DE10315285A1 - Chromenonindole - Google Patents
Chromenonindole Download PDFInfo
- Publication number
- DE10315285A1 DE10315285A1 DE10315285A DE10315285A DE10315285A1 DE 10315285 A1 DE10315285 A1 DE 10315285A1 DE 10315285 A DE10315285 A DE 10315285A DE 10315285 A DE10315285 A DE 10315285A DE 10315285 A1 DE10315285 A1 DE 10315285A1
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- Prior art keywords
- formula
- compounds
- compound
- radical
- butyl
- Prior art date
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- -1 derivatives Substances 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 15
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- 239000012453 solvate Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 89
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- 238000000034 method Methods 0.000 claims description 13
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- 238000002360 preparation method Methods 0.000 claims description 10
- 210000004556 brain Anatomy 0.000 claims description 9
- 229910004013 NO 2 Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
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- 206010008118 cerebral infarction Diseases 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
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- JUNWDKHWFPUIHO-UHFFFAOYSA-N 3-[4-[4-(3-amino-2-oxochromen-6-yl)piperazin-1-yl]butyl]-1h-indole-5-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(C(OC4=CC=3)=O)N)=CNC2=C1 JUNWDKHWFPUIHO-UHFFFAOYSA-N 0.000 claims description 3
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- 208000014674 injury Diseases 0.000 claims description 3
- KVPVVYMWKYGYTD-UHFFFAOYSA-N methyl n-[6-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-2-oxochromen-3-yl]carbamate Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(C(OC4=CC=3)=O)NC(=O)OC)=CNC2=C1 KVPVVYMWKYGYTD-UHFFFAOYSA-N 0.000 claims description 3
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- OTUQOBBBIOAFTO-UHFFFAOYSA-N 3-[4-[4-[3-(methylamino)-2-oxochromen-6-yl]piperazin-1-yl]butyl]-1H-indole-5-carbonitrile Chemical compound CNC1=CC2=C(C=CC(=C2)N3CCN(CC3)CCCCC4=CNC5=C4C=C(C=C5)C#N)OC1=O OTUQOBBBIOAFTO-UHFFFAOYSA-N 0.000 claims description 2
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- NRTJSOPSJCPIIG-UHFFFAOYSA-N n-[6-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-2-oxochromen-3-yl]-2,2-dimethylpropanamide Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(C(OC4=CC=3)=O)NC(=O)C(C)(C)C)=CNC2=C1 NRTJSOPSJCPIIG-UHFFFAOYSA-N 0.000 claims description 2
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- AYYTXOFSFWGBLU-UHFFFAOYSA-N [6-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-2-oxochromen-3-yl]carbamic acid Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(C(OC4=CC=3)=O)NC(=O)O)=CNC2=C1 AYYTXOFSFWGBLU-UHFFFAOYSA-N 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
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- 229940076279 serotonin Drugs 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
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- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 150000003840 hydrochlorides Chemical class 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- UKFTXWKNVSVVCJ-UHFFFAOYSA-N 2-[(6-hydrazinylpyridazin-3-yl)-(2-hydroxyethyl)amino]ethanol;hydron;dichloride Chemical class Cl.Cl.NNC1=CC=C(N(CCO)CCO)N=N1 UKFTXWKNVSVVCJ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- RPZBRGFNBNQSOP-UHFFFAOYSA-N vilazodone hydrochloride Chemical compound Cl.C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)N)=CNC2=C1 RPZBRGFNBNQSOP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000036470 plasma concentration 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
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 3
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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- 229920001592 potato starch Polymers 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10315285A DE10315285A1 (de) | 2003-04-04 | 2003-04-04 | Chromenonindole |
| BRPI0408467-5A BRPI0408467A (pt) | 2003-04-04 | 2004-03-08 | cromenonaindóis |
| ES04718300T ES2335665T3 (es) | 2003-04-04 | 2004-03-08 | Cromenonaindoles. |
| MXPA05010483A MXPA05010483A (es) | 2003-04-04 | 2004-03-08 | Cromenonindoles. |
| PT04718300T PT1611126E (pt) | 2003-04-04 | 2004-03-08 | Cromenonaindóis |
| DK04718300.9T DK1611126T3 (da) | 2003-04-04 | 2004-03-08 | Chromenonindoler |
| CNA2004800085714A CN1768056A (zh) | 2003-04-04 | 2004-03-08 | 色烯酮吲哚 |
| PCT/EP2004/002351 WO2004087692A1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
| EP04718300A EP1611126B1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
| KR1020057018642A KR20050119673A (ko) | 2003-04-04 | 2004-03-08 | 크로메논 인돌 |
| JP2006504582A JP4740114B2 (ja) | 2003-04-04 | 2004-03-08 | クロメノンインドール |
| PL04718300T PL1611126T3 (pl) | 2003-04-04 | 2004-03-08 | Chromenonoindole |
| DE502004010296T DE502004010296D1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
| CA2520892A CA2520892C (en) | 2003-04-04 | 2004-03-08 | Chromenoneindoles |
| US10/551,997 US7968551B2 (en) | 2003-04-04 | 2004-03-08 | Chromenoneindoles |
| PL377730A PL377730A1 (pl) | 2003-04-04 | 2004-03-08 | Chromenonoindole |
| AT04718300T ATE446959T1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
| AU2004226279A AU2004226279B2 (en) | 2003-04-04 | 2004-03-08 | Chromenone indoles |
| ARP040101116A AR043834A1 (es) | 2003-04-04 | 2004-04-02 | Cromenonindoles |
| ZA200508922A ZA200508922B (en) | 2003-04-04 | 2005-11-03 | Chromenone indoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10315285A DE10315285A1 (de) | 2003-04-04 | 2003-04-04 | Chromenonindole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10315285A1 true DE10315285A1 (de) | 2004-10-14 |
Family
ID=32981019
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10315285A Withdrawn DE10315285A1 (de) | 2003-04-04 | 2003-04-04 | Chromenonindole |
| DE502004010296T Expired - Lifetime DE502004010296D1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004010296T Expired - Lifetime DE502004010296D1 (de) | 2003-04-04 | 2004-03-08 | Chromenonindole |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7968551B2 (enExample) |
| EP (1) | EP1611126B1 (enExample) |
| JP (1) | JP4740114B2 (enExample) |
| KR (1) | KR20050119673A (enExample) |
| CN (1) | CN1768056A (enExample) |
| AR (1) | AR043834A1 (enExample) |
| AT (1) | ATE446959T1 (enExample) |
| AU (1) | AU2004226279B2 (enExample) |
| BR (1) | BRPI0408467A (enExample) |
| CA (1) | CA2520892C (enExample) |
| DE (2) | DE10315285A1 (enExample) |
| DK (1) | DK1611126T3 (enExample) |
| ES (1) | ES2335665T3 (enExample) |
| MX (1) | MXPA05010483A (enExample) |
| PL (2) | PL377730A1 (enExample) |
| PT (1) | PT1611126E (enExample) |
| WO (1) | WO2004087692A1 (enExample) |
| ZA (1) | ZA200508922B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| US20100266504A1 (en) | 2007-11-15 | 2010-10-21 | Takahiro Matsumoto | Condensed pyridine derivative and use thereof |
| US20120253036A1 (en) | 2009-12-11 | 2012-10-04 | Yukinori Nagakura | Agent for treating fibromyalgia |
| CN103304547A (zh) * | 2012-03-13 | 2013-09-18 | 中国药科大学 | 一种抗抑郁药维拉唑酮的制备方法 |
| CN104045608B (zh) * | 2013-03-11 | 2016-06-01 | 天津药物研究院有限公司 | 一种取代哌嗪化合物及制备维拉佐酮中间体的方法 |
| CN104059046B (zh) * | 2013-03-18 | 2017-02-08 | 江苏恩华药业股份有限公司 | 黄酮类衍生物及其应用 |
| WO2015014256A1 (en) | 2013-07-29 | 2015-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use thereof |
| US10316025B2 (en) | 2015-06-03 | 2019-06-11 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4333254A1 (de) | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
| DE19730989A1 (de) | 1997-07-18 | 1999-01-21 | Merck Patent Gmbh | Piperazin-Derivate |
-
2003
- 2003-04-04 DE DE10315285A patent/DE10315285A1/de not_active Withdrawn
-
2004
- 2004-03-08 DE DE502004010296T patent/DE502004010296D1/de not_active Expired - Lifetime
- 2004-03-08 WO PCT/EP2004/002351 patent/WO2004087692A1/de not_active Ceased
- 2004-03-08 AU AU2004226279A patent/AU2004226279B2/en not_active Ceased
- 2004-03-08 KR KR1020057018642A patent/KR20050119673A/ko not_active Withdrawn
- 2004-03-08 ES ES04718300T patent/ES2335665T3/es not_active Expired - Lifetime
- 2004-03-08 US US10/551,997 patent/US7968551B2/en not_active Expired - Fee Related
- 2004-03-08 CA CA2520892A patent/CA2520892C/en not_active Expired - Fee Related
- 2004-03-08 AT AT04718300T patent/ATE446959T1/de active
- 2004-03-08 MX MXPA05010483A patent/MXPA05010483A/es not_active Application Discontinuation
- 2004-03-08 PL PL377730A patent/PL377730A1/pl unknown
- 2004-03-08 JP JP2006504582A patent/JP4740114B2/ja not_active Expired - Fee Related
- 2004-03-08 BR BRPI0408467-5A patent/BRPI0408467A/pt not_active Application Discontinuation
- 2004-03-08 PL PL04718300T patent/PL1611126T3/pl unknown
- 2004-03-08 EP EP04718300A patent/EP1611126B1/de not_active Expired - Lifetime
- 2004-03-08 CN CNA2004800085714A patent/CN1768056A/zh active Pending
- 2004-03-08 DK DK04718300.9T patent/DK1611126T3/da active
- 2004-03-08 PT PT04718300T patent/PT1611126E/pt unknown
- 2004-04-02 AR ARP040101116A patent/AR043834A1/es unknown
-
2005
- 2005-11-03 ZA ZA200508922A patent/ZA200508922B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK1611126T3 (da) | 2010-01-18 |
| CA2520892C (en) | 2012-08-21 |
| EP1611126A1 (de) | 2006-01-04 |
| JP4740114B2 (ja) | 2011-08-03 |
| WO2004087692A1 (de) | 2004-10-14 |
| ATE446959T1 (de) | 2009-11-15 |
| PL377730A1 (pl) | 2006-02-06 |
| US7968551B2 (en) | 2011-06-28 |
| AU2004226279B2 (en) | 2010-10-28 |
| PT1611126E (pt) | 2010-01-29 |
| BRPI0408467A (pt) | 2006-04-04 |
| KR20050119673A (ko) | 2005-12-21 |
| CN1768056A (zh) | 2006-05-03 |
| MXPA05010483A (es) | 2005-11-16 |
| ZA200508922B (en) | 2007-02-28 |
| JP2006522034A (ja) | 2006-09-28 |
| EP1611126B1 (de) | 2009-10-28 |
| CA2520892A1 (en) | 2004-10-14 |
| ES2335665T3 (es) | 2010-03-31 |
| PL1611126T3 (pl) | 2010-02-26 |
| AR043834A1 (es) | 2005-08-17 |
| DE502004010296D1 (de) | 2009-12-10 |
| US20060258680A1 (en) | 2006-11-16 |
| AU2004226279A1 (en) | 2004-10-14 |
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