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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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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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- 125000002255 pentenyl group Chemical group C(=CCCC)* 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
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- 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
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- 238000000527 sonication Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 150000003431 steroids Chemical class 0.000 description 1
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- 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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- 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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- 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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- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
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- Heart & Thoracic Surgery (AREA)
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- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (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 |
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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 (enExample) |
| EP (1) | EP1615925B1 (enExample) |
| JP (1) | JP4711948B2 (enExample) |
| KR (1) | KR101102742B1 (enExample) |
| CN (1) | CN100455581C (enExample) |
| AT (1) | ATE432280T1 (enExample) |
| AU (1) | AU2004228416B9 (enExample) |
| BR (1) | BRPI0408817A (enExample) |
| CA (1) | CA2520855C (enExample) |
| DE (1) | DE602004021247D1 (enExample) |
| ES (1) | ES2327929T3 (enExample) |
| FR (1) | FR2852957B1 (enExample) |
| IL (1) | IL170834A (enExample) |
| MX (1) | MXPA05010278A (enExample) |
| NZ (1) | NZ542763A (enExample) |
| RU (1) | RU2358974C2 (enExample) |
| WO (1) | WO2004089951A1 (enExample) |
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 |
| EP2072516A1 (en) * | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine derivates as Melancortin-4 receptor antagonists |
| EP2072050A1 (en) | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Compounds with anti-emetic effect |
| EP2168965A1 (en) * | 2008-09-25 | 2010-03-31 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine, imidazopyrazine, imidazopyridazine and imidazopyrimidine derivatives as melanocortin-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 |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CN102271509A (zh) | 2008-10-31 | 2011-12-07 | 默沙东公司 | 用于抗糖尿病药的新型环苯并咪唑衍生物 |
| 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 |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| RU2013109143A (ru) | 2010-08-05 | 2014-09-10 | Амджен Инк. | Бензимидазол- и азабензимидазолсодержащие соединения, которые ингибируют киназу анапластической лимфомы |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8674113B2 (en) | 2010-12-10 | 2014-03-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
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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 | |
| AU766191B2 (en) * | 1999-06-04 | 2003-10-09 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| JP2003528810A (ja) * | 1999-08-04 | 2003-09-30 | ミレニアム ファーマスーティカルズ インク | メラノコルチン−４受容体結合化合物及びその使用方法 |
| 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 |
| 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 |
| IL156031A0 (en) * | 2000-12-15 | 2003-12-23 | Vertex Pharma | Fused heterocyclic derivatives and pharmaceutical compositions containing the same |
| EP1465888A2 (en) * | 2002-01-10 | 2004-10-13 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2358974C2 (ru) | 2009-06-20 |
| CA2520855A1 (fr) | 2004-10-21 |
| EP1615925B1 (fr) | 2009-05-27 |
| US20060173036A1 (en) | 2006-08-03 |
| CN1768058A (zh) | 2006-05-03 |
| AU2004228416B2 (en) | 2010-02-11 |
| CN100455581C (zh) | 2009-01-28 |
| JP4711948B2 (ja) | 2011-06-29 |
| AU2004228416B8 (en) | 2010-03-04 |
| CA2520855C (fr) | 2014-05-13 |
| US7495009B2 (en) | 2009-02-24 |
| HK1090640A1 (zh) | 2006-12-29 |
| KR101102742B1 (ko) | 2012-01-05 |
| FR2852957B1 (fr) | 2005-06-10 |
| JP2006522076A (ja) | 2006-09-28 |
| ATE432280T1 (de) | 2009-06-15 |
| AU2004228416B9 (en) | 2010-03-11 |
| AU2004228416A1 (en) | 2004-10-21 |
| WO2004089951A1 (fr) | 2004-10-21 |
| MXPA05010278A (es) | 2005-11-17 |
| IL170834A (en) | 2010-12-30 |
| BRPI0408817A (pt) | 2006-04-04 |
| ES2327929T3 (es) | 2009-11-05 |
| DE602004021247D1 (de) | 2009-07-09 |
| RU2005133441A (ru) | 2006-05-10 |
| WO2004089951A8 (fr) | 2006-01-12 |
| KR20060002893A (ko) | 2006-01-09 |
| EP1615925A1 (fr) | 2006-01-18 |
| FR2852957A1 (fr) | 2004-10-01 |
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