FR2396757A2 - Psycho-functional alkylene bis:oxy benzamide cpds. - useful in gastroenterology, cardiology, urology, rheumatology and gynaecology - Google Patents
Psycho-functional alkylene bis:oxy benzamide cpds. - useful in gastroenterology, cardiology, urology, rheumatology and gynaecologyInfo
- Publication number
- FR2396757A2 FR2396757A2 FR7721088A FR7721088A FR2396757A2 FR 2396757 A2 FR2396757 A2 FR 2396757A2 FR 7721088 A FR7721088 A FR 7721088A FR 7721088 A FR7721088 A FR 7721088A FR 2396757 A2 FR2396757 A2 FR 2396757A2
- Authority
- FR
- France
- Prior art keywords
- substd
- alkyl
- alkoxy
- amino
- acyl
- 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.)
- Granted
Links
- 125000002947 alkylene group Chemical group 0.000 title abstract 4
- -1 oxy benzamide Chemical compound 0.000 title abstract 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 125000002252 acyl group Chemical group 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000002541 furyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 abstract 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003441 thioacyl group Chemical group 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 229940054066 benzamide antipsychotics Drugs 0.000 abstract 1
- 150000003936 benzamides Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
bis(oxy) benzamides of formula (I), their quat. ammonium salts, oxides, and their dextrorotatory and laevorotatory isomers, are new. In (I) A=1-3C alkylene, opt. substd. by 1-4C alkyl, 2-4C alkenyl or hydroxyalkyl, R=H, 1-4C alkyl or a group-B-N-R1 R2 B=a single bond, 1-3C alkylene opt. substd. by 1-4C alkyl or 2-4C alkenyl, R1=H, 1-4C alkyl, 2-4C alkenyl or alkynyl, alkyl substd. by OH, SH, acyl, thioacyl alkoxy, alkylthio, amino or may be attached to B to form a satd or unsatd. N-heterocycle, R2=H, 1-4C alkyl, 2-4C alkenyl or alkynyl, alkyl substd by OH, SH, acyl, thioacyl, alkoxy, alkyl thio, amino, or a satd. or unsatd. opt. substd. heterocycle phenyl, adamantyl, cycloalkyl, bicyclolakyl, cycloalkenyl, attached directly or through an alkylene chain, or R1 & R2 together form a heterocycle which contain further heteroatoms, and may be substd by 1-4C alkyl, 2-4C alkenyl or alkynyl, phenyl, benzyl, cycloalkyl, cycloalkenyl, cycloalkanealkyl, adamantyl, bicycloalkyl or alkyl substd by OH, SH acyl, thioacyl, alkoxy or alklthio. R'=H, 1-4C alkyl, 2-4C alkenyl or alkynyl, adamantyl, pyrimidinyl, pyrazinyl, diazepinyl, quinuclidinyl, azabicycloalkyl, diazabicyloalkyl, bicycloalkyl, phenyl opt. substd. or R' & B may together form a N heterocycle, which may be substd, or R' & R1 a di-N heterocycle which may be substd. X=H, halogen, OH, 1-4C alkoxy or alkyl, amino, mono or di-alkyl substd, amino, acyl, aralkyl, furanyl, pyranyl, or alkoxycarbonyl. Y=H, halogen, OH, 1-4C alkoxy, NO2, amino, alkyl substd. amono, acyl, aralkyl, furanyl, pyranyl, alkoxy-carbonyl, 1-4C alkylsulphonyl, adamantyl sulphoncycloalkyl sulphonyl or sulphonyl substd by a mono - or di-substd amino gp. Z=H, halogen, OH, 1-4C alkoxy, NO2 amino opt. mono-or di- substd. by 1-4C alkyl, acyl, aralkyl, furanyl, pyranyl, or alkoxycarbonyl, or X & Y or Y & Z may be bonded together by one or ore heteroatoms, which may be substd. to form a ring. Daily dose is 50-900 (50-300)mg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7721088A FR2396757A2 (en) | 1977-07-08 | 1977-07-08 | Psycho-functional alkylene bis:oxy benzamide cpds. - useful in gastroenterology, cardiology, urology, rheumatology and gynaecology |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7721088A FR2396757A2 (en) | 1977-07-08 | 1977-07-08 | Psycho-functional alkylene bis:oxy benzamide cpds. - useful in gastroenterology, cardiology, urology, rheumatology and gynaecology |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2396757A2 true FR2396757A2 (en) | 1979-02-02 |
| FR2396757B2 FR2396757B2 (en) | 1980-07-25 |
Family
ID=9193153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7721088A Granted FR2396757A2 (en) | 1977-07-08 | 1977-07-08 | Psycho-functional alkylene bis:oxy benzamide cpds. - useful in gastroenterology, cardiology, urology, rheumatology and gynaecology |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2396757A2 (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438044A2 (en) * | 1978-04-10 | 1980-04-30 | Delalande Sa | Alkylene di:oxy benzene derivs. - intermediates for cinnamoyl piperazine(s) having anti-angina activity and also effect on circulation (SW 12.11.79) |
| FR2447918A1 (en) * | 1979-02-05 | 1980-08-29 | Delalande Sa | 1-Cinnamoyl-4-phenyl-hydroxy-propyl-piperazine derivs. - used to treat angina, cardiovascular troubles and improve cerebral and peripheral circulation |
| EP0123386A1 (en) * | 1983-02-28 | 1984-10-31 | Sumitomo Chemical Company, Limited | Fungicidal N-(condensed phenyl) carbamates |
| EP0147044A3 (en) * | 1983-12-22 | 1985-11-21 | Adria Laboratories Inc. | Benzofurancarboxamides, process for their preparation and pharmaceutical preparations containing them |
| EP0171636A1 (en) * | 1984-08-14 | 1986-02-19 | RAVIZZA S.p.A. | Pharmacologically active piperazino derivatives and the process for their preparation |
| FR2586018A1 (en) * | 1985-08-12 | 1987-02-13 | Ile De France | NOVEL BENZODIOXEPANNE, METHOD OF SYNTHESIS AND THERAPEUTIC APPLICATIONS |
| WO1988001866A1 (en) * | 1986-09-09 | 1988-03-24 | Adria Laboratories, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US4888353A (en) * | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| US5175173A (en) * | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
| US5185335A (en) * | 1990-03-06 | 1993-02-09 | Janssen Pharmaceutica N.V. | N-(4-piperodinyl)(dihydrobenzofuran or dihydro-2h-benzopyran) carboxamide derivatives |
| WO1993005038A1 (en) * | 1991-09-12 | 1993-03-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| GR920100469A (en) * | 1992-10-19 | 1994-06-30 | Smithkline Beecham Plc | Pharmaceutical substances. |
| AP373A (en) * | 1991-09-14 | 1994-12-07 | Smithkline Beecham Plc | Compounds having 5TH4 receptor antagonist activity. |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| WO1994029298A1 (en) * | 1993-06-16 | 1994-12-22 | Smithkline Beecham Plc | 8-amino-7-chloro-1,4-benzodioxan-5-carboxylic acid, -1-butyl-4-piperidinyl ester as a 5-ht4-receptor antagonist |
| ES2065238A1 (en) * | 1992-11-20 | 1995-02-01 | Smithkline Beecham Plc | Condensed benzene derivatives with 5-HT4 receptor antagonistic activity, procedure for the preparation thereof, compositions which contain them, and applications |
| EP0943613A4 (en) * | 1996-11-19 | 2002-07-10 | Kyowa Hakko Kogyo Kk | HETEROCYCLIC COMPOUNDS CONTAINING OXYGEN |
| US6514996B2 (en) | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| WO2006014134A1 (en) * | 2004-08-02 | 2006-02-09 | Astrazeneca Ab | Novel piperidine derivative for the treatment of depression |
-
1977
- 1977-07-08 FR FR7721088A patent/FR2396757A2/en active Granted
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2438044A2 (en) * | 1978-04-10 | 1980-04-30 | Delalande Sa | Alkylene di:oxy benzene derivs. - intermediates for cinnamoyl piperazine(s) having anti-angina activity and also effect on circulation (SW 12.11.79) |
| FR2447918A1 (en) * | 1979-02-05 | 1980-08-29 | Delalande Sa | 1-Cinnamoyl-4-phenyl-hydroxy-propyl-piperazine derivs. - used to treat angina, cardiovascular troubles and improve cerebral and peripheral circulation |
| EP0123386A1 (en) * | 1983-02-28 | 1984-10-31 | Sumitomo Chemical Company, Limited | Fungicidal N-(condensed phenyl) carbamates |
| US5175173A (en) * | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
| EP0147044A3 (en) * | 1983-12-22 | 1985-11-21 | Adria Laboratories Inc. | Benzofurancarboxamides, process for their preparation and pharmaceutical preparations containing them |
| EP0171636A1 (en) * | 1984-08-14 | 1986-02-19 | RAVIZZA S.p.A. | Pharmacologically active piperazino derivatives and the process for their preparation |
| EP0216658A1 (en) * | 1985-08-12 | 1987-04-01 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | Benzodioxepane, process for its preparation and its therapeutical use |
| FR2586018A1 (en) * | 1985-08-12 | 1987-02-13 | Ile De France | NOVEL BENZODIOXEPANNE, METHOD OF SYNTHESIS AND THERAPEUTIC APPLICATIONS |
| US4888353A (en) * | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| WO1988001866A1 (en) * | 1986-09-09 | 1988-03-24 | Adria Laboratories, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US5374637A (en) * | 1989-03-22 | 1994-12-20 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| US5576448A (en) * | 1989-03-22 | 1996-11-19 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl) (dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives |
| US5185335A (en) * | 1990-03-06 | 1993-02-09 | Janssen Pharmaceutica N.V. | N-(4-piperodinyl)(dihydrobenzofuran or dihydro-2h-benzopyran) carboxamide derivatives |
| US5262418A (en) * | 1990-03-06 | 1993-11-16 | Tanssen Pharmaceutica N.V. | N-(4-piperidinyl) (dihydroxybenzofuran or dihydro-2H-benzopyran)carboxamide derivatives |
| WO1993005038A1 (en) * | 1991-09-12 | 1993-03-18 | Smithkline Beecham Plc | 5-ht4 receptor antagonists |
| AU668102B2 (en) * | 1991-09-12 | 1996-04-26 | Smithkline Beecham Plc | 5-HT4 receptor antagonists |
| US5580885A (en) * | 1991-09-12 | 1996-12-03 | Smithkline Beecham P.L.C. | 5-HT4 receptor antagonists |
| AP373A (en) * | 1991-09-14 | 1994-12-07 | Smithkline Beecham Plc | Compounds having 5TH4 receptor antagonist activity. |
| GR920100469A (en) * | 1992-10-19 | 1994-06-30 | Smithkline Beecham Plc | Pharmaceutical substances. |
| ES2065238A1 (en) * | 1992-11-20 | 1995-02-01 | Smithkline Beecham Plc | Condensed benzene derivatives with 5-HT4 receptor antagonistic activity, procedure for the preparation thereof, compositions which contain them, and applications |
| WO1994029298A1 (en) * | 1993-06-16 | 1994-12-22 | Smithkline Beecham Plc | 8-amino-7-chloro-1,4-benzodioxan-5-carboxylic acid, -1-butyl-4-piperidinyl ester as a 5-ht4-receptor antagonist |
| US6514996B2 (en) | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| US6716987B1 (en) | 1995-05-19 | 2004-04-06 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxazole compounds |
| EP0943613A4 (en) * | 1996-11-19 | 2002-07-10 | Kyowa Hakko Kogyo Kk | HETEROCYCLIC COMPOUNDS CONTAINING OXYGEN |
| WO2006014134A1 (en) * | 2004-08-02 | 2006-02-09 | Astrazeneca Ab | Novel piperidine derivative for the treatment of depression |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2396757B2 (en) | 1980-07-25 |
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