DD253823A5 - Verfahren zur herstellung neuartiger thienopyridone - Google Patents

Verfahren zur herstellung neuartiger thienopyridone Download PDF

Info

Publication number: DD253823A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; methyl; mixture; compounds
Prior art date: 1985-06-15

Application number

DD86291289A

Other languages

German (de)

English (en)

Inventor

Roy V Davies

James Fraser

Original Assignee

��@��@��@��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.)

1985-06-15

Filing date

1986-06-13

Publication date

1988-02-03

1986-06-13 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1988-02-03 Publication of DD253823A5 publication Critical patent/DD253823A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 181
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 8
-1 compound Compound Chemical class 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 6
150000003839 salts Chemical class 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 3
230000001077 hypotensive effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
239000000203 mixture Substances 0.000 description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 32
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
239000012265 solid product Substances 0.000 description 23
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
239000000047 product Substances 0.000 description 19
238000001914 filtration Methods 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 17
230000036772 blood pressure Effects 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
229940125670 thienopyridine Drugs 0.000 description 14
239000002175 thienopyridine Substances 0.000 description 14
239000012258 stirred mixture Substances 0.000 description 13
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 11
238000009835 boiling Methods 0.000 description 11
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 9
239000003480 eluent Substances 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
239000000284 extract Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000007787 solid Substances 0.000 description 8
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
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 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
239000000725 suspension Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
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 5
238000000354 decomposition reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
230000001225 therapeutic effect Effects 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
238000001816 cooling Methods 0.000 description 4
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000015096 spirit Nutrition 0.000 description 4
GKFLKOFXONRIGL-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound S1C=2C(=O)C(SC)=CN(C)C=2C=C1C1=CC=CC=C1Cl GKFLKOFXONRIGL-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
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
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 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 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
239000011928 denatured alcohol Substances 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
150000004967 organic peroxy acids Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000523 sample 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
FKNKKPFULFAZLX-UHFFFAOYSA-N thieno[3,4-b]pyridine Chemical compound N1=CC=CC2=CSC=C21 FKNKKPFULFAZLX-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
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
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 2
UJQZFMIHWWTZBJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-methyl-6-methylsulfanylthieno[3,2-b]pyridin-7-one Chemical compound S1C=2C(=O)C(SC)=CN(C)C=2C=C1C1=CC=CC(Cl)=C1 UJQZFMIHWWTZBJ-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
SWALGAGZRWJLCT-UHFFFAOYSA-N 4-methyl-6-(methylsulfonylmethyl)thieno[3,2-b]pyridin-7-one Chemical compound CN1C=C(CS(C)(=O)=O)C(=O)C2=C1C=CS2 SWALGAGZRWJLCT-UHFFFAOYSA-N 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
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 description 2
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 2
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 2
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 2
SIFNGOZBWWIMRR-UHFFFAOYSA-N 7-methyl-5-methylsulfanylthieno[2,3-b]pyridin-4-one Chemical compound O=C1C(SC)=CN(C)C2=C1C=CS2 SIFNGOZBWWIMRR-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VBRNRDNUFZHVMD-UHFFFAOYSA-N CC(C=CN=C1C2=O)C1=C[S+]2SC Chemical compound CC(C=CN=C1C2=O)C1=C[S+]2SC VBRNRDNUFZHVMD-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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
229920002472 Starch Polymers 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
210000001367 artery Anatomy 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 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
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 2
TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere 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
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
230000010349 pulsation Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
239000000829 suppository Substances 0.000 description 2
SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
150000003577 thiophenes Chemical class 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
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GWNZXHGUNFBXNX-UHFFFAOYSA-N thieno[3,4-b]pyridine 6-oxide Chemical class C1=CC=NC2=CS(=O)C=C21 GWNZXHGUNFBXNX-UHFFFAOYSA-N 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
YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (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)

DD86291289A 1985-06-15 1986-06-13 Verfahren zur herstellung neuartiger thienopyridone DD253823A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858515207A GB8515207D0 (en)	1985-06-15	1985-06-15	Therapeutic agents

Publications (1)

Publication Number	Publication Date
DD253823A5 true DD253823A5 (de)	1988-02-03

Family

ID=10580803

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86291289A DD253823A5 (de)	1985-06-15	1986-06-13	Verfahren zur herstellung neuartiger thienopyridone

Country Status (20)

Country	Link
US (1)	US4710506A (cs)
EP (1)	EP0209977A3 (cs)
JP (1)	JPS6236382A (cs)
KR (1)	KR870000339A (cs)
AU (1)	AU581595B2 (cs)
CS (1)	CS258483B2 (cs)
DD (1)	DD253823A5 (cs)
DK (1)	DK272486A (cs)
ES (1)	ES8707243A1 (cs)
FI (1)	FI862520A7 (cs)
GB (1)	GB8515207D0 (cs)
GR (1)	GR861527B (cs)
HU (1)	HU195661B (cs)
JO (1)	JO1482B1 (cs)
NO (1)	NO862373L (cs)
PH (1)	PH22293A (cs)
PL (1)	PL266392A1 (cs)
PT (1)	PT82759B (cs)
YU (2)	YU99386A (cs)
ZA (1)	ZA864396B (cs)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
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
JP2002522388A (ja) *	1998-08-03	2002-07-23	ビーエーエスエフコーポレーション	性機能障害の治療のためのピリジノン
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
US8329924B2 (en) *	2001-06-11	2012-12-11	Vertex Pharmaceuticals (Canada) Incorporated	Compounds and methods for the treatment or prevention of Flavivirus infections
AU2002344854B2 (en) *	2001-06-11	2008-11-06	Vertex Pharmaceuticals (Canada) Incorporated	Thiophene derivatives as antiviral agents for flavivirus infection
WO2003000194A2 (en) *	2001-06-21	2003-01-03	Pfizer Inc.	Thienopyridine and thienopyrimidine anticancer agents
CN100413861C (zh)	2002-12-10	2008-08-27	维勒凯姆制药股份有限公司	用于治疗或预防黄病毒感染的化合物
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
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
PT2104674E (pt)	2006-11-15	2013-07-26	Virochem Pharma Inc	Análogos de tiofeno para o tratamento ou prevenção de infeções por flavivírus

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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 PH PH33869A patent/PH22293A/en unknown
- 1986-06-09 EP EP86304382A patent/EP0209977A3/en not_active Withdrawn
- 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 CS CS864362A patent/CS258483B2/cs unknown
- 1986-06-12 PT PT82759A patent/PT82759B/pt 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 DD DD86291289A patent/DD253823A5/de unknown
- 1986-06-13 HU HU862521A patent/HU195661B/hu not_active IP Right Cessation
- 1986-06-13 US US06/874,337 patent/US4710506A/en not_active Expired - Lifetime
- 1986-06-13 NO NO862373A patent/NO862373L/no unknown
- 1986-06-13 ES ES556026A patent/ES8707243A1/es not_active Expired
- 1986-06-14 JO JO19861482A patent/JO1482B1/en active
- 1986-06-14 KR KR1019860004737A patent/KR870000339A/ko not_active Withdrawn
- 1986-06-16 PL PL1986266392A patent/PL266392A1/xx unknown
- 1986-06-16 JP JP61139953A patent/JPS6236382A/ja active Pending
1987
- 1987-06-29 YU YU01211/87A patent/YU121187A/xx unknown

Also Published As

Publication number	Publication date
CS258483B2 (en)	1988-08-16
GB8515207D0 (en)	1985-07-17
ES556026A0 (es)	1987-07-16
JO1482B1 (en)	1988-03-10
PH22293A (en)	1988-07-22
NO862373D0 (no)	1986-06-13
GR861527B (en)	1986-10-14
HUT42775A (en)	1987-08-28
AU5838386A (en)	1986-12-18
ZA864396B (en)	1987-08-26
HU195661B (en)	1988-06-28
YU121187A (en)	1988-04-30
PT82759A (en)	1986-07-01
YU99386A (en)	1988-04-30
EP0209977A3 (en)	1988-06-08
EP0209977A2 (en)	1987-01-28
PL266392A1 (en)	1988-02-18
US4710506A (en)	1987-12-01
AU581595B2 (en)	1989-02-23
PT82759B (en)	1988-05-12
ES8707243A1 (es)	1987-07-16
JPS6236382A (ja)	1987-02-17
KR870000339A (ko)	1987-02-17
FI862520A0 (fi)	1986-06-12
NO862373L (no)	1986-12-16
CS436286A2 (en)	1987-12-17
DK272486A (da)	1986-12-16
FI862520L (fi)	1986-12-16
DK272486D0 (da)	1986-06-10
FI862520A7 (fi)	1986-12-16

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DE60216823T2 (de)	2007-10-04	Zwischenprodukten für die Herstellung von Pyridazinon Aldose Reductase Inhibitoren.
DE3881408T2 (de)	1994-01-20	Thiazolidinon-Derivate, ihre Herstellung und ihre Verwendung.
DE69309670T2 (de)	1997-11-20	Heterocyclische carbonsäure-derivate, die an rar rezeptoren binden können
DE69331122T2 (de)	2002-06-20	4-Aminochinazolin-Derivate, deren Verwendung als Heilmittel
DE69113148T2 (de)	1996-03-28	Thioxo-Heterocyclen und ihre pharmazeutische Verwendung.
DE69115134T2 (de)	1996-06-13	Pyranderivate zur Verwendung als 5-Lipoxygenasehemmer.
DE69912618T2 (de)	2004-10-28	NEUE THIENO[2,3-d]PYRIMIDINDIONE, VERFAHREN FÜR IHRE HERSTELLUNG UND IHRE VERWENDUNG IN DER THERAPIE
DE19709877A1 (de)	1998-09-17	1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate
US4710506A (en)	1987-12-01	Antihypertensive thienopyridines
EP0183159A2 (de)	1986-06-04	1-Heteroaryl-4-aryl-pyrazolin-5-one zur Verwendung als Arzneimittel
EP0011142B1 (de)	1982-12-29	Pyrido (2,1-b) chinazolinon-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DE3533331A1 (de)	1987-03-26	Pyridothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0258729A2 (de)	1988-03-09	Dihydropyridinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE69408593T2 (de)	1998-07-16	4-Aryl-4-Hydroxy-Tetrahydropyrane und 3-Aryl-3-Hydroxy-Tetrahydrofurane als 5-Lipoxygenaseinhibitoren
DE3509333A1 (de)	1986-09-18	Substituierte benzimidazolderivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer
DE68924308T2 (de)	1996-04-04	Pyridazinon-Derivate.
EP0519291B1 (de)	1997-01-08	Aminomethyl-substituierte 2,3-Dihydropyrano(2,3-b)pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0378850B1 (de)	1994-04-06	Neue substituierte Pyrido(2,3-d)pyrimidine
DE68924221T2 (de)	1996-02-15	Imidazolderivate.
DE3687945T2 (de)	1993-07-01	((((3-pyridinyl)methylen)amino)oxy)alkansaeuren und -ester.
EP0013732A2 (de)	1980-08-06	Imidazolderivate, Verfahren zu ihrer Herstellung und diese Imidazolderivate enthaltende pharmazeutische Zusammensetzungen
DE60129445T2 (de)	2008-04-24	Quinolin-derivate als antientzündungsmittel
EP0163842A1 (de)	1985-12-11	Tricyclische Imidazolderivate
DE2921001A1 (de)	1979-11-29	Tetrahydrothiopyrano eckige klammer auf 2,3-b eckige klammer zu indolderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
DD201890A5 (de)	1983-08-17	Verfahren zur herstellung neuartiger chinolonverbindungen