NO300809B1 - Tricykliske kondenserte heterocykliske forbindelser og deres anvendelse - Google Patents
Tricykliske kondenserte heterocykliske forbindelser og deres anvendelse Download PDFInfo
- Publication number
- NO300809B1 NO300809B1 NO940163A NO940163A NO300809B1 NO 300809 B1 NO300809 B1 NO 300809B1 NO 940163 A NO940163 A NO 940163A NO 940163 A NO940163 A NO 940163A NO 300809 B1 NO300809 B1 NO 300809B1
- Authority
- NO
- Norway
- Prior art keywords
- salt
- piperidinyl
- group
- pyrrolo
- compound
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 150000003839 salts Chemical class 0.000 claims abstract description 120
- -1 1-piperazinyl Chemical group 0.000 claims abstract description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 102000003914 Cholinesterases Human genes 0.000 claims abstract description 12
- 108090000322 Cholinesterases Proteins 0.000 claims abstract description 12
- 229940048961 cholinesterase Drugs 0.000 claims abstract description 12
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- JBDJOGWUZUGUGQ-UHFFFAOYSA-N 1-(2-benzyl-1,3-dihydrobenzo[de]isoquinolin-6-yl)-3-(1-benzylpiperidin-4-yl)propan-1-one Chemical compound C=1C=C(C=23)CN(CC=4C=CC=CC=4)CC3=CC=CC=2C=1C(=O)CCC(CC1)CCN1CC1=CC=CC=C1 JBDJOGWUZUGUGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- HNBRYFZSXNGYNV-UHFFFAOYSA-N 6-[3-(4-benzylpiperidin-1-yl)propanoyl]-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-11-one Chemical compound C=1C=2CCN(C(CC3)=O)C=2C3=CC=1C(=O)CCN(CC1)CCC1CC1=CC=CC=C1 HNBRYFZSXNGYNV-UHFFFAOYSA-N 0.000 claims 1
- WLLKBLCWFWQMCU-UHFFFAOYSA-N 6-[3-(4-benzylpiperidin-1-yl)propanoyl]-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-2-one Chemical compound C=1C(=C23)CC(=O)N3CCCC2=CC=1C(=O)CCN(CC1)CCC1CC1=CC=CC=C1 WLLKBLCWFWQMCU-UHFFFAOYSA-N 0.000 claims 1
- DGDWINGZXYNWCR-UHFFFAOYSA-N 6-[3-[4-[(3-methylphenyl)methyl]piperazin-1-yl]propanoyl]-1-azatricyclo[6.3.1.04,12]dodeca-4,6,8(12)-trien-11-one Chemical compound CC1=CC=CC(CN2CCN(CCC(=O)C=3C=C4C=5N(C(CC4)=O)CCC=5C=3)CC2)=C1 DGDWINGZXYNWCR-UHFFFAOYSA-N 0.000 claims 1
- AYERPPFQRGBYLF-UHFFFAOYSA-N C1=CC(C)=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 Chemical compound C1=CC(C)=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 AYERPPFQRGBYLF-UHFFFAOYSA-N 0.000 claims 1
- BKDJCRHMVPTVKH-UHFFFAOYSA-N C1=CC(Cl)=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 Chemical compound C1=CC(Cl)=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 BKDJCRHMVPTVKH-UHFFFAOYSA-N 0.000 claims 1
- AYHIURKVNFVOOZ-UHFFFAOYSA-N C1=CC([N+](=O)[O-])=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1CCC(CCC(=O)C=2C=C3C=4N(C(CC3)=O)CCC=4C=2)CC1 AYHIURKVNFVOOZ-UHFFFAOYSA-N 0.000 claims 1
- JOGOEVMLWUAGQV-UHFFFAOYSA-N COC1=CC=CC(CN2CCC(CCC(=O)C=3C=C4C=5N(C(CC4)=O)CCC=5C=3)CC2)=C1 Chemical compound COC1=CC=CC(CN2CCC(CCC(=O)C=3C=C4C=5N(C(CC4)=O)CCC=5C=3)CC2)=C1 JOGOEVMLWUAGQV-UHFFFAOYSA-N 0.000 claims 1
- FPMBVWFIMIOUNX-UHFFFAOYSA-N ClC1=CC=CC(CN2CCN(CCC(=O)C=3C=C4C=5N(C(CC4)=O)CCC=5C=3)CC2)=C1 Chemical compound ClC1=CC=CC(CN2CCN(CCC(=O)C=3C=C4C=5N(C(CC4)=O)CCC=5C=3)CC2)=C1 FPMBVWFIMIOUNX-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 13
- 206010039966 Senile dementia Diseases 0.000 abstract description 10
- 230000000069 prophylactic effect Effects 0.000 abstract description 7
- 230000001225 therapeutic effect Effects 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 230000000407 monoamine reuptake Effects 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- 239000002904 solvent Substances 0.000 description 60
- 238000000034 method Methods 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 40
- 238000000921 elemental analysis Methods 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000013078 crystal Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000012458 free base Substances 0.000 description 9
- 235000011087 fumaric acid Nutrition 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
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- 239000001530 fumaric acid Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
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- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D225/08—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/18—[b, e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP553593 | 1993-01-18 | ||
| JP17328793 | 1993-07-13 | ||
| JP23967293 | 1993-09-27 | ||
| JP29982793 | 1993-11-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO940163D0 NO940163D0 (no) | 1994-01-17 |
| NO940163L NO940163L (no) | 1994-07-19 |
| NO300809B1 true NO300809B1 (no) | 1997-07-28 |
Family
ID=27454312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO940163A NO300809B1 (no) | 1993-01-18 | 1994-01-17 | Tricykliske kondenserte heterocykliske forbindelser og deres anvendelse |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5527800A (lt) |
| EP (1) | EP0607864B1 (lt) |
| KR (1) | KR940018384A (lt) |
| CN (1) | CN1104211A (lt) |
| AT (1) | ATE250031T1 (lt) |
| AU (1) | AU670981B2 (lt) |
| CA (1) | CA2113603C (lt) |
| DE (1) | DE69433148T2 (lt) |
| FI (1) | FI940229A (lt) |
| HU (1) | HUT66182A (lt) |
| NO (1) | NO300809B1 (lt) |
| NZ (1) | NZ250682A (lt) |
| TW (1) | TW248556B (lt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5620973A (en) * | 1993-11-30 | 1997-04-15 | Takeda Chemical Industries, Ltd. | Tetracyclic condensed heterocyclic compounds and their use |
| US5705501A (en) | 1994-11-17 | 1998-01-06 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-morpholinopropanones to treat Alzheimer's Disease |
| US5658909A (en) | 1994-11-17 | 1997-08-19 | Molecular Geriatrics Corporation | Certain substituted 1-aryl-3-piperazin-1'-yl propanones to treat Alzheimer's Disease |
| WO1998046590A1 (en) | 1997-04-17 | 1998-10-22 | Takeda Chemical Industries, Ltd. | Thermogenic composition and benzazepine thermogenics |
| GB9716879D0 (en) * | 1997-08-08 | 1997-10-15 | Shire Int Licensing Bv | Treatment of attention deficit disorders |
| US20020177593A1 (en) | 1998-09-30 | 2002-11-28 | Yuji Ishihara | Agents and crystals for improving excretory potency of urinary bladder |
| CN1163224C (zh) * | 1998-09-30 | 2004-08-25 | 武田药品工业株式会社 | 改善膀胱排泄能力的药物 |
| JP2003502332A (ja) * | 1999-06-14 | 2003-01-21 | ニューロゲン コーポレイション | １−アザ三環式−４−ベンジルピペラジン |
| DE19947297A1 (de) * | 1999-10-01 | 2001-04-19 | Morphochem Ag | Cyclische Biphenyle, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| AU2001277750A1 (en) * | 2000-08-10 | 2002-02-25 | Takeda Chemical Industries Ltd. | Use of polypeptide |
| KR20030032043A (ko) | 2000-09-21 | 2003-04-23 | 다케다 야쿠힌 고교 가부시키가이샤 | 3환식 축합 복소환 유도체의 제조 방법 |
| KR100614862B1 (ko) | 2001-12-28 | 2006-08-22 | 다케다 야쿠힌 고교 가부시키가이샤 | 배뇨 장애 예방제/치료제 |
| CA2531019A1 (en) * | 2003-06-30 | 2005-01-06 | Takeda Pharmaceutical Company Limited | Preventive/remedy for urinary disturbance |
| US20050143350A1 (en) * | 2003-11-19 | 2005-06-30 | Seed John C. | Combination drug therapy to treat obesity |
| CN102887880B (zh) * | 2012-08-20 | 2014-10-29 | 东南大学 | 二苯并呋喃衍生物及其制备方法与用途 |
| PL3641769T3 (pl) | 2017-06-20 | 2022-09-26 | Imbria Pharmaceuticals, Inc. | Pochodna 1-[(2,3,4-trimetoksyfenylo)metylo]piperazyny, jej kompozycje oraz sposoby zwiększania wydajności metabolizmu serca |
| US11780811B2 (en) | 2020-06-30 | 2023-10-10 | Imbria Pharmaceuticals, Inc. | Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
| US11530184B2 (en) | 2020-06-30 | 2022-12-20 | Imbria Pharmaceuticals, Inc. | Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
| US11883396B2 (en) | 2021-05-03 | 2024-01-30 | Imbria Pharmaceuticals, Inc. | Methods of treating kidney conditions using modified forms of trimetazidine |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3906007A (en) * | 1970-09-14 | 1975-09-16 | Richardson Merrell Inc | Bis-basic ketones of dibenzofuran |
| US4146624A (en) * | 1970-09-14 | 1979-03-27 | Richardson-Merrell Inc. | Method of treating viruses with bis-basic ketones of dibenzofuran |
| US3716539A (en) * | 1971-05-19 | 1973-02-13 | Aldrich Chem Co Inc | 1(2-dibenzofuryl)4-piperazino butanols |
| US4017621A (en) * | 1974-12-09 | 1977-04-12 | Sumitomo Chemical Company, Limited | 2-Morpholinyl tricyclic dibenzazepine compounds |
| DE2732750A1 (de) * | 1977-07-20 | 1979-02-08 | Merck Patent Gmbh | Basische thioaether und verfahren zu ihrer herstellung |
| EP0117233B1 (de) * | 1983-02-18 | 1987-08-26 | Ciba-Geigy Ag | Photohärtbare gefärbte Massen |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| CA2001338A1 (en) * | 1988-11-11 | 1990-05-11 | Ciba-Geigy Ag | Heterocyclic compounds |
| US5204340A (en) * | 1989-04-11 | 1993-04-20 | Eli Lilly And Company | Tetrahydrobenz(c,d)indole serotonin agonists |
| JP3054742B2 (ja) * | 1989-12-11 | 2000-06-19 | 武田薬品工業株式会社 | アミノナフタレン化合物 |
| TW197442B (lt) * | 1990-02-08 | 1993-01-01 | Pfizer | |
| US5302612A (en) * | 1990-02-26 | 1994-04-12 | Eli Lilly And Company | 6-substituted-hexahydrobenz[cd]indoles |
| TW219933B (lt) * | 1990-02-26 | 1994-02-01 | Lilly Co Eli | |
| TW197435B (lt) * | 1990-11-22 | 1993-01-01 | Takeda Pharm Industry Co Ltd | |
| US5364856A (en) * | 1991-03-28 | 1994-11-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles |
| US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
| US5106856A (en) * | 1991-06-07 | 1992-04-21 | Hoechst-Roussel Pharmaceuticals Inc. | [(Arylalkylpiperidin-4-yl)methyl]-2a,3,4,5-tetrahydro-1(2H)-acenaphthylen-1-ones and related compounds |
| US5202321A (en) * | 1991-06-13 | 1993-04-13 | Merck Frosst Canada, Inc. | Thiopyrano[2,3,4-c,d]indoles as inhibitors of leukotriene biosynthesis |
-
1993
- 1993-12-29 TW TW082111121A patent/TW248556B/zh active
-
1994
- 1994-01-13 EP EP94100403A patent/EP0607864B1/en not_active Expired - Lifetime
- 1994-01-13 AT AT94100403T patent/ATE250031T1/de not_active IP Right Cessation
- 1994-01-13 DE DE69433148T patent/DE69433148T2/de not_active Expired - Lifetime
- 1994-01-14 NZ NZ250682A patent/NZ250682A/en unknown
- 1994-01-17 HU HU9400132A patent/HUT66182A/hu unknown
- 1994-01-17 CA CA002113603A patent/CA2113603C/en not_active Expired - Fee Related
- 1994-01-17 FI FI940229A patent/FI940229A/fi not_active Application Discontinuation
- 1994-01-17 NO NO940163A patent/NO300809B1/no unknown
- 1994-01-17 CN CN94100503A patent/CN1104211A/zh active Pending
- 1994-01-18 AU AU53861/94A patent/AU670981B2/en not_active Ceased
- 1994-01-18 US US08/182,239 patent/US5527800A/en not_active Expired - Lifetime
- 1994-01-18 KR KR1019940000887A patent/KR940018384A/ko not_active Application Discontinuation
-
1996
- 1996-03-20 US US08/618,796 patent/US5686466A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1104211A (zh) | 1995-06-28 |
| AU5386194A (en) | 1994-07-21 |
| TW248556B (lt) | 1995-06-01 |
| NO940163D0 (no) | 1994-01-17 |
| DE69433148D1 (de) | 2003-10-23 |
| FI940229A0 (fi) | 1994-01-17 |
| CA2113603C (en) | 2006-11-28 |
| NO940163L (no) | 1994-07-19 |
| ATE250031T1 (de) | 2003-10-15 |
| AU670981B2 (en) | 1996-08-08 |
| HU9400132D0 (en) | 1994-05-30 |
| CA2113603A1 (en) | 1994-07-19 |
| EP0607864A2 (en) | 1994-07-27 |
| NZ250682A (en) | 1995-12-21 |
| EP0607864B1 (en) | 2003-09-17 |
| FI940229A (fi) | 1994-10-21 |
| KR940018384A (ko) | 1994-08-16 |
| HUT66182A (en) | 1994-09-28 |
| EP0607864A3 (en) | 1994-10-12 |
| US5527800A (en) | 1996-06-18 |
| DE69433148T2 (de) | 2004-06-03 |
| US5686466A (en) | 1997-11-11 |
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