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DE199636T1 - Benzoenaphthalinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazie und kosmetik. - Google Patents

Benzoenaphthalinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazie und kosmetik.

Info

Publication number
DE199636T1
DE199636T1 DE198686400785T DE86400785T DE199636T1 DE 199636 T1 DE199636 T1 DE 199636T1 DE 198686400785 T DE198686400785 T DE 198686400785T DE 86400785 T DE86400785 T DE 86400785T DE 199636 T1 DE199636 T1 DE 199636T1
Authority
DE
Germany
Prior art keywords
radical
naphthoic acid
adamantyl
methoxyphenyl
carbon atoms
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
DE198686400785T
Other languages
English (en)
Inventor
Jean-Michel F-06650 Nice Bernardon
Jacques F-06130 Grasse Eustache
Braham Chemin De Val-Bosquet F-06600 Antibes Shroot
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.)
Galderma Research and Development SNC
Original Assignee
Centre International de Recherches Dermatologiques Galderma
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 Centre International de Recherches Dermatologiques Galderma filed Critical Centre International de Recherches Dermatologiques Galderma
Publication of DE199636T1 publication Critical patent/DE199636T1/de
Pending legal-status Critical Current

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    • 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
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
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    • A61K8/37—Esters of carboxylic acids
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    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
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    • 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]
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    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
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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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C39/24—Halogenated derivatives
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    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
    • C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
    • C07C63/36—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings containing one carboxyl group
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    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
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    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/17—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
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    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
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    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings
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    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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    • 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
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
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    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (1)

  1. Patentansprüche
    R7 ein Wasserstoffatom, einen Alkylrest mit 1 bis 20 Kohlenstoffatomen, einen Monohydroxyalkylrest oder einen Polyhydroxyalkylrest bedeutet, r1 und r" ein Wasserstoffatom, einen niedrigen Alkylrest, einen Mono- oder Polyhydroxyalkylrest, einen gegebenenfalls substituierten Arylrest oder einen Rest einer Aminosäure oder eines aminierten Zuckers bedeuten oder zusamnen auch einen Heterocyclus bilden,
    R„ ein Wasserstoffatom, einen gegebenenfalls verzweigten Alkylrest mit 1 bis 15 Kohlenstoffatomen, einen
    Alkoxyrest mit 1 bis 4 Kohlenstoffatomen oder einen cycloaliphatischen Rest bedeutet,
    R3 ein Wasserstoffatom, einen Hydroxyrest, einen gegebenenfalls verzweigten Alkylrest mit 1 bis 4
    Kohlenstoffatomen, einen Alkoxyrest mit 1 bis 10
    Kohlenstoffatomen, einen gegebenenfalls substituierten cycloaliphatischen Rest, einen thiocycloaliphatischen ,Q Rest oder einen Rest der Formel -O-Si-(CH.J2~Ro ^e~
    deutet, wobei Rß für einen linearen oder verzweigten niedrigen Alkylrest steht, und
    R> und R5, die gleich oder verschieden sind, ein Wasserstoff atom, einen niedrigen Alkylrest, einen Hydroxyrest oder einen niedrigen Acyloxyrest bedeuten,
    sowie die Salze der Benzonaphthalin-Derivate der
    Formel (I).
    „0 2. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß es sich bei dem Alkylrest um einen Methyl-, Ethyl-, Isopropyl-, Butyl- oder tert.-Butylrest handelt.
    3. Verbindungen nach Anspruch 1, dadurch gekennzeichnet,
    _,. daß der Alkoxyrest ein Rest mit 1 bis 10 Kohlenstoff-Ao
    atomen ist und einen Methoxy-, Ethoxy-, Isopropoxy-,
    Hexyloxy- oder Decyloxyrest darstellt.
    4. Verbindungen nach Anspruch 1, dadurch gekennzeichnet,
    daß der niedrige Acyloxyrest ein Rest mit 1 bis 4
    3U
    Kohlenstoffatomen ist und einen Acetyloxy- oder
    Propionyloxyrest darstellt.
    5. Verbindungen nach Anspruch 1, dadurch gekennzeichnet,
    daß der niedrige Monohydroxyalkylrest ein Rest mit 2 oder 35
    3 Kohlenstoffatomen ist und einen 2-Hydroxyethyl oder 2-Hydroxypropylrest darstellt.
    6. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß der Polyhydroxyalkylrest ein Rest mit 3 bis Kohlenstoffatomen und mit 2 bis 5 Hydroxygruppen ist und einen 2,3-Dihydroxypropylrest, einen 1,3-Dihydroxypropylrest oder einen Pentaeryhtritrest darstellt.
    7. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß der cycloaliphatische Rest ein mono- oder polycyclischer Rest ist und den 1-Methylcyclohexylrest oder 1-Adamantylrest darstellt.
    8. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß der thiocycloaliphatische Rest der 1-Adamantylthiorest ist.
    9. Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß die Reste r' und r" zusammen einen Heterocyclus bilden und für einen Piperidino-, Piperazino-, Morpholidino- oder Pyrrolidinorest stehen.
    1Ü. Verbindungen nach einem der Ansprüche 1 bis 9 der folgenden allgemeinen Formel
    (II)
    &Ggr; T
    worin
    r!. für einen Rest - Nv oder 6 \r„
    einen Rest -OR* steht, wobei
    r1 und r", die gleich oder verschieden sind, ein Wasserstoffatom oder einen niedrigen Alkylrest bedeuten oder zusammen einen Morpholinorest bilden und R'_ ein Wasserstoffatom oder einen niedrigen Alkyl- ^ rest bedeutet,
    R1 ein Wasserstoffatom oder einen Alkylrest, einen Alkoxyrest oder den 1-Adamantylrest bedeutet und
    R' ein Wasserstoffatom, einen Hydroxyrest, einen Alkylrest, einen Alkoxyrest oder den 1-Adamantylthiorest bedeutet.
    11. Verbindungen nach einem der vorhergehenden Ansprüche,
    nämlich:
    15
    6-(3-Methylphenyl)-2-naphthoesäure und deren Methylester,
    6-(4-tert.-Butylphenyl)-2-naphthoesäure und deren Methylester,
    6-(3-tert.-Butylphenyl)-2-naphthoesäure und deren Methyl-20
    ester,
    6-(3,4-Dimethoxyphenyl)-2-naphthoesäure und deren Methylester,
    6-[p-(1-Adamantylthio)phenyl]-2-naphthoesäure und deren Methylester,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoesäure und deren Methylester,
    6-[3-(1-Adamantyl-4-tert.-butyldimethylsilyloxyphenyl]-2-naphthoesäure-methylester,
    6-[3-(1-Adamantyl-4-hydroxyphenyl]-2-naphthoesäure-methylester,
    6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthoesäure,
    gg 6-[3-(1-Adamantyl)-4-brom-i-decyloxyphenyl]-2-naphthoesäure-methy!ester,
    6—13—(1-Adamantyl)-4-decyloxyphenyl]-2-naphthoesäure,
    6-13-(1-Adamantyl)-4-hexyloxyphenyl]-2-naphthoesäuremethylester,
    - 6-[3-(1-Adamantyl)-4-hexyloxyphenyl]-2-naphthoesäure,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-4-acetoxy-i-methyl-2-naphthoesäure-methylester,
    6-[3-(1-Adamanty1)-4-methoxyphenyl]-4-hydroxy-1-methyl-2-naphthoesäure,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-4-hydroxy-1-methyl-2-naphthoesäure-methylester,
    6-[3-(1-Adamantyl)-4-methoxyphenyl)-i-methyl-2-naphthoesäure-methylester,
    1^ 6-[3-(1-Adamantyl)-4-methoxyphenyl]-1-methyl-2-naphthoesäure,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthalinmethanol,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoesäureethylamid,
    6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoesäuremorpholid,
    6-(3-tert.-Butyl-4-methoxyphenyl)-2-naphthoesäure-methyl-
    ester,
    25
    6-(3-tert.-Butyl-4-methoxyphenyl)-2-naphthoesäure,
    6-[3—(1,1-Dimethyldeeyl)-4-methoxyphenyl]-2-naphthoesäure-methylester, und
    6—[3—(1,1-Dimethyldecyl)-4-methoxyphenyl]-2-naphthoe- *
    säure.
    12. Verfahren zur Herstellung der Verbindungen nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, daß man in einem wasserfreien Lösungsmittelmilieu und in Anwesenheit eines Übergangsmetalls oder eines seiner Komplexe als Reaktionskatalysator das Magnesium-, Lithium- oder Zinkderivat einer Verbindung "der
    folgenden Formel (III):
    (III)
    mit einer halogenierten Naphthalinverbindung der folgenden Formel (IV)
    (IV)
    worin
    R1 bis Rj. die in Anspruch 1 angegebenen Bedeutungen besitzen und
    X und Y für Cl, Br, F oder I stehen, umsetzt.
    13. Verfahren nach Anspruch 12, dadurch gekennzeichnet, daß man die Umsetzung bei -20° bis +300C durchführt.
    14. Medikament, dadurch gekennzeichnet, daß es ein Wirkstoff der Formel (I) und/oder ein Salz davon nach einem der Ansprüche 1 bis 11 ist.
    15. Pharmazeutisches Mittel, dadurch gekennzeichnet, daß es in einem für eine enterale, parenterale, topische oder okulare Verabreichung geeigneten Träger mindestens einen Wirkstoff der Formel (I) und/oder ein Salz davon nach einem der Ansprüche 1 bis 11 enthält.
    16. Mittel nach Anspruch 15, dadurch gekennzeichnet, daß es 0,0005 bis etwa 5 Gew.-% des Wirkstoffs enthält.
    17. Mittel nach Anspruch 15, dadurch gekennzeichnet, daß es in einer täglichen Dosis von 2 &mgr;g/kg bis 2 mg/kg Körpergewicht verabreicht wird.
    18. Verwendung des Medikaments nach Anspruch 14 zur Herstellung eines pharmazeutischen Mittels zur Behandlung von dermatologischen, rheumatischen, respiratorischen sowie ophtalmologischen Störungen.
    19. Kosmetisches Mittel zur Haar- und Körperhygiene, dadurch gekennzeichnet, daß es in einem geeigneten kosmetischen Träger mindestens einen Wirkstoff der Formel (I) nach einem der Ansprüche 1 bis 11 enthält.
    20. Kosmetisches Mittel nach Anspruch 19, dadurch gekennzeichnet, daß es den Wirkstoff der Formel (I) in einer Konzentration von 0,0005 bis 2 % und vorzugsweise von 0,01 bis 1 Gew.-% enthält.
DE198686400785T 1985-04-11 1986-04-11 Benzoenaphthalinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazie und kosmetik. Pending DE199636T1 (de)

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FR2555571B1 (fr) * 1983-11-28 1986-11-28 Interna Rech Dermatolo Centre Derives du naphtalene, leur procede de preparation et leur application dans le domaine therapeutique
LU85849A1 (fr) * 1985-04-11 1986-11-05 Cird Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques
JPH01254659A (ja) * 1988-04-05 1989-10-11 Ss Pharmaceut Co Ltd ピロール誘導体

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EP0199636B1 (de) 1989-02-08
PT82361A (fr) 1986-05-01
NO170627C (no) 1992-11-11
FI88793B (fi) 1993-03-31
JPS61251632A (ja) 1986-11-08
CA1266646A (fr) 1990-03-13
FI914266A0 (fi) 1991-09-10
IL78463A0 (en) 1986-08-31
DE3662038D1 (en) 1989-03-16
DK172070B1 (da) 1997-10-13
AU5591286A (en) 1986-10-16
NO861413L (no) 1986-10-13
GR860948B (en) 1986-08-06
AU595192B2 (en) 1990-03-29
AU4796190A (en) 1990-05-10
USRE34805E (en) 1994-12-06
ZA862733B (en) 1986-12-30
USRE34440E (en) 1993-11-09
EP0199636A1 (de) 1986-10-29
DE10199023I2 (de) 2003-01-09
LU85849A1 (fr) 1986-11-05
ES8705845A1 (es) 1987-06-01
FI861510A0 (fi) 1986-04-09
FI88793C (fi) 1993-07-12
PT82361B (pt) 1988-03-03
FI87762B (fi) 1992-11-13
IE860931L (en) 1986-10-11
NO170627B (no) 1992-08-03
ATE40675T1 (de) 1989-02-15
US4717720A (en) 1988-01-05
DK162286A (da) 1986-10-12
NL300209I1 (nl) 2006-02-01
AU638223B2 (en) 1993-06-24
US5212303A (en) 1993-05-18
DE10199023I1 (de) 2001-06-21
DK162286D0 (da) 1986-04-10
US4940696A (en) 1990-07-10
FI87762C (fi) 1993-02-25
JPH0830015B2 (ja) 1996-03-27
ES554186A0 (es) 1987-06-01
IL78463A (en) 1990-04-29
US5183889A (en) 1993-02-02
IE58882B1 (en) 1993-12-01
US5098895A (en) 1992-03-24
NZ215779A (en) 1989-05-29
FI861510A7 (fi) 1986-10-12
NL300209I2 (nl) 2006-03-01

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