IE43915B1 - Improvements in or relating to new thieno/2,3-c/pyridine derivatives - Google Patents
Improvements in or relating to new thieno/2,3-c/pyridine derivativesInfo
- Publication number
- IE43915B1 IE43915B1 IE1149/76A IE114976A IE43915B1 IE 43915 B1 IE43915 B1 IE 43915B1 IE 1149/76 A IE1149/76 A IE 1149/76A IE 114976 A IE114976 A IE 114976A IE 43915 B1 IE43915 B1 IE 43915B1
- Authority
- IE
- Ireland
- Prior art keywords
- derivative
- formula
- derivatives
- thieno
- carbon atoms
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 210000001772 blood platelet Anatomy 0.000 claims abstract description 13
- -1 phenoxy, benzoyl Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 10
- 230000003288 anthiarrhythmic effect Effects 0.000 claims abstract description 9
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical class C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 229940092253 ovalbumin Drugs 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229940102884 adrenalin Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- 230000033764 rhythmic process Effects 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 2
- 229960003343 ouabain Drugs 0.000 description 2
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- QSLMPDKYTNEMFQ-UHFFFAOYSA-N 2-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CBr QSLMPDKYTNEMFQ-UHFFFAOYSA-N 0.000 description 1
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003662 Atrial flutter Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010027783 Moaning Diseases 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 208000007888 Sinus Tachycardia Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000003734 Supraventricular Tachycardia Diseases 0.000 description 1
- 206010042602 Supraventricular extrasystoles Diseases 0.000 description 1
- 206010049447 Tachyarrhythmia Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000007817 turbidimetric assay 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7520241A FR2315274A1 (fr) | 1975-06-27 | 1975-06-27 | Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43915L IE43915L (en) | 1976-12-27 |
| IE43915B1 true IE43915B1 (en) | 1981-07-01 |
Family
ID=9157178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1149/76A IE43915B1 (en) | 1975-06-27 | 1976-05-31 | Improvements in or relating to new thieno/2,3-c/pyridine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4075340A (en:Method) |
| JP (1) | JPS607633B2 (en:Method) |
| AR (1) | AR211777A1 (en:Method) |
| AT (1) | AT347950B (en:Method) |
| BE (1) | BE843402A (en:Method) |
| CA (1) | CA1071635A (en:Method) |
| CH (1) | CH596169A5 (en:Method) |
| DD (1) | DD125080A5 (en:Method) |
| DE (1) | DE2628045A1 (en:Method) |
| DK (1) | DK279976A (en:Method) |
| ES (1) | ES449191A1 (en:Method) |
| FR (1) | FR2315274A1 (en:Method) |
| GB (1) | GB1492239A (en:Method) |
| GR (1) | GR60042B (en:Method) |
| HU (1) | HU172697B (en:Method) |
| IE (1) | IE43915B1 (en:Method) |
| IL (1) | IL49702A (en:Method) |
| LU (1) | LU75230A1 (en:Method) |
| MX (1) | MX3565E (en:Method) |
| NL (1) | NL183032C (en:Method) |
| PL (1) | PL105962B1 (en:Method) |
| PT (1) | PT65271B (en:Method) |
| SE (1) | SE421698B (en:Method) |
| SU (1) | SU628820A3 (en:Method) |
| YU (1) | YU39480B (en:Method) |
| ZA (1) | ZA763270B (en:Method) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| FR2395271A1 (fr) * | 1977-06-21 | 1979-01-19 | Parcor | Procede de preparation de thieno (2,3-c) et thieno (3,2-c) pyridines |
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| GB2038625B (en) * | 1978-12-29 | 1983-01-12 | Parcor | Therapeutic composition having an antithrombotic and antiblood-platelet-aggregating activity |
| FR2397417A1 (fr) * | 1977-07-12 | 1979-02-09 | Parcor | Procede de preparation de derives de la thienopyridine |
| AT368504B (de) * | 1977-10-15 | 1982-10-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 4-phenyl-thieno- (2,3-c)-piperidine |
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| FR2508453A1 (fr) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation de derives des (thienyl-2)- et thienyl-3)-2 ethylamines et produits ainsi obtenus |
| US4547514A (en) * | 1983-12-05 | 1985-10-15 | A. H. Robins Company, Incorporated | Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity |
| DE3736664A1 (de) * | 1987-10-29 | 1989-05-11 | Boehringer Ingelheim Kg | Tetrahydro-furo- und -thieno(2,3-c)pyridine, ihre verwendung als arzneimittel und verfahren zu ihrer herstellung |
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| US9662490B2 (en) | 2008-03-31 | 2017-05-30 | The Feinstein Institute For Medical Research | Methods and systems for reducing inflammation by neuromodulation and administration of an anti-inflammatory drug |
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| EP2707094B1 (en) | 2011-05-09 | 2016-02-03 | Setpoint Medical Corporation | Single-pulse activation of the cholinergic anti-inflammatory pathway to treat chronic inflammation |
| US12172017B2 (en) | 2011-05-09 | 2024-12-24 | Setpoint Medical Corporation | Vagus nerve stimulation to treat neurodegenerative disorders |
| JP6117334B2 (ja) | 2012-03-23 | 2017-04-19 | メモリアル スローン−ケタリング キャンサー センター | 膵臓癌および関連するがんの５−アシル−６，７−ジヒドロチエノ［３，２−ｃ］ピリジンでの処置 |
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| WO2016126807A1 (en) | 2015-02-03 | 2016-08-11 | Setpoint Medical Corporation | Apparatus and method for reminding, prompting, or alerting a patient with an implanted stimulator |
| US10596367B2 (en) | 2016-01-13 | 2020-03-24 | Setpoint Medical Corporation | Systems and methods for establishing a nerve block |
| EP3405107B1 (en) | 2016-01-20 | 2023-04-12 | Setpoint Medical Corporation | Control of vagal stimulation |
| US11471681B2 (en) | 2016-01-20 | 2022-10-18 | Setpoint Medical Corporation | Batteryless implantable microstimulators |
| EP3405255A4 (en) | 2016-01-20 | 2019-10-16 | Setpoint Medical Corporation | IMPLANTABLE MICROSTIMULATORS AND INDUCTIVE CHARGING SYSTEMS |
| US10583304B2 (en) | 2016-01-25 | 2020-03-10 | Setpoint Medical Corporation | Implantable neurostimulator having power control and thermal regulation and methods of use |
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| CN113939334A (zh) | 2019-04-12 | 2022-01-14 | 赛博恩特医疗器械公司 | 迷走神经刺激来处理神经退行性障碍 |
| KR20230012585A (ko) | 2020-05-21 | 2023-01-26 | 더 파인스타인 인스티튜츠 포 메디칼 리서치 | 미주 신경 자극을 위한 시스템들 및 방법들 |
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Family Cites Families (1)
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| FR2215948B1 (en:Method) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma |
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1975
- 1975-06-27 FR FR7520241A patent/FR2315274A1/fr active Granted
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1976
- 1976-05-17 CH CH612276A patent/CH596169A5/xx not_active IP Right Cessation
- 1976-05-31 IE IE1149/76A patent/IE43915B1/en unknown
- 1976-06-01 GR GR50863A patent/GR60042B/el unknown
- 1976-06-01 IL IL49702A patent/IL49702A/xx unknown
- 1976-06-02 US US05/692,186 patent/US4075340A/en not_active Expired - Lifetime
- 1976-06-02 ZA ZA763270A patent/ZA763270B/xx unknown
- 1976-06-14 SU SU762367256A patent/SU628820A3/ru active
- 1976-06-15 YU YU1462/76A patent/YU39480B/xx unknown
- 1976-06-17 NL NLAANVRAGE7606574,A patent/NL183032C/xx not_active IP Right Cessation
- 1976-06-21 CA CA255,299A patent/CA1071635A/en not_active Expired
- 1976-06-22 DK DK279976A patent/DK279976A/da unknown
- 1976-06-23 DE DE19762628045 patent/DE2628045A1/de not_active Ceased
- 1976-06-23 SE SE7607201A patent/SE421698B/xx not_active IP Right Cessation
- 1976-06-24 AR AR263737A patent/AR211777A1/es active
- 1976-06-24 PT PT65271A patent/PT65271B/pt unknown
- 1976-06-24 AT AT461776A patent/AT347950B/de not_active IP Right Cessation
- 1976-06-24 LU LU75230A patent/LU75230A1/xx unknown
- 1976-06-25 GB GB26591/76A patent/GB1492239A/en not_active Expired
- 1976-06-25 ES ES449191A patent/ES449191A1/es not_active Expired
- 1976-06-25 HU HU76PA00001254A patent/HU172697B/hu not_active IP Right Cessation
- 1976-06-25 MX MX76799U patent/MX3565E/es unknown
- 1976-06-25 BE BE168304A patent/BE843402A/xx not_active IP Right Cessation
- 1976-06-25 DD DD193581A patent/DD125080A5/xx unknown
- 1976-06-26 PL PL1976190741A patent/PL105962B1/pl unknown
- 1976-06-26 JP JP51075943A patent/JPS607633B2/ja not_active Expired
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