GB1276600A - Substituted indenylacetic acids and their derivatives - Google Patents
Substituted indenylacetic acids and their derivativesInfo
- Publication number
- GB1276600A GB1276600A GB37829/70A GB3782970A GB1276600A GB 1276600 A GB1276600 A GB 1276600A GB 37829/70 A GB37829/70 A GB 37829/70A GB 3782970 A GB3782970 A GB 3782970A GB 1276600 A GB1276600 A GB 1276600A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- prepared
- alkoxy
- acid
- 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
- PTUSXMWNCXRKAX-UHFFFAOYSA-N 2-(1h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)C=CC2=C1 PTUSXMWNCXRKAX-UHFFFAOYSA-N 0.000 title 1
- -1 nitro, amino Chemical group 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 150000003935 benzaldehydes Chemical class 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 150000002148 esters Chemical class 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
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- JMNVALXGIOSFGW-UHFFFAOYSA-N 2-(3h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CCC2=C1 JMNVALXGIOSFGW-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino 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
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 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
- 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 150000003613 toluenes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
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- 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
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- 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
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
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- 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
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- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
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- 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
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- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
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- C07C59/40—Unsaturated compounds
- C07C59/74—Unsaturated compounds containing —CHO groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
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- 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
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- 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
- C07F9/54—Quaternary phosphonium compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1276600 Substituted 3-indenyl acetic acid acid derivatives MERCK & CO Inc 5 Aug 1970 [8 Aug 1969 1 May 1970] 37829/70 Heading C2C Novel compounds of the general Formula I: wherein Ar is aryl or heteroaryl; R 1 is hydrogen, alkyl or haloalkyl; R 2 hydrogen or alkyl; R 3 , R 4 , R 5 and R 6 each are hydrogen, alkyl, acyloxy, alkoxy, nitro, amino, acylamino, alkylamino dialkylamino, dialkylamino alkyl, sulphamoyl, alkylthio, mercapto, hydroxy, hydroxyl alkyl, alkyl sulphonyl, halogen, cyano, carboxyl, alkoxycarbonyl, carbamoyl, haloalkyl cycloalkyl or cycloalkoxyl; R 7 is alkyl sulphinyl or alkyl sulphonyl; R 8 is hydrogen, halogen, hydroxy, alkoxy, alkyl, haloalkyl and M is hydroxy, alkoxy, substituted alkoxy, amino, alkylamino, dialkylamino, N-morpholino, hydroxyalkylamino, polyhydroxyalkylamino, dialkylaminoalkylamino, aminoalkylamino or the group OMe, wherein Me is a cation and the alkyl and alkoxy all being C 1-5 radicals, may be prepared by oxidizing a compound I in which R 7 is alkylthio to sulphoxide and optionally oxidizing the sulphoxide to the sulphone and/or optionally forming metal salts, esters or amides and separating the isomers. The compound I in which R 7 is alkylthio may be prepared by condensing an aldehyde II with an indene III wherein R<SP>*</SP> is an alkyl thio group, and E is an esterifying group; which may in turn be prepared by reacting a halo acetate halo-CH(R 1 )- COOAlk with an indanone IV: to produce III directly or to produce a hydroxyl compound which may be dehydrated to form III. The compound IV may be prepared by cyclizing an acid Va or a reactive derivative thereof): which in turn may be prepared by hydrogenation of the α,#-unsaturated acid VI or by decarboxylation of a malonic acid ester VII: The α,#-unseturated acids VI may be formed by condensation of a substituted benzaldehyde with a substituted haloacetic acid ester, halo- CH(R 2 )COOE or acid anhydride. The malonic ester derivative VII may be prepared by condensing a substituted benzyl halide with a malonic ester R 2 CH(COOE) 2 . The substituted benzaldehyde may be prepared by bromination followed by hydrolysis of the appropriate substituted toluene or Friedel Crafts condensation of Cl 2 CHOCH 3 with the appropriate substituted benzene followed by hydrolysis. Pharmaceutical compositions of the compounds I show anti-inflammatory and analgesic activity when administered topically, orally, rectally or parenterally with the usual excipients.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US84873669A | 1969-08-08 | 1969-08-08 | |
US3389170A | 1970-05-01 | 1970-05-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1276600A true GB1276600A (en) | 1972-06-01 |
Family
ID=26710285
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB37829/70A Expired GB1276600A (en) | 1969-08-08 | 1970-08-05 | Substituted indenylacetic acids and their derivatives |
Country Status (13)
Country | Link |
---|---|
JP (3) | JPS5312512B1 (en) |
BE (1) | BE754556A (en) |
CA (1) | CA988096A (en) |
CH (1) | CH570372A5 (en) |
CY (1) | CY731A (en) |
DE (1) | DE2039426C3 (en) |
ES (1) | ES382583A1 (en) |
FR (1) | FR2068475B1 (en) |
GB (1) | GB1276600A (en) |
IE (1) | IE34425B1 (en) |
IL (1) | IL34998A (en) |
MY (1) | MY7400082A (en) |
PH (1) | PH16480A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100412057C (en) * | 2005-05-13 | 2008-08-20 | 浙江大学 | Process for preparing sulindac |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3851063A (en) * | 1972-07-21 | 1974-11-26 | Merck & Co Inc | Treatment of pain,fever or inflammation |
US4656190A (en) * | 1983-11-14 | 1987-04-07 | Merck & Co., Inc. | Indene derivatives and their use as PAF-antagonists |
DE3637156C2 (en) * | 1986-10-31 | 1995-12-21 | Hoechst Ag | Process for the preparation of fluorobenzaldehydes |
TW318184B (en) * | 1991-11-30 | 1997-10-21 | Hoechst Ag | |
WO2005054181A1 (en) * | 2003-12-01 | 2005-06-16 | Reverse Proteomics Research Institute Co., Ltd. | Novel target protein of anticancer agent and novel anticancer agent (spnal) corresponding thereto |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3325358A (en) * | 1962-06-06 | 1967-06-13 | Merck & Co Inc | Method of treating inflammation |
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0
- BE BE754556D patent/BE754556A/en not_active IP Right Cessation
-
1970
- 1970-07-27 IL IL34998A patent/IL34998A/en unknown
- 1970-07-27 CA CA089,259A patent/CA988096A/en not_active Expired
- 1970-07-28 IE IE977/70A patent/IE34425B1/en unknown
- 1970-07-31 CH CH1161870A patent/CH570372A5/xx not_active IP Right Cessation
- 1970-08-05 GB GB37829/70A patent/GB1276600A/en not_active Expired
- 1970-08-07 ES ES382583A patent/ES382583A1/en not_active Expired
- 1970-08-07 FR FR7029210A patent/FR2068475B1/fr not_active Expired
- 1970-08-07 DE DE2039426A patent/DE2039426C3/en not_active Expired
- 1970-08-08 JP JP6919070A patent/JPS5312512B1/ja active Pending
-
1971
- 1971-07-28 JP JP46056105A patent/JPS4844852B1/ja active Pending
-
1974
- 1974-03-13 CY CY73174A patent/CY731A/en unknown
- 1974-08-27 PH PH16213A patent/PH16480A/en unknown
- 1974-12-30 MY MY82/74A patent/MY7400082A/en unknown
-
1978
- 1978-01-25 JP JP630078A patent/JPS5638587B1/ja active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100412057C (en) * | 2005-05-13 | 2008-08-20 | 浙江大学 | Process for preparing sulindac |
Also Published As
Publication number | Publication date |
---|---|
ES382583A1 (en) | 1973-07-01 |
MY7400082A (en) | 1974-12-31 |
FR2068475A1 (en) | 1971-08-27 |
PH16480A (en) | 1983-10-25 |
CH570372A5 (en) | 1975-12-15 |
IL34998A (en) | 1974-09-10 |
JPS4844852B1 (en) | 1973-12-27 |
JPS5312512B1 (en) | 1978-05-01 |
CY731A (en) | 1974-03-13 |
DE2039426C3 (en) | 1975-02-20 |
JPS5638587B1 (en) | 1981-09-08 |
IE34425L (en) | 1971-02-08 |
IL34998A0 (en) | 1970-09-17 |
BE754556A (en) | 1971-02-08 |
IE34425B1 (en) | 1975-04-30 |
FR2068475B1 (en) | 1974-08-30 |
DE2039426B2 (en) | 1974-06-27 |
DE2039426A1 (en) | 1971-02-18 |
CA988096A (en) | 1976-04-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
746D | Case decided by the comptroller (sect. 46(3)/1977) | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
PE20 | Patent expired after termination of 20 years |