RU2077535C1 - Производные бензанилида, способ их получения и фармацевтическая композиция, проявляющая антагонизм к 5-htid рецепторам - Google Patents
Производные бензанилида, способ их получения и фармацевтическая композиция, проявляющая антагонизм к 5-htid рецепторам Download PDFInfo
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- RU2077535C1 RU2077535C1 SU925052871A SU5052871A RU2077535C1 RU 2077535 C1 RU2077535 C1 RU 2077535C1 SU 925052871 A SU925052871 A SU 925052871A SU 5052871 A SU5052871 A SU 5052871A RU 2077535 C1 RU2077535 C1 RU 2077535C1
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- RU
- Russia
- Prior art keywords
- methyl
- phenyl
- piperazinyl
- carboxamide
- biphenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 title claims description 3
- 230000008485 antagonism Effects 0.000 title claims 2
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 4
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- 230000001747 exhibiting effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- -1 4-methoxy-3- (4-methyl-1-piperazinyl) phenyl Chemical group 0.000 claims description 94
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 70
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- 150000003839 salts Chemical class 0.000 claims description 35
- 239000012453 solvate Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Chemical group 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| GB919119931A GB9119931D0 (en) | 1991-09-18 | 1991-09-18 | Chemical compounds |
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| GB929205338A GB9205338D0 (en) | 1992-03-12 | 1992-03-12 | Chemical compounds |
| GB9205338.8 | 1992-03-12 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2179976C2 (ru) * | 1996-09-18 | 2002-02-27 | Лид Кемикал Ко., Лтд. | Новые производные 2,4-диоксопирролидина и 2,4-диоксотетрагидрофурана и лекарственные средства, содержащие их в качестве активного ингредиента |
| RU2215528C2 (ru) * | 1997-09-18 | 2003-11-10 | Астразенека Аб | Комбинация селективного антагониста 5-нт1a и селективного антагониста или частичного агониста н5-нт1b |
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| US5696122A (en) * | 1993-09-03 | 1997-12-09 | Smithkline Beecham P.L.C. | Indole and indoline derivatives as 5HT1D receptor antagonists |
| EP0716656A1 (en) * | 1993-09-03 | 1996-06-19 | Smithkline Beecham Plc | Amide derivatives as 5ht1d receptor antagonists |
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| JPH09506101A (ja) * | 1993-12-07 | 1997-06-17 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５ｈｔ１ｄ拮抗薬として有用な複素環式ビフェニリルアミド類 |
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| AU2565595A (en) * | 1994-05-28 | 1995-12-21 | Smithkline Beecham Plc | Amide derivatives having 5ht1d-antagonist activity |
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| FR2740134B1 (fr) * | 1995-10-18 | 1998-01-09 | Pf Medicament | Derives d'amines cycliques d'aryl-piperazines, leur preparation et les compositions pharmaceutiques les contenant |
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| FR2744450A1 (fr) * | 1996-02-02 | 1997-08-08 | Pf Medicament | Nouvelles naphtylpiperazines derivees de cycloazanes substitues, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| FR2744449B1 (fr) * | 1996-02-02 | 1998-04-24 | Pf Medicament | Nouvelles piperazines aromatiques derivees de cycloazanes substitues, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| GB9605883D0 (en) * | 1996-03-20 | 1996-05-22 | Smithkline Beecham Plc | Novel compounds |
| GB9605945D0 (en) * | 1996-03-21 | 1996-05-22 | Smithkline Beecham Plc | Novel compounds |
| SE9601110D0 (sv) * | 1996-03-22 | 1996-03-22 | Astra Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
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| SE9900190D0 (sv) | 1999-01-22 | 1999-01-22 | Astra Ab | New compounds |
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| US4735959A (en) * | 1981-01-10 | 1988-04-05 | Dr. Karl Thomae Gmbh | Carboxylic acid amides and pharmaceutical compositions containing them |
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| US4778796A (en) * | 1985-07-19 | 1988-10-18 | Dainippon Pharmaceutical Co., Ltd. | ω-(3-pyridyl)alkenamide derivatives and anti-allergenic pharmaceutical compositions containing same |
| DE3600288A1 (de) * | 1986-01-08 | 1987-07-16 | Bayer Ag | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen sulfonylharnstoff-derivaten |
| CA1334092C (en) * | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| US4853398A (en) * | 1987-04-13 | 1989-08-01 | Eli Lilly And Company | Leukotriene antagonists and use thereas |
| US4826990A (en) * | 1987-09-30 | 1989-05-02 | American Home Products Corporation | 2-aryl substituted heterocyclic compounds as antiallergic and antiinflammatory agents |
| EP0324521A3 (en) * | 1988-01-11 | 1991-11-27 | Duphar International Research B.V | Method of treating haematologic diseases and pharmaceutical compositions to be used therefor |
| DE3810848A1 (de) * | 1988-03-30 | 1989-10-19 | Boehringer Ingelheim Kg | Neue 2,3,4-substituierte imidazole und 3,4,5-substituierte 1,2,4-triazole, ihre herstellung und verwendung |
| DE68903263T2 (de) * | 1988-10-10 | 1993-05-19 | Akzo Nv | Substituierte aromatische verbindungen mit zentraler nervensystem-wirkung. |
-
1992
- 1992-09-14 EP EP92202806A patent/EP0533268B1/en not_active Expired - Lifetime
- 1992-09-14 DK DK92202806T patent/DK0533268T3/da active
- 1992-09-14 ES ES92202806T patent/ES2162792T3/es not_active Expired - Lifetime
- 1992-09-14 AT AT92202806T patent/ATE204262T1/de not_active IP Right Cessation
- 1992-09-14 PT PT92202806T patent/PT533268E/pt unknown
- 1992-09-14 DE DE69232003T patent/DE69232003T2/de not_active Expired - Fee Related
- 1992-09-17 CN CN92111660A patent/CN1071919A/zh active Pending
- 1992-09-17 TW TW081107321A patent/TW224097B/zh active
- 1992-09-17 PL PL29596092A patent/PL295960A1/xx unknown
- 1992-09-17 NO NO92923618A patent/NO923618L/no unknown
- 1992-09-17 US US07/946,098 patent/US5340810A/en not_active Expired - Fee Related
- 1992-09-17 IS IS3915A patent/IS1618B/is unknown
- 1992-09-17 RU SU925052871A patent/RU2077535C1/ru active
- 1992-09-17 IL IL10319892A patent/IL103198A/en not_active IP Right Cessation
- 1992-09-17 JP JP27361992A patent/JP3295143B2/ja not_active Expired - Fee Related
- 1992-09-17 NZ NZ244373A patent/NZ244373A/en unknown
- 1992-09-17 FI FI924160A patent/FI924160A7/fi not_active Application Discontinuation
- 1992-09-17 HU HU9202968A patent/HUT65608A/hu unknown
- 1992-09-17 AU AU24530/92A patent/AU656021B2/en not_active Ceased
- 1992-09-17 MX MX9205280A patent/MX9205280A/es not_active IP Right Cessation
- 1992-09-17 MY MYPI92001663A patent/MY130233A/en unknown
- 1992-09-17 AP APAP/P/1992/000427A patent/AP303A/en active
- 1992-09-17 CZ CS922854A patent/CZ285492A3/cs unknown
- 1992-09-17 CA CA002078505A patent/CA2078505A1/en not_active Abandoned
- 1992-09-17 OA OA60277A patent/OA10049A/en unknown
- 1992-09-17 KR KR1019920016904A patent/KR930006011A/ko not_active Ceased
-
1994
- 1994-05-03 US US08/237,297 patent/US5510350A/en not_active Expired - Fee Related
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2179976C2 (ru) * | 1996-09-18 | 2002-02-27 | Лид Кемикал Ко., Лтд. | Новые производные 2,4-диоксопирролидина и 2,4-диоксотетрагидрофурана и лекарственные средства, содержащие их в качестве активного ингредиента |
| RU2215528C2 (ru) * | 1997-09-18 | 2003-11-10 | Астразенека Аб | Комбинация селективного антагониста 5-нт1a и селективного антагониста или частичного агониста н5-нт1b |
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