GB1174124A - Pharmacologically Active Indolizine Compounds - Google Patents
Pharmacologically Active Indolizine CompoundsInfo
- Publication number
- GB1174124A GB1174124A GB3027167A GB3027167A GB1174124A GB 1174124 A GB1174124 A GB 1174124A GB 3027167 A GB3027167 A GB 3027167A GB 3027167 A GB3027167 A GB 3027167A GB 1174124 A GB1174124 A GB 1174124A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- reacting
- indolizines
- alkyl
- group
- 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
- 125000003406 indolizinyl group Chemical class C=1(C=CN2C=CC=CC12)* 0.000 title 1
- -1 R<SP>2</SP> is H Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002478 indolizines Chemical class 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- DUNPHONTJGYDFR-UHFFFAOYSA-N 1-indolizin-1-yl-N,N-dimethylmethanamine Chemical class CN(C)CC=1C=CN2C=CC=CC=12 DUNPHONTJGYDFR-UHFFFAOYSA-N 0.000 abstract 1
- LRSNLLOKLZWSTC-UHFFFAOYSA-N 2-indolizin-1-ylacetamide Chemical class C1=CC=CC2=C(CC(=O)N)C=CN21 LRSNLLOKLZWSTC-UHFFFAOYSA-N 0.000 abstract 1
- LFEPHZUUBOQBJL-UHFFFAOYSA-N 2-indolizin-1-ylacetonitrile Chemical class C1=CC=CC2=C(CC#N)C=CN21 LFEPHZUUBOQBJL-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000000699 topical 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,174,124. Indolizine derivatives. BEECHAM GROUP Ltd. 30 Sept., 1968 [30 June, 1967], No. 30271/67. Heading C2C. The invention comprises compounds of formula wherein R<SP>1</SP> is H, a non-toxic metal ion, ammonium, quaternary ammonium or protonated amine group, or a (possibly substituted) hydrocarbon group, R<SP>2</SP> is H, alkyl, aryl or aralkyl, R<SP>3</SP> is H, alkyl, aryl, aralkyl or acyl, and X is H, alkyl or alkoxy. These compounds are prepared by reacting 1-unsubstituted indolizines (except where R<SP>3</SP>=H) with CH 2 O+HNMe 2 to give the corresponding 1-dimethylaminomethylindolizines, converting these to the methohalides, reacting the latter with KCN to obtain the 1-cyanomethylindolizines and hydrolysing the latter with alkali; in the hydrolysis stage indolizine-1- acetamides may also be isolated. Esters may be obtained by reacting the acids with CH 2 N 2 , or the acid Na salt with (e.g.) Et 2 NC 2 H 4 Cl. The compounds where R<SP>3</SP>=H are made by substituting the 1-position of a 3-acylindolizine and thereafter hydrolysing off the acyl group with acid. Starting materials.-Indolizines unsubstituted in the 1- and 3-positions are prepared by cyclizing 1 - R<SP>2</SP>COCH 2 - 2 - methylpyridinium halides with NaHCO 3 , and the products may be acylated in the 3-position to give the corresponding 3-acylindolizines. Therapeutic compositions for parenteral, oral or topical use comprise indolizines of the above formula, which have analgesic and antiinflammatory activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3027167A GB1174124A (en) | 1967-06-30 | 1967-06-30 | Pharmacologically Active Indolizine Compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3027167A GB1174124A (en) | 1967-06-30 | 1967-06-30 | Pharmacologically Active Indolizine Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1174124A true GB1174124A (en) | 1969-12-10 |
Family
ID=10305002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3027167A Expired GB1174124A (en) | 1967-06-30 | 1967-06-30 | Pharmacologically Active Indolizine Compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1174124A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0147317A3 (en) * | 1983-12-21 | 1986-06-25 | Rhone-Poulenc Sante | Ortho-condensed pyrrole derivatives, their preparation and medicaments containing them |
| US5134239A (en) * | 1984-07-17 | 1992-07-28 | The Dow Chemical Company | Latent catalysts for epoxy-phenolic reactions |
| WO1996003383A1 (en) * | 1994-07-21 | 1996-02-08 | Eli Lilly And Company | INDOLIZINE sPLA2 INHIBITORS |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| FR2805460A1 (en) * | 2000-02-25 | 2001-08-31 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING CATIONIC INDOLIZINE DERIVATIVES AND DYEING PROCESS |
| WO2006136859A3 (en) * | 2005-06-24 | 2007-04-05 | Argenta Discovery Ltd | Indoli zine derivatives and their use as crth2 antagonists |
| WO2008074966A1 (en) * | 2006-12-21 | 2008-06-26 | Argenta Discovery Limited | Crth2 antagonists |
-
1967
- 1967-06-30 GB GB3027167A patent/GB1174124A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0147317A3 (en) * | 1983-12-21 | 1986-06-25 | Rhone-Poulenc Sante | Ortho-condensed pyrrole derivatives, their preparation and medicaments containing them |
| US5134239A (en) * | 1984-07-17 | 1992-07-28 | The Dow Chemical Company | Latent catalysts for epoxy-phenolic reactions |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| WO1996003383A1 (en) * | 1994-07-21 | 1996-02-08 | Eli Lilly And Company | INDOLIZINE sPLA2 INHIBITORS |
| US6645976B1 (en) | 1994-07-21 | 2003-11-11 | Eli Lilly And Company | Indolizine SPLA2inhibitors |
| FR2805460A1 (en) * | 2000-02-25 | 2001-08-31 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING CATIONIC INDOLIZINE DERIVATIVES AND DYEING PROCESS |
| US6579326B2 (en) | 2000-02-25 | 2003-06-17 | L'oreal S.A. | Compositions for dyeing keratin fibers, containing cationic indolizine derivatives, and dyeing process |
| WO2006136859A3 (en) * | 2005-06-24 | 2007-04-05 | Argenta Discovery Ltd | Indoli zine derivatives and their use as crth2 antagonists |
| WO2008074966A1 (en) * | 2006-12-21 | 2008-06-26 | Argenta Discovery Limited | Crth2 antagonists |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |