FI66597C - Foerfarande foer framstaellning av en antiarrytmisk 4-hydroxi-3-metoxi-n-(2-(2-(1-metyl-2-piperidinyl)-etyl)fenyl)bensamidoch farmaceutisk godtagbara syraadditionssalter daerav - Google Patents
Foerfarande foer framstaellning av en antiarrytmisk 4-hydroxi-3-metoxi-n-(2-(2-(1-metyl-2-piperidinyl)-etyl)fenyl)bensamidoch farmaceutisk godtagbara syraadditionssalter daerav Download PDFInfo
- Publication number
- FI66597C FI66597C FI812873A FI812873A FI66597C FI 66597 C FI66597 C FI 66597C FI 812873 A FI812873 A FI 812873A FI 812873 A FI812873 A FI 812873A FI 66597 C FI66597 C FI 66597C
- Authority
- FI
- Finland
- Prior art keywords
- methoxy
- compound
- ethyl
- piperidinyl
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- -1 2- (2- (1-METHYL-2-PIPERIDINYL) -ETHYL) PHENYL Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- VRJLWFYHYPQLLO-UHFFFAOYSA-N 3-methoxy-4-phenylmethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC=C1OCC1=CC=CC=C1 VRJLWFYHYPQLLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- CCXFKJBMYLLRBW-UHFFFAOYSA-N 2-[2-(1-methylpiperidin-2-yl)ethyl]aniline Chemical compound CN1CCCCC1CCC1=CC=CC=C1N CCXFKJBMYLLRBW-UHFFFAOYSA-N 0.000 claims 1
- 230000002763 arrhythmic effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 19
- PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical class C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 description 16
- 229960001142 encainide Drugs 0.000 description 12
- 239000000126 substance Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- 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 5
- 241000282412 Homo Species 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 206010003119 arrhythmia Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 description 2
- AZUVBPVDRHGGEP-UHFFFAOYSA-N 6a,9a-dimethyl-4,5,7,8,9,9a-hexahydro-6aH-dipyrrolo(2,3-b;3',2',1'-hi)indole Natural products CC(=C)C1CCC(C)=CCCC(C)=CCCC(C)=CC1O AZUVBPVDRHGGEP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- VRCBZHVFFCLTKF-UHFFFAOYSA-N NC1=C(C=CC=C1)CCC1N(CCCC1)C.NC1=C(C=CC=C1)CCC1N(CCCC1)C Chemical compound NC1=C(C=CC=C1)CCC1N(CCCC1)C.NC1=C(C=CC=C1)CCC1N(CCCC1)C VRCBZHVFFCLTKF-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 206010033546 Pallor Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000004776 neurological deficiency Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI832932A FI73086C (fi) | 1980-09-18 | 1983-08-15 | Foerfarande foer kvantitativ bestaemning av enkainid och dess 0-demetyl- och 3-metoxi-0-demetyl- -aemnesomsaettningsprodukter i biologisk vaetska. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18818480 | 1980-09-18 | ||
| US06/188,184 US4332803A (en) | 1980-09-18 | 1980-09-18 | Benzanilide derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI812873L FI812873L (fi) | 1982-03-19 |
| FI66597B FI66597B (fi) | 1984-07-31 |
| FI66597C true FI66597C (fi) | 1984-11-12 |
Family
ID=22692080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI812873A FI66597C (fi) | 1980-09-18 | 1981-09-15 | Foerfarande foer framstaellning av en antiarrytmisk 4-hydroxi-3-metoxi-n-(2-(2-(1-metyl-2-piperidinyl)-etyl)fenyl)bensamidoch farmaceutisk godtagbara syraadditionssalter daerav |
Country Status (25)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4618680A (en) * | 1980-09-18 | 1986-10-21 | Mead Johnson & Company | Benzanilide derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA961038A (en) * | 1971-03-03 | 1975-01-14 | Joseph L. Minielli | Substituted piperidines |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
-
1980
- 1980-09-18 US US06/188,184 patent/US4332803A/en not_active Expired - Lifetime
-
1981
- 1981-09-08 CY CY137081A patent/CY1370A/en unknown
- 1981-09-08 GB GB8127079A patent/GB2084570B/en not_active Expired
- 1981-09-11 YU YU2192/81A patent/YU42425B/xx unknown
- 1981-09-11 AU AU75181/81A patent/AU526825B2/en not_active Ceased
- 1981-09-14 ZA ZA816348A patent/ZA816348B/xx unknown
- 1981-09-15 FI FI812873A patent/FI66597C/fi not_active IP Right Cessation
- 1981-09-15 NL NL8104261A patent/NL8104261A/nl not_active Application Discontinuation
- 1981-09-15 FR FR8117391A patent/FR2494267B1/fr not_active Expired
- 1981-09-16 DK DK412881A patent/DK152121C/da not_active IP Right Cessation
- 1981-09-17 IT IT8149311A patent/IT1209900B/it active
- 1981-09-17 GR GR66079A patent/GR75788B/el unknown
- 1981-09-17 IE IE2160/81A patent/IE51584B1/en not_active IP Right Cessation
- 1981-09-17 DE DE3137084A patent/DE3137084C2/de not_active Expired
- 1981-09-17 DE DE3153300A patent/DE3153300C2/de not_active Expired
- 1981-09-17 CH CH90/85A patent/CH651932A5/de not_active IP Right Cessation
- 1981-09-17 CH CH6017/81A patent/CH650497A5/de not_active IP Right Cessation
- 1981-09-18 AT AT0403781A patent/AT378181B/de active
- 1981-09-18 CA CA000386216A patent/CA1183537A/en not_active Expired
- 1981-09-18 BE BE0/206007A patent/BE890418A/fr not_active IP Right Cessation
- 1981-09-18 JP JP56146406A patent/JPS5782368A/ja active Granted
- 1981-09-18 LU LU83644A patent/LU83644A1/fr unknown
- 1981-09-18 AR AR286799A patent/AR227065A1/es active
- 1981-09-18 SE SE8105538A patent/SE445215B/sv not_active IP Right Cessation
-
1984
- 1984-02-02 GB GB08402839A patent/GB2144050B/en not_active Expired
- 1984-02-02 CY CY137784A patent/CY1377A/en unknown
-
1987
- 1987-03-27 SG SG301/87A patent/SG30187G/en unknown
- 1987-03-31 KE KE3716A patent/KE3716A/xx unknown
- 1987-03-31 KE KE3717A patent/KE3717A/xx unknown
-
1988
- 1988-01-21 HK HK53/88A patent/HK5388A/xx unknown
- 1988-01-21 HK HK44/88A patent/HK4488A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0043807B1 (en) | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates | |
| BG63992B1 (bg) | Амидно съединение и приложение му като rho киназен инхибитор | |
| JPH01203400A (ja) | アデノシン誘導体 | |
| JP5072604B2 (ja) | １−［３−［３−（４−クロロフェニル）プロポキシ］プロピル］−ピペリジン一塩酸塩 | |
| JP2656594B2 (ja) | ジアミン化合物、その製法及び該化合物を含有する高血圧症及び炎症を治療するための医薬 | |
| JP3093419B2 (ja) | １，４‐ベンゾチアゼピン誘導体 | |
| KR900000887B1 (ko) | 질산염 유도체의 제조방법 | |
| US4461775A (en) | Hydroxythioether fatty acid derivatives | |
| FI66597C (fi) | Foerfarande foer framstaellning av en antiarrytmisk 4-hydroxi-3-metoxi-n-(2-(2-(1-metyl-2-piperidinyl)-etyl)fenyl)bensamidoch farmaceutisk godtagbara syraadditionssalter daerav | |
| US4794115A (en) | Method of treating hyperlipemia | |
| US4000192A (en) | Pharmacologically active compounds | |
| NZ204072A (en) | Pharmaceutical compositions which contain theophylline as active ingredient | |
| US4503058A (en) | Therapeutically useful 3,7a-diazacyclohepta[j,k]fluorene derivatives | |
| US4618680A (en) | Benzanilide derivative | |
| JPS61500437A (ja) | ｎ−プロパノ−ルアミン誘導体のエ−テル | |
| JPH02258749A (ja) | ポリヒドロキシベンジルオキシプロパノールアミン | |
| EP0460358B1 (en) | Agent for treating disorders from cerebral neuro-degeneration | |
| US4474707A (en) | N-3-Propenylaminopropyl-N'-phenylureas | |
| JPH04503216A (ja) | 癲癇およびコカイン嗜癖治療用の５―アミノカルボニル―５Ｈ―ジベンゾ〔ａ，ｄ〕シクロヘプテン―５，１０―イミン | |
| FI65060C (fi) | Foerfarande foer framstaellning av 4-metoxi-n-(2-(2-(1-metyl-2-piperidyl)etyl)fenyl)-bensamid-n-oxid som haemmar rytmstoerningar i hjaertat | |
| JP2694321B2 (ja) | インターロイキン−１阻害剤 | |
| JPH04270222A (ja) | 脳機能改善剤 | |
| US4933459A (en) | Pharmaceuticals containing acylated benzilic acid derivatives for influencing the tone of the urinary bladder | |
| WO1995003291A1 (en) | Novel substituted 1-propene derivatives, pharmaceutical compositions containing them and process for preparing same | |
| JPS6110558A (ja) | 新規なデカハイドロキノリノール誘導体、その製造法及び医薬 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BRISTOL-MYERS CO |