ZA200403035B - Imidazole-4-carboxamide derivatives, preparation and use thereof for treatment of obesity. - Google Patents
Imidazole-4-carboxamide derivatives, preparation and use thereof for treatment of obesity. Download PDFInfo
- Publication number
- ZA200403035B ZA200403035B ZA200403035A ZA200403035A ZA200403035B ZA 200403035 B ZA200403035 B ZA 200403035B ZA 200403035 A ZA200403035 A ZA 200403035A ZA 200403035 A ZA200403035 A ZA 200403035A ZA 200403035 B ZA200403035 B ZA 200403035B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- alkoxy
- hydroxy
- phenyl
- Prior art date
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- 208000008589 Obesity Diseases 0.000 title claims description 108
- 235000020824 obesity Nutrition 0.000 title claims description 100
- 238000002360 preparation method Methods 0.000 title description 7
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical class NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 357
- 150000001875 compounds Chemical class 0.000 claims description 235
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 183
- 125000003545 alkoxy group Chemical group 0.000 claims description 165
- -1 cyano, benzyl Chemical group 0.000 claims description 162
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 145
- 229910052736 halogen Inorganic materials 0.000 claims description 122
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 95
- 239000001257 hydrogen Substances 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 239000003814 drug Substances 0.000 claims description 84
- 150000002367 halogens Chemical class 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 81
- 150000002148 esters Chemical class 0.000 claims description 78
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
- 239000003795 chemical substances by application Substances 0.000 claims description 60
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 56
- 208000035475 disorder Diseases 0.000 claims description 53
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- 239000011737 fluorine Substances 0.000 claims description 42
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- 229910052792 caesium Inorganic materials 0.000 claims description 26
- 125000001246 bromo group Chemical group Br* 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 206010020772 Hypertension Diseases 0.000 claims description 19
- 230000029087 digestion Effects 0.000 claims description 19
- 230000004060 metabolic process Effects 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 239000003472 antidiabetic agent Substances 0.000 claims description 13
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 10
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 10
- 229940125753 fibrate Drugs 0.000 claims description 10
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- 230000036186 satiety Effects 0.000 claims description 10
- 235000019627 satiety Nutrition 0.000 claims description 10
- 230000035924 thermogenesis Effects 0.000 claims description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
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- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 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 claims description 8
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- 208000032841 Bulimia Diseases 0.000 claims description 7
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
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- 230000036528 appetite Effects 0.000 claims description 7
- 230000003143 atherosclerotic effect Effects 0.000 claims description 7
- 230000003542 behavioural effect Effects 0.000 claims description 7
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 7
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- 230000019771 cognition Effects 0.000 claims description 7
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- 235000012631 food intake Nutrition 0.000 claims description 7
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 7
- 208000000509 infertility Diseases 0.000 claims description 7
- 231100000535 infertility Toxicity 0.000 claims description 7
- 230000036512 infertility Effects 0.000 claims description 7
- 231100000551 menstrual abnormality Toxicity 0.000 claims description 7
- 230000002093 peripheral effect Effects 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 102000004877 Insulin Human genes 0.000 claims description 4
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 40
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 16
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- 239000003937 drug carrier Substances 0.000 claims 12
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 9
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 9
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 4
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- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- NPSKEUHPMODZNH-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2-chlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=CC=C1Cl NPSKEUHPMODZNH-UHFFFAOYSA-N 0.000 claims 1
- FYMACJSAHLBMHV-UHFFFAOYSA-N 1h-imidazole-5-carbohydrazide Chemical compound NNC(=O)C1=CN=CN1 FYMACJSAHLBMHV-UHFFFAOYSA-N 0.000 claims 1
- WIUAZKNCWYGPFK-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=CC=C1Cl WIUAZKNCWYGPFK-UHFFFAOYSA-N 0.000 claims 1
- UIYADAADYGZZIU-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-(2,4-dichlorophenyl)-5-methylimidazole-4-carbohydrazide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NNC=2C(=CC(Cl)=CC=2)Cl)N=C1C1=CC=CC=C1Cl UIYADAADYGZZIU-UHFFFAOYSA-N 0.000 claims 1
- JUNAMSBYRYGGKP-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-(2,4-dichlorophenyl)imidazole-4-carbohydrazide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC=CC=2)Cl)=NC(C(=O)NNC=2C(=CC(Cl)=CC=2)Cl)=C1 JUNAMSBYRYGGKP-UHFFFAOYSA-N 0.000 claims 1
- UQEGCEQUXXMVJH-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-[2-(trifluoromethyl)phenyl]imidazole-4-carbohydrazide Chemical compound FC(F)(F)C1=CC=CC=C1NNC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC=CC=2)Cl)=N1 UQEGCEQUXXMVJH-UHFFFAOYSA-N 0.000 claims 1
- ZHBFAKOGGWYAHK-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-[2-chloro-4-(trifluoromethyl)phenyl]imidazole-4-carbohydrazide Chemical compound ClC1=CC(C(F)(F)F)=CC=C1NNC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC=CC=2)Cl)=N1 ZHBFAKOGGWYAHK-UHFFFAOYSA-N 0.000 claims 1
- YPWSMQSTSSAHQP-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-[3-(trifluoromethyl)phenyl]imidazole-4-carbohydrazide Chemical compound FC(F)(F)C1=CC=CC(NNC(=O)C=2N=C(N(C=2)C=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)=C1 YPWSMQSTSSAHQP-UHFFFAOYSA-N 0.000 claims 1
- GLYCMCSERQIQQF-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n'-[4-(trifluoromethyl)phenyl]imidazole-4-carbohydrazide Chemical compound C1=CC(C(F)(F)F)=CC=C1NNC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC=CC=2)Cl)=N1 GLYCMCSERQIQQF-UHFFFAOYSA-N 0.000 claims 1
- QGXIQZPDTVQGDL-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n-(1-pyridin-2-ylpiperidin-4-yl)imidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC=CC=2)Cl)=NC(C(=O)NC2CCN(CC2)C=2N=CC=CC=2)=C1 QGXIQZPDTVQGDL-UHFFFAOYSA-N 0.000 claims 1
- YANPAVHFFWLLEL-ICSRJNTNSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n-[(1s,2s)-2-hydroxycyclohexyl]imidazole-4-carboxamide Chemical compound O[C@H]1CCCC[C@@H]1NC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC=CC=2)Cl)=N1 YANPAVHFFWLLEL-ICSRJNTNSA-N 0.000 claims 1
- OWLDJASELBBGJT-HKUYNNGSSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n-[(1s,2s)-2-hydroxycyclopentyl]imidazole-4-carboxamide Chemical compound O[C@H]1CCC[C@@H]1NC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC=CC=2)Cl)=N1 OWLDJASELBBGJT-HKUYNNGSSA-N 0.000 claims 1
- FKCOPYQWDBZUKT-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 FKCOPYQWDBZUKT-UHFFFAOYSA-N 0.000 claims 1
- VWTKGXQIGSTRAE-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(4-chlorophenyl)-n-pyridin-4-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC=CC=2)Cl)=NC(C(=O)NC=2C=CN=CC=2)=C1 VWTKGXQIGSTRAE-UHFFFAOYSA-N 0.000 claims 1
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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EP (1) | EP1432691A1 (fr) |
JP (1) | JP2005508384A (fr) |
KR (1) | KR20040040472A (fr) |
CN (2) | CN1865248A (fr) |
AR (1) | AR036608A1 (fr) |
BR (1) | BR0212986A (fr) |
CA (1) | CA2459745A1 (fr) |
CO (1) | CO5560560A2 (fr) |
EC (1) | ECSP045076A (fr) |
GT (1) | GT200200188A (fr) |
HN (1) | HN2002000266A (fr) |
HR (1) | HRP20040308A2 (fr) |
HU (1) | HUP0402376A2 (fr) |
IL (1) | IL160524A0 (fr) |
MA (1) | MA27684A1 (fr) |
MX (1) | MXPA04002037A (fr) |
NO (1) | NO20041216L (fr) |
NZ (1) | NZ531841A (fr) |
PE (1) | PE20030547A1 (fr) |
PL (1) | PL369326A1 (fr) |
RU (1) | RU2004112770A (fr) |
UY (1) | UY27450A1 (fr) |
WO (1) | WO2003040107A1 (fr) |
ZA (1) | ZA200403035B (fr) |
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AU2002319627A1 (en) | 2001-07-20 | 2003-03-03 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
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2004
- 2004-03-19 CO CO04026619A patent/CO5560560A2/es not_active Application Discontinuation
- 2004-03-23 NO NO20041216A patent/NO20041216L/no not_active Application Discontinuation
- 2004-03-31 HR HR20040308A patent/HRP20040308A2/xx not_active Application Discontinuation
- 2004-04-21 ZA ZA200403035A patent/ZA200403035B/en unknown
- 2004-04-22 EC EC2004005076A patent/ECSP045076A/es unknown
- 2004-04-23 MA MA27653A patent/MA27684A1/fr unknown
-
2005
- 2005-05-20 US US11/133,751 patent/US20050256167A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
IL160524A0 (en) | 2004-07-25 |
EP1432691A1 (fr) | 2004-06-30 |
BR0212986A (pt) | 2004-08-17 |
US20040063691A1 (en) | 2004-04-01 |
CA2459745A1 (fr) | 2003-05-15 |
WO2003040107A8 (fr) | 2004-07-29 |
CN1599724A (zh) | 2005-03-23 |
US20050256167A1 (en) | 2005-11-17 |
RU2004112770A (ru) | 2005-10-10 |
UY27450A1 (es) | 2003-04-30 |
KR20040040472A (ko) | 2004-05-12 |
CO5560560A2 (es) | 2005-09-30 |
NZ531841A (en) | 2005-09-30 |
NO20041216L (no) | 2004-05-05 |
AR036608A1 (es) | 2004-09-22 |
HUP0402376A2 (hu) | 2005-02-28 |
PE20030547A1 (es) | 2003-08-18 |
WO2003040107A1 (fr) | 2003-05-15 |
PL369326A1 (en) | 2005-04-18 |
JP2005508384A (ja) | 2005-03-31 |
US6960601B2 (en) | 2005-11-01 |
HRP20040308A2 (en) | 2006-08-31 |
MXPA04002037A (es) | 2004-06-07 |
MA27684A1 (fr) | 2006-01-02 |
CN1865248A (zh) | 2006-11-22 |
HN2002000266A (es) | 2003-11-16 |
ECSP045076A (es) | 2004-05-28 |
GT200200188A (es) | 2003-06-25 |
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