PL207047B1 - Nowe związki pirymidyn-4-onu i zawierające je kompozycje farmaceutyczne - Google Patents
Nowe związki pirymidyn-4-onu i zawierające je kompozycje farmaceutyczneInfo
- Publication number
- PL207047B1 PL207047B1 PL353511A PL35351102A PL207047B1 PL 207047 B1 PL207047 B1 PL 207047B1 PL 353511 A PL353511 A PL 353511A PL 35351102 A PL35351102 A PL 35351102A PL 207047 B1 PL207047 B1 PL 207047B1
- Authority
- PL
- Poland
- Prior art keywords
- methyl
- pyrimidin
- pharmaceutically acceptable
- enantiomers
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 88
- 238000000034 method Methods 0.000 title description 33
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title description 4
- 239000008196 pharmacological composition Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 46
- -1 ethylene, propylene Chemical group 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 24
- 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 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 206010021567 Impulsive behaviour Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000009977 dual effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002484 serotonin 2C antagonist Substances 0.000 claims description 2
- 230000001568 sexual effect Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 97
- 239000000047 product Substances 0.000 description 78
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000001530 fumaric acid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- LFTGLYCNMGGMKL-UHFFFAOYSA-N 3-(2-chloroethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C(CCCl)=C(C)N=C21 LFTGLYCNMGGMKL-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JLHJDRRHYSSWNV-UHFFFAOYSA-N chromeno[3,4-c]pyrrole Chemical compound C1=CC=C2C3=CN=CC3=COC2=C1 JLHJDRRHYSSWNV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- OLZHNYYHNUUTJS-UHFFFAOYSA-N 3-(2-chloroethyl)-2-methylpyridine Chemical compound CC1=NC=CC=C1CCCl OLZHNYYHNUUTJS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003291 dopaminomimetic effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000018052 penile erection Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- UUXFTJCUPHVPKZ-UHFFFAOYSA-N 2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CC2=NC(C)=CC(=O)N21 UUXFTJCUPHVPKZ-UHFFFAOYSA-N 0.000 description 2
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 2
- SVZSNASRUSJMAF-UHFFFAOYSA-N 6-(2-chloroethyl)-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C(CCCl)=C(C)N=C2SC=CN21 SVZSNASRUSJMAF-UHFFFAOYSA-N 0.000 description 2
- VJCBSGFUBYWQPL-UHFFFAOYSA-N 7-chloro-3-(2-chloroethyl)-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(Cl)=CN2C(=O)C(CCCl)=C(C)N=C21 VJCBSGFUBYWQPL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102000007527 Autoreceptors Human genes 0.000 description 2
- 108010071131 Autoreceptors Proteins 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920005372 Plexiglas® Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-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
- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000009933 burial Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002474 noradrenergic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002485 serotonin 2C agonist Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FJCAHIFUCPXKCU-UHFFFAOYSA-N 1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole Chemical class C1=CC=C2C3CNCC3COC2=C1 FJCAHIFUCPXKCU-UHFFFAOYSA-N 0.000 description 1
- CQMJEZQEVXQEJB-UHFFFAOYSA-N 1-hydroxy-1,3-dioxobenziodoxole Chemical compound C1=CC=C2I(O)(=O)OC(=O)C2=C1 CQMJEZQEVXQEJB-UHFFFAOYSA-N 0.000 description 1
- TTWAXOWGLOFVPH-UHFFFAOYSA-N 11-oxa-15-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8-pentaene Chemical compound C1=CC=CC2=C3C4CNCC4COC3=CC=C21 TTWAXOWGLOFVPH-UHFFFAOYSA-N 0.000 description 1
- YONLFQNRGZXBBF-UHFFFAOYSA-N 2,3-dibenzoyloxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-UHFFFAOYSA-N 0.000 description 1
- OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 description 1
- UOKAZUWUHOBBMD-UHFFFAOYSA-N 2,4-dimethoxy-3-methylbenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1C UOKAZUWUHOBBMD-UHFFFAOYSA-N 0.000 description 1
- FMFMDOJFLHYBOM-UHFFFAOYSA-N 2,4-dimethoxy-3-methylphenol Chemical compound COC1=CC=C(O)C(OC)=C1C FMFMDOJFLHYBOM-UHFFFAOYSA-N 0.000 description 1
- AJDRPKLJHXSPKR-UHFFFAOYSA-N 2-(7-chloro-2-methyl-4-oxopyrido[1,2-a]pyrimidin-3-yl)acetaldehyde Chemical compound C1=CC(Cl)=CN2C(=O)C(CC=O)=C(C)N=C21 AJDRPKLJHXSPKR-UHFFFAOYSA-N 0.000 description 1
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- WTAHIERDSNGTGY-UHFFFAOYSA-N 3-(2-chloroethyl)-2,7-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=C(CCCl)C(=O)N2C=C(C)C=CC2=N1 WTAHIERDSNGTGY-UHFFFAOYSA-N 0.000 description 1
- JSGVKYMZIXIAJN-UHFFFAOYSA-N 3-(2-chloroethyl)-2-methyl-7-thiophen-2-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C(CCCl)=C(C)N=C2C=CC=1C1=CC=CS1 JSGVKYMZIXIAJN-UHFFFAOYSA-N 0.000 description 1
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- 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
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0105216A FR2823752B1 (fr) | 2001-04-18 | 2001-04-18 | Nouveaux derives de pyrimidin-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL353511A1 PL353511A1 (en) | 2002-10-21 |
| PL207047B1 true PL207047B1 (pl) | 2010-10-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL353511A PL207047B1 (pl) | 2001-04-18 | 2002-04-18 | Nowe związki pirymidyn-4-onu i zawierające je kompozycje farmaceutyczne |
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| PT (1) | PT1256583E (cg-RX-API-DMAC7.html) |
| SI (1) | SI1256583T1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200203086B (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8349850B2 (en) * | 2006-03-28 | 2013-01-08 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| EP3581567A1 (en) | 2011-04-10 | 2019-12-18 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| JP2016509066A (ja) * | 2013-02-22 | 2016-03-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アダプター関連キナーゼ１（ａａｋ１）の阻害剤としての５ｈ−クロメノ［３，４−ｃ］ピリジン |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2722194B1 (fr) * | 1994-07-06 | 1996-08-23 | Adir | Nouveaux derives de benzopyrane, leur procede de preparation et les compositions pharmacuetiques qui les contiennent |
| FR2764890B1 (fr) * | 1997-06-24 | 1999-08-27 | Adir | Nouveaux derives chromeniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU1481701A (en) | 1999-11-12 | 2001-06-06 | Neurogen Corporation | Bicyclic and tricyclic heteroaromatic compounds |
-
2001
- 2001-04-18 FR FR0105216A patent/FR2823752B1/fr not_active Expired - Lifetime
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2002
- 2002-04-16 DK DK02290945T patent/DK1256583T3/da active
- 2002-04-16 ES ES02290945T patent/ES2246380T3/es not_active Expired - Lifetime
- 2002-04-16 EP EP02290945A patent/EP1256583B1/fr not_active Expired - Lifetime
- 2002-04-16 AT AT02290945T patent/ATE301662T1/de not_active IP Right Cessation
- 2002-04-16 PT PT02290945T patent/PT1256583E/pt unknown
- 2002-04-16 DE DE60205424T patent/DE60205424T2/de not_active Expired - Lifetime
- 2002-04-16 SI SI200230180T patent/SI1256583T1/sl unknown
- 2002-04-17 NO NO20021806A patent/NO328014B1/no not_active IP Right Cessation
- 2002-04-17 MX MXPA02003849A patent/MXPA02003849A/es active IP Right Grant
- 2002-04-17 HU HU0201255A patent/HUP0201255A3/hu unknown
- 2002-04-17 AR ARP020101385A patent/AR034308A1/es unknown
- 2002-04-17 EA EA200200379A patent/EA005402B1/ru not_active IP Right Cessation
- 2002-04-17 JP JP2002114443A patent/JP3781698B2/ja not_active Expired - Fee Related
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- 2002-04-18 CN CNB021161038A patent/CN1181075C/zh not_active Expired - Fee Related
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- 2002-04-18 AU AU34406/02A patent/AU781663B2/en not_active Ceased
- 2002-04-18 CA CA002383315A patent/CA2383315C/fr not_active Expired - Fee Related
- 2002-04-18 BR BR0201312-6A patent/BR0201312A/pt not_active IP Right Cessation
- 2002-04-18 US US10/125,188 patent/US6747032B2/en not_active Expired - Fee Related
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Effective date: 20110418 |