CA2473169A1 - Compounds that inhibit factor xa activity - Google Patents
Compounds that inhibit factor xa activity Download PDFInfo
- Publication number
- CA2473169A1 CA2473169A1 CA002473169A CA2473169A CA2473169A1 CA 2473169 A1 CA2473169 A1 CA 2473169A1 CA 002473169 A CA002473169 A CA 002473169A CA 2473169 A CA2473169 A CA 2473169A CA 2473169 A1 CA2473169 A1 CA 2473169A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- formula
- phenyl
- heteroaryl
- heteroalkyl
- 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.)
- Abandoned
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- 238000009472 formulation Methods 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
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- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 108010014806 prothrombinase complex Proteins 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- BGOFCVIGEYGEOF-UHFFFAOYSA-N salicylaldehyde beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=CC=C1C=O BGOFCVIGEYGEOF-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10204072.9 | 2002-01-31 | ||
| DE10204072A DE10204072A1 (de) | 2002-01-31 | 2002-01-31 | Neue Verbindungen, die Faktor Xa-Aktivität inhibieren |
| DE10300049.6 | 2003-01-03 | ||
| DE10300049A DE10300049A1 (de) | 2003-01-03 | 2003-01-03 | Neue Verbindungen, die Faktor VIIa inhibieren |
| PCT/EP2003/001011 WO2003064440A1 (de) | 2002-01-31 | 2003-01-31 | Verbindungen, die faktor xa-aktivät inhibieren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2473169A1 true CA2473169A1 (en) | 2003-08-07 |
Family
ID=27664555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002473169A Abandoned CA2473169A1 (en) | 2002-01-31 | 2003-01-31 | Compounds that inhibit factor xa activity |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20050049283A1 (enExample) |
| EP (1) | EP1470143B1 (enExample) |
| JP (1) | JP2005525325A (enExample) |
| KR (1) | KR20040096541A (enExample) |
| CN (1) | CN1322001C (enExample) |
| AT (1) | ATE377017T1 (enExample) |
| BR (1) | BR0307266A (enExample) |
| CA (1) | CA2473169A1 (enExample) |
| DE (1) | DE50308492D1 (enExample) |
| MX (1) | MXPA04007461A (enExample) |
| NZ (1) | NZ534238A (enExample) |
| PL (1) | PL369772A1 (enExample) |
| WO (1) | WO2003064440A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1732531A2 (en) * | 2004-02-25 | 2006-12-20 | La Jolla Pharmaceutical Company | Amines and amides for the treatment of diseases |
| ES2365815T3 (es) * | 2005-12-14 | 2011-10-11 | Bristol-Myers Squibb Company | Análogos de arilpropionamida, arilacrilamida, arilpropinamida o arilmetilurea como inhibidores del factor xia. |
| EA014245B1 (ru) | 2005-12-14 | 2010-10-29 | Бристол-Маерс Сквибб Компани | Аналоги арилпропионамида, арилакриламида, арилпропинамида или арилметилмочевины в качестве ингибиторов фактора xia |
| US10590084B2 (en) | 2016-03-09 | 2020-03-17 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| AU2017292646A1 (en) | 2016-07-05 | 2019-02-07 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| MX2019003425A (es) | 2016-09-28 | 2019-08-16 | Blade Therapeutics Inc | Moduladores de calpainas y usos terapeuticos de los mismos. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2614893B1 (fr) * | 1987-05-04 | 1989-12-22 | Fournier Innovation Synergie | Nouveaux b-d-phenyl-thioxylosides, leur procede de preparation et leur application en therapeutique |
| EP0560568A3 (en) * | 1992-03-13 | 1994-06-29 | Takeda Chemical Industries Ltd | Hydroquinone derivatives and intermediates for production thereof |
| PT921116E (pt) * | 1997-12-04 | 2003-11-28 | Hoffmann La Roche | Derivados de n-(4-carbamimido-fenil)-glicinamida |
| WO1999041231A1 (en) * | 1998-02-17 | 1999-08-19 | Ono Pharmaceutical Co., Ltd. | Amidino derivatives and drugs containing the same as the active ingredient |
| ATE405580T1 (de) * | 1998-06-17 | 2008-09-15 | Organon Nv | Antithrombotische verbindungen |
| DE10041402A1 (de) * | 2000-08-23 | 2002-03-14 | Morphochem Ag | Neue Verbindungen, die Faktor Xa-Aktivität inhibieren |
| US7504417B2 (en) * | 2000-11-22 | 2009-03-17 | Astellas Pharma Inc. | Substituted benzene derivatives or salts thereof |
-
2003
- 2003-01-31 DE DE50308492T patent/DE50308492D1/de not_active Expired - Fee Related
- 2003-01-31 PL PL03369772A patent/PL369772A1/xx not_active Application Discontinuation
- 2003-01-31 CA CA002473169A patent/CA2473169A1/en not_active Abandoned
- 2003-01-31 EP EP03734605A patent/EP1470143B1/de not_active Expired - Lifetime
- 2003-01-31 US US10/501,932 patent/US20050049283A1/en not_active Abandoned
- 2003-01-31 KR KR10-2004-7011732A patent/KR20040096541A/ko not_active Withdrawn
- 2003-01-31 BR BR0307266-5A patent/BR0307266A/pt not_active IP Right Cessation
- 2003-01-31 JP JP2003564060A patent/JP2005525325A/ja active Pending
- 2003-01-31 NZ NZ534238A patent/NZ534238A/en unknown
- 2003-01-31 CN CNB038031558A patent/CN1322001C/zh not_active Expired - Fee Related
- 2003-01-31 MX MXPA04007461A patent/MXPA04007461A/es active IP Right Grant
- 2003-01-31 WO PCT/EP2003/001011 patent/WO2003064440A1/de not_active Ceased
- 2003-01-31 AT AT03734605T patent/ATE377017T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1470143B1 (de) | 2007-10-31 |
| KR20040096541A (ko) | 2004-11-16 |
| EP1470143A1 (de) | 2004-10-27 |
| MXPA04007461A (es) | 2005-07-13 |
| NZ534238A (en) | 2006-09-29 |
| CN1322001C (zh) | 2007-06-20 |
| US20050049283A1 (en) | 2005-03-03 |
| CN1625559A (zh) | 2005-06-08 |
| ATE377017T1 (de) | 2007-11-15 |
| DE50308492D1 (de) | 2007-12-13 |
| PL369772A1 (en) | 2005-05-02 |
| JP2005525325A (ja) | 2005-08-25 |
| WO2003064440A1 (de) | 2003-08-07 |
| BR0307266A (pt) | 2004-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |