ES2228588T3 - Derivados de indol, procedimientos para su preparacion, composiciones farmaceuticas que los contienen y su aplicacion en medicina. - Google Patents
Derivados de indol, procedimientos para su preparacion, composiciones farmaceuticas que los contienen y su aplicacion en medicina.Info
- Publication number
- ES2228588T3 ES2228588T3 ES00951697T ES00951697T ES2228588T3 ES 2228588 T3 ES2228588 T3 ES 2228588T3 ES 00951697 T ES00951697 T ES 00951697T ES 00951697 T ES00951697 T ES 00951697T ES 2228588 T3 ES2228588 T3 ES 2228588T3
- Authority
- ES
- Spain
- Prior art keywords
- indole
- disorders
- compound according
- hydrogen
- tetrahydrocyclopent
- 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.)
- Expired - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 46
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 26
- 238000002360 preparation method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- -1 indole-4-yl Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 230000006399 behavior Effects 0.000 claims description 3
- 208000015114 central nervous system disease Diseases 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- LUKIRABZVWKFRD-JTQLQIEISA-N (2s)-1-(2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C12=CC=CC=C2N(C[C@@H](N)C)C2=C1CCC2 LUKIRABZVWKFRD-JTQLQIEISA-N 0.000 claims description 2
- WMRPUWLJSFVKAG-JTQLQIEISA-N (2s)-1-(6-methoxy-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C[C@H](N)CN1C2=CC(OC)=CC=C2C2=C1CCC2 WMRPUWLJSFVKAG-JTQLQIEISA-N 0.000 claims description 2
- FZCHCFCPCPAJQO-QMMMGPOBSA-N (2s)-1-(7,8-difluoro-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C12=C(F)C(F)=CC=C2N(C[C@@H](N)C)C2=C1CCC2 FZCHCFCPCPAJQO-QMMMGPOBSA-N 0.000 claims description 2
- RTSLCQIJASRWOX-VIFPVBQESA-N (2s)-1-(7-fluoro-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C12=CC(F)=CC=C2N(C[C@@H](N)C)C2=C1CCC2 RTSLCQIJASRWOX-VIFPVBQESA-N 0.000 claims description 2
- YGQDXCISPLBUAT-VIFPVBQESA-N (2s)-1-(7-fluoro-6-methoxy-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C1=C(F)C(OC)=CC2=C1C(CCC1)=C1N2C[C@H](C)N YGQDXCISPLBUAT-VIFPVBQESA-N 0.000 claims description 2
- OUHZFJSASFPXFM-VIFPVBQESA-N (2s)-1-(8-chloro-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound C12=C(Cl)C=CC=C2N(C[C@@H](N)C)C2=C1CCC2 OUHZFJSASFPXFM-VIFPVBQESA-N 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000032841 Bulimia Diseases 0.000 claims description 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 201000009906 Meningitis Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 206010041250 Social phobia Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 208000025748 atypical depressive disease Diseases 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 230000002458 infectious effect Effects 0.000 claims description 2
- 238000007917 intracranial administration Methods 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 208000022821 personality disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 201000002859 sleep apnea Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000001738 Nervous System Trauma Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 206010016256 fatigue Diseases 0.000 claims 1
- 230000005176 gastrointestinal motility Effects 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 208000028412 nervous system injury Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009967 tasteless effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 150000002475 indoles Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 12
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 12
- 125000001041 indolyl group Chemical group 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 8
- 125000002015 acyclic group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 6
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- HZDXFZHFEASSBM-UHFFFAOYSA-N 1,2,3,4-tetrahydrocyclopenta[b]indole Chemical class N1C2=CC=CC=C2C2=C1CCC2 HZDXFZHFEASSBM-UHFFFAOYSA-N 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 description 4
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000883 anti-obesity agent Substances 0.000 description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- 239000012458 free base Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 239000003981 vehicle Substances 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
- IZGGZTCEQQMXCZ-LOOJJACZSA-N (e)-but-2-enedioic acid;(2s)-1-(7,8-difluoro-2,3-dihydro-1h-cyclopenta[b]indol-4-yl)propan-2-amine Chemical compound OC(=O)\C=C\C(O)=O.C12=C(F)C(F)=CC=C2N(C[C@@H](N)C)C2=C1CCC2 IZGGZTCEQQMXCZ-LOOJJACZSA-N 0.000 description 3
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 3
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 101150013372 Htr2c gene Proteins 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- 238000002347 injection Methods 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
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- 239000007921 spray Substances 0.000 description 3
- CGGDZRXYMJKIKG-UHFFFAOYSA-N tri(propan-2-yl)-(1,2,3,4-tetrahydrocyclopenta[b]indol-6-ylsulfanyl)silane Chemical compound N1C2=CC(S[Si](C(C)C)(C(C)C)C(C)C)=CC=C2C2=C1CCC2 CGGDZRXYMJKIKG-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
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- GDQKXBCJNLHHFC-UHFFFAOYSA-N 6-ethylsulfanyl-1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound N1C2=CC(SCC)=CC=C2C2=C1CCC2 GDQKXBCJNLHHFC-UHFFFAOYSA-N 0.000 description 2
- VSAFAJXSNSESEN-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound N1C2=CC(OC)=CC=C2C2=C1CCC2 VSAFAJXSNSESEN-UHFFFAOYSA-N 0.000 description 2
- FIVWWCBDQKQKHF-UHFFFAOYSA-N 7,8-difluoro-1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound C12=C(F)C(F)=CC=C2NC2=C1CCC2 FIVWWCBDQKQKHF-UHFFFAOYSA-N 0.000 description 2
- PQYHPNGINKDCQJ-UHFFFAOYSA-N 7,8-difluoro-2,3,3a,4,4a,8b-hexahydro-1h-cyclopenta[b]indol-8a-ol Chemical compound C1=CC(F)=C(F)C2(O)C1NC1CCCC12 PQYHPNGINKDCQJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Toxicology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9918962 | 1999-08-11 | ||
| GBGB9918962.3A GB9918962D0 (en) | 1999-08-11 | 1999-08-11 | Chemical compounds xxii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2228588T3 true ES2228588T3 (es) | 2005-04-16 |
Family
ID=10858982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00951697T Expired - Lifetime ES2228588T3 (es) | 1999-08-11 | 2000-08-04 | Derivados de indol, procedimientos para su preparacion, composiciones farmaceuticas que los contienen y su aplicacion en medicina. |
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| US (1) | US6706750B1 (enExample) |
| EP (1) | EP1202965B1 (enExample) |
| JP (1) | JP2003507367A (enExample) |
| KR (1) | KR100740172B1 (enExample) |
| CN (1) | CN1187330C (enExample) |
| AR (1) | AR037222A1 (enExample) |
| AT (1) | ATE279392T1 (enExample) |
| AU (1) | AU773337B2 (enExample) |
| BR (1) | BR0013307A (enExample) |
| CA (1) | CA2377646A1 (enExample) |
| DE (1) | DE60014918T2 (enExample) |
| DK (1) | DK1202965T3 (enExample) |
| ES (1) | ES2228588T3 (enExample) |
| GB (1) | GB9918962D0 (enExample) |
| MX (1) | MXPA01013235A (enExample) |
| PE (1) | PE20010574A1 (enExample) |
| PT (1) | PT1202965E (enExample) |
| TR (1) | TR200200352T2 (enExample) |
| UY (1) | UY26291A1 (enExample) |
| WO (1) | WO2001012603A1 (enExample) |
| ZA (1) | ZA200110217B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9902047D0 (en) * | 1999-01-29 | 1999-03-17 | Cerebrus Ltd | Chemical compounds XI |
| GB9918965D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxi |
| US20040077605A1 (en) * | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| EP1854798A3 (en) * | 2000-09-19 | 2007-11-28 | Bristol-Myers Squibb Company | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| WO2002044152A1 (en) * | 2000-10-16 | 2002-06-06 | F. Hoffmann-La Roche Ag | Indoline derivatives and their use as 5-ht2 receptor ligands |
| WO2002048150A2 (en) * | 2000-11-02 | 2002-06-20 | The Government Of The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Agents useful for reducing amyloid precursor protein and treating demantia and methods of use thereof |
| US6777407B2 (en) | 2000-11-03 | 2004-08-17 | Wyeth | Cyclopenta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives |
| US6759405B2 (en) | 2000-11-03 | 2004-07-06 | Wyeth | Cycloocta[b][1,4]diazepino[6,7,1-hi]indoles and derivatives |
| AR031199A1 (es) | 2000-11-03 | 2003-09-10 | Wyeth Corp | Ciclohepta/b//1,4/diacepino/6,7,1-hi/indoles y derivados |
| SE0004245D0 (sv) | 2000-11-20 | 2000-11-20 | Pharmacia Ab | Novel compounds and their use |
| JP4204315B2 (ja) | 2000-11-20 | 2009-01-07 | ビオヴィトルム・アクチボラゲット（プブリクト） | セロトニン５−ｈｔ２レセプターのアンタゴニストとしてのピペラジニルピラジン化合物 |
| US20040087548A1 (en) | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| US7087636B2 (en) * | 2001-12-19 | 2006-08-08 | Bristol-Myers Squibb Company | Fused heterocyclic compounds and analogs thereof, modulators of nuclear hormone receptor function |
| TWI312781B (en) | 2002-04-25 | 2009-08-01 | [1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents | |
| TW200307540A (en) * | 2002-04-25 | 2003-12-16 | Wyeth Corp | [1, 4]Diazocino[7, 8, 1-hi] indole derivatives as antipsychotic and antiobesity agents |
| TW200307682A (en) | 2002-04-25 | 2003-12-16 | Wyeth Corp | 1,2,3,4,7,8-Hexahydro-6H-[1,4]diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents |
| BR0311970A (pt) | 2002-06-19 | 2005-03-29 | Biovitrum Ab | Novos compostos, seu uso e preparação |
| WO2004063156A1 (en) * | 2003-01-08 | 2004-07-29 | Biovitrum Ab | Novel indole derivates as fabp-4 inhibitors |
| 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 |
| CN1960725A (zh) * | 2004-03-15 | 2007-05-09 | Ptc医疗公司 | 用于抑制血管发生的四环咔啉衍生物 |
| US8076352B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US7767689B2 (en) * | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US7601840B2 (en) * | 2004-03-15 | 2009-10-13 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the inhibition of angiogenesis |
| US8076353B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| WO2006012310A2 (en) * | 2004-06-25 | 2006-02-02 | Genzyme Corporation | Carbazole derivatives for treating polycystic kidney disease |
| JP5173190B2 (ja) | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| GT200500317A (es) | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
| CN101119717A (zh) * | 2004-11-23 | 2008-02-06 | Ptc医疗公司 | 用作抑制vegf产生的活性剂的取代酚 |
| EP1817025A2 (en) * | 2004-11-23 | 2007-08-15 | PTC Therapeutics, Inc. | Tetrahydrocarbazoles as active agents for inhibiting vegf production by translational control |
| GB2422828A (en) * | 2005-02-03 | 2006-08-09 | Hunter Fleming Ltd | Tricyclic cytoprotective compounds comprising an indole residue |
| AR054849A1 (es) | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
| US20250051276A1 (en) * | 2021-12-15 | 2025-02-13 | Delix Therapeutics, Inc. | Aryloxy psychoplastogens and uses thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2541211A (en) * | 1948-10-15 | 1951-02-13 | Searle & Co | Tertiary-aminoalkyl-tetrahydrocarbazoles |
| US2687414A (en) | 1948-11-26 | 1954-08-24 | Searle & Co | Method for producing aromatic aminoalkyl amines |
| DE930988C (de) | 1953-01-01 | 1955-07-28 | Bayer Ag | Verfahren zur Herstellung von basisch alkylierten Tetrahydrocarbazolen oder Indolen |
| US3151120A (en) * | 1961-08-15 | 1964-09-29 | Ciba Geigy Corp | Thieno [3, 2-b] indole esters and amides |
| US3133930A (en) * | 1961-08-15 | 1964-05-19 | Ciba Geigy Corp | Ester and amide derivatives of thieno-[3, 2-b] indole 3-carboxylic acids |
| US3329571A (en) * | 1961-10-24 | 1967-07-04 | American Home Prod | Methods for treating depression |
| NL284655A (enExample) | 1961-10-24 | |||
| US3142678A (en) * | 1962-01-09 | 1964-07-28 | American Home Prod | Amino substituted penthienoindoles |
| TW334423B (en) * | 1993-10-22 | 1998-06-21 | Hoffmann La Roche | Tricyclic 1-aminoethylpyrrole-derivatives |
| TW270114B (enExample) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| TW403738B (en) | 1994-08-12 | 2000-09-01 | Hoffmann La Roche | Tricyclic pyrazole derivatives |
| AU5343298A (en) | 1997-01-13 | 1998-08-03 | Yamanouchi Pharmaceutical Co., Ltd. | 5-ht2c receptor agonists and aminoalkylindazole derivatives |
-
1999
- 1999-08-11 GB GBGB9918962.3A patent/GB9918962D0/en not_active Ceased
-
2000
- 2000-08-04 DE DE60014918T patent/DE60014918T2/de not_active Expired - Fee Related
- 2000-08-04 JP JP2001517501A patent/JP2003507367A/ja active Pending
- 2000-08-04 CA CA002377646A patent/CA2377646A1/en not_active Abandoned
- 2000-08-04 ES ES00951697T patent/ES2228588T3/es not_active Expired - Lifetime
- 2000-08-04 AT AT00951697T patent/ATE279392T1/de not_active IP Right Cessation
- 2000-08-04 CN CNB00811515XA patent/CN1187330C/zh not_active Expired - Fee Related
- 2000-08-04 DK DK00951697T patent/DK1202965T3/da active
- 2000-08-04 EP EP00951697A patent/EP1202965B1/en not_active Expired - Lifetime
- 2000-08-04 US US10/009,568 patent/US6706750B1/en not_active Expired - Fee Related
- 2000-08-04 TR TR2002/00352T patent/TR200200352T2/xx unknown
- 2000-08-04 WO PCT/GB2000/003011 patent/WO2001012603A1/en not_active Ceased
- 2000-08-04 PT PT00951697T patent/PT1202965E/pt unknown
- 2000-08-04 BR BR0013307-8A patent/BR0013307A/pt not_active Application Discontinuation
- 2000-08-04 KR KR1020027001108A patent/KR100740172B1/ko not_active Expired - Fee Related
- 2000-08-04 AU AU64555/00A patent/AU773337B2/en not_active Ceased
- 2000-08-04 MX MXPA01013235A patent/MXPA01013235A/es active IP Right Grant
- 2000-08-09 PE PE2000000807A patent/PE20010574A1/es not_active Application Discontinuation
- 2000-08-10 AR ARP000104120A patent/AR037222A1/es unknown
- 2000-08-11 UY UY26291A patent/UY26291A1/es not_active Application Discontinuation
-
2001
- 2001-12-12 ZA ZA200110217A patent/ZA200110217B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20010574A1 (es) | 2001-05-21 |
| DE60014918T2 (de) | 2005-10-13 |
| GB9918962D0 (en) | 1999-10-13 |
| EP1202965A1 (en) | 2002-05-08 |
| EP1202965B1 (en) | 2004-10-13 |
| ZA200110217B (en) | 2002-12-12 |
| KR20020015078A (ko) | 2002-02-27 |
| AU773337B2 (en) | 2004-05-20 |
| PT1202965E (pt) | 2005-01-31 |
| CA2377646A1 (en) | 2001-02-22 |
| DK1202965T3 (da) | 2005-02-14 |
| WO2001012603A1 (en) | 2001-02-22 |
| CN1187330C (zh) | 2005-02-02 |
| JP2003507367A (ja) | 2003-02-25 |
| TR200200352T2 (enExample) | 2002-06-21 |
| DE60014918D1 (de) | 2004-11-18 |
| AR037222A1 (es) | 2004-11-03 |
| AU6455500A (en) | 2001-03-13 |
| KR100740172B1 (ko) | 2007-07-16 |
| US6706750B1 (en) | 2004-03-16 |
| ATE279392T1 (de) | 2004-10-15 |
| CN1368960A (zh) | 2002-09-11 |
| BR0013307A (pt) | 2002-05-28 |
| MXPA01013235A (es) | 2002-06-04 |
| UY26291A1 (es) | 2001-03-16 |
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