KR20070062609A - 5-ｈｔ2ｃ 아고니스트로서의 피롤로인돌, 피리도인돌 및아제피노인돌 - Google Patents
5-ｈｔ2ｃ 아고니스트로서의 피롤로인돌, 피리도인돌 및아제피노인돌 Download PDFInfo
- Publication number
- KR20070062609A KR20070062609A KR1020077011961A KR20077011961A KR20070062609A KR 20070062609 A KR20070062609 A KR 20070062609A KR 1020077011961 A KR1020077011961 A KR 1020077011961A KR 20077011961 A KR20077011961 A KR 20077011961A KR 20070062609 A KR20070062609 A KR 20070062609A
- Authority
- KR
- South Korea
- Prior art keywords
- pyrrolo
- pharmaceutical composition
- dihydro
- carboxaldehyde
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000556 agonist Substances 0.000 title description 5
- NJBMMMJOXRZENQ-UHFFFAOYSA-N 6H-pyrrolo[2,3-f]quinoline Chemical compound c1cc2ccc3[nH]cccc3c2n1 NJBMMMJOXRZENQ-UHFFFAOYSA-N 0.000 title description 2
- ZCOSUVZGFDGWFV-UHFFFAOYSA-N pyrrolo[2,3-e]indole Chemical compound C1=CC2=NC=CC2=C2N=CC=C21 ZCOSUVZGFDGWFV-UHFFFAOYSA-N 0.000 title description 2
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 title 1
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000003542 behavioural effect Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- AYNAVHUTXWVDLR-UHFFFAOYSA-N 1-(6,7-difluoro-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound C12=CC(F)=C(F)C=C2C(CC(N)C)=C2N1CCC2 AYNAVHUTXWVDLR-UHFFFAOYSA-N 0.000 claims description 2
- VCCGTYYMZYICBO-UHFFFAOYSA-N 1-(6-bromo-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound C12=CC=C(Br)C=C2C(CC(N)C)=C2N1CCC2 VCCGTYYMZYICBO-UHFFFAOYSA-N 0.000 claims description 2
- XNFYXIJQNZVXAX-UHFFFAOYSA-N 1-(6-chloro-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound C12=CC=C(Cl)C=C2C(CC(N)C)=C2N1CCC2 XNFYXIJQNZVXAX-UHFFFAOYSA-N 0.000 claims description 2
- YVXUJNPXVWMCCZ-UHFFFAOYSA-N 1-(6-methoxy-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound COC1=CC=C2N(CCC3)C3=C(CC(C)N)C2=C1 YVXUJNPXVWMCCZ-UHFFFAOYSA-N 0.000 claims description 2
- SPMDNODKUUODIS-UHFFFAOYSA-N 1-(6-methylsulfanyl-2,3-dihydro-1h-pyrrolo[1,2-a]indol-4-yl)propan-2-amine Chemical compound CSC1=CC=C2N(CCC3)C3=C(CC(C)N)C2=C1 SPMDNODKUUODIS-UHFFFAOYSA-N 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000002458 infectious effect Effects 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 206010001488 Aggression Diseases 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010063659 Aversion Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000027626 Neurocognitive disease Diseases 0.000 claims 1
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000025748 atypical depressive disease Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- 206010016256 fatigue Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000000484 premenstrual tension Diseases 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 230000002885 thrombogenetic effect Effects 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- -1 arylsuloxy Chemical group 0.000 abstract description 60
- 208000008589 Obesity Diseases 0.000 abstract description 15
- 235000020824 obesity Nutrition 0.000 abstract description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 6
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 abstract description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract description 4
- 125000005110 aryl thio group Chemical group 0.000 abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- 239000000651 prodrug Substances 0.000 abstract description 4
- 229940002612 prodrug Drugs 0.000 abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 3
- 208000003417 Central Sleep Apnea Diseases 0.000 abstract 1
- 239000000047 product Substances 0.000 description 69
- 238000000034 method Methods 0.000 description 66
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 54
- 239000007787 solid Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 238000002844 melting Methods 0.000 description 44
- 230000008018 melting Effects 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 102000005962 receptors Human genes 0.000 description 18
- 108020003175 receptors Proteins 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 13
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 10
- 238000012986 modification Methods 0.000 description 10
- 230000004048 modification Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910004298 SiO 2 Inorganic materials 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 7
- TUWARWGEOHQXCO-UHFFFAOYSA-N 5-methoxyindole-3-carbaldehyde Chemical compound COC1=CC=C2NC=C(C=O)C2=C1 TUWARWGEOHQXCO-UHFFFAOYSA-N 0.000 description 7
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 7
- 239000005695 Ammonium acetate Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000005909 Kieselgur Substances 0.000 description 7
- 235000019257 ammonium acetate Nutrition 0.000 description 7
- 229940043376 ammonium acetate Drugs 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 239000011541 reaction mixture Substances 0.000 description 7
- PEENKJZANBYXNB-UHFFFAOYSA-N 5-bromo-1h-indole-3-carbaldehyde Chemical compound BrC1=CC=C2NC=C(C=O)C2=C1 PEENKJZANBYXNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 239000000883 anti-obesity agent Substances 0.000 description 5
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- 239000012043 crude product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241000699802 Cricetulus griseus Species 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 238000007796 conventional method Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 3
- MSYJFNQAVTYKOP-UHFFFAOYSA-N 4-chloro-1h-indole-3-carbaldehyde Chemical compound ClC1=CC=CC2=C1C(C=O)=CN2 MSYJFNQAVTYKOP-UHFFFAOYSA-N 0.000 description 3
- JVFNNILBFBSJLA-UHFFFAOYSA-N 5,6-difluoro-1h-indole-3-carbaldehyde Chemical compound C1=C(F)C(F)=CC2=C1C(C=O)=CN2 JVFNNILBFBSJLA-UHFFFAOYSA-N 0.000 description 3
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 3
- DJGNUBADRQIDNQ-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole-3-carbaldehyde Chemical compound C1=C2C(C=O)=CNC2=CC=C1OCC1=CC=CC=C1 DJGNUBADRQIDNQ-UHFFFAOYSA-N 0.000 description 3
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- 150000007513 acids Chemical class 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
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Classifications
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- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Neurology (AREA)
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- Diabetes (AREA)
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- Cardiology (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9819035.8A GB9819035D0 (en) | 1998-09-01 | 1998-09-01 | Chemical compounds VII |
| GB9819035.8 | 1998-09-01 |
Related Parent Applications (1)
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| GB9918965D0 (en) | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxi |
| US6818639B2 (en) | 2000-07-21 | 2004-11-16 | Biovitrum Ab | Pharmaceutical combination formulation and method of treatment with the combination |
| SE0002754D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New pharmaceutical combination formulation and method of treatment with the combination |
| WO2002040457A1 (en) | 2000-11-20 | 2002-05-23 | Biovitrum Ab | Piperazinylpyrazines compounds as antagonists of serotonin 5-ht2 receptor |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| JP2005506280A (ja) | 2000-12-20 | 2005-03-03 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | アリールおよびアミノアリール置換セロトニン受容体アゴニストおよびアンタゴニストリガンド |
| ATE369368T1 (de) | 2000-12-27 | 2007-08-15 | Hoffmann La Roche | Indolderivate und deren verwendung als 5-ht2b- und 5-ht2c-rezeptorliganden |
| JP2004535418A (ja) | 2001-06-01 | 2004-11-25 | アルコン，インコーポレイテッド | ピラノインダゾールおよび緑内障治療への使用 |
| EP1392658A4 (en) | 2001-06-01 | 2004-10-13 | Alcon Inc | NOVEL FUSED INDAZOLES AND INDOLES AND THEIR USE IN THE TREATMENT OF GLAUCOMES |
| AU2002259312B2 (en) | 2001-06-01 | 2007-01-04 | Alcon, Inc. | Novel arylaminopropane analogues and their use for the treatment of glaucoma |
| TW593302B (en) | 2001-12-20 | 2004-06-21 | Alcon Inc | Novel benzodifuranimidazoline and benzofuranimidazoline derivatives and their use for the treatment of glaucoma |
| NZ536664A (en) | 2002-06-19 | 2007-07-27 | Biovitrum Ab | Piperazinylpyrazine derivative compounds, their use and preparation |
| WO2004019874A2 (en) * | 2002-08-30 | 2004-03-11 | Alcon, Inc. | Substituted 5-chroman-5-yl-ethylamine compounds and their use for the treatment of glaucoma |
| EP1581209A4 (en) | 2002-12-13 | 2009-03-11 | Alcon Inc | NEW BENZOPYRAN ANALOGUE AND ITS USE FOR THE TREATMENT OF GLAUKOM |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| GB0314967D0 (en) * | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| WO2005053688A1 (en) | 2003-11-26 | 2005-06-16 | Alcon, Inc. | Substituted furo[2,3-g] indazoles for the treatment of glaucoma |
| US7338972B1 (en) | 2003-12-15 | 2008-03-04 | Alcon, Inc. | Substituted 1-alkylamino-1H-indazoles for the treatment of glaucoma |
| WO2005058911A2 (en) | 2003-12-15 | 2005-06-30 | Alcon, Inc. | Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma |
| US7129257B1 (en) | 2003-12-15 | 2006-10-31 | Alcon, Inc. | Pyrazolo[3,4- e]benzoxazoles for the treatment of glaucoma |
| EP1792629A4 (en) | 2004-08-25 | 2010-08-25 | Takeda Pharmaceutical | MEANS FOR THE PREVENTION / TREATMENT OF STRESS-RELATED HARNINE INCONTINENCE AND PRECAUTIONARY METHOD FOR THIS |
| US7608626B2 (en) | 2004-11-01 | 2009-10-27 | Wyeth | Substituted indolizines and derivatives as CNS agents |
| US7425572B2 (en) | 2004-12-08 | 2008-09-16 | Alcon, Inc. | Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma |
| JP4318744B2 (ja) | 2005-03-31 | 2009-08-26 | ファイザー・プロダクツ・インク | シクロペンタピリジンおよびテトラヒドロキノリン誘導体 |
| FR2884252B1 (fr) * | 2005-04-08 | 2007-05-18 | Aventis Pharma Sa | Nouveaux derives d'isoindoles, compositions les contenant, leur preparation et leurs utilisations pharmaceutiques notamment en tant qu'inhibiteurs d'activites de la proteine chaperone hsp90 |
| AU2006239897A1 (en) * | 2005-04-22 | 2006-11-02 | Wyeth | Crystal forms of {[(2R)-7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine hydrochloride |
| EP1888585B1 (en) * | 2005-05-03 | 2011-06-29 | F. Hoffmann-La Roche AG | Tetracyclic azapyrazinoindolines as 5-ht2 ligands |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| CN101506172A (zh) * | 2006-07-14 | 2009-08-12 | 辉瑞产品公司 | （7S）-7-[（5-氟-2-甲基-苄基）氧基]-2-[（2R）-2-甲基哌嗪-1-基]-6，7-二氢-5H-环戊烷并[b]吡啶的酒石酸盐 |
| US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
| KR101062376B1 (ko) | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
| US20120253036A1 (en) | 2009-12-11 | 2012-10-04 | Yukinori Nagakura | Agent for treating fibromyalgia |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| CN102964352B (zh) * | 2012-11-23 | 2015-04-08 | 华中师范大学 | 具有生物活性的手性2,3-二氢吡咯[1,2-a]吲哚衍生物及其不对称合成方法 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
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| US3250783A (en) * | 1964-09-21 | 1966-05-10 | American Cyanamid Co | Novel pyrrolo (1, 2-alpha) indoles |
| US4134894A (en) * | 1978-05-04 | 1979-01-16 | Warner-Lambert Company | Pyrrolo[1,2-a]indole compounds |
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| US4778812A (en) * | 1987-06-12 | 1988-10-18 | American Home Products Corporation | 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-amines and derivatives thereof |
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| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
| TW251284B (enExample) * | 1992-11-02 | 1995-07-11 | Pfizer | |
| AU683447B2 (en) * | 1993-03-08 | 1997-11-13 | Fujisawa Pharmaceutical Co., Ltd. | Medicament for treating or preventing cerebrovascular diseases |
| US5629427A (en) * | 1993-08-26 | 1997-05-13 | Peterson; Dwight M. | 2,7-diaminomitosene analogues |
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1998
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- 1999-09-01 PT PT99943091T patent/PT1109813E/pt unknown
- 1999-09-01 DE DE69919364T patent/DE69919364T2/de not_active Expired - Fee Related
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- 1999-09-01 HR HR20010126A patent/HRP20010126B1/xx not_active IP Right Cessation
- 1999-09-01 KR KR1020017002608A patent/KR100768595B1/ko not_active Expired - Fee Related
- 1999-09-01 SI SI9930677T patent/SI1109813T1/xx unknown
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- 1999-09-01 IL IL14165999A patent/IL141659A0/xx active IP Right Grant
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- 1999-09-01 BR BR9913477-2A patent/BR9913477A/pt not_active Application Discontinuation
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- 1999-09-01 RU RU2001108570/04A patent/RU2232162C2/ru not_active IP Right Cessation
- 1999-09-01 EP EP99943091A patent/EP1109813B1/en not_active Expired - Lifetime
- 1999-09-01 AU AU56375/99A patent/AU758084B2/en not_active Ceased
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- 1999-09-01 MX MXPA01002101A patent/MXPA01002101A/es not_active IP Right Cessation
- 1999-09-01 KR KR1020077011961A patent/KR20070062609A/ko not_active Abandoned
- 1999-09-01 WO PCT/GB1999/002884 patent/WO2000012510A1/en not_active Ceased
- 1999-09-01 CN CNB998128341A patent/CN1165537C/zh not_active Expired - Fee Related
- 1999-09-01 YU YU16001A patent/YU16001A/sh unknown
- 1999-09-01 JP JP2000567532A patent/JP2002523508A/ja active Pending
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- 1999-09-01 CZ CZ20010772A patent/CZ296275B6/cs not_active IP Right Cessation
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