BRPI0619835A2 - compostos orgánicos - Google Patents
compostos orgánicos Download PDFInfo
- Publication number
- BRPI0619835A2 BRPI0619835A2 BRPI0619835-0A BRPI0619835A BRPI0619835A2 BR PI0619835 A2 BRPI0619835 A2 BR PI0619835A2 BR PI0619835 A BRPI0619835 A BR PI0619835A BR PI0619835 A2 BRPI0619835 A2 BR PI0619835A2
- Authority
- BR
- Brazil
- Prior art keywords
- methylthiazol
- ethyl
- ureido
- alkyl
- methyl
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 150000003839 salts Chemical group 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 230000002757 inflammatory effect Effects 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000023504 respiratory system disease Diseases 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000000414 obstructive effect Effects 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 229940080818 propionamide Drugs 0.000 claims 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- KCNPDWFYWXQCJW-UHFFFAOYSA-N 4-[2-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethylcarbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoic acid Chemical compound S1C(C=2C=CC(=CC=2)C(O)=O)=C(C)N=C1NC(=O)NCCC1=CN(CCF)C=N1 KCNPDWFYWXQCJW-UHFFFAOYSA-N 0.000 claims 1
- LNWFXNTXTWTRNE-UHFFFAOYSA-N 4-[2-[[3-(2,2-difluoroethylamino)-3-oxopropyl]carbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoic acid Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)F)SC(C=2C=CC(=CC=2)C(O)=O)=C1C LNWFXNTXTWTRNE-UHFFFAOYSA-N 0.000 claims 1
- UECFUHQWPPIZCW-UHFFFAOYSA-N 4-[4-methyl-2-[2-(1-propan-2-ylimidazol-4-yl)ethylcarbamoylamino]-1,3-thiazol-5-yl]benzoic acid Chemical compound CC(C)N1C=NC(CCNC(=O)NC=2SC(=C(C)N=2)C=2C=CC(=CC=2)C(O)=O)=C1 UECFUHQWPPIZCW-UHFFFAOYSA-N 0.000 claims 1
- CMCNQNFXWURBPI-UHFFFAOYSA-N CC1=CSC(=N1)NC(=O)NCCC(=O)NCC(F)F Chemical compound CC1=CSC(=N1)NC(=O)NCCC(=O)NCC(F)F CMCNQNFXWURBPI-UHFFFAOYSA-N 0.000 claims 1
- DSGSUZZCLFHSGV-UHFFFAOYSA-N N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C(=CC=CC=2)C(N)=O)=C1C Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C(=CC=CC=2)C(N)=O)=C1C DSGSUZZCLFHSGV-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- QXSZDKNSLIKNSC-UHFFFAOYSA-N methyl 4-[2-[2-[1-(2-fluoroethyl)imidazol-4-yl]ethylcarbamoylamino]-4-methyl-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(CCF)C=2)S1 QXSZDKNSLIKNSC-UHFFFAOYSA-N 0.000 claims 1
- CLMRTFRKPSDGLU-UHFFFAOYSA-N methyl 4-[4-methyl-2-[2-(1-propan-2-ylimidazol-4-yl)ethylcarbamoylamino]-1,3-thiazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)N=C(NC(=O)NCCC=2N=CN(C=2)C(C)C)S1 CLMRTFRKPSDGLU-UHFFFAOYSA-N 0.000 claims 1
- BCJZOLIKFRGVGG-UHFFFAOYSA-N n-cyclopropyl-4-[4-methyl-2-[[3-oxo-3-(2,2,2-trifluoroethylamino)propyl]carbamoylamino]-1,3-thiazol-5-yl]benzamide Chemical compound N1=C(NC(=O)NCCC(=O)NCC(F)(F)F)SC(C=2C=CC(=CC=2)C(=O)NC2CC2)=C1C BCJZOLIKFRGVGG-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 17
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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| Application Number | Priority Date | Filing Date | Title |
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| GB0525671.4 | 2005-12-16 | ||
| GBGB0525671.4A GB0525671D0 (en) | 2005-12-16 | 2005-12-16 | Organic compounds |
| PCT/EP2006/012018 WO2007068473A2 (en) | 2005-12-16 | 2006-12-13 | Organic compounds |
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| BRPI0619835A2 true BRPI0619835A2 (pt) | 2011-10-18 |
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| US (1) | US7754746B2 (enExample) |
| EP (2) | EP1966175A2 (enExample) |
| JP (1) | JP2009519280A (enExample) |
| KR (1) | KR20080068744A (enExample) |
| CN (1) | CN101374823A (enExample) |
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| AR038703A1 (es) * | 2002-02-28 | 2005-01-26 | Novartis Ag | Derivados de 5-feniltiazol y uso como inhibidor de quinasa p i 3 |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| GB0610243D0 (en) | 2006-05-23 | 2006-07-05 | Novartis Ag | Organic compounds |
| JP2011506560A (ja) | 2007-12-20 | 2011-03-03 | ノバルティス アーゲー | Ｐｉ３キナーゼ阻害剤として用いられるチアゾール誘導体 |
| CN102186822A (zh) | 2008-08-29 | 2011-09-14 | 顶标公司 | 新脲和硫脲衍生物 |
| UA104147C2 (uk) | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
| EA201200087A1 (ru) | 2009-07-02 | 2012-07-30 | Новартис Аг | 2-карбоксамиды циклоаминомочевин, которые являются ингибиторами pi3k |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
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| US5451700A (en) | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| PL203117B1 (pl) | 1999-05-04 | 2009-08-31 | Schering Corp | Piperydynopiperydynowa pochodna użyteczna jako antagonista CCR5, zawierająca ją kompozycja farmaceutyczna i jej zastosowanie |
| SK286641B6 (sk) | 1999-05-04 | 2009-03-05 | Schering Corporation | Piperazínové deriváty užitočné ako CCR5 antagonisty, farmaceutické prípravky s ich obsahom a ich použitie |
| AR038703A1 (es) * | 2002-02-28 | 2005-01-26 | Novartis Ag | Derivados de 5-feniltiazol y uso como inhibidor de quinasa p i 3 |
| GB0320197D0 (en) * | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
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2005
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Also Published As
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| JP2009519280A (ja) | 2009-05-14 |
| EP1966175A2 (en) | 2008-09-10 |
| CA2631051A1 (en) | 2007-06-21 |
| US7754746B2 (en) | 2010-07-13 |
| GB0525671D0 (en) | 2006-01-25 |
| WO2007068473A3 (en) | 2007-08-23 |
| CN101374823A (zh) | 2009-02-25 |
| RU2008128566A (ru) | 2010-01-27 |
| US20080319033A1 (en) | 2008-12-25 |
| EP2357179A1 (en) | 2011-08-17 |
| KR20080068744A (ko) | 2008-07-23 |
| AU2006326255A1 (en) | 2007-06-21 |
| WO2007068473A2 (en) | 2007-06-21 |
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