ZA200404805B - 5,6-diaryl-pyrazine-2-amide derivatives as CB1 antagonists. - Google Patents
5,6-diaryl-pyrazine-2-amide derivatives as CB1 antagonists. Download PDFInfo
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- ZA200404805B ZA200404805B ZA200404805A ZA200404805A ZA200404805B ZA 200404805 B ZA200404805 B ZA 200404805B ZA 200404805 A ZA200404805 A ZA 200404805A ZA 200404805 A ZA200404805 A ZA 200404805A ZA 200404805 B ZA200404805 B ZA 200404805B
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- 229940124802 CB1 antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 1-adamantylmethyl Chemical group 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 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 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 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 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- JSXUTJNCMVFTEN-UHFFFAOYSA-N 5,6-diphenylpyrazine-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1=NC(C(=O)O)=CN=C1C1=CC=CC=C1 JSXUTJNCMVFTEN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 208000017701 Endocrine disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 210000005095 gastrointestinal system Anatomy 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001850 reproductive effect Effects 0.000 claims 2
- 230000000241 respiratory effect Effects 0.000 claims 2
- 210000002345 respiratory system Anatomy 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- BXRSYUFMJUGANE-UHFFFAOYSA-N 5,6-bis(2-chlorophenyl)-n-cyclohexylpyrazine-2-carboxamide Chemical compound ClC1=CC=CC=C1C1=NC=C(C(=O)NC2CCCCC2)N=C1C1=CC=CC=C1Cl BXRSYUFMJUGANE-UHFFFAOYSA-N 0.000 claims 1
- OTQMQCJNTMMDQF-UHFFFAOYSA-N 5,6-bis(2-chlorophenyl)-n-phenylpyrazine-2-carboxamide Chemical compound ClC1=CC=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=CC=C1Cl OTQMQCJNTMMDQF-UHFFFAOYSA-N 0.000 claims 1
- SELNPJHTVVHETF-UHFFFAOYSA-N 5,6-bis(2-chlorophenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound ClC1=CC=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=CC=C1Cl SELNPJHTVVHETF-UHFFFAOYSA-N 0.000 claims 1
- MVJXAVCGHLLTTE-UHFFFAOYSA-N 5,6-bis(4-bromophenyl)-n-cyclohexylpyrazine-2-carboxamide Chemical compound C1=CC(Br)=CC=C1C1=NC=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Br)C=C1 MVJXAVCGHLLTTE-UHFFFAOYSA-N 0.000 claims 1
- KTHRWPCGPDGGSF-UHFFFAOYSA-N 5,6-bis(4-bromophenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(Br)=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Br)C=C1 KTHRWPCGPDGGSF-UHFFFAOYSA-N 0.000 claims 1
- FDSVRRAVMKJSOK-UHFFFAOYSA-N 5,6-bis(4-chlorophenyl)-n-cyclohexylpyrazine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1 FDSVRRAVMKJSOK-UHFFFAOYSA-N 0.000 claims 1
- QHIJQKXKXDZQEW-UHFFFAOYSA-N 5,6-bis(4-chlorophenyl)-n-phenylpyrazine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 QHIJQKXKXDZQEW-UHFFFAOYSA-N 0.000 claims 1
- FBMFLCCMSCORDS-UHFFFAOYSA-N 5,6-bis(4-chlorophenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1 FBMFLCCMSCORDS-UHFFFAOYSA-N 0.000 claims 1
- DSSMWRUERDOSAD-UHFFFAOYSA-N 5,6-bis(4-methoxyphenyl)-n-phenylpyrazine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(OC)C=C1 DSSMWRUERDOSAD-UHFFFAOYSA-N 0.000 claims 1
- CKIMQGCGMNRLMG-UHFFFAOYSA-N 5,6-bis(4-methoxyphenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(OC)C=C1 CKIMQGCGMNRLMG-UHFFFAOYSA-N 0.000 claims 1
- GWGILOWBUBUWOZ-UHFFFAOYSA-N 5,6-bis(4-methoxyphenyl)pyrazine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(O)=O)N=C1C1=CC=C(OC)C=C1 GWGILOWBUBUWOZ-UHFFFAOYSA-N 0.000 claims 1
- AKCXCZPEESTMSV-UHFFFAOYSA-N 5,6-bis(4-methylphenyl)-n-phenylpyrazine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(C)C=C1 AKCXCZPEESTMSV-UHFFFAOYSA-N 0.000 claims 1
- CLAIXBYIEGGFDP-UHFFFAOYSA-N 5,6-bis(4-methylphenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(C)C=C1 CLAIXBYIEGGFDP-UHFFFAOYSA-N 0.000 claims 1
- XIGDSDXHJVSFBZ-UHFFFAOYSA-N 5,6-diphenyl-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NC=1C(=O)NN1CCCCC1 XIGDSDXHJVSFBZ-UHFFFAOYSA-N 0.000 claims 1
- QLFKLOBXDDGAQT-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl QLFKLOBXDDGAQT-UHFFFAOYSA-N 0.000 claims 1
- GGJLRNSPAGCZKZ-UHFFFAOYSA-N 6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-n-piperidin-1-ylpyrazine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN=C1C1=CC=C(Cl)C=C1Cl GGJLRNSPAGCZKZ-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- WQEXKULWDFFZMT-UHFFFAOYSA-N n,5,6-triphenylpyrazine-2-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NC=1C(=O)NC1=CC=CC=C1 WQEXKULWDFFZMT-UHFFFAOYSA-N 0.000 claims 1
- HOAIFTWDCHXJRY-UHFFFAOYSA-N n-cyclohexyl-5,6-bis(4-methoxyphenyl)pyrazine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(OC)C=C1 HOAIFTWDCHXJRY-UHFFFAOYSA-N 0.000 claims 1
- XMYWOFZJZKASQO-UHFFFAOYSA-N n-cyclohexyl-5,6-bis(4-methylphenyl)pyrazine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NC=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(C)C=C1 XMYWOFZJZKASQO-UHFFFAOYSA-N 0.000 claims 1
- VWNCSOQRHOYLDZ-UHFFFAOYSA-N n-cyclohexyl-5,6-diphenylpyrazine-2-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=NC=1C(=O)NC1CCCCC1 VWNCSOQRHOYLDZ-UHFFFAOYSA-N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000018658 Myotonin-Protein Kinase Human genes 0.000 description 1
- 108010052185 Myotonin-Protein Kinase Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004576 sand Substances 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
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Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Life Sciences & Earth Sciences (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| SE0104330A SE0104330D0 (sv) | 2001-12-19 | 2001-12-19 | Therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404805B true ZA200404805B (en) | 2005-08-15 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| ZA200404805A ZA200404805B (en) | 2001-12-19 | 2004-06-17 | 5,6-diaryl-pyrazine-2-amide derivatives as CB1 antagonists. |
Country Status (25)
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| US (1) | US7342019B2 (de) |
| EP (1) | EP1458690B1 (de) |
| JP (1) | JP2005517655A (de) |
| KR (1) | KR20040068286A (de) |
| CN (1) | CN1620438A (de) |
| AR (1) | AR038044A1 (de) |
| AT (1) | ATE354570T1 (de) |
| AU (1) | AU2002352425A1 (de) |
| BR (1) | BR0214989A (de) |
| CA (1) | CA2469786A1 (de) |
| CO (1) | CO5590917A2 (de) |
| DE (1) | DE60218340T2 (de) |
| ES (1) | ES2280599T3 (de) |
| HU (1) | HUP0402026A3 (de) |
| IL (1) | IL162377A0 (de) |
| IS (1) | IS7314A (de) |
| MX (1) | MXPA04005990A (de) |
| NO (1) | NO20043022L (de) |
| NZ (1) | NZ533275A (de) |
| PL (1) | PL369731A1 (de) |
| RU (1) | RU2004116916A (de) |
| SE (1) | SE0104330D0 (de) |
| TW (1) | TW200410694A (de) |
| WO (1) | WO2003051851A1 (de) |
| ZA (1) | ZA200404805B (de) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7704995B2 (en) | 2002-05-03 | 2010-04-27 | Exelixis, Inc. | Protein kinase modulators and methods of use |
| GB0216700D0 (en) | 2002-07-18 | 2002-08-28 | Astrazeneca Ab | Process |
| EP1546115A4 (de) | 2002-09-27 | 2010-08-04 | Merck Sharp & Dohme | Substituierte pyrimidine |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| GB0230088D0 (en) * | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| GB0302671D0 (en) * | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
| GB0302673D0 (en) * | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| GB0314049D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| WO2004111033A1 (en) * | 2003-06-18 | 2004-12-23 | Astrazeneca Ab | 2-substitued 5, 6-diaryl-pyrazine derivatives as cb1 modulator. |
| GB0314057D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0314261D0 (en) * | 2003-06-19 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| WO2005007628A1 (en) | 2003-07-11 | 2005-01-27 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
| US7326706B2 (en) * | 2003-08-15 | 2008-02-05 | Bristol-Myers Squibb Company | Pyrazine modulators of cannabinoid receptors |
| EP1663215A1 (de) * | 2003-09-02 | 2006-06-07 | Solvay Pharmaceuticals GmbH | Neue medizinische verwendung von selektiven cb1-rezeptorantagonisten |
| US7320805B2 (en) * | 2003-10-01 | 2008-01-22 | Institut National De La Sante Et De La Recherche Medicale | CB2 receptors blocks accumulation of human hepatic myofibroblasts: a novel artifibrogenic pathway in the liver |
| WO2005037199A2 (en) | 2003-10-10 | 2005-04-28 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
| CA2543197A1 (en) * | 2003-10-24 | 2005-05-06 | Solvay Pharmaceuticals Gmbh | Combination treatment of obesity involving selective cb1-antagonists and lipase inhibitors |
| TW200528102A (en) * | 2003-10-24 | 2005-09-01 | Solvay Pharm Gmbh | Novel medical combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| GB0327331D0 (en) * | 2003-11-25 | 2003-12-31 | Astrazeneca Ab | Therapeutic agents |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
| EP1807063A2 (de) | 2004-10-25 | 2007-07-18 | Solvay Pharmaceuticals GmbH | Pharmazeutische zusammensetzungen mit cb1 cannabinoid rezeptor-antagonisten und kaliumkanalöffner zur behandlung von diabetes mellitus vom typ i, fettsucht und verwandten erkrankungen |
| CA2602787C (en) | 2005-04-06 | 2013-12-24 | F. Hoffmann-La Roche Ag | Pyridine-3-carboxamide derivatives as cb1 inverse agonists |
| EP1871762A2 (de) * | 2005-04-18 | 2008-01-02 | Neurogen Corporation | Substituierte heteroaryle als cb1-antagonisten |
| MX2007016508A (es) | 2005-06-30 | 2008-03-04 | Prosidion Ltd | Agonistas del receptor acoplado a la proteina g. |
| US7629346B2 (en) | 2006-06-19 | 2009-12-08 | Hoffmann-La Roche Inc. | Pyrazinecarboxamide derivatives as CB1 antagonists |
| US7781593B2 (en) | 2006-09-14 | 2010-08-24 | Hoffmann-La Roche Inc. | 5-phenyl-nicotinamide derivatives |
| AU2007304365A1 (en) * | 2006-10-04 | 2008-04-10 | F. Hoffmann-La Roche Ag | 3-pyridinecarboxamide and 2-pyrazinecarboxamide derivatives as HDL-cholesterol raising agents |
| CA2674360A1 (en) | 2007-01-04 | 2008-07-10 | Prosidion Limited | Piperidine gpcr agonists |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| PE20081659A1 (es) | 2007-01-04 | 2008-10-24 | Prosidion Ltd | Agonistas de gpcr |
| AR064736A1 (es) | 2007-01-04 | 2009-04-22 | Prosidion Ltd | Agonistas de gpcr |
| US20100048632A1 (en) | 2007-01-04 | 2010-02-25 | Matthew Colin Thor Fyfe | Piperidine GPCR Agonists |
| GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
| GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
| WO2010079241A1 (es) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Uso de antagonistas y/o agonistas inversos de los receptores cb1 para la preparación de medicamentos que incrementen la excitabilidad de las motoneuronas |
| US8410107B2 (en) | 2010-10-15 | 2013-04-02 | Hoffmann-La Roche Inc. | N-pyridin-3-yl or N-pyrazin-2-yl carboxamides |
| US8669254B2 (en) | 2010-12-15 | 2014-03-11 | Hoffman-La Roche Inc. | Pyridine, pyridazine, pyrimidine or pyrazine carboxamides as HDL-cholesterol raising agents |
| US9403808B2 (en) * | 2011-10-28 | 2016-08-02 | Hoffmann-La Roche Inc. | Pyrazine derivatives |
| EP4192819A1 (de) | 2020-08-06 | 2023-06-14 | CHDI Foundation, Inc. | Heterobiarylverbindungen und abbildungsmittel zur abbildung von huntingtinprotein |
| WO2024159286A1 (pt) * | 2023-01-30 | 2024-08-08 | Eurofarma Laboratórios S.A. | Compostos fenólicos bloqueadores de nav 1.7 e/ou nav 1.8, seus processos de obtenção, composições, usos, métodos de tratamento destes e kits |
| WO2024159284A1 (pt) * | 2023-01-30 | 2024-08-08 | Eurofarma Laboratórios S.A. | Hidrazidas bloqueadoras de nav 1.7 e/ou nav 1.8, seus processos de obtenção, composições, usos, métodos de tratamento destes e kits |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH458361A (de) | 1965-01-15 | 1968-06-30 | Eprova Ag | Verfahren zur Herstellung von Pyrazincarbonsäuren |
| JPS5322529A (en) * | 1976-08-13 | 1978-03-02 | Nippon Soda Co Ltd | Dihydropyrazine derivative and its preparation |
| WO1989004308A1 (en) | 1987-11-12 | 1989-05-18 | Terumo Kabushiki Kaisha | Pyrazine derivatives and medicinal preparation containing same |
| JPH06501926A (ja) * | 1990-08-06 | 1994-03-03 | 藤沢薬品工業株式会社 | 複素環式化合物 |
| FR2713225B1 (fr) * | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
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2001
- 2001-12-19 SE SE0104330A patent/SE0104330D0/xx unknown
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2002
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- 2002-12-18 DE DE60218340T patent/DE60218340T2/de not_active Expired - Fee Related
- 2002-12-18 AT AT02788143T patent/ATE354570T1/de not_active IP Right Cessation
- 2002-12-18 JP JP2003552736A patent/JP2005517655A/ja active Pending
- 2002-12-18 ES ES02788143T patent/ES2280599T3/es not_active Expired - Lifetime
- 2002-12-18 KR KR10-2004-7009589A patent/KR20040068286A/ko not_active Application Discontinuation
- 2002-12-18 AU AU2002352425A patent/AU2002352425A1/en not_active Abandoned
- 2002-12-18 HU HU0402026A patent/HUP0402026A3/hu unknown
- 2002-12-18 NZ NZ533275A patent/NZ533275A/en unknown
- 2002-12-18 CN CNA028281535A patent/CN1620438A/zh active Pending
- 2002-12-18 PL PL02369731A patent/PL369731A1/xx not_active Application Discontinuation
- 2002-12-18 CA CA002469786A patent/CA2469786A1/en not_active Abandoned
- 2002-12-18 EP EP02788143A patent/EP1458690B1/de not_active Expired - Lifetime
- 2002-12-18 RU RU2004116916/04A patent/RU2004116916A/ru not_active Application Discontinuation
- 2002-12-18 MX MXPA04005990A patent/MXPA04005990A/es unknown
- 2002-12-18 BR BR0214989-3A patent/BR0214989A/pt not_active IP Right Cessation
- 2002-12-18 IL IL16237702A patent/IL162377A0/xx unknown
- 2002-12-19 AR ARP020105001A patent/AR038044A1/es not_active Application Discontinuation
- 2002-12-19 TW TW091136671A patent/TW200410694A/zh unknown
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2004
- 2004-06-16 IS IS7314A patent/IS7314A/is unknown
- 2004-06-17 ZA ZA200404805A patent/ZA200404805B/en unknown
- 2004-07-09 CO CO04065292A patent/CO5590917A2/es not_active Application Discontinuation
- 2004-07-15 NO NO20043022A patent/NO20043022L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
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| AU2002352425A1 (en) | 2003-06-30 |
| MXPA04005990A (es) | 2004-09-27 |
| ATE354570T1 (de) | 2007-03-15 |
| DE60218340D1 (de) | 2007-04-05 |
| AR038044A1 (es) | 2004-12-22 |
| CA2469786A1 (en) | 2003-06-26 |
| EP1458690B1 (de) | 2007-02-21 |
| HUP0402026A2 (hu) | 2005-02-28 |
| JP2005517655A (ja) | 2005-06-16 |
| EP1458690A1 (de) | 2004-09-22 |
| BR0214989A (pt) | 2004-12-14 |
| US7342019B2 (en) | 2008-03-11 |
| RU2004116916A (ru) | 2005-11-10 |
| IS7314A (is) | 2004-06-16 |
| CO5590917A2 (es) | 2005-12-30 |
| NO20043022L (no) | 2004-07-15 |
| DE60218340T2 (de) | 2007-11-29 |
| SE0104330D0 (sv) | 2001-12-19 |
| CN1620438A (zh) | 2005-05-25 |
| WO2003051851A1 (en) | 2003-06-26 |
| US20050032808A1 (en) | 2005-02-10 |
| PL369731A1 (en) | 2005-05-02 |
| NZ533275A (en) | 2006-02-24 |
| TW200410694A (en) | 2004-07-01 |
| IL162377A0 (en) | 2005-11-20 |
| ES2280599T3 (es) | 2007-09-16 |
| KR20040068286A (ko) | 2004-07-30 |
| HUP0402026A3 (en) | 2005-08-29 |
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