FR2422677A1 - Tetra:hydro-naphthyl- and indanyl-vinyl-benzene derivs. - useful as anti:neoplastic agents and for dermatological and rheumatic conditions - Google Patents

Tetra:hydro-naphthyl- and indanyl-vinyl-benzene derivs. - useful as anti:neoplastic agents and for dermatological and rheumatic conditions

Info

Publication number
FR2422677A1
FR2422677A1 FR7911870A FR7911870A FR2422677A1 FR 2422677 A1 FR2422677 A1 FR 2422677A1 FR 7911870 A FR7911870 A FR 7911870A FR 7911870 A FR7911870 A FR 7911870A FR 2422677 A1 FR2422677 A1 FR 2422677A1
Authority
FR
France
Prior art keywords
alkyl
useful
treating
indanyl
dermatological
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.)
Pending
Application number
FR7911870A
Other languages
French (fr)
Inventor
Peter Loeliger
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of FR2422677A1 publication Critical patent/FR2422677A1/en
Pending legal-status Critical Current

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/47—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
    • C07C13/48—Completely or partially hydrogenated naphthalenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
    • C07C43/16—Vinyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/164—Unsaturated ethers containing six-membered aromatic rings
    • C07C43/168—Unsaturated ethers containing six-membered aromatic rings containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/548—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/798—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • 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
    • C07D317/10—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 not condensed with other rings
    • C07D317/12—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 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • 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
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5456—Arylalkanephosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms

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  • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Tetrahydronaphthyl- and indanyl-vinylbenzene derivs. of formula (I) are new: (where n is 1 or 2; R1 and R2 are H, 1-6C alkyoxy or halogen, except that when n is 2, R2 is H; R3-6 are H or 1-6C alkyl; R7 is H, Me or Et; R8 and R9 are H, 1-6C alkyl or halogen; R10 is (CH=CR19)mR11; m is 0 or 1; R11 is CHR12R13, COR15 or 2-oxazolinyl or, when m is 1, also H; R12 is H or 1-6C alkyl; R13 is H, 1-6C alkyl, NR17R18 or OR14; R14 is H, 1-6C alkyl or alkanoyl; R15 is H, 1-6C alkyl, Or16 or (CH2)pNR17R18; R16 is H, 1-6C alkyl, 1-6C hydroxyalkyl, or aryl or aralkyl both opt. ring substd.; R17 and R18 are H or 1-6C alkyl; or NR17R18 is a heterocyclic gp.; R19 is H or 1-6C alkyl; and p is 0-3. When R11 is COR 15 and R15 is H or 1-6C alkyl, the gp. may be betalised). (I) are antineoplastic agents and are useful for treating premalignant lesions; also useful for treating acne, psoriasis and other dermatoses accompanied by cornification and for treating inflammatory and allergic dermatologic conditions. Also (I) are useful for treating mucous membrane diseases associated with inflammatory, degerative or metaplastic changes. (I) are orally effective for treating rheumatic conditions, esp. arthritis, Bechtereiv's spondylarthritis ankylpoetica and psoriatic arthropathy, at a dose of 0.01-1 mg/kg. (I) have much higher potencies than known retinoids; over-dosage can cause vitamin A hypervitaminosis.
FR7911870A 1977-12-22 1979-05-10 Tetra:hydro-naphthyl- and indanyl-vinyl-benzene derivs. - useful as anti:neoplastic agents and for dermatological and rheumatic conditions Pending FR2422677A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU78751 1977-12-22

Publications (1)

Publication Number Publication Date
FR2422677A1 true FR2422677A1 (en) 1979-11-09

Family

ID=19728806

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7911870A Pending FR2422677A1 (en) 1977-12-22 1979-05-10 Tetra:hydro-naphthyl- and indanyl-vinyl-benzene derivs. - useful as anti:neoplastic agents and for dermatological and rheumatic conditions

Country Status (3)

Country Link
FR (1) FR2422677A1 (en)
YU (2) YU41326B (en)
ZA (1) ZA787029B (en)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1109699A (en) * 1953-10-09 1956-01-31 P F W Of America Polyalkylindanes and products derived therefrom as well as process for the manufacture of said
FR1141714A (en) * 1955-02-23 1957-09-06 Givaudan & Cie Sa Novel musky-smelling substance, and method of preparation thereof
FR1147498A (en) * 1955-02-23 1957-11-26 Givaudan & Cie Sa New musky-smelling substance and its preparation process
FR1148500A (en) * 1955-01-28 1957-12-10 Givaudan & Cie Sa New chemical compounds with musky odor and processes for their preparation
FR1148499A (en) * 1955-01-28 1957-12-10 Givaudan & Cie Sa New musky-smelling substance and its preparation process
FR1148970A (en) * 1955-04-02 1957-12-18 Polak & Schwarz S Essencefabri Process for the preparation of novel substances having an odor and flavor of musky character
FR1152062A (en) * 1953-12-14 1958-02-11 Givaudan & Cie Sa Process for the preparation of acetylated tetrahydronaphthalenes having musky odors, and new products obtained by this process
US3509215A (en) * 1967-06-15 1970-04-28 Givaudan Corp Acyl indan compounds
FR2232529A1 (en) * 1973-06-08 1975-01-03 Mitsui Petrochemical Ind
GB1428467A (en) * 1973-06-07 1976-03-17 Wyeth John & Brother Ltd Indane and tetrahydronaphthalene derivatives

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1109699A (en) * 1953-10-09 1956-01-31 P F W Of America Polyalkylindanes and products derived therefrom as well as process for the manufacture of said
FR1152062A (en) * 1953-12-14 1958-02-11 Givaudan & Cie Sa Process for the preparation of acetylated tetrahydronaphthalenes having musky odors, and new products obtained by this process
FR1148500A (en) * 1955-01-28 1957-12-10 Givaudan & Cie Sa New chemical compounds with musky odor and processes for their preparation
FR1148499A (en) * 1955-01-28 1957-12-10 Givaudan & Cie Sa New musky-smelling substance and its preparation process
FR1141714A (en) * 1955-02-23 1957-09-06 Givaudan & Cie Sa Novel musky-smelling substance, and method of preparation thereof
FR1147498A (en) * 1955-02-23 1957-11-26 Givaudan & Cie Sa New musky-smelling substance and its preparation process
FR1148970A (en) * 1955-04-02 1957-12-18 Polak & Schwarz S Essencefabri Process for the preparation of novel substances having an odor and flavor of musky character
US3509215A (en) * 1967-06-15 1970-04-28 Givaudan Corp Acyl indan compounds
GB1428467A (en) * 1973-06-07 1976-03-17 Wyeth John & Brother Ltd Indane and tetrahydronaphthalene derivatives
FR2232529A1 (en) * 1973-06-08 1975-01-03 Mitsui Petrochemical Ind

Also Published As

Publication number Publication date
YU45730B (en) 1992-07-20
ZA787029B (en) 1979-11-28
YU112685A (en) 1987-12-31
YU297378A (en) 1983-02-28
YU41326B (en) 1987-02-28

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