CA2238274A1 - Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity - Google Patents
Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activityInfo
- Publication number
- CA2238274A1 CA2238274A1 CA002238274A CA2238274A CA2238274A1 CA 2238274 A1 CA2238274 A1 CA 2238274A1 CA 002238274 A CA002238274 A CA 002238274A CA 2238274 A CA2238274 A CA 2238274A CA 2238274 A1 CA2238274 A1 CA 2238274A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- carbons
- phenyl
- retinoid
- biological activity
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/88—Carboxylic acid amides having nitrogen atoms of carboxamide groups bound to an acyclic carbon atom and to a carbon atom of a six-membered aromatic ring wherein at least one ortho-hydrogen atom has been replaced
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
Abstract
Compounds of formula (I) where X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons, or X is [C(R1)2]n where n is an integer between 0 and 2; 1; Y is a phenyl or naphthyl group, or heteroaryl group; W is a substituent selected from the group consisting of F, Br, Cl, I, C1-6alkyl, fluoro substituted C1-5 alkyl, NO2, N3, OH, OCH2OCH3, OC1-10alkyl, tetrazol, CN, SO2C1-6-alkyl, SO2C1-6-fluoro substituted alkyl, SO-C1-6 alkyl, CO-C1-6alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl; L is -(C-Z)-NH- or -HN-(C=Z)-; Z is O or S; A is (CH2)q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds, and B
is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, where R1 -R13 and o, p, m, n, r are as defined in claim 1, have retinoid-like biological activity.
is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, where R1 -R13 and o, p, m, n, r are as defined in claim 1, have retinoid-like biological activity.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/562,000 US5675024A (en) | 1995-11-22 | 1995-11-22 | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity |
US08/562,000 | 1995-11-22 | ||
PCT/US1996/018580 WO1997019052A1 (en) | 1995-11-22 | 1996-11-18 | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2238274A1 true CA2238274A1 (en) | 1997-05-29 |
CA2238274C CA2238274C (en) | 2007-07-24 |
Family
ID=24244382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002238274A Expired - Fee Related CA2238274C (en) | 1995-11-22 | 1996-11-18 | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity |
Country Status (20)
Country | Link |
---|---|
US (5) | US5675024A (en) |
EP (1) | EP0876330B1 (en) |
JP (1) | JP4112003B2 (en) |
KR (1) | KR100450498B1 (en) |
CN (1) | CN1117070C (en) |
AT (1) | ATE200074T1 (en) |
AU (1) | AU702499B2 (en) |
BR (1) | BR9611758A (en) |
CA (1) | CA2238274C (en) |
DE (1) | DE69612303T2 (en) |
DK (1) | DK0876330T3 (en) |
ES (1) | ES2157470T3 (en) |
GR (1) | GR3035979T3 (en) |
IL (1) | IL124597A (en) |
MX (1) | MX9804087A (en) |
NZ (1) | NZ323581A (en) |
PL (1) | PL186404B1 (en) |
PT (1) | PT876330E (en) |
RU (1) | RU2163906C2 (en) |
WO (1) | WO1997019052A1 (en) |
Cited By (2)
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WO2018107289A1 (en) * | 2016-12-14 | 2018-06-21 | Queen's University At Kingston | Compounds and methods for inhibiting cyp26 enzymes |
WO2019113693A1 (en) * | 2017-12-12 | 2019-06-20 | Queen's University At Kingston | Compounds and methods for inhibiting cyp26 enzymes |
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US20030219832A1 (en) * | 1996-03-11 | 2003-11-27 | Klein Elliott S. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
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-
1995
- 1995-11-22 US US08/562,000 patent/US5675024A/en not_active Expired - Lifetime
-
1996
- 1996-11-18 PT PT96941408T patent/PT876330E/en unknown
- 1996-11-18 JP JP51985297A patent/JP4112003B2/en not_active Expired - Lifetime
- 1996-11-18 NZ NZ323581A patent/NZ323581A/en unknown
- 1996-11-18 WO PCT/US1996/018580 patent/WO1997019052A1/en active IP Right Grant
- 1996-11-18 CA CA002238274A patent/CA2238274C/en not_active Expired - Fee Related
- 1996-11-18 PL PL96327457A patent/PL186404B1/en not_active IP Right Cessation
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- 1996-11-18 EP EP96941408A patent/EP0876330B1/en not_active Expired - Lifetime
- 1996-11-18 BR BR9611758A patent/BR9611758A/en not_active Application Discontinuation
- 1996-11-18 DE DE69612303T patent/DE69612303T2/en not_active Expired - Lifetime
- 1996-11-18 AT AT96941408T patent/ATE200074T1/en not_active IP Right Cessation
- 1996-11-18 DK DK96941408T patent/DK0876330T3/en active
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- 1996-11-18 AU AU10560/97A patent/AU702499B2/en not_active Ceased
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- 1996-11-19 KR KR10-1998-0703817A patent/KR100450498B1/en active IP Right Review Request
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1997
- 1997-09-04 US US08/923,864 patent/US5856490A/en not_active Expired - Fee Related
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1998
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- 1998-10-15 US US09/173,574 patent/US6034244A/en not_active Expired - Fee Related
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2000
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- 2000-08-04 US US09/634,733 patent/US6342602B1/en not_active Expired - Fee Related
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Cited By (5)
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WO2018107289A1 (en) * | 2016-12-14 | 2018-06-21 | Queen's University At Kingston | Compounds and methods for inhibiting cyp26 enzymes |
US10874634B2 (en) | 2016-12-14 | 2020-12-29 | Queen's University At Kingston | Compounds and methods for inhibiting CYP26 enzymes |
US11364220B2 (en) | 2016-12-14 | 2022-06-21 | Queen's University At Kingston | Compounds and methods for inhibiting CPY26 enzymes |
WO2019113693A1 (en) * | 2017-12-12 | 2019-06-20 | Queen's University At Kingston | Compounds and methods for inhibiting cyp26 enzymes |
US11795148B2 (en) | 2017-12-12 | 2023-10-24 | Queen's University At Kingston | Compounds and methods for inhibiting CYP26 enzymes |
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EP0876330B1 (en) | 2001-03-28 |
PT876330E (en) | 2001-09-28 |
CN1117070C (en) | 2003-08-06 |
ATE200074T1 (en) | 2001-04-15 |
JP2000500499A (en) | 2000-01-18 |
EP0876330A1 (en) | 1998-11-11 |
DE69612303D1 (en) | 2001-05-03 |
PL186404B1 (en) | 2004-01-30 |
DE69612303T2 (en) | 2001-09-20 |
KR100450498B1 (en) | 2004-11-20 |
IL124597A0 (en) | 1998-12-06 |
BR9611758A (en) | 1999-03-30 |
RU2163906C2 (en) | 2001-03-10 |
MX9804087A (en) | 1998-09-30 |
KR19990071543A (en) | 1999-09-27 |
GR3035979T3 (en) | 2001-08-31 |
CN1214675A (en) | 1999-04-21 |
CA2238274C (en) | 2007-07-24 |
US6034244A (en) | 2000-03-07 |
DK0876330T3 (en) | 2001-08-06 |
US5856490A (en) | 1999-01-05 |
NZ323581A (en) | 1999-07-29 |
IL124597A (en) | 2001-08-08 |
AU1056097A (en) | 1997-06-11 |
JP4112003B2 (en) | 2008-07-02 |
US6124455A (en) | 2000-09-26 |
ES2157470T3 (en) | 2001-08-16 |
US5675024A (en) | 1997-10-07 |
WO1997019052A1 (en) | 1997-05-29 |
US6342602B1 (en) | 2002-01-29 |
AU702499B2 (en) | 1999-02-25 |
PL327457A1 (en) | 1998-12-07 |
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