MXPA06013939A - Compuestos pirimidina y uso de los mismos. - Google Patents
Compuestos pirimidina y uso de los mismos.Info
- Publication number
- MXPA06013939A MXPA06013939A MXPA06013939A MXPA06013939A MXPA06013939A MX PA06013939 A MXPA06013939 A MX PA06013939A MX PA06013939 A MXPA06013939 A MX PA06013939A MX PA06013939 A MXPA06013939 A MX PA06013939A MX PA06013939 A MXPA06013939 A MX PA06013939A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- butyl
- compound
- formula
- group
- Prior art date
Links
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 208000035475 disorder Diseases 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 12
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 2
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 2
- 229910020008 S(O) Inorganic materials 0.000 abstract 2
- 150000000564 5-membered carbocyclic compounds Chemical class 0.000 abstract 1
- 150000000643 6-membered carbocyclic compounds Chemical class 0.000 abstract 1
- 150000000659 7-membered carbocyclic compounds Chemical class 0.000 abstract 1
- 229940088353 Dopamine D3 receptor antagonist Drugs 0.000 abstract 1
- 229940052760 dopamine agonists Drugs 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 239000000018 receptor agonist Substances 0.000 abstract 1
- -1 aromatic sulfonic acids Chemical class 0.000 description 135
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 86
- 238000000034 method Methods 0.000 description 79
- 239000000203 mixture Substances 0.000 description 63
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 28
- 102000005962 receptors Human genes 0.000 description 25
- 108020003175 receptors Proteins 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 24
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 239000011734 sodium Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 239000003446 ligand Substances 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- BTAKRXXDPHBOAH-UHFFFAOYSA-N 2-tert-butyl-4-piperazin-1-yl-6-propylpyrimidine Chemical compound CC(C)(C)C1=NC(CCC)=CC(N2CCNCC2)=N1 BTAKRXXDPHBOAH-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052701 rubidium Inorganic materials 0.000 description 7
- NNUWYOHBJUOVBC-UHFFFAOYSA-N 1,3-dihydroquinoline-2,5-dione Chemical compound O=C1C=CC=C2NC(=O)CC=C21 NNUWYOHBJUOVBC-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 6
- 229960003638 dopamine Drugs 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 208000028017 Psychotic disease Diseases 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000002274 desiccant Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000004064 dysfunction Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VVXWGLZAKGMQGQ-UHFFFAOYSA-N 1-(4-chlorobutyl)-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CCCCCl)C(=O)CCC2=C1 VVXWGLZAKGMQGQ-UHFFFAOYSA-N 0.000 description 4
- DPHUYVAPOOTEHI-UHFFFAOYSA-N 1-(4-chlorobutyl)-5-methoxy-3,4-dihydroquinolin-2-one Chemical compound ClCCCCN1C(=O)CCC2=C1C=CC=C2OC DPHUYVAPOOTEHI-UHFFFAOYSA-N 0.000 description 4
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 102000015554 Dopamine receptor Human genes 0.000 description 4
- 108050004812 Dopamine receptor Proteins 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 230000003907 kidney function Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- SJUMAAKSTCLCHF-UHFFFAOYSA-N 1-(4-bromobutyl)-4,5-dihydro-3h-1-benzazepin-2-one Chemical compound C1CCC(=O)N(CCCCBr)C2=CC=CC=C21 SJUMAAKSTCLCHF-UHFFFAOYSA-N 0.000 description 3
- BVLPMFKIWBUZJJ-UHFFFAOYSA-N 1-(4-chlorobutyl)quinolin-2-one Chemical compound C1=CC=C2C=CC(=O)N(CCCCCl)C2=C1 BVLPMFKIWBUZJJ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OYWWAAYLBUINTG-UHFFFAOYSA-N 5-chloro-1-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)pentan-1-one Chemical compound ClCCCCC(=O)N1CCCCC2=CC=CC=C12 OYWWAAYLBUINTG-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 101150049660 DRD2 gene Proteins 0.000 description 3
- 101150097070 Drd3 gene Proteins 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 101150026303 HEX1 gene Proteins 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 208000019022 Mood disease Diseases 0.000 description 3
- 206010029333 Neurosis Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 208000027520 Somatoform disease Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 239000000164 antipsychotic agent Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229960003920 cocaine Drugs 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 208000015238 neurotic disease Diseases 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000000506 psychotropic effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RRUVZSXVFFLOAR-UHFFFAOYSA-N 1-(4-bromobutyl)-4,6,7,8-tetrahydro-3h-quinoline-2,5-dione Chemical compound C1CCC(=O)C2=C1N(CCCCBr)C(=O)CC2 RRUVZSXVFFLOAR-UHFFFAOYSA-N 0.000 description 2
- HRQNRAJDTUWQFJ-UHFFFAOYSA-N 1-(4-bromobutyl)-5-ethoxy-3,4-dihydroquinolin-2-one Chemical compound BrCCCCN1C(=O)CCC2=C1C=CC=C2OCC HRQNRAJDTUWQFJ-UHFFFAOYSA-N 0.000 description 2
- MGXIFCBKMYGLKL-UHFFFAOYSA-N 1-(4-bromobutyl)-5-methoxy-3,4-dihydroquinolin-2-one Chemical compound BrCCCCN1C(=O)CCC2=C1C=CC=C2OC MGXIFCBKMYGLKL-UHFFFAOYSA-N 0.000 description 2
- FFODSPIOAXWQRY-UHFFFAOYSA-N 1-(4-bromopentyl)-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CCCC(Br)C)C(=O)CCC2=C1 FFODSPIOAXWQRY-UHFFFAOYSA-N 0.000 description 2
- QYGMYJVRBDDWNP-UHFFFAOYSA-N 1-(4-chlorobutyl)-6-methoxy-3,4-dihydroquinolin-2-one Chemical compound ClCCCCN1C(=O)CCC2=CC(OC)=CC=C21 QYGMYJVRBDDWNP-UHFFFAOYSA-N 0.000 description 2
- ZJWMQACOHZHITH-UHFFFAOYSA-N 1-(4-chlorobutyl)-7-methoxy-3,4-dihydroquinolin-2-one Chemical compound C1CC(=O)N(CCCCCl)C2=CC(OC)=CC=C21 ZJWMQACOHZHITH-UHFFFAOYSA-N 0.000 description 2
- ICRPRJFRUCIUIH-UHFFFAOYSA-N 1-(4-chlorobutyl)-8-methoxy-3,4-dihydroquinolin-2-one Chemical compound C1CC(=O)N(CCCCCl)C2=C1C=CC=C2OC ICRPRJFRUCIUIH-UHFFFAOYSA-N 0.000 description 2
- IUAAPKJCPNRSAV-UHFFFAOYSA-N 1-(4-chlorobutyl)-8-methyl-3,4-dihydroquinolin-2-one Chemical compound C1CC(=O)N(CCCCCl)C2=C1C=CC=C2C IUAAPKJCPNRSAV-UHFFFAOYSA-N 0.000 description 2
- UYRPTUWFLRHNJX-UHFFFAOYSA-N 1-[4-[4-(2-tert-butyl-6-propylpyrimidin-4-yl)piperazin-1-yl]butyl]-4,5-dihydro-3h-1-benzazepin-2-one Chemical compound CC(C)(C)C1=NC(CCC)=CC(N2CCN(CCCCN3C(CCCC4=CC=CC=C43)=O)CC2)=N1 UYRPTUWFLRHNJX-UHFFFAOYSA-N 0.000 description 2
- IBIBSYDJDFNPPK-UHFFFAOYSA-N 1-[4-[4-(2-tert-butyl-6-propylpyrimidin-4-yl)piperazin-1-yl]butyl]-5-ethoxy-3,4-dihydroquinolin-2-one Chemical compound CC(C)(C)C1=NC(CCC)=CC(N2CCN(CCCCN3C4=CC=CC(OCC)=C4CCC3=O)CC2)=N1 IBIBSYDJDFNPPK-UHFFFAOYSA-N 0.000 description 2
- LRTWYJMSDIOBGF-UHFFFAOYSA-N 1-[4-[4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl]butyl]quinolin-2-one Chemical compound FC(F)(F)C1=NC(C(C)(C)C)=NC(N2CCN(CCCCN3C(C=CC4=CC=CC=C43)=O)CC2)=C1 LRTWYJMSDIOBGF-UHFFFAOYSA-N 0.000 description 2
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004027358A DE102004027358A1 (de) | 2004-06-04 | 2004-06-04 | Pyrimidinverbindungen und ihre Verwendung |
| PCT/EP2005/006000 WO2005118558A2 (de) | 2004-06-04 | 2005-06-03 | Pyrimidinverbindungen und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06013939A true MXPA06013939A (es) | 2007-08-14 |
Family
ID=35134083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06013939A MXPA06013939A (es) | 2004-06-04 | 2005-06-03 | Compuestos pirimidina y uso de los mismos. |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7786105B2 (enExample) |
| EP (2) | EP1751116B1 (enExample) |
| JP (1) | JP5503845B2 (enExample) |
| CA (1) | CA2567484C (enExample) |
| DE (1) | DE102004027358A1 (enExample) |
| MX (1) | MXPA06013939A (enExample) |
| WO (1) | WO2005118558A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10259382A1 (de) * | 2002-12-18 | 2004-07-01 | Abbott Gmbh & Co. Kg | 3-Substituierte 3,4-Dihydro-thieno[2,3-d]pyrimidin-4-on-Derivate, ihre Herstellung und Verwendung |
| US20040204422A1 (en) | 2003-04-14 | 2004-10-14 | Abbott Gmbh & Co. Kg. | N-[(Piperazinyl)hetaryl]arylsulfonamide compounds |
| PA8802101A1 (es) | 2007-11-02 | 2009-08-26 | Abbott Gmbh & Co Kg | Compuestos de 1,2,4-3,5-diona adecuados para el tratamiento de trastornos que responden a la modulación del receptor de dopamina d3 |
| US9376396B2 (en) | 2012-10-22 | 2016-06-28 | AbbVie Deutschland GmbH & Co. KG | Acylaminocycloalkyl compounds suitable for treating disorders that respond to modulation of dopamine D3 receptor |
| AR095264A1 (es) | 2013-03-15 | 2015-09-30 | Abbvie Deutschland | Compuestos de acilaminocicloalquilo apropiados para tratar trastornos que responden a la modulación del receptor de dopamina d3 |
| UY35420A (es) | 2013-03-15 | 2014-10-31 | Abbvie Inc | Compuestos de acilaminocicloalquilo apropiados para tratar trastornos que responden a la modulación del receptor de dopamina d3 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62257158A (ja) | 1986-04-30 | 1987-11-09 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| DE3800386A1 (de) | 1988-01-09 | 1989-07-20 | Bayer Ag | Verfahren zur herstellung von benzothiazepinon-derivaten |
| DE4425146A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| DE4425145A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung von Thiazol- und Thiadiazolverbindungen |
| DE4425144A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
| DE4425143A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Substituierte Pyrimidinverbindungen und deren Verwendung |
| DE19600934A1 (de) | 1996-01-12 | 1997-07-17 | Basf Ag | Substituierte Aza- und Diazacycloheptan- und Cyclooctanverbindungen und deren Verwendung |
| DE19728996A1 (de) | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
| DE19735410A1 (de) | 1997-08-14 | 1999-02-18 | Basf Ag | 2-{3-[4-(2-t-Butyl-6-trifluormethylpyrimidin-4-yl)piperazin-1-yl]propylmercapto}pyrimidin-4-ol-fumarat |
| CN1293669A (zh) * | 1998-02-26 | 2001-05-02 | 纽罗根公司 | 苄基哌嗪基－和苄基哌啶基－乙酮衍生物、其制备方法及其用作多巴胺d 受体拮抗剂的用途 |
| TWI274750B (en) | 1999-01-12 | 2007-03-01 | Abbott Gmbh & Co Kg | Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same |
| DE19922443A1 (de) | 1999-05-07 | 2000-11-09 | Basf Ag | Verwendung von Dopamin-D3-Rezeptorliganden zur Herstellung von Arzneimittel für die Behandlung von Nierenfunktionsstörungen |
| EP1246817B1 (en) | 1999-12-30 | 2004-06-23 | H. Lundbeck A/S | 4-phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives |
| HUP0300786A2 (hu) | 2000-06-29 | 2003-07-28 | H. Lundbeck A/S | A központi idegrendszer megbetegedéseinek kezelésére alkalmas indolszármazékok és ezeket tartalmazó gyógyszerkészítmények |
| DE10304870A1 (de) | 2003-02-06 | 2004-08-19 | Abbott Gmbh & Co. Kg | Triazolverbindungen und ihre therapeutische Verwendung |
-
2004
- 2004-06-04 DE DE102004027358A patent/DE102004027358A1/de not_active Withdrawn
-
2005
- 2005-06-03 EP EP05750829.3A patent/EP1751116B1/de not_active Expired - Lifetime
- 2005-06-03 JP JP2007513870A patent/JP5503845B2/ja not_active Expired - Fee Related
- 2005-06-03 US US11/628,658 patent/US7786105B2/en not_active Expired - Fee Related
- 2005-06-03 CA CA2567484A patent/CA2567484C/en not_active Expired - Fee Related
- 2005-06-03 EP EP11167864A patent/EP2361908A1/de not_active Withdrawn
- 2005-06-03 MX MXPA06013939A patent/MXPA06013939A/es active IP Right Grant
- 2005-06-03 WO PCT/EP2005/006000 patent/WO2005118558A2/de not_active Ceased
-
2010
- 2010-07-23 US US12/842,776 patent/US8268815B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7786105B2 (en) | 2010-08-31 |
| US8268815B2 (en) | 2012-09-18 |
| JP5503845B2 (ja) | 2014-05-28 |
| CA2567484C (en) | 2012-10-30 |
| EP1751116A2 (de) | 2007-02-14 |
| JP2008501662A (ja) | 2008-01-24 |
| DE102004027358A1 (de) | 2005-12-29 |
| CA2567484A1 (en) | 2005-12-15 |
| EP1751116B1 (de) | 2013-07-31 |
| US20080161322A1 (en) | 2008-07-03 |
| WO2005118558A2 (de) | 2005-12-15 |
| US20110118232A1 (en) | 2011-05-19 |
| WO2005118558A3 (de) | 2006-02-09 |
| EP2361908A1 (de) | 2011-08-31 |
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