NO770188L - Fremgangsm}te for fremstilling av nye thieno(3,2-c)pyridinderivater. - Google Patents
Fremgangsm}te for fremstilling av nye thieno(3,2-c)pyridinderivater.Info
- Publication number
- NO770188L NO770188L NO770188A NO770188A NO770188L NO 770188 L NO770188 L NO 770188L NO 770188 A NO770188 A NO 770188A NO 770188 A NO770188 A NO 770188A NO 770188 L NO770188 L NO 770188L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- derivative
- denotes
- denotes hydrogen
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 9
- PYEZYNAHBMWJFR-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical class N1=CC=C2S[C]=CC2=C1 PYEZYNAHBMWJFR-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy- Chemical class 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical class N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 9
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 230000001624 sedative effect Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940092253 ovalbumin Drugs 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 229920001525 carrageenan Polymers 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
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 206010029216 Nervousness Diseases 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-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
- 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
- 208000019901 Anxiety disease Diseases 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- YFMASFVLIUNTTR-UHFFFAOYSA-N ethyl 3-acetyloxy-5-[(2-chlorophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C1C=2C(OC(C)=O)=C(C(=O)OCC)SC=2CCN1CC1=CC=CC=C1Cl YFMASFVLIUNTTR-UHFFFAOYSA-N 0.000 description 1
- UIDRKADTANXAOR-UHFFFAOYSA-N ethyl 4-(2-methoxy-2-oxoethyl)sulfanyl-1,2,3,6-tetrahydropyridine-5-carboxylate Chemical compound CCOC(=O)C1=C(SCC(=O)OC)CCNC1 UIDRKADTANXAOR-UHFFFAOYSA-N 0.000 description 1
- WBPZZHLGJQYVAA-UHFFFAOYSA-N ethyl 5-[(2-chlorophenyl)methyl]-3-hydroxy-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C1C=2C(O)=C(C(=O)OCC)SC=2CCN1CC1=CC=CC=C1Cl WBPZZHLGJQYVAA-UHFFFAOYSA-N 0.000 description 1
- JNKRFJFOXHPNEJ-UHFFFAOYSA-N ethyl 5-benzoyl-3-hydroxy-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C1C=2C(O)=C(C(=O)OCC)SC=2CCN1C(=O)C1=CC=CC=C1 JNKRFJFOXHPNEJ-UHFFFAOYSA-N 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- ITBNXIMKMBVDRC-UHFFFAOYSA-N methyl 1-[(2-chlorophenyl)methyl]-4-oxopiperidine-3-carboxylate;hydrochloride Chemical compound Cl.C1CC(=O)C(C(=O)OC)CN1CC1=CC=CC=C1Cl ITBNXIMKMBVDRC-UHFFFAOYSA-N 0.000 description 1
- PZZCHYLJJBNOAB-UHFFFAOYSA-N methyl 1-benzoyl-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1C(=O)C1=CC=CC=C1 PZZCHYLJJBNOAB-UHFFFAOYSA-N 0.000 description 1
- DOZYWLKBROZBSC-UHFFFAOYSA-N methyl 3-hydroxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate Chemical compound C1CNCC2=C1SC(C(=O)OC)=C2O DOZYWLKBROZBSC-UHFFFAOYSA-N 0.000 description 1
- PULQLHKDLLBVKM-UHFFFAOYSA-N methyl 4-(2-butoxy-2-oxoethyl)sulfanyl-1-[(2-chlorophenyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1CC(SCC(=O)OCCCC)=C(C(=O)OC)CN1CC1=CC=CC=C1Cl PULQLHKDLLBVKM-UHFFFAOYSA-N 0.000 description 1
- KOBIXQWUYVKCIW-UHFFFAOYSA-N methyl 5-[(2-chlorophenyl)methyl]-3-hydroxy-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C1C=2C(O)=C(C(=O)OC)SC=2CCN1CC1=CC=CC=C1Cl KOBIXQWUYVKCIW-UHFFFAOYSA-N 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- XXRTUTXQDPQYDA-UHFFFAOYSA-N thieno[3,2-c]pyridine;hydrochloride Chemical compound Cl.N1=CC=C2SC=CC2=C1 XXRTUTXQDPQYDA-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7601637A FR2338703A1 (fr) | 1976-01-22 | 1976-01-22 | Derives de thieno (3,2-c) pyridine, leur procede de preparation et leurs applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO770188L true NO770188L (no) | 1977-07-25 |
Family
ID=9168219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770188A NO770188L (no) | 1976-01-22 | 1977-01-21 | Fremgangsm}te for fremstilling av nye thieno(3,2-c)pyridinderivater. |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4136186A (de) |
| JP (1) | JPS5291891A (de) |
| AR (1) | AR215611A1 (de) |
| AT (1) | AT352729B (de) |
| AU (1) | AU509528B2 (de) |
| BE (1) | BE850620A (de) |
| CA (1) | CA1072097A (de) |
| CH (1) | CH618173A5 (de) |
| DD (1) | DD128131A5 (de) |
| DE (1) | DE2701511A1 (de) |
| DK (1) | DK147825C (de) |
| ES (1) | ES455023A1 (de) |
| FI (1) | FI61901C (de) |
| FR (1) | FR2338703A1 (de) |
| GB (1) | GB1529527A (de) |
| GR (1) | GR62519B (de) |
| HU (1) | HU172514B (de) |
| IE (1) | IE44305B1 (de) |
| IL (1) | IL51274A (de) |
| LU (1) | LU76561A1 (de) |
| MX (1) | MX3945E (de) |
| NL (1) | NL7700201A (de) |
| NO (1) | NO770188L (de) |
| NZ (1) | NZ183141A (de) |
| PH (1) | PH14709A (de) |
| PL (1) | PL101879B1 (de) |
| PT (1) | PT66073B (de) |
| RO (1) | RO69711A (de) |
| SE (1) | SE421700B (de) |
| SU (1) | SU656521A3 (de) |
| YU (1) | YU39789B (de) |
| ZA (1) | ZA77307B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2495157A1 (fr) * | 1980-11-28 | 1982-06-04 | Sanofi Sa | Procede nouveau de preparation des tetrahydro-5, 6, 7, 7a 4h-thieno (3, 2-c) pyridinones-2 |
| US4775757A (en) * | 1986-09-22 | 1988-10-04 | Ortho Pharmaceutical Corporation | Thienopyridines useful as cardiovascular agents |
| FI101150B (fi) * | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| US5296603A (en) * | 1992-06-08 | 1994-03-22 | Fuji Photo Film Co., Ltd. | 3-amino-5-o-chlorobenzyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine-2-carboxylic acid compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075215A (en) * | 1973-02-01 | 1978-02-21 | Centre D'etudes Pour L'industrie Pharmaceutique | Thieno-pyridine derivatives |
| FR2215948B1 (de) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma |
-
1976
- 1976-01-22 FR FR7601637A patent/FR2338703A1/fr active Granted
-
1977
- 1977-01-10 YU YU42/77A patent/YU39789B/xx unknown
- 1977-01-10 NL NL7700201A patent/NL7700201A/xx not_active Application Discontinuation
- 1977-01-10 PH PH19362A patent/PH14709A/en unknown
- 1977-01-11 CH CH30977A patent/CH618173A5/fr not_active IP Right Cessation
- 1977-01-11 HU HU77PA00001274A patent/HU172514B/hu unknown
- 1977-01-11 GR GR52546A patent/GR62519B/el unknown
- 1977-01-13 IE IE57/77A patent/IE44305B1/en unknown
- 1977-01-13 US US05/763,876 patent/US4136186A/en not_active Expired - Lifetime
- 1977-01-13 LU LU76561A patent/LU76561A1/xx unknown
- 1977-01-14 PT PT66073A patent/PT66073B/pt unknown
- 1977-01-14 AT AT19777A patent/AT352729B/de not_active IP Right Cessation
- 1977-01-14 ES ES455023A patent/ES455023A1/es not_active Expired
- 1977-01-15 DE DE19772701511 patent/DE2701511A1/de not_active Ceased
- 1977-01-15 RO RO7789063A patent/RO69711A/ro unknown
- 1977-01-17 IL IL51274A patent/IL51274A/xx unknown
- 1977-01-19 GB GB2144/77A patent/GB1529527A/en not_active Expired
- 1977-01-19 CA CA270,070A patent/CA1072097A/en not_active Expired
- 1977-01-19 ZA ZA77307A patent/ZA77307B/xx unknown
- 1977-01-20 DD DD7700197020A patent/DD128131A5/de unknown
- 1977-01-20 SE SE7700572A patent/SE421700B/xx unknown
- 1977-01-20 DK DK21477A patent/DK147825C/da not_active IP Right Cessation
- 1977-01-20 FI FI770180A patent/FI61901C/fi not_active IP Right Cessation
- 1977-01-21 AR AR266274A patent/AR215611A1/es active
- 1977-01-21 NO NO770188A patent/NO770188L/no unknown
- 1977-01-21 PL PL1977195466A patent/PL101879B1/pl unknown
- 1977-01-21 SU SU772446153A patent/SU656521A3/ru active
- 1977-01-21 BE BE174269A patent/BE850620A/xx not_active IP Right Cessation
- 1977-01-21 NZ NZ183141A patent/NZ183141A/xx unknown
- 1977-01-21 MX MX775374U patent/MX3945E/es unknown
- 1977-01-21 AU AU21549/77A patent/AU509528B2/en not_active Expired
- 1977-01-22 JP JP632477A patent/JPS5291891A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI79846C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla heteroaromatiska aminderivat. | |
| NO152048B (no) | Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 5h-2,3-benzodiazepinderivater | |
| HU197735B (en) | Process for producing ascorbinic acid derivatives and pharmaceutical compositions containing them | |
| US3755583A (en) | Chas0!nhx | |
| NO312897B1 (no) | Nye alkylerte (hetero)cykliske forbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetningerinneholdende dem | |
| CN113087713B (zh) | 一类苯并二氮䓬衍生物及其制备方法和用途 | |
| JPS6254109B2 (de) | ||
| NO770188L (no) | Fremgangsm}te for fremstilling av nye thieno(3,2-c)pyridinderivater. | |
| AU2020276005B2 (en) | 3-aryloxyl-3-five-membered heteroaryl propylamine compound, and crystal form and use thereof | |
| NO780050L (no) | Fremgangsmaate ved fremstilling av 4,5,6,7-tetrahydrothieno-(2,3-c) og (3,2-c)pyridiner | |
| DE69837334T2 (de) | Heterozyclische verbindungen, ihr herstellungsverfahren und diese enthaltende pharmazeutische zusammensetzungen | |
| HU182884B (en) | Process for preparing 4-phenyl-1,3-benzodiazepine derivatives and pharmaceutically acceptable salts and optical antipodes thereof further pharmaceutical compositions containing these compounds as active substances | |
| DK165691B (da) | Tricykliske aminer afledt af 2,3,5,6,7,8-hexahydronaphtho(2,3-b)furan, fremgangsmaade til deres fremstilling og farmaceutiske midler indeholdende dem | |
| FI83317C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla i 11-staellning substituerade 5,11-dihydro-6h -pyrido/2,3-b//1,4/bensodiazepin-6-oner. | |
| EP0000108A1 (de) | Benzo(b)thienopyridine, Verfahren zu deren Herstellung und diese enthaltende therapeutische Präparate | |
| JP2006522012A (ja) | ベンゾキサゾシンおよびそのモノアミン再吸収阻害剤としての用途 | |
| US4420476A (en) | Benzofuro[3,2-c]pyrazol-3-amine derivatives | |
| US3946018A (en) | 1,4-Dihydro-3 (2H)-isoquinolinone derivatives | |
| US4431657A (en) | Analgesic compositions consisting of 2H-benzothieno[3,2-c]pyrazol-3-amine derivatives | |
| US4539402A (en) | Quinazolinone derivatives | |
| Elliott et al. | Central nervous system activity of 7-substituted 1-azaphenoxathiin analogs and their oxidation products | |
| US3764684A (en) | Novel indolobenzazepine derivatives, useful as tranquilizers | |
| NO150207B (no) | Fremgangsmaate ved fremstilling av thieno (2,3-c) og (3,2-c) pyridiner | |
| FI88502C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1-/3-(2-aminoetoxi)-2-tienyl/-3-fenyl-1-propanoner | |
| JP2008528677A (ja) | Ｃｎｓの疾患および障害の処置のための四環系モノアミン再取り込み阻害薬 |