JPS6150975A - ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体 - Google Patents

ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体

Info

Publication number: JPS6150975A
Authority: JP; Japan
Prior art keywords: formula; agent; reaction; compound expressed; action
Prior art date: 1984-08-20
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.): Granted

Application number

JP17392284A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0522706B2 (pl

Inventor

Hiroyoshi Hidaka

弘義日高

Yutaka Kawamatsu

豊川松

Hirosada Sugihara

杉原　弘貞

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1984-08-20

Filing date

1984-08-20

Publication date

1986-03-13

1984-08-20 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1984-08-20 Priority to JP17392284A priority Critical patent/JPS6150975A/ja

1986-03-13 Publication of JPS6150975A publication Critical patent/JPS6150975A/ja

1993-03-30 Publication of JPH0522706B2 publication Critical patent/JPH0522706B2/ja

Status Granted legal-status Critical Current

Links

OPRJGGPLBMHEQK-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)benzenesulfonamide Chemical class S1C(=NC2=C1C=CC=C2)C2=C(C=CC=C2)S(=O)(=O)N OPRJGGPLBMHEQK-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 25
239000003795 chemical substances by application Substances 0.000 abstract description 7
102100035044 Myosin light chain kinase, smooth muscle Human genes 0.000 abstract description 6
108010074596 Myosin-Light-Chain Kinase Proteins 0.000 abstract description 6
239000002904 solvent Substances 0.000 abstract description 6
230000002401 inhibitory effect Effects 0.000 abstract description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 4
230000002040 relaxant effect Effects 0.000 abstract description 4
239000003054 catalyst Substances 0.000 abstract description 3
201000010099 disease Diseases 0.000 abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
150000007530 organic bases Chemical class 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
102000005701 Calcium-Binding Proteins Human genes 0.000 abstract description 2
108010045403 Calcium-Binding Proteins Proteins 0.000 abstract description 2
210000000748 cardiovascular system Anatomy 0.000 abstract description 2
230000000415 inactivating effect Effects 0.000 abstract description 2
210000002460 smooth muscle Anatomy 0.000 abstract description 2
229940124549 vasodilator Drugs 0.000 abstract description 2
239000003071 vasodilator agent Substances 0.000 abstract description 2
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 abstract 1
230000003327 cancerostatic effect Effects 0.000 abstract 1
230000002490 cerebral effect Effects 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
229940069533 paregoric Drugs 0.000 abstract 1
239000008414 paregoric Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 31
-1 benzothian amide Chemical class 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 13
239000000243 solution Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 8
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
102000016349 Myosin Light Chains Human genes 0.000 description 4
108010067385 Myosin Light Chains Proteins 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000003814 drug Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
238000000034 method Methods 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000004913 activation Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
210000004204 blood vessel Anatomy 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000008602 contraction Effects 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
229940125714 antidiarrheal agent Drugs 0.000 description 2
239000003793 antidiarrheal agent Substances 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
238000005259 measurement Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
235000020030 perry Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FQBAMYDJEQUGNV-UHFFFAOYSA-N 2-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC=C1S(O)(=O)=O FQBAMYDJEQUGNV-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
KNLCRNWJXCLJHQ-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propan-1-amine Chemical compound C1CN(CCCN)CCN1C1=CC=CC=C1 KNLCRNWJXCLJHQ-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010004016 Bacterial diarrhoea Diseases 0.000 description 1
208000014644 Brain disease Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
206010008132 Cerebral thrombosis Diseases 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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
101100379081 Emericella variicolor andC gene Proteins 0.000 description 1
206010015719 Exsanguination Diseases 0.000 description 1
PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
201000001429 Intracranial Thrombosis Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
102000003505 Myosin Human genes 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000283977 Oryctolagus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
244000250129 Trigonella foenum graecum Species 0.000 description 1
235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000004004 anti-anginal agent Substances 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000001142 anti-diarrhea Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000002365 anti-tubercular Effects 0.000 description 1
229940124345 antianginal agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000005313 fatty acid group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
238000002350 laparotomy Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
210000003975 mesenteric artery Anatomy 0.000 description 1
210000001363 mesenteric artery superior Anatomy 0.000 description 1
RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
XMRSVLCCIJUKDQ-UHFFFAOYSA-N n-diazobenzenesulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=CC=C1 XMRSVLCCIJUKDQ-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000005325 percolation Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
PCYCVCFVEKMHGA-UHFFFAOYSA-N thiirane 1-oxide Chemical compound O=S1CC1 PCYCVCFVEKMHGA-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP17392284A 1984-08-20 1984-08-20 ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体 Granted JPS6150975A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17392284A JPS6150975A (ja)	1984-08-20	1984-08-20	ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17392284A JPS6150975A (ja)	1984-08-20	1984-08-20	ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体

Publications (2)

Publication Number	Publication Date
JPS6150975A true JPS6150975A (ja)	1986-03-13
JPH0522706B2 JPH0522706B2 (pl)	1993-03-30

Family

ID=15969559

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17392284A Granted JPS6150975A (ja)	1984-08-20	1984-08-20	ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体

Country Status (1)

Country	Link
JP (1)	JPS6150975A (pl)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS63230713A (ja) *	1987-03-19	1988-09-27	Chisso Corp	塩化ビニル重合体の製造方法
EP0330065A1 (en) *	1988-02-18	1989-08-30	Kowa Company, Ltd.	Sulfonamide compounds

1984
- 1984-08-20 JP JP17392284A patent/JPS6150975A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS63230713A (ja) *	1987-03-19	1988-09-27	Chisso Corp	塩化ビニル重合体の製造方法
EP0330065A1 (en) *	1988-02-18	1989-08-30	Kowa Company, Ltd.	Sulfonamide compounds

Also Published As

Publication number	Publication date
JPH0522706B2 (pl)	1993-03-30

Legal Events

Date	Code	Title	Description
2004-08-20	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
ES2648094T3 (es)	2017-12-28	Inhibidores de PI3 cinasa delta y gamma selectivos duales
JP2022119990A (ja)	2022-08-17	アポトーシス誘発剤
TW397831B (en)	2000-07-11	The anti-platelet-agglutination hexahydrogenated pyridine and its derivatives
Razdan et al.	1978	A new class of antimalarial drugs: derivatives of benzothiopyrans
JPH07501330A (ja)	1995-02-09	新規な置換されたサリチル酸
ES2286230T3 (es)	2007-12-01	Compuesto de n-fenilarilsulfonamida, medicamento que contiene el compuesto como principio activo intermedio para el compuesto y procedimiento para producirlos.
CN104557872A (zh)	2015-04-29	稠合杂环化合物、其制备方法、药物组合物和用途
JPH02290841A (ja)	1990-11-30	新規化合物、その製法及びそれを含む医薬組成物
CA3034785A1 (en)	2018-03-01	Pde4 inhibitor
JP3101677B2 (ja)	2000-10-23	ジフェニルピペラジン誘導体及びこれを含有する循環器用薬
US3505354A (en)	1970-04-07	2-methyl-3-p-halobenzoylindole-n-aliphatic acids
PL105486B1 (pl)	1979-10-31	Sposob wytwarzania nowych estrowych pochodnych tiazolinylo i tiazynylobenzimidazolu o dzialaniu przeciwwirusowym
EP3680233A1 (en)	2020-07-15	NOVEL AMIDE COMPOUND, AND Pin1 INHIBITOR, THERAPEUTIC AGENT FOR INFLAMMATORY DISEASES AND THERAPEUTIC AGENT FOR CANCER THAT USE THE SAME
CN104876849B (zh)	2017-05-10	一种吲哚衍生物及其用途
JPS6150975A (ja)	1986-03-13	ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体
Wang et al.	2015	Synthesis and vasorelaxation evaluation of novel biphenyl–furocoumarin derivatives
JPH02218654A (ja)	1990-08-31	安息香酸誘導体、それらの製造方法およびそれらを含有する薬剤
CA1271481A (en)	1990-07-10	Process for the preparation of novel isoxazole derivatives
JPS63145272A (ja)	1988-06-17	４，５−ジヒドロ−６−（４−置換フエニル）−３（２ｈ）−ピリダジノン誘導体
IE913898A1 (en)	1992-05-20	The use of thiazoloisoindolinone derivatives as antiviral¹medicaments
US3770766A (en)	1973-11-06	2-(2-amino-2,2-dialkylamino-3-hydroxy-3-phenyl-1h-benz(f)isoindole-1-ones
CN1636997A (zh)	2005-07-13	取代的三环香豆素类化合物、其制备及抗hiv的应用
HUT62004A (en)	1993-03-29	Process for producing new piperazinoalkyl benzoxazine and thiazine derivatives with heterocyclic substituent, as well as pharmaceutical compositions comprising such compounds
US3784545A (en)	1974-01-08	1-(5-phenyl-4-oxo-2-oxazolin-2-yl)-4-cinnamoylpiperazines
WO1999029683A1 (fr)	1999-06-17	Derives sulfones de sulfures phenoles cycliques, leur procede de preparation, agents de separation et de recuperation contenant des sulfures phenoles cycliques, procedes de separation et de recuperation utilisant ces agents, et compositions de medicaments contenant lesdits sulfures

JPS6150975A - ベンゾチアゾリ−ルベンゼンスルホン酸アミド誘導体 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15969559

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

Also Published As

Similar Documents

Legal Events