CA1267897A - Methode de preparation de derives genre de benzothiazine - Google Patents

Methode de preparation de derives genre de benzothiazine

Info

Publication number: CA1267897A
Authority: CA; Canada
Prior art keywords: methyl; methoxy; compound; formula; salt
Prior art date: 1985-08-06
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

Application number

CA000488136A

Other languages

English (en)

Inventor

Tadashi Iso

Jun-Ichi Iwao

Masayuki Oya

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.)

Santen Pharmaceutical Co Ltd

Original Assignee

Santen Pharmaceutical Co 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.)

1985-08-06

Filing date

1985-08-06

Publication date

1990-04-17

1985-08-06 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1985-08-06 Priority to CA000488136A priority Critical patent/CA1267897A/fr

1990-04-17 Application granted granted Critical

1990-04-17 Publication of CA1267897A publication Critical patent/CA1267897A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 20
UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 48
-1 nitro, hydroxy Chemical group 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 14
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
239000004480 active ingredient Substances 0.000 claims 4
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 3
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims 2
239000001530 fumaric acid Substances 0.000 claims 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
239000004310 lactic acid Substances 0.000 claims 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
239000011976 maleic acid Substances 0.000 claims 2
JXHBQZRXZKSNND-UHFFFAOYSA-N 2-[2-[4-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]butoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one Chemical group S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCCN(C)CCOC1=CC=C(OCO2)C2=C1 JXHBQZRXZKSNND-UHFFFAOYSA-N 0.000 claims 1
WEGYSJAJMPOKRI-UHFFFAOYSA-N 2-[2-[4-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]butoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one;oxalic acid Chemical group OC(=O)C(O)=O.S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCCN(C)CCOC1=CC=C(OCO2)C2=C1 WEGYSJAJMPOKRI-UHFFFAOYSA-N 0.000 claims 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
150000003891 oxalate salts Chemical class 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 7
208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 12
239000000243 solution Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000002213 calciumantagonistic effect Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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 2
238000004566 IR spectroscopy Methods 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
150000001412 amines Chemical class 0.000 description 2
230000002744 anti-aggregatory effect Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
235000011148 calcium chloride Nutrition 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
230000008602 contraction Effects 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000000763 evoking effect Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
PQDZYOUYROPJGN-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-methylethanamine Chemical compound CNCCOC1=CC=C2OCOC2=C1 PQDZYOUYROPJGN-UHFFFAOYSA-N 0.000 description 1
VNWRTGOGEXBNSD-UHFFFAOYSA-N 2-[2-(4-bromobutoxy)-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one Chemical compound COC1=CC=C(OCCCCBr)C(C2C(N(C)C3=CC=CC=C3S2)=O)=C1 VNWRTGOGEXBNSD-UHFFFAOYSA-N 0.000 description 1
QEXGSXDFQURHPC-UHFFFAOYSA-N 2-[2-[3-[(3,4-dimethoxyphenoxy)methyl-methylamino]propoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCN(C)COC1=CC=C(OC)C(OC)=C1 QEXGSXDFQURHPC-UHFFFAOYSA-N 0.000 description 1
WPGNXTVWANEDQT-UHFFFAOYSA-N 2-[2-[4-[2-(3,4-dimethoxyphenoxy)ethyl-methylamino]butoxy]-5-methoxyphenyl]-4h-1,4-benzothiazin-3-one;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2NC(=O)C1C1=CC(OC)=CC=C1OCCCCN(C)CCOC1=CC=C(OC)C(OC)=C1 WPGNXTVWANEDQT-UHFFFAOYSA-N 0.000 description 1
BNSBUILZCYWYAX-UHFFFAOYSA-N 2-[2-[4-[2-(4-chlorophenoxy)ethyl-cyclohexylamino]butoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one;oxalic acid Chemical compound OC(=O)C(O)=O.S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCCN(C1CCCCC1)CCOC1=CC=C(Cl)C=C1 BNSBUILZCYWYAX-UHFFFAOYSA-N 0.000 description 1
IFXHQULCWYGQMV-UHFFFAOYSA-N 2-[4-[4-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]butoxy]phenyl]-4-methyl-1,4-benzothiazin-3-one;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C2OCOC2=CC(OCCN(CCCCOC=2C=CC(=CC=2)C2C(N(C)C3=CC=CC=C3S2)=O)C)=C1 IFXHQULCWYGQMV-UHFFFAOYSA-N 0.000 description 1
DDKGZGJDFNADRV-UHFFFAOYSA-N 2-[4-[4-[2-(2-fluorophenoxy)ethylamino]butoxy]phenyl]-4-methyl-1,4-benzothiazin-3-one;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2N(C)C(=O)C1C(C=C1)=CC=C1OCCCCNCCOC1=CC=CC=C1F DDKGZGJDFNADRV-UHFFFAOYSA-N 0.000 description 1
CMNFULXWBKPZNU-UHFFFAOYSA-N 2-[5-methoxy-2-[4-[methyl(2-phenoxyethyl)amino]butoxy]phenyl]-4-methyl-1,4-benzothiazin-3-one;oxalic acid Chemical compound OC(=O)C(O)=O.S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCCN(C)CCOC1=CC=CC=C1 CMNFULXWBKPZNU-UHFFFAOYSA-N 0.000 description 1
FDXKZXXPAWLHDQ-UHFFFAOYSA-N 4-methyl-2-[4-[3-[2-(3,4,5-trimethoxyphenoxy)ethylamino]propoxy]phenyl]-1,4-benzothiazin-3-one;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(OCCNCCCOC=2C=CC(=CC=2)C2C(N(C)C3=CC=CC=C3S2)=O)=C1 FDXKZXXPAWLHDQ-UHFFFAOYSA-N 0.000 description 1
TZTGSFCECWULGO-UHFFFAOYSA-N 4H-1,4-benzothiazin-3-one oxalic acid Chemical compound C(C(=O)O)(=O)O.O=C1CSC2=C(N1)C=CC=C2 TZTGSFCECWULGO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
JGCYNQQMWBAGQK-UHFFFAOYSA-N OC(=O)C(O)=O.C1=CC=C2N=CCSC2=C1 Chemical compound OC(=O)C(O)=O.C1=CC=C2N=CCSC2=C1 JGCYNQQMWBAGQK-UHFFFAOYSA-N 0.000 description 1
208000027089 Parkinsonian disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical compound C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium 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
229910052801 chlorine Inorganic materials 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 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
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1

Landscapes

Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CA000488136A 1985-08-06 1985-08-06 Methode de preparation de derives genre de benzothiazine Expired CA1267897A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000488136A CA1267897A (fr)	1985-08-06	1985-08-06	Methode de preparation de derives genre de benzothiazine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000488136A CA1267897A (fr)	1985-08-06	1985-08-06	Methode de preparation de derives genre de benzothiazine

Publications (1)

Publication Number	Publication Date
CA1267897A true CA1267897A (fr)	1990-04-17

Family

ID=4131119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000488136A Expired CA1267897A (fr)	1985-08-06	1985-08-06	Methode de preparation de derives genre de benzothiazine

Country Status (1)

Country	Link
CA (1)	CA1267897A (fr)

1985
- 1985-08-06 CA CA000488136A patent/CA1267897A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-04-17	MKLA	Lapsed

Publication	Publication Date	Title
SU1160935A3 (ru)	1985-06-07	Способ получени производных бензазепина или их кислотно-аддитивных солей с неорганическими кислотами
EP0193256B1 (fr)	1989-04-05	Dérivés de thiazolidinediones, leur préparation et utilisation
EP0159566B1 (fr)	1987-12-16	Dérivés de pipérazine, procédé pour leur production et compositions pharmaceutiques les contenant comme substances actives
EP0252503B1 (fr)	1992-11-19	Dérivés d'aminoimidazoquinoléine
US4786635A (en)	1988-11-22	Novel benzothiazine derivatives
KR100296191B1 (ko)	2001-11-05	벤조아진유도체또는그의염및이를함유하는의약조성물
US4841076A (en)	1989-06-20	Benzopyran derivatives
CA1245650A (fr)	1988-11-29	Preparation de derives inedits de benzothiazine
US4066648A (en)	1978-01-03	Isochroman derivatives
EP0249407B1 (fr)	1991-01-30	Agents antiallergiques et anti-inflammatoires
US4593035A (en)	1986-06-03	Carbostyril derivatives
CA1169860A (fr)	1984-06-26	Procede de preparation de nouveaux derives de benzothiazoline
US4684651A (en)	1987-08-04	Alkylenedioxybenzene and acid addition salts thereof useful as hypotensives
US4104388A (en)	1978-08-01	3-Substituted benzisothiazole, 1,1-dioxides
US4771047A (en)	1988-09-13	Benzazepine derivatives
HU199124B (en)	1990-01-29	Process for producing benzazepine sulfonamides and antiarrhythmic agents comprising these compounds
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