WO1983000865A1 - Benzothiazoline compounds - Google Patents
Benzothiazoline compounds Download PDFInfo
- Publication number
- WO1983000865A1 WO1983000865A1 PCT/JP1982/000363 JP8200363W WO8300865A1 WO 1983000865 A1 WO1983000865 A1 WO 1983000865A1 JP 8200363 W JP8200363 W JP 8200363W WO 8300865 A1 WO8300865 A1 WO 8300865A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- hydrogen atom
- acetyl
- alkyl group
- Prior art date
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 230000008569 process Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 18
- -1 phenylcarboxy group Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- KKEBXNMGHUCPEZ-UHFFFAOYSA-N 4-phenyl-1-(2-sulfanylethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCS)CC1C1=CC=CC=C1 KKEBXNMGHUCPEZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 241001279686 Allium moly Species 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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- 229910052739 hydrogen Inorganic materials 0.000 description 10
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- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 7
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- QVVAWONRFLJUBP-UHFFFAOYSA-N 1,3-benzothiazol-3-ium;chloride Chemical compound Cl.C1=CC=C2SC=NC2=C1 QVVAWONRFLJUBP-UHFFFAOYSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
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- 230000002107 myocardial effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000004466 pelleted feed Substances 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to a benzothiazolin derivative represented by the general formula [I] and a salt thereof.
- R 1 represents a lower alkyl group o
- R 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a hydroxy group, a hydrogen atom, a hydrogen atom, a hydrogen atom, a lower alkyl group or a sulfamo; Indicates one or more groups to be selected.
- R 3 is-CC H ⁇ n-N ⁇ 5 NN-R one N 0-N (CH 2 ) D
- R 4 and R 4 are the same or different and each represent a hydrogen atom, a lower alkyl group, a cyclohexyl group or a substituted lower alkyl group, and the substituent is a hydroxy group;
- the ring may be a lower alkyl group, a hydroxyl group, a gen atom, a lower alkyl group, a nitro group, a cyano group, an acetate group, or a lower group.
- the amino group may be further substituted with one or more groups selected from the amino group.
- ⁇ R 6 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 2 to 8 carbon atoms, and 2 to 8 carbon atoms.
- the phenyl ring may be a lower alkyl group, a hydroxy group, a halo. Gen atom, a lower alkoxy group, a nitro group, a silo group, a silo group, or a silo group. It may be further substituted with one or more groups selected from lower alkylamino groups.
- R 7 represents a hydrogen atom, a hydroxy group, a phenyl lower alkyl group or a benzyl group o
- R 8 is a hydroxy group, a lower alkoxy group, -N
- Z represents a linear or branched alkylene having 1 to 6 carbon atoms.
- the 3-position substituent on the benzothiazoline ring is a lower alkanol group
- the 2-position substituent is a phenyl group
- the 2-phenylphenylazothiazoline derivative reported by Cossey et al. And Palmer et al. Is a force substituted by a phenyl ring S ether derivative;
- the substituent at the 3-position is not a lower alcohol group but a hydrogen atom, an alkyl group, a benzyl group, etc., and their pharmacological and antibacterial effects are related to o.
- the present invention relates to a benzothiazolin derivative represented by the general formula [I] 0 ) m — R J [I]
- the substituent at the 3-position of the benzothiazoline ring is a lower alkanol group
- the substituent at the 2-position is a phenyl group.
- the compound of the present invention not only has a novel chemical structure, The known benzothiazolin derivatives were found to be useful for the treatment of unknown cardiovascular disease.o
- Cardiovascular diseases include angina pectoris, arrhythmias, thrombosis, etc., and 3—blockers, platelet aggregation inhibitors, calcium antagonists, etc. have been used as therapeutic agents. o
- the compound of the present invention has excellent antiplatelet aggregation and calcium ⁇ anti-activity. O Therefore, the compound of the present invention is useful for cardiovascular diseases. .
- ⁇ represents a halogen atom, a carboxyl group or a holmyl group, and may be combined with one OH to form an epoxy ring.
- Rmin derivatives are HN HN 0 or
- reaction between the compound represented by the formula and the amide derivative can be divided into the following reactions a) to d) .o
- the above reaction does not require any special conditions, and is generally ordinarily used for the reaction of amine derivatives with halides, carboxylic acid derivatives, hydroxyderivatives or epoxy derivatives.
- ⁇ can use the methods used for
- the compound of the present invention can be converted to an acid salt.
- the above salts can be obtained by a general method using an inorganic acid or an organic acid.
- the compound represented by the formula [I] has one or more asymmetric carbons and thus has stereoisomers, and all of these isomers are included in the present invention.
- the compounds of the present invention are shown in Table I to! [Listed in.
- Example 3 Aminobic acid pill bromide (0.839) was used instead of 3—dimethylaminopircyl pillchloride, and the title compound was used. 9 (Yield 65 ° h) o
- H H 36 65 111-113 3420, 1674, 1458, 1370, 724, 616
- Compound 87a is a diastereomer of compound 87b
- V OL L IH ⁇ JP UB , Hi i J * S »o 8_ n1 ' ⁇ n P * ⁇ a * t S n. ⁇ * ⁇ ⁇ u ⁇
- the calcium antagonist activity of the compound was determined by using a colony of a mormotte.o A musculoskeletal ligature extirpated in 32 was suspended in an organ bath filled with Krebs solution. Then, inject oxygen containing carbon dioxide gas. 5 After reaching equilibrium, wash the muscle with Ca + + -removed Krebs solution. 0 When the muscle relaxes to its original level, Suspend the Ca + + -removed Krebs solution with the addition of the force beam. .
- the compound of the present invention has a calcium antagonistic activity.
- the high platelet concentration increases the number of circulating platelet clumps, leading to arrhythmias, cardiac arrest, and myocardial upset. These cardiovascular diseases can be prevented by inhibiting platelet aggregation.
- O The effect of the test compound on platelet aggregation in vitro was examined and the results were obtained. It was found to have agglutinating activity.
- Anti-aggregation activity was expressed as the concentration of the test compound that caused 50 inhibition of control.o
- test compound was suspended in a 0.5 ° tragant suspension and 0.5 ⁇ / 20 ⁇ body weight was orally administered.o Table m
- This compound can be administered orally or parenterally.
- O Dosage forms include tablets, capsules, granules, powders, suppositories, injections, etc. o Administration The amount is determined according to the symptoms, dosage form, etc., but it is tight, 1 is said to be 1 to 5, 0 00 ⁇ , preferably 10 to 1, 0 0 3 ⁇ 4 ⁇ once or divided into several doses. ⁇ Preparation examples are shown below ⁇ . Preparation examples
- the present invention provides novel compounds useful as pharmaceuticals.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE823248957T DE3248957T1 (de) | 1981-09-12 | 1982-09-10 | Benzothiazolinverbindungen |
| AT0904882A AT379592B (de) | 1981-09-12 | 1982-09-10 | Verfahren zur herstellung von neuen benzothiazolin-verbindungen und von deren salzen |
| NL8220310A NL8220310A (nl) | 1981-09-12 | 1982-09-10 | Benzothiazolineverbindingen. |
| AU89026/82A AU541223B2 (en) | 1981-09-12 | 1982-09-10 | Benzothiazoline compounds |
| GB08311096A GB2115815B (en) | 1981-09-12 | 1982-09-10 | Benzothiazoline compounds |
| FI831431A FI68232C (fi) | 1981-09-12 | 1983-04-27 | Foerfarande foer framstaellning av benzotiazolinfoereningar me farmaceutiskt verkan |
| DK211283A DK164403C (da) | 1981-09-12 | 1983-05-11 | Analogifremgangsmaade til fremstilling af benzothiazolinderivater |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56/144148810912 | 1981-09-12 | ||
| JP56144148A JPS5846079A (ja) | 1981-09-12 | 1981-09-12 | ベンゾチアゾリン環を有するエ−テル類 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1983000865A1 true WO1983000865A1 (en) | 1983-03-17 |
Family
ID=15355326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1982/000363 WO1983000865A1 (en) | 1981-09-12 | 1982-09-10 | Benzothiazoline compounds |
Country Status (18)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547513A (en) * | 1983-12-27 | 1985-10-15 | Santen Pharmaceutical Co., Ltd. | 2-Arylbenzothiazoline derivatives and their use in treating angina cordis |
| US4558125A (en) * | 1981-09-12 | 1985-12-10 | Santen Pharmaceutical Co., Ltd. | Benzothiazoline compounds which contain a carbonyl group useful for treating cardiovascular disease |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56164877A (en) * | 1980-05-23 | 1981-12-18 | Fujitsu Ltd | Manufacture of head for thermal printer |
| DK143684A (da) * | 1983-03-12 | 1984-09-13 | Bayer Ag | Anvendelse af pyrazolonderivater som lipoxygenasehaemmer ved terapi af isaer ischaemi og hjerterytmeforstyrrelser |
| JPS60207396A (ja) * | 1984-03-31 | 1985-10-18 | ロ−ム株式会社 | 配線基板 |
| JPS61110568A (ja) * | 1984-10-31 | 1986-05-28 | アルカテル・エヌ・ブイ | プリンタ装置 |
| US4728651A (en) * | 1985-10-24 | 1988-03-01 | Hoechst-Roussel Pharmaceuticals Inc. | Antihypertensive thieno-isoxazoles and -pyrazoles |
| JPS62221679A (ja) * | 1986-03-19 | 1987-09-29 | Santen Pharmaceut Co Ltd | ベンゾチアゾリン誘導体 |
| US5147881A (en) * | 1990-11-14 | 1992-09-15 | Pfizer Inc | 4-(1,2-benzisoxazolyl)piperidine antipsychotic agents |
| US5541204A (en) * | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| EP1496053B1 (en) * | 2002-03-29 | 2012-06-20 | Santen Pharmaceutical Co., Ltd. | Kappa-opioid receptor agonist comprising a 2-phenylbenzothiazoline derivative |
| CA2907921C (en) * | 2013-03-22 | 2021-09-07 | Ayumi Pharmaceutical Corporation | Inhibition of il-2 production |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574218A (en) * | 1969-08-11 | 1971-04-06 | Egyt Gyogyszervegyeszeti Gyar | 2-aryl- or aralkyl-substituted benzazole derivatives |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996512A (en) * | 1961-08-15 | Therapeutic derivatives of aryl- | ||
| US3117124A (en) * | 1957-03-20 | 1964-01-07 | Olin Mathieson | Benzothiazole, benzothiazine, and benzothiazepine compounds |
| FR1255312A (fr) * | 1957-10-31 | 1961-03-10 | Crookes Lab Ltd | Dérivés des aryl-benzothiazoles et leur mode de préparation |
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| BE754245A (fr) * | 1969-08-01 | 1970-12-31 | Sumitomo Chemical Co | Derives d'acides phenoxy carboxyliques |
| US3720683A (en) * | 1970-09-02 | 1973-03-13 | Squibb & Sons Inc | 2-phenyl-3-acylbenzothiazolines and their oxides |
| JPS5371071A (en) * | 1976-12-08 | 1978-06-24 | Teijin Ltd | Alpha-phenoxyacetic acid derivs. |
| JPS57179175A (en) * | 1981-04-30 | 1982-11-04 | Shinzo Kano | Preparation of 2-benzothiazolinone derivative or salt thereof |
| JPS5846079A (ja) * | 1981-09-12 | 1983-03-17 | Santen Pharmaceut Co Ltd | ベンゾチアゾリン環を有するエ−テル類 |
-
1981
- 1981-09-12 JP JP56144148A patent/JPS5846079A/ja active Pending
-
1982
- 1982-09-07 IT IT23146/82A patent/IT1196423B/it active
- 1982-09-10 US US06/503,160 patent/US4479949A/en not_active Expired - Lifetime
- 1982-09-10 NL NL8220310A patent/NL8220310A/nl not_active Application Discontinuation
- 1982-09-10 ES ES515655A patent/ES8308552A1/es not_active Expired
- 1982-09-10 CH CH2716/83A patent/CH654001A5/de not_active IP Right Cessation
- 1982-09-10 GB GB08311096A patent/GB2115815B/en not_active Expired
- 1982-09-10 CA CA000411159A patent/CA1169860A/en not_active Expired
- 1982-09-10 AU AU89026/82A patent/AU541223B2/en not_active Ceased
- 1982-09-10 BE BE2/59831A patent/BE894358A/fr not_active IP Right Cessation
- 1982-09-10 DE DE823248957T patent/DE3248957T1/de active Granted
- 1982-09-10 WO PCT/JP1982/000363 patent/WO1983000865A1/ja active IP Right Grant
- 1982-09-10 AT AT0904882A patent/AT379592B/de not_active IP Right Cessation
- 1982-09-13 FR FR8215454A patent/FR2512820B1/fr not_active Expired
-
1983
- 1983-04-26 SE SE8302352A patent/SE444681B/sv not_active IP Right Cessation
- 1983-04-27 FI FI831431A patent/FI68232C/fi not_active IP Right Cessation
- 1983-05-10 NO NO831653A patent/NO831653L/no unknown
- 1983-05-11 DK DK211283A patent/DK164403C/da not_active IP Right Cessation
- 1983-05-13 ES ES522386A patent/ES8407033A1/es not_active Expired
-
1984
- 1984-05-21 US US06/612,322 patent/US4552969A/en not_active Expired - Fee Related
- 1984-05-21 US US06/612,323 patent/US4558125A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574218A (en) * | 1969-08-11 | 1971-04-06 | Egyt Gyogyszervegyeszeti Gyar | 2-aryl- or aralkyl-substituted benzazole derivatives |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558125A (en) * | 1981-09-12 | 1985-12-10 | Santen Pharmaceutical Co., Ltd. | Benzothiazoline compounds which contain a carbonyl group useful for treating cardiovascular disease |
| US4547513A (en) * | 1983-12-27 | 1985-10-15 | Santen Pharmaceutical Co., Ltd. | 2-Arylbenzothiazoline derivatives and their use in treating angina cordis |
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