HU191337B - Process for producing new 4-/2-hydroxy-4-substituted-phenyl/-naphtalene-2/1h/-one and -ol derivatives and pharmaceutical compositions containing them - Google Patents

Process for producing new 4-/2-hydroxy-4-substituted-phenyl/-naphtalene-2/1h/-one and -ol derivatives and pharmaceutical compositions containing them Download PDF

Info

Publication number
HU191337B
HU191337B HU812710A HU271081A HU191337B HU 191337 B HU191337 B HU 191337B HU 812710 A HU812710 A HU 812710A HU 271081 A HU271081 A HU 271081A HU 191337 B HU191337 B HU 191337B
Authority
HU
Hungary
Prior art keywords
alpha
hydrogen
formula
beta
compound
Prior art date
Application number
HU812710A
Other languages
English (en)
Hungarian (hu)
Inventor
Michael R Johnson
Lawrence Sh Melvin
Original Assignee
Pfizer Inc.,Us
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 Inc.,Us filed Critical Pfizer Inc.,Us
Publication of HU191337B publication Critical patent/HU191337B/hu

Links

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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • 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
    • 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
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • 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
    • C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C62/30—Unsaturated compounds
    • C07C62/38—Unsaturated compounds containing keto groups
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • 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
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pain & Pain Management (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
HU812710A 1980-09-19 1981-09-18 Process for producing new 4-/2-hydroxy-4-substituted-phenyl/-naphtalene-2/1h/-one and -ol derivatives and pharmaceutical compositions containing them HU191337B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/189,402 US4285867A (en) 1980-09-19 1980-09-19 Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor

Publications (1)

Publication Number Publication Date
HU191337B true HU191337B (en) 1987-02-27

Family

ID=22697189

Family Applications (1)

Application Number Title Priority Date Filing Date
HU812710A HU191337B (en) 1980-09-19 1981-09-18 Process for producing new 4-/2-hydroxy-4-substituted-phenyl/-naphtalene-2/1h/-one and -ol derivatives and pharmaceutical compositions containing them

Country Status (27)

Country Link
US (1) US4285867A (en:Method)
EP (1) EP0049953B1 (en:Method)
JP (1) JPS57112344A (en:Method)
KR (1) KR850001337B1 (en:Method)
AR (1) AR228617A1 (en:Method)
AT (1) ATE7487T1 (en:Method)
AU (1) AU526673B2 (en:Method)
CA (2) CA1166639A (en:Method)
CS (4) CS221989B2 (en:Method)
DD (2) DD206986A5 (en:Method)
DE (1) DE3163651D1 (en:Method)
DK (1) DK415281A (en:Method)
ES (2) ES505625A0 (en:Method)
FI (1) FI75143C (en:Method)
GR (1) GR75346B (en:Method)
HU (1) HU191337B (en:Method)
IE (1) IE51630B1 (en:Method)
IL (1) IL63869A (en:Method)
IN (1) IN157167B (en:Method)
NO (2) NO813186L (en:Method)
NZ (2) NZ206872A (en:Method)
PH (1) PH17616A (en:Method)
PL (5) PL133727B1 (en:Method)
PT (1) PT73700B (en:Method)
SU (2) SU1217248A3 (en:Method)
YU (2) YU225981A (en:Method)
ZA (1) ZA816489B (en:Method)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4593131A (en) * 1980-09-19 1986-06-03 Pfizer Inc. Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4360700A (en) * 1981-11-02 1982-11-23 Pfizer Inc. Intermediates for making 1-(3-benzyloxyphenyl)-1,1-dimethylheptane
JP4639414B2 (ja) * 1998-12-25 2011-02-23 Dic株式会社 デカヒドロナフタレン誘導体及びその製造方法
CN107915633A (zh) * 2017-12-06 2018-04-17 安徽绩溪县徽煌化工有限公司 一种间苄氧基苯甲酸甲酯的制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB464328A (en) * 1935-10-09 1937-04-09 Henkel & Cie Gmbh Improvements in or relating to the manufacture of hydroarylated aromatic hydroxy compounds and derivatives thereof
US2993056A (en) * 1956-08-31 1961-07-18 Istituto Sieroterapico Italian Production of the 1-6-lactone of 6-hydroxy-8-acetoxy-octanoic acid
US2886589A (en) * 1957-08-05 1959-05-12 Merck & Co Inc 8-methyl-5-oxyphenyl hexahydroindan compounds
US3862986A (en) * 1966-07-01 1975-01-28 Hoffmann La Roche 1-Hydroxymethyl-amino-2-alkyl-or allyl-2-(3{40 -methoxy-phenyl)-chclohexanes
US3378589A (en) * 1967-05-01 1968-04-16 American Cyanamid Co Process of preparing the ring b carbon analog of griseofulvin
US3576887A (en) * 1967-05-01 1971-04-27 American Home Prod Process for the preparation of oxaphenanthrenes and intermediates therefor
US3974157A (en) * 1974-03-04 1976-08-10 Pennwalt Corporation 1-(Amino-alkyl)-2-aryl-cyclohexane alcohols and esters
US4283569A (en) * 1977-09-13 1981-08-11 Pfizer Inc. Hydroxyalkyl and oxoalkyl substituted phenols as analgesics and sedatives
PT68543A (en) 1977-09-13 1978-10-01 Pfizer Process for the preparation of 3-2-hydroxi-4-substituted -phenyl cycloalkanone and cycloalkanol analgesic agents andintermediates therefor
SE431085B (sv) * 1977-09-13 1984-01-16 Pfizer 3-(2-hydroxi-4-(substituerade)fenyl)cykloalkanoner och -cykloalkanoder och vissa derivat derav till anvendning for farmakologiska och medicinska endamal
US4188495A (en) * 1977-11-14 1980-02-12 Pfizer Inc. 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor

Also Published As

Publication number Publication date
PL135169B1 (en) 1985-10-31
AU526673B2 (en) 1983-01-27
ES8301872A1 (es) 1982-12-16
YU149283A (en) 1983-12-31
KR830007592A (ko) 1983-11-04
DK415281A (da) 1982-03-20
GR75346B (en:Method) 1984-07-13
PL237443A1 (en) 1983-02-14
AU7547481A (en) 1982-06-10
JPS57112344A (en) 1982-07-13
NZ206872A (en) 1984-12-14
SU1217249A3 (ru) 1986-03-07
PT73700B (en) 1983-10-19
CA1166639A (en) 1984-05-01
DD209434A5 (de) 1984-05-09
CA1171416A (en) 1984-07-24
ES505625A0 (es) 1982-12-16
IL63869A (en) 1985-03-31
PH17616A (en) 1984-10-05
PL233104A1 (en:Method) 1982-11-08
CS221991B2 (en) 1983-04-29
DD206986A5 (de) 1984-02-15
CS221989B2 (en) 1983-04-29
YU225981A (en) 1984-02-29
JPS6158456B2 (en:Method) 1986-12-11
EP0049953A2 (en) 1982-04-21
KR850001337B1 (ko) 1985-09-19
IN157167B (en:Method) 1986-02-01
ES514376A0 (es) 1983-05-01
FI75143C (fi) 1988-05-09
CS221988B2 (en) 1983-04-29
IE51630B1 (en) 1987-01-21
SU1217248A3 (ru) 1986-03-07
EP0049953A3 (en) 1982-12-08
ZA816489B (en) 1982-09-29
ATE7487T1 (de) 1984-06-15
FI812927L (fi) 1982-03-20
US4285867A (en) 1981-08-25
PL237442A1 (en) 1983-02-14
CS221990B2 (en) 1983-04-29
IE812185L (en) 1982-03-19
NZ198390A (en) 1984-12-14
PL133727B1 (en) 1985-06-29
NO823160L (no) 1982-03-22
PL134880B1 (en) 1985-09-30
ES8306087A1 (es) 1983-05-01
PL138052B1 (en) 1986-08-30
PL237441A1 (en) 1983-02-14
AR228617A1 (es) 1983-03-30
EP0049953B1 (en) 1984-05-16
DE3163651D1 (en) 1984-06-20
IL63869A0 (en) 1981-12-31
PL131787B1 (en) 1985-01-31
FI75143B (fi) 1988-01-29
NO813186L (no) 1982-03-22
PT73700A (en) 1981-10-01

Similar Documents

Publication Publication Date Title
US4912113A (en) 3,7-diazabicyclo(3,3,1)nonane compounds and pharmaceutical compositions containing such compounds
US4206225A (en) 2,10-Disubstituted dibenzo[b,d]pyrans and benzo[c]quinolines
US4371720A (en) 2-Hydroxy-4-(substituted) phenyl cycloalkanes and derivatives
US4143139A (en) 9-Hydroxydibenzo[b,d]pyrans and intermediates
Schuda et al. Total synthesis of hirsutic acid C and complicatic acid
US4870084A (en) Bicyclic benzo fused pyran compounds used for nausea treatment and prevention
EP0089781B1 (en) Bicyclic benzo fused compounds
US4243674A (en) 9-Hydroxydibenzo[b,d]pyrans and intermediates therefore
US3567737A (en) Derivatives of (2-cycloalkyl-1-phenyl-3,4-dihydronaphthalenes and) 2 - cycloalkyl - 1 - phenyl - 1,2,3,4 - tetrahydro-naphthalenes
EP0049953B1 (en) 4-(substituted phenyl)-naphthalen-2(1h)-ones and 2-ols, processes for their preparation, and pharmaceutical compositions containing them
US4405626A (en) 9-Hydroxyoctahydrobenzo(c)quinolines analgesic compositions containing them and processes for producing analgesic with them
US4933475A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4486609A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4835192A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4927819A (en) Cyclo-octane neuroprotective agents
US4593131A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4739079A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
US4331602A (en) Pharmacologically active 4-[2-hydroxy-4-(substituted]phenyl)naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
Nussbaumer et al. A Stereoselective Synthesis of (±)‐cis‐γ‐Irone
DE3873786T2 (de) Substituierte 1,3,4,9-tetrahydropyrano(3,4-b)indol-1-essigsaeuren.
US4831059A (en) Producing analgesia with pharmacologically active 2-hydroxy-4-(substituted) phenyl cycloalkanes derivatives
EP0027948A1 (en) Tetrahydro-fluorene compounds, processes for their preparation and pharmaceutical compositions thereof
EP0048572A2 (en) Substituted 2-hydroxyphenyl cycloalkanes and pharmaceutical compositions thereof
US4921994A (en) Pharmacologically active 2-hydroxy-4-(substituted) phenyl cycloalkanes and derivatives thereof
US4544745A (en) Cis-4a-aryl, 1, 2, 3, 4, 4A, 9B-hexahydro-benzofuro-[3,2-C]- pyridines useful as analgesics

Legal Events

Date Code Title Description
HU90 Patent valid on 900628
HMM4 Cancellation of final prot. due to non-payment of fee