JP2006517563A - 置換n−アリール複素環化合物、その製造方法およびその医薬としての使用 - Google Patents
置換n−アリール複素環化合物、その製造方法およびその医薬としての使用 Download PDFInfo
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- JP2006517563A JP2006517563A JP2006501827A JP2006501827A JP2006517563A JP 2006517563 A JP2006517563 A JP 2006517563A JP 2006501827 A JP2006501827 A JP 2006501827A JP 2006501827 A JP2006501827 A JP 2006501827A JP 2006517563 A JP2006517563 A JP 2006517563A
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- alkyl
- independently
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- aryl
- nitrogen atom
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000003814 drug Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title abstract description 275
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 399
- 229910052757 nitrogen Inorganic materials 0.000 claims description 231
- 229910052760 oxygen Inorganic materials 0.000 claims description 181
- -1 CF 3 Inorganic materials 0.000 claims description 179
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 171
- 229910052717 sulfur Inorganic materials 0.000 claims description 166
- 125000005842 heteroatom Chemical group 0.000 claims description 152
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 145
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 142
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 120
- 239000001301 oxygen Substances 0.000 claims description 120
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 117
- 239000011593 sulfur Substances 0.000 claims description 115
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 110
- 229910052801 chlorine Inorganic materials 0.000 claims description 109
- 229910052731 fluorine Inorganic materials 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 105
- 229910005965 SO 2 Inorganic materials 0.000 claims description 95
- 229910052799 carbon Inorganic materials 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 229910052794 bromium Inorganic materials 0.000 claims description 79
- 125000004043 oxo group Chemical group O=* 0.000 claims description 73
- 125000002619 bicyclic group Chemical group 0.000 claims description 65
- 125000002950 monocyclic group Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 11
- 208000008589 Obesity Diseases 0.000 claims description 8
- 239000005557 antagonist Substances 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 230000004580 weight loss Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 230000036541 health Effects 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- 230000027288 circadian rhythm Effects 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 description 294
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 279
- 239000000243 solution Substances 0.000 description 139
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
- 239000000460 chlorine Substances 0.000 description 67
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- 239000012074 organic phase Substances 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 238000002953 preparative HPLC Methods 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
- 235000019341 magnesium sulphate Nutrition 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 23
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 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 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 17
- 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 17
- 239000008346 aqueous phase Substances 0.000 description 16
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- 239000011541 reaction mixture Substances 0.000 description 15
- 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000000556 agonist Substances 0.000 description 14
- 150000002828 nitro derivatives Chemical class 0.000 description 14
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
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- VKQHTSSNSJIMAL-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1CCNCC1 VKQHTSSNSJIMAL-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 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 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
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- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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- 108090001061 Insulin Proteins 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- KOEKUQRWTOSZOR-UHFFFAOYSA-N n-methyl-n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)N(C)C1CCNC1 KOEKUQRWTOSZOR-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- KRTYTCIYWFIVCY-UHFFFAOYSA-N n-[4-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1C(N(C)C)CCN1C(C=C1)=CC=C1NC(=O)C1=CC=C(O)N=C1 KRTYTCIYWFIVCY-UHFFFAOYSA-N 0.000 description 5
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- HXRJOCKYTOGLAA-UHFFFAOYSA-N tert-butyl n-[[1-[5-[(4-cyclohexylbenzoyl)amino]pyridin-2-yl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C(N=C1)=CC=C1NC(=O)C1=CC=C(C2CCCCC2)C=C1 HXRJOCKYTOGLAA-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 4
- AYIXGVABNMIOLK-UHFFFAOYSA-N 1-methylpiperidin-1-ium-3-carboxylate Chemical compound CN1CCCC(C(O)=O)C1 AYIXGVABNMIOLK-UHFFFAOYSA-N 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
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- 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
- VQAYPSYNIOCISE-UHFFFAOYSA-N tert-butyl n-[[1-[4-[(5-bromofuran-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(Br)O1 VQAYPSYNIOCISE-UHFFFAOYSA-N 0.000 description 1
- MGZPAHBKKJNVEN-UHFFFAOYSA-N tert-butyl n-[[1-[5-[(4-cyclohexylbenzoyl)-(3-methylbut-2-enyl)amino]pyridin-2-yl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C=1C=C(N2CC(CNC(=O)OC(C)(C)C)CC2)N=CC=1N(CC=C(C)C)C(=O)C(C=C1)=CC=C1C1CCCCC1 MGZPAHBKKJNVEN-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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229960004605 timolol 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
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Substances FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 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
- 229960001722 verapamil Drugs 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
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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
- 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
- C07D207/04—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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- 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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- 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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- 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
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- C—CHEMISTRY; METALLURGY
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- 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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- 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
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- 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
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- 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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- 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
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- 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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- 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
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- Pyrrole Compounds (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| 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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| JP2006517563A true JP2006517563A (ja) | 2006-07-27 |
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Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005016910A1 (ja) * | 2003-08-18 | 2006-10-12 | 富士フイルムファインケミカルズ株式会社 | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類とそれらの製造方法 |
| JP2006528643A (ja) * | 2003-07-24 | 2006-12-21 | ユーロ−セルティーク エス.エイ. | 疼痛治療または予防に有用な4−ヘテロアリール−テトラヒドロピペリジル化合物 |
| JP2007520466A (ja) * | 2003-12-23 | 2007-07-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 摂食障害を治療するためのmchアンタゴニスト(メラニン含有ホルモン)の形態で使用される3−(4−ピペリジン−1−イルメチル−フェニル)−プロピオン酸−フェニルアミド誘導体及び関連化合物 |
| WO2008153182A1 (ja) * | 2007-06-15 | 2008-12-18 | Mitsubishi Tanabe Pharma Corporation | モルホリン誘導体 |
| WO2010038803A1 (ja) * | 2008-09-30 | 2010-04-08 | 持田製薬株式会社 | 2-インドールアクリルアミド類縁体 |
| WO2010101247A1 (ja) * | 2009-03-05 | 2010-09-10 | 塩野義製薬株式会社 | Npy y5受容体拮抗作用を有するシクロヘキサン誘導体 |
| WO2010101246A1 (ja) * | 2009-03-05 | 2010-09-10 | 塩野義製薬株式会社 | Npy y5受容体拮抗作用を有するピペリジンおよびピロリジン誘導体 |
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- 2004-02-13 PL PL378065A patent/PL378065A1/pl not_active Application Discontinuation
- 2004-02-13 PE PE2004000158A patent/PE20040952A1/es not_active Application Discontinuation
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- 2004-02-13 JP JP2006501827A patent/JP2006517563A/ja active Pending
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| JP5685181B2 (ja) * | 2009-03-05 | 2015-03-18 | 塩野義製薬株式会社 | Npyy5受容体拮抗作用を有するシクロヘキサン誘導体 |
| WO2010101247A1 (ja) * | 2009-03-05 | 2010-09-10 | 塩野義製薬株式会社 | Npy y5受容体拮抗作用を有するシクロヘキサン誘導体 |
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| JP2016504276A (ja) * | 2012-11-05 | 2016-02-12 | ナント ホールディングス アイピー,エルエルシー | ヘッジホッグシグナル伝達経路阻害剤としての環状スルホンアミド含有誘導体 |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN100506792C (zh) | 2009-07-01 |
| NO20054220L (no) | 2005-10-28 |
| KR20050101215A (ko) | 2005-10-20 |
| UA86760C2 (ru) | 2009-05-25 |
| MA27735A1 (fr) | 2006-02-01 |
| CN1774418A (zh) | 2006-05-17 |
| EP1597228A2 (de) | 2005-11-23 |
| WO2004072025A3 (de) | 2004-12-23 |
| TNSN05194A1 (en) | 2007-06-11 |
| ZA200506369B (en) | 2006-07-26 |
| AU2004212145B2 (en) | 2010-06-17 |
| MXPA05008449A (es) | 2006-05-25 |
| AR044496A1 (es) | 2005-09-14 |
| MY139102A (en) | 2009-08-28 |
| RU2005128551A (ru) | 2006-02-10 |
| PL378065A1 (pl) | 2006-02-20 |
| BRPI0407504A (pt) | 2006-02-14 |
| ECSP055967A (es) | 2006-01-16 |
| RS20050666A (sr) | 2007-12-31 |
| TW200510297A (en) | 2005-03-16 |
| NZ541823A (en) | 2009-01-31 |
| PA8595901A1 (es) | 2004-09-16 |
| UY28186A1 (es) | 2004-09-30 |
| NO20054220D0 (no) | 2005-09-12 |
| DE10306250A1 (de) | 2004-09-09 |
| OA13027A (en) | 2006-11-10 |
| HRP20050710A2 (en) | 2006-07-31 |
| WO2004072025A2 (de) | 2004-08-26 |
| PE20040952A1 (es) | 2005-02-08 |
| CO5690548A2 (es) | 2006-10-31 |
| AU2004212145A1 (en) | 2004-08-26 |
| CA2516118A1 (en) | 2004-08-26 |
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