extracted with ether The ether extract was washed with 2N-NaOH aqueous solution The liquor was dried over anhydrous sodium sulfate the solvent was distilled off The residue was recrystallized for cyclohexane subjected to distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.55 ml of (1-methylethyl)amine (0.0297 mol) are mixed with 1.25 ml of H2O and the mixture is then stirred with 5 g of 1-(1-naphthyloxy)-2,3-epoxypropane (0.0249 mol) and reacted at room temperature for 23 hours. reacted at room temperature for 23 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Rats (Sprague Dawley) weighing 300–400 gms were purchased from Simonsen laboratories. CVT-3619 was dissolved in DMSO and further diluted in saline. CVT-510 was dissolved in saline. Ketamine was purchased from Fort Dodge Animal Health, Xylazine from Bayer and Acepromazine Maleate from Fermenta Animal Health Co. Metoprolol and propranolol were purchased from SIGMA. Esmolol was obtained from a local pharmacy. further diluted in saline CVT-510 was dissolved in saline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Rats (Sprague Dawley) weighing 300–400 gms were purchased from Simonsen laboratories. CVT-3619 was dissolved in DMSO and further diluted in saline. CVT-510 was dissolved in saline. Ketamine was purchased from Fort Dodge Animal Health, Xylazine from Bayer and Acepromazine Maleate from Fermenta Animal Health Co. Metoprolol and propranolol were purchased from SIGMA. Esmolol was obtained from a local pharmacy. further diluted in saline CVT-510 was dissolved in saline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The sensitized guinea pigs are injected i.v. with 1 mg/kg propranolol, 5 mg/kg indomethacin and 2 mg/kg mepyramine given together in a volume of 1 ml/kg. Fifteen minutes later the animals are challenged with nebulized ovalbumin. Test compounds are administered orally 2 hours before challenge with ovalbumin. Suppression of anaphylactic bronchospasm is expressed as a percent inhibition of the peak increase in intratracheal pressure by comparison to a vehicle-treated control group. In this procedure, 3-methyl-1-phenyl-1,8-naphthyridin-2(1H)-one (referred to as Compound A hereinafter) provided a 96% inhibition at a dose of 5 mg/kg p.o. Fifteen minutes increase in intratracheal pressure by comparison to a vehicle-treated control group

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(isopropyl)-3-azetidinol and α-naphthol were reacted in the same manner as in Example 6 to form 1-(α-naphthoxy)-3-(iso-propylamino)-2-propanol. Then the propanol was dissolved in anhydrous ether and was converted to a hydrochloride by blowing a hydrochloric acid gas into the resulting solution. As a result 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol hydrochloride melting at 162°-164° C was obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(isopropyl)-3-azetidinol and α-naphthol were reacted in the same manner as in Example 6 to form 1-(α-naphthoxy)-3-(iso-propylamino)-2-propanol. Then the propanol was dissolved in anhydrous ether and was converted to a hydrochloride by blowing a hydrochloric acid gas into the resulting solution. As a result 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol hydrochloride melting at 162°-164° C was obtained.

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 11.5 parts of 1-(iso-propyl)-3-azetidinol and 15.8 parts of α-naphthol 0.2 part of 182°- potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 20 hours. The reaction mixture was cooled and then extracted with ether. The ether extract was washed with 2N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized for cyclohexane or subjected to distillation under reduced pressure. As a result 19.6 parts of 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol having a melting point of 94°-96° C. and a boiling point of 158°-159° C. under 2.5 mm Hg were obtained. The yield was 76%. The residue of infra-red spectrum analysis of the product are as follows: was added The reaction mixture was cooled extracted with ether The ether extract was washed with 2N-NaOH aqueous solution The liquor was dried over anhydrous sodium sulfate the solvent was distilled off The residue was recrystallized for cyclohexane subjected to distillation under reduced pressure

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 11.5 parts of 1-(iso-propyl)-3-azetidinol and 15.8 parts of α-naphthol 0.2 part of 182°- potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 20 hours. The reaction mixture was cooled and then extracted with ether. The ether extract was washed with 2N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized for cyclohexane or subjected to distillation under reduced pressure. As a result 19.6 parts of 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol having a melting point of 94°-96° C. and a boiling point of 158°-159° C. under 2.5 mm Hg were obtained. The yield was 76%. The residue of infra-red spectrum analysis of the product are as follows: was added The reaction mixture was cooled extracted with ether The ether extract was washed with 2N-NaOH aqueous solution The liquor was dried over anhydrous sodium sulfate the solvent was distilled off The residue was recrystallized for cyclohexane subjected to distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.55 ml of (1-methylethyl)amine (0.0297 mol) are mixed with 1.25 ml of H2O and the mixture is then stirred with 5 g of 1-(1-naphthyloxy)-2,3-epoxypropane (0.0249 mol) and reacted at room temperature for 23 hours. reacted at room temperature for 23 hours