JP2005531526A - Ｐｄｅ７阻害剤としての（４，２−２置換−チアゾール−５−イル）アミン化合物 - Google Patents
Ｐｄｅ７阻害剤としての（４，２−２置換−チアゾール−５−イル）アミン化合物 Download PDFInfo
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- JP2005531526A JP2005531526A JP2003580307A JP2003580307A JP2005531526A JP 2005531526 A JP2005531526 A JP 2005531526A JP 2003580307 A JP2003580307 A JP 2003580307A JP 2003580307 A JP2003580307 A JP 2003580307A JP 2005531526 A JP2005531526 A JP 2005531526A
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- -1 amine compounds Chemical class 0.000 title claims description 23
- 239000002606 phosphodiesterase VII inhibitor Substances 0.000 title claims description 10
- 229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 15
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 150000008043 acidic salts Chemical class 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 150000001447 alkali salts Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 11
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- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 3H-quinazolinyl-4-one Natural products C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
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- 238000000034 method Methods 0.000 claims description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
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- 238000000746 purification Methods 0.000 claims description 5
- WSCDRWOCBCZPPE-UHFFFAOYSA-N 2-(4-aminoquinazolin-7-yl)-n-cyclohexyl-4-methyl-1,3-thiazol-5-amine Chemical compound CC=1N=C(C=2C=C3N=CN=C(N)C3=CC=2)SC=1NC1CCCCC1 WSCDRWOCBCZPPE-UHFFFAOYSA-N 0.000 claims description 4
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- 239000013543 active substance Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- REDAJIBZNZJTLQ-UHFFFAOYSA-N n-[4-[5-(cyclohexylamino)-4-methyl-1,3-thiazol-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NC(C)=C1NC1CCCCC1 REDAJIBZNZJTLQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
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- 239000011593 sulfur Substances 0.000 claims description 4
- ZANWTKIZLOFGNH-UHFFFAOYSA-N 4-methyl-n,2-diphenyl-1,3-thiazol-5-amine Chemical compound CC=1N=C(C=2C=CC=CC=2)SC=1NC1=CC=CC=C1 ZANWTKIZLOFGNH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- LUIGQKZSUJUOBR-UHFFFAOYSA-N n,2,4-triphenyl-1,3-thiazol-5-amine Chemical compound C=1C=CC=CC=1NC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 LUIGQKZSUJUOBR-UHFFFAOYSA-N 0.000 claims description 3
- DTFQVYINYYFOBV-UHFFFAOYSA-N n-(2-chlorophenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound ClC1=CC=CC=C1NC1=C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)S1 DTFQVYINYYFOBV-UHFFFAOYSA-N 0.000 claims description 3
- GFXBUNWMYQFZAK-UHFFFAOYSA-N n-(3-fluorophenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound FC1=CC=CC(NC2=C(N=C(S2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GFXBUNWMYQFZAK-UHFFFAOYSA-N 0.000 claims description 3
- MTLNJFQBRIEAOQ-UHFFFAOYSA-N n-(4-chlorophenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)S1 MTLNJFQBRIEAOQ-UHFFFAOYSA-N 0.000 claims description 3
- AWGFMGDUMHZXTB-UHFFFAOYSA-N n-(4-fluorophenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)S1 AWGFMGDUMHZXTB-UHFFFAOYSA-N 0.000 claims description 3
- NSPVDFJJONSFKA-UHFFFAOYSA-N n-(4-methoxyphenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)S1 NSPVDFJJONSFKA-UHFFFAOYSA-N 0.000 claims description 3
- NVNRXCVZHXRXSV-UHFFFAOYSA-N n-(4-methylphenyl)-2,4-diphenyl-1,3-thiazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=C(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)S1 NVNRXCVZHXRXSV-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
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- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- VXGMOAIOIBICNL-UHFFFAOYSA-N 3-[[2-(4-aminoquinazolin-7-yl)-4-methyl-1,3-thiazol-5-yl]amino]cyclohexan-1-ol Chemical compound CC=1N=C(C=2C=C3N=CN=C(N)C3=CC=2)SC=1NC1CCCC(O)C1 VXGMOAIOIBICNL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- BKXGDIKYPROQQY-UHFFFAOYSA-N n-[4-[5-[(3-hydroxycyclohexyl)amino]-4-methyl-1,3-thiazol-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(S1)=NC(C)=C1NC1CC(O)CCC1 BKXGDIKYPROQQY-UHFFFAOYSA-N 0.000 claims description 2
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- 102000010984 Type 7 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract description 19
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 9
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Otolaryngology (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02290788A EP1348701A1 (en) | 2002-03-28 | 2002-03-28 | (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors |
| PCT/EP2003/002287 WO2003082839A1 (en) | 2002-03-28 | 2003-03-06 | (4,2-disubstituted-thiazol-5-yl)amine compounds as pde7 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005531526A true JP2005531526A (ja) | 2005-10-20 |
| JP2005531526A5 JP2005531526A5 (https=) | 2006-04-20 |
Family
ID=27798934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003580307A Withdrawn JP2005531526A (ja) | 2002-03-28 | 2003-03-06 | Ｐｄｅ７阻害剤としての（４，２−２置換−チアゾール−５−イル）アミン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6753340B2 (https=) |
| EP (2) | EP1348701A1 (https=) |
| JP (1) | JP2005531526A (https=) |
| AU (1) | AU2003212310A1 (https=) |
| BR (1) | BR0308765A (https=) |
| CA (1) | CA2480679A1 (https=) |
| MX (1) | MXPA04009476A (https=) |
| WO (1) | WO2003082839A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004044235A1 (en) * | 2002-11-13 | 2004-05-27 | Bayer Healthcare Ag | DIAGNOSTICS AND THERAPEUTICS FOR DISEASES ASSOCIATED WITH HUMAN PHOSPHODIESTERASE 7A1 (PDE7a1) |
| ES2217956B1 (es) * | 2003-01-23 | 2006-04-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| KR100783255B1 (ko) | 2004-02-13 | 2007-12-06 | 워너-램버트 캄파니 엘엘씨 | 안드로젠 수용체 조절제 |
| JP2007532621A (ja) | 2004-04-13 | 2007-11-15 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | アンドロゲンモジュレータ |
| WO2005102990A1 (en) | 2004-04-22 | 2005-11-03 | Warner-Lambert Company Llc | Androgen modulators |
| TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| WO2007056457A2 (en) | 2005-11-09 | 2007-05-18 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
| GB0701426D0 (en) * | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| WO2008119057A2 (en) * | 2007-03-27 | 2008-10-02 | Omeros Corporation | The use of pde7 inhibitors for the treatment of movement disorders |
| FR2943673B1 (fr) | 2009-03-27 | 2013-03-29 | Sanofi Aventis | Applications therapeutiques de derives de quinazolinedione |
| NZ628054A (en) | 2010-11-08 | 2016-03-31 | Omeros Corp | Treatment of addiction and impulse-control disorders using pde7 inhibitors |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| US20130184280A1 (en) * | 2011-12-21 | 2013-07-18 | Telik, Inc. | Substituted thiazoles as vegfr2 kinase inhibitors |
| KR102494647B1 (ko) | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| CN109689664B (zh) | 2016-07-14 | 2022-04-15 | 百时美施贵宝公司 | 作为par4抑制剂的三环杂芳基取代的喹啉和氮杂喹啉化合物 |
| US20190292176A1 (en) | 2016-07-14 | 2019-09-26 | Bistol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| US11987981B2 (en) | 2016-07-28 | 2024-05-21 | Carboshield, Inc. | Structural element reinforcement systems and methods |
| US12195987B2 (en) | 2016-07-28 | 2025-01-14 | Carboshield, Inc. | Structural element reinforcement systems and methods |
| IL318817A (en) | 2022-08-18 | 2025-04-01 | Mitodicure Gmbh | Use of a therapeutic agent with PHOSPHODIESTERASE-7 inhibitory activity for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exercise intolerance |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0772606A1 (en) * | 1994-07-27 | 1997-05-14 | G.D. SEARLE & CO. | Substituted thiazoles for the treatment of inflammation |
| WO1998008844A1 (de) * | 1996-08-26 | 1998-03-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Thiazol-derivate als selektive inhibitoren der pde-iv |
| US6313156B1 (en) * | 1999-12-23 | 2001-11-06 | Icos Corporation | Thiazole compounds as cyclic-AMP-specific phosphodiesterase inhibitors |
| AU2001237401B2 (en) * | 2000-03-01 | 2006-11-09 | Janssen Pharmaceutica N.V. | 2,4-disubstituted thiazolyl derivatives |
-
2002
- 2002-03-28 EP EP02290788A patent/EP1348701A1/en not_active Withdrawn
-
2003
- 2003-03-06 JP JP2003580307A patent/JP2005531526A/ja not_active Withdrawn
- 2003-03-06 EP EP03708184A patent/EP1492778A1/en not_active Withdrawn
- 2003-03-06 WO PCT/EP2003/002287 patent/WO2003082839A1/en not_active Ceased
- 2003-03-06 AU AU2003212310A patent/AU2003212310A1/en not_active Abandoned
- 2003-03-06 BR BR0308765-4A patent/BR0308765A/pt not_active IP Right Cessation
- 2003-03-06 CA CA002480679A patent/CA2480679A1/en not_active Abandoned
- 2003-03-06 MX MXPA04009476A patent/MXPA04009476A/es active IP Right Grant
- 2003-03-27 US US10/401,392 patent/US6753340B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6753340B2 (en) | 2004-06-22 |
| CA2480679A1 (en) | 2003-10-09 |
| EP1348701A1 (en) | 2003-10-01 |
| US20030191167A1 (en) | 2003-10-09 |
| AU2003212310A1 (en) | 2003-10-13 |
| WO2003082839A1 (en) | 2003-10-09 |
| BR0308765A (pt) | 2005-01-11 |
| MXPA04009476A (es) | 2005-01-25 |
| EP1492778A1 (en) | 2005-01-05 |
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