ZA200610138B - Factor Xa inhibitors - Google Patents
Factor Xa inhibitors Download PDFInfo
- Publication number
- ZA200610138B ZA200610138B ZA200610138A ZA200610138A ZA200610138B ZA 200610138 B ZA200610138 B ZA 200610138B ZA 200610138 A ZA200610138 A ZA 200610138A ZA 200610138 A ZA200610138 A ZA 200610138A ZA 200610138 B ZA200610138 B ZA 200610138B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloro
- methyl
- thiophene
- phenyl
- isoxazol
- Prior art date
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- 229940123583 Factor Xa inhibitor Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 103
- -1 S(O}R"TM Inorganic materials 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 150000003857 carboxamides Chemical class 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 208000007536 Thrombosis Diseases 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
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- 150000003839 salts Chemical class 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 3
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- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 90
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims 74
- 239000002253 acid Substances 0.000 claims 40
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 38
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 21
- VHINDKDACFDWPC-UHFFFAOYSA-N [O-]C(C1=CC=C[S+]1Cl)=O Chemical compound [O-]C(C1=CC=C[S+]1Cl)=O VHINDKDACFDWPC-UHFFFAOYSA-N 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 19
- BXEAAHIHFFIMIE-UHFFFAOYSA-N 3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Cl BXEAAHIHFFIMIE-UHFFFAOYSA-N 0.000 claims 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 16
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- 125000004076 pyridyl group Chemical group 0.000 claims 15
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- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
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- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 4
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- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
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- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 2
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- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- 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
- C07D333/26—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 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
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07D417/12—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 chain containing hetero atoms as chain links
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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
- C07D417/14—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 three or more hetero rings
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- Vascular Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| CN1968922A (zh) | 2004-06-18 | 2007-05-23 | 米伦纽姆医药公司 | 因子xa抑制剂 |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| AU2006244072B2 (en) | 2005-05-10 | 2012-09-20 | Intermune, Inc. | Pyridone derivatives for modulating stress-activated protein kinase system |
| WO2007007588A1 (ja) * | 2005-07-08 | 2007-01-18 | Ono Pharmaceutical Co., Ltd. | 平面性を有する環状基を母核とする化合物 |
| EP1998612A4 (en) | 2006-01-25 | 2010-11-24 | Synta Pharmaceuticals Corp | SUBSTITUTED BIARYL COMPOUNDS FOR USE AGAINST INFLAMMATION AND IMMUNE DISORDERS |
| CA2641766A1 (en) | 2006-02-15 | 2007-08-23 | Abbott Laboratories | Novel acetyl-coa carboxylase (acc) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| JP5369257B2 (ja) * | 2006-02-15 | 2013-12-18 | アッヴィ・インコーポレイテッド | 新規なアセチル−ＣｏＡカルボキシラーゼ（ＡＣＣ）阻害薬およびそれらの糖尿病、肥満および代謝症候群での使用 |
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| NZ572418A (en) * | 2006-05-05 | 2011-08-26 | Millennium Pharm Inc | Factor xa inhibitors |
| DE102006025314A1 (de) * | 2006-05-31 | 2007-12-06 | Bayer Healthcare Ag | Arylsubstituierte Heterozyklen und ihre Verwendung |
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| US20080293704A1 (en) * | 2007-01-05 | 2008-11-27 | Millennium Pharmaceuticals, Inc. | FACTOR Xa INHIBITORS |
| JP5469595B2 (ja) | 2007-04-13 | 2014-04-16 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | 第Ｘａ因子阻害薬として作用する化合物との併用抗凝固療法 |
| NZ599556A (en) * | 2007-05-02 | 2013-10-25 | Portola Pharm Inc | Combination therapy with a compound acting as a platelet adp receptor inhibitor |
| EP2520561B1 (en) | 2007-06-08 | 2016-02-10 | MannKind Corporation | IRE-1A Inhibitors |
| DE102007028407A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028406A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028319A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| US8168678B2 (en) | 2008-02-01 | 2012-05-01 | Panmira Pharmaceuticals, Inc. | N,N-disubstituted aminoalkylbiphenyl antagonists of prostaglandin D2 receptors |
| AR071069A1 (es) * | 2008-03-26 | 2010-05-26 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso para la prevencion o el tratamiento de cancer |
| CA2721452A1 (en) * | 2008-04-16 | 2009-10-22 | Biolipox Ab | Bis-aryl compounds for use as medicaments |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
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-
2005
- 2005-06-20 CN CNA2005800190908A patent/CN1968922A/zh active Pending
- 2005-06-20 JP JP2007516824A patent/JP5020073B2/ja not_active Expired - Fee Related
- 2005-06-20 US US11/158,274 patent/US7521470B2/en not_active Expired - Fee Related
- 2005-06-20 BR BRPI0512273-2A patent/BRPI0512273A/pt not_active Application Discontinuation
- 2005-06-20 CA CA002565437A patent/CA2565437A1/en not_active Abandoned
- 2005-06-20 NZ NZ552187A patent/NZ552187A/en not_active IP Right Cessation
- 2005-06-20 EP EP05762149.2A patent/EP1893572B1/en not_active Expired - Lifetime
- 2005-06-20 KR KR1020077001313A patent/KR101195801B1/ko not_active Expired - Fee Related
- 2005-06-20 WO PCT/US2005/021817 patent/WO2006002099A2/en not_active Ceased
- 2005-06-20 AU AU2005257999A patent/AU2005257999B2/en not_active Ceased
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2009
- 2009-01-05 US US12/348,879 patent/US8153670B2/en not_active Expired - Fee Related
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2011
- 2011-08-19 US US13/213,927 patent/US8377974B2/en not_active Expired - Fee Related
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| KR20070027714A (ko) | 2007-03-09 |
| WO2006002099A2 (en) | 2006-01-05 |
| AU2005257999B2 (en) | 2011-12-08 |
| MXPA06013960A (es) | 2007-03-15 |
| JP2008503497A (ja) | 2008-02-07 |
| US8153670B2 (en) | 2012-04-10 |
| EP1893572A2 (en) | 2008-03-05 |
| CA2565437A1 (en) | 2006-01-05 |
| US20060100193A1 (en) | 2006-05-11 |
| AU2005257999A1 (en) | 2006-01-05 |
| JP5020073B2 (ja) | 2012-09-05 |
| IL178807A0 (en) | 2007-03-08 |
| NZ552187A (en) | 2010-08-27 |
| US20090298806A1 (en) | 2009-12-03 |
| US8377974B2 (en) | 2013-02-19 |
| KR101195801B1 (ko) | 2012-11-05 |
| US20120178733A1 (en) | 2012-07-12 |
| EP1893572B1 (en) | 2016-12-14 |
| BRPI0512273A (pt) | 2008-02-19 |
| US7521470B2 (en) | 2009-04-21 |
| EP1893572A4 (en) | 2010-09-08 |
| CN1968922A (zh) | 2007-05-23 |
| WO2006002099A3 (en) | 2006-05-04 |
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