NO792828L - Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotienotiazin-derivater - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotienotiazin-derivater

Info

Publication number: NO792828L
Authority: NO; Norway
Prior art keywords: methyl; hydroxy; thiazine; dioxide; carboxamide
Prior art date: 1978-09-02

Application number

NO792828A

Other languages

English (en)

Norwegian (no)

Inventor

Wolfhard Engel

Guenter Trummlitz

Ernst Seeger

Walter Haarmann

Guenther Engelhardt

Rainer Zimmermann

Original Assignee

Thomae Gmbh Dr K

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.)

1978-09-02

Filing date

1979-08-31

Publication date

1980-03-04

1979-08-31 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1980-03-04 Publication of NO792828L publication Critical patent/NO792828L/no

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
230000001225 therapeutic effect Effects 0.000 title 1
-1 4-methyl-2-pyridyl Chemical group 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 15
239000007858 starting material Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
150000007529 inorganic bases Chemical class 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
230000000269 nucleophilic effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
KCJKWWHQIMUQIQ-UHFFFAOYSA-N 4-hydroxy-2,7-dimethyl-n-(4-methylpyridin-2-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC(C)=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=CC(C)=CC=N1 KCJKWWHQIMUQIQ-UHFFFAOYSA-N 0.000 claims 1
AJQOBIAMRPMSLH-UHFFFAOYSA-N 7-chloro-4-hydroxy-2-methyl-n-(6-methylpyridin-2-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC(Cl)=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC(C)=N1 AJQOBIAMRPMSLH-UHFFFAOYSA-N 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
238000001953 recrystallisation Methods 0.000 description 45
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 40
238000000354 decomposition reaction Methods 0.000 description 37
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
150000003180 prostaglandins Chemical class 0.000 description 8
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
206010061218 Inflammation Diseases 0.000 description 5
238000001816 cooling Methods 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
229940094443 oxytocics prostaglandins Drugs 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
LRGLFIGRZTYOJU-UHFFFAOYSA-N thiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=CSC=1 LRGLFIGRZTYOJU-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000003110 anti-inflammatory effect Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000004289 sodium hydrogen sulphite Substances 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 3
ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 3
GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 3
QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000006519 CCH3 Chemical group 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
229940114079 arachidonic acid Drugs 0.000 description 3
229920001436 collagen Polymers 0.000 description 3
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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 2
ANRXJNHBFGKLIY-UHFFFAOYSA-N 3-chlorosulfonyl-1-benzothiophene-2-carbonyl chloride Chemical compound C1=CC=C2C(S(Cl)(=O)=O)=C(C(=O)Cl)SC2=C1 ANRXJNHBFGKLIY-UHFFFAOYSA-N 0.000 description 2
SMWAOXCEPHEGFV-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine Chemical compound C1CCCC2=C1N=C(N)S2 SMWAOXCEPHEGFV-UHFFFAOYSA-N 0.000 description 2
DWGWNNCHJPKZNC-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC(Cl)=CC=2)=C1 DWGWNNCHJPKZNC-UHFFFAOYSA-N 0.000 description 2
OVMGTNMCYLZGLS-UHFFFAOYSA-N 4-(trifluoromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC(C(F)(F)F)=CS1 OVMGTNMCYLZGLS-UHFFFAOYSA-N 0.000 description 2
CUWZBHVYLVGOAB-UHFFFAOYSA-N 4-tert-butyl-1,3-thiazol-2-amine Chemical compound CC(C)(C)C1=CSC(N)=N1 CUWZBHVYLVGOAB-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
206010042674 Swelling Diseases 0.000 description 2
NMUXXQGJTFIHJO-UHFFFAOYSA-L [O-]C(C(SC1=C2C=CC=C1)=C2S([O-])(=O)=O)=O.[Na+].[Na+] Chemical compound [O-]C(C(SC1=C2C=CC=C1)=C2S([O-])(=O)=O)=O.[Na+].[Na+] NMUXXQGJTFIHJO-UHFFFAOYSA-L 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
229950011175 aminopicoline Drugs 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000001772 blood platelet Anatomy 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
NIDZUMSLERGAON-UHFFFAOYSA-N ethyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CCOC(=O)CNC NIDZUMSLERGAON-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
WXEFWKWOTRHRJM-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxylate Chemical compound S1C2=CC=CC=C2C2=C1C(O)=C(C(=O)OC)N(C)S2(=O)=O WXEFWKWOTRHRJM-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
RUHCXWOXYTZFNB-UHFFFAOYSA-N 1,1-dioxo-2h-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=C(C(=O)N)NS2(=O)=O RUHCXWOXYTZFNB-UHFFFAOYSA-N 0.000 description 1
VZLCVCNTTZKGRF-UHFFFAOYSA-N 1,1-dioxo-2h-thiazine-3-carboxamide Chemical compound NC(=O)C1=CC=CS(=O)(=O)N1 VZLCVCNTTZKGRF-UHFFFAOYSA-N 0.000 description 1
QXBDFCZHAAOUBY-UHFFFAOYSA-N 1,2-dichloroethanol Chemical compound OC(Cl)CCl QXBDFCZHAAOUBY-UHFFFAOYSA-N 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
CPKYIKLQTYCGFA-UHFFFAOYSA-N 2h-[1]benzothiolo[2,3-e]thiazine Chemical class S1C2=CC=CC=C2C2=C1C=CNS2 CPKYIKLQTYCGFA-UHFFFAOYSA-N 0.000 description 1
JCTLRFNZVZCAHR-UHFFFAOYSA-N 3,6-dichloro-1-benzothiophene-2-carbonyl chloride Chemical compound ClC1=CC=C2C(Cl)=C(C(=O)Cl)SC2=C1 JCTLRFNZVZCAHR-UHFFFAOYSA-N 0.000 description 1
ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 1
GWKSSMDJEWPKCM-UHFFFAOYSA-N 3-chloro-1-benzothiophene-2-carbonyl chloride Chemical compound C1=CC=C2C(Cl)=C(C(=O)Cl)SC2=C1 GWKSSMDJEWPKCM-UHFFFAOYSA-N 0.000 description 1
HJTMIYKPPPYDRJ-UHFFFAOYSA-N 3-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2C(Cl)=C(C(=O)O)SC2=C1 HJTMIYKPPPYDRJ-UHFFFAOYSA-N 0.000 description 1
XMXLBDNVSIHRRA-UHFFFAOYSA-N 4,5-dimethyl-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1C XMXLBDNVSIHRRA-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
DBCIYBCYIDCNHT-UHFFFAOYSA-N 4-hydroxy-2,7-dimethyl-N-(6-methylpyridin-2-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound CN1S(C2=C(C(=C1C(=O)NC1=NC(=CC=C1)C)O)SC1=C2C=CC(=C1)C)(=O)=O DBCIYBCYIDCNHT-UHFFFAOYSA-N 0.000 description 1
XKERWLMMQFWAGN-UHFFFAOYSA-N 4-hydroxy-2,7-dimethyl-n-(4-methyl-1,3-thiazol-2-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC(C)=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=NC(C)=CS1 XKERWLMMQFWAGN-UHFFFAOYSA-N 0.000 description 1
SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical group OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 1
CAALISOCDBBHNX-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-(4-methylpyridin-2-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=CC(C)=CC=N1 CAALISOCDBBHNX-UHFFFAOYSA-N 0.000 description 1
BSWSTLIQJQNXGS-UHFFFAOYSA-N 4-hydroxy-2-methyl-n-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 BSWSTLIQJQNXGS-UHFFFAOYSA-N 0.000 description 1
GBKMRHJFXVYZNI-UHFFFAOYSA-N 4-hydroxy-n-(3-hydroxypyridin-2-yl)-2,7-dimethyl-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC(C)=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CC=C1O GBKMRHJFXVYZNI-UHFFFAOYSA-N 0.000 description 1
HUKBELGUWQLEFD-UHFFFAOYSA-N 5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-amine Chemical compound C1CCC2=C1N=C(N)S2 HUKBELGUWQLEFD-UHFFFAOYSA-N 0.000 description 1
IODWHFFPQHUDAG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzothiazol-2-amine Chemical compound C1=C(C)C(C)=CC2=C1SC(N)=N2 IODWHFFPQHUDAG-UHFFFAOYSA-N 0.000 description 1
SWQWTDAWUSBMGA-UHFFFAOYSA-N 5-chloro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Cl)S1 SWQWTDAWUSBMGA-UHFFFAOYSA-N 0.000 description 1
MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
HNOGSSUZDLBROJ-UHFFFAOYSA-N 5-ethyl-1,3-thiazol-2-amine Chemical compound CCC1=CN=C(N)S1 HNOGSSUZDLBROJ-UHFFFAOYSA-N 0.000 description 1
FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 1
HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 1
WURBKTNKFMMSGZ-UHFFFAOYSA-N 5-propyl-1,3-thiazol-2-amine Chemical compound CCCC1=CN=C(N)S1 WURBKTNKFMMSGZ-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical group CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
CHHQFTNLNBGWGS-UHFFFAOYSA-N 6-chloro-3-chlorosulfonyl-1-benzothiophene-2-carbonyl chloride Chemical compound ClC1=CC=C2C(S(Cl)(=O)=O)=C(C(=O)Cl)SC2=C1 CHHQFTNLNBGWGS-UHFFFAOYSA-N 0.000 description 1
BKVVCRYJMGROCO-UHFFFAOYSA-N 7-chloro-4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC(Cl)=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 BKVVCRYJMGROCO-UHFFFAOYSA-N 0.000 description 1
101100129500 Caenorhabditis elegans max-2 gene Proteins 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
206010014513 Embolism arterial Diseases 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
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 1
241001465754 Metazoa Species 0.000 description 1
PGBFYLVIMDQYMS-UHFFFAOYSA-N Methyl thiophene-2-carboxylate Chemical compound COC(=O)C1=CC=CS1 PGBFYLVIMDQYMS-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
YBGJZYCWGNYUMA-UHFFFAOYSA-M [Cl-].[P+]=O Chemical compound [Cl-].[P+]=O YBGJZYCWGNYUMA-UHFFFAOYSA-M 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
244000309464 bull Species 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
HQZMRJBVCVYVQA-UHFFFAOYSA-N hydron;methyl 2-(methylamino)acetate;chloride Chemical compound Cl.CNCC(=O)OC HQZMRJBVCVYVQA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000001365 lymphatic vessel Anatomy 0.000 description 1
125000003099 maleoyl group Chemical group C(\C=C/C(=O)*)(=O)* 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
ZMSSTGLPSBEKBJ-UHFFFAOYSA-N methyl 3-chlorosulfonyl-1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2C(S(Cl)(=O)=O)=C(C(=O)OC)SC2=C1 ZMSSTGLPSBEKBJ-UHFFFAOYSA-N 0.000 description 1
WZTQTJUHNMBLDI-UHFFFAOYSA-N methyl 3-chlorosulfonyl-6-methyl-1-benzothiophene-2-carboxylate Chemical compound CC1=CC=C2C(S(Cl)(=O)=O)=C(C(=O)OC)SC2=C1 WZTQTJUHNMBLDI-UHFFFAOYSA-N 0.000 description 1
GRALSQMNEVJJRH-UHFFFAOYSA-N methyl 6-chloro-3-chlorosulfonyl-1-benzothiophene-2-carboxylate Chemical compound ClC1=CC=C2C(S(Cl)(=O)=O)=C(C(=O)OC)SC2=C1 GRALSQMNEVJJRH-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
210000001589 microsome Anatomy 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
UNAMCDUYZJGINN-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-thiazol-2-yl)-4-hydroxy-2-methyl-1,1-dioxo-[1]benzothiolo[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC3=CC=CC=C3C=2S(=O)(=O)N(C)C=1C(=O)NC1=NC(C)=C(C)S1 UNAMCDUYZJGINN-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
108700027361 sarcosine methyl ester Proteins 0.000 description 1
VXGABWCSZZWXPC-UHFFFAOYSA-N sarcosine methyl ester hydrochloride Natural products CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
UTQSEIGPHWYABW-UHFFFAOYSA-M sodium;2-carboxy-6-chloro-1-benzothiophene-3-sulfonate Chemical compound [Na+].ClC1=CC=C2C(S([O-])(=O)=O)=C(C(=O)O)SC2=C1 UTQSEIGPHWYABW-UHFFFAOYSA-M 0.000 description 1
ANGCTSHWFCORHO-UHFFFAOYSA-M sodium;thiophene-3-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=1C=CSC=1 ANGCTSHWFCORHO-UHFFFAOYSA-M 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
229950005175 sudoxicam Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO792828A 1978-09-02 1979-08-31 Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotienotiazin-derivater NO792828L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782838377 DE2838377A1 (de)	1978-09-02	1978-09-02	Neue 4-hydroxy-2h eckige klammer auf 1 eckige klammer zu benzothieno eckige klammer auf 2,3-e eckige klammer zu -1,2- thiazin-3-carboxamid-1,1-dioxide sowie deren salze, deren verwendung und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
NO792828L true NO792828L (no)	1980-03-04

Family

ID=6048562

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792828A NO792828L (no)	1978-09-02	1979-08-31	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzotienotiazin-derivater

Country Status (14)

Country	Link
US (1)	US4259336A (el)
EP (1)	EP0009142A1 (el)
JP (1)	JPS5535086A (el)
AU (1)	AU5046679A (el)
DE (1)	DE2838377A1 (el)
DK (1)	DK365879A (el)
ES (1)	ES483711A1 (el)
FI (1)	FI792721A (el)
GR (1)	GR69999B (el)
IL (1)	IL58155A0 (el)
NO (1)	NO792828L (el)
PT (1)	PT70134A (el)
YU (1)	YU212279A (el)
ZA (1)	ZA794618B (el)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU5811280A (en) *	1979-06-13	1980-12-18	F. Hoffmann-La Roche Ag	Thiazine derivatives
GR80576B (en) *	1983-10-17	1984-11-29	Fujisawa Pharmaceutical Co	Thiazine derivatives, process for preparation thereof and pharmaceutical composition comprising the same
US4683306A (en) *	1984-07-13	1987-07-28	Yuhan Corporation Co., Ltd.	Process for the preparation of 3,4-dihydro-2-substituted-2H-1,2-thiazine-carboxylic acid 1,1-dioxide derivatives
JP2690742B2 (ja) *	1987-03-30	1997-12-17	第一製薬株式会社	複素環アミン誘導体
MX174093B (es) *	1987-06-10	1994-04-21	Pfizer	1,1-DIOXIDOS DE 3,4-DIHIDRO-2-ALQUIL-3-OXO-N-ARIL-2H[1] BENZOTIENO[3,2-e]-1,2-TIAZINO-4-CARBOXIAMIDA
EP1384723A1 (de) *	2002-07-26	2004-01-28	Boehringer Ingelheim Pharma GmbH & Co.KG	Neue 4-Hydroxy-2H-thieno[2,3-e]-1,2-thiazin-3-carboxamid-1,1-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL47877A (en) *	1974-08-26	1978-10-31	Sparamedica Ag	Thienothiazine carboxamide derivatives,their manufacture and pharmaceutical compositions containing them
DE2539112C2 (de) *	1975-09-03	1983-12-15	Dr. Karl Thomae Gmbh, 7950 Biberach	4-Hydroxy-2H-naphtho[2,1-e]-1,2-thiazin-3-carboxamid-1,1-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2452946A1 (de) *	1974-11-08	1976-05-13	Merck Patent Gmbh	Pyrazolidinone und verfahren zu ihrer herstellung
SU623520A3 (ru) *	1976-09-07	1978-09-05	Ф.Гоффанн-Ля Рош И Ко Аг, (Фирма)	Способ получени производных тиенотиазина
DE2704485A1 (de) *	1977-02-03	1978-08-10	Thomae Gmbh Dr K	Neue 2,5-dihydro-1,2-thiazino eckige klammer auf 5,6-b eckige klammer zu indol-3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
AU518216B2 (en) *	1977-09-06	1981-09-17	Hafslund Nycomed Pharma Aktiengesellschaft	Thienothiazine derivatives

1978
- 1978-09-02 DE DE19782838377 patent/DE2838377A1/de not_active Withdrawn
1979
- 1979-08-16 GR GR59843A patent/GR69999B/el unknown
- 1979-08-27 EP EP79103150A patent/EP0009142A1/de not_active Withdrawn
- 1979-08-29 ES ES483711A patent/ES483711A1/es not_active Expired
- 1979-08-30 YU YU02122/79A patent/YU212279A/xx unknown
- 1979-08-31 ZA ZA00794618A patent/ZA794618B/xx unknown
- 1979-08-31 DK DK365879A patent/DK365879A/da not_active Application Discontinuation
- 1979-08-31 FI FI792721A patent/FI792721A/fi not_active Application Discontinuation
- 1979-08-31 IL IL58155A patent/IL58155A0/xx unknown
- 1979-08-31 AU AU50466/79A patent/AU5046679A/en not_active Abandoned
- 1979-08-31 NO NO792828A patent/NO792828L/no unknown
- 1979-08-31 PT PT70134A patent/PT70134A/pt unknown
- 1979-08-31 JP JP11053079A patent/JPS5535086A/ja active Pending
- 1979-10-22 US US06/086,743 patent/US4259336A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK365879A (da)	1980-03-03
ZA794618B (en)	1981-05-27
PT70134A (de)	1979-09-01
AU5046679A (en)	1980-03-13
ES483711A1 (es)	1980-04-16
IL58155A0 (en)	1979-12-30
JPS5535086A (en)	1980-03-11
DE2838377A1 (de)	1980-03-20
FI792721A (fi)	1980-03-03
US4259336A (en)	1981-03-31
YU212279A (en)	1983-01-21
EP0009142A1 (de)	1980-04-02
GR69999B (el)	1982-07-23

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