MXPA05008449A - N-arilheterociclos sustituidos, procedimientos para su preparacion, y su empleo como medicamentos. - Google Patents
N-arilheterociclos sustituidos, procedimientos para su preparacion, y su empleo como medicamentos.Info
- Publication number
- MXPA05008449A MXPA05008449A MXPA05008449A MXPA05008449A MXPA05008449A MX PA05008449 A MXPA05008449 A MX PA05008449A MX PA05008449 A MXPA05008449 A MX PA05008449A MX PA05008449 A MXPA05008449 A MX PA05008449A MX PA05008449 A MXPA05008449 A MX PA05008449A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- phenyl
- independently
- mean
- pyrrolidin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000003814 drug Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 claims abstract description 265
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 9
- 230000001539 anorectic effect Effects 0.000 claims abstract description 8
- -1 0- (Ci-C8 alkyl) Chemical group 0.000 claims description 360
- 125000000217 alkyl group Chemical group 0.000 claims description 349
- 229910052757 nitrogen Inorganic materials 0.000 claims description 183
- 125000005842 heteroatom Chemical group 0.000 claims description 123
- 229910052760 oxygen Inorganic materials 0.000 claims description 121
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 116
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 111
- 229910052717 sulfur Inorganic materials 0.000 claims description 108
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 94
- 229910052731 fluorine Inorganic materials 0.000 claims description 93
- 229910052801 chlorine Inorganic materials 0.000 claims description 90
- 239000001301 oxygen Substances 0.000 claims description 88
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- 125000002947 alkylene group Chemical group 0.000 claims description 79
- 239000011593 sulfur Substances 0.000 claims description 74
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 66
- 229910052794 bromium Inorganic materials 0.000 claims description 64
- 125000004043 oxo group Chemical group O=* 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
- 125000002619 bicyclic group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 17
- 229910052720 vanadium Inorganic materials 0.000 claims description 15
- 125000004354 sulfur functional group Chemical group 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims description 8
- 239000005557 antagonist Substances 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000013585 weight reducing agent Substances 0.000 claims description 3
- 230000027288 circadian rhythm Effects 0.000 claims description 2
- 230000008447 perception Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 239000004081 narcotic agent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 295
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 278
- 239000000243 solution Substances 0.000 description 151
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 143
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- 239000000460 chlorine Substances 0.000 description 79
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- 239000002253 acid Substances 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
- 239000012074 organic phase Substances 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 47
- 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 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000002953 preparative HPLC Methods 0.000 description 40
- 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 38
- 235000011152 sodium sulphate Nutrition 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 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 23
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 21
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- 238000004587 chromatography analysis Methods 0.000 description 20
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 19
- 125000004356 hydroxy functional group Chemical group O* 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
- 150000002148 esters Chemical class 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000556 agonist Substances 0.000 description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000000392 cycloalkenyl group Chemical group 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229960004132 diethyl ether Drugs 0.000 description 11
- 150000002828 nitro derivatives Chemical class 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- VKQHTSSNSJIMAL-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1CCNCC1 VKQHTSSNSJIMAL-UHFFFAOYSA-N 0.000 description 8
- 102000004877 Insulin Human genes 0.000 description 8
- 108090001061 Insulin Proteins 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000001412 amines Chemical class 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
- 229940125396 insulin Drugs 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- 125000006414 CCl Chemical group ClC* 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
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 6
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 5
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-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
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 5
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
- 229960001693 terazosin Drugs 0.000 description 1
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 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
- CGPHGPCHVUSFFA-LLVKDONJSA-N tosyl-d-proline Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1[C@@H](C(O)=O)CCC1 CGPHGPCHVUSFFA-LLVKDONJSA-N 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
- 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
- 229960001722 verapamil Drugs 0.000 description 1
- 235000012431 wafers Nutrition 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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- 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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- 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
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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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- 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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- 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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- 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
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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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- C—CHEMISTRY; METALLURGY
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- 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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- 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
- C07D413/12—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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- Chemical & Material Sciences (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05008449A true MXPA05008449A (es) | 2006-05-25 |
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| MXPA05008449A MXPA05008449A (es) | 2003-02-14 | 2004-02-13 | N-arilheterociclos sustituidos, procedimientos para su preparacion, y su empleo como medicamentos. |
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| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| ATE534649T1 (de) | 2003-05-15 | 2011-12-15 | Arqule Inc | Imidazothiazole und imidazoxazolderivative als inhibitoren von p38 |
| ES2327684T3 (es) * | 2003-07-24 | 2009-11-02 | Euro-Celtique S.A. | Compuestos heteroaril-tetrahidropiridilo utiles para el tratamiento o la prevencion del dolor. |
| PL1867644T3 (pl) * | 2003-07-24 | 2009-10-30 | Euro Celtique Sa | Związki heteroarylo-tetrahydropiperydylowe przydatne w leczeniu lub zapobieganiu bólu |
| EP2426120A1 (en) * | 2003-08-18 | 2012-03-07 | Fujifilm Finechemicals Co., Ltd. | Pyridyltetrahydropyridines and pyridylpiperidines, and method of manufacturing them |
| DE10360745A1 (de) * | 2003-12-23 | 2005-07-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| US7319108B2 (en) | 2004-01-25 | 2008-01-15 | Sanofi-Aventis Deutschland Gmbh | Aryl-substituted heterocycles, process for their preparation and their use as medicaments |
| DE102004003812A1 (de) * | 2004-01-25 | 2005-08-11 | Aventis Pharma Deutschland Gmbh | Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7829560B2 (en) | 2004-07-08 | 2010-11-09 | Arqule, Inc. | 1,4-disubstituted naphthalenes as inhibitors of P38 MAP kinase |
| WO2006022442A1 (ja) * | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体 |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| TW200626138A (en) * | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| CA2582327A1 (en) * | 2004-10-01 | 2006-04-13 | Takao Suzuki | 2-arylcarboxamide-nitrogeneous heterocycle compound |
| BRPI0516602A (pt) * | 2004-10-18 | 2008-09-16 | Lilly Co Eli | composto, e, composição farmacêutica |
| EP2258704A1 (en) | 2004-10-19 | 2010-12-08 | ArQule, Inc. | Synthesis of imidazooxazole and imidazothiazole inhibitors of p38 map kinase |
| DE102004051277A1 (de) * | 2004-10-21 | 2006-04-27 | Merck Patent Gmbh | Heterocyclische Carbonylverbindungen |
| US8084492B2 (en) * | 2004-11-19 | 2011-12-27 | The New Industry Research Organization | Benzofuran compound and pharmaceutical composition containing the same |
| BRPI0519343A2 (pt) | 2004-12-30 | 2009-01-20 | Janssen Pharmaceutica Nv | piperazinil e piperidinil urÉias e compostos relacionados como moduladores de hidrolase de amida de Ácido graxo para o tratamento de ansiedade, dor e outras condiÇÕes |
| TWI444187B (zh) * | 2005-01-25 | 2014-07-11 | Synta Pharmaceuticals Corp | 用於炎症及免疫相關用途之噻吩化合物 |
| ES2322965T3 (es) | 2005-09-30 | 2009-07-02 | F. Hoffmann-La Roche Ag | Derivados de indano como antagonistas de receptores de mch. |
| CA2641744C (en) | 2006-02-10 | 2012-09-25 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as aurora kinase inhibitors |
| CA2636605A1 (en) * | 2006-02-15 | 2007-08-23 | Lothar Schwink | Novel azacycly-substituted arylthienopyrimidinones, process for their preparation and their use as medicaments |
| JP2009526794A (ja) * | 2006-02-15 | 2009-07-23 | サノフィ−アベンティス | 新規なアミノアルコール置換アリールチエノピリミジノン、それらの製造方法及び薬剤としてそれらの使用 |
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| CN101426774B (zh) * | 2006-04-19 | 2012-04-25 | 安斯泰来制药有限公司 | 唑类甲酰胺衍生物 |
| RS56600B1 (sr) | 2006-04-19 | 2018-02-28 | Novartis Ag | 6-o-supstituisana jedinjenja benzoksazola i benzotiazola i postupci inhibicije csf-1r signalinga |
| UA93548C2 (uk) | 2006-05-05 | 2011-02-25 | Айерем Елелсі | Сполуки та композиції як модулятори хеджхогівського сигнального шляху |
| AU2007249924B2 (en) | 2006-05-08 | 2013-07-04 | Ariad Pharmaceuticals, Inc. | Acetylenic heteroaryl compounds |
| EA200870515A1 (ru) | 2006-05-08 | 2009-06-30 | Ариад Фармасьютикалз, Инк. | Моноциклические гетероарильные соединения |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| MX2009002019A (es) | 2006-08-24 | 2009-03-09 | Novartis Ag | Derivados de 2-(pirazin-2-il)-tiazol y 2-(1h-pirazol-3-il)-tiazol asi como compuestos relacionados como inhibidores de la estearoil-coa-desaturasa (scd) para el tratamiento de trastornos metabolicos, cardiovasculares, y otros. |
| EA200970266A1 (ru) | 2006-09-11 | 2009-08-28 | Глэксо Груп Лимитед | Азабициклические соединения в качестве ингибиторов повторного поглощения моноаминов |
| JP2010504362A (ja) * | 2006-09-25 | 2010-02-12 | アレテ セラピューティクス, インコーポレイテッド | 可溶性エポキシドヒドロラーゼ阻害剤 |
| PE20080888A1 (es) * | 2006-10-18 | 2008-08-26 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE LA ACIL-TRANSFERASA DE ACIL-CoA-DIACIL-GLICEROL 1 (DGAT1) |
| EP2118069B1 (en) * | 2007-01-09 | 2014-01-01 | Amgen Inc. | Bis-aryl amide derivatives useful for the treatment of cancer |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| GB0706793D0 (en) * | 2007-04-05 | 2007-05-16 | Evotec Ag | Compounds |
| WO2008148851A1 (en) | 2007-06-08 | 2008-12-11 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| PA8783601A1 (es) * | 2007-06-08 | 2009-01-23 | Janssen Pharmaceutica Nv | Derivados de piperidina/piperazina |
| WO2008148840A1 (en) | 2007-06-08 | 2008-12-11 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| TWI452044B (zh) | 2007-06-15 | 2014-09-11 | Mitsubishi Tanabe Pharma Corp | 嗎啉衍生物 |
| TW200918521A (en) * | 2007-08-31 | 2009-05-01 | Astrazeneca Ab | Heterocyclic amides and methods of use thereof |
| US8722894B2 (en) | 2007-09-14 | 2014-05-13 | Janssen Pharmaceuticals, Inc. | 1,3-disubstituted-4-phenyl-1H-pyridin-2-ones |
| NZ584152A (en) | 2007-09-14 | 2011-11-25 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| SI2203439T1 (sl) | 2007-09-14 | 2011-05-31 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituirani 4-fenil-3,4,5,6-tetrahidro-2H-1'H-(1,4')bipiridinil-2'-oni |
| AU2008312636B2 (en) * | 2007-10-17 | 2013-03-14 | Sanofi-Aventis | Substituted N-phenyl-pyrrolidinylmethylpyrrolidine amides and therapeutic use thereof as histamine H3 receptor modulators |
| SI2215058T1 (sl) * | 2007-10-17 | 2012-03-30 | Sanofi Sa | Substituirane N fenil bipirolidin sečnine in njihova terapevtska uporaba |
| BRPI0818626A2 (pt) * | 2007-10-17 | 2015-09-29 | Sanofi Aventis | n-fenil-bipirrolidina carboxamidas substituída e uso terapêutico da mesma |
| SI2212283T1 (sl) * | 2007-10-17 | 2011-12-30 | Sanofi Sa | Substituirani n-fenil-bipirolidin karboksamidi in njihova terapevtska uporaba |
| US8304547B2 (en) | 2007-10-24 | 2012-11-06 | Astellas Pharma Inc. | Azolecarboxamide compound or salt thereof |
| RU2492170C9 (ru) | 2007-11-14 | 2013-12-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2 |
| EP2070916A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | 2-Aryl-thiazol-4-carbonsäureamid-Derivate, deren Herstellung und Verwendung als Arzneimittel |
| EP2070925A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Neue 2-substituierte Tiazol-4-carbonsäureamid-Derivative deren Herstellung und Verwendung als Arzneimittel |
| EP2070924A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Neue 2-Hetarylthiazol-4-carbonsäureamid-Derivative, deren Herstellung und Verwendung als Arzneimittel |
| RU2364597C1 (ru) * | 2007-12-14 | 2009-08-20 | Андрей Александрович Иващенко | ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ Hh-СИГНАЛЬНОГО КАСКАДА, ЛЕКАРСТВЕННЫЕ КОМПОЗИЦИИ НА ИХ ОСНОВЕ И СПОСОБ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С АББЕРАНТНОЙ АКТИВНОСТЬЮ Hh СИГНАЛЬНОЙ СИСТЕМЫ |
| PE20140572A1 (es) | 2008-06-05 | 2014-05-16 | Janssen Pharmaceutica Nv | Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| WO2010033349A1 (en) * | 2008-09-16 | 2010-03-25 | Merck & Co., Inc. | Phthalimide derivative metabotropic glutamate r4 ligands |
| JP2012006837A (ja) * | 2008-09-30 | 2012-01-12 | Mochida Pharmaceut Co Ltd | 2−インドールアクリルアミド類縁体 |
| US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| US8846664B2 (en) | 2008-11-12 | 2014-09-30 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| AR074466A1 (es) * | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Piperidina espiro pirrolidinona y piperidinona sustituidas y su uso terapeutico en enfermedades mediadas por la modulacion de los receptores h3. |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| UA103918C2 (en) | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| EP2404902A1 (en) * | 2009-03-05 | 2012-01-11 | Shionogi&Co., Ltd. | Piperidine and pyrrolidine derivatives having npy y5 receptor antagonism |
| US8653125B2 (en) | 2009-03-05 | 2014-02-18 | Shionogi Co., Ltd. | Cyclohexane derivative having NPY Y5 receptor antagonism |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| WO2011060026A1 (en) | 2009-11-12 | 2011-05-19 | Jansen Pharmaceutica Nv | Piperazinecarboxamide derivative useful as a modulator of fatty acid amide hydrolase (faah) |
| US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| AR083718A1 (es) * | 2010-05-11 | 2013-03-20 | Sanofi Aventis | Fenil cicloalquil pirrolidina (piperidina) espirolactamas y amidas sustituidas, preparacion y uso terapeutico de las mismas |
| WO2011143162A1 (en) * | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| JP5833105B2 (ja) * | 2010-05-11 | 2015-12-16 | サノフイ | 置換n−ヘテロアリールスピロラクタムビピロリジン類、その製造及び治療的使用 |
| UY33469A (es) | 2010-06-29 | 2012-01-31 | Irm Llc Y Novartis Ag | Composiciones y metodos para modular la via de señalizacion de wnt |
| WO2012062759A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| PT2649069E (pt) | 2010-11-08 | 2015-11-20 | Janssen Pharmaceuticals Inc | Derivados de 1,2,4-triazolo[4,3-a]piridina e sua utilização como moduladores alostéricos positivos de recetores mglur2 |
| JP5852665B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2012120050A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US9051265B2 (en) | 2011-06-06 | 2015-06-09 | The Scripps Research Institute | N-benzylindole modulators of PPARG |
| US8957093B2 (en) | 2011-06-06 | 2015-02-17 | The Scripps Research Institute | N-biphenylmethylindole modulators of PPARG |
| WO2013078240A1 (en) | 2011-11-22 | 2013-05-30 | Ripka Amy S | N-biphenylmethylbenzimidazole modulators of pparg |
| US9102669B2 (en) | 2011-12-06 | 2015-08-11 | Janssen Pharmaceutica Nv | Substituted piperidinyl-pyridazinyl derivatives useful as SCD 1 inhibitors |
| WO2013085954A1 (en) | 2011-12-06 | 2013-06-13 | Janssen Pharmaceutica Nv | Substituted piperidinyl-carboxamide derivatives useful as scd 1 inhibitors |
| MX2014013752A (es) * | 2012-05-11 | 2014-12-08 | Abbvie Inc | Inhibidores de nampt. |
| CN105101959B (zh) * | 2012-11-05 | 2018-04-17 | 南特知识产权控股有限责任公司 | 作为刺猬信号传导通路的抑制剂的含有环状磺酰胺的衍生物 |
| TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效rock1及rock2抑制劑之苯基吡唑衍生物 |
| US9828345B2 (en) | 2013-02-28 | 2017-11-28 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent ROCK1 and ROCK2 inhibitors |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| AU2015208233B2 (en) | 2014-01-21 | 2019-08-29 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
| US10016394B2 (en) | 2014-04-16 | 2018-07-10 | The Scripps Research Institute | PPARG modulators for treatment of osteoporosis |
| US20170152226A1 (en) * | 2014-07-16 | 2017-06-01 | Novogen Ltd. | Functionalised and substituted indoles as anti-cancer agents |
| JP6633618B2 (ja) * | 2014-08-21 | 2020-01-22 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | 強力なrock阻害剤としてのタイドバックのベンズアミド誘導体 |
| EP3193603A4 (en) * | 2014-09-10 | 2018-02-28 | Epizyme, Inc. | Isoxazole carboxamide compounds |
| CA2996017A1 (en) * | 2015-08-28 | 2017-03-09 | Glenmark Pharmaceuticals S.A. | Novel carbocyclic compounds as ror gamma modulators |
| BR112018015389B1 (pt) | 2016-03-17 | 2023-12-19 | F. Hoffmann-La Roche Ag | Derivado de 5-etil-4-metil-pirazol-3-carboxamida, seu processo de fabricação, preparação farmacêutica oral e uso |
| CN108815167B (zh) * | 2017-05-24 | 2021-04-13 | 四川晶华生物科技有限公司 | 一种化合物在制备治疗肿瘤的药物中的用途 |
| TW202136238A (zh) * | 2020-01-06 | 2021-10-01 | 大陸商廣東東陽光藥業有限公司 | RORγt抑制劑及其製備方法和用途 |
| WO2022150962A1 (en) * | 2021-01-12 | 2022-07-21 | Westlake Pharmaceutical (Hangzhou) Co., Ltd. | Protease inhibitors, preparation, and uses thereof |
| CN115160269A (zh) * | 2021-04-02 | 2022-10-11 | 北京大学 | 芳甲酰胺类衍生物作为nmdar的正性变构调节剂 |
| IL314330A (en) | 2022-01-18 | 2024-09-01 | Maze Therapeutics Inc | Apol1 inhibitors and methods of use |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2663336B1 (fr) | 1990-06-18 | 1992-09-04 | Adir | Nouveaux derives peptidiques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DK0788498T3 (da) * | 1994-10-26 | 2001-11-05 | Upjohn Co | Phenyloxazolidinoner med antimikrobiel virkning |
| CZ220498A3 (cs) | 1996-01-17 | 1998-11-11 | Novo Nordisk A/S | Deriváty 1,2,4-thiadiazinu a 1,4-thiazinu, příprava a použití |
| ES2283025T3 (es) | 1996-08-30 | 2007-10-16 | Novo Nordisk A/S | Derivados de glp-1.1. |
| HUP0301101A3 (en) | 1996-12-31 | 2009-03-30 | Reddy S Res Foundation | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| DE19726167B4 (de) | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
| BR9810592A (pt) | 1997-07-16 | 2000-09-12 | Novo Nordisk As | Composto, processos para preparar um composto, para tratar ou prevenir doenças do sistema endócrino e para a fabricação de um medicamento, composição farmacêutica, e, uso de um composto |
| CO4970713A1 (es) | 1997-09-19 | 2000-11-07 | Sanofi Synthelabo | Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen |
| JP2001522836A (ja) * | 1997-11-07 | 2001-11-20 | シェーリング コーポレイション | H3レセプターアンタゴニストとしてのフェニル−アルキル−イミダゾール |
| US6221897B1 (en) | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| DE19845405C2 (de) | 1998-10-02 | 2000-07-13 | Aventis Pharma Gmbh | Arylsubstituierte Propanolaminderivate und deren Verwendung |
| AU3126700A (en) | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| GB9900416D0 (en) | 1999-01-08 | 1999-02-24 | Alizyme Therapeutics Ltd | Inhibitors |
| DE60017115T2 (de) * | 1999-02-10 | 2005-12-08 | Mitsubishi Pharma Corp. | Amid-derivate und deren medizinische verwendung |
| TR200102911T2 (tr) * | 1999-04-09 | 2002-01-21 | Astrazeneca Ab | Adamantan türevleri. |
| AU3956900A (en) | 1999-04-16 | 2000-11-02 | Boehringer Ingelheim International Gmbh | Substituted imidazoles, their preparation and use |
| JP2002543200A (ja) | 1999-04-30 | 2002-12-17 | ニューロゲン コーポレイション | 9H−ピリミド[4、5−b]インドール誘導体:CRF1特異性リガンド |
| GB9911863D0 (en) | 1999-05-21 | 1999-07-21 | Knoll Ag | Therapeutic agents |
| SE9901875D0 (sv) * | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
| US6399640B1 (en) | 1999-06-18 | 2002-06-04 | Merck & Co., Inc. | Arylthiazolidinedione and aryloxazolidinedione derivatives |
| BR0012752A (pt) | 1999-07-29 | 2002-04-02 | Lilly Co Eli | Benzofuril piperazinas e benzofuril homopiperazinas: agonistas de serotonina |
| AU774071B2 (en) | 1999-09-01 | 2004-06-17 | Sanofi-Aventis Deutschland Gmbh | Sulfonyl carboxamide derivatives, method for their production and their use as medicaments |
| CA2407538C (en) | 2000-04-28 | 2007-01-09 | Asahi Kasei Kabushiki Kaisha | Novel bicyclic compounds |
| WO2001085695A1 (en) | 2000-05-11 | 2001-11-15 | Bristol-Myers Squibb Co. | Tetrahydroisoquinoline analogs useful as growth hormone secretagogues |
| JP2003534377A (ja) | 2000-05-30 | 2003-11-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬 |
| US6525202B2 (en) * | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| JP2004504321A (ja) * | 2000-07-17 | 2004-02-12 | ランバクシー ラボラトリーズ リミテッド | 抗微生物剤としてのオキサゾリジノン誘導体 |
| IL153645A0 (en) * | 2000-07-31 | 2003-07-06 | Smithkline Beecham Plc | Carboxamide compounds and their use as antagonists of a human 11cby receptor |
| JO2654B1 (en) * | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
| JO2409B1 (en) * | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
| JP2002338537A (ja) * | 2001-05-16 | 2002-11-27 | Mitsubishi Pharma Corp | アミド化合物およびその医薬用途 |
| WO2002098839A1 (en) * | 2001-06-01 | 2002-12-12 | Tanabe Seiyaku Co., Ltd. | Biphenylcarboxamides and process for preparation thereof |
| WO2002098871A1 (en) * | 2001-06-01 | 2002-12-12 | Tanabe Seiyaku Co., Ltd. | Phenylcarboxamides and process for preparation thereof |
| AU2002346048A1 (en) * | 2001-06-07 | 2002-12-16 | Merck And Co., Inc. | Benzodiazepine bradykinin antagonists |
| DE10142734A1 (de) | 2001-08-31 | 2003-03-27 | Aventis Pharma Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AU2003227437A1 (en) * | 2002-04-23 | 2003-11-10 | Shionogi And Co., Ltd. | PYRAZOLO(1,5-a)PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME |
| JP2004175739A (ja) * | 2002-11-28 | 2004-06-24 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
-
2003
- 2003-02-14 DE DE10306250A patent/DE10306250A1/de not_active Withdrawn
-
2004
- 2004-02-13 RU RU2005128551/04A patent/RU2005128551A/ru not_active Application Discontinuation
- 2004-02-13 PA PA20048595901A patent/PA8595901A1/es unknown
- 2004-02-13 UA UAA200508733A patent/UA86760C2/ru unknown
- 2004-02-13 PL PL378065A patent/PL378065A1/pl not_active Application Discontinuation
- 2004-02-13 PE PE2004000158A patent/PE20040952A1/es not_active Application Discontinuation
- 2004-02-13 TW TW093103412A patent/TW200510297A/zh unknown
- 2004-02-13 OA OA1200500227A patent/OA13027A/en unknown
- 2004-02-13 KR KR1020057014989A patent/KR20050101215A/ko not_active Ceased
- 2004-02-13 JP JP2006501827A patent/JP2006517563A/ja active Pending
- 2004-02-13 AU AU2004212145A patent/AU2004212145B2/en not_active Ceased
- 2004-02-13 UY UY28186A patent/UY28186A1/es unknown
- 2004-02-13 MY MYPI20040479A patent/MY139102A/en unknown
- 2004-02-13 NZ NZ541823A patent/NZ541823A/en unknown
- 2004-02-13 EP EP04710808A patent/EP1597228A2/de not_active Withdrawn
- 2004-02-13 CA CA002516118A patent/CA2516118A1/en not_active Abandoned
- 2004-02-13 HR HR20050710A patent/HRP20050710A2/xx not_active Application Discontinuation
- 2004-02-13 RS YUP-2005/0666A patent/RS20050666A/sr unknown
- 2004-02-13 CN CNB2004800098606A patent/CN100506792C/zh not_active Expired - Fee Related
- 2004-02-13 WO PCT/EP2004/001342 patent/WO2004072025A2/de not_active Ceased
- 2004-02-13 MX MXPA05008449A patent/MXPA05008449A/es active IP Right Grant
- 2004-02-13 BR BRPI0407504-8A patent/BRPI0407504A/pt not_active IP Right Cessation
- 2004-02-16 AR ARP040100469A patent/AR044496A1/es unknown
-
2005
- 2005-08-10 ZA ZA200506369A patent/ZA200506369B/en unknown
- 2005-08-11 MA MA28430A patent/MA27735A1/fr unknown
- 2005-08-11 CO CO05079788A patent/CO5690548A2/es not_active Application Discontinuation
- 2005-08-11 EC EC2005005967A patent/ECSP055967A/es unknown
- 2005-08-12 TN TNP2005000194A patent/TNSN05194A1/en unknown
- 2005-09-12 NO NO20054220A patent/NO20054220L/no unknown
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 |
| 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 |
| JP2006517563A (ja) | 2006-07-27 |
| CO5690548A2 (es) | 2006-10-31 |
| AU2004212145A1 (en) | 2004-08-26 |
| CA2516118A1 (en) | 2004-08-26 |
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