JP4410562B2 - 置換尿素レチノイド作用薬ii - Google Patents
置換尿素レチノイド作用薬ii Download PDFInfo
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- JP4410562B2 JP4410562B2 JP2003528768A JP2003528768A JP4410562B2 JP 4410562 B2 JP4410562 B2 JP 4410562B2 JP 2003528768 A JP2003528768 A JP 2003528768A JP 2003528768 A JP2003528768 A JP 2003528768A JP 4410562 B2 JP4410562 B2 JP 4410562B2
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- Prior art keywords
- alkyl
- group
- hydrogen
- acid
- cycloalkyl
- Prior art date
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- -1 urea retinoid Chemical class 0.000 title description 98
- 239000000556 agonist Substances 0.000 title description 14
- 239000004202 carbamide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- AMDKYPNODLTUMY-UHFFFAOYSA-N 5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-amine Chemical compound NC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 AMDKYPNODLTUMY-UHFFFAOYSA-N 0.000 description 14
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- 241000700159 Rattus Species 0.000 description 12
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 9
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- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- 239000005711 Benzoic acid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 235000010233 benzoic acid Nutrition 0.000 description 7
- 230000003247 decreasing effect Effects 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000008439 repair process Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 238000013270 controlled release Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- MUMMFUHTGZMKLE-UHFFFAOYSA-N 4-[[benzyl-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]amino]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1N(C(=O)NC=1C=CC(=CC=1)C(O)=O)CC1=CC=CC=C1 MUMMFUHTGZMKLE-UHFFFAOYSA-N 0.000 description 5
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- 125000004104 aryloxy group Chemical group 0.000 description 5
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- 229940112141 dry powder inhaler Drugs 0.000 description 5
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- QUFUDPIKWMMKJC-UHFFFAOYSA-N 1,1,4,4-tetramethyl-2-nitro-2,3-dihydronaphthalene Chemical compound C1=CC=C2C(C)(C)CC([N+]([O-])=O)C(C)(C)C2=C1 QUFUDPIKWMMKJC-UHFFFAOYSA-N 0.000 description 4
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- BBLTZMAZYGBBND-UHFFFAOYSA-N 4-[[2-methoxyethyl-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]amino]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1N(CCOC)C(=O)NC1=CC=C(C(O)=O)C=C1 BBLTZMAZYGBBND-UHFFFAOYSA-N 0.000 description 4
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- FIKOUKBRWXICOI-UHFFFAOYSA-N 4-[[4-phenylmethoxybutyl-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]amino]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1N(C(=O)NC=1C=CC(=CC=1)C(O)=O)CCCCOCC1=CC=CC=C1 FIKOUKBRWXICOI-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32296201P | 2001-09-18 | 2001-09-18 | |
| PCT/EP2002/010181 WO2003024920A1 (en) | 2001-09-18 | 2002-09-11 | Substituted urea retinoid agonists ii |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503411A JP2005503411A (ja) | 2005-02-03 |
| JP2005503411A5 JP2005503411A5 (enExample) | 2006-01-05 |
| JP4410562B2 true JP4410562B2 (ja) | 2010-02-03 |
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| JP2003528768A Expired - Fee Related JP4410562B2 (ja) | 2001-09-18 | 2002-09-11 | 置換尿素レチノイド作用薬ii |
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| EP (1) | EP1430023B1 (enExample) |
| JP (1) | JP4410562B2 (enExample) |
| KR (1) | KR100891224B1 (enExample) |
| CN (1) | CN1301968C (enExample) |
| AR (1) | AR036532A1 (enExample) |
| AT (1) | ATE427929T1 (enExample) |
| AU (1) | AU2002340886B2 (enExample) |
| BR (1) | BR0212607A (enExample) |
| CA (1) | CA2458266C (enExample) |
| DE (1) | DE60231888D1 (enExample) |
| ES (1) | ES2325063T3 (enExample) |
| MX (1) | MXPA04002305A (enExample) |
| PL (1) | PL209697B1 (enExample) |
| RU (1) | RU2303027C2 (enExample) |
| WO (1) | WO2003024920A1 (enExample) |
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| EP1889830A1 (en) | 2006-07-10 | 2008-02-20 | Pharmeste S.r.l. | Biarylcarboxyarylamides as vanilloid-1 receptor modulators |
| EP1889837A1 (en) * | 2006-07-10 | 2008-02-20 | Pharmeste S.r.l. | VR1 vanilloid receptor antagonists with a iononic substructure |
| EP4066826B1 (en) | 2010-09-01 | 2024-03-06 | Thomas Jefferson University | Retinoic acid receptor gamma agonists for muscle repair and regeneration |
| CN105188753B (zh) | 2012-11-08 | 2018-12-18 | 国立大学法人山口大学 | 角结膜病症的治疗剂 |
| DK3000466T3 (en) | 2013-05-22 | 2018-11-26 | Univ Yamaguchi | INHIBITOR FOR RETINOCHOROIDAL DISEASES |
| CA3025854A1 (en) | 2016-06-08 | 2017-12-14 | Clementia Pharmaceuticals Inc. | Methods for treating heterotopic ossification |
| EP3541380B1 (en) | 2016-11-16 | 2021-12-15 | Clementia Pharmaceuticals Inc. | Methods for treating multiple osteochondroma (mo) |
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| LU87821A1 (fr) * | 1990-10-12 | 1992-05-25 | Cird Galderma | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique |
| HUT62558A (en) * | 1991-07-01 | 1993-05-28 | Sandoz Ag | Process for producing n-phenylthiourea derivaties and pharmaceutical compositions comprising same |
| US5599967A (en) * | 1994-12-29 | 1997-02-04 | Allergan | Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl of heteroaryl group having retinoid-like biological activity |
| US5648514A (en) * | 1994-12-29 | 1997-07-15 | Allergan | Substituted acetylenes having retinoid-like biological activity |
| US6093742A (en) * | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| JO2178B1 (en) * | 1999-10-19 | 2003-04-23 | اف . هوفمان لاروش ايه جي | Treatment of invasive diseases, using selected anti-PAR materials |
-
2002
- 2002-09-11 KR KR1020047003921A patent/KR100891224B1/ko not_active Expired - Fee Related
- 2002-09-11 AT AT02774599T patent/ATE427929T1/de active
- 2002-09-11 PL PL370459A patent/PL209697B1/pl not_active IP Right Cessation
- 2002-09-11 AU AU2002340886A patent/AU2002340886B2/en not_active Ceased
- 2002-09-11 RU RU2004111789/04A patent/RU2303027C2/ru not_active IP Right Cessation
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- 2002-09-11 JP JP2003528768A patent/JP4410562B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2458266C (en) | 2011-03-15 |
| EP1430023A1 (en) | 2004-06-23 |
| MXPA04002305A (es) | 2004-06-29 |
| KR20040035808A (ko) | 2004-04-29 |
| CN1301968C (zh) | 2007-02-28 |
| RU2004111789A (ru) | 2005-10-20 |
| AU2002340886B2 (en) | 2008-01-31 |
| KR100891224B1 (ko) | 2009-04-01 |
| US20030125383A1 (en) | 2003-07-03 |
| BR0212607A (pt) | 2004-08-17 |
| WO2003024920A1 (en) | 2003-03-27 |
| AR036532A1 (es) | 2004-09-15 |
| CN1555357A (zh) | 2004-12-15 |
| PL370459A1 (en) | 2005-05-30 |
| ATE427929T1 (de) | 2009-04-15 |
| ES2325063T3 (es) | 2009-08-25 |
| DE60231888D1 (de) | 2009-05-20 |
| JP2005503411A (ja) | 2005-02-03 |
| US6838472B2 (en) | 2005-01-04 |
| PL209697B1 (pl) | 2011-10-31 |
| RU2303027C2 (ru) | 2007-07-20 |
| CA2458266A1 (en) | 2003-03-27 |
| EP1430023B1 (en) | 2009-04-08 |
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