NZ542763A - Imidazopyridine derivatives as melanocortin receptor agonists - Google Patents
Imidazopyridine derivatives as melanocortin receptor agonistsInfo
- Publication number
- NZ542763A NZ542763A NZ542763A NZ54276304A NZ542763A NZ 542763 A NZ542763 A NZ 542763A NZ 542763 A NZ542763 A NZ 542763A NZ 54276304 A NZ54276304 A NZ 54276304A NZ 542763 A NZ542763 A NZ 542763A
- Authority
- NZ
- New Zealand
- Prior art keywords
- radical
- alkyl
- substituted
- list consisting
- halo
- Prior art date
Links
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract description 4
- 239000000336 melanocortin receptor agonist Substances 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 claims abstract description 15
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 alkyl radical Chemical class 0.000 claims description 180
- 150000001875 compounds Chemical class 0.000 claims description 99
- 150000003254 radicals Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 45
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 23
- 150000005840 aryl radicals Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 206010006895 Cachexia Diseases 0.000 claims description 17
- 239000000010 aprotic solvent Substances 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002540 isothiocyanates Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 8
- 108010008364 Melanocortins Proteins 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- 239000002865 melanocortin Substances 0.000 claims description 7
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 229940095074 cyclic amp Drugs 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003586 protic polar solvent Substances 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
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- 229910014585 C2-Ce Inorganic materials 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 230000027455 binding Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 239000012980 RPMI-1640 medium Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 244000309466 calf Species 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
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- 210000002966 serum Anatomy 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 26
- 241000894007 species Species 0.000 claims 13
- 125000003107 substituted aryl group Chemical group 0.000 claims 12
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 claims 1
- 108010001478 Bacitracin Proteins 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- 239000012979 RPMI medium Substances 0.000 claims 1
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- 229930184125 bacitracin Natural products 0.000 claims 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims 1
- 239000003365 glass fiber Substances 0.000 claims 1
- 238000012417 linear regression Methods 0.000 claims 1
- 239000012139 lysis buffer Substances 0.000 claims 1
- 230000009871 nonspecific binding Effects 0.000 claims 1
- 230000009870 specific binding Effects 0.000 claims 1
- 102000004378 Melanocortin Receptors Human genes 0.000 abstract description 13
- 108090000950 Melanocortin Receptors Proteins 0.000 abstract description 13
- 230000001575 pathological effect Effects 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 239000000203 mixture Substances 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
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- 125000005843 halogen group Chemical group 0.000 description 21
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 15
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
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- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- KGGROHGITJFOHJ-UHFFFAOYSA-N methyl 4-carbonisothiocyanatidoylbenzoate Chemical compound COC(=O)C1=CC=C(C(=O)N=C=S)C=C1 KGGROHGITJFOHJ-UHFFFAOYSA-N 0.000 description 1
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- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- UWTCPENWRHQRTL-UHFFFAOYSA-M potassium carbamic acid hydrogen carbonate Chemical compound C([O-])(O)=O.[K+].C(N)(O)=O UWTCPENWRHQRTL-UHFFFAOYSA-M 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- UNZYWGIXVVCSAX-UHFFFAOYSA-N tert-butyl n-[4-(methoxycarbamoylamino)phenyl]carbamate Chemical compound CONC(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 UNZYWGIXVVCSAX-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XJVIPPHGDPEDJL-UHFFFAOYSA-N thiourea;hydrochloride Chemical compound Cl.NC(N)=S XJVIPPHGDPEDJL-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Child & Adolescent Psychology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0303924A FR2852957B1 (fr) | 2003-03-31 | 2003-03-31 | Nouveaux derives d'imidazo-pyridine et leur utilisation en tant que medicament |
| PCT/FR2004/000785 WO2004089951A1 (fr) | 2003-03-31 | 2004-03-29 | Derives d’imidazo-pyridine ayant une affinite sur des recepteurs de la melanocortine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ542763A true NZ542763A (en) | 2007-11-30 |
Family
ID=32947292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ542763A NZ542763A (en) | 2003-03-31 | 2004-03-29 | Imidazopyridine derivatives as melanocortin receptor agonists |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7495009B2 (https=) |
| EP (1) | EP1615925B1 (https=) |
| JP (1) | JP4711948B2 (https=) |
| KR (1) | KR101102742B1 (https=) |
| CN (1) | CN100455581C (https=) |
| AT (1) | ATE432280T1 (https=) |
| AU (1) | AU2004228416B9 (https=) |
| BR (1) | BRPI0408817A (https=) |
| CA (1) | CA2520855C (https=) |
| DE (1) | DE602004021247D1 (https=) |
| ES (1) | ES2327929T3 (https=) |
| FR (1) | FR2852957B1 (https=) |
| IL (1) | IL170834A (https=) |
| MX (1) | MXPA05010278A (https=) |
| NZ (1) | NZ542763A (https=) |
| RU (1) | RU2358974C2 (https=) |
| WO (1) | WO2004089951A1 (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2862971B1 (fr) * | 2003-11-28 | 2006-03-24 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et d'imidazo-pyridine et leur utilisation en tant que medicament |
| TW200911803A (en) * | 2007-07-16 | 2009-03-16 | Organon Nv | 6-phenyl-1H-imidazo [4,5-c] pyridine-4-carbonitrile derivatives |
| EP2072050A1 (en) | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Compounds with anti-emetic effect |
| EP2072516A1 (en) * | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine derivates as Melancortin-4 receptor antagonists |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| EP2168965A1 (en) * | 2008-09-25 | 2010-03-31 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine, imidazopyrazine, imidazopyridazine and imidazopyrimidine derivatives as melanocortin-4 receptor antagonists |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| UY32470A (es) | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| CN103168032A (zh) | 2010-08-05 | 2013-06-19 | 安美基公司 | 抑制间变性淋巴瘤激酶的苯并咪唑和氮杂苯并咪唑化合物 |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
| UY33779A (es) | 2010-12-10 | 2012-07-31 | Boehringer Ingelheim Int | ?2-(fenilamino)-1H-bencimidazol-5-carboxamidas novedosas? |
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| DE4416433A1 (de) * | 1994-05-10 | 1995-11-16 | Hoechst Ag | Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung der Verbindungen zur Behandlung von Krankheiten |
| DE19503160A1 (de) * | 1995-02-01 | 1996-08-08 | Bayer Ag | Verwendung von Phenylcyclohexylcarbonsäureamiden |
| UA62972C2 (en) * | 1997-07-03 | 2004-01-15 | Application of imidazopyrimidins and imidazopyridins for the treatment of neural disorders | |
| WO2000074679A1 (en) * | 1999-06-04 | 2000-12-14 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| MXPA02001160A (es) * | 1999-08-04 | 2002-07-02 | Millennium Pharm Inc | Compuestos que se unen a los receptores para melanocortina-4, y metodo de uso de estos. |
| AU2001236919A1 (en) | 2000-02-09 | 2001-08-20 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Premeiotic and postmeiotic origin of teratomas: isolated teratoma stem cells for therapeutic uses |
| EP1289526A4 (en) * | 2000-05-30 | 2005-03-16 | Merck & Co Inc | MELANOCORTIN RECEPTOR AGONISTS |
| HUP0303494A3 (en) * | 2000-12-15 | 2009-08-28 | Vertex Pharma | Parmaceutical compositions containing bacterial gyrase inhibitors and uses thereof |
| EP1465888A2 (en) * | 2002-01-10 | 2004-10-13 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
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2003
- 2003-03-31 FR FR0303924A patent/FR2852957B1/fr not_active Expired - Fee Related
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- 2004-03-29 KR KR1020057018420A patent/KR101102742B1/ko not_active Expired - Fee Related
- 2004-03-29 CA CA2520855A patent/CA2520855C/fr not_active Expired - Fee Related
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- 2004-03-29 DE DE602004021247T patent/DE602004021247D1/de not_active Expired - Lifetime
- 2004-03-29 EP EP04742386A patent/EP1615925B1/fr not_active Expired - Lifetime
- 2004-03-29 CN CNB2004800084919A patent/CN100455581C/zh not_active Expired - Fee Related
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- 2004-03-29 RU RU2005133441/04A patent/RU2358974C2/ru not_active IP Right Cessation
- 2004-03-29 WO PCT/FR2004/000785 patent/WO2004089951A1/fr not_active Ceased
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| Publication number | Publication date |
|---|---|
| KR20060002893A (ko) | 2006-01-09 |
| ES2327929T3 (es) | 2009-11-05 |
| DE602004021247D1 (de) | 2009-07-09 |
| KR101102742B1 (ko) | 2012-01-05 |
| IL170834A (en) | 2010-12-30 |
| AU2004228416B8 (en) | 2010-03-04 |
| US20060173036A1 (en) | 2006-08-03 |
| ATE432280T1 (de) | 2009-06-15 |
| WO2004089951A1 (fr) | 2004-10-21 |
| CA2520855C (fr) | 2014-05-13 |
| WO2004089951A8 (fr) | 2006-01-12 |
| HK1090640A1 (zh) | 2006-12-29 |
| RU2358974C2 (ru) | 2009-06-20 |
| AU2004228416A1 (en) | 2004-10-21 |
| EP1615925A1 (fr) | 2006-01-18 |
| RU2005133441A (ru) | 2006-05-10 |
| CN100455581C (zh) | 2009-01-28 |
| AU2004228416B2 (en) | 2010-02-11 |
| US7495009B2 (en) | 2009-02-24 |
| CA2520855A1 (fr) | 2004-10-21 |
| JP2006522076A (ja) | 2006-09-28 |
| AU2004228416B9 (en) | 2010-03-11 |
| MXPA05010278A (es) | 2005-11-17 |
| EP1615925B1 (fr) | 2009-05-27 |
| FR2852957A1 (fr) | 2004-10-01 |
| JP4711948B2 (ja) | 2011-06-29 |
| BRPI0408817A (pt) | 2006-04-04 |
| FR2852957B1 (fr) | 2005-06-10 |
| CN1768058A (zh) | 2006-05-03 |
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