GB1416467A - Azaindole fused heterocyclic compounds - Google Patents
Azaindole fused heterocyclic compoundsInfo
- Publication number
- GB1416467A GB1416467A GB1985273A GB1985273A GB1416467A GB 1416467 A GB1416467 A GB 1416467A GB 1985273 A GB1985273 A GB 1985273A GB 1985273 A GB1985273 A GB 1985273A GB 1416467 A GB1416467 A GB 1416467A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- alkyl
- prepared
- methyl
- 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
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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1416467 Pyrido - pyrrolo - indolizines and -quinolizines AMERICAN HOME PRODUCTS CORP 26 April 1973 [1 May 1972 28 Aug 1972] 19852/73 Heading C2C The invention comprises compounds of the Formulae (I) and (Ia) (in which R is H, C 1-5 alkyl or allyl, R<SP>1</SP> is methyl, ethyl or n-propyl, R<SP>2</SP> is C 1-5 alkyl or allyl, X is two hydrogen atoms or an oxo group and n is 1 or 2) and pharmaceutically acceptable acid addition salts thereof. The compounds (I) in which R is H or C 1-5 alkyl and X is oxo, are prepared by reacting a compound of the Formula (II) in which R<SP>3</SP> is H or C 1-5 alkyl, with a keto-acid of formula or with an enol lactone of the Formula (III) and, if necessary, cyclizing a resulting ketoamide of the Formula (IV) The compounds (I) in which R is H or C 1-5 alkyl and X is two hydrogen atoms, are prepared by (a) reducing a compound of the Formula (V) in which W is O or S, or (b) reacting a compound of the Formula (VI) with a compound of the Formula (VII) and, if necessary, cyclizing a resulting intermediate hydrazone. The compounds (I) in which R is C 1-5 alkyl or allyl are prepared by alkylation or allylation of a corresponding compound in which R is H. The compounds of the Formula (Ia) are prepared by oxidizing a compound (I) in which R is alkyl or allyl and X is two hydrogen atoms, with a peroxy acid. Compounds (I) can exist as optical enantiomorphs and the pure enantiomorphs can be obtained by carrying out a resolution at any convenient stage of the synthesis or by resolving the final products. Thiones of Formula (V) are prepared from the corresponding ketones by reaction with P 2 S 5 . 1,2,3,6,7,8a - Hexahydro - 8a - methylindolizin-8(5H)-one is prepared by reacting 2-methylproline with thionyl chloride and methanol to give methyl 2-methyl-2-pyrrolidinecarboxylate, reacting this with methyl 4-chlorobutyrate to give methyl 2-methoxycarbonyl-2- methyl - 1 - pyrrolidine - butyrate, and reacting this with sodium methoxide to give the desired product. N - methyl - N - 2 - pyridylhydrazine is prepared by reacting 2-bromopyridine with N-methylhydrazine. Pharmaceutical compositions having analgesic activity, for oral or parenteral administration, comprise a compound (I) in which X is two hydrogen atoms, or a compound (Ia), or a pharmaceutically acceptable addition salt thereof, together with a pharmaceutical carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24899972A | 1972-05-01 | 1972-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1416467A true GB1416467A (en) | 1975-12-03 |
Family
ID=22941611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1985273A Expired GB1416467A (en) | 1972-05-01 | 1973-04-26 | Azaindole fused heterocyclic compounds |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | ATA378073A (en) |
| AU (1) | AU469004B2 (en) |
| BE (1) | BE798941A (en) |
| GB (1) | GB1416467A (en) |
| ZA (1) | ZA732881B (en) |
-
1973
- 1973-04-26 GB GB1985273A patent/GB1416467A/en not_active Expired
- 1973-04-27 ZA ZA732881A patent/ZA732881B/en unknown
- 1973-04-27 AT AT378073A patent/ATA378073A/en not_active IP Right Cessation
- 1973-04-27 AU AU54919/73A patent/AU469004B2/en not_active Expired
- 1973-04-30 BE BE130608A patent/BE798941A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE798941A (en) | 1973-10-30 |
| ZA732881B (en) | 1974-12-24 |
| ATA378073A (en) | 1976-07-15 |
| AU5491973A (en) | 1974-10-31 |
| AU469004B2 (en) | 1976-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |