KR20070044404A - 씨알티에이치2 리간드로서 치환된 티아졸초산 - Google Patents
씨알티에이치2 리간드로서 치환된 티아졸초산 Download PDFInfo
- Publication number
- KR20070044404A KR20070044404A KR1020067027509A KR20067027509A KR20070044404A KR 20070044404 A KR20070044404 A KR 20070044404A KR 1020067027509 A KR1020067027509 A KR 1020067027509A KR 20067027509 A KR20067027509 A KR 20067027509A KR 20070044404 A KR20070044404 A KR 20070044404A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- alkyl
- hydrogen
- ring
- fluoro
- 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.)
- Withdrawn
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- 239000003446 ligand Substances 0.000 title description 7
- BYHXLDZDSZVDJH-UHFFFAOYSA-N acetic acid;1,3-thiazole Chemical group CC(O)=O.C1=CSC=N1 BYHXLDZDSZVDJH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
- 239000001257 hydrogen Substances 0.000 claims abstract description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 52
- -1 N-pyrrolidinyl Chemical group 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 26
- 201000010099 disease Diseases 0.000 claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims abstract description 22
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims abstract description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 208000006673 asthma Diseases 0.000 claims abstract description 9
- 230000000694 effects Effects 0.000 claims abstract description 9
- 206010039083 rhinitis Diseases 0.000 claims abstract description 9
- 208000028004 allergic respiratory disease Diseases 0.000 claims abstract description 7
- 230000000172 allergic effect Effects 0.000 claims abstract description 4
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims description 5
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims description 5
- 230000004044 response Effects 0.000 claims description 5
- QNEMKHXNYQDLAU-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=C(F)C=C1 QNEMKHXNYQDLAU-UHFFFAOYSA-N 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
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- 125000002541 furyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 201000000306 sarcoidosis Diseases 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- RAJBDMPVCAZUIO-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)-phenylmethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(F)C=C1 RAJBDMPVCAZUIO-UHFFFAOYSA-N 0.000 claims description 3
- VIVMXCOHKFWMFI-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-2-phenylethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(CC=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(F)C=C1 VIVMXCOHKFWMFI-UHFFFAOYSA-N 0.000 claims description 3
- PMKHRUSPKPZZRI-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(3,4-difluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=C(F)C(F)=C1 PMKHRUSPKPZZRI-UHFFFAOYSA-N 0.000 claims description 3
- VRLVQIAKWWEZRU-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(3-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=CC(F)=C1 VRLVQIAKWWEZRU-UHFFFAOYSA-N 0.000 claims description 3
- ZOTGQGLOXKIJDG-UHFFFAOYSA-N 2-[2-[bis(4-methoxyphenyl)methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)C1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 ZOTGQGLOXKIJDG-UHFFFAOYSA-N 0.000 claims description 3
- VZONOYMJTLNJGC-UHFFFAOYSA-N 2-[2-benzhydryl-4-(3,4-difluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C(F)=C1 VZONOYMJTLNJGC-UHFFFAOYSA-N 0.000 claims description 3
- PVJXZPBQSMAWDT-UHFFFAOYSA-N 2-[2-benzhydryl-4-(3-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=CC(F)=C1 PVJXZPBQSMAWDT-UHFFFAOYSA-N 0.000 claims description 3
- RQZPTTAHWVRWET-UHFFFAOYSA-N 2-[2-benzhydryl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C=C1 RQZPTTAHWVRWET-UHFFFAOYSA-N 0.000 claims description 3
- FONANTIGBWSYGE-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[(4-methoxyphenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)C1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 FONANTIGBWSYGE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- HIEUVNLETVQMHD-UHFFFAOYSA-N 2-[2-benzhydryl-4-(4-chlorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 HIEUVNLETVQMHD-UHFFFAOYSA-N 0.000 claims description 2
- RSXKKNQRSFGEQT-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(4-chlorophenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(Cl)C=C1 RSXKKNQRSFGEQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
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| GB0412198.4 | 2004-05-29 | ||
| GB0412198A GB0412198D0 (en) | 2004-05-29 | 2004-05-29 | Medicinal use of receptor ligands |
| GB0414194A GB0414194D0 (en) | 2004-06-24 | 2004-06-24 | Medicinal use of receptor ligands |
| GB0414194.1 | 2004-06-24 | ||
| GB0424016A GB0424016D0 (en) | 2004-10-29 | 2004-10-29 | Medicinal use of receptor ligands |
| GB0424016.4 | 2004-10-29 |
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| KR20070044404A true KR20070044404A (ko) | 2007-04-27 |
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| GB0427381D0 (en) * | 2004-12-14 | 2005-01-19 | Novartis Ag | Organic compounds |
| UY30892A1 (es) | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| US8067448B2 (en) | 2008-02-22 | 2011-11-29 | Radius Health, Inc. | Selective androgen receptor modulators |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| JP5535931B2 (ja) * | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
| MY161598A (en) * | 2009-01-30 | 2017-04-28 | Glaxosmithkline Llc | Crystalline n-{ (1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl} -5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride |
| PH12012501280A1 (en) | 2009-12-23 | 2013-02-04 | Ironwood Pharmaceuticals Inc | Crth2 modulators |
| MX338831B (es) | 2010-02-04 | 2016-05-03 | Radius Health Inc | Moduladores selectivos de receptores de androgenos. |
| SI2568806T1 (sl) | 2010-05-12 | 2016-09-30 | Radius Health, Inc. | Režimi zdravljenja |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| AU2011312490B2 (en) | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| CN104114169A (zh) | 2011-12-16 | 2014-10-22 | 阿托佩斯治疗有限公司 | 用于治疗嗜酸细胞性食管炎的crth2拮抗剂和质子泵抑制剂的组合物 |
| HRP20220619T1 (hr) | 2016-06-22 | 2023-02-03 | Ellipses Pharma Ltd | Postupci za liječenje ar+ raka dojke |
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| ATE364597T1 (de) * | 1997-07-10 | 2007-07-15 | Janssen Pharmaceutica Nv | Il-5 hemmende 6-azauracilderivate |
| EP1045846B1 (en) * | 1997-11-28 | 2003-05-02 | Lg Chemical Limited | Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof |
| EP0987265A1 (en) * | 1998-09-18 | 2000-03-22 | Janssen Pharmaceutica N.V. | Interleukin-5 inhibiting 6-azauracil derivatives |
| HRP20020096A2 (en) * | 1999-08-06 | 2005-10-31 | Janssen Pharmaceutica N.V. | Interleukin-5 inhibiting 6-azauracil derivatives |
| US7276526B2 (en) * | 2001-07-13 | 2007-10-02 | Bristol-Myers Squibb Pharma Company | Substituted thiazoles and oxazoles as corticotropin releasing hormone ligands |
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
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Also Published As
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| IL179693A0 (en) | 2007-05-15 |
| EP1758874A1 (en) | 2007-03-07 |
| NO20066049L (no) | 2007-02-27 |
| WO2005116001A1 (en) | 2005-12-08 |
| BRPI0511671A (pt) | 2008-01-02 |
| US20080119456A1 (en) | 2008-05-22 |
| CR8837A (es) | 2008-03-18 |
| EA200602288A1 (ru) | 2007-10-26 |
| MXPA06013924A (es) | 2007-07-18 |
| CA2568742A1 (en) | 2005-12-08 |
| AU2005247610A1 (en) | 2005-12-08 |
| JP2008503447A (ja) | 2008-02-07 |
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