HRP920600A2 - Novel polystyrenesulfonate - Google Patents
Novel polystyrenesulfonate Download PDFInfo
- Publication number
- HRP920600A2 HRP920600A2 HR920600A HRP920600A HRP920600A2 HR P920600 A2 HRP920600 A2 HR P920600A2 HR 920600 A HR920600 A HR 920600A HR P920600 A HRP920600 A HR P920600A HR P920600 A2 HRP920600 A2 HR P920600A2
- Authority
- HR
- Croatia
- Prior art keywords
- salt
- ethyl
- benzonitrile
- propyl
- amino
- Prior art date
Links
- 229920001467 poly(styrenesulfonates) Polymers 0.000 title description 5
- 229960002796 polystyrene sulfonate Drugs 0.000 title description 4
- 239000011970 polystyrene sulfonate Substances 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 15
- ZMHOBBKJBYLXFR-BPNWFJGMSA-N 4-[(2r)-3-[ethyl(3-propylsulfinylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCS(=O)CCCN(CC)C[C@@H](O)COC1=CC=C(C#N)C=C1 ZMHOBBKJBYLXFR-BPNWFJGMSA-N 0.000 claims abstract description 8
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 17
- 229940005642 polystyrene sulfonic acid Drugs 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 2
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 4-[3-[ethyl[3-(propylsulfinyl)propyl]amino]-2(R)-hydroxypropoxy]-benzonitrile 4-[3-[ethyl[3-(propylsulfinyl)propyl]amino]-2(S)-hydroxypropoxy]-benzonitrile Chemical compound 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- ZMHOBBKJBYLXFR-KEJDIYNNSA-N 4-[(2s)-3-[ethyl(3-propylsulfinylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCS(=O)CCCN(CC)C[C@H](O)COC1=CC=C(C#N)C=C1 ZMHOBBKJBYLXFR-KEJDIYNNSA-N 0.000 description 2
- BNIJSWPESWZPCF-UHFFFAOYSA-N 4-[3-[ethyl(3-propylsulfanylpropyl)amino]-2-hydroxypropoxy]benzonitrile Chemical compound CCCSCCCN(CC)CC(O)COC1=CC=C(C#N)C=C1 BNIJSWPESWZPCF-UHFFFAOYSA-N 0.000 description 2
- WREXVDPOLDOXJL-JTQLQIEISA-N 4-[[(2r)-oxiran-2-yl]methoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OC[C@@H]1OC1 WREXVDPOLDOXJL-JTQLQIEISA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- WZMVRBZTVVOICZ-JTQLQIEISA-N [(2s)-3-(4-cyanophenoxy)-2-hydroxypropyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)COC1=CC=C(C#N)C=C1 WZMVRBZTVVOICZ-JTQLQIEISA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- IUSOXUFUXZORBF-UHFFFAOYSA-N n,n-dioctyloctan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC IUSOXUFUXZORBF-UHFFFAOYSA-N 0.000 description 1
- MNZUQICTERRLAY-UHFFFAOYSA-N n-ethyl-3-propylsulfinylpropan-1-amine Chemical compound CCCS(=O)CCCNCC MNZUQICTERRLAY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940006186 sodium polystyrene sulfonate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/795—Polymers containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
- A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8902236A SE8902236D0 (sv) | 1989-06-20 | 1989-06-20 | Novel polystyrenesulfonate |
| YU120590A YU120590A (sh) | 1989-06-20 | 1990-06-20 | Novi polistirolsulfonat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP920600A2 true HRP920600A2 (en) | 1994-08-31 |
Family
ID=20376341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR920600A HRP920600A2 (en) | 1989-06-20 | 1992-09-29 | Novel polystyrenesulfonate |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5068272A (ru) |
| EP (1) | EP0404747B1 (ru) |
| JP (1) | JPH04506213A (ru) |
| KR (1) | KR920702675A (ru) |
| CN (1) | CN1048220A (ru) |
| AT (1) | ATE88463T1 (ru) |
| AU (1) | AU641671B2 (ru) |
| BG (1) | BG51351A3 (ru) |
| CA (1) | CA2059282A1 (ru) |
| DD (1) | DD295158A5 (ru) |
| DE (1) | DE69001397T2 (ru) |
| DK (1) | DK0404747T3 (ru) |
| ES (1) | ES2054324T3 (ru) |
| FI (1) | FI915936A0 (ru) |
| HR (1) | HRP920600A2 (ru) |
| HU (1) | HUT59086A (ru) |
| IE (1) | IE902160A1 (ru) |
| IL (1) | IL94676A0 (ru) |
| LT (1) | LTIP1724A (ru) |
| MX (1) | MX21203A (ru) |
| NO (1) | NO914928D0 (ru) |
| NZ (1) | NZ234022A (ru) |
| PL (1) | PL163537B1 (ru) |
| PT (1) | PT94416A (ru) |
| RU (1) | RU2004539C1 (ru) |
| SE (1) | SE8902236D0 (ru) |
| WO (1) | WO1990015793A1 (ru) |
| YU (1) | YU120590A (ru) |
| ZA (1) | ZA904412B (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8705150D0 (sv) * | 1987-12-23 | 1987-12-23 | Haessle Ab | Novel antiarrhythmic agents |
| SE8902235D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel cyclodextrin inclusion complexes |
| SE9003902D0 (sv) * | 1990-12-07 | 1990-12-07 | Astra Ab | Solid dosage forms of a drug |
| US6290946B1 (en) | 1999-05-13 | 2001-09-18 | Geltex Pharmaceuticals, Inc. | Anionic polymers as toxin binders and antibacterial agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1457876A (en) * | 1972-12-15 | 1976-12-08 | Ici Ltd | Alkanolamine derivatives device for use in |
| GB1433920A (en) * | 1973-10-01 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
| SE8705150D0 (sv) * | 1987-12-23 | 1987-12-23 | Haessle Ab | Novel antiarrhythmic agents |
| SE8902235D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel cyclodextrin inclusion complexes |
| SE8902237D0 (sv) * | 1989-06-20 | 1989-06-20 | Haessle Ab | Novel stereoisomers |
-
1989
- 1989-06-20 SE SE8902236A patent/SE8902236D0/xx unknown
-
1990
- 1990-06-07 ZA ZA904412A patent/ZA904412B/xx unknown
- 1990-06-08 IL IL94676A patent/IL94676A0/xx unknown
- 1990-06-12 NZ NZ234022A patent/NZ234022A/en unknown
- 1990-06-15 CN CN90104475A patent/CN1048220A/zh active Pending
- 1990-06-15 IE IE216090A patent/IE902160A1/en unknown
- 1990-06-16 DD DD90341730A patent/DD295158A5/de not_active IP Right Cessation
- 1990-06-18 US US07/539,863 patent/US5068272A/en not_active Expired - Fee Related
- 1990-06-18 MX MX2120390A patent/MX21203A/es unknown
- 1990-06-19 WO PCT/SE1990/000437 patent/WO1990015793A1/en active Application Filing
- 1990-06-19 PT PT94416A patent/PT94416A/pt not_active Application Discontinuation
- 1990-06-19 DE DE90850242T patent/DE69001397T2/de not_active Expired - Fee Related
- 1990-06-19 ES ES90850242T patent/ES2054324T3/es not_active Expired - Lifetime
- 1990-06-19 CA CA002059282A patent/CA2059282A1/en not_active Abandoned
- 1990-06-19 DK DK90850242.0T patent/DK0404747T3/da active
- 1990-06-19 JP JP2509478A patent/JPH04506213A/ja active Pending
- 1990-06-19 EP EP90850242A patent/EP0404747B1/en not_active Expired - Lifetime
- 1990-06-19 HU HU905546A patent/HUT59086A/hu unknown
- 1990-06-19 AU AU59377/90A patent/AU641671B2/en not_active Ceased
- 1990-06-19 AT AT90850242T patent/ATE88463T1/de not_active IP Right Cessation
- 1990-06-19 KR KR1019910701913A patent/KR920702675A/ko not_active Application Discontinuation
- 1990-06-20 PL PL90285700A patent/PL163537B1/pl unknown
- 1990-06-20 YU YU120590A patent/YU120590A/sh unknown
-
1991
- 1991-12-13 NO NO914928A patent/NO914928D0/no unknown
- 1991-12-17 FI FI915936A patent/FI915936A0/fi not_active Application Discontinuation
- 1991-12-19 RU SU915010861A patent/RU2004539C1/ru active
- 1991-12-20 BG BG95669A patent/BG51351A3/xx unknown
-
1992
- 1992-09-29 HR HR920600A patent/HRP920600A2/hr not_active Application Discontinuation
-
1993
- 1993-12-30 LT LTIP1724A patent/LTIP1724A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0404747B1 (en) | 1993-04-21 |
| IE902160L (en) | 1990-12-20 |
| PL163537B1 (pl) | 1994-04-29 |
| DE69001397D1 (de) | 1993-05-27 |
| ES2054324T3 (es) | 1994-08-01 |
| ZA904412B (en) | 1991-02-27 |
| EP0404747A1 (en) | 1990-12-27 |
| US5068272A (en) | 1991-11-26 |
| DK0404747T3 (da) | 1993-08-23 |
| PT94416A (pt) | 1991-02-08 |
| AU5937790A (en) | 1991-01-08 |
| CN1048220A (zh) | 1991-01-02 |
| WO1990015793A1 (en) | 1990-12-27 |
| DE69001397T2 (de) | 1994-03-17 |
| NZ234022A (en) | 1992-05-26 |
| SE8902236D0 (sv) | 1989-06-20 |
| JPH04506213A (ja) | 1992-10-29 |
| IE902160A1 (en) | 1991-01-02 |
| NO914928L (no) | 1991-12-13 |
| ATE88463T1 (de) | 1993-05-15 |
| BG51351A3 (en) | 1993-04-15 |
| DD295158A5 (de) | 1991-10-24 |
| NO914928D0 (no) | 1991-12-13 |
| CA2059282A1 (en) | 1990-12-21 |
| RU2004539C1 (ru) | 1993-12-15 |
| HUT59086A (en) | 1992-04-28 |
| LTIP1724A (en) | 1995-07-25 |
| FI915936A0 (fi) | 1991-12-17 |
| IL94676A0 (en) | 1991-04-15 |
| YU120590A (sh) | 1992-07-20 |
| MX21203A (es) | 1993-11-01 |
| KR920702675A (ko) | 1992-10-06 |
| AU641671B2 (en) | 1993-09-30 |
| HU905546D0 (en) | 1992-03-30 |
| PL285700A1 (en) | 1991-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL71423B1 (en) | Alkanolamine Derivatives[GB1199037A] | |
| AU658188B2 (en) | Phellodendrine analogs and allergy type IV suppressor containing the same as active ingredient | |
| NZ242626A (en) | Substituted carboxylic acid derivatives, preparation and pharmaceutical compositions thereof | |
| JPS6112907B2 (ru) | ||
| CH631164A5 (de) | Verfahren zur herstellung von neuem 1-cyclopropylmethyl-4-(3-jod-5h-dibenzo(a,d)cyclohepten-5-yliden)piperidin. | |
| HRP920600A2 (en) | Novel polystyrenesulfonate | |
| JPS6216942B2 (ru) | ||
| US4315862A (en) | Process for preparing cannabichromene | |
| DE3625738A1 (de) | 2-acyloxypropylamin-derivate, verfahren zu deren herstellung und deren verwendung | |
| US3344188A (en) | d (-)-n-tert.butyl- and -n-isopropyl-1-phenyl-2-amino-ethanols | |
| US2744916A (en) | Phenyl-substituted salicylamides | |
| DD210051A5 (de) | Verfahren zur darstellung eines neuen thienopyridinon-derivats | |
| CA1209995A (fr) | Procede pour la preparation de composes de nicotinamide 1-oxyde n-substitue et de ses sels, et les composes et sels ainsi obtenus | |
| CH642348A5 (de) | Alkylthiophenoxyalkylamine. | |
| DD297404A5 (de) | Verfahren zur herstellung eines salzes der verbindung 4-[3-[ethyl-(3-(propylsulfinyl)-propyl]-amino)-2-hydroxy-propoxy]-benzonitril | |
| US2930731A (en) | Bis[beta-(ortho-hydrocarbonoxyphenyl)iso-propyl]amines | |
| US3723514A (en) | (-)threo-3-(4-hydroxy-3-methoxyphenyl)-serine | |
| HRP920625A2 (en) | Novel stereoisomers | |
| DE112020001032T5 (de) | Verfahren zur Herstellung von Levoamphetamin | |
| JPS6026387B2 (ja) | シンナミルモラノリン誘導体 | |
| AT371448B (de) | Verfahren zur herstellung von neuen cis-4a-phenyl -isochinolin-derivaten und ihren saeureadditionssalzen | |
| US2537004A (en) | Citric acid salts and their preparation | |
| JPS6032628B2 (ja) | シクロヘキサノール誘導体 | |
| EP0303179A1 (de) | Neue 1,2-Diamino-Verbindungen, Verfahren zu ihrer Herstellung sowie Arzneimittel, die diese Verbindungen enthalten | |
| AT234676B (de) | Verfahren zur Herstellung von 7-Methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrenverbindungen, welche in 2-Stellung die Carbamylgruppe oder eine substituierte Carbamylgruppe aufweisen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ODBC | Application rejected |