JP2009537540A5 - - Google Patents
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- JP2009537540A5 JP2009537540A5 JP2009511053A JP2009511053A JP2009537540A5 JP 2009537540 A5 JP2009537540 A5 JP 2009537540A5 JP 2009511053 A JP2009511053 A JP 2009511053A JP 2009511053 A JP2009511053 A JP 2009511053A JP 2009537540 A5 JP2009537540 A5 JP 2009537540A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- carbons
- rar
- composition
- 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
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- 102000003702 retinoic acid receptors Human genes 0.000 claims description 125
- 108090000064 retinoic acid receptors Proteins 0.000 claims description 125
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- 239000005557 antagonist Substances 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 229940125425 inverse agonist Drugs 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 241000124008 Mammalia Species 0.000 claims description 21
- 238000002512 chemotherapy Methods 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 238000001959 radiotherapy Methods 0.000 claims description 18
- 206010043554 thrombocytopenia Diseases 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 208000004235 neutropenia Diseases 0.000 claims description 13
- LHUPKWKWYWOMSK-UHFFFAOYSA-N 4-[2-[4-(4-ethylphenyl)-2,2-dimethylthiochromen-6-yl]ethynyl]benzoic acid Chemical group C1=CC(CC)=CC=C1C1=CC(C)(C)SC2=CC=C(C#CC=3C=CC(=CC=3)C(O)=O)C=C12 LHUPKWKWYWOMSK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 230000003247 decreasing effect Effects 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 102100023606 Retinoic acid receptor alpha Human genes 0.000 claims description 11
- 102100033909 Retinoic acid receptor beta Human genes 0.000 claims description 11
- 102100033912 Retinoic acid receptor gamma Human genes 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 102000005962 receptors Human genes 0.000 claims description 11
- 108020003175 receptors Proteins 0.000 claims description 11
- 108091008726 retinoic acid receptors α Proteins 0.000 claims description 11
- 108091008761 retinoic acid receptors β Proteins 0.000 claims description 11
- 108091008760 retinoic acid receptors γ Proteins 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 210000000440 neutrophil Anatomy 0.000 claims description 10
- 125000002971 oxazolyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 210000001185 bone marrow Anatomy 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 230000003394 haemopoietic effect Effects 0.000 claims description 8
- BUGXGZOGQGUTBC-UHFFFAOYSA-N 4-[[3-bromo-4-ethoxy-5-(4-methylbenzoyl)benzoyl]amino]benzoic acid Chemical group CCOC1=C(Br)C=C(C(=O)NC=2C=CC(=CC=2)C(O)=O)C=C1C(=O)C1=CC=C(C)C=C1 BUGXGZOGQGUTBC-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- 206010065553 Bone marrow failure Diseases 0.000 claims description 5
- 208000007502 anemia Diseases 0.000 claims description 5
- 201000002364 leukopenia Diseases 0.000 claims description 5
- 231100001022 leukopenia Toxicity 0.000 claims description 5
- -1 1-ademantyl Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 238000010322 bone marrow transplantation Methods 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 210000005259 peripheral blood Anatomy 0.000 claims description 4
- 239000011886 peripheral blood Substances 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 230000036737 immune function Effects 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 210000000130 stem cell Anatomy 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical group C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 201000004384 Alopecia Diseases 0.000 claims description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 2
- 208000019838 Blood disease Diseases 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 206010025327 Lymphopenia Diseases 0.000 claims description 2
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 206010033661 Pancytopenia Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 231100000360 alopecia Toxicity 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 208000014951 hematologic disease Diseases 0.000 claims description 2
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 2
- 208000018706 hematopoietic system disease Diseases 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 231100001023 lymphopenia Toxicity 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
- 208000003265 stomatitis Diseases 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 61
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 229940096885 Retinoic acid receptor agonist Drugs 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 56
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000007115 recruitment Effects 0.000 description 3
- 230000006041 cell recruitment Effects 0.000 description 2
- 0 CC(C)(C)c1cc(C(*c2ccc(*)cc2)=O)cc(C(C)(C)C)c1OI(C)C Chemical compound CC(C)(C)c1cc(C(*c2ccc(*)cc2)=O)cc(C(C)(C)C)c1OI(C)C 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80077306P | 2006-05-16 | 2006-05-16 | |
| PCT/US2007/011730 WO2007136653A2 (en) | 2006-05-16 | 2007-05-16 | Use of a rar antagonist or inverse agonist for the treatment of chemotherapy and/or radiation therapy side effects |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009537540A JP2009537540A (ja) | 2009-10-29 |
| JP2009537540A5 true JP2009537540A5 (enExample) | 2011-07-21 |
Family
ID=38566762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009511053A Pending JP2009537540A (ja) | 2006-05-16 | 2007-05-16 | 化学療法および／または放射線療法の副作用を処置するためのｒａｒアンタゴニストまたはｒａｒインバースアゴニストの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9271946B2 (enExample) |
| EP (1) | EP2026778B1 (enExample) |
| JP (1) | JP2009537540A (enExample) |
| CN (1) | CN101472572B (enExample) |
| CA (1) | CA2651487A1 (enExample) |
| DK (1) | DK2026778T3 (enExample) |
| ES (1) | ES2702128T3 (enExample) |
| TR (1) | TR201819157T4 (enExample) |
| WO (1) | WO2007136653A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013004685B1 (pt) | 2010-09-01 | 2021-09-21 | Thomas Jefferson University | Uso de um agonista de receptor gama de ácido retinóico (rar?) para reparação e regeneração muscular |
| EP2858636B1 (en) * | 2012-06-07 | 2018-09-05 | Childrens Hospital Los Angeles | Methods for treating neutropenia using retinoid agonists |
| CA2890424C (en) | 2012-11-08 | 2020-11-17 | Yamaguchi University | Therapeutic agent for keratoconjunctive disorders |
| WO2014110165A1 (en) * | 2013-01-08 | 2014-07-17 | Io Therapeutics, Inc. | Treatment of graft-versus-host disease disorders using rar antagonists |
| EP3000466B1 (en) | 2013-05-22 | 2018-08-15 | Yamaguchi University | Inhibitor for retinochoroidal disorders |
| CN106413701A (zh) | 2014-02-18 | 2017-02-15 | 洛杉矶儿童医院 | 用于治疗中性粒细胞减少症的组合物和方法 |
| PL3380086T3 (pl) | 2015-11-25 | 2022-02-21 | Io Therapeutics, Inc. | Oporne na cyp26 agonisty selektywne względem rar-alfa w leczeniu nowotworu |
| WO2017201200A1 (en) * | 2016-05-19 | 2017-11-23 | Orphagen Pharmaceuticals, Inc. | Therapeutic compositions containing rar-alpha antagonists |
| EP3468554B1 (en) | 2016-06-08 | 2023-08-09 | Clementia Pharmaceuticals Inc. | Methods for treating heterotopic ossification |
| CA3026563C (en) | 2016-06-10 | 2023-11-28 | Io Therapeutics, Inc. | Receptor selective retinoid and rexinoid compounds and immune modulators for cancer immunotherapy |
| JP7018957B2 (ja) | 2016-11-16 | 2022-02-14 | クレメンティア ファーマシューティカルズ インコーポレイテッド | 多発性骨軟骨腫（ｍｏ）を処置するための方法 |
| EP3651757A4 (en) * | 2017-07-13 | 2021-08-25 | IO Therapeutics, Inc. | RECEPTOR SUB-TYPE AND SELECTIVE RETINOID AND REXINOID COMPOUNDS FOR A FUNCTION IN COMBINATION WITH IMMUNE MODULATORS FOR ANTI-CANCER IMMUNOTHERAPY |
| AU2018326617B2 (en) | 2017-08-31 | 2022-12-01 | Io Therapeutics, Inc. | Rar selective agonists in combination with immune modulators for cancer immunotherapy |
| CN113207799B (zh) * | 2021-03-19 | 2022-03-15 | 中山大学 | 一种二型糖尿病小鼠快速心衰模型的构建方法 |
| CN115974860B (zh) * | 2022-12-15 | 2024-09-24 | 复旦大学附属中山医院 | 维甲酸类化合物及其制备方法和用途、含该化合物的药物组合物 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2102195T3 (es) | 1992-12-28 | 1997-07-16 | Eisai Co Ltd | Derivados heterociclicos de acido carbonico que se fijan en receptores de retinoides. |
| US6008204A (en) * | 1995-09-01 | 1999-12-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5958954A (en) | 1995-09-01 | 1999-09-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5776699A (en) | 1995-09-01 | 1998-07-07 | Allergan, Inc. | Method of identifying negative hormone and/or antagonist activities |
| US5952345A (en) | 1995-09-01 | 1999-09-14 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US6218128B1 (en) | 1997-09-12 | 2001-04-17 | Allergan Sales, Inc. | Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities |
| US6942980B1 (en) | 1995-09-01 | 2005-09-13 | Allergan, Inc. | Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities |
| US20030219832A1 (en) | 1996-03-11 | 2003-11-27 | Klein Elliott S. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5877207A (en) | 1996-03-11 | 1999-03-02 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US6555690B2 (en) | 1996-06-21 | 2003-04-29 | Allergan, Inc. | Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US5773594A (en) | 1996-06-21 | 1998-06-30 | Allergan | Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US5763635A (en) | 1996-06-21 | 1998-06-09 | Allergan | Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity |
| US5739338A (en) | 1996-11-05 | 1998-04-14 | Allergan | N-aryl substituted tetrahydroquinolines having retinoid agonist, retinoid antagonist or retinoid inverse agonist type biological activity |
| US5728846A (en) | 1996-12-12 | 1998-03-17 | Allergan | Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives |
| US6037488A (en) | 1997-04-19 | 2000-03-14 | Allergan Sales, Inc. | Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity |
| US5919970A (en) | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
| US6521641B1 (en) | 1998-10-08 | 2003-02-18 | Allergan, Inc. | Male anti-fertility agents |
| US6043381A (en) | 1999-05-07 | 2000-03-28 | Allergan Sales, Inc. | Process for preparing substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo[1,2-g]-1,2-dihydroquinoline derivatives |
| US6313168B1 (en) | 1999-12-15 | 2001-11-06 | Allergan Sales, Inc. | Use of retinoid receptor antagonists in the treatment of cartilage and bone pathologies |
| US20020193403A1 (en) | 2001-05-03 | 2002-12-19 | Allergan Sales, Inc. | Methods of treating hyperlipidemia |
| JP2004528368A (ja) * | 2001-05-08 | 2004-09-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 抗ｅｇｆｒ抗体と抗ホルモン剤を用いた組合せ療法 |
| IL152904A0 (en) * | 2002-01-24 | 2003-06-24 | Gamida Cell Ltd | Utilization of retinoid and vitamin d receptor antagonists for expansion of renewable stem cell populations |
| WO2003078567A2 (en) * | 2002-03-18 | 2003-09-25 | Gamida-Cell Ltd. | Methods of inducing differentiation in ex vivo expanded stem cells |
| JP2006511443A (ja) * | 2002-06-04 | 2006-04-06 | ガルデルマ・リサーチ・アンド・デヴェロップメント・エス・エヌ・セ | Ｒａｒ受容体の阻害剤である新規のリガンド、その調製方法およびヒト用の医薬品および化粧品におけるその使用 |
| US7105566B2 (en) * | 2002-10-22 | 2006-09-12 | Allergan, Inc. | Methods of treatment during vascular procedures |
| AU2003298239A1 (en) * | 2002-11-18 | 2004-06-15 | Galderma Research And Development, S.N.C. | Novel ligands that are antagonists of raf receptors, process for preparing them and use thereof in human medicine and in cosmetics |
-
2007
- 2007-05-16 JP JP2009511053A patent/JP2009537540A/ja active Pending
- 2007-05-16 TR TR2018/19157T patent/TR201819157T4/tr unknown
- 2007-05-16 CA CA002651487A patent/CA2651487A1/en not_active Abandoned
- 2007-05-16 ES ES07794936T patent/ES2702128T3/es active Active
- 2007-05-16 WO PCT/US2007/011730 patent/WO2007136653A2/en not_active Ceased
- 2007-05-16 DK DK07794936.0T patent/DK2026778T3/en active
- 2007-05-16 CN CN2007800222950A patent/CN101472572B/zh not_active Expired - Fee Related
- 2007-05-16 EP EP07794936.0A patent/EP2026778B1/en not_active Not-in-force
-
2008
- 2008-11-13 US US12/291,994 patent/US9271946B2/en not_active Expired - Fee Related
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