ES345735A1 - New pyrazino[1,2-a]quinolines and process for preparing same - Google Patents
New pyrazino[1,2-a]quinolines and process for preparing sameInfo
- Publication number
- ES345735A1 ES345735A1 ES345735A ES345735A ES345735A1 ES 345735 A1 ES345735 A1 ES 345735A1 ES 345735 A ES345735 A ES 345735A ES 345735 A ES345735 A ES 345735A ES 345735 A1 ES345735 A1 ES 345735A1
- Authority
- ES
- Spain
- Prior art keywords
- pyrazino
- hexahydro
- quinoline
- chloride
- compound
- 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.)
- Expired
Links
- FXNGILFJMJFFBM-UHFFFAOYSA-N 1h-pyrazino[1,2-a]quinoline Chemical class C1=CC=C2N3CC=NC=C3C=CC2=C1 FXNGILFJMJFFBM-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 239000000543 intermediate Substances 0.000 abstract 9
- -1 p-methoxybenzoyl chloride 3 - (p - chlorobenzoyl) - 2,3,4,4a,5,6 - hexahydro- 1H pyrazino [1,2-a] quinoline Chemical compound 0.000 abstract 8
- CHIINPDGHUONJZ-UHFFFAOYSA-N 2,3,4,4a,5,6-hexahydro-1h-pyrazino[1,2-a]quinoline Chemical class C1=CC=C2N3CCNCC3CCC2=C1 CHIINPDGHUONJZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- SEGQXSVTXMMYNS-UHFFFAOYSA-N 1,2,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-3-yl(furan-2-yl)methanone Chemical compound O1C(=CC=C1)C(=O)N1CC2N(C3=CC=CC=C3CC2)CC1 SEGQXSVTXMMYNS-UHFFFAOYSA-N 0.000 abstract 1
- MTSSOURQBWGLJV-UHFFFAOYSA-N 1-(1,2,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-3-yl)-2-phenylethanone Chemical compound C1(=CC=CC=C1)CC(=O)N1CC2N(C3=CC=CC=C3CC2)CC1 MTSSOURQBWGLJV-UHFFFAOYSA-N 0.000 abstract 1
- SAPAWHGNIMQFMR-UHFFFAOYSA-N 1-(1,2,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-3-yl)ethanone Chemical compound C1=CC=C2N3CCN(C(=O)C)CC3CCC2=C1 SAPAWHGNIMQFMR-UHFFFAOYSA-N 0.000 abstract 1
- NTIJTEBBAZRBAW-UHFFFAOYSA-N 1-benzoyl-6-methyl-2h-quinoline-2-carbonitrile Chemical compound N#CC1C=CC2=CC(C)=CC=C2N1C(=O)C1=CC=CC=C1 NTIJTEBBAZRBAW-UHFFFAOYSA-N 0.000 abstract 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 abstract 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 abstract 1
- XODLSVZKRPBFLU-UHFFFAOYSA-N N-[(6-methoxy-1,2,3,4-tetrahydroquinolin-2-yl)methyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC1NC2=CC=C(C=C2CC1)OC XODLSVZKRPBFLU-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000006264 debenzylation reaction Methods 0.000 abstract 1
- JRVKTGJDUJGQEM-UHFFFAOYSA-N furan-2-yl-(8-methyl-1,2,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-3-yl)methanone Chemical compound O1C(=CC=C1)C(=O)N1CC2N(C3=CC=C(C=C3CC2)C)CC1 JRVKTGJDUJGQEM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Novel 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinolines [I] in which the carbon atoms of the hetero rings are unsubstituted or alkylated and which contain in the 3-position a radical R which may be aliphatic, cycloaliphatic, cycloaliphatic - aliphatic, araliphatic or heterocyclic - aliphatic and in which the aromatic or heterocyclic rings of R may be further substituted by -CF 3 , C 1-7 alkyl, C 1-7 alkoxy or halogen atoms and their salts are prepared by (a) reacting the appropriate 3-unsubstituted compound with a compound R-X, where X is halo or an arylsulphonyloxy group, (b) reducing with lithium aluminium hydride a 3-R-2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline in which at least one of the ring carbon atoms 1, 2 or 4 or a carbon atom outside the ring, which, owing to the vicinity of a N atom is capable of forming an amidic oxo group carries an amidic oxo group, or (c) when R is a heterocyclyl-alkyl radical reacting the appropriate 3-unsubstituted compound with a heterocyclic compound which is substituted by an optionally alkylated vinyl radical and in which the double bond of the vinyl group is activated by the heterocyclic portion. Intermediates prepared are 1 - chloroacetyl - 2- (benzoylaminomethyl)- 1,2,3,4 - tetrahydro-quinoline from the chloroacetylation of the appropriate 1-unsubstituted compound 1-oxo-3- benzoyl - 1,2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the former-named intermediate 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline by debenzylation of the 3-benzyl derivative 3-(p-methoxy-henzoyl) - 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline by reaction of the former-named intermediate with p-methoxybenzoyl chloride 3 - (p - chlorobenzoyl) - 2,3,4,4a,5,6 - hexahydro- 1H pyrazino [1,2-a] quinoline from the 3- unsubstituted compound and p-chlorobenzoyl chloride 3 - (p - toluoyl) - 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the 3-unsubstituted compound and p-toluoyl chloride 2 - (benzoylaminomethyl)- 6 - methyl-1,2,3,4- tetrahydroquinoline from 1 - benzoyl - 2 - cyano- 6 - methyl - 1,2 - dihydroquinoline by hydrogenation 1 - chloroacetyl - 2 - {benzoylaminomethyl) - 6 - methyl - 1,2,3,4 - tetrahydroquinoline from the previously-named intermediate and chloroacetyl chloride 1-oxo-3-benzoyl- 8-methyl- 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the former intermediate 1 - chloroacetyl - 2 - (benzoylaminomethyl) - 6 - methoxy- 1 ,2,3,4-tetrahydroquinoline from 2-(benzoylaminomethyl) - 6 - methoxy - 1,2,3,4 - tetrahydroquinoline and chloroacetyl chloride 1 -oxo- 3 - benzoyl - 8 - methoxy - 2,3,4,4a, 5,6 - hexahydro- 1H - pyrazino [1,2-a] quinoline from the last named intermediate 3 - phenylacetyl - 2,3,4,4a, 5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline and phenylacetyl chloride 3 - (# phenylpropionyl) - 2,3,4,4a,5,6 - hexahydro- 1H - pyrazino [1,2-a] quinoline in a similar manner to the last-named intermediate 3-(2- furoyl) - 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the appropriate 3-unsubstituted compound and furan-2-carboxylic acid chloride 3 - (2 - thenoyl) - 2,3,4,4a,5,6 - hexahydro- 1H - pyrazino [1,2-a] quinoline in a similar manner to the last-named intermediate 3- acetyl - 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the appropriate 3-unsubstituted compound and acetic anhydride 3- butyryl - 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline in a similar manner to the lastnamed intermediate and 3-(2-furoyl)-8-methyl- 2,3,4,4a,5,6 - hexahydro - 1H - pyrazino [1,2-a] quinoline from the 3-unsubstituted compound and furan-2-carboxylic acid chloride. Pharmaceutical compositions comprise a novel compound [I] in conjunction with a suitable excipient for oral, rectal or parenteral administration and are effective as antihypertonics and sedatives.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1436366A CH493546A (en) | 1966-10-05 | 1966-10-05 | Pyrazino 1 2-a quinolines having adrenolytic sedative and esp antitype - rtensive activity |
CH156167 | 1967-02-02 | ||
CH1136267 | 1967-08-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES345735A1 true ES345735A1 (en) | 1969-01-16 |
Family
ID=27173075
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES345735A Expired ES345735A1 (en) | 1966-10-05 | 1967-10-04 | New pyrazino[1,2-a]quinolines and process for preparing same |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE704690A (en) |
DE (1) | DE1670473A1 (en) |
ES (1) | ES345735A1 (en) |
FR (3) | FR1549373A (en) |
GB (1) | GB1143039A (en) |
GR (1) | GR36369B (en) |
NL (1) | NL6713503A (en) |
-
1967
- 1967-09-27 DE DE19671670473 patent/DE1670473A1/en active Pending
- 1967-10-03 FR FR1549373D patent/FR1549373A/fr not_active Expired
- 1967-10-03 GB GB45003/67A patent/GB1143039A/en not_active Expired
- 1967-10-04 NL NL6713503A patent/NL6713503A/xx unknown
- 1967-10-04 GR GR670136369A patent/GR36369B/en unknown
- 1967-10-04 ES ES345735A patent/ES345735A1/en not_active Expired
- 1967-10-04 BE BE704690D patent/BE704690A/xx unknown
- 1967-12-29 FR FR134279A patent/FR7109M/fr not_active Expired
- 1967-12-29 FR FR134278A patent/FR7108M/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR7108M (en) | 1969-07-15 |
BE704690A (en) | 1968-04-04 |
FR1549373A (en) | 1968-12-13 |
DE1670473A1 (en) | 1971-02-11 |
NL6713503A (en) | 1968-04-08 |
GR36369B (en) | 1969-02-04 |
GB1143039A (en) | 1969-02-19 |
FR7109M (en) | 1969-07-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3075992A (en) | Esters of indoles | |
JPS63310886A (en) | Thiadiazinone compound | |
MXPA02000730A (en) | N (indolcarbonyl )piperazin derivatives als 5 ht2a receptor ligands. | |
WO2005077912A1 (en) | Indazole compound and pharmaceutical use thereof | |
US4824852A (en) | Substituted indole compounds which have useful effects on the central nervous system | |
WO1987007607A1 (en) | PYRANO (3,2-c) PYRIDINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM | |
RU2042677C1 (en) | Derivatives of 1,8-benzo-[b]-naphthiridine or their salts with metals, nitrogen bases or acids, or their hydrates showing antibacterial activity | |
GB1166538A (en) | Substituted Tetrahydroquinolines | |
US3772301A (en) | (4-substituted)4-(methylsulfinyl)methylcarbostyrils | |
ES345735A1 (en) | New pyrazino[1,2-a]quinolines and process for preparing same | |
ES2006622A6 (en) | 5,6,7,8-Tetrahydro-naphtho [2,3b]-2,3-dihydrofuran and 6,7,8,9-tetrahydro-5H-benzocyclohepta [2,3b]-2,3-dihydro furan tricyclic amine derivatives, processes for their preparation and pharmaceutical compositions containing them. | |
US3574216A (en) | Quaternary 3-pyridinium-2-quinolones | |
GB1423741A (en) | Derivatives of cephalosporin processes for their preparation and compositions incorporating them | |
JPS61152682A (en) | Pyridonecarboxylic acid derivative, its ester and salt | |
JP2000508299A (en) | Substituted quinoline derivatives having antiviral activity | |
GB1238106A (en) | ||
IL22791A (en) | Tetrahydro indenopyridine compounds | |
US3542785A (en) | 2-hydroxy-4-aryl-quinolines | |
GB1125112A (en) | New derivatives of diazabicyclo-decane and process for preparing them | |
AU671814B2 (en) | Nitroquinolone derivatives as NMDA antagonists | |
GB1374310A (en) | Dipyrazolo 3,4-b-3,4,-d- pyridin-3-ones | |
Kukolja | Chemistry of cephalosporin antibiotics. XX. Synthesis and biological properties of 3-acyloxymethyl-7-[2-(thienyl) acetamido]-3-cephem-4-carboxylic acid and related derivatives | |
GB1236634A (en) | New pyrimidine derivatives | |
JPS51136678A (en) | Process for preparing 5-((2-alkylamino-1-hydroxy)alkyl) carbostyril de rivatives | |
GB1432577A (en) | Substituted indolin-2-ones |