JPS5835194B2 - 1,3- Benzoxole - Google Patents
1,3- BenzoxoleInfo
- Publication number
- JPS5835194B2 JPS5835194B2 JP10076273A JP10076273A JPS5835194B2 JP S5835194 B2 JPS5835194 B2 JP S5835194B2 JP 10076273 A JP10076273 A JP 10076273A JP 10076273 A JP10076273 A JP 10076273A JP S5835194 B2 JPS5835194 B2 JP S5835194B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methyl
- benzodioxole
- acid
- lower alkyl
- 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
- -1 benzhydryl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 150000005529 1,3-benzodioxoles Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000739 antihistaminic agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 4
- 230000001387 anti-histamine Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000003405 ileum Anatomy 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical group NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】 本発明は次の一般式（Ｉ） 〔式中Ｒ１及びＲ２は低級アルキル基を表わす。[Detailed description of the invention] The present invention relates to the following general formula (I) [In the formula, R1 and R2 represent a lower alkyl group.
またＲｏ とＲ２とが結合して環構造を形成する場合
も含む。It also includes a case where Ro and R2 combine to form a ring structure.
Ｒ３は低級アルキル基またはベンツヒドリル基を、ｎは
２または３の数字を表わす。R3 represents a lower alkyl group or a benzhydryl group, and n represents a number of 2 or 3.
〕で示される新規化合物１・３−ベンゾジオキソール誘
導体；２・２−ジ低級アルキル置換−５−（Ｎｌ （
Ｎ４−置換−１・４−ジアゾシクロアルキル）〕−〕メ
チルー１３−ベンゾジオキソールの合成方法に関するも
のである。] New compound 1,3-benzodioxole derivative; 2,2-di-lower alkyl substituted-5-(Nl (
The present invention relates to a method for synthesizing N4-substituted-1,4-diazocycloalkyl)]-]methyl-13-benzodioxole.
本発明により得られる化合物（Ｉ）は持続性のある抗ヒ
スタミン作用を有する。Compound (I) obtained according to the present invention has a long-lasting antihistamine effect.
本発明の方法は次の反応式に従って行なわれる。The method of the present invention is carried out according to the following reaction formula.
〔式中Ｒ□、Ｒ２、Ｒ３及びｎは前述の意味を有する。[In the formula, R□, R2, R3 and n have the above-mentioned meanings.
〕即ち一般式（ｎ）で示されるアミド体；２・２−ジ低
級アルキル置換−５−（Ｎ１＝（Ｎ’−置換−１・４−
ジアゾシクロアルキル）〕−〕カルボニルー１３−ベン
ゾジオキソールを還元して目的とする化合物（Ｉ）を得
る。] That is, an amide compound represented by the general formula (n); 2,2-di-lower alkyl-substituted-5-(N1=(N'-substituted-1,4-
Diazocycloalkyl)]-]carbonyl-13-benzodioxole is reduced to obtain the desired compound (I).
還元方法としては例えばリチウムアルミニラムノ・イド
ライド、ソジウムジハイドロビス（２−メトキシエトキ
シ）アルミネート等の金属錯化合物を使用する方法や、
銅・ニッケル触媒存在下の高温高圧水素添加による還元
法などを適用する事が可能である。Reduction methods include, for example, methods using metal complex compounds such as lithium aluminum rhamno-hydride and sodium dihydrobis(2-methoxyethoxy) aluminate;
It is possible to apply reduction methods such as high temperature and high pressure hydrogenation in the presence of copper and nickel catalysts.
目的物精製の為の再結晶溶媒としてはメタノール、エタ
ノール、プロパツール等の低級アルコールまたはこれら
低級アルコールをエチルエーテルの混合溶媒の使用が好
結果を与えた。The use of lower alcohols such as methanol, ethanol, propatool, or a mixed solvent of these lower alcohols and ethyl ether as a recrystallization solvent for purification of the target product gave good results.
化合物（Ｉ）は所望ならば通常の造塩方法によって薬・
理学に許容され得る酸の添加塩に変換する事が可能であ
る。Compound (I) can be prepared as a drug by a conventional salt-forming method if desired.
It is possible to convert it into a scientifically acceptable addition salt of the acid.
薬理学的に許容され得る酸としては無機酸としては例え
ば塩酸、硫酸、燐酸、硝酸等が、有機酸としては例えば
醋酸、クエン酸、酒石酸、蓚酸、ファール酸、マレイン
酸、メタンスルホン酸等が挙げられる。Examples of pharmacologically acceptable acids include inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, and nitric acid, and examples of organic acids such as acetic acid, citric acid, tartaric acid, oxalic acid, phallic acid, maleic acid, and methanesulfonic acid. Can be mentioned.
本発明の出発原料である化合物は新規化合物であるが、
例えば次の反応式に従って合成する事が可能である。Although the compound that is the starting material of the present invention is a new compound,
For example, it can be synthesized according to the following reaction formula.
〔式中Ｒ１、Ｒ２、Ｒ３及びｎは前述の意味を有する。[In the formula, R1, R2, R3 and n have the above-mentioned meanings.
〕即ち２・２−ジ低級アルキル置換−１・３−ベンゾジ
オキソール−５−カルボン酸（Ｉ［Ｉ）またはその反応
性誘導体と１−置換−１・４−ジアゾシクロアルカン（
ＩＶ）とを反応させてアミド体（ＩＩ）を得る。] That is, 2,2-dilower alkyl-substituted-1,3-benzodioxole-5-carboxylic acid (I[I) or its reactive derivative and 1-substituted-1,4-diazocycloalkane (
IV) to obtain amide compound (II).
化合物（ＩＩ［）の反応性誘導体としては、例えば酸無
水物、混合酸無水物、ハライド、活性エステル等があげ
られる。Examples of reactive derivatives of compound (II[) include acid anhydrides, mixed acid anhydrides, halides, and active esters.
反応に際しては反応系に関与しない溶媒例エバベンゼン
、トルエン、キシレン、アセトン、ピリジン等を適宜に
用いる事が可能であ※る。During the reaction, solvents that do not participate in the reaction system, such as evabenzene, toluene, xylene, acetone, and pyridine, can be used as appropriate.
化合物（ＩＩＩ）の反応性誘導体としてクロライド等の
ハライドを用いた場合には反応系にピリジン、トリエチ
ルアミン、炭酸アルカリ、苛性アルカリ等の脱酸剤を添
加する事により反応を円滑に行なう事ができる。When a halide such as chloride is used as the reactive derivative of compound (III), the reaction can be carried out smoothly by adding a deoxidizing agent such as pyridine, triethylamine, alkali carbonate, or caustic alkali to the reaction system.
この場合ピリジンは脱酸剤と溶媒をかねる。In this case, pyridine serves as both a deoxidizing agent and a solvent.
化合物（ｎ）は塩酸塩に変換して確認を行なった。Compound (n) was converted into a hydrochloride and confirmed.
次に本発明において原料として使用される化合物（ｎ）
を表記するが本発明はこれに限定されるものではない。Next, the compound (n) used as a raw material in the present invention
However, the present invention is not limited thereto.
本発明の化合物の抗ヒスタミン作用は摘出モルモット回
腸を用いたマグナス装置により測定した。The antihistamine action of the compounds of the present invention was measured using a Magnus apparatus using isolated guinea pig ileum.
本発明による化合物としては、２−メチル−２−エチル
−５−（Ｎ４−ベンツヒドリル）−ピペラジノメチル−
１・３−ベンゾジオキソール（以下化合物Ａと称する）
を選定した。Compounds according to the invention include 2-methyl-2-ethyl-5-(N4-benzhydryl)-piperazinomethyl-
1,3-benzodioxole (hereinafter referred to as compound A)
was selected.
その結果ヒスタミン１０−７？／ＴＬｌで生じる摘出モ
ルモット回腸片の収縮（約１♂の張力）は化合物Ａｌ０
−’？／ｒｕｌの前処置により１／４に抑制される事が
判明した。The result is histamine 10-7? The contraction of the isolated guinea pig ileum piece (tension of about 1 ♂) occurring at /TLl is caused by the compound Al0
-'? It was found that pretreatment with /rul suppressed the effect to 1/4.
またこの作用は回腸片をタイロード氏液で洗滌しても消
失しなかった。Moreover, this effect did not disappear even when the ileum pieces were washed with Tyrode's solution.
この事は化合物Ａの抗ヒスタミン作用が持続性である事
を裏付けるものである。This confirms that the antihistamine action of Compound A is long-lasting.
従って化合物Ａによって代表される本発明の化合物は持
続性の抗ヒスタミン作用を有し抗ヒスタミン剤としての
使用が有望視される。Therefore, the compound of the present invention represented by Compound A has a long-lasting antihistamine effect and is expected to be used as an antihistamine agent.
次に実施例により本発明を説明する。Next, the present invention will be explained with reference to examples.
実施例 １
２−メチル−２−エチル−５−（Ｎ’−ベンツヒドリル
−ピペラジノ）−メチル−１・３−ベンゾジオキソール
の合成
２−メチル−２−エチル−５−（Ｎ’−ベンツヒドリル
−ピペラジノ）−カルボニルート３ベンゾジオキソール
（表１−屑１）４．Ｏｆをソジウムジハイドロビス（２
−メトキシエトキシ）アルミネー）３′ｆＩのベンゼン
溶液に加え、８０℃で２時間加熱攪拌する。Example 1 Synthesis of 2-methyl-2-ethyl-5-(N'-benzhydryl-piperazino)-methyl-1,3-benzodioxole 2-methyl-2-ethyl-5-(N'-benzhydryl- Piperazino)-Carbonyroute 3 Benzodioxole (Table 1 - Scrap 1) 4. Of is sodium dihydrobis (2
-Methoxyethoxy)aluminae) 3'fI in benzene solution, and stirred under heating at 80°C for 2 hours.
反応液は水冷下に水を加え、エーテル抽出する。Water was added to the reaction solution under water cooling, and the mixture was extracted with ether.
エーテル抽出外を水洗し硫酸マグネシウムで乾燥した後
、減圧留去する。The residue from the ether extraction was washed with water, dried over magnesium sulfate, and then evaporated under reduced pressure.
残渣に１０％エタノール性塩酸を加え減圧下に濃縮乾固
する。Add 10% ethanolic hydrochloric acid to the residue and concentrate to dryness under reduced pressure.
残渣をエタノール・エチルエーテル混合溶媒より再結晶
する。The residue is recrystallized from a mixed solvent of ethanol and ethyl ether.
目的物を塩酸塩として得る。The desired product is obtained as a hydrochloride.
収量４．１１ 融点２１９〜２２ＦＣ
元素分析値 Ｃ２８Ｈ３’Ｎ２Ｏ２・２ ＨＣ１・１／
３Ｈ２０として
ＣＨＮ
理論値（％） ６７．０５ ６．８３ ５．５９実測
値（％） ６７．０２ ６．８８ ５．５７実施例
２
２・２−メチル、エチル−５−（Ｎ’−メチル−ホモピ
ペラジノ）−メチル−１・３−ベンゾジオキソールの合
成
２−メチル−２−エチル−５−（Ｎ’−メチルホモピペ
ラジノ）−カルボニルート３−ベンゾジオキソール（表
１４２）を実施例１に従って反応処理する。Yield 4.11 Melting point 219-22FC Elemental analysis C28H3'N2O2・2 HC1・1/
CHN as 3H20 Theoretical value (%) 67.05 6.83 5.59 Actual value (%) 67.02 6.88 5.57 Example
2 Synthesis of 2,2-methyl, ethyl-5-(N'-methyl-homopiperazino)-methyl-1,3-benzodioxole 2-methyl-2-ethyl-5-(N'-methylhomopiperazino) )-Carbonyl-3-benzodioxole (Table 142) is reacted according to Example 1.
目的物を塩酸塩として得る。融点１９８’Ｃ
元素分析値 Ｃｌ７Ｈ２６Ｎ２０２・２ＨＣ１・２／３
Ｈ２０として
ＣＨＮ
理論値（％） ５４．４０ ７．９０ ７．４６実測
値（％） ５４．３２ ８．０５ ７．３２実施例
３
２−シクロヘキシルスピロ−５−（Ｎ’ −メチル−ピ
ペラジノ）−メチル−１・３−ベンゾジオキソールの合
成
２−シクロヘキシルスピロ−５−（Ｎ’ −メチル−ピ
ペラジノ）−カルボニルート３−ベンゾジオキソール（
表１ ４３）を実施例１に従って反応処理する。The desired product is obtained as a hydrochloride. Melting point 198'C Elemental analysis value Cl7H26N202・2HC1・2/3
CHN as H20 Theoretical value (%) 54.40 7.90 7.46 Actual value (%) 54.32 8.05 7.32 Example
3 Synthesis of 2-cyclohexylspiro-5-(N'-methyl-piperazino)-methyl-1,3-benzodioxole 2-cyclohexylspiro-5-(N'-methyl-piperazino)-carbonyroot 3-benzodioxole Kisor (
Table 1 43) is reacted according to Example 1.
目的物を塩酸塩として得る。融点２４３〜２４９℃
元素分析値 Ｃ１８Ｈ２６Ｎ２ ｏ２・２ ＨＣｌ
としてＣＨＮ
理論値（％） ５７．６０ ７Ｌ５１ ７．４６実測
値（％） ５７．５６ ７．５０ ７．３１実施例
４
２−シクロヘキシルスピロ−５−（Ｎ’ −ベンツヒド
リル−ピペラジノ）−メチル−１・３−ベンゾジオキソ
ールの合成
２−シクロヘキシルスピロ−５−（Ｎ’ −ベンツヒド
リル−ピペラジノ）−カルボニル−１・３−ペンゾジオ
キソール（表１−／Ｉ６４ ）を実施例１に従って反応
処理する。The desired product is obtained as a hydrochloride. Melting point 243-249℃ Elemental analysis value C18H26N2 o2・2 HCl
CHN Theoretical value (%) 57.60 7L51 7.46 Actual value (%) 57.56 7.50 7.31 Example
4 Synthesis of 2-cyclohexylspiro-5-(N'-benzhydryl-piperazino)-methyl-1,3-benzodioxole 2-cyclohexylspiro-5-(N'-benzhydryl-piperazino)-carbonyl-1,3 - Penzodioxole (Table 1-/I64) is reacted according to Example 1.
目的物を塩酸塩として得る。The desired product is obtained as a hydrochloride.
融点２２５〜２２９℃
元素分析値 Ｃ３ｏＨ３４Ｎ２０２・２ＨＣ１・１／２
Ｈ２０として
ＣＨＮMelting point 225-229℃ Elemental analysis value C3oH34N202・2HC1・1/2
CHN as H20
Claims (1)
含む。 Ｒ３は低級アルキル基またはベンツヒドリル基を、ｎは
２または３の数字を表わす。 〕で示されるアミド化合物を還元する事を特徴とする、
次の一般式 〔式中Ｒ１、Ｒ２、Ｒ３及びｎは前述の意味を有する。 〕で示される１・３−ベンゾジオキソール誘導体の合成
方法。[Claims] [In the formula, R1 and R2 represent a lower alkyl group. It also includes cases where R1 and R2 combine to form a ring structure. R3 represents a lower alkyl group or a benzhydryl group, and n represents a number of 2 or 3. ], characterized by reducing the amide compound represented by
The following general formula [wherein R1, R2, R3 and n have the above-mentioned meanings] ] A method for synthesizing a 1,3-benzodioxole derivative.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10076273A JPS5835194B2 (en) | 1973-09-08 | 1973-09-08 | 1,3- Benzoxole |
| US05/503,515 US3981864A (en) | 1973-09-08 | 1974-09-05 | 1,3-Benzodioxol derivatives |
| DE2442750A DE2442750A1 (en) | 1973-09-08 | 1974-09-06 | 1,3-BENZODIOXOLE DERIVATIVES |
| FR7430330A FR2242978B1 (en) | 1973-09-08 | 1974-09-06 | |
| ES429871A ES429871A1 (en) | 1973-09-08 | 1974-09-07 | 1,3-Benzodioxol derivatives |
| GB39323/74A GB1484291A (en) | 1973-09-08 | 1974-09-09 | 1,3-benzo-dioxole derivatives |
| US05/609,145 US4026895A (en) | 1973-09-08 | 1975-08-29 | 1,3-Benzodioxol derivatives |
| US05/684,735 US4051125A (en) | 1973-09-08 | 1976-05-10 | 1,3-Benzodioxol derivatives |
| US05/770,038 US4083853A (en) | 1973-09-08 | 1977-02-18 | 1,3-Benzodioxol derivatives |
| US05/770,039 US4117228A (en) | 1973-09-08 | 1977-02-18 | 1,3-benzodioxol derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10076273A JPS5835194B2 (en) | 1973-09-08 | 1973-09-08 | 1,3- Benzoxole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5050388A JPS5050388A (en) | 1975-05-06 |
| JPS5835194B2 true JPS5835194B2 (en) | 1983-08-01 |
Family
ID=14282508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10076273A Expired JPS5835194B2 (en) | 1973-09-08 | 1973-09-08 | 1,3- Benzoxole |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5835194B2 (en) |
-
1973
- 1973-09-08 JP JP10076273A patent/JPS5835194B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5050388A (en) | 1975-05-06 |
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