CA2481026A1 - N-`4-(2-imino-pyrrolidin-1-yl)phenyl!-acetamide and corresponding piperidine derivatives as factor xa inhibitors for the treatment of thrombo-embolic diseases - Google Patents
N-`4-(2-imino-pyrrolidin-1-yl)phenyl!-acetamide and corresponding piperidine derivatives as factor xa inhibitors for the treatment of thrombo-embolic diseases Download PDFInfo
- Publication number
- CA2481026A1 CA2481026A1 CA002481026A CA2481026A CA2481026A1 CA 2481026 A1 CA2481026 A1 CA 2481026A1 CA 002481026 A CA002481026 A CA 002481026A CA 2481026 A CA2481026 A CA 2481026A CA 2481026 A1 CA2481026 A1 CA 2481026A1
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- CA
- Canada
- Prior art keywords
- phenyl
- solvates
- monosubstituted
- stereoisomers
- ratios
- 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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- 238000011282 treatment Methods 0.000 title claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 51
- 208000001435 Thromboembolism Diseases 0.000 title abstract 2
- 229940123583 Factor Xa inhibitor Drugs 0.000 title description 3
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- -1 1H-pyridin-1-yl Chemical group 0.000 claims description 164
- 239000000203 mixture Substances 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 208000007536 Thrombosis Diseases 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
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- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004305 biphenyl Substances 0.000 claims description 4
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- 206010027599 migraine Diseases 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- XCSMVHHZHIQPDK-UHFFFAOYSA-N 2-(1-aminoisoquinolin-7-yl)oxy-n-[4-(2-iminopiperidin-1-yl)-3-methylphenyl]-4-methylpentanamide Chemical compound C=1C=C2C=CN=C(N)C2=CC=1OC(CC(C)C)C(=O)NC(C=C1C)=CC=C1N1CCCCC1=N XCSMVHHZHIQPDK-UHFFFAOYSA-N 0.000 claims description 2
- DOCJGXAFOCYCNF-UHFFFAOYSA-N 2-(1-aminoisoquinolin-7-yl)oxy-n-[4-(2-iminopyrrolidin-1-yl)phenyl]-4-methylpentanamide Chemical compound C=1C=C2C=CN=C(N)C2=CC=1OC(CC(C)C)C(=O)NC(C=C1)=CC=C1N1CCCC1=N DOCJGXAFOCYCNF-UHFFFAOYSA-N 0.000 claims description 2
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- OTBSKDOQQLCWHV-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-2-(2-chlorophenyl)-n-[3-fluoro-4-(2-iminopyrrolidin-1-yl)phenyl]acetamide Chemical compound NCC1=CC=CC(NC(C(=O)NC=2C=C(F)C(N3C(CCC3)=N)=CC=2)C=2C(=CC=CC=2)Cl)=C1 OTBSKDOQQLCWHV-UHFFFAOYSA-N 0.000 claims description 2
- DLJWXLXKEPOZSS-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-2-(2-fluorophenyl)-n-[4-(2-iminopiperidin-1-yl)-3-methylphenyl]acetamide Chemical compound C=1C=C(N2C(CCCC2)=N)C(C)=CC=1NC(=O)C(C=1C(=CC=CC=1)F)NC1=CC=CC(CN)=C1 DLJWXLXKEPOZSS-UHFFFAOYSA-N 0.000 claims description 2
- GQCGUHLLZGYGRT-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-n-[3-chloro-4-(2-iminopyrrolidin-1-yl)phenyl]-2-(2-chlorophenyl)acetamide Chemical compound NCC1=CC=CC(NC(C(=O)NC=2C=C(Cl)C(N3C(CCC3)=N)=CC=2)C=2C(=CC=CC=2)Cl)=C1 GQCGUHLLZGYGRT-UHFFFAOYSA-N 0.000 claims description 2
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- JPLMEBHYKMLHGP-UHFFFAOYSA-N 2-(1-aminoisoquinolin-7-yl)oxy-n-[4-(2-iminopiperidin-1-yl)phenyl]-4-methylpentanamide Chemical compound C=1C=C2C=CN=C(N)C2=CC=1OC(CC(C)C)C(=O)NC(C=C1)=CC=C1N1CCCCC1=N JPLMEBHYKMLHGP-UHFFFAOYSA-N 0.000 claims 1
- SFTPOGLYIHENTF-UHFFFAOYSA-N 2-(1-aminoisoquinolin-7-yl)oxy-n-[4-(2-methoxyiminopiperidin-1-yl)phenyl]-4-methylpentanamide Chemical compound CON=C1CCCCN1C(C=C1)=CC=C1NC(=O)C(CC(C)C)OC1=CC=C(C=CN=C2N)C2=C1 SFTPOGLYIHENTF-UHFFFAOYSA-N 0.000 claims 1
- MGDAVKBTKRTHRG-UHFFFAOYSA-N 2-[(3-amino-1,2-benzoxazol-5-yl)amino]-n-[3-chloro-4-(2-iminopyrrolidin-1-yl)phenyl]-2-phenylacetamide Chemical compound C1=C2C(N)=NOC2=CC=C1NC(C=1C=CC=CC=1)C(=O)NC(C=C1Cl)=CC=C1N1CCCC1=N MGDAVKBTKRTHRG-UHFFFAOYSA-N 0.000 claims 1
- PSPNSQMQEAUTBF-UHFFFAOYSA-N 2-[(5-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]-n-[4-(2-imino-3-azabicyclo[2.2.2]octan-3-yl)-3-methylphenyl]-2-phenylacetamide Chemical compound C=1C=C(N2C(C3CCC2CC3)=N)C(C)=CC=1NC(=O)C(OC=1C=C2CCCC(N)C2=CC=1)C1=CC=CC=C1 PSPNSQMQEAUTBF-UHFFFAOYSA-N 0.000 claims 1
- TXIWTDFUWOFBDF-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-2-(2-fluorophenyl)-N-[4-(2-hydroxy-3-iminopiperidin-1-yl)-3-methylphenyl]acetamide Chemical compound NCC=1C=C(C=CC=1)NC(C(=O)NC1=CC(=C(C=C1)N1C(C(CCC1)=N)O)C)C1=C(C=CC=C1)F TXIWTDFUWOFBDF-UHFFFAOYSA-N 0.000 claims 1
- HQDUBMOVUMOWGI-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-2-(2-fluorophenyl)-n-[4-(2-iminopyrrolidin-1-yl)-3-methylphenyl]acetamide Chemical compound C=1C=C(N2C(CCC2)=N)C(C)=CC=1NC(=O)C(C=1C(=CC=CC=1)F)NC1=CC=CC(CN)=C1 HQDUBMOVUMOWGI-UHFFFAOYSA-N 0.000 claims 1
- RWNAOOKWAXJASG-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-N-[3-chloro-4-(2-hydroxy-3-iminopyrrolidin-1-yl)phenyl]-2-(2-fluorophenyl)acetamide Chemical compound NCC=1C=C(C=CC=1)NC(C(=O)NC1=CC(=C(C=C1)N1C(C(CC1)=N)O)Cl)C1=C(C=CC=C1)F RWNAOOKWAXJASG-UHFFFAOYSA-N 0.000 claims 1
- SZDAEQMONSTXAN-UHFFFAOYSA-N 2-[3-(aminomethyl)anilino]-n-[3-chloro-4-(2-iminopyrrolidin-1-yl)phenyl]-2-phenylacetamide Chemical compound NCC1=CC=CC(NC(C(=O)NC=2C=C(Cl)C(N3C(CCC3)=N)=CC=2)C=2C=CC=CC=2)=C1 SZDAEQMONSTXAN-UHFFFAOYSA-N 0.000 claims 1
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
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- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- LMSDRBQUIRGULI-XZVFQGBBSA-N tert-butyl n-[[3-[[(1s)-1-(2-chlorophenyl)-2-[3-methyl-4-[(2r)-5-methyl-2-sulfanyl-3,4-dihydro-2h-pyrrol-1-ium-1-yl]anilino]-2-oxoethyl]amino]phenyl]methyl]carbamate;iodide Chemical compound [I-].S[C@@H]1CCC(C)=[N+]1C(C(=C1)C)=CC=C1NC(=O)[C@H](C=1C(=CC=CC=1)Cl)NC1=CC=CC(CNC(=O)OC(C)(C)C)=C1 LMSDRBQUIRGULI-XZVFQGBBSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10214832.5 | 2002-04-04 | ||
| DE10214832A DE10214832A1 (de) | 2002-04-04 | 2002-04-04 | Phenylderivate 4 |
| PCT/EP2003/002349 WO2003084533A1 (de) | 2002-04-04 | 2003-03-07 | N-`4-(2-imino-pyrrolidin-1-yl)phenyl!-acetemid-und entsprechende piperidinderivate als faktor xa inhibitoren zur behandlung von thromboembolischen erkrankungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2481026A1 true CA2481026A1 (en) | 2003-10-16 |
Family
ID=28051091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002481026A Abandoned CA2481026A1 (en) | 2002-04-04 | 2003-03-07 | N-`4-(2-imino-pyrrolidin-1-yl)phenyl!-acetamide and corresponding piperidine derivatives as factor xa inhibitors for the treatment of thrombo-embolic diseases |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20050176760A1 (https=) |
| EP (1) | EP1490056B1 (https=) |
| JP (1) | JP2005528377A (https=) |
| AR (1) | AR039249A1 (https=) |
| AT (1) | ATE337779T1 (https=) |
| AU (1) | AU2003214102A1 (https=) |
| CA (1) | CA2481026A1 (https=) |
| DE (2) | DE10214832A1 (https=) |
| ES (1) | ES2271539T3 (https=) |
| WO (1) | WO2003084533A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1594505A4 (en) | 2003-02-11 | 2008-08-13 | Bristol Myers Squibb Co | PHENYLGLYCIN DERIVATIVES USEFUL AS SERINE PROTEASE INHIBITORS |
| WO2004072102A2 (en) | 2003-02-11 | 2004-08-26 | Bristol-Myers Squibb Company | Benzene acetamide compounds useful as serine protease inhibitors |
| EP1479680A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Azaindole derivatives as Factor Xa inhibitors |
| PE20061117A1 (es) | 2005-01-10 | 2006-10-13 | Bristol Myers Squibb Co | DERIVADOS DE FENILGLICINAMIDA COMO INHIBIDORES DEL FACTOR VIIa |
| CA2610354C (en) | 2005-05-31 | 2011-03-29 | Pfizer Inc. | Substituted aryloxy-n-bicyclomethyl acetamide compounds as vr1 antagonists |
| WO2007002313A2 (en) | 2005-06-24 | 2007-01-04 | Bristol-Myers Squibb Company | Phenylglycinamide and pyridylglycinamide derivatives useful as anticoagulants |
| US7625890B2 (en) | 2005-11-10 | 2009-12-01 | Smithkline Beecham Corp. | Substituted imidazo[4,5-c]pyridine compounds as Akt inhibitors |
| CN102633783A (zh) * | 2006-02-10 | 2012-08-15 | 转化技术制药公司 | 作为Aurora激酶抑制剂的苯并唑系衍生物、组合物和使用方法 |
| US8440662B2 (en) | 2010-10-31 | 2013-05-14 | Endo Pharmaceuticals, Inc. | Substituted quinazoline and pyrido-pyrimidine derivatives |
| WO2021138391A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Indazole compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540109B1 (fr) * | 1983-01-28 | 1985-08-30 | Logeais Labor Jacques | Imino-2 pyrrolidines, leur procede de preparation et leurs applications en therapeutique |
| JP2003500382A (ja) * | 1999-05-24 | 2003-01-07 | シーオーアール セラピューティクス インコーポレイテッド | Ｘａ因子の阻害剤 |
| AU5158100A (en) * | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| DE10027025A1 (de) * | 2000-05-31 | 2001-12-06 | Merck Patent Gmbh | Clycinamide |
| DE10102322A1 (de) * | 2001-01-19 | 2002-07-25 | Merck Patent Gmbh | Phenylderivate |
-
2002
- 2002-04-04 DE DE10214832A patent/DE10214832A1/de not_active Withdrawn
-
2003
- 2003-03-07 ES ES03709758T patent/ES2271539T3/es not_active Expired - Lifetime
- 2003-03-07 CA CA002481026A patent/CA2481026A1/en not_active Abandoned
- 2003-03-07 AU AU2003214102A patent/AU2003214102A1/en not_active Abandoned
- 2003-03-07 JP JP2003581773A patent/JP2005528377A/ja active Pending
- 2003-03-07 DE DE50304858T patent/DE50304858D1/de not_active Expired - Fee Related
- 2003-03-07 US US10/510,046 patent/US20050176760A1/en not_active Abandoned
- 2003-03-07 AT AT03709758T patent/ATE337779T1/de not_active IP Right Cessation
- 2003-03-07 WO PCT/EP2003/002349 patent/WO2003084533A1/de not_active Ceased
- 2003-03-07 EP EP03709758A patent/EP1490056B1/de not_active Expired - Lifetime
- 2003-04-04 AR ARP030101174A patent/AR039249A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20050176760A1 (en) | 2005-08-11 |
| AU2003214102A1 (en) | 2003-10-20 |
| DE10214832A1 (de) | 2003-10-16 |
| EP1490056B1 (de) | 2006-08-30 |
| ES2271539T3 (es) | 2007-04-16 |
| DE50304858D1 (de) | 2006-10-12 |
| JP2005528377A (ja) | 2005-09-22 |
| EP1490056A1 (de) | 2004-12-29 |
| ATE337779T1 (de) | 2006-09-15 |
| WO2003084533A1 (de) | 2003-10-16 |
| AR039249A1 (es) | 2005-02-16 |
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