HU179064B - Process for preparing 2,3-alkylene-bis-/oxy/-benzamides - Google Patents
Process for preparing 2,3-alkylene-bis-/oxy/-benzamidesInfo
- Publication number
- HU179064B HU179064B HUSO001195A HU179064B HU 179064 B HU179064 B HU 179064B HU SO001195 A HUSO001195 A HU SO001195A HU 179064 B HU179064 B HU 179064B
- Authority
- HU
- Hungary
- Prior art keywords
- substd
- opt
- alkyl
- alkenyl
- forms
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- 125000003342 alkenyl group Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 4
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- -1 cycloalkenylalkyl Chemical group 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
- 125000003441 thioacyl group Chemical group 0.000 abstract 2
- VCLSWKVAHAJSFL-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-5-carboxylic acid Chemical compound O1CCOC2=C1C=CC=C2C(=O)O VCLSWKVAHAJSFL-UHFFFAOYSA-N 0.000 abstract 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000003474 anti-emetic effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 230000002903 catalepsic effect Effects 0.000 abstract 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 abstract 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
- 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
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- 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
- A61P25/20—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
2,3-Alkylenedioxybenzamides of formula (I) and their acid -addn. salts, quat. ammonium salts, oxides and optical isomers are new. In (I), A is 1-3C alkylene opt. substd by 1-4C alkyl, 2-4C alkenyl or 1-4C hydroxyalkyl. R is H, 1-4C alkyl or -B-NR1R2; B is a direct bond or a 1-3C alkylene gp. opt. substd. by 1-4C alkyl or 2-4C alkenyl; R1 is H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, substd. alkyl, or forms a heterocyclic ring with B, and R2 is H, 1-4C alkyl, 2-4C alkenyl or alkynyl, substd. alkyl, an opt. substd. heterocyclic gp., or a phenyl, adamantyl, cycloalkyl, bicycloalkyl or cycloalkenyl gp. bonded directly to the N atom or via an opt. substd. alkylene chain, or NR1R2 is a heterocycle opt. contg. other heteroatoms (including NR'', where R'' is H- 1-4C alkyl, 2-4C alkenyl or alkynyl, phenyl, benzyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, adamantyl, bicycloalkyl or alkyl substd by OH, SH, acyl, thioacyl, alkoxy or alkylthio). - R' is H, 1-4c alkyl, 2-4C alkenyl or alkynyl, adamantyl, pyrimidinyl, pyrazinyl, diazepinyl, quinuclidinyl, azabicycloalkyl, diazabicycloalkyl, bicycloalkyl, or opt. substd. phenyl or aralkyl, or R'+B forms an opt. substd. heterocycle contg. a single N atom, or R'+R1 forms an opt. substd. heterocycle contg. two heteroatoms, X is H, halogen, OH, 1-4C alkoxy, 1-4C alkyl, amino opt. mono- or disubstd. by 1-4C alkyl, acyl, aralkyl, furyl, pyranyl or alkoxycacarbonyl, or forms an A' chain with Y. Y is as defined for X or is NO2, 1-4C alkylsulphonyl, adamantyl-sulphonyl, cycloalkyl sulphonyl or SO2NR3R'; R3 and R4 are H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, phenyl, benzyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, bicycloalkyl, adamantyl, pyrimidinyl, pyrazinyl, or alkyl substd. by OH, SH, acyl, thioacyl, alkoxy or alkylthio, or NR3R4 is an opt. substd. heterocycle opt. congt. another heteroatom; or Y forms an A chain with X or Z. Z is as defined for X or is NO2, or forms an A chain with Y. A is a carbon chain opt. substd. or opt. interrupted by one or more opt. substd. heteroatoms. - Cpds. (I) have anxiolytic, antidepressant and antiemetic activity with little or no cataleptic activity. A typical cpd. of N-(1-allyl-2-pyrrolidinylmethyl)-7-methylsulphamoyl-1, 4-benzodioxan-5-carboxamide. In an example, this is prepd. from 1,4-benzodioxan-5-carboxylic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7623835A FR2360305A1 (en) | 1976-08-04 | 1976-08-04 | NEW 2,3-ALKYLENE BIS (OXY) BENZAMIDE SUBSTITUTES, THEIR DERIVATIVES AND THEIR PREPARATION METHODS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU179064B true HU179064B (en) | 1982-08-28 |
Family
ID=9176558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUSO001195 HU179064B (en) | 1976-08-04 | 1977-08-03 | Process for preparing 2,3-alkylene-bis-/oxy/-benzamides |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS57167914A (en) |
| AR (1) | AR219709A1 (en) |
| AT (1) | AT358034B (en) |
| AU (1) | AU516033B2 (en) |
| BE (1) | BE857350A (en) |
| BG (1) | BG36496A3 (en) |
| CA (1) | CA1114371A (en) |
| CH (1) | CH629198A5 (en) |
| CS (1) | CS216246B2 (en) |
| DD (1) | DD133237A5 (en) |
| DE (1) | DE2760414C2 (en) |
| DK (1) | DK152366C (en) |
| EG (1) | EG12716A (en) |
| ES (1) | ES461175A1 (en) |
| FI (1) | FI63938C (en) |
| GR (1) | GR61351B (en) |
| HK (2) | HK40382A (en) |
| HU (1) | HU179064B (en) |
| IE (2) | IE45646B1 (en) |
| IL (2) | IL52644A0 (en) |
| IN (1) | IN145473B (en) |
| LU (1) | LU77897A1 (en) |
| MC (1) | MC1154A1 (en) |
| MW (1) | MW2077A1 (en) |
| NL (1) | NL172063C (en) |
| NO (1) | NO152133C (en) |
| NZ (1) | NZ184816A (en) |
| OA (1) | OA05728A (en) |
| PH (3) | PH22114A (en) |
| PL (1) | PL111071B1 (en) |
| PT (1) | PT66865B (en) |
| RO (1) | RO72963A (en) |
| SE (2) | SE440776B (en) |
| SU (1) | SU716523A3 (en) |
| YU (1) | YU40005B (en) |
| ZA (1) | ZA774701B (en) |
| ZM (1) | ZM6077A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027098D0 (en) * | 1990-12-13 | 1991-02-06 | Beecham Group Plc | Pharmaceuticals |
| US10083697B2 (en) | 2015-05-27 | 2018-09-25 | Google Llc | Local persisting of data for selectively offline capable voice action in a voice-enabled electronic device |
| JP6452575B2 (en) * | 2015-08-19 | 2019-01-16 | 株式会社トクヤマ | Manufacturing method of mirtazapine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1473829A (en) * | 1964-06-09 | 1967-03-24 | Ile De France | Nu- (tertiary-aminoalkyl) -methylene dioxybenzamides and their preparation |
-
1977
- 1977-07-11 MC MC771250A patent/MC1154A1/en unknown
- 1977-07-29 PT PT6686577A patent/PT66865B/en unknown
- 1977-07-29 ES ES461175A patent/ES461175A1/en not_active Expired
- 1977-07-29 BG BG037047A patent/BG36496A3/en unknown
- 1977-07-29 IN IN1165/CAL/77A patent/IN145473B/en unknown
- 1977-07-29 DE DE19772760414 patent/DE2760414C2/de not_active Expired - Fee Related
- 1977-07-29 GR GR54066A patent/GR61351B/en unknown
- 1977-08-01 YU YU188277A patent/YU40005B/en unknown
- 1977-08-01 BE BE1008313A patent/BE857350A/en not_active IP Right Cessation
- 1977-08-01 OA OA56243A patent/OA05728A/en unknown
- 1977-08-01 AU AU27507/77A patent/AU516033B2/en not_active Expired
- 1977-08-02 RO RO9124577A patent/RO72963A/en unknown
- 1977-08-02 EG EG45577A patent/EG12716A/en active
- 1977-08-02 LU LU77897A patent/LU77897A1/xx unknown
- 1977-08-02 IE IE1600/77A patent/IE45646B1/en not_active IP Right Cessation
- 1977-08-02 AT AT569677A patent/AT358034B/en not_active IP Right Cessation
- 1977-08-02 IE IE2409/80A patent/IE45647B1/en not_active IP Right Cessation
- 1977-08-03 MW MW2077A patent/MW2077A1/en unknown
- 1977-08-03 SE SE7708849A patent/SE440776B/en not_active IP Right Cessation
- 1977-08-03 NO NO772739A patent/NO152133C/en unknown
- 1977-08-03 CH CH956277A patent/CH629198A5/en not_active IP Right Cessation
- 1977-08-03 HU HUSO001195 patent/HU179064B/en not_active IP Right Cessation
- 1977-08-03 DK DK346977A patent/DK152366C/en not_active IP Right Cessation
- 1977-08-03 IL IL52644A patent/IL52644A0/en not_active IP Right Cessation
- 1977-08-03 DD DD20042077A patent/DD133237A5/en not_active IP Right Cessation
- 1977-08-03 ZA ZA00774701A patent/ZA774701B/en unknown
- 1977-08-03 CA CA283,994A patent/CA1114371A/en not_active Expired
- 1977-08-03 NZ NZ18481677A patent/NZ184816A/en unknown
- 1977-08-03 NL NL7708616A patent/NL172063C/en not_active IP Right Cessation
- 1977-08-04 CS CS775179A patent/CS216246B2/en unknown
- 1977-08-04 ZM ZM6077A patent/ZM6077A1/en unknown
- 1977-08-04 PH PH20078A patent/PH22114A/en unknown
- 1977-08-04 FI FI772362A patent/FI63938C/en not_active IP Right Cessation
- 1977-08-04 SU SU772507701A patent/SU716523A3/en active
- 1977-08-04 PL PL1977200066A patent/PL111071B1/en not_active IP Right Cessation
- 1977-08-08 AR AR26867377A patent/AR219709A1/en active
-
1981
- 1981-03-25 PH PH25426-AA patent/PH18629A/en unknown
- 1981-08-07 PH PH26025A patent/PH17710A/en unknown
-
1982
- 1982-03-19 JP JP4547682A patent/JPS57167914A/en active Granted
- 1982-06-25 IL IL66138A patent/IL66138A0/en not_active IP Right Cessation
- 1982-09-16 HK HK40382A patent/HK40382A/en unknown
- 1982-09-16 HK HK40482A patent/HK40482A/en unknown
- 1982-11-17 SE SE8206546A patent/SE453390B/en not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |