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GB2004870A - 3-[2-Hydroxy-1-(substituted) phenyl]cycloalkanone and cycloalkanol analgesic agents and intermediates therefor - Google Patents

3-[2-Hydroxy-1-(substituted) phenyl]cycloalkanone and cycloalkanol analgesic agents and intermediates therefor

Info

Publication number
GB2004870A
GB2004870A GB7836418A GB7836418A GB2004870A GB 2004870 A GB2004870 A GB 2004870A GB 7836418 A GB7836418 A GB 7836418A GB 7836418 A GB7836418 A GB 7836418A GB 2004870 A GB2004870 A GB 2004870A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
substituted
cycloalkanone
cycloalkanol
phenyl
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.)
Granted
Application number
GB7836418A
Other versions
GB2004870B (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Corp Belgium
Pfizer Inc
Original Assignee
Pfizer Corp Belgium
Pfizer Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pfizer Corp Belgium, Pfizer Inc filed Critical Pfizer Corp Belgium
Publication of GB2004870A publication Critical patent/GB2004870A/en
Application granted granted Critical
Publication of GB2004870B publication Critical patent/GB2004870B/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • 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
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • 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
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/95—Esters of quinone carboxylic acids
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is OH, alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, are useful as CNS agents especially as analgesics, tranquilisers, sedatives and antianxiety agents and/or as anticonvulsants, diuretics and antidiarrheal agents.
GB7836418A 1977-09-13 1978-09-12 3-(2-hydroxy-4 - (substituted)phenyl) cycloalkanone and cycloalkanol analgesic agents and intermediates therefor Expired GB2004870B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83310277A 1977-09-13 1977-09-13
US92668778A 1978-07-25 1978-07-25

Publications (2)

Publication Number Publication Date
GB2004870A true GB2004870A (en) 1979-04-11
GB2004870B GB2004870B (en) 1982-01-20

Family

ID=27125579

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7836418A Expired GB2004870B (en) 1977-09-13 1978-09-12 3-(2-hydroxy-4 - (substituted)phenyl) cycloalkanone and cycloalkanol analgesic agents and intermediates therefor

Country Status (27)

Country Link
JP (1) JPS5448741A (en)
AR (1) AR224618A1 (en)
AT (1) AT361455B (en)
AU (1) AU513523B2 (en)
CA (1) CA1110261A (en)
CH (1) CH635812A5 (en)
DE (1) DE2839836C2 (en)
DK (1) DK400878A (en)
ES (3) ES473288A1 (en)
FI (1) FI66584C (en)
FR (1) FR2402639A1 (en)
GB (1) GB2004870B (en)
GR (1) GR74134B (en)
HK (1) HK13284A (en)
IE (1) IE47187B1 (en)
IL (1) IL55556A (en)
IN (1) IN150334B (en)
IT (1) IT1099054B (en)
KE (1) KE3352A (en)
LU (1) LU80220A1 (en)
MX (1) MX5306E (en)
MY (1) MY8500094A (en)
NL (2) NL7809274A (en)
NO (2) NO149426C (en)
NZ (1) NZ188391A (en)
PH (2) PH15252A (en)
SE (1) SE431085B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049953A3 (en) * 1980-09-19 1982-12-08 Pfizer Inc. 4-(substituted phenyl)-naphthalen-2(1h)-ones and 2-ols, processes for their preparation, and pharmaceutical compositions containing them
EP0048572A3 (en) * 1980-09-19 1982-12-08 Pfizer Inc. Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
FR2527203A1 (en) * 1982-05-18 1983-11-25 Mitsui Toatsu Chemicals NOVEL ALKYLAROMATIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, INSECTICIDAL AGENTS AND ACARICIDES CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS
US4736057A (en) * 1983-11-11 1988-04-05 Imperial Chemical Industries Plc Cyclohexane derivatives
CN109369514A (en) * 2018-12-10 2019-02-22 天津科技大学 A kind of synthetic method of six-membered carbon ring derivative

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5650270A (en) * 1982-02-01 1997-07-22 Northeastern University Molecular analytical release tags and their use in chemical analysis
US4709016A (en) * 1982-02-01 1987-11-24 Northeastern University Molecular analytical release tags and their use in chemical analysis
IL75480A0 (en) * 1985-06-11 1985-10-31 Yissum Res Dev Co Alkoxyphenol derivatives and pharmaceutical compositions containing them
US4623657A (en) * 1985-09-05 1986-11-18 Hoechst-Roussel Pharmaceuticals Inc. Spiro [benzofuran-2(3H),1'-cycloheptane]s and their therapeutic use
IE70521B1 (en) * 1989-02-28 1996-12-11 Zeneca Pharma Sa Heterocycles with inhibitory activity of 5-lipoxygenase
US6828460B2 (en) 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives
TR200102742T2 (en) * 1999-03-22 2002-05-21 Pfizer Inc. Resorcinol derivatives
JP2009536623A (en) * 2006-04-24 2009-10-15 アラーガン、インコーポレイテッド Abnormal cannabidiol compounds as intraocular pressure-lowering agents
US7618966B2 (en) 2006-04-24 2009-11-17 Allergan, Inc. Abnormal Cannabidiols as agents for lowering intraocular pressure
US7718830B2 (en) 2006-04-24 2010-05-18 Allergan, Inc. Abnormal cannabidiols as agents for lowering intraocular pressure
US7612101B2 (en) 2006-04-24 2009-11-03 Allergan, Inc. Abnormal cannabidiols as agents for lowering intraocular pressure
US12252503B2 (en) 2019-07-12 2025-03-18 Canopy Growth Corporation Cannabinoid derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU487907A1 (en) * 1973-09-21 1975-10-15 Полоцкий Химический Комбинат Им. 50-Летия Белор.Сср Polymer composition

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049953A3 (en) * 1980-09-19 1982-12-08 Pfizer Inc. 4-(substituted phenyl)-naphthalen-2(1h)-ones and 2-ols, processes for their preparation, and pharmaceutical compositions containing them
EP0048572A3 (en) * 1980-09-19 1982-12-08 Pfizer Inc. Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
FR2527203A1 (en) * 1982-05-18 1983-11-25 Mitsui Toatsu Chemicals NOVEL ALKYLAROMATIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, INSECTICIDAL AGENTS AND ACARICIDES CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS
GB2120664A (en) * 1982-05-18 1983-12-07 Mitsui Toatsu Chemicals Aromatic alkene derivatives used as insecticides and acaricides
US4814340A (en) * 1982-05-18 1989-03-21 Mitsui Toatsu Chemicals, Inc. 1,4-diaryl alkane derivatives having insecticidal and acaricidal activity
US4736057A (en) * 1983-11-11 1988-04-05 Imperial Chemical Industries Plc Cyclohexane derivatives
CN109369514A (en) * 2018-12-10 2019-02-22 天津科技大学 A kind of synthetic method of six-membered carbon ring derivative
CN109369514B (en) * 2018-12-10 2021-10-26 天津科技大学 Synthetic method of six-membered carbocyclic ring derivative

Also Published As

Publication number Publication date
ATA658778A (en) 1980-08-15
NO149426C (en) 1984-04-18
FR2402639A1 (en) 1979-04-06
CA1110261A (en) 1981-10-06
NZ188391A (en) 1984-05-31
IE781841L (en) 1979-03-13
MY8500094A (en) 1985-12-31
ES480150A1 (en) 1980-09-01
DE2839836C2 (en) 1983-01-27
JPS5758329B2 (en) 1982-12-09
MX5306E (en) 1983-06-14
IN150334B (en) 1982-09-11
GR74134B (en) 1984-06-06
FI66584B (en) 1984-07-31
FI782794A7 (en) 1979-03-14
HK13284A (en) 1984-02-24
ES480149A0 (en) 1980-11-01
DE2839836A1 (en) 1979-03-15
IT1099054B (en) 1985-09-18
ES8100795A1 (en) 1980-11-01
ES473288A1 (en) 1980-03-01
PH15252A (en) 1982-11-02
CH635812A5 (en) 1983-04-29
AU3981878A (en) 1980-03-20
GB2004870B (en) 1982-01-20
AR224618A1 (en) 1981-12-30
AU513523B2 (en) 1980-12-04
IL55556A (en) 1982-11-30
FI66584C (en) 1984-11-12
IL55556A0 (en) 1978-12-17
LU80220A1 (en) 1980-04-21
NO783087L (en) 1979-03-14
IE47187B1 (en) 1984-01-11
JPS5448741A (en) 1979-04-17
SE7809060L (en) 1979-03-14
KE3352A (en) 1983-12-16
DK400878A (en) 1979-03-14
IT7827558A0 (en) 1978-09-12
NO792840L (en) 1979-03-14
NL7809274A (en) 1979-03-15
NO149426B (en) 1984-01-09
PH16597A (en) 1983-11-22
SE431085B (en) 1984-01-16
AT361455B (en) 1981-03-10
NL8303358A (en) 1984-02-01

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