BG107982A - Използван... на 3-индолинови производни при л...-...ни... на п'ихиа'ри-ни и н...врологи-ни раз''рой''ва - Google Patents

Използван... на 3-индолинови производни при л...-...ни... на п'ихиа'ри-ни и н...врологи-ни раз''рой''ва Download PDF

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Publication number: BG107982A
Authority: BG; Bulgaria
Prior art keywords: alkyl; cycloalkyl; hydrogen; acetyl; compound according
Prior art date: 2000-12-22

Application number

BG107982A

Other languages

Bulgarian (bg)

English (en)

Inventor

Jan Kehler

Benny Bang-Andersen

Original Assignee

H. Lundbeck A/S

Priority date (The priority date 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 date listed.)

2000-12-22

Filing date

2003-07-08

Publication date

2004-08-31

2003-07-08 Application filed by H. Lundbeck A/S filed Critical H. Lundbeck A/S

2004-08-31 Publication of BG107982A publication Critical patent/BG107982A/bg

Links

238000011282 treatment Methods 0.000 title claims abstract description 23
208000020016 psychiatric disease Diseases 0.000 title abstract description 5
208000012902 Nervous system disease Diseases 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 88
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 42
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 12
150000002367 halogens Chemical group 0.000 claims abstract description 12
125000002252 acyl group Chemical group 0.000 claims abstract description 11
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims abstract description 11
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
239000002253 acid Substances 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 7
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 7
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
125000003441 thioacyl group Chemical group 0.000 claims abstract description 5
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
-1 Cve -alkoxy Chemical group 0.000 claims description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
230000000694 effects Effects 0.000 claims description 21
208000019901 Anxiety disease Diseases 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
230000036506 anxiety Effects 0.000 claims description 12
208000028017 Psychotic disease Diseases 0.000 claims description 10
201000000980 schizophrenia Diseases 0.000 claims description 10
208000024891 symptom Diseases 0.000 claims description 10
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
230000016571 aggressive behavior Effects 0.000 claims description 7
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
208000012661 Dyskinesia Diseases 0.000 claims description 6
208000019695 Migraine disease Diseases 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
208000037870 generalized anxiety Diseases 0.000 claims description 6
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 5
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
208000010877 cognitive disease Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims description 2
230000007958 sleep Effects 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
UJLUSKUXNPLCDU-UHFFFAOYSA-N C(C)(=O)N1CCC=2C=CCCC12 Chemical compound C(C)(=O)N1CCC=2C=CCCC12 UJLUSKUXNPLCDU-UHFFFAOYSA-N 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 2
229910052799 carbon Inorganic materials 0.000 abstract description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
108020003175 receptors Proteins 0.000 description 29
102000005962 receptors Human genes 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 22
238000000034 method Methods 0.000 description 16
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229960003638 dopamine Drugs 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000005557 antagonist Substances 0.000 description 9
239000000243 solution Substances 0.000 description 8
102000003962 Dopamine D4 receptors Human genes 0.000 description 7
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239000000654 additive Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000029936 alkylation Effects 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000003446 ligand Substances 0.000 description 5
VHLVAWZWQPUHKY-UHFFFAOYSA-N 1-[3-(2-bromoethyl)-2,3-dihydroindol-1-yl]ethanone Chemical compound C1=CC=C2N(C(=O)C)CC(CCBr)C2=C1 VHLVAWZWQPUHKY-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
230000003860 sleep quality Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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 3
235000011054 acetic acid Nutrition 0.000 description 3
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125000004432 carbon atom Chemical group C* 0.000 description 3
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
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238000000338 in vitro Methods 0.000 description 3
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235000019359 magnesium stearate Nutrition 0.000 description 3
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230000010807 negative regulation of binding Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
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FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
OENHQMQUZYKXFG-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1,2,3,6-tetrahydropyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CCNCC1 OENHQMQUZYKXFG-UHFFFAOYSA-N 0.000 description 2
206010001488 Aggression Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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238000009825 accumulation Methods 0.000 description 2
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125000001246 bromo group Chemical group Br* 0.000 description 2
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XXSSQRNKZXFMJP-UHFFFAOYSA-N ethyl 4-(3,4-dichlorophenyl)-4-hydroxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1(O)C1=CC=C(Cl)C(Cl)=C1 XXSSQRNKZXFMJP-UHFFFAOYSA-N 0.000 description 2
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FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
239000012528 membrane Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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239000006188 syrup Substances 0.000 description 2
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125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 description 1
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NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
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CFPZDVAZISWERM-UHFFFAOYSA-N 4-bromo-1,2-dichlorobenzene Chemical compound ClC1=CC=C(Br)C=C1Cl CFPZDVAZISWERM-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
FOWOXWLATUAFNQ-UHFFFAOYSA-N 4-oxopiperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(=O)CC1 FOWOXWLATUAFNQ-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
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HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BG107982A 2000-12-22 2003-07-08 Използван... на 3-индолинови производни при л...-...ни... на п'ихиа'ри-ни и н...врологи-ни раз''рой''ва BG107982A (bg)

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DKPA200001931		2000-12-22
PCT/DK2001/000835 WO2002051833A1 (en)	2000-12-22	2001-12-18	3-indoline derivatives useful in the treatment of psychiatric and neurologic disorders

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US (1)	US20040044007A1 (no)
EP (1)	EP1345921A1 (no)
JP (1)	JP2004516321A (no)
KR (1)	KR20030063455A (no)
CN (1)	CN1491223A (no)
AR (1)	AR035521A1 (no)
BG (1)	BG107982A (no)
BR (1)	BR0116365A (no)
CA (1)	CA2432473A1 (no)
CZ (1)	CZ20032004A3 (no)
EA (1)	EA200300718A1 (no)
HU (1)	HUP0500350A2 (no)
IL (1)	IL156340A0 (no)
IS (1)	IS6837A (no)
MX (1)	MXPA03005555A (no)
NO (1)	NO20032636L (no)
PL (1)	PL362133A1 (no)
SK (1)	SK9342003A3 (no)
WO (1)	WO2002051833A1 (no)
ZA (1)	ZA200304643B (no)

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SK51052006A3 (sk) *	2004-05-11	2007-05-03	Egis Gy�gyszergy�r Nyrt.	Pyridínové deriváty alkyloxindolov ako aktívne látky voči 5-HT7 receptoru
AR052308A1 (es) *	2004-07-16	2007-03-14	Lundbeck & Co As H	Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto
PE20061130A1 (es)	2004-11-19	2007-01-05	Arena Pharm Inc	Derivados de 3-fenil-pirazol como moduladores del receptor de serotonina 5-ht2a
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TWI415845B (zh)	2006-10-03	2013-11-21	Arena Pharm Inc	用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物
KR100868353B1 (ko) *	2007-03-08	2008-11-12	한국화학연구원	도파민 ｄ4 수용체 길항제인 신규 피페라지닐프로필피라졸유도체, 이의 제조방법 및 이를 포함하는 약학적 조성물
US9567327B2 (en)	2007-08-15	2017-02-14	Arena Pharmaceuticals, Inc.	Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto
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KR101062376B1 (ko)	2008-04-10	2011-09-06	한국화학연구원	신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물
WO2010062321A1 (en)	2008-10-28	2010-06-03	Arena Pharmaceuticals, Inc.	Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto
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DE4101686A1 (de) *	1991-01-22	1992-07-23	Merck Patent Gmbh	Indolderivate
NZ243065A (en) *	1991-06-13	1995-07-26	Lundbeck & Co As H	Piperidine derivatives and pharmaceutical compositions
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DE19512639A1 (de) *	1995-04-05	1996-10-10	Merck Patent Gmbh	Benzonitrile und -fluoride
ITMI20012060A1 (it) *	2001-10-05	2003-04-05	Recordati Chem Pharm	Nuovi eterocilcli n-acilati

2001
- 2001-12-17 AR ARP010105843A patent/AR035521A1/es not_active Application Discontinuation
- 2001-12-18 KR KR10-2003-7008437A patent/KR20030063455A/ko not_active Withdrawn
- 2001-12-18 MX MXPA03005555A patent/MXPA03005555A/es unknown
- 2001-12-18 PL PL36213301A patent/PL362133A1/xx unknown
- 2001-12-18 BR BR0116365-5A patent/BR0116365A/pt not_active Application Discontinuation
- 2001-12-18 CN CNA018227481A patent/CN1491223A/zh active Pending
- 2001-12-18 CA CA002432473A patent/CA2432473A1/en not_active Abandoned
- 2001-12-18 JP JP2002552928A patent/JP2004516321A/ja not_active Withdrawn
- 2001-12-18 EA EA200300718A patent/EA200300718A1/ru unknown
- 2001-12-18 EP EP01271969A patent/EP1345921A1/en not_active Withdrawn
- 2001-12-18 ZA ZA200304643A patent/ZA200304643B/en unknown
- 2001-12-18 CZ CZ20032004A patent/CZ20032004A3/cs unknown
- 2001-12-18 SK SK934-2003A patent/SK9342003A3/sk unknown
- 2001-12-18 WO PCT/DK2001/000835 patent/WO2002051833A1/en not_active Ceased
- 2001-12-18 HU HU0500350A patent/HUP0500350A2/hu unknown
- 2001-12-18 IL IL15634001A patent/IL156340A0/xx unknown
2003
- 2003-06-05 IS IS6837A patent/IS6837A/is unknown
- 2003-06-11 NO NO20032636A patent/NO20032636L/no not_active Application Discontinuation
- 2003-06-17 US US10/601,347 patent/US20040044007A1/en not_active Abandoned
- 2003-07-08 BG BG107982A patent/BG107982A/bg unknown

Also Published As

Publication number	Publication date
NO20032636D0 (no)	2003-06-11
CN1491223A (zh)	2004-04-21
US20040044007A1 (en)	2004-03-04
AR035521A1 (es)	2004-06-02
NO20032636L (no)	2003-06-11
HUP0500350A2 (hu)	2005-08-29
CA2432473A1 (en)	2002-07-04
EP1345921A1 (en)	2003-09-24
WO2002051833A1 (en)	2002-07-04
SK9342003A3 (en)	2003-10-07
IL156340A0 (en)	2004-01-04
PL362133A1 (en)	2004-10-18
BR0116365A (pt)	2004-07-06
EA200300718A1 (ru)	2003-10-30
CZ20032004A3 (cs)	2003-10-15
JP2004516321A (ja)	2004-06-03
ZA200304643B (en)	2004-07-19
KR20030063455A (ko)	2003-07-28
MXPA03005555A (es)	2004-03-26
IS6837A (is)	2003-06-05

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