in the above reaction scheme , the compounds ( 2 ), ( 3 ), ( 4 ), ( 5 ), ( 6 ) and ( a ) are novel , and among them , the compounds having the pyrazolopyridine skeleton are represented by the general formula as given below : ## str7 ## [ wherein r 1 represents -- oh , -- och 2 ph ( where ph is a phenyl group ), ## str8 ## or -- o -- ch 2 -- ch ( oh )-- ch 2 -- nh -- ch ( ch 3 ) 2 ; and r 2 represents h or -- coor ( where r is a c 1 - c 3 alkyl group )]. in the first place , 3 - hydroxypyridine ( 1 ) is benzylated for the purpose of protecting the hydroxyl group , producing 3 - benzyloxypyridine ( 2 ). this reaction can be carried out , for example , by allowing benzyl chloride to act on the compound ( 1 ) in the presence of a deacidifying agent , such as sodium hydroxide . then , the compound ( 2 ) is reacted with o - mesitylenesulfonylhydroxylamine to give n - amino - 3 - benzyloxypyridinium mesitylenesulfonate ( 3 ). the reaction can be allowed to proceed in such a solvent as methylene chloride , under ice - cooling , if desired . the resulting compound ( 3 ), after action of such a base as anhydrous potassium carbonate , is treated with a lower alkyl ester of propiolic acid , whereupon a cyclization reaction takes place to yield 4 - benzyloxypyrazolo [ 1 , 5 - a ]- pyridine - 3 - carboxylic acid lower alkyl ester ( 4 ). this reaction can be allowed to proceed in such a solvent as dimethylformamide at room temperature . the production of the compound ( 4 ) is generally accompanied by the formation of the 6 - benzyloxy derivative which is the isomer of the compound ( 4 ), and the two compounds each can be separated from the other by suitable means , such as column chromatography . in the next place , the compound ( 4 ) is subjected to removal of its benzyl and alkoxycarbonyl groups to give 4 - hydroxypyrazolo [ 1 , 5 - a ] pyridine ( 5 ). the removal reaction may be conducted in stepwise ; firstly , the alkoxycarbonyl group is hydrolyzed in the presence of an alkali such as alkali hydroxide to convert to the carboxyl group , and then heated in a solvent under the addition of copper chromite ( 2cuocr 2 o 3 ) or reacted with a strong acid such as hydrobromic acid to cause decarboxylation reaction for removing the carboxyl group . subsequently , the benzyl group can be removed , for example , by reacted with boron trifluoride etherate and dimethyl sulfide in a solvent such as methylene chloride . in addition , the compound ( 4 ), after converting its alkoxycarbonyl group to a carboxyl group as described in the above , can also be subjected to simultaneous removal of the carboxyl and benzyl groups by reacting with a strong acid such as hydrobromic acid . by employing hydrobromic acid , the reaction can be finished in a shortened period of time and in increased yields . furthermore , the compound ( 4 ) can also be reacted , for example , with 47 % hydrobromic acid to achieve improved yields by a progress of simultaneous removal of the alkoxycarbonyl and benzyl groups . 4 - hydroxypyrazolo [ 1 , 5 - a ] pyridine ( 5 ) as obtained by the above procedure is reacted , in the form of alkali metal salt , with glycidyl tosylate to give 3 -( pyrazolo [ 1 , 5 - a ] pyrid - 4 - yloxy )- 1 , 2 - epoxypropane ( 6 ). the reaction is preferably carried out in a solvent such as dimethylformamide under an atmosphere of argon gas . then , the compound ( 6 ) is reacted with isopropylamine to produce 1 -( isopropylamino )- 3 -( pyrazolo [ 1 , 5 - a ] pyrid - 4 - yloxy )- 2 - propanol ( a ), with approximately quantitative yields being achieved . in the step of producing the compound ( 6 ) from the compound ( 5 ), optically active compound ( 6 ) can be synthesized by employing glycidyl tosylate obtained by the tosylation of optically active glycidol , and optically active product compound ( a ) can be obtained by reacting the optically active compound ( 6 ) with isopropylamine . the compound ( a ), which exhibits anti - serotonergic activity , can be used as an agent for treating neurosis , such as an antidepressant , antimania agent , etc . and can be administered orally or in a form of subcutaneous or intravenous injection . its daily dose for human adults is 1 to 100 mg , preferably 10 to 20 mg , in the case of oral administration , and 0 . 05 to 20 mg , preferably 0 . 1 to 10 mg , in the case of injection . the compound ( a ), because of the chemical configuration of its basic skeleton , is easily degradable and consequently becomes shorter in half - life period within the body , suggesting that it can alleviate adverse effects caused by accumulation of the drug . in the meantime , in contrast to pindolol , the compound ( a ) did not show the blocking activity of β - adrenoceptor . reverting to the drawings , fig1 and fig2 are bar graphs representing the results of the test on anti - serotonergic activity as conducted in experiment example where a denotes the compound according to this invention , that is 1 -( isopropylamino )- 3 -( pyrazolo [ 1 , 5 - a ]- pyrid - 4 - yloxy )- 2 - propanol . below given are the experiment example and examples to illustrate this invention more particularly . in accordance with the method as described in japanese journal of pharmacology ( japan . j . pharmacol . ), 51 , 421 - 424 ( 1989 ), the compound ( a ) was tested for its anti - serotonergic activity . male dba strain mice ( supplied by japan slc ) weighing 20 to 25 g ( 6 - weeks aged ) were maintained on a 12 hr light - dark cycle from 7 : 00 to 19 : 00 at 24 °± 1 ° c ., while they were allowed free access to food and water . the experiment was performed from 13 : 00 to 17 : 00 . a solution of the compound ( a ) in isotonic saline was administered to the animals intraperitoneally , with isotonic saline in the same volume being administered to the control . 15 minutes after intraperitoneal application , tryptamine was given each animal into the tail vein at a dose of 25 mg / kg . after administration of tryptamine , mice were housed individually in each transparent plastic cage to observe their behavior . among the serotonin syndrome induced after administration of tryptamine , the head weaving and hindlimb abduction which clearly appeared were scored every minutes in accordance with the following criteria of assessment : 1 = behavior sustained for a period of less than 20 sec ( occasional ), 2 = behavior sustained for a period of not less than 20 sec but less than 40 sec ( frequent ), 3 = behavior sustained for not less than 40 sec ( continuous ). observation was effected until behavior disappeared , and the results were expressed as a total score obtained by summing up individual scores recorded every minute . the scores recorded for the head weaving and hindlimb abduction were evaluated by mann - whitney &# 39 ; s u - test . as may be evident from each of the figures , the compound ( a ), when given the animals , clearly suppressed the head weaving and hindlimb abduction in contrast to the control . consequently , it is considered evident that the compound ( a ) exhibits anti - serotonergic activity . to a suspension of 3 - hydroxypyridine ( 24 . 7 g , 260 mmole ) in distilled methylene chloride ( 260 ml ) were added adogen 464 ( 1 . 6 ml ), 40 % naoh ( 130 ml ), benzyl chloride ( 32 ml , 278 mmole ), followed by stirring for 3 days at room temperature . the organic layer was separated from the reaction solution , and the aqueous layer was admixed with water and extracted with methylene chloride . the resulting extract was combined with the methylene chloride layer separated previously , and the combined solution was washed with saturated saline , dried over k 2 co 3 and freed of the solvent by distillation . the residue was purified on a column of silica gel ( 7734 , n - hexane : ethyl acetate = 20 : 1 to 5 : 1 ). a solution of o - mesitylenesulfonylhydroxylamine ( 13 . 7 g , 44 . 6 mmole , purity of 70 %) in methylene chloride ( 150 ml ) was added dropwise to a solution of 3 - benzyloxypyridine ( 8 . 25 g , 44 . 6 mmole ) in methylene chloride ( 150 ml ) under ice - cooling , with stirring . the reaction solution was returned to room temperature , stirred for 1 hours and concentrated to one - quarter of the original volume at 20 ° to 30 ° c ., and ether was added to the concentrate , thereby white crystals were precipitated . this product was used in the next reaction , without being purified . the product was recrystallized from a mixed solution of methanol and ethyl acetate to give white flaky crystals having a melting point of 105 ° to 108 ° c . elemental analysis , for c 21 h 24 o 4 n 2 s : calcd . : c , 62 . 99 ; h , 6 . 04 ; n , 7 . 00 . found : c , 62 . 85 ; h , 6 . 03 ; n , 6 . 71 . anhydrous k 2 co 3 ( 5 . 8 g , 42 . 0 mmole ) was added to a solution of the n - amino salt ( 3 ) ( 14 . 0 g , 35 . 0 mmole ) in dmf ( 350 ml ), and the mixture was stirred at room temperature for 2 to 3 minutes until it turned blue from initial green . then , methyl propiolate ( 4 . 4 ml , 52 . 5 mmole ) was added dropwise to the mixture , followed by stirring for 25 hours . the insoluble matter was filtered off from the reaction mixture , and solvent was removed from the filtrate by distillation . the residue was admixed with methylene chloride , resulting insoluble matter was filtered off , and solvent was removed from the filtrate by distillation . the residue was purified on a column of silica gel ( 9385 , n - hexane : ethyl acetate = 5 : 1 to 2 : 1 ). yield of 4 . 7 g or 47 . 6 %. in this experiment , the 6 - benzyloxy isomer was also produced simultaneously . yield of 2 . 1 g or 21 . 1 %. the compound 4 &# 39 ; was recrystallized from methyl acetate - n - hexane mixed solution to give white crystals with a melting point of 80 . 5 ° to 81 . 5 ° c . elemental analysis , for c 18 h 14 o 3 n 2 : calcd . : c , 68 . 07 ; h , 5 . 00 ; n , 9 . 92 . found : c , 67 . 99 ; h , 4 . 99 ; n , 9 . 81 . a suspension of the methyl ester derivative ( 4 &# 39 ;) ( 113 mg , 0 . 40 mmole ) in 47 % hbr ( 2 ml ) was refluxed for 10 minutes . the reaction mixture was freed of the solvent by distillation as far as possible , and the residue was made alkaline ( ph 8 ) with nahco 3 . the resulting slurry was admixed with ethanol , insoluble matter was filtered off therefrom , and the filtrate was freed of the solvent by distillation . the same procedure was repeated once again , ether was added to the resulting residue , insoluble matter was filtered off therefrom , and the filtrate was freed of the solvent by distillation . the residue was purified on a column of silica gel ( 7734 , chloroform ). elemental analysis , for c 7 h 8 on 2 : calcd . : c , 62 . 68 ; h , 4 . 51 ; n , 20 . 89 . found : c , 62 . 35 ; h , 4 . 63 ; n , 21 . 06 . nah ( containing 60 % of oil , 270 mg , 4 . 5 mmole ) was washed with anhydrous petroleum ether , and was admixed , under atmosphere of argon gas , with distilled dmf ( 15 ml ) and 4 - hydroxypyrazolo [ 1 , 5 - a ] pyridine ( 5 ) ( 402 mg , 3 . 0 mmole ), followed by stirring for 30 min to give a light pink suspension . subsequently , glycidyl tosylate ( 821 mg , 3 . 6 mmole ) was added to the suspension , followed by stirring overnight under atmosphere of argon gas to obtain a red - yellow suspension . the reaction mixture was neutralized by adding about 10 ml of saturated aqueous nh 4 cl , followed by addition of water ( 20 ml ) and extraction with ether . the extract was washed with water , dried and freed of the solvent by distillation , and the residue was purified on a column of silica gel ( 7734 , chloroform ). nmr ( cdcl 3 ) δ : 2 . 80 ( dd , j = 5 . 3 hz , hb ), 2 . 95 ( dd , j = 5 . 4 hz , ha ), 3 . 4 - 3 . 5 ( m , hc ), 4 . 08 ( dd , j = 11 . 6 hz , one of ch 2 ), 4 . 38 ( dd , j = 11 . 3 hz , one of ch 2 ), 6 . 38 ( d , j = 7 hz , h - 5 ), 6 . 64 ( t , j = 7 hz , h - 6 ), 6 . 66 ( dd , j = 2 . 5 , 1 hz , h - 3 ), 7 . 88 ( d , j = 2 . 5 hz , h - 2 ), 8 . 15 ( d , j = 7 hz , h - 7 ). the epoxy derivative ( 6 ) ( 336 mg , 1 . 77 mmole ) was refluxed in isopropylamine - water ( 10 : 1 ) mixed solution for 45 minutes . the reaction solution was freed of the solvent by distillation , and the residue was admixed with chloroform . the mixture was dried , and the solvent was distilled off to give crystals showing one spot on tlc . the product was recrystallized from n - hexane to produce white crystals with a melting point of 65 ° to 67 ° c . elemental analysis , for c 13 h 19 o 2 n 3 : calcd . : c , 62 . 62 ; h , 7 . 68 ; n , 16 . 85 . found : c , 62 . 76 ; h , 7 . 58 ; n , 16 . 73 . nmr ( cdcl 3 ) δ 1 . 11 ( d , j = 6 hz , ch 3 x2 ), 2 . 0 - 2 . 3 ( brs , nh and oh ), 2 . 7 - 3 . 0 ( m , -- ch ( oh ) ch 2 nhch --), 4 . 0 - 4 . 2 ( m , -- och 2 ch ( oh )--), 6 . 39 ( brd , j = 7 hz , h - 5 ), 6 . 62 ( dd , j = 2 . 5 , 1 hz , h - 3 ), 6 . 64 ( t , j = 7 hz , h - 6 ), 7 . 87 ( d , j = 2 . 5 hz , h - 2 ), 8 . 15 ( dt , j = 7 . 1 hz , h - 7 ).