GB1477734A - Quinolines - Google Patents
QuinolinesInfo
- Publication number
- GB1477734A GB1477734A GB2721474A GB2721474A GB1477734A GB 1477734 A GB1477734 A GB 1477734A GB 2721474 A GB2721474 A GB 2721474A GB 2721474 A GB2721474 A GB 2721474A GB 1477734 A GB1477734 A GB 1477734A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- possibly
- substituted
- arch
- june
- 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
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- SLHCMPVPVQSTBV-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=C1 SLHCMPVPVQSTBV-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 230000003257 anti-anginal effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1477734 Pyrroloquinoline derivatives E R SQUIBB & SONS Inc 19 June 1974 [28 June 1973] 27214/74 Heading C2C The invention comprises the compounds (I) and their acid addition salts (Ia) wherein Aryl (Ar) is Ph or naphthyl, possibly substituted by R, RO, (R) 2 N, halogen or CF 3 (R being C 1-8 alkyl); R 1 and R 2 are each H, R (possibly Ar-substituted), up to C 8 alkenyl (possibly Ar-substituted), or Ar; and X is the anion of the acid (HX) forming the addition salt. These compounds are prepared by LiAlH 4 reduction of the triketone (V) and optionally converting the thus-formed (I) into (II). Compounds V are prepared by reacting a 2-ArCH: CH - 4,5 - dihydro - N - R 2 - 6 - pyridone (which for practical purposes is formed in situ under the reaction conditions from a 2-ArCH:CH- 2-hydroxy-N-R 2 -6-piperidone) with either (a) an N-R 1 -maleimide, or (b) maleic anhydride, followed by reaction of the resultant 2-oxa-analogue of V with (R 1 )NH 2 . Therapeutic compositions having antiinflammatory, antianginal and antiarrhythmic activity comprises compounds of the above formula and are preferably administered orally, although parenteral and rectal routes are also mentioned.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US374593A US3891652A (en) | 1973-06-28 | 1973-06-28 | Antianginal aryldecahydropyrrolo{8 3,4-f{9 quinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1477734A true GB1477734A (en) | 1977-06-22 |
Family
ID=23477494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2721474A Expired GB1477734A (en) | 1973-06-28 | 1974-06-19 | Quinolines |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3891652A (en) |
| JP (1) | JPS5040595A (en) |
| DE (1) | DE2431201A1 (en) |
| FR (1) | FR2350841A1 (en) |
| GB (1) | GB1477734A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235909A (en) * | 1979-04-19 | 1980-11-25 | Eli Lilly And Company | Octahydro-2H-pyrrolo[3,4-g]quinolines |
| US4282362A (en) * | 1979-04-19 | 1981-08-04 | Eli Lilly And Company | Octahydro-2H-pyrrolo[3,4-g]quinolines |
| US4311844A (en) * | 1980-04-18 | 1982-01-19 | Eli Lilly And Company | Octahydro-2H-pyrrolo[3,4,-g]quinolines |
| BE895842A (en) * | 1982-02-12 | 1983-08-08 | Sandoz Sa | NOVEL ERGOPEPTIDE ALKALOIDS, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
| JP2005222832A (en) * | 2004-02-06 | 2005-08-18 | Sumitomo Electric Ind Ltd | Cable manufacturing method and manufacturing apparatus |
-
1973
- 1973-06-28 US US374593A patent/US3891652A/en not_active Expired - Lifetime
-
1974
- 1974-06-19 GB GB2721474A patent/GB1477734A/en not_active Expired
- 1974-06-27 FR FR7422485A patent/FR2350841A1/en active Granted
- 1974-06-28 JP JP49074922A patent/JPS5040595A/ja active Pending
- 1974-06-28 DE DE2431201A patent/DE2431201A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2350841A1 (en) | 1977-12-09 |
| DE2431201A1 (en) | 1975-01-16 |
| FR2350841B1 (en) | 1978-12-29 |
| US3891652A (en) | 1975-06-24 |
| JPS5040595A (en) | 1975-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |