JP2004509955A5 - - Google Patents
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- JP2004509955A5 JP2004509955A5 JP2002531111A JP2002531111A JP2004509955A5 JP 2004509955 A5 JP2004509955 A5 JP 2004509955A5 JP 2002531111 A JP2002531111 A JP 2002531111A JP 2002531111 A JP2002531111 A JP 2002531111A JP 2004509955 A5 JP2004509955 A5 JP 2004509955A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbon atoms
- pharmaceutically acceptable
- compound
- acceptable base
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 description 190
- 125000004432 carbon atom Chemical group C* 0.000 description 189
- 150000001875 compounds Chemical class 0.000 description 80
- 150000001768 cations Chemical class 0.000 description 64
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 28
- 102100039282 Cytochrome P450 26A1 Human genes 0.000 description 24
- 101710130818 Cytochrome P450 26A1 Proteins 0.000 description 24
- 102000004190 Enzymes Human genes 0.000 description 24
- 108090000790 Enzymes Proteins 0.000 description 24
- 241000124008 Mammalia Species 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 23
- 230000002401 inhibitory effect Effects 0.000 description 23
- 229910052740 iodine Inorganic materials 0.000 description 23
- 239000008194 pharmaceutical composition Substances 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 229910052731 fluorine Inorganic materials 0.000 description 19
- 125000001072 heteroaryl group Chemical group 0.000 description 19
- -1 1-imidazolyl Chemical group 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- 125000004414 alkyl thio group Chemical group 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 229910052736 halogen Chemical group 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 10
- 125000002541 furyl group Chemical group 0.000 description 9
- 125000002883 imidazolyl group Chemical group 0.000 description 9
- 125000002971 oxazolyl group Chemical group 0.000 description 9
- 125000003373 pyrazinyl group Chemical group 0.000 description 9
- 125000003226 pyrazolyl group Chemical group 0.000 description 9
- 125000002098 pyridazinyl group Chemical group 0.000 description 9
- 125000004076 pyridyl group Chemical group 0.000 description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 125000000335 thiazolyl group Chemical group 0.000 description 9
- 125000001544 thienyl group Chemical group 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 0 *CC1C#CC(O)=CC1 Chemical compound *CC1C#CC(O)=CC1 0.000 description 1
- XMNHGDPCBNIWFV-UHFFFAOYSA-N 2-[2-fluoro-4-[2-(2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]phenyl]acetic acid Chemical compound C=1C=C2OC(C)(C)CC(C)(C)C2=CC=1C#CC1=CC=C(CC(O)=O)C(F)=C1 XMNHGDPCBNIWFV-UHFFFAOYSA-N 0.000 description 1
- JBKIUXYXZUSWPS-UHFFFAOYSA-N 2-[4-(8,8-dimethyl-5-oxo-6,7-dihydronaphthalene-2-carbonyl)oxyphenyl]acetic acid Chemical compound C1=C2C(C)(C)CCC(=O)C2=CC=C1C(=O)OC1=CC=C(CC(O)=O)C=C1 JBKIUXYXZUSWPS-UHFFFAOYSA-N 0.000 description 1
- ITXFQVKXIVKNHH-UHFFFAOYSA-N 2-[4-[2-(2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]phenyl]acetic acid Chemical compound C=1C=C2OC(C)(C)CC(C)(C)C2=CC=1C#CC1=CC=C(CC(O)=O)C=C1 ITXFQVKXIVKNHH-UHFFFAOYSA-N 0.000 description 1
- DGFTWCCCWFYBFB-UHFFFAOYSA-N 2-[4-[2-(5-imidazol-1-yl-8,8-dimethyl-6,7-dihydro-5h-naphthalen-2-yl)ethynyl]phenyl]acetic acid Chemical compound C1=C2C(C)(C)CCC(N3C=NC=C3)C2=CC=C1C#CC1=CC=C(CC(O)=O)C=C1 DGFTWCCCWFYBFB-UHFFFAOYSA-N 0.000 description 1
- LWCBOTGILHXRHK-UHFFFAOYSA-N 2-[4-[2-(8,8-dimethyl-5-oxo-6,7-dihydronaphthalen-2-yl)ethynyl]-2-fluorophenyl]acetic acid Chemical compound C1=C2C(C)(C)CCC(=O)C2=CC=C1C#CC1=CC=C(CC(O)=O)C(F)=C1 LWCBOTGILHXRHK-UHFFFAOYSA-N 0.000 description 1
- LYOAHZUZZNMLNC-UHFFFAOYSA-N 2-[4-[2-(8-cyclopropyl-2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]-2-fluorophenyl]acetic acid Chemical compound C=12OC(C)(C)CC(C)(C)C2=CC(C#CC=2C=C(F)C(CC(O)=O)=CC=2)=CC=1C1CC1 LYOAHZUZZNMLNC-UHFFFAOYSA-N 0.000 description 1
- FKURZNWAFOUMKK-UHFFFAOYSA-N 2-[4-[2-(8-cyclopropyl-2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]phenyl]acetic acid Chemical compound C=12OC(C)(C)CC(C)(C)C2=CC(C#CC=2C=CC(CC(O)=O)=CC=2)=CC=1C1CC1 FKURZNWAFOUMKK-UHFFFAOYSA-N 0.000 description 1
- UBXQMNPDZOGDSY-UHFFFAOYSA-N 2-[4-[2-(8-ethyl-2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]phenyl]acetic acid Chemical compound C=1C(C(CC(C)(C)O2)(C)C)=C2C(CC)=CC=1C#CC1=CC=C(CC(O)=O)C=C1 UBXQMNPDZOGDSY-UHFFFAOYSA-N 0.000 description 1
- WNJLJQKQEKVIJT-UHFFFAOYSA-N 2-fluoro-4-[2-(2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]benzoic acid Chemical compound C=1C=C2OC(C)(C)CC(C)(C)C2=CC=1C#CC1=CC=C(C(O)=O)C(F)=C1 WNJLJQKQEKVIJT-UHFFFAOYSA-N 0.000 description 1
- VSHLPGYGJSORKV-UHFFFAOYSA-N 4-[2-(8,8-dimethyl-5-oxo-6,7-dihydronaphthalen-2-yl)ethynyl]-2-fluorobenzoic acid Chemical compound C1=C2C(C)(C)CCC(=O)C2=CC=C1C#CC1=CC=C(C(O)=O)C(F)=C1 VSHLPGYGJSORKV-UHFFFAOYSA-N 0.000 description 1
- QELVCKRITXHFTQ-UHFFFAOYSA-N 4-[2-(8-cyclopropyl-2,2,4,4-tetramethyl-3h-chromen-6-yl)ethynyl]benzoic acid Chemical compound C=12OC(C)(C)CC(C)(C)C2=CC(C#CC=2C=CC(=CC=2)C(O)=O)=CC=1C1CC1 QELVCKRITXHFTQ-UHFFFAOYSA-N 0.000 description 1
- CVJNXBWYODEEOO-UHFFFAOYSA-N 4-[2-[5-[cyclopropyl(methyl)amino]-8,8-dimethyl-6,7-dihydro-5h-naphthalen-2-yl]ethynyl]-2-fluorobenzoic acid Chemical compound C1CC(C)(C)C2=CC(C#CC=3C=C(F)C(C(O)=O)=CC=3)=CC=C2C1N(C)C1CC1 CVJNXBWYODEEOO-UHFFFAOYSA-N 0.000 description 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 description 1
- XJTOPAXEUDXMNT-UHFFFAOYSA-N COC(CC1C(F)=CC(I)=CC1)=O Chemical compound COC(CC1C(F)=CC(I)=CC1)=O XJTOPAXEUDXMNT-UHFFFAOYSA-N 0.000 description 1
- IYIVBGQBEMSRLO-UHFFFAOYSA-N COC(Cc(cc1)ccc1I)=O Chemical compound COC(Cc(cc1)ccc1I)=O IYIVBGQBEMSRLO-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/672,751 US6313107B1 (en) | 2000-08-29 | 2000-09-28 | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
| PCT/US2001/025465 WO2002026727A2 (en) | 2000-09-28 | 2001-08-14 | Methods of providing and using compounds (retinoids) having activity as inhibitors of cytochrome p450rai |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004509955A JP2004509955A (ja) | 2004-04-02 |
| JP2004509955A5 true JP2004509955A5 (enExample) | 2008-11-20 |
Family
ID=24699854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002531111A Pending JP2004509955A (ja) | 2000-09-28 | 2001-08-14 | シトクロムｐ４５０ｒａｉ阻害剤としての活性を有する化合物（レチノイド）を提供および使用する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6313107B1 (enExample) |
| EP (1) | EP1322631A2 (enExample) |
| JP (1) | JP2004509955A (enExample) |
| AU (2) | AU2001286478B2 (enExample) |
| CA (1) | CA2423919A1 (enExample) |
| WO (1) | WO2002026727A2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6313107B1 (en) * | 2000-08-29 | 2001-11-06 | Allergan Sales, Inc. | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
| CA2495537C (en) * | 2000-08-29 | 2010-03-30 | Nobex Corporation | Immunoregulatory compounds and derivatives and methods of treating diseases therewith |
| US8048924B2 (en) | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| JP5082033B2 (ja) | 2001-12-21 | 2012-11-28 | エグゼリクシス パテント カンパニー エルエルシー | Ｌｘｒのモジュレーター |
| US6740676B2 (en) * | 2002-03-19 | 2004-05-25 | Allergan, Inc. | 4-[(8-ethynyl, 8-vinyl or 8-ethynyl-methyl)-6-chromanoyl]-benzoic and 2-[4-[(8-ethynyl, 8-vinyl or 8-ethynyl-methyl)-6-chromanoyl]-phenyl]-acetic acid, their esters and salts having cytochrome p450rai inhibitory activity |
| US20090181966A1 (en) * | 2002-10-04 | 2009-07-16 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| US7504508B2 (en) * | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| MXPA05003456A (es) * | 2002-10-04 | 2005-07-05 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| US6683092B1 (en) | 2003-04-09 | 2004-01-27 | Allergan, Inc. | [3-(c5-14alkyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-phenyl and [3-(c5-14alkyl-2-oxo-1,2,3,4- tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-heteroaryl derivatives having anti-tumor activity |
| US6734193B1 (en) | 2003-06-03 | 2004-05-11 | Allergan, Inc. | (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| US7468391B2 (en) | 2003-12-17 | 2008-12-23 | Allergan, Inc. | Methods for treating retinoid responsive disorders using selective inhibitors of CYP26A and CYP26B |
| US7226951B2 (en) * | 2003-12-17 | 2007-06-05 | Allergan, Inc. | Compounds having selective cytochrome P450RAI-1 or selective cytochrome P450RAI-2 inhibitory activity and methods of obtaining the same |
| JP4884963B2 (ja) | 2004-03-10 | 2012-02-29 | 財団法人乙卯研究所 | 記憶固定促進剤 |
| EP1773767B1 (en) | 2004-07-07 | 2016-03-09 | Biocon Limited | Synthesis of azo bonded immunoregulatory compounds |
| AU2005316739A1 (en) * | 2004-12-13 | 2006-06-22 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| CA2598133A1 (en) * | 2005-02-24 | 2006-08-31 | Millennium Pharmaceuticals, Inc. | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
| US7811261B2 (en) | 2008-06-02 | 2010-10-12 | Sta-Med, Llc | Needle cover assembly for a syringe |
| US8586607B2 (en) * | 2008-07-28 | 2013-11-19 | Syddansk Universitet | Compounds for the treatment of metabolic diseases |
| US8162882B2 (en) | 2010-06-23 | 2012-04-24 | Sta-Med, Llc | Automatic-locking safety needle covers and methods of use and manufacture |
| AU2012213086B2 (en) | 2011-02-03 | 2016-05-05 | Lupin Limited | Pyrrole derivatives used as modulators of alpha7 nAChR |
| WO2012166746A1 (en) | 2011-05-31 | 2012-12-06 | Sta-Med, Llc | Blood collection safety devices and methods of use and manufacture |
| CA2848540A1 (en) | 2011-09-15 | 2013-03-21 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona Acting For And On Behalf Of Arizona State University | Therapeutic compounds |
| WO2015109318A2 (en) | 2014-01-17 | 2015-07-23 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting For And On Behalf Of Arizona State University | Therapeutic methods |
| CN107176945B (zh) * | 2016-03-11 | 2021-06-08 | 中国科学院上海有机化学研究所 | 一种视黄酸类化合物、其制备方法、中间体及应用 |
| US10238655B2 (en) | 2017-01-23 | 2019-03-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Dihydroindene and tetrahydronaphthalene compounds |
| US10238626B2 (en) | 2017-01-23 | 2019-03-26 | Arizona Board Of Regents On Behalf Of Arizona State University | Therapeutic compounds |
| US10231947B2 (en) | 2017-01-23 | 2019-03-19 | Arizona Board Of Regents On Behalf Of Arizona State University | Isochroman compounds and methods of use thereof |
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-
2000
- 2000-09-28 US US09/672,751 patent/US6313107B1/en not_active Expired - Fee Related
-
2001
- 2001-06-07 US US09/963,318 patent/US6495552B2/en not_active Expired - Fee Related
- 2001-06-07 US US09/875,967 patent/US6387892B1/en not_active Expired - Fee Related
- 2001-08-14 WO PCT/US2001/025465 patent/WO2002026727A2/en not_active Ceased
- 2001-08-14 EP EP01965927A patent/EP1322631A2/en not_active Withdrawn
- 2001-08-14 JP JP2002531111A patent/JP2004509955A/ja active Pending
- 2001-08-14 AU AU2001286478A patent/AU2001286478B2/en not_active Ceased
- 2001-08-14 AU AU8647801A patent/AU8647801A/xx active Pending
- 2001-08-14 CA CA002423919A patent/CA2423919A1/en not_active Abandoned
-
2002
- 2002-08-05 US US10/212,533 patent/US6855512B2/en not_active Expired - Fee Related
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