JPH0137391B2 - - Google Patents
Info
- Publication number
- JPH0137391B2 JPH0137391B2 JP60254326A JP25432685A JPH0137391B2 JP H0137391 B2 JPH0137391 B2 JP H0137391B2 JP 60254326 A JP60254326 A JP 60254326A JP 25432685 A JP25432685 A JP 25432685A JP H0137391 B2 JPH0137391 B2 JP H0137391B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxybenzenesulfonamide
- methanol
- formula
- aminopropyl
- solvent
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 17
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 10
- IORITYIZDHJCGT-SSDOTTSWSA-N 5-[(2r)-2-aminopropyl]-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(C[C@@H](C)N)C=C1S(N)(=O)=O IORITYIZDHJCGT-SSDOTTSWSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical class O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical class NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KEFIGZIQAGNFAX-UHFFFAOYSA-N 1-(2,2-diethoxyethoxy)-2-ethoxybenzene Chemical compound CCOC(OCC)COC1=CC=CC=C1OCC KEFIGZIQAGNFAX-UHFFFAOYSA-N 0.000 description 2
- MKQNYQGIPARLKO-UHFFFAOYSA-N 2-methoxybenzenesulfonamide Chemical compound COC1=CC=CC=C1S(N)(=O)=O MKQNYQGIPARLKO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- NEGYEDYHPHMHGK-UHFFFAOYSA-N para-methoxyamphetamine Chemical compound COC1=CC=C(CC(C)N)C=C1 NEGYEDYHPHMHGK-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 description 1
- KYRRNJIOCLALJQ-UHFFFAOYSA-N 5-(2-aminopropyl)-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(CC(C)N)C=C1S(N)(=O)=O KYRRNJIOCLALJQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YGLMBIHCBHUNBV-UHFFFAOYSA-N n-[1-(4-methoxyphenyl)propan-2-yl]acetamide Chemical compound COC1=CC=C(CC(C)NC(C)=O)C=C1 YGLMBIHCBHUNBV-UHFFFAOYSA-N 0.000 description 1
- LFLZOWIFJOBEPN-UHFFFAOYSA-N nitrate, nitrate Chemical compound O[N+]([O-])=O.O[N+]([O-])=O LFLZOWIFJOBEPN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、医薬特に交感神経α受容体遮断作用
を有する薬剤として有用な置換フエネチルアミン
誘導体（）の新規製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel method for producing substituted phenethylamine derivatives () useful as medicines, particularly drugs having sympathetic alpha receptor blocking action.
（式中、R1は低級アルコキシ基を、R2は低級
アルキル基を、R3は低級アルコキシ基を意味す
る。以下同じ。）
（従来の技術）
この化合物（）は、従来特開昭54−73751号
および特開昭56−110665号公報等に記載された方
法により、ハロヒドリン(イ)またはエポキシド(ロ)と
置換フエノキシエチルアミン(ハ)とからフエニルエ
タノールアミン(ニ)をつくり、これをハロゲン化し
てハライド(ホ)としたのち、還元することにより製
造されていた。 (In the formula, R 1 means a lower alkoxy group, R 2 means a lower alkyl group, and R 3 means a lower alkoxy group. The same applies hereinafter.) (Prior art) This compound () was previously disclosed in JP-A No. 54 Phenylethanolamine (2) is prepared from halohydrin (1) or epoxide (2) and substituted phenoxyethylamine (3) by the method described in JP-A-73751 and JP-A-56-110665, It was produced by halogenating this to form a halide (e) and then reducing it.
（式中、Ｘはハロゲン原子を意味し、また、
R1，R2およびR3は前記の意味を示す。）
（発明の解決手段）
本発明の製造法は、式
で示されるフエネチルアミン誘導体（）と式
で示される置換フエノキシアセトアルデヒド
（）とを反応させ、ついで反応生成物を還元す
ることよりなる頭記置換フエネチルアミン誘導体
（）またはその塩の製造法である。 (In the formula, X means a halogen atom, and
R 1 , R 2 and R 3 have the above meanings. ) (Solution Means of the Invention) The manufacturing method of the present invention is based on the formula The phenethylamine derivative () and formula shown by This is a method for producing the above substituted phenethylamine derivative () or a salt thereof, which comprises reacting the substituted phenoxyacetaldehyde () shown above and then reducing the reaction product.
ここに、R1またはR3の意味する低級アルコキ
シ基とは、メトキシ基、エトキシ基、プロポキシ
基、ブトキシ基等が、また、R2の低級アルキル
基とは、メチル基、エチル基、プロピル基、イソ
プロピル基、ブチル基、ｔ−ブチル基、ペンチル
基等が挙げられる。また、化合物（）の塩とし
ては塩酸塩、硝酸塩、硝酸塩等があげられる。 Here, the lower alkoxy group meant by R 1 or R 3 includes methoxy group, ethoxy group, propoxy group, butoxy group, etc., and the lower alkyl group meant by R 2 includes methyl group, ethyl group, propyl group, etc. , isopropyl group, butyl group, t-butyl group, pentyl group, etc. Further, examples of the salt of the compound () include hydrochloride, nitrate, nitrate, and the like.
本製造法を実施するには先ずフエネチルアミン
誘導体（）と反応対応量の置換フエノキシアセ
トアルデヒド（）とを適当な溶媒中で反応さ
せ、ついで反応生成物を還元する。 To carry out this production method, first, the phenethylamine derivative () is reacted with a corresponding amount of substituted phenoxyacetaldehyde () in a suitable solvent, and then the reaction product is reduced.
フエネチルアミン誘導体（）とアルデヒド
（）との反応は、反応成分を溶解しうる不活性
な溶媒（たとえばメタノール、エーテル、ベンゼ
ン等）の中で、室温乃至加温して行なう。反応は
１時間程度で完結する。反応生成物は、反応液の
まま、あるいは一旦単離したのち、還元する。な
お、この反応ではアルデヒド（）の代りに、反
応するアセタール体を使用することができる。こ
の場合アセタール体は反応に先立つて塩酸等の強
酸を用いて加水分解したのち、反応に供される。 The reaction between the phenethylamine derivative () and the aldehyde () is carried out at room temperature or at elevated temperature in an inert solvent (eg, methanol, ether, benzene, etc.) that can dissolve the reaction components. The reaction is completed in about 1 hour. The reaction product is reduced as a reaction solution or after being isolated once. In this reaction, a reacting acetal can be used instead of the aldehyde (). In this case, the acetal is hydrolyzed using a strong acid such as hydrochloric acid prior to the reaction, and then subjected to the reaction.
還元は、酸化白金、パラジウム炭素、ラネーニ
ツケル等を触媒とする接触環元、水素化ホウ素ナ
トリウム、水素化ホウ素リチウム、水素化アルミ
ニウムリチウムなどの金属水素化物による還元が
採用できる。 For the reduction, reduction using a catalytic ring element such as platinum oxide, palladium on carbon, or Raney nickel, or a metal hydride such as sodium borohydride, lithium borohydride, or lithium aluminum hydride can be employed.
（発明の効果）
本発明の製造法は、従来の方法に比べて反応工
程が短縮されており、処理操作が簡素であるか
ら、工業的実施に適している。(Effects of the Invention) The production method of the present invention has shorter reaction steps and simpler processing operations than conventional methods, and is therefore suitable for industrial implementation.
また、本発明の製造法は、反応の過程でラセミ
化をともなうことがないから、原料化合物として
フエネチルアミン誘導体（）の光学活性体を使
用するときは、対応する光学活性を保持した目的
化合物を得ることができる。 Furthermore, since the production method of the present invention does not involve racemization during the reaction process, when an optically active form of phenethylamine derivative () is used as a raw material compound, a target compound that retains the corresponding optical activity can be obtained. be able to.
（実施例）
つぎに実施例により本発明の製造法をさらに説
明する。なお、本製造法で使用する原料化合物の
置換フエノキシアセトアルデヒド（）またはそ
のアセタールは新規化合物である。その製造法を
参考例１で示す。また、光学活性なフエネチルア
ミン誘導体（）の製造法を参考例２および３で
示す。(Example) Next, the manufacturing method of the present invention will be further explained with reference to Examples. Note that the substituted phenoxyacetaldehyde () or its acetal used as a raw material compound in this production method is a new compound. The manufacturing method is shown in Reference Example 1. Further, reference examples 2 and 3 show a method for producing an optically active phenethylamine derivative ().
参考例 １
水素化ナトリウム（油中60％、4.6ｇ）を乾燥
ジメチルホルムアミド（100ml）中で撹拌し、ｏ
−エトキシフエノール（13.8ｇ）をゆつくり加え
る。混合物を60℃で１時間加熱撹拌し、ついで氷
冷下でブロムアセトアルデヒド ジエチル アセ
タール（19.7ｇ）を１時間かけて滴下した。反応
混合物を室温で１夜撹拌し、60℃で２時間加熱撹
拌した後、氷水（500ml）に注いだ。酢酸エチル
で抽出し、抽出液を水洗して無水硫酸ナトリウム
で乾燥した後、溶媒を留去して油状残渣を得た。
残渣をシリカゲルカラムクロマト（溶出液：ベン
ゼン）に対し、２−（ｏ−エトキシフエノキシ）
アセトアルデヒド ジエチル アセタールを油状
物（12ｇ，47％）として得た。1H−NMR
（CDCl3）δ：1.24（6H，ｔ，Ｊ＝７Hz，−CH2 CH
３×２），1.42（3H，ｔ，Ｊ＝７Hz，−CH2 CH 3），
3.4〜3.9（4H，ｍ，−ＯCH 2CH3×２），3.9〜4.2
（4H，ｍ，−ＯCH 2CH3，−ＯCH 2CH＜），4.86
（1H，ｔ，Ｊ＝５Hz，−OCH2 CH＜），6.88（4H，
ｓ、芳香環）、沸点113−116℃／0.5mmHg
参考例２ （Ｒ（−）体の製造例）
ａ Ｒ（−）−２−（ｐ−メトキシフエニル）−１−
メチルエチルアミン［〔α〕23 D−30.1゜（ｃ＝1.2、
メタノール）、1.5ｇ］をピリジン（６ml）に溶
解し、無水酢酸（３ml）を加えて室温で１時間
放置したのち、溶媒を留去する。残渣を酢酸エ
チルで抽出し、抽出液を水洗して無水硫酸ナト
リウムで乾燥する。溶媒を留去した後、粗結晶
をｎ−ヘキサン−ベンゼンから再結晶してＲ
（＋）−Ｎ−アセチル−２−（ｐ−メトキシフエ
ニル）−１−メチルエチルアミンを1.8ｇを得
た。Reference Example 1 Sodium hydride (60% in oil, 4.6 g) was stirred in dry dimethylformamide (100 ml) and o
- Slowly add ethoxyphenol (13.8g). The mixture was heated and stirred at 60° C. for 1 hour, and then bromoacetaldehyde diethyl acetal (19.7 g) was added dropwise over 1 hour under ice cooling. The reaction mixture was stirred at room temperature overnight, heated and stirred at 60°C for 2 hours, and then poured into ice water (500ml). After extraction with ethyl acetate, the extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain an oily residue.
The residue was purified by silica gel column chromatography (eluent: benzene) using 2-(o-ethoxyphenoxy).
Acetaldehyde diethyl acetal was obtained as an oil (12 g, 47%). 1H -NMR
(CDCl 3 ) δ: 1.24 (6H, t, J=7Hz, −CH 2 CH
3 × 2), 1.42 (3H, t, J=7Hz, -CH 2 CH 3 ),
3.4-3.9 (4H, m, -O CH 2 CH 3 ×2), 3.9-4.2
(4H, m, -O CH 2 CH 3 , -O CH 2 CH<), 4.86
(1H, t, J = 5Hz, -OCH 2 CH <), 6.88 (4H,
s, aromatic ring), boiling point 113-116℃/0.5mmHg Reference Example 2 (Production example of R(-) form) a R(-)-2-(p-methoxyphenyl)-1-
Methylethylamine [[α] 23 D −30.1° (c=1.2,
methanol), 1.5 g] was dissolved in pyridine (6 ml), acetic anhydride (3 ml) was added, and the mixture was allowed to stand at room temperature for 1 hour, and then the solvent was distilled off. The residue is extracted with ethyl acetate, and the extract is washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent, the crude crystals were recrystallized from n-hexane-benzene to give R
1.8 g of (+)-N-acetyl-2-(p-methoxyphenyl)-1-methylethylamine was obtained.
(i) 融点 92〜93℃
(ii) 元素分析値（C12H17NO2として）
Ｃ Ｈ Ｎ
計算値(%) 69.54 8.27 6.76
実測値(%) 69.41 8.19 6.66
(iii) 比旋光度 〔α〕24 D14.8゜（ｃ＝1.09、メタ
ノ
ール）
ｂ クロルスルホン酸（60ｇ）を−10℃に冷却
し、Ｒ（＋）−Ｎ−アセチル−２−（ｐ−メトキ
シフエニル）−１−メチルエチルアミン（６ｇ）
を加える。０〜５℃で１時間撹拌した後、反応
液を氷水（600ｇ）に注加し、析出した油状物
を酢酸エチルで抽出し、抽出液を飽和炭酸水素
ナトリウム水溶液で洗い、無水硫酸ナトリウム
で乾燥する。溶媒を留去した後、残渣は精製す
ることなく、テトラヒドロフラン120mlに溶解
し、５〜10℃で濃アンモニア水（180ml）を滴
下して室温で１時間撹拌する。析出した結晶を
取し、水洗後メタノールから再結晶してＲ
（＋）−５−［２−（アセチルアミノ）プロピル］
−２−メトキシベンゼンスルホンアミドを６ｇ
得た。 (i) Melting point 92-93℃ (ii) Elemental analysis value (as C 12 H 17 NO 2 ) C H N Calculated value (%) 69.54 8.27 6.76 Actual value (%) 69.41 8.19 6.66 (iii) Specific optical rotation [α ] 24 D 14.8゜ (c = 1.09, methanol) b Chlorsulfonic acid (60 g) was cooled to -10°C, and R(+)-N-acetyl-2-(p-methoxyphenyl)-1-methylethylamine was prepared. (6g)
Add. After stirring at 0 to 5°C for 1 hour, the reaction solution was poured into ice water (600 g), the precipitated oil was extracted with ethyl acetate, the extract was washed with saturated aqueous sodium bicarbonate solution, and dried over anhydrous sodium sulfate. do. After distilling off the solvent, the residue is dissolved in 120 ml of tetrahydrofuran without purification, and concentrated aqueous ammonia (180 ml) is added dropwise at 5 to 10°C, followed by stirring at room temperature for 1 hour. The precipitated crystals were collected, washed with water, and then recrystallized from methanol to obtain R.
(+)-5-[2-(acetylamino)propyl]
-6g of 2-methoxybenzenesulfonamide
Obtained.
(i) 融点 197〜198℃
(ii) 元素分析値（C12H18N2O4Sとして）
Ｃ Ｈ Ｎ
計算値(%) 50.34 6.34 9.78
実測値(%) 50.28 6.41 9.69
(iii) 比旋光度 〔α〕24 D14.7゜（ｃ＝1.0、メタ
ノ
ール）
ｃ Ｒ（＋）−５［２−（アセチルアミノ）プロピ
ル］−２−メトキシベンゼンスルホンアミド
（５ｇ）を５％塩酸（125ml）に溶解し、16時間
加熱還流する。溶媒を留去した後、粗結晶をイ
ソプロピルアルコールから再結晶してＲ（−）−
５−（２−アミノプロピル）−２−メトキシベン
ゼンスルホンアミド塩酸塩4.5ｇを得た。 (i) Melting point 197-198℃ (ii) Elemental analysis value (as C 12 H 18 N 2 O 4 S) C H N Calculated value (%) 50.34 6.34 9.78 Actual value (%) 50.28 6.41 9.69 (iii) Specific rotation Degree [α] 24 D 14.7° (c = 1.0, methanol) c Dissolve R(+)-5[2-(acetylamino)propyl]-2-methoxybenzenesulfonamide (5 g) in 5% hydrochloric acid (125 ml) and heat under reflux for 16 hours. After distilling off the solvent, the crude crystals were recrystallized from isopropyl alcohol to give R(-)-
4.5 g of 5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride was obtained.
(i) 融点 273〜277℃（分解）
(ii) 元素分析値 （C10H17ClN2O3Sとして）
Ｃ Ｈ Ｎ
計算値(%) 42.78 6.10 9.98
実測値(%) 42.68 6.00 9.93
(iii) 比旋光度〔α〕24 D−6.3゜（ｃ＝1.03、メタ
ノ
ール）
参考例３ （Ｓ（＋）体の製造例）
ａ 参考例2a）の製造法において、Ｒ（−）−２
−（ｐ−メトキシフエニル）−１−メチルエチル
アミンの代りに、Ｓ（＋）−２−（ｐ−メトキシ
フエニル）−１−メチルエチルアミンを使用し、
Ｓ（−）−Ｎ−アセチル−２−（ｐ−メトキシフ
エニル）−１−メチルエチルアミンを得た。 (i) Melting point 273-277℃ (decomposition) (ii) Elemental analysis value (as C 10 H 17 ClN 2 O 3 S) C H N Calculated value (%) 42.78 6.10 9.98 Actual value (%) 42.68 6.00 9.93 (iii ) Specific rotation [α] 24 D −6.3° (c=1.03, methanol) Reference example 3 (Production example of S(+) form) a In the production method of Reference example 2a), R(−)−2
-(p-methoxyphenyl)-1-methylethylamine is replaced by S(+)-2-(p-methoxyphenyl)-1-methylethylamine,
S(-)-N-acetyl-2-(p-methoxyphenyl)-1-methylethylamine was obtained.
(i) 融点 94〜96℃（ｎ−ヘキサン−ベンゼン
より再結晶）
(ii) 元素分析値（C12H17NO2として）
Ｃ Ｈ Ｎ
計算値(%) 69.54 8.27 6.76
実測値(%) 69.47 8.31 6.64
(iii) 比旋光度 〔α〕24 D−15.3゜（ｃ＝1.25、メ
タ
ノール）
ｂ 参考例2bの製造法において、Ｒ（＋）−Ｎ−
アセチル−２−（ｐ−メトキシフエニル）−１−
メチルエチルアミンの代りにＳ（−）−Ｎ−アセ
チル−２−（ｐ−メトキシフエニル）−１−メチ
ルエチルアミンを使用し、Ｓ（−）−５−［２−
（アセチルアミノ）プロピル］−２−メトキシベ
ンゼンスルホンアミドを得た。 (i) Melting point 94-96℃ (recrystallized from n-hexane-benzene) (ii) Elemental analysis value (as C 12 H 17 NO 2 ) C H N Calculated value (%) 69.54 8.27 6.76 Actual value (%) 69.47 8.31 6.64 (iii) Specific optical rotation [α] 24 D −15.3° (c=1.25, methanol) b In the production method of Reference Example 2b, R(+)−N−
Acetyl-2-(p-methoxyphenyl)-1-
Using S(-)-N-acetyl-2-(p-methoxyphenyl)-1-methylethylamine instead of methylethylamine, S(-)-5-[2-
(Acetylamino)propyl]-2-methoxybenzenesulfonamide was obtained.
(i) 融点 196〜198℃（メタノールより再結
晶）
(ii) 元素分析値（C12H18N2O4Sとして）
Ｃ Ｈ Ｎ
計算値(%) 50.34 6.34 9.78
実測値(%) 50.31 6.24 9.73
(iii) 比旋光度 〔α〕24 D−14.2゜（ｃ＝1.01、メ
タ
ノール）
ｃ 参考例2c）の製造法において、Ｒ（＋）−５−
［２−（アセチルアミノ）プロピル］−２−メト
キシベンゼンスルホンアミドの代りに、Ｓ（−）
−５−［２−（アセチルアミノ）プロピル］−２
−メトキシベンゼンスルホンアミドを使用しＳ
（＋）−５−（２−アミノプロピル）−２−メトキ
シベンゼンスルホンアミド塩酸塩を得た。 (i) Melting point 196-198℃ (recrystallized from methanol) (ii) Elemental analysis value (as C 12 H 18 N 2 O 4 S) C H N Calculated value (%) 50.34 6.34 9.78 Actual value (%) 50.31 6.24 9.73 (iii) Specific optical rotation [α] 24 D −14.2° (c = 1.01, methanol) c In the production method of Reference Example 2c), R(+)−5−
[2-(acetylamino)propyl]-2-methoxybenzenesulfonamide instead of S(-)
-5-[2-(acetylamino)propyl]-2
-S using methoxybenzenesulfonamide
(+)-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide hydrochloride was obtained.
(i) 融点 273〜276℃（分解）
(ii) 元素分析値 （C10H17ClN2O3Sとして）
Ｃ Ｈ Ｎ
計算値(%) 42.78 6.10 9.98
実測値(%) 42.65 6.03 9.89
(iii) 比旋光度 〔α〕24 D6.0゜（ｃ＝1.01、メタ
ノ
ール）
実施例 １
２−（ｏ−エトキシフエノキシ）アセトアルデ
ヒド ジエチル アセタール（2.8ｇ）をアセト
ン（20ml）に溶解し、6N−塩酸（３ml）を加え
て室温で1.5時間撹拌する。溶媒留去して残渣に
水を加え析出油状物をエーテルで抽出し、抽出液
を水洗して無水硫酸ナトリウムで乾燥した後、溶
媒を留去して油状残渣を得た。残渣をメタノール
（100ml）に溶解し、Ｒ（−）−５−（２−アミノプ
ロピル）−２−メトキシベンゼンスルホンアミド
（2.4ｇ）を加えて１時間加熱還流した。冷後、酸
化白金（0.25ｇ）を加えて常温常圧で水素の吸収
が停止するまで還元した。触媒を別して液を
塩酸エタノールで酸性とし溶媒を留去し、残渣を
メタノールから再結晶してＲ（−）−５−［２−
［［２−（ｏ−エトキシフエノキシ）エチル］アミ
ノ］プロピル］−２−メトキシベンゼンスルホン
アミド塩酸塩2.1ｇを得た。 (i) Melting point 273-276℃ (decomposed) (ii) Elemental analysis value (as C 10 H 17 ClN 2 O 3 S) C H N Calculated value (%) 42.78 6.10 9.98 Actual value (%) 42.65 6.03 9.89 (iii ) Specific rotation [α] 24 D 6.0° (c = 1.01, methanol) Example 1 2-(o-ethoxyphenoxy)acetaldehyde diethyl acetal (2.8 g) was dissolved in acetone (20 ml), and 6N-hydrochloric acid (3 ml) and stirred at room temperature for 1.5 hours. The solvent was distilled off, water was added to the residue, the precipitated oil was extracted with ether, the extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain an oily residue. The residue was dissolved in methanol (100 ml), R(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (2.4 g) was added, and the mixture was heated under reflux for 1 hour. After cooling, platinum oxide (0.25 g) was added and the mixture was reduced at room temperature and pressure until hydrogen absorption stopped. The catalyst was separated, the solution was made acidic with hydrochloric acid and ethanol, the solvent was distilled off, and the residue was recrystallized from methanol to give R(-)-5-[2-
2.1 g of [[2-(o-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride was obtained.
融点 228〜230℃〔α〕24 D−4.1゜（メタノール）。 Melting point 228-230°C [α] 24 D -4.1° (methanol).
実施例 ２
実施例１と同様の方法でＲ（−）−５−（２−ア
ミノプロピル）−２−メトキシベンゼンスルホン
アミドの代りに、Ｓ（＋）−５−（２−アミノプロ
ピル）−２−メトキシベンゼンスルホンアミドを
用いてＳ（＋）−５−［２−［［２−（ｏ−エトキシフ
エノキシ）エチル］アミノ］プロピル］−２−メ
トキシベンゼンスルホンアミド塩酸塩を得た（収
率46％）。Example 2 In the same manner as in Example 1, S(+)-5-(2-aminopropyl)-2 was used instead of R(−)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide. -Methoxybenzenesulfonamide was used to obtain S(+)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride (harvested rate 46%).
融点 228〜230℃（メタノールより再結晶）。
〔α〕24 D＋4.1゜（メタノール）
実施例 ３
実施例１と同様の方法でＲ（−）−５−（２−ア
ミノプロピル）−２−メトキシベンゼンスルホン
アミドの代りにラセミ体の５−（２−アミノプロ
ピル）−２−メトキシベンゼンスルホンアミドを
用いて、ラセミ体の５−［２−［［２−（ｏ−エトキ
シフエノキシ）エチル］アミノ］プロピル］−２
−メトキシベンゼンスルホンアミド塩酸塩を得た
（収率49％）。融点254〜256℃（エタノールより再
結晶）。 Melting point: 228-230℃ (recrystallized from methanol).
[α] 24 D +4.1° (methanol) Example 3 In the same manner as in Example 1, racemic 5 was added instead of R(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide. -(2-Aminopropyl)-2-methoxybenzenesulfonamide was used to prepare racemic 5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]propyl]-2.
-Methoxybenzenesulfonamide hydrochloride was obtained (yield 49%). Melting point: 254-256℃ (recrystallized from ethanol).
実施例 ４
２−（ｏ−エトキシフエノキシ）アセトアルデ
ヒド ジエチル アセタール（2.8ｇ）をアセト
ン（20ml）に溶解し、6N−塩酸（３ml）を加え
て室温で1.5時間撹拌する。溶媒留去して残渣に
水を加え析出油状物をエーテルで抽出し、抽出液
を水洗して無水硫酸ナトリウムで乾燥した後、溶
媒を留去して油状残渣を得た。残渣をメタノール
（100ml）に溶解し、Ｒ（−）−５−（２−アミノプ
ロピル）−２−メトキシベンゼンスルホンアミド
（2.4ｇ）を加えて１時間加熱還流した。ついで、
５〜10℃で水素化ホウ素ナトリウム（0.42ｇ）を
１時間かけ徐々に加えて室温で１夜放置した。溶
媒留去して残渣を酢酸エチルで抽出し、抽出液を
水洗して無水硫酸ナトリウムで乾燥した後、溶媒
を留去した。残渣を塩酸エタノールで処理し、メ
タノールから再結晶してＲ（−）−５−［２−［［−
２（ｏ−エトキシフエノキシ）エチル］アミノ］
プロピル］−２−メトキシベンゼンスルホンアミ
ド塩酸塩1.6ｇを得た。融点228〜230℃。Example 4 2-(o-ethoxyphenoxy)acetaldehyde diethyl acetal (2.8 g) is dissolved in acetone (20 ml), 6N-hydrochloric acid (3 ml) is added, and the mixture is stirred at room temperature for 1.5 hours. The solvent was distilled off, water was added to the residue, the precipitated oil was extracted with ether, the extract was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain an oily residue. The residue was dissolved in methanol (100 ml), R(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (2.4 g) was added, and the mixture was heated under reflux for 1 hour. Then,
Sodium borohydride (0.42 g) was gradually added over 1 hour at 5 to 10°C, and the mixture was left at room temperature overnight. The solvent was distilled off, the residue was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was treated with hydrochloric acid and ethanol and recrystallized from methanol to give R(-)-5-[2-[[-
2(o-ethoxyphenoxy)ethyl]amino]
1.6 g of propyl]-2-methoxybenzenesulfonamide hydrochloride was obtained. Melting point 228-230℃.
〔α〕24 D−4.1゜（メタノール）。 [α] 24 D −4.1° (methanol).
実施例 ５
実施例４と同様の方法でＲ（−）−５−（２−ア
ミノプロピル）−２−メトキシベンゼンスルホン
アミドの代りにＳ（＋）−５−（２−アミノプロピ
ル）−２−メトキシベンゼンスルホンアミドを用
いてＳ（＋）−５−［２−［［２−（ｏ−エトキシフエ
ノキシ）エチル］プロピル］−２−メトキシベン
ゼンスルホンアミド塩酸塩を得た（収率37％）。
融点228〜230℃（メタノール）。〔α〕24 D＋4.1゜（メ
タノールより再結晶）。Example 5 In the same manner as in Example 4, S(+)-5-(2-aminopropyl)-2- was used instead of R(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide. Using methoxybenzenesulfonamide, S(+)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]propyl]-2-methoxybenzenesulfonamide hydrochloride was obtained (yield 37%). ).
Melting point 228-230℃ (methanol). [α] 24 D +4.1° (recrystallized from methanol).
Claims (1)
アルキル基を意味する。） で示されるフエネチルアミン誘導体と 式 （式中、R3は低級アルコキシ基を意味する。）
で示される置換フエノキシアセトアルデヒドとを
反応させ、反応生成物を還元することを特徴とす
る 式 （式中、R1，R2およびR3は上記の意味を示
す。） で示される置換フエネチルアミン誘導体またはそ
の塩の製造法。 ２ 式 で示されるフエネチルアミン誘導体がＲ（−）−５
−（２−アミノプロピル）−２−メトキシベンゼン
スルホンアミドまたはＳ（＋）−５−（２−アミノ
プロピル）−２−メトキシベンゼンスルホンアミ
ドである特許請求の範囲第１項記載の製造法。[Claims] 1 formula (In the formula, R 1 means a lower alkoxy group and R 2 means a lower alkyl group.) A phenethylamine derivative represented by the formula (In the formula, R 3 means a lower alkoxy group.)
characterized by reacting with a substituted phenoxyacetaldehyde represented by the formula and reducing the reaction product. (In the formula, R 1 , R 2 and R 3 have the above meanings.) A method for producing a substituted phenethylamine derivative or a salt thereof. 2 formulas The phenethylamine derivative represented by R(-)-5
-(2-aminopropyl)-2-methoxybenzenesulfonamide or S(+)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide, the manufacturing method according to claim 1.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254326A JPS62114952A (en) | 1985-11-13 | 1985-11-13 | Production of substituted phenethylamine derivative |
| KR1019860005460A KR940007746B1 (en) | 1985-11-13 | 1986-07-07 | Process for producing substituted phenethylamine derivatives |
| AT0203286A AT397960B (en) | 1985-11-13 | 1986-07-28 | METHOD FOR PRODUCING THE NEW R - (-) - 5- (2 - ((2- (O-ETHYXYPHENOXY) -THYL) -AMINO) - PROPYL) -2-METHOXYBENZENE SULPHONAMIDE |
| ES8600685A ES2000382A6 (en) | 1985-11-13 | 1986-07-29 | Production of substituted phenethylamine derivative |
| CA000515041A CA1282077C (en) | 1985-11-13 | 1986-07-31 | Process for producing substituted-phenethylamine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254326A JPS62114952A (en) | 1985-11-13 | 1985-11-13 | Production of substituted phenethylamine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62114952A JPS62114952A (en) | 1987-05-26 |
| JPH0137391B2 true JPH0137391B2 (en) | 1989-08-07 |
Family
ID=17263445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60254326A Granted JPS62114952A (en) | 1985-11-13 | 1985-11-13 | Production of substituted phenethylamine derivative |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS62114952A (en) |
| KR (1) | KR940007746B1 (en) |
| AT (1) | AT397960B (en) |
| CA (1) | CA1282077C (en) |
| ES (1) | ES2000382A6 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004093A1 (en) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | Process for producing optically active phenylpropylamine derivative |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971990A (en) * | 1988-02-19 | 1990-11-20 | Hokuriku Pharmaceutical Co., Ltd. | Phenoxyethylamine derivatives, for preparing the same and composition for exhibiting excellent α1 -blocking activity containing the same |
| US5288759A (en) * | 1992-08-27 | 1994-02-22 | Alcon Laboratories, Inc. | Use of certain sulfamoyl-substituted phenethylamine derivatives to reverse drug-induced mydriasis |
| TW536402B (en) | 1998-06-26 | 2003-06-11 | Yamanouchi Pharma Co Ltd | Pharmaceutical composition for the therapy of voiding dysfunction |
| KR100525493B1 (en) | 2001-02-23 | 2005-11-02 | 연성정밀화학(주) | Process for preparing sulfamoyl-substituted phenethylamine derivatives |
| CZ291802B6 (en) * | 2001-10-25 | 2003-05-14 | Léčiva, A.S. | Process for preparing (R)-(-)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzene sulfonamide |
| ES2200699B1 (en) * | 2002-07-12 | 2005-10-01 | Ragactives, S.L | PROCEDURE FOR THE SEPARATION OF R (-) AND S (+) - 5- (2 - ((2- (ETOXIFENOXI) ETIL) AMINO) PROPIL-2-METOXIBENCENO-SULFONAMIDE. |
| WO2004016582A1 (en) * | 2002-08-14 | 2004-02-26 | Natco Pharma Limited | An improved process for the preparation of tamsulosin hydrochloride |
| KR100503639B1 (en) | 2003-02-12 | 2005-07-26 | 보령제약 주식회사 | A purification process of Tamsulosin |
| US7329780B2 (en) | 2003-12-09 | 2008-02-12 | Cj Corporation | Method of preparing optically pure phenethylamine derivatives |
| SI21655A (en) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska dru�ba d.d. | Synthesis of optically pure (r)-5-(2-aminopropyl)-methoxybenzene sulphonamide |
| SI21656A (en) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska družba d.d. | Preparation of (r)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)-1-propyl)-2-methoxybenzene sulphonamide hydrochloride of high chemical purity |
| CZ2004197A3 (en) * | 2004-02-05 | 2005-08-17 | Zentiva, A. S. | Process for preparing (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide |
| US20080033208A1 (en) * | 2004-02-23 | 2008-02-07 | Dilipkumar Chandubhai Ramolia | Process for Manufacturing Optically Pure (R) or (S)-5-(2-Aminopropyl)-2-Methoxybenzene Sulfonamide |
| CN100545148C (en) | 2004-08-16 | 2009-09-30 | 神隆新加坡私人有限公司 | A kind of synthetic method of anti-BPH (benign prostatic hyperplasia) medicament Tamsulosin |
| WO2007031823A1 (en) * | 2005-09-12 | 2007-03-22 | Aurobindo Pharma Limited | An improved process for preparing tamsulosin hydrochloride |
| WO2008152653A2 (en) * | 2007-06-11 | 2008-12-18 | Matrix Laboratories Ltd | An improved process for the preparation of tamsulosin hydrochloride |
| UA102885C2 (en) | 2009-02-04 | 2013-08-27 | Астеллас Фарма Инк | Pharmaceutical composition for oral administration |
| EP2255793A1 (en) | 2009-05-28 | 2010-12-01 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising tamsulosin |
| JP5661773B2 (en) * | 2009-09-12 | 2015-01-28 | サンド・アクチエンゲゼルシヤフト | Process for the preparation of indoline derivatives and intermediates thereof |
| DE202023102187U1 (en) | 2023-04-25 | 2023-05-02 | Nusrath Anjum | Derivative formulation based on tamsulosin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
-
1985
- 1985-11-13 JP JP60254326A patent/JPS62114952A/en active Granted
-
1986
- 1986-07-07 KR KR1019860005460A patent/KR940007746B1/en not_active IP Right Cessation
- 1986-07-28 AT AT0203286A patent/AT397960B/en not_active IP Right Cessation
- 1986-07-29 ES ES8600685A patent/ES2000382A6/en not_active Expired
- 1986-07-31 CA CA000515041A patent/CA1282077C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004093A1 (en) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | Process for producing optically active phenylpropylamine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| AT397960B (en) | 1994-08-25 |
| ES2000382A6 (en) | 1988-02-16 |
| KR870004949A (en) | 1987-06-02 |
| KR940007746B1 (en) | 1994-08-24 |
| ATA203286A (en) | 1993-12-15 |
| CA1282077C (en) | 1991-03-26 |
| JPS62114952A (en) | 1987-05-26 |
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