GB1373262A - Indenyl-alkanoic acids and their derivatives - Google Patents
Indenyl-alkanoic acids and their derivativesInfo
- Publication number
- GB1373262A GB1373262A GB219572A GB219572A GB1373262A GB 1373262 A GB1373262 A GB 1373262A GB 219572 A GB219572 A GB 219572A GB 219572 A GB219572 A GB 219572A GB 1373262 A GB1373262 A GB 1373262A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- prepared
- hydroxy
- alkoxy
- indenyl
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title 1
- -1 arylidene indene derivatives Chemical class 0.000 abstract 19
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 230000005494 condensation Effects 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000004001 thioalkyl group Chemical group 0.000 abstract 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 abstract 1
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 abstract 1
- KVFUMBHERGZEGG-UHFFFAOYSA-N 3-hydroxy-4-methylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1O KVFUMBHERGZEGG-UHFFFAOYSA-N 0.000 abstract 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 abstract 1
- LVUUCFIQQHEFEJ-UHFFFAOYSA-N 6-fluoro-2,3-dihydroinden-1-one Chemical compound FC1=CC=C2CCC(=O)C2=C1 LVUUCFIQQHEFEJ-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 238000007239 Wittig reaction Methods 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 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
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 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
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 150000002469 indenes Chemical class 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1373262 Sulphoxides and sulphones of arylidene indene derivatives MERCK & CO Inc 17 Jan 1972 [21 Jan 1971] 2195/72 Heading C2C Novel cmpounds of the general Formula I wherein R 1 is (CH 2 ) p COM where p is 2, 3 or 4, or -(CH 2 ) m C(R<SP>1</SP>R)(CH 2 ) n COM where R and R<SP>1</SP> are each hydrogen, alkyl, aryl or halogen, m is 2, 1 or 0 and n is 1 or 0 provided that m+n is not 0; (Ar) is aryl or heteroaryl; R 2 is hydrogen, alkyl or haloalkyl; R 3 , R 4 , R 5 and R 6 each are hydrogen, alkyl, acyloxy, alkoxy, amino, acylamino, alkylamino, dialkylamino, dialkylaminoalkyl, sulphamyl, hydroxy, hydroxyalkyl, alkylsulphonyl, halogen, cyano, carboxyl, carboalkoxy, carbamido, haloalkyl, cycloalkyl, cycloalkoxy, alkenyloxy or acyl; R 7 is alkylsulphinyl or alkylsulphonyl; R 8 is hydrogen or halogen atom or a methyl sulphinyl, cyano, hydroxy, alkoxy, hydroxyalkoxy or haloalkoxy radical; and M is a hydroxy, C 1-6 alkoxy, substituted C 1-6 alkoxy, amino, alkylamino, dialkylamino, N-morpholino, piperidino, pyrrolidino, piperazino, N-methylpiperazino, N-phenylpiperazino, N - hydroxyethylpiperazino, aralkylamino, dibenzylamino, anilino, p-ethoxyanilino, pchloroanilino, p-fluoroanilino, p-trifluoromethylanilino, cyclohexylamino, tetra-O-acetyl-dglucosamino, N,N - dialkylcarbonylmethylamino, benzyloxycarbonylmethylamino, hydroxyalkylamino, bis - (hydroxyalkyl)amino, polyhydroxyalkylamino, alkoxyalkylamino, bis - (alkoxyalkyl)amino, dialkylaminoalkylamino or aminoalkylamino radical or a radical of formula OMe in which Me is a cation; provided that at least one of R 3 , R 4 , R 5 and R 6 is other than hydrogen, may be prepared by (1) oxidation of the corresponding compound I in which R 7 is thioalkyl; (2) interconversion of the substituted alkyl in R 1 ; (3) formation of esters and amides at COM; (4) separation of racemic mixtures into their (+) and (-) forms and isomerization into a cis or trans isomer. The intermediates I in which R 7 is thioalkyl and COM is the free acid may be prepared by condensation of a thioalkyl substituted aryl aldehyde with an appropriately substituted indene ester optionally followed by intereonversion of the substituted alkyl in the R 1 grouping and/or separation into isomers. The intermediate indene esters may be prepared by introduction of the R 1 group into the appropriate 1-indanone by a Wittig reaction with an α-triphenyl phosphinyl ester followed by rearrangement to the indene. 6-Fluoroindanone may be prepared by reaction of p-fluorobenzaldehyde with acetic anhydride and sodium acetate. Methyl 5 - fluoro - 2 - methyl - 3 - indenyl - γ- (#-hydroxybutyrate) may be prepared by reduction of methyl 5-fluoro-2-methyl indenyl-3- acetate to 5 - -fluoro - 2 - methyl - indenyl - 3- (#-ethanol) followed by oxidation to 5-fluoro-2- methyl - indenyl - 3 - acetaldehyde followed by condensation with methyl bromoacetate in the presence of zinc. o-C 1-4 -Alkoxythioanisoles may be prepared by reaction of o-chloroanisole with the appropriate sodium alkoxide in the presence of copper. Similarly various hydroxy- and halo-C 1-4 alkoxy thioanisoles may be prepared by condensation of the hydroxyalkylhalides with ohydroxythioanisole followed by halogenation of the free hydroxy group. 3 - Hydroxy - 4 - methylthiobenzaldehyde may be prepared by reaction of o-hydroxythioanisole with dichloromethyl methyl ether in the presence of aluminium chloride. Pharmaceutical compositions of the compounds I show anti-inflammatory, analgesic and antipyretic activity when administered topically, orally, parenterally or rectally with the-usual excipients.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10862871A | 1971-01-21 | 1971-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1373262A true GB1373262A (en) | 1974-11-06 |
Family
ID=22323240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB219572A Expired GB1373262A (en) | 1971-01-21 | 1972-01-17 | Indenyl-alkanoic acids and their derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU469140B2 (en) |
| CA (1) | CA990734A (en) |
| CH (1) | CH573905A5 (en) |
| DE (1) | DE2202729A1 (en) |
| FR (1) | FR2122588B1 (en) |
| GB (1) | GB1373262A (en) |
| NL (1) | NL7200059A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9309621D0 (en) * | 1993-05-11 | 1993-06-23 | Wellcome Found | Amide derivatives and their therapeutic use |
| US6124284A (en) * | 1998-07-16 | 2000-09-26 | Glaxo Wellcome Inc. | Bicyclic amide derivatives and their use as muscle relaxants |
-
1972
- 1972-01-04 NL NL7200059A patent/NL7200059A/xx not_active Application Discontinuation
- 1972-01-11 CH CH37472A patent/CH573905A5/xx not_active IP Right Cessation
- 1972-01-11 CA CA132,199A patent/CA990734A/en not_active Expired
- 1972-01-11 AU AU37795/72A patent/AU469140B2/en not_active Expired
- 1972-01-17 GB GB219572A patent/GB1373262A/en not_active Expired
- 1972-01-20 DE DE19722202729 patent/DE2202729A1/en active Pending
- 1972-01-21 FR FR7202070A patent/FR2122588B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2122588B1 (en) | 1975-08-01 |
| AU3779572A (en) | 1973-07-12 |
| AU469140B2 (en) | 1976-02-05 |
| CA990734A (en) | 1976-06-08 |
| FR2122588A1 (en) | 1972-09-01 |
| NL7200059A (en) | 1972-07-25 |
| CH573905A5 (en) | 1976-03-31 |
| DE2202729A1 (en) | 1972-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |