GB1364013A - Substituted indenylalkanols - Google Patents
Substituted indenylalkanolsInfo
- Publication number
- GB1364013A GB1364013A GB219272A GB219272A GB1364013A GB 1364013 A GB1364013 A GB 1364013A GB 219272 A GB219272 A GB 219272A GB 219272 A GB219272 A GB 219272A GB 1364013 A GB1364013 A GB 1364013A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- hydroxyalkoxy
- haloalkoxy
- haloalkyl
- 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
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 2
- 150000002469 indenes Chemical class 0.000 abstract 2
- -1 sulphamyl Chemical group 0.000 abstract 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 1
- NZSCUDBGUBVDLO-UHFFFAOYSA-N 3h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CCC2=C1 NZSCUDBGUBVDLO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/383—Cycloaliphatic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1364013 Substituted 1-(arylmethylene)indenes MERCK & CO Inc 17 Jan 1972 [21 Jan 1971] 2192/72 Heading C2C The invention comprises compounds of formula wherein R<SP>1</SP> is H, alkyl or acyl; n is 1 or 2; R 2 is H, alkyl, haloalkyl, alkenyl or alkynyl; R 4 ... R 7 are each H, alkyl, acyloxy, alkoxy, NO 2 , NH 2 , acylamino, alkylamino, dialkylamino, dialkylaminoalkyl, sulphamyl, alkylthio, SH, OH, hydroxyalkyl, alkylsulphonyl, halogen, CN, CO 2 , H, carboalkoxy, carbonyl, haloalkyl, cycloalkyl, cycloalkoxy, alkenyl or alkynyl; Ar is aryl or heteroaryl; R 8 is alkylsulphinyl or alkylsulphonyl; and R 9 is H, halogen, OH, alkoxy, haloalkyl, haloalkoxy or hydroxyalkoxy. In examples, these compounds are prepared by reacting (1) the corresponding 1-unsubstituted indene with the aldehyde R 8 R 9 ArCHO, (2) the above compound (R<SP>1</SP>=H) with an alkylating agent, (3) the above compound (R<SP>1</SP>=alkyl, R 9 =hydroxyalkoxy) with a thionyl halide, and to give the analogue (R 9 = haloalkoxy). Intermediates otherwise prepared are the methyl esters of substituted 3-indenecarboxylic acids, and MeSPh substituted as follows:- o-chloro, o-bromo, o-alkoxy, o-hydroxyalkoxy, o-haloalkoxy, and 2-chloro-4-formyl. Therapeutic compositions for oral, parenteral, rectal or topical administration, comprise compounds of the above formula, which have analgesic, antiinflammatory and antipyretic activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10862971A | 1971-01-21 | 1971-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364013A true GB1364013A (en) | 1974-08-21 |
Family
ID=22323251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB219272A Expired GB1364013A (en) | 1971-01-21 | 1972-01-17 | Substituted indenylalkanols |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5640151B1 (en) |
| CA (1) | CA1016555A (en) |
| CH (1) | CH573904A5 (en) |
| DE (1) | DE2202714A1 (en) |
| FR (1) | FR2122585B1 (en) |
| GB (1) | GB1364013A (en) |
| NL (1) | NL7200060A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142801A2 (en) * | 1983-11-14 | 1985-05-29 | Merck & Co. Inc. | Indene derivatives useful as paf-antagonists |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860636A (en) * | 1972-12-06 | 1975-01-14 | Merck & Co Inc | Substituted indenyl phosphonic acids having anti-inflammatory activity |
-
1972
- 1972-01-04 NL NL7200060A patent/NL7200060A/xx not_active Application Discontinuation
- 1972-01-11 CA CA132,196A patent/CA1016555A/en not_active Expired
- 1972-01-11 CH CH37172A patent/CH573904A5/xx not_active IP Right Cessation
- 1972-01-17 GB GB219272A patent/GB1364013A/en not_active Expired
- 1972-01-20 DE DE19722202714 patent/DE2202714A1/en active Pending
- 1972-01-21 FR FR7202067A patent/FR2122585B1/fr not_active Expired
- 1972-01-21 JP JP769372A patent/JPS5640151B1/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142801A2 (en) * | 1983-11-14 | 1985-05-29 | Merck & Co. Inc. | Indene derivatives useful as paf-antagonists |
| EP0142801A3 (en) * | 1983-11-14 | 1986-07-16 | Merck & Co. Inc. | Indene derivatives useful as paf-antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3779472A (en) | 1973-07-12 |
| NL7200060A (en) | 1972-07-25 |
| CA1016555A (en) | 1977-08-30 |
| DE2202714A1 (en) | 1972-07-27 |
| CH573904A5 (en) | 1976-03-31 |
| JPS5640151B1 (en) | 1981-09-18 |
| FR2122585A1 (en) | 1972-09-01 |
| FR2122585B1 (en) | 1975-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |