JP2000500498A - レチノイド様生物学的活性を有する置換アリールまたはヘテロアリールアミド - Google Patents
レチノイド様生物学的活性を有する置換アリールまたはヘテロアリールアミドInfo
- Publication number
- JP2000500498A JP2000500498A JP9519840A JP51984097A JP2000500498A JP 2000500498 A JP2000500498 A JP 2000500498A JP 9519840 A JP9519840 A JP 9519840A JP 51984097 A JP51984097 A JP 51984097A JP 2000500498 A JP2000500498 A JP 2000500498A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- phenyl
- compound
- group
- 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
- -1 heteroaryl amides Chemical class 0.000 title claims description 26
- 230000004071 biological effect Effects 0.000 title abstract description 9
- 125000003107 substituted aryl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 38
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
- 239000005711 Benzoic acid Substances 0.000 claims description 16
- 235000010233 benzoic acid Nutrition 0.000 claims description 16
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 210000004027 cell Anatomy 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- 238000011282 treatment Methods 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 150000001408 amides Chemical class 0.000 description 20
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
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- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- NNMJPCUZFNRTEG-UHFFFAOYSA-N ethyl 4-amino-2-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1F NNMJPCUZFNRTEG-UHFFFAOYSA-N 0.000 description 7
- 230000002265 prevention Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229940104230 thymidine Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- BWHIWEBPMRLTOT-UHFFFAOYSA-N 2,6-ditert-butylpyridine-4-carboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=N1 BWHIWEBPMRLTOT-UHFFFAOYSA-N 0.000 description 4
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 4
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- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
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- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 4
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Classifications
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- 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
-
- 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
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.下記式で示される化合物: [式中、XはCHまたはNであり; R1はそれぞれ、Hまたは炭素数1〜6のアルキルであり; mは0〜5の整数であり; pは0〜2の整数であり; rは0〜2の整数であり; Lは−(C=Z)−NH−、または−NH−(C=Z)−であり(ここで、ZはO またはS); Yはフェニルもしくはナフチル基であるか、またはピリジル、チエニル、フリ ル、ピリダジニル、ピリミジニル、ピラジニル、チアゾリル、オキサゾリル、イ ミダゾリルおよびピラゾリルから成る群から選択するヘテロアリールであり、該 フェニル、ナフチルおよびヘテロアリール基は場合により、1個または2個のR1 置換基を有し; WはF、Br、Cl、I、C1-6アルキル、フルオロ置換C1-6アルキル、NO2 、N3、OH、OCH2OCH3、OC1-10アルキル、テトラゾール、CN、SO2 C1-6アルキル、SO2C1-6アルキル、SO2C1-6−フルオロ置換アルキル、S O−C1-6アルキル、CO−C1-6アルキル、COOR8、フェニル、フェニルも しくは置換フェニル以外の基Wで置換されたフェニル自体から成る群から選択す る置換基であり、XがCHでrが0である場合は、pは0でなく、少なくとも1 個の基Wはアルキルでなく; Aは、(CH2)q(ここで、qは0〜5)、炭素数3〜6の低級分枝鎖アルキル、 炭素数3〜6のシクロアルキル、炭素数2〜6/二重結合数1または2のアルケ ニル、炭素数2〜6/三重結合数1または2のアルキニルであり; BはCOOHもしくは薬学的に許容し得るその塩、COOR8、CONR9R10 、−CH2OH、CH2OR11、CH2OCOR11、CHO、CH(OR12)2、CH OR13O、−COR7、CR7(OR12)2、CR7OR13Oである(ここで、R7は 炭素数1〜5のアルキル、シクロアルキルまたはアルケニル基であり、R8は炭 素数1〜10のアルキル、トリメチルシリルアルキル(アルキル基の炭素数1〜 10)、炭素数5〜10のシクロアルキル、フェニルまたは低級アルキルフェニ ルであり、R9およびR10はそれぞれ水素、炭素数1〜10のアルキル、炭素数 5〜10のシクロアルキル、フェニルまたは低級アルキルフェニルであり、R11 は低級アルキル、フェニルまたは低級アルキルフェニルであり、R12は低級アル キルであり、R13は炭素数2〜5の2価アルキル基である)。]。 2.Lが−(C=Z)−NH−である請求項1記載の化合物。 3.Lが−NH−(C=Z)−である請求項1記載の化合物。 4.XがCHである請求項1記載の化合物。 5.XがNである請求項1記載の化合物。 6.Yは、フェニル、ピリジル、2−チアゾリル、チエニルおよびフリルから 成る群から選択する請求項1記載の化合物。 7.Yがフェニルである請求項6記載の化合物。 8.Wが分枝鎖アルキル、F、NO2、Br、I、CF3、N3、またはOHで ある請求項1記載の化合物。 9.(W)pが2個の分枝鎖アルキル基である請求項8記載の化合物。 10.(W)rが1個もしくは2個のフルオロ、または1個もしくは2個のNO2 基である請求項8記載の化合物。 11.下記式で示される化合物:[式中、XはCHまたはNであり; R1はそれぞれ、Hまたは炭素数1〜6のアルキルであり; mは0〜5の整数であり; pは0〜2の整数であり; rは0〜2の整数であり; ZはOまたはSであり; WはF、Br、Cl、I、C1-6アルキル、フルオロ置換C1-6アルキル、NO2 、N3、OH、OCH2OCH3、OC1-10アルキル、テトラゾール、CN、SO2 C1-6アルキル、SO2C1-6アルキル、SO2C1-6−フルオロ置換アルキル、S O−C1-6アルキル、CO−C1-6アルキル、COOR8、フェニル、フェニルも しくは置換フェニル以外の基Wで置換されたフェニル自体から成る群から選択す る置換基であり、XがCHでrが0である場合は、pは0でなく、少なくとも1 個の基Wはアルキルでなく; Aは、(CH2)q(ここで、qは0〜5)、炭素数3〜6の低級分枝鎖アルキル、 炭素数3〜6のシクロアルキル、炭素数2〜6/二重結合数1または2のアルケ ニル、炭素数2〜6/三重結合数1または2のアルキニルであり; BはCOOHもしくは薬学的に許容し得るその塩、COOR8、CONR9R10 、−CH2OH、CH2OR11、CH2OCOR11、CHO、CH(OR12)2、CH OR13O、−COR7、CR7(OR12)2、CR7OR13Oである(ここで、R7は 炭素数1〜5のアルキル、シクロアルキルまたはアルケニル基であり、R8は炭 素数1〜10のアルキル、トリメチルシリルアルキル(アルキル基の炭素数1〜 10)、炭素数5〜10のシクロアルキル、フェニルまたは低級アルキルフェニ ル であり、R9およびR10はそれぞれ水素、炭素数1〜10のアルキル、炭素数5 〜10のシクロアルキル、フェニルまたは低級アルキルフェニルであり、R11は 低級アルキル、フェニルまたは低級アルキルフェニルであり、R12は低級アルキ ルであり、R13は炭素数2〜5の2価アルキル基である)。]。 12.XがCHである請求項11記載の化合物。 13.ZがOである請求項12記載の化合物。 14.Aが(CH2)qであり、BがCOOHもしくは薬学的に許容し得るその塩 、COOR8、またはCONR9R10である請求項13記載の化合物。 15.(W)pが2個の分枝鎖アルキル基であり、(W)rが1個もしくは2個のフ ルオロ、または1個もしくは2個のNO2基である請求項14記載の化合物。 16.フェニル環が基(C=Z)NH−と−A−B−とで1,4置換されている 請求項15記載の化合物。 17.下記式で示される化合物: [式中、XはCHまたはNであり; W1はHまたはOHであり; W2はH、FまたはNO2であり; W3はH、FまたはNO2であり; R**8はH、CH3またはC2H5であり; XがCHである場合はW1、W2およびW3のすべてがHであることはない。] 。 18.XがNである請求項17記載の化合物。 19.W2がFであり、W3がHである請求項18記載の化合物。 20.エチル2−フルオロ−4−[(2',6'−ジ−t−ブチルピリダ−4'−イ ル)カルバモイル]ベンゾエート;または 2−フルオロ−4−[(2',6'−ジ−t−ブチルピリダ−4'−イル)カルバモ イル]安息香酸 である請求項19記載の化合物。 21.W2がFであり、W3がFである請求項18記載の化合物。 22.メチル2,6−ジフルオロ−4−[(2',6'−ジ−t−ブチルピリダ−4 '−イル)カルバモイル]ベンゾエート;または 2,6−ジフルオロ−4−[(2',6'−ジ−t−ブチルピリダ−4'−イル)カル バモイル]安息香酸 である請求項21記載の化合物。 23.W2がNO2である請求項18記載の化合物。 24.メチル2−ニトロ−4−[(2',6'−ジ−t−ブチルピリダ−4'−イル )カルバモイル]ベンゾエート;または 2−ニトロ−4−[(2',6'−ジ−t−ブチルピリダ−4'−イル)カルバモイ ル]安息香酸 である請求項23記載の化合物。 25.W1、W2およびW3がいずれも水素である請求項18記載の化合物。 26.エチル4−[(2',6'−ジ−t−ブチルピリダ−4'−イル)カルバモイ ル]ベンゾエート;または 4−[(2',6'−ジ−t−ブチルピリダ−4'−イル)カルバモイル]安息香酸で ある請求項25記載の化合物。 27.XがCHである請求項17記載の化合物。 28.W2がFであり、W3がHである請求項27記載の化合物。 29.エチル2−フルオロ−4−[(3',5'−ジ−t−ブチルフェニル)カルバ モイル]ベンゾエート;または 2−フルオロ−4−[(3',5'−ジ−t−ブチルフェニル)カルバモイル]安息 香酸 である請求項28記載の化合物。 30.W2がFであり、W3がFである請求項27記載の化合物。 31.メチル2,6−ジフルオロ−4−[(3',5'−ジ−t−ブチルフェニル) カルバモイル]ベンゾエート;または 2,6−ジフルオロ−4−[(3',5'−ジ−t−ブチルフェニル)カルバモイル] 安息香酸 である請求項30記載の化合物。 32.W1がOHである請求項27記載の化合物。 33.エチル2−フルオロ−4−[(2'−ヒドロキシ−3',5'−ジ−t−ブチ ルフェニル)カルバモイル]ベンゾエート;または 2−フルオロ−4−[(2'−ヒドロキシ−3',5'−ジ−t−ブチルフェニル) カルバモイル]安息香酸 である請求項32記載の化合物。
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US08/561,999 | 1995-11-22 | ||
US08/561,999 US5663357A (en) | 1995-11-22 | 1995-11-22 | Substituted heteroarylamides having retinoid-like biological activity |
PCT/US1996/018529 WO1997019062A1 (en) | 1995-11-22 | 1996-11-19 | Substituted aryl or heteroarylamides having retinoid-like biological activity |
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-
1995
- 1995-11-22 US US08/561,999 patent/US5663357A/en not_active Expired - Lifetime
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1996
- 1996-11-18 KR KR1019980703816A patent/KR100483442B1/ko not_active IP Right Cessation
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- 1996-11-19 AU AU10551/97A patent/AU715624B2/en not_active Ceased
- 1996-11-19 CA CA002238310A patent/CA2238310A1/en not_active Abandoned
- 1996-11-19 IL IL14374796A patent/IL143747A0/xx unknown
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- 1996-11-19 EP EP96941395A patent/EP0862555B1/en not_active Expired - Lifetime
- 1996-11-19 IL IL14374896A patent/IL143748A0/xx unknown
- 1996-11-19 BR BR9611615A patent/BR9611615A/pt not_active Application Discontinuation
- 1996-11-19 WO PCT/US1996/018529 patent/WO1997019062A1/en active IP Right Grant
- 1996-11-19 HU HU9901993A patent/HUP9901993A3/hu unknown
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- 1996-11-19 DE DE69633679T patent/DE69633679T2/de not_active Expired - Fee Related
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- 1996-11-19 AT AT96941395T patent/ATE280160T1/de not_active IP Right Cessation
- 1996-11-19 CN CN96199731A patent/CN1207727A/zh active Pending
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Also Published As
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KR19990071542A (ko) | 1999-09-27 |
US6245786B1 (en) | 2001-06-12 |
IL124593A0 (en) | 1998-12-06 |
ATE280160T1 (de) | 2004-11-15 |
CA2238310A1 (en) | 1997-05-29 |
US5917048A (en) | 1999-06-29 |
JP4125785B2 (ja) | 2008-07-30 |
IL143747A0 (en) | 2002-04-21 |
IL124593A (en) | 2002-09-12 |
US6320047B1 (en) | 2001-11-20 |
PL326925A1 (en) | 1998-11-09 |
EP0862555B1 (en) | 2004-10-20 |
US20020091262A1 (en) | 2002-07-11 |
CN1207727A (zh) | 1999-02-10 |
US6051713A (en) | 2000-04-18 |
AU1055197A (en) | 1997-06-11 |
HUP9901993A3 (en) | 2001-10-29 |
EP0862555A1 (en) | 1998-09-09 |
US6437129B1 (en) | 2002-08-20 |
BR9611615A (pt) | 1999-05-25 |
KR100483442B1 (ko) | 2006-04-21 |
DE69633679T2 (de) | 2006-02-09 |
MX9804103A (es) | 1998-09-30 |
MX206851B (es) | 2002-02-25 |
US5663357A (en) | 1997-09-02 |
DE69633679D1 (de) | 2004-11-25 |
NZ323574A (en) | 1999-10-28 |
WO1997019062A1 (en) | 1997-05-29 |
MX230771B (es) | 2005-09-21 |
HUP9901993A2 (hu) | 1999-10-28 |
AU715624B2 (en) | 2000-02-03 |
IL143748A0 (en) | 2002-04-21 |
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