JPS6252742B2 - - Google Patents
Info
- Publication number
- JPS6252742B2 JPS6252742B2 JP55014382A JP1438280A JPS6252742B2 JP S6252742 B2 JPS6252742 B2 JP S6252742B2 JP 55014382 A JP55014382 A JP 55014382A JP 1438280 A JP1438280 A JP 1438280A JP S6252742 B2 JPS6252742 B2 JP S6252742B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ethyl
- compound
- lower alkyl
- ethylamino
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- -1 sulfamoyl-substituted phenethylamine Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 2
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IOYHGBZPUZBUTJ-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1OCCBr IOYHGBZPUZBUTJ-UHFFFAOYSA-N 0.000 description 1
- ZZIZZTHXZRDOFM-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)ethyl-[1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-UHFFFAOYSA-N 0.000 description 1
- LWXYQRNOFGGUMR-UHFFFAOYSA-N 2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1S(N)(=O)=O LWXYQRNOFGGUMR-UHFFFAOYSA-N 0.000 description 1
- ORSXTVBUTKCATA-UHFFFAOYSA-N 5-[1-chloro-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OCCNCC(Cl)C1=CC=C(OC)C(S(N)(=O)=O)=C1 ORSXTVBUTKCATA-UHFFFAOYSA-N 0.000 description 1
- GNMVUBZCLZMGIL-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OCCNCC(O)C1=CC=C(OC)C(S(N)(=O)=O)=C1 GNMVUBZCLZMGIL-UHFFFAOYSA-N 0.000 description 1
- UZJKHENMEHYKDG-UHFFFAOYSA-N 5-[2-[2-(2-ethoxyphenoxy)ethylamino]-1-hydroxyethyl]-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNCC(O)C1=CC=C(OC)C(S(N)(=O)=O)=C1 UZJKHENMEHYKDG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000003042 antagnostic effect Effects 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 238000010998 test method Methods 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/10—Radicals substituted by singly bound oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (32)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1438280A JPS56110665A (en) | 1980-02-08 | 1980-02-08 | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| AR283989A AR227533A1 (es) | 1980-02-08 | 1981-01-19 | Un procedimiento para producir derivados fenetilaminicos sufamoil sustituidos |
| CA000369230A CA1177849A (en) | 1980-02-08 | 1981-01-23 | Process of producing sulfamoyl-substituted phenethylamine derivatives |
| DE8181300431T DE3163257D1 (en) | 1980-02-08 | 1981-02-02 | Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them |
| EP81300431A EP0034432B1 (en) | 1980-02-08 | 1981-02-02 | Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them |
| AT81300431T ATE7223T1 (de) | 1980-02-08 | 1981-02-02 | Durch sulfamoylgruppen substituierte phenethylamin-derivate, ihre herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
| DE1996175042 DE19675042I2 (de) | 1980-02-08 | 1981-02-02 | Durch Sulfamoylgruppen substituierte Phenethylamin-Derivate ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| AU66896/81A AU541720B2 (en) | 1980-02-08 | 1981-02-04 | Sulphonamide phenethyl amine derivatives and process of producing them |
| GR64051A GR73827B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-08 | 1981-02-04 | |
| US06/231,421 US4373106A (en) | 1980-02-08 | 1981-02-04 | Sulfamoyl-substituted phenethylamine derivatives and process of producing them |
| PT72460A PT72460B (en) | 1980-02-08 | 1981-02-05 | Process for preparing sulfamoyl-substituted phenethylamine de- rivatives |
| UA3382004A UA5990A1 (uk) | 1980-02-08 | 1981-02-06 | Спосіб одержання сульфамоілзаміщених похідних фенетіламіна або його солянокислої солі |
| UA3245545A UA5980A1 (uk) | 1980-02-08 | 1981-02-06 | Спосіб одержання сульфаілзаміщаних похідних фенетіламіна, а також їх кислотно-адитивних солей |
| SU813245545A SU1082320A3 (ru) | 1980-02-08 | 1981-02-06 | Способ получени сульфамоилзамещенных производных фенэтиламина,а также их кислотно-аддитивных солей |
| UA3379949A UA5981A1 (uk) | 1980-02-08 | 1981-02-06 | Спосіб одержання сульфамоілзаміщеного похідного фенетіламіна і його кислотної солі |
| ES499224A ES499224A0 (es) | 1980-02-08 | 1981-02-06 | Un procedimiento de produccion de derivados de fenetilamina sulfamoil-sustituidos |
| IE236/81A IE50862B1 (en) | 1980-02-08 | 1981-02-06 | Sulfamoyl-substituted phenethylamine derivatives,their preparation and pharmaceutical compositions containing them |
| MX819298U MX6859E (es) | 1980-02-08 | 1981-02-09 | Procedimiento para producir derivados de fenetilamina substituidos por sulfamoilo |
| SU823379949A SU1181540A3 (ru) | 1980-02-08 | 1982-01-21 | Способ получени сульфамоилзамещенного производного фенэтиламина и его кислотной соли |
| SU823382004A SU1248533A3 (ru) | 1980-02-08 | 1982-01-29 | Способ получени сульфамоилзамещенных производных фенэтиламина или его сол нокислой соли |
| AR288580A AR230433A1 (es) | 1980-02-08 | 1982-02-26 | Procedimiento para producir derivados fenetilaminicos sulfamoil sustituidos |
| US06/632,258 US4558156A (en) | 1980-02-08 | 1984-07-18 | Sulfamoyl-substituted phenethylamine derivatives |
| US06/756,790 US4703063A (en) | 1980-02-08 | 1985-07-18 | Sulfamoyl substituted phenethylamine derivatives and process of producing them |
| US06/803,204 US4731478A (en) | 1980-02-08 | 1985-11-27 | Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them |
| US06/828,052 US4761500A (en) | 1980-02-08 | 1986-02-10 | Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them |
| US07/311,366 US4868216A (en) | 1980-02-08 | 1989-02-14 | Sulfamoyl-substituted phenethylamine derivatives and process of producing them |
| US07/436,125 US4987152A (en) | 1980-02-08 | 1989-11-13 | Use of sulfamoyl-substituted phenethylamine derivatives in treatment of lower urinary tract dysfunction |
| MX9203592A MX9203592A (es) | 1980-02-08 | 1992-06-26 | Derivados de sulfamoil-fenetilamina substituida. |
| US08/174,608 US5391825A (en) | 1980-02-08 | 1993-12-28 | Sulfamoyl substituted phenethylamine intermediates |
| US08/314,322 US5447958A (en) | 1980-02-08 | 1994-09-28 | Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them |
| NL950014C NL950014I2 (nl) | 1980-02-08 | 1995-08-18 | Met sulfamoyl gesubstitueerde fenetylaminederivaten, de bereiding daarvan en farmaceutische preparaten, die deze derivaten bevatten. |
| LU90000C LU90000I2 (fr) | 1980-02-08 | 1997-01-03 | Omic |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1438280A JPS56110665A (en) | 1980-02-08 | 1980-02-08 | Sulfamoyl-substituted phenetylamine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56110665A JPS56110665A (en) | 1981-09-01 |
| JPS6252742B2 true JPS6252742B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-11-06 |
Family
ID=11859488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1438280A Granted JPS56110665A (en) | 1980-02-08 | 1980-02-08 | Sulfamoyl-substituted phenetylamine derivative and its preparation |
Country Status (17)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006004093A1 (ja) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | 光学活性フェニルプロピルアミン誘導体の製法 |
| JP2008523039A (ja) * | 2004-12-06 | 2008-07-03 | ホビオネ インテル リミテッド | タムスロシンの製造方法及びその中間体 |
Families Citing this family (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391825A (en) * | 1980-02-08 | 1995-02-21 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl substituted phenethylamine intermediates |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| EP0091749A3 (en) * | 1982-04-08 | 1984-12-05 | Beecham Group Plc | Ethanolamine derivatives, process for their preparation and pharmaceutical compositions containing them |
| US4772475A (en) * | 1985-03-08 | 1988-09-20 | Yamanouchi Pharmaceutical Co., Ltd. | Controlled-release multiple units pharmaceutical formulation |
| JPS62114952A (ja) * | 1985-11-13 | 1987-05-26 | Yamanouchi Pharmaceut Co Ltd | 置換フエネチルアミン誘導体の製造法 |
| JPH066565B2 (ja) * | 1986-07-21 | 1994-01-26 | 山之内製薬株式会社 | 光学活性なベンゼンスルホンアミド誘導体の製造法 |
| 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 |
| IE64061B1 (en) * | 1989-09-04 | 1995-07-12 | Yamanouchi Pharma Co Ltd | External preparation containing amusulosin |
| US5288759A (en) * | 1992-08-27 | 1994-02-22 | Alcon Laboratories, Inc. | Use of certain sulfamoyl-substituted phenethylamine derivatives to reverse drug-induced mydriasis |
| CA2166812A1 (en) * | 1993-07-14 | 1995-01-26 | Masaharu Asano | Agent for treating urinary outlet obstruction associated with benign prostatic hyperplasia |
| US5863949A (en) * | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| FR2737494B1 (fr) * | 1995-08-04 | 1997-08-29 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leur application en therapeutique |
| US6177430B1 (en) | 1997-03-27 | 2001-01-23 | Pfizer Inc | Use of α1-adrenoreceptor antagonists in the prevention and treatment of benign prostatic hyperplasia |
| WO1997038593A1 (en) * | 1996-04-12 | 1997-10-23 | Beth Israel Deaconess Medical Center, Inc. | Diabetic supplement bar |
| US6410554B1 (en) | 1998-03-23 | 2002-06-25 | Merck & Co., Inc. | Combination therapy for the treatment of benign prostatic hyperplasia |
| WO1999057131A1 (en) * | 1998-05-06 | 1999-11-11 | Duke University | Method of treating bladder and lower urinary tract syndromes |
| TW536402B (en) | 1998-06-26 | 2003-06-11 | Yamanouchi Pharma Co Ltd | Pharmaceutical composition for the therapy of voiding dysfunction |
| AU758802B2 (en) | 1998-09-30 | 2003-03-27 | Takeda Pharmaceutical Company Limited | Drugs for improving vesical excretory strength |
| CA2370501C (en) * | 1999-08-09 | 2008-09-16 | Yamanouchi Pharmaceutical Co., Ltd. | Pharmaceutical composition for the therapy of lower urinary tract symptoms |
| IL141235A (en) * | 2000-02-09 | 2012-04-30 | Novartis Int Pharm Ltd | Combined use of an alpha-adrenoceptor antagonist and a muscarinic antagonist in the preparation of a drug for the treatment of non-malignant prostatic hyperplasia |
| US20020035107A1 (en) | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| US20020065286A1 (en) * | 2000-08-21 | 2002-05-30 | Davies Michael John | Treatment of wounds |
| US20020091129A1 (en) * | 2000-11-20 | 2002-07-11 | Mitradev Boolell | Treatment of premature ejaculation |
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| WO2006004093A1 (ja) * | 2004-07-07 | 2006-01-12 | Hamari Chemicals, Ltd. | 光学活性フェニルプロピルアミン誘導体の製法 |
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