AU2004212145B2 - Substituted N-arylheterocycles, method for production and use thereof as medicaments - Google Patents
Substituted N-arylheterocycles, method for production and use thereof as medicaments Download PDFInfo
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- AU2004212145B2 AU2004212145B2 AU2004212145A AU2004212145A AU2004212145B2 AU 2004212145 B2 AU2004212145 B2 AU 2004212145B2 AU 2004212145 A AU2004212145 A AU 2004212145A AU 2004212145 A AU2004212145 A AU 2004212145A AU 2004212145 B2 AU2004212145 B2 AU 2004212145B2
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- Australia
- Prior art keywords
- alkyl
- independently
- another
- group
- nitrogen atom
- Prior art date
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- 239000003814 drug Substances 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 302
- 238000000034 method Methods 0.000 claims description 290
- 229910052757 nitrogen Inorganic materials 0.000 claims description 200
- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000005842 heteroatom Chemical group 0.000 claims description 124
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 120
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 116
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 115
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 104
- 229910052760 oxygen Inorganic materials 0.000 claims description 104
- -1 (C-C2)-alkylene-aryl Chemical group 0.000 claims description 99
- 229910052717 sulfur Inorganic materials 0.000 claims description 96
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 94
- 239000001301 oxygen Substances 0.000 claims description 94
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 90
- 239000011593 sulfur Substances 0.000 claims description 90
- 229910052731 fluorine Inorganic materials 0.000 claims description 87
- 229910052801 chlorine Inorganic materials 0.000 claims description 83
- 229910052799 carbon Inorganic materials 0.000 claims description 65
- 125000004043 oxo group Chemical group O=* 0.000 claims description 63
- 229910052794 bromium Inorganic materials 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 239000004480 active ingredient Substances 0.000 claims description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 125000002950 monocyclic group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 230000001539 anorectic effect Effects 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 239000013585 weight reducing agent Substances 0.000 claims description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims description 3
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 230000027288 circadian rhythm Effects 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims 2
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 239000000047 product Substances 0.000 description 296
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
- 239000000243 solution Substances 0.000 description 149
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
- 239000000460 chlorine Substances 0.000 description 127
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
- 239000012074 organic phase Substances 0.000 description 58
- 238000002953 preparative HPLC Methods 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 229910052938 sodium sulfate Inorganic materials 0.000 description 38
- 235000011152 sodium sulphate Nutrition 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 32
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
- 235000019341 magnesium sulphate Nutrition 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 21
- 238000004587 chromatography analysis Methods 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 18
- DIOJDWCYVGKRHV-UHFFFAOYSA-N n-[1-(4-aminophenyl)pyrrolidin-3-yl]-n-methylacetamide Chemical compound C1C(N(C)C(C)=O)CCN1C1=CC=C(N)C=C1 DIOJDWCYVGKRHV-UHFFFAOYSA-N 0.000 description 18
- 235000011181 potassium carbonates Nutrition 0.000 description 18
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 17
- 239000000556 agonist Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- XYKYUXYNQDXZTD-UHFFFAOYSA-N tert-butyl n-methyl-n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1CCNC1 XYKYUXYNQDXZTD-UHFFFAOYSA-N 0.000 description 15
- PZJDWCYGPDQBKO-UHFFFAOYSA-N 1-(4-aminophenyl)-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1C1=CC=C(N)C=C1 PZJDWCYGPDQBKO-UHFFFAOYSA-N 0.000 description 14
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 14
- 150000002828 nitro derivatives Chemical class 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- VKQHTSSNSJIMAL-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1CCNCC1 VKQHTSSNSJIMAL-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- CCCAHLCWKFZPSO-UHFFFAOYSA-N 1-(4-cyclopentyloxyphenyl)-3-[4-[3-(methylamino)pyrrolidin-1-yl]phenyl]urea Chemical compound C1C(NC)CCN1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OC1CCCC1 CCCAHLCWKFZPSO-UHFFFAOYSA-N 0.000 description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 102000004877 Insulin Human genes 0.000 description 9
- 108090001061 Insulin Proteins 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 125000005275 alkylenearyl group Chemical group 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229940125396 insulin Drugs 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 description 7
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 7
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- WGZXDJLTJVSHDW-UHFFFAOYSA-N n-[4-(3-bromo-2-oxopyrrolidin-1-yl)phenyl]-4-cyclohexyl-n-methylbenzamide Chemical compound C=1C=C(N2C(C(Br)CC2)=O)C=CC=1N(C)C(=O)C(C=C1)=CC=C1C1CCCCC1 WGZXDJLTJVSHDW-UHFFFAOYSA-N 0.000 description 7
- KOEKUQRWTOSZOR-UHFFFAOYSA-N n-methyl-n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)N(C)C1CCNC1 KOEKUQRWTOSZOR-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HKTRNIXRNCIIMB-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]piperidine-4-carboxamide Chemical compound C1C(N(C)C)CCN1C(C=C1)=CC=C1NC(=O)C1CCNCC1 HKTRNIXRNCIIMB-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- AYIXGVABNMIOLK-UHFFFAOYSA-N 1-methylpiperidin-1-ium-3-carboxylate Chemical compound CN1CCCC(C(O)=O)C1 AYIXGVABNMIOLK-UHFFFAOYSA-N 0.000 description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- MJYXKFGXJBLJAW-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCC1C1=CC=C(Cl)C=C1 MJYXKFGXJBLJAW-UHFFFAOYSA-N 0.000 description 5
- BYQMUVAEWOWYTC-UHFFFAOYSA-N 4-cyclopentyloxyaniline Chemical compound C1=CC(N)=CC=C1OC1CCCC1 BYQMUVAEWOWYTC-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
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- MHKGICANFKTBAG-UHFFFAOYSA-N tert-butyl N-[1-(5-aminopyridin-2-yl)pyrrolidin-3-yl]carbamate 2-chloro-5-nitropyridine Chemical compound ClC1=NC=C(C=C1)[N+](=O)[O-].NC=1C=CC(=NC1)N1CC(CC1)NC(OC(C)(C)C)=O MHKGICANFKTBAG-UHFFFAOYSA-N 0.000 description 1
- VKKPVXWPHKXMGT-RFVHGSKJSA-N tert-butyl N-[[(3R)-1-(4-amino-3-fluorophenyl)pyrrolidin-3-yl]methyl]carbamate 2,4-difluoro-1-nitrobenzene Chemical compound FC1=C(C=CC(=C1)F)[N+](=O)[O-].NC1=C(C=C(C=C1)N1C[C@H](CC1)CNC(OC(C)(C)C)=O)F VKKPVXWPHKXMGT-RFVHGSKJSA-N 0.000 description 1
- AWAQIBUAFLLFCC-UHFFFAOYSA-N tert-butyl N-[[1-(4-amino-2,5-difluorophenyl)pyrrolidin-3-yl]methyl]carbamate 1,2,4-trifluoro-5-nitrobenzene Chemical compound FC=1C=C(C(=CC1F)F)[N+](=O)[O-].NC1=CC(=C(C=C1F)N1CC(CC1)CNC(OC(C)(C)C)=O)F AWAQIBUAFLLFCC-UHFFFAOYSA-N 0.000 description 1
- ZZQPDIHOUAJKKV-UHFFFAOYSA-N tert-butyl N-[[1-(4-amino-2,6-difluorophenyl)pyrrolidin-3-yl]methyl]carbamate 1,2,3-trifluoro-5-nitrobenzene Chemical compound FC=1C=C(C=C(C1F)F)[N+](=O)[O-].NC1=CC(=C(C(=C1)F)N1CC(CC1)CNC(OC(C)(C)C)=O)F ZZQPDIHOUAJKKV-UHFFFAOYSA-N 0.000 description 1
- MBZHVGLOGXKURO-UHFFFAOYSA-N tert-butyl N-[[1-(4-amino-3-cyanophenyl)pyrrolidin-3-yl]methyl]carbamate 5-fluoro-2-nitrobenzonitrile Chemical compound C(#N)C1=C(C=CC(=C1)F)[N+](=O)[O-].NC1=C(C=C(C=C1)N1CC(CC1)CNC(OC(C)(C)C)=O)C#N MBZHVGLOGXKURO-UHFFFAOYSA-N 0.000 description 1
- ALMPOBXZTFKPJY-UHFFFAOYSA-N tert-butyl N-[[1-(4-aminophenyl)azetidin-3-yl]methyl]carbamate tert-butyl N-methyl-N-[1-(4-nitrophenyl)azetidin-3-yl]carbamate Chemical compound CN(C(OC(C)(C)C)=O)C1CN(C1)C1=CC=C(C=C1)[N+](=O)[O-].NC1=CC=C(C=C1)N1CC(C1)CNC(OC(C)(C)C)=O ALMPOBXZTFKPJY-UHFFFAOYSA-N 0.000 description 1
- OWUIRMOFVLGQOJ-UHFFFAOYSA-N tert-butyl N-[[1-(5-amino-6-chloropyridin-2-yl)pyrrolidin-3-yl]methyl]carbamate 2-chloro-6-fluoro-3-nitropyridine Chemical compound ClC1=NC(=CC=C1[N+](=O)[O-])F.NC=1C=CC(=NC1Cl)N1CC(CC1)CNC(OC(C)(C)C)=O OWUIRMOFVLGQOJ-UHFFFAOYSA-N 0.000 description 1
- OIKGWMZUKQHQAJ-ITMPLDIFSA-N tert-butyl N-methyl-N-[(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate tert-butyl N-[(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N1C[C@@H](CC1)NC(OC(C)(C)C)=O.CN(C(OC(C)(C)C)=O)[C@H]1CN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] OIKGWMZUKQHQAJ-ITMPLDIFSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical class CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- JEMODJPTQZUWFU-UHFFFAOYSA-N tert-butyl n-[1-(4-nitrophenyl)azetidin-3-yl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)CN1C1=CC=C([N+]([O-])=O)C=C1 JEMODJPTQZUWFU-UHFFFAOYSA-N 0.000 description 1
- FLHFCURTZVMLFH-UHFFFAOYSA-N tert-butyl n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridin-1-yl]carbamate Chemical compound C1N(NC(=O)OC(C)(C)C)CCC(B2OC(C)(C)C(C)(C)O2)=C1 FLHFCURTZVMLFH-UHFFFAOYSA-N 0.000 description 1
- SLNNRLJNFLCYIB-UHFFFAOYSA-N tert-butyl n-[4-(5-chloropyridin-2-yl)-3,6-dihydro-2h-pyridin-1-yl]carbamate Chemical compound C1N(NC(=O)OC(C)(C)C)CCC(C=2N=CC(Cl)=CC=2)=C1 SLNNRLJNFLCYIB-UHFFFAOYSA-N 0.000 description 1
- UOLHUTWQUUCUFA-CQSZACIVSA-N tert-butyl n-[[(3r)-1-[2-fluoro-4-(propan-2-ylamino)phenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound FC1=CC(NC(C)C)=CC=C1N1C[C@@H](CNC(=O)OC(C)(C)C)CC1 UOLHUTWQUUCUFA-CQSZACIVSA-N 0.000 description 1
- HCEWERNNDJMPHB-CQSZACIVSA-N tert-butyl n-[[(3r)-1-[4-(cyclobutylamino)-2-fluorophenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1[C@@H](CNC(=O)OC(C)(C)C)CCN1C(C(=C1)F)=CC=C1NC1CCC1 HCEWERNNDJMPHB-CQSZACIVSA-N 0.000 description 1
- BCWSGUXZQQNQFQ-LJQANCHMSA-N tert-butyl n-[[(3r)-1-[5-[[4-(4-chlorophenyl)piperidine-1-carbonyl]amino]pyridin-2-yl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1[C@@H](CNC(=O)OC(C)(C)C)CCN1C(N=C1)=CC=C1NC(=O)N1CCC(C=2C=CC(Cl)=CC=2)CC1 BCWSGUXZQQNQFQ-LJQANCHMSA-N 0.000 description 1
- CUERVYCBXCAYLZ-UHFFFAOYSA-N tert-butyl n-[[1-(4-amino-2,3-difluorophenyl)pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=CC=C(N)C(F)=C1F CUERVYCBXCAYLZ-UHFFFAOYSA-N 0.000 description 1
- JDCHMTPZEICJAY-UHFFFAOYSA-N tert-butyl n-[[1-(4-amino-2-chlorophenyl)pyrrolidin-3-yl]methyl]carbamate;2-chloro-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(Cl)=C1.C1C(CNC(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1Cl JDCHMTPZEICJAY-UHFFFAOYSA-N 0.000 description 1
- RLWUTHBFGDCDFH-UHFFFAOYSA-N tert-butyl n-[[1-(4-amino-3-fluorophenyl)pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=CC=C(N)C(F)=C1 RLWUTHBFGDCDFH-UHFFFAOYSA-N 0.000 description 1
- HURVICYATQFIPU-UHFFFAOYSA-N tert-butyl n-[[1-(4-aminonaphthalen-1-yl)pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=CC=C(N)C2=CC=CC=C12 HURVICYATQFIPU-UHFFFAOYSA-N 0.000 description 1
- FMYDXRUPDOUOIQ-UHFFFAOYSA-N tert-butyl n-[[1-(4-aminophenyl)azetidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CN1C1=CC=C(N)C=C1 FMYDXRUPDOUOIQ-UHFFFAOYSA-N 0.000 description 1
- VKLVOVFPERHDFZ-UHFFFAOYSA-N tert-butyl n-[[1-[4-[(2-amino-4-butoxybenzoyl)amino]-3-fluorophenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound NC1=CC(OCCCC)=CC=C1C(=O)NC1=CC=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C=C1F VKLVOVFPERHDFZ-UHFFFAOYSA-N 0.000 description 1
- XIWLLBVPWNELRB-UHFFFAOYSA-N tert-butyl n-[[1-[4-[[5-(2-fluorophenyl)furan-2-carbonyl]amino]phenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C(=CC=CC=2)F)O1 XIWLLBVPWNELRB-UHFFFAOYSA-N 0.000 description 1
- YXJNYTPDQVIZDW-UHFFFAOYSA-N tert-butyl n-methyl-n-[1-(4-nitrophenyl)azetidin-3-yl]carbamate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CN1C1=CC=C([N+]([O-])=O)C=C1 YXJNYTPDQVIZDW-UHFFFAOYSA-N 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 229950004437 tiqueside Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229960001130 urapidil Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- 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
- C07D211/36—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 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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DE10306250.5 | 2003-02-14 | ||
DE10306250A DE10306250A1 (de) | 2003-02-14 | 2003-02-14 | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
PCT/EP2004/001342 WO2004072025A2 (de) | 2003-02-14 | 2004-02-13 | Substituierte n-arylheterozyklen, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
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2004
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- 2004-02-13 WO PCT/EP2004/001342 patent/WO2004072025A2/de active Search and Examination
- 2004-02-13 KR KR1020057014989A patent/KR20050101215A/ko not_active Application Discontinuation
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- 2004-02-13 CN CNB2004800098606A patent/CN100506792C/zh not_active Expired - Fee Related
- 2004-02-13 UY UY28186A patent/UY28186A1/es unknown
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- 2004-02-13 EP EP04710808A patent/EP1597228A2/de not_active Withdrawn
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- 2004-02-13 AU AU2004212145A patent/AU2004212145B2/en not_active Ceased
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- 2005-08-11 CO CO05079788A patent/CO5690548A2/es not_active Application Discontinuation
- 2005-08-12 HR HR20050710A patent/HRP20050710A2/xx not_active Application Discontinuation
- 2005-08-12 TN TNP2005000194A patent/TNSN05194A1/en unknown
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NO20054220D0 (no) | 2005-09-12 |
WO2004072025A2 (de) | 2004-08-26 |
JP2006517563A (ja) | 2006-07-27 |
TW200510297A (en) | 2005-03-16 |
PE20040952A1 (es) | 2005-02-08 |
CA2516118A1 (en) | 2004-08-26 |
MY139102A (en) | 2009-08-28 |
PA8595901A1 (es) | 2004-09-16 |
MA27735A1 (fr) | 2006-02-01 |
CN100506792C (zh) | 2009-07-01 |
OA13027A (en) | 2006-11-10 |
WO2004072025A3 (de) | 2004-12-23 |
UY28186A1 (es) | 2004-09-30 |
AR044496A1 (es) | 2005-09-14 |
NO20054220L (no) | 2005-10-28 |
UA86760C2 (ru) | 2009-05-25 |
RU2005128551A (ru) | 2006-02-10 |
RS20050666A (en) | 2007-12-31 |
BRPI0407504A (pt) | 2006-02-14 |
ECSP055967A (es) | 2006-01-16 |
CN1774418A (zh) | 2006-05-17 |
DE10306250A1 (de) | 2004-09-09 |
ZA200506369B (en) | 2006-07-26 |
EP1597228A2 (de) | 2005-11-23 |
TNSN05194A1 (en) | 2007-06-11 |
CO5690548A2 (es) | 2006-10-31 |
NZ541823A (en) | 2009-01-31 |
KR20050101215A (ko) | 2005-10-20 |
AU2004212145A1 (en) | 2004-08-26 |
HRP20050710A2 (en) | 2006-07-31 |
MXPA05008449A (es) | 2006-05-25 |
PL378065A1 (pl) | 2006-02-20 |
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