CS258483B2 - Method of new thienopyridones production - Google Patents
Method of new thienopyridones production Download PDFInfo
- Publication number
- CS258483B2 CS258483B2 CS864362A CS436286A CS258483B2 CS 258483 B2 CS258483 B2 CS 258483B2 CS 864362 A CS864362 A CS 864362A CS 436286 A CS436286 A CS 436286A CS 258483 B2 CS258483 B2 CS 258483B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- new
- mixture
- formula
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- PVQJJFKLQGNQMX-UHFFFAOYSA-N 4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound O=C1C(SC)=CN(C)C2=C1SC=C2 PVQJJFKLQGNQMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 206010019280 Heart failures Diseases 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 208000031225 myocardial ischemia Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YCBIOFDKORLEPZ-UHFFFAOYSA-N thieno[2,3-b]pyridine 1-oxide Chemical class C1=CN=C2S(=O)C=CC2=C1 YCBIOFDKORLEPZ-UHFFFAOYSA-N 0.000 abstract 1
- PLFPURRZLGMMCI-UHFFFAOYSA-N thieno[3,2-b]pyridine 1-oxide Chemical class C1=CC=C2S(=O)C=CC2=N1 PLFPURRZLGMMCI-UHFFFAOYSA-N 0.000 abstract 1
- GWNZXHGUNFBXNX-UHFFFAOYSA-N thieno[3,4-b]pyridine 6-oxide Chemical class C1=CC=NC2=CS(=O)C=C21 GWNZXHGUNFBXNX-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 15
- -1 methoxy, ethoxy Chemical group 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000012265 solid product Substances 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 11
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- 229940125670 thienopyridine Drugs 0.000 description 10
- 239000002175 thienopyridine Substances 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
- DLEBOPPNWGZOHU-UHFFFAOYSA-N 4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=CS2 DLEBOPPNWGZOHU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000124008 Mammalia Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- BQGLRKFKFQRAHF-UHFFFAOYSA-N (5-diazonio-3-iminothiophen-2-ylidene)-methoxymethanolate Chemical compound COC(=O)C=1SC([N+]#N)=CC=1[NH-] BQGLRKFKFQRAHF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FBNNKCQKPBXLEO-UHFFFAOYSA-N 2,4-dimethyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound O=C1C(SC)=CN(C)C2=C1SC(C)=C2 FBNNKCQKPBXLEO-UHFFFAOYSA-N 0.000 description 2
- DJHJROCXVBRMFI-UHFFFAOYSA-N 2-methoxy-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(SC)C(=O)C2=C1C=C(OC)S2 DJHJROCXVBRMFI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QMYWZMDZCWCYNH-UHFFFAOYSA-N 3-ethoxy-4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C(OCC)=CS2 QMYWZMDZCWCYNH-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- LBSXHVXQBYKMOQ-UHFFFAOYSA-N 4-methyl-6-methylsulfanyl-2-phenylthieno[3,2-b]pyridin-7-one Chemical compound S1C=2C(=O)C(SC)=CN(C)C=2C=C1C1=CC=CC=C1 LBSXHVXQBYKMOQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- KYIZHMXFNFGGHA-UHFFFAOYSA-N cis-beta-Chlor-alpha-phenyl-acrylnitril Natural products ClC=C(C#N)C1=CC=CC=C1 KYIZHMXFNFGGHA-UHFFFAOYSA-N 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000004967 organic peroxy acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 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
- 238000001665 trituration Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 description 1
- UUWJBXKHMMQDED-UHFFFAOYSA-N 1-(3-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Cl)=C1 UUWJBXKHMMQDED-UHFFFAOYSA-N 0.000 description 1
- HULNYUGHDJWNNB-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound C=1C=2N(C)C=C(S(C)=O)C(=O)C=2SC=1C1=CC=CC=C1Cl HULNYUGHDJWNNB-UHFFFAOYSA-N 0.000 description 1
- ZTTLHGMPZSHCER-UHFFFAOYSA-N 2-(2-chlorophenyl)-6-methylsulfanyl-4h-thieno[3,2-b]pyridin-7-one Chemical compound S1C2=C(O)C(SC)=CN=C2C=C1C1=CC=CC=C1Cl ZTTLHGMPZSHCER-UHFFFAOYSA-N 0.000 description 1
- IPYAHBYWZQYODO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound C1=CC(OC)=CC=C1C(S1)=CC2=C1C(=O)C(SC)=CN2C IPYAHBYWZQYODO-UHFFFAOYSA-N 0.000 description 1
- OXCIJNHLWIYNOC-UHFFFAOYSA-N 2-bromo-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound O=C1C(SC)=CN(C)C2=C1SC(Br)=C2 OXCIJNHLWIYNOC-UHFFFAOYSA-N 0.000 description 1
- UZKAEYDSJZCSMJ-UHFFFAOYSA-N 2-bromo-6-methylsulfanyl-4h-thieno[3,2-b]pyridin-7-one Chemical compound CSC1=CN=C2C=C(Br)SC2=C1O UZKAEYDSJZCSMJ-UHFFFAOYSA-N 0.000 description 1
- RGAZVVMIUZMDOR-UHFFFAOYSA-N 2-chloro-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound O=C1C(SC)=CN(C)C2=C1SC(Cl)=C2 RGAZVVMIUZMDOR-UHFFFAOYSA-N 0.000 description 1
- RVECXXBMQRHRAJ-UHFFFAOYSA-N 2-chloro-4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(Cl)S2 RVECXXBMQRHRAJ-UHFFFAOYSA-N 0.000 description 1
- CHLXOGPCCBVMEY-UHFFFAOYSA-N 2-methoxy-4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(S(C)=O)C(=O)C2=C1C=C(OC)S2 CHLXOGPCCBVMEY-UHFFFAOYSA-N 0.000 description 1
- HMUZFKILWRVBPL-UHFFFAOYSA-N 3-(carboxymethylsulfanyl)-2-methylbutanoic acid Chemical compound OC(=O)C(C)C(C)SCC(O)=O HMUZFKILWRVBPL-UHFFFAOYSA-N 0.000 description 1
- IHALDHSFCOAJHI-UHFFFAOYSA-N 3-[(3-methoxy-2-methylsulfanyl-3-oxoprop-1-enyl)amino]-5-(4-methoxyphenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(NC=C(SC)C(=O)OC)C=C1C1=CC=C(OC)C=C1 IHALDHSFCOAJHI-UHFFFAOYSA-N 0.000 description 1
- DSOBSDOBPZNWNW-UHFFFAOYSA-N 3-[(3-methoxy-2-methylsulfanyl-3-oxoprop-1-enyl)amino]thiophene-2-carboxylic acid Chemical compound COC(=O)C(SC)=CNC=1C=CSC=1C(O)=O DSOBSDOBPZNWNW-UHFFFAOYSA-N 0.000 description 1
- YFKKIWHCHKKOBW-UHFFFAOYSA-N 3-ethoxy-6-methylsulfanyl-4h-thieno[3,2-b]pyridin-7-one Chemical compound CSC1=CN=C2C(OCC)=CSC2=C1O YFKKIWHCHKKOBW-UHFFFAOYSA-N 0.000 description 1
- WPJHULHDQNMKSR-UHFFFAOYSA-N 4,5-dimethylthiolan-3-one Chemical compound CC1SCC(=O)C1C WPJHULHDQNMKSR-UHFFFAOYSA-N 0.000 description 1
- MCHPKMUAAZTMBK-UHFFFAOYSA-N 4,5-dimethylthiophen-3-amine;hydrochloride Chemical compound Cl.CC=1SC=C(N)C=1C MCHPKMUAAZTMBK-UHFFFAOYSA-N 0.000 description 1
- WQDDXMREYKBGLB-UHFFFAOYSA-N 4-butyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound CCCCN1C=C(SC)C(=O)C2=C1C=CS2 WQDDXMREYKBGLB-UHFFFAOYSA-N 0.000 description 1
- SJHJXFSWXZEHLD-UHFFFAOYSA-N 4-butyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one Chemical compound CCCCN1C=C(S(C)=O)C(=O)C2=C1C=CS2 SJHJXFSWXZEHLD-UHFFFAOYSA-N 0.000 description 1
- XIXBIUHLNVEDNB-UHFFFAOYSA-N 4-ethoxythiophen-3-amine Chemical compound CCOC1=CSC=C1N XIXBIUHLNVEDNB-UHFFFAOYSA-N 0.000 description 1
- SHTOXVMZRVPLBW-UHFFFAOYSA-N 4-methyl-6-methylsulfinyl-2-phenylthieno[3,2-b]pyridin-7-one Chemical compound C=1C=2N(C)C=C(S(C)=O)C(=O)C=2SC=1C1=CC=CC=C1 SHTOXVMZRVPLBW-UHFFFAOYSA-N 0.000 description 1
- HLUDGASXIWUWCK-UHFFFAOYSA-N 4-methyl-6-methylsulfinylthieno[3,2-b]pyridin-7-one;hydrochloride Chemical compound Cl.CN1C=C(S(C)=O)C(=O)C2=C1C=CS2 HLUDGASXIWUWCK-UHFFFAOYSA-N 0.000 description 1
- LXZSEJASWJASBC-UHFFFAOYSA-N 4-methyl-6-methylsulfonylthieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(S(C)(=O)=O)C(=O)C2=C1C=CS2 LXZSEJASWJASBC-UHFFFAOYSA-N 0.000 description 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- GQNDKVSFMBAOLF-UHFFFAOYSA-N 5-phenylthiophen-3-amine Chemical compound NC1=CSC(C=2C=CC=CC=2)=C1 GQNDKVSFMBAOLF-UHFFFAOYSA-N 0.000 description 1
- IHONIJYVYXTAMS-UHFFFAOYSA-N 6-methylsulfanyl-2-phenyl-4h-thieno[3,2-b]pyridin-7-one Chemical compound S1C2=C(O)C(SC)=CN=C2C=C1C1=CC=CC=C1 IHONIJYVYXTAMS-UHFFFAOYSA-N 0.000 description 1
- GLNQOCYQFVHIAC-UHFFFAOYSA-N 6-methylsulfanyl-4h-thieno[3,2-b]pyridin-7-one Chemical compound CSC1=CN=C2C=CSC2=C1O GLNQOCYQFVHIAC-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 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
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- HZYCAKGEXXKCDM-UHFFFAOYSA-N Methyl 2-(methylthio)acetate Chemical compound COC(=O)CSC HZYCAKGEXXKCDM-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-LZFNBGRKSA-N Potassium-45 Chemical compound [45K] ZLMJMSJWJFRBEC-LZFNBGRKSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000011141 high resolution liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- IBJBGSOSQBNYHD-UHFFFAOYSA-N methyl 3-acetamido-5-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(N)=CC=1NC(C)=O IBJBGSOSQBNYHD-UHFFFAOYSA-N 0.000 description 1
- DJPJTIGJPWASOS-UHFFFAOYSA-N methyl 3-acetamido-5-nitrothiophene-2-carboxylate Chemical compound COC(=O)C=1SC([N+]([O-])=O)=CC=1NC(C)=O DJPJTIGJPWASOS-UHFFFAOYSA-N 0.000 description 1
- UKWKMKNACSKDCN-UHFFFAOYSA-N methyl 3-amino-4-phenylthiophene-2-carboxylate Chemical compound NC1=C(C(=O)OC)SC=C1C1=CC=CC=C1 UKWKMKNACSKDCN-UHFFFAOYSA-N 0.000 description 1
- YIQJFQMRWXPBSJ-UHFFFAOYSA-N methyl 3-amino-5-(2-chlorophenyl)thiophene-2-carboxylate Chemical compound NC1=C(C(=O)OC)SC(C=2C(=CC=CC=2)Cl)=C1 YIQJFQMRWXPBSJ-UHFFFAOYSA-N 0.000 description 1
- WLPWFUWQZRXIFA-UHFFFAOYSA-N methyl 3-amino-5-(3-chlorophenyl)thiophene-2-carboxylate Chemical compound NC1=C(C(=O)OC)SC(C=2C=C(Cl)C=CC=2)=C1 WLPWFUWQZRXIFA-UHFFFAOYSA-N 0.000 description 1
- RZYLOBBUEWSONL-UHFFFAOYSA-N methyl 3-amino-5-bromothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Br)=CC=1N RZYLOBBUEWSONL-UHFFFAOYSA-N 0.000 description 1
- QOVUXEZDKNHSJE-UHFFFAOYSA-N methyl 3-amino-5-chlorothiophene-2-carboxylate Chemical compound COC(=O)C=1SC(Cl)=CC=1N QOVUXEZDKNHSJE-UHFFFAOYSA-N 0.000 description 1
- FVKMOPIFLCMZMI-UHFFFAOYSA-N methyl 3-amino-5-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=CC=1N FVKMOPIFLCMZMI-UHFFFAOYSA-N 0.000 description 1
- TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- WPEFWEIHTOLOLC-UHFFFAOYSA-M sodium;3-amino-5-methylthiophene-2-carboxylate Chemical compound [Na+].CC1=CC(N)=C(C([O-])=O)S1 WPEFWEIHTOLOLC-UHFFFAOYSA-M 0.000 description 1
- WVMADKBGYOAZKM-UHFFFAOYSA-M sodium;3-aminothiophene-2-carboxylate Chemical compound [Na+].NC=1C=CSC=1C([O-])=O WVMADKBGYOAZKM-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS874060A CS258500B2 (cs) | 1985-06-15 | 1987-06-03 | Způsob výroby 4-methyl-e-methyleulfinyl-thieno[3,2-b]pyrid-7(4K)-onu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858515207A GB8515207D0 (en) | 1985-06-15 | 1985-06-15 | Therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS436286A2 CS436286A2 (en) | 1987-12-17 |
| CS258483B2 true CS258483B2 (en) | 1988-08-16 |
Family
ID=10580803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS864362A CS258483B2 (en) | 1985-06-15 | 1986-06-12 | Method of new thienopyridones production |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4710506A (de) |
| EP (1) | EP0209977A3 (de) |
| JP (1) | JPS6236382A (de) |
| KR (1) | KR870000339A (de) |
| AU (1) | AU581595B2 (de) |
| CS (1) | CS258483B2 (de) |
| DD (1) | DD253823A5 (de) |
| DK (1) | DK272486A (de) |
| ES (1) | ES8707243A1 (de) |
| FI (1) | FI862520A7 (de) |
| GB (1) | GB8515207D0 (de) |
| GR (1) | GR861527B (de) |
| HU (1) | HU195661B (de) |
| JO (1) | JO1482B1 (de) |
| NO (1) | NO862373L (de) |
| PH (1) | PH22293A (de) |
| PL (1) | PL266392A1 (de) |
| PT (1) | PT82759B (de) |
| YU (2) | YU99386A (de) |
| ZA (1) | ZA864396B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8627698D0 (en) * | 1986-11-20 | 1986-12-17 | Boots Co Plc | Therapeutic agents |
| US4767766A (en) * | 1987-01-30 | 1988-08-30 | Merck & Co., Inc. | Derivatives of 3-hydroxyazabenzo(B)thiophene useful as 5-lipoxygenase inhibitors |
| US4904672A (en) * | 1987-01-30 | 1990-02-27 | Merck & Co., Inc. | Derivatives of 3-hydroxyazabenzo[b]thiophene useful as 5-lipoxygenase inhibitors |
| NZ230711A (en) * | 1988-09-23 | 1990-10-26 | Ortho Pharma Corp | Substituted thienopyrans as antihypertensive agents |
| RU2150470C1 (ru) * | 1994-04-19 | 2000-06-10 | Такеда Кемикал Индастриз Лтд. | Бициклические производные тиофена, способ их получения и композиция на их основе |
| AU5509099A (en) * | 1998-08-03 | 2000-02-28 | Basf Corporation | Pyridinones for the treatment of sexual dysfunction |
| US6451813B1 (en) | 2001-01-26 | 2002-09-17 | R. T. Alamo Ventures I, Llc | Treatment of gastroparesis in certain patient groups |
| US6562838B2 (en) * | 2001-01-26 | 2003-05-13 | R. T. Alamo Ventures I, L.L.C. | Treatment of cardiovascular disease with quinolinone enantiomers |
| US6458804B1 (en) * | 2001-01-26 | 2002-10-01 | R.T. Alamo Venturesi, Llc | Methods for the treatment of central nervous system disorders in certain patient groups |
| US6881741B2 (en) * | 2001-06-11 | 2005-04-19 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| WO2003000194A2 (en) * | 2001-06-21 | 2003-01-03 | Pfizer Inc. | Thienopyridine and thienopyrimidine anticancer agents |
| KR101058696B1 (ko) * | 2002-12-10 | 2011-08-22 | 바이로켐 파마 인코포레이티드 | 후라비바이러스 감염의 치료 또는 예방을 위한 화합물과방법 |
| US7994192B2 (en) * | 2006-09-26 | 2011-08-09 | Crestone, Inc. | Substituted thienopyridone compounds with antibacterial activity |
| US7973050B2 (en) * | 2006-09-26 | 2011-07-05 | Crestone, Inc. | Enantiomeric compounds with antibacterial activity |
| WO2008039639A2 (en) * | 2006-09-26 | 2008-04-03 | Crestone, Inc. | Substituted thienopyridone compounds with antibacterial activity |
| WO2008039642A2 (en) * | 2006-09-26 | 2008-04-03 | Replidyne, Inc. | Methods and compounds for treatment of clostridium based infection |
| US8697720B2 (en) | 2006-09-26 | 2014-04-15 | Crestone, Inc. | Substituted phenylether-thienopyridone compounds with antibacterial activity |
| JP5290186B2 (ja) * | 2006-11-15 | 2013-09-18 | ヴァイロケム ファーマ インコーポレイテッド | フラビウイルス感染症の治療または予防用のチオフェン類似体 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997545A (en) * | 1973-07-23 | 1976-12-14 | Takeda Chemical Industries, Ltd. | Thienopyridine-carboxylic acid derivatives |
| NZ193167A (en) * | 1979-03-27 | 1984-08-24 | Boots Co Plc | Quinoline derivatives and pharmaceutical compositions |
| JPS5742690A (en) * | 1980-08-28 | 1982-03-10 | Kanebo Ltd | Thieno 3,2-b pyridinecarboxylic acid derivative |
| GB2085441B (en) * | 1980-09-26 | 1984-10-17 | Boots The Co Ltd | Therapeutic agents |
| IE51542B1 (en) * | 1980-09-26 | 1987-01-07 | Boots Co Ltd | Therapeutic agents |
| DE3412947A1 (de) * | 1984-04-06 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | Tetrahydothienopyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1985
- 1985-06-15 GB GB858515207A patent/GB8515207D0/en active Pending
-
1986
- 1986-06-05 AU AU58383/86A patent/AU581595B2/en not_active Expired - Fee Related
- 1986-06-09 EP EP86304382A patent/EP0209977A3/de not_active Withdrawn
- 1986-06-09 PH PH33869A patent/PH22293A/en unknown
- 1986-06-10 YU YU00993/86A patent/YU99386A/xx unknown
- 1986-06-10 DK DK272486A patent/DK272486A/da not_active Application Discontinuation
- 1986-06-12 PT PT82759A patent/PT82759B/pt unknown
- 1986-06-12 CS CS864362A patent/CS258483B2/cs unknown
- 1986-06-12 FI FI862520A patent/FI862520A7/fi not_active Application Discontinuation
- 1986-06-12 ZA ZA864396A patent/ZA864396B/xx unknown
- 1986-06-12 GR GR861527A patent/GR861527B/el unknown
- 1986-06-13 US US06/874,337 patent/US4710506A/en not_active Expired - Lifetime
- 1986-06-13 ES ES556026A patent/ES8707243A1/es not_active Expired
- 1986-06-13 HU HU862521A patent/HU195661B/hu not_active IP Right Cessation
- 1986-06-13 DD DD86291289A patent/DD253823A5/de unknown
- 1986-06-13 NO NO862373A patent/NO862373L/no unknown
- 1986-06-14 JO JO19861482A patent/JO1482B1/en active
- 1986-06-14 KR KR1019860004737A patent/KR870000339A/ko not_active Withdrawn
- 1986-06-16 JP JP61139953A patent/JPS6236382A/ja active Pending
- 1986-06-16 PL PL1986266392A patent/PL266392A1/xx unknown
-
1987
- 1987-06-29 YU YU01211/87A patent/YU121187A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT82759A (en) | 1986-07-01 |
| DK272486D0 (da) | 1986-06-10 |
| GB8515207D0 (en) | 1985-07-17 |
| PL266392A1 (en) | 1988-02-18 |
| NO862373D0 (no) | 1986-06-13 |
| YU121187A (en) | 1988-04-30 |
| FI862520L (fi) | 1986-12-16 |
| KR870000339A (ko) | 1987-02-17 |
| HUT42775A (en) | 1987-08-28 |
| GR861527B (en) | 1986-10-14 |
| DK272486A (da) | 1986-12-16 |
| PT82759B (en) | 1988-05-12 |
| AU581595B2 (en) | 1989-02-23 |
| CS436286A2 (en) | 1987-12-17 |
| PH22293A (en) | 1988-07-22 |
| EP0209977A3 (de) | 1988-06-08 |
| JO1482B1 (en) | 1988-03-10 |
| JPS6236382A (ja) | 1987-02-17 |
| HU195661B (en) | 1988-06-28 |
| FI862520A0 (fi) | 1986-06-12 |
| DD253823A5 (de) | 1988-02-03 |
| NO862373L (no) | 1986-12-16 |
| US4710506A (en) | 1987-12-01 |
| FI862520A7 (fi) | 1986-12-16 |
| ES8707243A1 (es) | 1987-07-16 |
| ZA864396B (en) | 1987-08-26 |
| EP0209977A2 (de) | 1987-01-28 |
| ES556026A0 (es) | 1987-07-16 |
| AU5838386A (en) | 1986-12-18 |
| YU99386A (en) | 1988-04-30 |
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