SK9092003A3 - 1,1-Dioxo-2H-1,2-benzothiazine-3-carboxamide derivatives, method for preparing same and pharmaceutical compositions comprising same - Google Patents

1,1-Dioxo-2H-1,2-benzothiazine-3-carboxamide derivatives, method for preparing same and pharmaceutical compositions comprising same Download PDF

Info

Publication number: SK9092003A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; branched; linear; group
Prior art date: 2000-12-21

Application number

SK909-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Jean-Claude Madelmont

Isabelle Giraud

Aurelien Vidal

Emmanuelle Mounetou

Maryse Rapp

Jean-Claude Maurizis

Pierre Renard

Daniel-Henri Caignard

Jean-Guy Bizot-Espiard

Original Assignee

Servier Lab

Inst Nat Rech Medicale

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.)

2000-12-21

Filing date

2001-12-21

Publication date

2004-01-08

2001-12-21 Application filed by Servier Lab, Inst Nat Rech Medicale filed Critical Servier Lab

2004-01-08 Publication of SK9092003A3 publication Critical patent/SK9092003A3/sk

Links

238000000034 method Methods 0.000 title claims description 30
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
YSMNECAIZNOYOW-UHFFFAOYSA-N 1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide Chemical class C1=CC=C2S(=O)(=O)NC(C(=O)N)=CC2=C1 YSMNECAIZNOYOW-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 100
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
230000003287 optical effect Effects 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
206010003246 arthritis Diseases 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
201000008482 osteoarthritis Diseases 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000005936 piperidyl group Chemical group 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
DWAOORYLBGXNSE-UHFFFAOYSA-N diethyl-[3-[(4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl]-methylazanium;iodide Chemical compound [I-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(CC)CC)=C(O)C2=C1 DWAOORYLBGXNSE-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
125000002947 alkylene group Chemical group 0.000 abstract 1
125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
239000000047 product Substances 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
210000000845 cartilage Anatomy 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
-1 (3 - [(4-Hydroxy-2-methyl-1,1-dioxo-2 H -1,2-benzothiazin-3-yl) carbonylamino] propyl} -methylammonium iodide Chemical compound 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
102000016284 Aggrecans Human genes 0.000 description 5
108010067219 Aggrecans Proteins 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
230000001575 pathological effect Effects 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
239000012346 acetyl chloride Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
108010002352 Interleukin-1 Proteins 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000000636 Northern blotting Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
210000001612 chondrocyte Anatomy 0.000 description 2
238000001816 cooling Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 description 2
NGHIOTWSWSQQNT-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC)=C(O)C2=C1 NGHIOTWSWSQQNT-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
230000010415 tropism Effects 0.000 description 2
125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
UHZBDNOAMUWOOZ-UHFFFAOYSA-N 3-[(4-acetyloxy-2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl-trimethylazanium;iodide Chemical compound [I-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(C)C)C(OC(C)=O)C2=C1 UHZBDNOAMUWOOZ-UHFFFAOYSA-N 0.000 description 1
JANYAZXKJPPWNU-UHFFFAOYSA-N 3-[(4-hydroxy-2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl-trimethylazanium;iodide Chemical compound [I-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(C)C)C(O)C2=C1 JANYAZXKJPPWNU-UHFFFAOYSA-N 0.000 description 1
JKLRUHPTQZXLOU-UHFFFAOYSA-N 3-[(4-methoxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl-trimethylazanium;iodide Chemical compound [I-].C1=CC=C2C(OC)=C(C(=O)NCCC[N+](C)(C)C)N(C)S(=O)(=O)C2=C1 JKLRUHPTQZXLOU-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
HCLFLZTVKYHLCF-UHFFFAOYSA-N 4-(dimethylamino)butanenitrile Chemical compound CN(C)CCCC#N HCLFLZTVKYHLCF-UHFFFAOYSA-N 0.000 description 1
CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
XGGFJKMKFOCKLE-UHFFFAOYSA-N 4-hydroxy-n-(3-iodopropyl)-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCCI)=C(O)C2=C1 XGGFJKMKFOCKLE-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 1
206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
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WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000000246 agarose gel electrophoresis Methods 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002299 complementary DNA Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
GTPOKQUBILVPDH-UHFFFAOYSA-N diethyl-[3-[(4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl]-methylazanium;chloride Chemical compound [Cl-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(CC)CC)=C(O)C2=C1 GTPOKQUBILVPDH-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical group C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 description 1
NTTJLMGOHHORKM-UHFFFAOYSA-N methyl 2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC)CC2=C1 NTTJLMGOHHORKM-UHFFFAOYSA-N 0.000 description 1
WCNOOAQXLIXCOF-UHFFFAOYSA-N methyl 4-acetyloxy-2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC)C(OC(C)=O)C2=C1 WCNOOAQXLIXCOF-UHFFFAOYSA-N 0.000 description 1
XIWCNJQBMDCBPC-UHFFFAOYSA-N methyl 4-methoxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)OC)=C(OC)C2=C1 XIWCNJQBMDCBPC-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
XEWVCDMEDQYCHX-UHFFFAOYSA-N n,n-diethylethanamine;hydron;iodide Chemical compound [I-].CC[NH+](CC)CC XEWVCDMEDQYCHX-UHFFFAOYSA-N 0.000 description 1
FSUMGRQFCMFLKP-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-hydroxy-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCCN(C)C)=C(O)C2=C1 FSUMGRQFCMFLKP-UHFFFAOYSA-N 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000012306 spectroscopic technique Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
KHJSIIYCVMIBSL-UHFFFAOYSA-N trimethyl-[3-[(2-methyl-1,1-dioxo-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl]azanium;iodide Chemical compound [I-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(C)C)=CC2=C1 KHJSIIYCVMIBSL-UHFFFAOYSA-N 0.000 description 1
FROCHETVOXUOPU-UHFFFAOYSA-N trimethyl-[3-[(2-methyl-1,1-dioxo-3,4-dihydro-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl]azanium;iodide Chemical compound [I-].C1=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(C)C)CC2=C1 FROCHETVOXUOPU-UHFFFAOYSA-N 0.000 description 1
SGRRGNGKLPLRQZ-UHFFFAOYSA-N trimethyl-[3-[(2-methyl-1,1-dioxo-4-phenylmethoxy-1$l^{6},2-benzothiazine-3-carbonyl)amino]propyl]azanium;iodide Chemical compound [I-].C12=CC=CC=C2S(=O)(=O)N(C)C(C(=O)NCCC[N+](C)(C)C)=C1OCC1=CC=CC=C1 SGRRGNGKLPLRQZ-UHFFFAOYSA-N 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)

SK909-2003A 2000-12-21 2001-12-21 1,1-Dioxo-2H-1,2-benzothiazine-3-carboxamide derivatives, method for preparing same and pharmaceutical compositions comprising same SK9092003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0016739A FR2818641B1 (fr)	2000-12-21	2000-12-21	Nouveaux derives de 1,1-dioxo-2h-1,2-benzothiazine 3-carboxamides, leur procede de preparation et les compositions pharmaceutiques que les contiennent
PCT/FR2001/004135 WO2002050049A1 (fr)	2000-12-21	2001-12-21	Derives de 1, 1-dioxo-2h-1, 2-benzothiazine-3-carboxamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
SK9092003A3 true SK9092003A3 (en)	2004-01-08

Family

ID=8857980

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK909-2003A SK9092003A3 (en)	2000-12-21	2001-12-21	1,1-Dioxo-2H-1,2-benzothiazine-3-carboxamide derivatives, method for preparing same and pharmaceutical compositions comprising same

Country Status (18)

Country	Link
US (1)	US20040063696A1 (cs)
EP (1)	EP1343774A1 (cs)
JP (1)	JP2004519442A (cs)
KR (1)	KR20030086247A (cs)
CN (1)	CN1481372A (cs)
AR (1)	AR032380A1 (cs)
AU (1)	AU2002228120A1 (cs)
BR (1)	BR0116424A (cs)
CA (1)	CA2432807A1 (cs)
CZ (1)	CZ20031972A3 (cs)
EA (1)	EA200300672A1 (cs)
FR (1)	FR2818641B1 (cs)
HU (1)	HUP0600065A2 (cs)
MX (1)	MXPA03005556A (cs)
NO (1)	NO20032497L (cs)
PL (1)	PL361664A1 (cs)
SK (1)	SK9092003A3 (cs)
WO (1)	WO2002050049A1 (cs)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4434164A (en) *	1981-06-01	1984-02-28	Pfizer Inc.	Crystalline benzothiazine dioxide salts
IT1206525B (it) *	1982-12-10	1989-04-27	Zionale S R L A Roma	Preparato anti-infiammatorio nonsteroideo, per il trattamento delle affezioni artroreumatiche e metodo per la sua preparazione
DE3431588A1 (de) *	1983-09-12	1985-04-04	Pfizer, Inc., New York, N.Y.	Kristalline benzothiazindioxid-salze und diese enthaltende pharmazeutische zusammensetzungen
US4623486A (en) *	1985-05-29	1986-11-18	Pfizer Inc.	[4-substituted benzoyloxy]-N-substituted-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides having anti-arthritic activity
JP2002514192A (ja) *	1996-11-13	2002-05-14	セフアロン・インコーポレーテツド	ベンゾチアゾおよび関連の複素環基を含有するシステインおよびセリンプロテアーゼ阻害剤
FR2795412B1 (fr) *	1999-06-23	2001-07-13	Adir	Nouveaux derives d'ammonium quaternaire, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

2000
- 2000-12-21 FR FR0016739A patent/FR2818641B1/fr not_active Expired - Fee Related
2001
- 2001-12-20 AR ARP010105927A patent/AR032380A1/es not_active Application Discontinuation
- 2001-12-21 CZ CZ20031972A patent/CZ20031972A3/cs unknown
- 2001-12-21 SK SK909-2003A patent/SK9092003A3/sk unknown
- 2001-12-21 EA EA200300672A patent/EA200300672A1/ru unknown
- 2001-12-21 AU AU2002228120A patent/AU2002228120A1/en not_active Abandoned
- 2001-12-21 PL PL01361664A patent/PL361664A1/xx unknown
- 2001-12-21 BR BRPI0116424-4A patent/BR0116424A/pt not_active IP Right Cessation
- 2001-12-21 JP JP2002551546A patent/JP2004519442A/ja active Pending
- 2001-12-21 EP EP01989655A patent/EP1343774A1/fr not_active Withdrawn
- 2001-12-21 MX MXPA03005556A patent/MXPA03005556A/es unknown
- 2001-12-21 CA CA002432807A patent/CA2432807A1/fr not_active Abandoned
- 2001-12-21 CN CNA018210090A patent/CN1481372A/zh active Pending
- 2001-12-21 KR KR10-2003-7008473A patent/KR20030086247A/ko not_active Ceased
- 2001-12-21 HU HU0600065A patent/HUP0600065A2/hu unknown
- 2001-12-21 US US10/451,489 patent/US20040063696A1/en not_active Abandoned
- 2001-12-21 WO PCT/FR2001/004135 patent/WO2002050049A1/fr not_active Ceased
2003
- 2003-06-03 NO NO20032497A patent/NO20032497L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
BR0116424A (pt)	2006-02-21
CN1481372A (zh)	2004-03-10
WO2002050049A1 (fr)	2002-06-27
EP1343774A1 (fr)	2003-09-17
EA200300672A1 (ru)	2003-12-25
PL361664A1 (en)	2004-10-04
AU2002228120A1 (en)	2002-07-01
JP2004519442A (ja)	2004-07-02
NO20032497D0 (no)	2003-06-03
HUP0600065A2 (en)	2006-04-28
US20040063696A1 (en)	2004-04-01
FR2818641A1 (fr)	2002-06-28
CZ20031972A3 (cs)	2003-11-12
AR032380A1 (es)	2003-11-05
NO20032497L (no)	2003-06-03
FR2818641B1 (fr)	2004-03-05
CA2432807A1 (fr)	2002-06-27
KR20030086247A (ko)	2003-11-07
MXPA03005556A (es)	2004-05-31

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