MXPA02002601A - Compuestos nuevos de isoindoloindolona, un proceso para su preparacion y composiciones farmaceuticas que los contienen. - Google Patents
Compuestos nuevos de isoindoloindolona, un proceso para su preparacion y composiciones farmaceuticas que los contienen.Info
- Publication number
- MXPA02002601A MXPA02002601A MXPA02002601A MXPA02002601A MXPA02002601A MX PA02002601 A MXPA02002601 A MX PA02002601A MX PA02002601 A MXPA02002601 A MX PA02002601A MX PA02002601 A MXPA02002601 A MX PA02002601A MX PA02002601 A MXPA02002601 A MX PA02002601A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- group
- carbon atoms
- branched
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 230000001193 melatoninergic effect Effects 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- APRMMGIMYPZNPC-UHFFFAOYSA-N 1,3-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound C12=CC=CC=C2C(=O)N2C1=CC1=C(OC)C=C(OC)C=C12 APRMMGIMYPZNPC-UHFFFAOYSA-N 0.000 claims description 2
- IRPIYZBBHNVOHO-UHFFFAOYSA-N 2-hydroxy-8,9-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C=C(C(=C4)OC)OC)=C4C3=CC2=C1 IRPIYZBBHNVOHO-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 7
- XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-N 0.000 description 6
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229960003987 melatonin Drugs 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000007170 pathology Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 208000019116 sleep disease Diseases 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- -1 5-Hydroxy-2-nitrobenzylidene Chemical group 0.000 description 3
- HWIZGBVJDMPJRO-UHFFFAOYSA-N 6-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C2COC(=O)C2=C1 HWIZGBVJDMPJRO-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- UNRFFBAJODEDDJ-UHFFFAOYSA-N C1=CC2=C3NC=CC3=CC=C2C2=C1C(=O)N=C2 Chemical compound C1=CC2=C3NC=CC3=CC=C2C2=C1C(=O)N=C2 UNRFFBAJODEDDJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 description 3
- 102000001419 Melatonin receptor Human genes 0.000 description 3
- 108050009605 Melatonin receptor Proteins 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- JBXRLVPILRXPNH-UHFFFAOYSA-N indol-6-one Chemical compound O=C1C=CC2=CC=NC2=C1 JBXRLVPILRXPNH-UHFFFAOYSA-N 0.000 description 3
- 206010022437 insomnia Diseases 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 208000012672 seasonal affective disease Diseases 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- UKFAWRZYFYOXEG-UHFFFAOYSA-N 5,6-dimethoxy-3H-isobenzofuran-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2 UKFAWRZYFYOXEG-UHFFFAOYSA-N 0.000 description 2
- PTWPWUVEQZXOFJ-UHFFFAOYSA-N 7-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2 PTWPWUVEQZXOFJ-UHFFFAOYSA-N 0.000 description 2
- 208000027559 Appetite disease Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 2
- FJDDSMSDZHURBJ-UHFFFAOYSA-N N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide Chemical compound COC1=CC=C2NC(I)=C(CCNC(C)=O)C2=C1 FJDDSMSDZHURBJ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 2
- 239000003446 ligand Substances 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000016087 ovulation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- WPRBUGIFHCMJKG-UHFFFAOYSA-N 16-hydroxy-5,7-dioxa-1-azapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2,4(8),9,11,13(18),14,16-heptaen-19-one Chemical compound C1=C2N3C(=O)C4=CC(O)=CC=C4C3=CC2=CC2=C1OCO2 WPRBUGIFHCMJKG-UHFFFAOYSA-N 0.000 description 1
- OWXQQVBJEAJOBD-UHFFFAOYSA-N 2,7,10-trihydroxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C(O)C2=C1C1=CC3=CC(O)=CC=C3N1C2=O OWXQQVBJEAJOBD-UHFFFAOYSA-N 0.000 description 1
- UFMFGBMKHDMOTF-UHFFFAOYSA-N 2,7-dihydroxy-10-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C(O)=CC=C4OC)=C4C3=CC2=C1 UFMFGBMKHDMOTF-UHFFFAOYSA-N 0.000 description 1
- RXDSFAJOOCXCSI-UHFFFAOYSA-N 2,7-dihydroxyisoindolo[2,3-a]indol-6-one Chemical compound C12=CC3=CC(O)=CC=C3N2C(=O)C2=C1C=CC=C2O RXDSFAJOOCXCSI-UHFFFAOYSA-N 0.000 description 1
- NNMPLRXTMYAJJC-UHFFFAOYSA-N 2,8-dihydroxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C4=CC(O)=CC=C4C3=CC2=C1 NNMPLRXTMYAJJC-UHFFFAOYSA-N 0.000 description 1
- WWOOPYFOUVESSA-UHFFFAOYSA-N 2,9-dihydroxy-8-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C=C(C(=C4)O)OC)=C4C3=CC2=C1 WWOOPYFOUVESSA-UHFFFAOYSA-N 0.000 description 1
- KXDDVYORMYPLOD-UHFFFAOYSA-N 2-hydroxy-10-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C=CC=C4OC)=C4C3=CC2=C1 KXDDVYORMYPLOD-UHFFFAOYSA-N 0.000 description 1
- SKHSZPJWOKSLCB-UHFFFAOYSA-N 2-hydroxy-7,10-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N(C(=O)C=3C(OC)=CC=C(OC)C=33)C3=CC2=C1 SKHSZPJWOKSLCB-UHFFFAOYSA-N 0.000 description 1
- QDMJNJFFOISCSD-UHFFFAOYSA-N 2-hydroxy-7,9-dimethyl-6-oxoisoindolo[2,1-a]indole-8-carboxylic acid Chemical compound OC1=CC=C2N(C(=O)C3=C4C=C(C(=C3C)C(O)=O)C)C4=CC2=C1 QDMJNJFFOISCSD-UHFFFAOYSA-N 0.000 description 1
- JGZQPIGFZOWNRX-UHFFFAOYSA-N 3-(2-formyl-3-nitrophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC([N+]([O-])=O)=C1C=O JGZQPIGFZOWNRX-UHFFFAOYSA-N 0.000 description 1
- PPJDXDBDZMZCJL-UHFFFAOYSA-N 3-benzyl-2-hydroxy-8,10-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound C1=2C(OC)=CC(OC)=CC=2C(=O)N(C2=C3)C1=CC2=CC(O)=C3CC1=CC=CC=C1 PPJDXDBDZMZCJL-UHFFFAOYSA-N 0.000 description 1
- HFWBBGYPGAWRIT-UHFFFAOYSA-N 4,7-dihydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C(O)C2=C1COC2=O HFWBBGYPGAWRIT-UHFFFAOYSA-N 0.000 description 1
- ABFJCCZUMNBAAI-UHFFFAOYSA-N 4,7-dimethoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(OC)C2=C1COC2=O ABFJCCZUMNBAAI-UHFFFAOYSA-N 0.000 description 1
- KWHZIUXAQFIEPP-UHFFFAOYSA-N 4-benzyl-5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=C([N+]([O-])=O)C=C1CC1=CC=CC=C1 KWHZIUXAQFIEPP-UHFFFAOYSA-N 0.000 description 1
- HTONKCSNONAUAZ-UHFFFAOYSA-N 4-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=CC2=C1COC2=O HTONKCSNONAUAZ-UHFFFAOYSA-N 0.000 description 1
- BNTDDWPHSMILHQ-UHFFFAOYSA-N 5-methoxy-2-nitrobenzaldehyde Chemical compound COC1=CC=C([N+]([O-])=O)C(C=O)=C1 BNTDDWPHSMILHQ-UHFFFAOYSA-N 0.000 description 1
- YEGQYRDJSUITQT-UHFFFAOYSA-N 6-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C2COC(=O)C2=C1 YEGQYRDJSUITQT-UHFFFAOYSA-N 0.000 description 1
- NRZWECORTTWSEF-UHFFFAOYSA-N 6-nitro-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC2=C1OCO2 NRZWECORTTWSEF-UHFFFAOYSA-N 0.000 description 1
- VBVSGUYGUBBWFG-UHFFFAOYSA-N 7-hydroxy-4-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(O)C2=C1COC2=O VBVSGUYGUBBWFG-UHFFFAOYSA-N 0.000 description 1
- KNYHQEDKIVXXOI-UHFFFAOYSA-N 8-hydroxy-2-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2C3=CC4=CC(OC)=CC=C4N3C(=O)C2=C1 KNYHQEDKIVXXOI-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000017164 Chronobiology disease Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000013200 Stress disease Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 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
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0103293A FR2821843B1 (fr) | 2001-03-12 | 2001-03-12 | Nouveaux derives d'isoindoloindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02002601A true MXPA02002601A (es) | 2004-11-12 |
Family
ID=8860976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02002601A MXPA02002601A (es) | 2001-03-12 | 2002-03-11 | Compuestos nuevos de isoindoloindolona, un proceso para su preparacion y composiciones farmaceuticas que los contienen. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6465660B1 (enExample) |
| EP (1) | EP1241169B1 (enExample) |
| JP (1) | JP3842151B2 (enExample) |
| KR (1) | KR100450313B1 (enExample) |
| CN (1) | CN1159316C (enExample) |
| AR (1) | AR034583A1 (enExample) |
| AT (1) | ATE248171T1 (enExample) |
| AU (1) | AU779702B2 (enExample) |
| BR (1) | BR0200721A (enExample) |
| CA (1) | CA2376876C (enExample) |
| DE (1) | DE60200023T2 (enExample) |
| DK (1) | DK1241169T3 (enExample) |
| EA (1) | EA004035B1 (enExample) |
| ES (1) | ES2206438T3 (enExample) |
| FR (1) | FR2821843B1 (enExample) |
| HK (1) | HK1049000B (enExample) |
| HU (1) | HUP0200913A3 (enExample) |
| MX (1) | MXPA02002601A (enExample) |
| NO (1) | NO20021198L (enExample) |
| NZ (1) | NZ517742A (enExample) |
| PL (1) | PL352750A1 (enExample) |
| PT (1) | PT1241169E (enExample) |
| SI (1) | SI1241169T1 (enExample) |
| ZA (1) | ZA200202030B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2826009B1 (fr) * | 2001-06-13 | 2003-08-15 | Servier Lab | Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1537113B9 (en) * | 2002-06-21 | 2010-05-26 | Suven Life Sciences Limited | Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| CA2490002C (en) * | 2002-06-21 | 2009-07-07 | Suven Life Sciences Limited | Novel tetracyclic arylcarbonyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| ES2425143T3 (es) * | 2002-11-28 | 2013-10-11 | Suven Life Sciences Limited | N-Arilsulfonil-3-aminoalcoxiindoles |
| KR100739987B1 (ko) * | 2002-12-18 | 2007-07-16 | 수벤 라이프 사이언시스 리미티드 | 세로토닌 수용체 친화력을 가지는 테트라사이클릭 3-치환인돌 |
| RU2387655C2 (ru) * | 2004-08-09 | 2010-04-27 | Бристол-Маерс Сквибб Компани | Ингибиторы репликации вируса гепатита с |
| ES2580702B1 (es) | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| JP2025530666A (ja) | 2022-09-02 | 2025-09-17 | デックスコム・インコーポレーテッド | 連続分析物センサデバイス及び方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5377098A (en) * | 1976-12-16 | 1978-07-08 | Sumitomo Chem Co Ltd | Preparation of indoloisoquinoline derivative |
| US4452808A (en) * | 1982-12-07 | 1984-06-05 | Smithkline Beckman Corporation | 4-Aminoalkyl-2(3H)-indolones |
| US5441955A (en) * | 1993-11-19 | 1995-08-15 | Pathogenesis Corporation | Indolo[2,1-biquinazoline-6,12-dione antibacterial compounds and methods of use thereof |
| FR2743365A1 (fr) * | 1996-01-10 | 1997-07-11 | Rhone Poulenc Rorer Sa | Derives de 5h,10h-imidazo(1,2-a)indolo(3,2-e)pyrazine-4-one, leur preparation et les medicaments les contenant |
| US20020040018A1 (en) * | 2000-06-23 | 2002-04-04 | Jones Robert M. | Subtype selective melatonergics |
-
2001
- 2001-03-12 FR FR0103293A patent/FR2821843B1/fr not_active Expired - Fee Related
-
2002
- 2002-02-26 US US10/083,074 patent/US6465660B1/en not_active Expired - Fee Related
- 2002-03-09 KR KR10-2002-0012699A patent/KR100450313B1/ko not_active Expired - Fee Related
- 2002-03-11 CA CA002376876A patent/CA2376876C/fr not_active Expired - Fee Related
- 2002-03-11 PT PT02290598T patent/PT1241169E/pt unknown
- 2002-03-11 NZ NZ517742A patent/NZ517742A/xx unknown
- 2002-03-11 ES ES02290598T patent/ES2206438T3/es not_active Expired - Lifetime
- 2002-03-11 NO NO20021198A patent/NO20021198L/no not_active Application Discontinuation
- 2002-03-11 EA EA200200241A patent/EA004035B1/ru unknown
- 2002-03-11 JP JP2002065233A patent/JP3842151B2/ja not_active Expired - Fee Related
- 2002-03-11 AR ARP020100863A patent/AR034583A1/es active IP Right Grant
- 2002-03-11 SI SI200230002T patent/SI1241169T1/xx unknown
- 2002-03-11 AT AT02290598T patent/ATE248171T1/de not_active IP Right Cessation
- 2002-03-11 MX MXPA02002601A patent/MXPA02002601A/es active IP Right Grant
- 2002-03-11 HU HU0200913A patent/HUP0200913A3/hu unknown
- 2002-03-11 DE DE60200023T patent/DE60200023T2/de not_active Expired - Fee Related
- 2002-03-11 BR BR0200721-5A patent/BR0200721A/pt not_active IP Right Cessation
- 2002-03-11 DK DK02290598T patent/DK1241169T3/da active
- 2002-03-11 EP EP02290598A patent/EP1241169B1/fr not_active Expired - Lifetime
- 2002-03-12 CN CNB021070547A patent/CN1159316C/zh not_active Expired - Fee Related
- 2002-03-12 AU AU23242/02A patent/AU779702B2/en not_active Ceased
- 2002-03-12 PL PL02352750A patent/PL352750A1/xx not_active Application Discontinuation
- 2002-03-12 ZA ZA200202030A patent/ZA200202030B/xx unknown
-
2003
- 2003-02-18 HK HK03101182.3A patent/HK1049000B/zh not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5639778A (en) | Indoletetralins having dopaminergic activity | |
| JPWO1998030548A1 (ja) | ５−ＨＴ▲下２ｃ▼受容体作用薬及びアミノアルキルインダゾール誘導体 | |
| CN101970436A (zh) | 用于治疗中枢神经系统功能障碍的氮杂吲哚化合物 | |
| HU211928A9 (en) | Therapeutically useful 2-aminotetraline derivatives | |
| MXPA02002601A (es) | Compuestos nuevos de isoindoloindolona, un proceso para su preparacion y composiciones farmaceuticas que los contienen. | |
| JP3886829B2 (ja) | 新規インデノインドロン化合物、それらの調製方法およびそれらを含む医薬組成物 | |
| AU755115B2 (en) | New cyclic compounds having a cycloalkylene chain, a process for their preparation and pharmaceutical compositions containing them | |
| JP2008013558A (ja) | 新規ナフタレン化合物、その製造法、およびそれを含有する薬学的組成物 | |
| KR20100029262A (ko) | 나프탈렌 유도체，이의 제조 방법 및 이를 함유하는 약제학적 조성물 | |
| CA2157586C (en) | Indoletetralins having dopaminergic activity | |
| ZA200503232B (en) | Novel phenylnapthalene derivatives, method for production thereof and pharmaceutical compositions comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |