JPH0526785B2 - - Google Patents
Info
- Publication number
- JPH0526785B2 JPH0526785B2 JP2099083A JP2099083A JPH0526785B2 JP H0526785 B2 JPH0526785 B2 JP H0526785B2 JP 2099083 A JP2099083 A JP 2099083A JP 2099083 A JP2099083 A JP 2099083A JP H0526785 B2 JPH0526785 B2 JP H0526785B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- hydrogen atom
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002213 calciumantagonistic effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical class C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 229940127291 Calcium channel antagonist Drugs 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- -1 2-(substituted phenyl)-3-oxo-1,4-benzothiazine Chemical class 0.000 description 2
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical group C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- KTACZRWRTSQVNO-UHFFFAOYSA-N 1-phenyl-2-piperazin-1-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CN1CCNCC1 KTACZRWRTSQVNO-UHFFFAOYSA-N 0.000 description 1
- SYVCKMPYVANGHB-UHFFFAOYSA-N 2-(2-hydroxy-5-methoxyphenyl)-4h-1,4-benzothiazin-3-one Chemical compound COC1=CC=C(O)C(C2C(NC3=CC=CC=C3S2)=O)=C1 SYVCKMPYVANGHB-UHFFFAOYSA-N 0.000 description 1
- IQQIFITXYZKQGW-UHFFFAOYSA-N 2-[2-[2-hydroxy-3-(4-phenacylpiperazin-1-yl)propoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one Chemical compound S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCC(O)CN(CC1)CCN1CC(=O)C1=CC=CC=C1 IQQIFITXYZKQGW-UHFFFAOYSA-N 0.000 description 1
- AOAPIDJXLXNCMX-UHFFFAOYSA-N 2-[2-[4-[cyclohexyl(methyl)amino]butoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one Chemical compound S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCCN(C)C1CCCCC1 AOAPIDJXLXNCMX-UHFFFAOYSA-N 0.000 description 1
- BKWPBVOSVCRBQF-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)propoxy]phenyl]-4-methyl-1,4-benzothiazin-3-one Chemical compound C1=CC(OCCCN(C)C)=CC=C1C1C(=O)N(C)C2=CC=CC=C2S1 BKWPBVOSVCRBQF-UHFFFAOYSA-N 0.000 description 1
- LQMDSAHJHYIZFJ-UHFFFAOYSA-N 2-[5-methoxy-2-(oxiran-2-ylmethoxy)phenyl]-4h-1,4-benzothiazin-3-one Chemical compound S1C2=CC=CC=C2NC(=O)C1C1=CC(OC)=CC=C1OCC1CO1 LQMDSAHJHYIZFJ-UHFFFAOYSA-N 0.000 description 1
- DLALSZUJBMNOHZ-UHFFFAOYSA-N 2-phenyl-4h-1,4-benzothiazin-3-one Chemical class O=C1NC2=CC=CC=C2SC1C1=CC=CC=C1 DLALSZUJBMNOHZ-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000036982 action potential Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58020990A JPS59148771A (ja) | 1983-02-09 | 1983-02-09 | ベンゾチアジン誘導体 |
| US06/571,467 US4584300A (en) | 1983-02-07 | 1984-01-17 | Platelet anti-aggregative- and calcium antagonistic -1,4-benzothiazin-3-one derivatives, compositions, and methods of use therefor |
| CA000445634A CA1245650A (en) | 1983-02-07 | 1984-01-19 | Processes for preparing novel benzothiazine derivatives |
| AU23767/84A AU570667B2 (en) | 1983-02-07 | 1984-01-25 | 2-phenyl-3-oxo-3,4-dihydro-benzothiazine(1,4) derivatives |
| KR1019840000429A KR910005706B1 (ko) | 1983-02-07 | 1984-01-31 | 벤조티아진 유도체의 제조방법 |
| ES529462A ES8601942A1 (es) | 1983-02-07 | 1984-02-03 | Un procedimiento para la preparacion de nuevos derivados de benzotiazina |
| NO840434A NO164169C (no) | 1983-02-07 | 1984-02-06 | Analogifremgangsmaate for fremstilling av terapeutisk aktive benzothiazinderivater. |
| FI840482A FI81344C (fi) | 1983-02-07 | 1984-02-06 | Foerfarande foer framstaellning av nya farmakologiskt verksamma 2-fenyl-3-oxo-1,4-bensotiazinderivat. |
| EP84101235A EP0116368B1 (de) | 1983-02-07 | 1984-02-07 | Benzothiazin-Derivate |
| AT84101235T ATE30421T1 (de) | 1983-02-07 | 1984-02-07 | Benzothiazin-derivate. |
| DE8484101235T DE3466987D1 (de) | 1983-02-07 | 1984-02-07 | Benzothiazine derivatives |
| DK053784A DK160150C (da) | 1983-02-07 | 1984-02-07 | Benzothiazinderivater, fremgangsmaade til fremstilling heraf og farmaceutiske praeparater indeholdende samme |
| ES544140A ES8706654A1 (es) | 1983-02-07 | 1985-06-13 | Un procedimiento para la preparacion de nuevos derivados de benzotiazina |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58020990A JPS59148771A (ja) | 1983-02-09 | 1983-02-09 | ベンゾチアジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59148771A JPS59148771A (ja) | 1984-08-25 |
| JPH0526785B2 true JPH0526785B2 (de) | 1993-04-19 |
Family
ID=12042566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58020990A Granted JPS59148771A (ja) | 1983-02-07 | 1983-02-09 | ベンゾチアジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59148771A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE71622T1 (de) * | 1985-07-29 | 1992-02-15 | Santen Pharmaceutical Co Ltd | Neue benzothiazinabkoemmlinge. |
| DE3614363A1 (de) * | 1986-04-28 | 1987-10-29 | Hoechst Ag | Benzothiazinon-derivate, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und deren verwendung |
| EP0429676B1 (de) * | 1989-06-16 | 1996-09-18 | Santen Pharmaceutical Co., Ltd | Arzneimittel für bessere gehirnwirkung |
-
1983
- 1983-02-09 JP JP58020990A patent/JPS59148771A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59148771A (ja) | 1984-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1483262B1 (de) | Als biomarker geeignete cumarine | |
| EP0839136B1 (de) | BENZO[g]CHINOLINDERIVATE | |
| JPH0559040A (ja) | 新規なベンゾ［５，６ シクロヘプタ［１，２−ｂ ピリジン誘導体及びこれを含有する抗アレルギー剤 | |
| CZ78594A3 (en) | Heteroaryl amines functioning as acetylcholinesterase inhibitors, process of their preparation, pharmaceutical compositions containing thereof and their use | |
| EP0116368B1 (de) | Benzothiazin-Derivate | |
| US5155133A (en) | Antiarrhythmic compounds and pharmaceutical compositions and methods thereof | |
| NO831653L (no) | Fremgangsmaate ved fremstilling av nye terapeutisk virksomme benzothiazolinforbindelser | |
| JPH0526785B2 (de) | ||
| JPH0358341B2 (de) | ||
| JPH0225481A (ja) | ２―［（４―ピペリジニル）メチル］―１，２，３，４―テトラヒドロイソキノリン誘導体、その製造方法およびその治療への適用 | |
| Baggaley et al. | Inhibitors of blood platelet aggregation. Effects of some 1, 2-benzisothiazol-3-ones on platelet responsiveness to adenosine diphosphate and collagen | |
| US6127360A (en) | Diamine derivatives and pharmaceutical containing the same | |
| KR910004432B1 (ko) | 2-아릴벤조티아졸린 유도체의 제조방법 | |
| JPH0568470B2 (de) | ||
| WO1994003425A2 (en) | Carbostyril derivatives for the treatment of arrhythmia | |
| WO1986005490A1 (en) | 2-arylbenzothiazine derivatives | |
| US5736558A (en) | 4-(6-fluoro-1,2-benzisoxazolyl)-1 piperidinyl-propoxy-chromen-4-one-one-derivatives, their preparation and their use in the treatment of psychosis, schizophrenia and anxiety | |
| CA1337201C (en) | 4,5,6,7-tetrahydroisothiazolo [4,5-c] pyridine derivatives | |
| US5310750A (en) | Heterocyclic compounds useful as α2 -adrenoceptor antagonists | |
| JP3038018B2 (ja) | 新規ｎ―アミノアルキル―２―アントラセンカルボキサミド；新規ドーパミン受容体サブタイプ特異的リガンド | |
| DK155938B (da) | Analogifremgangsmaade til fremstilling af benzisoxazolderivater | |
| JPH0156067B2 (de) | ||
| CZ20031861A3 (cs) | Derivát piperazinylkarbonylchinolinu a piperazinylkarbonylisochinolinu, způsob jeho přípravy, jeho použití a farmaceutický prostředek, který ho obsahuje | |
| JPS604173B2 (ja) | カルボスチリル誘導体の製法 | |
| US4866176A (en) | 8-Piperazinyl-1,7-naphthyridine derivative having pharmaceutical activity |