CA2506716C - Carboxamides - Google Patents
Carboxamides Download PDFInfo
- Publication number
- CA2506716C CA2506716C CA2506716A CA2506716A CA2506716C CA 2506716 C CA2506716 C CA 2506716C CA 2506716 A CA2506716 A CA 2506716A CA 2506716 A CA2506716 A CA 2506716A CA 2506716 C CA2506716 C CA 2506716C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- amino
- carbonyl
- chlorothiophene
- denotes
- 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.)
- Expired - Fee Related
Links
- 150000003857 carboxamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- -1 car-bonyl oxygen Chemical compound 0.000 claims description 221
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 45
- 239000012453 solvate Substances 0.000 claims description 34
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 208000007536 Thrombosis Diseases 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000002619 bicyclic group Chemical group 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 11
- 229940080818 propionamide Drugs 0.000 claims description 11
- 208000006011 Stroke Diseases 0.000 claims description 9
- 238000002399 angioplasty Methods 0.000 claims description 9
- 208000010125 myocardial infarction Diseases 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims description 8
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 8
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 206010022562 Intermittent claudication Diseases 0.000 claims description 8
- 206010027476 Metastases Diseases 0.000 claims description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 208000037803 restenosis Diseases 0.000 claims description 8
- 101150047265 COR2 gene Proteins 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 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 7
- 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 7
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 7
- 229950001902 dimevamide Drugs 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 101000582254 Homo sapiens Nuclear receptor corepressor 2 Proteins 0.000 claims description 5
- 102100030569 Nuclear receptor corepressor 2 Human genes 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- GDMMORZEHVKOIY-QGZVFWFLSA-N 5-chloro-n-[(2r)-1-[4-(2-iminopiperidin-1-yl)anilino]-4-methyl-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(CCCC1)=N)C(=O)C1=CC=C(Cl)S1 GDMMORZEHVKOIY-QGZVFWFLSA-N 0.000 claims description 3
- DRHWYFJXRFFHKI-CYBMUJFWSA-N 5-chloro-n-[(2r)-3-hydroxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CO)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 DRHWYFJXRFFHKI-CYBMUJFWSA-N 0.000 claims description 3
- CAINJQZABOHLSW-MRXNPFEDSA-N 5-chloro-n-[(2r)-4-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 CAINJQZABOHLSW-MRXNPFEDSA-N 0.000 claims description 3
- GDMMORZEHVKOIY-KRWDZBQOSA-N 5-chloro-n-[(2s)-1-[4-(2-iminopiperidin-1-yl)anilino]-4-methyl-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(CCCC1)=N)C(=O)C1=CC=C(Cl)S1 GDMMORZEHVKOIY-KRWDZBQOSA-N 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- SUMGSCRWLUSOTL-BZSJEYESSA-N (4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-2-methyl-n'-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]hexanediamide Chemical compound C([C@@H](CC(C)C(N)=O)NC(=O)C=1SC(Cl)=CC=1)C(=O)NC(C=C1C)=CC=C1N1CCOCC1=O SUMGSCRWLUSOTL-BZSJEYESSA-N 0.000 claims description 2
- SUMGSCRWLUSOTL-WMCAAGNKSA-N (4s)-4-[(5-chlorothiophene-2-carbonyl)amino]-2-methyl-n'-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]hexanediamide Chemical compound C([C@H](CC(C)C(N)=O)NC(=O)C=1SC(Cl)=CC=1)C(=O)NC(C=C1C)=CC=C1N1CCOCC1=O SUMGSCRWLUSOTL-WMCAAGNKSA-N 0.000 claims description 2
- FZHWONJTFQAXSC-HXUWFJFHSA-N 4-chloro-n-[(2r)-4-methyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pentan-2-yl]benzamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)C=C1 FZHWONJTFQAXSC-HXUWFJFHSA-N 0.000 claims description 2
- JTQAWQBGBMOBTN-CQSZACIVSA-N 5-chloro-n-[(2r)-1-[3-chloro-4-(2-oxopyridin-1-yl)anilino]-3-methoxy-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(Cl)C(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 JTQAWQBGBMOBTN-CQSZACIVSA-N 0.000 claims description 2
- LGHXVHOWQGYNBV-SNVBAGLBSA-N 5-chloro-n-[(2r)-1-[3-chloro-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](C)C(=O)NC=1C=C(Cl)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 LGHXVHOWQGYNBV-SNVBAGLBSA-N 0.000 claims description 2
- JNRKPCGSGPAKRR-CYBMUJFWSA-N 5-chloro-n-[(2r)-1-[3-chloro-4-(3-oxomorpholin-4-yl)anilino]-3-methoxy-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(Cl)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 JNRKPCGSGPAKRR-CYBMUJFWSA-N 0.000 claims description 2
- CKGOUIGNYBNPCU-CQSZACIVSA-N 5-chloro-n-[(2r)-1-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCC)C(=O)NC=1C=C(F)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 CKGOUIGNYBNPCU-CQSZACIVSA-N 0.000 claims description 2
- OBUFHQNBOLWWGU-CYBMUJFWSA-N 5-chloro-n-[(2r)-1-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-3-methoxy-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(F)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 OBUFHQNBOLWWGU-CYBMUJFWSA-N 0.000 claims description 2
- XUHQMWXHPDBUST-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-4-methyl-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=C(F)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 XUHQMWXHPDBUST-OAHLLOKOSA-N 0.000 claims description 2
- KXJBNDZPWRDBCM-MRXNPFEDSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxo-3-propoxypropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COCCC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 KXJBNDZPWRDBCM-MRXNPFEDSA-N 0.000 claims description 2
- QQUUAWAFTCCWOQ-CQSZACIVSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 QQUUAWAFTCCWOQ-CQSZACIVSA-N 0.000 claims description 2
- HTTZTVKZMBRALN-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopent-4-en-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC=C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 HTTZTVKZMBRALN-OAHLLOKOSA-N 0.000 claims description 2
- PKKRAKIYWJQKPI-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopent-4-yn-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC#C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 PKKRAKIYWJQKPI-OAHLLOKOSA-N 0.000 claims description 2
- AXNTTXXIDSQHMK-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 AXNTTXXIDSQHMK-OAHLLOKOSA-N 0.000 claims description 2
- XFAZCCFEUBGDTE-GFCCVEGCSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](C)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 XFAZCCFEUBGDTE-GFCCVEGCSA-N 0.000 claims description 2
- CMKXZNJTRGNSBY-YFKXAPIDSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-3-methylsulfonyl-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](C(C)S(C)(=O)=O)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 CMKXZNJTRGNSBY-YFKXAPIDSA-N 0.000 claims description 2
- MTANAQKWBOTPFU-AWEZNQCLSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-3-methylsulfonyl-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](CS(C)(=O)=O)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 MTANAQKWBOTPFU-AWEZNQCLSA-N 0.000 claims description 2
- HHWUKZSPGPLDRD-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-4-methylsulfanyl-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCSC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 HHWUKZSPGPLDRD-OAHLLOKOSA-N 0.000 claims description 2
- MLNSGAWUUMWNBW-MRXNPFEDSA-N 5-chloro-n-[(2r)-3-(2-methoxyethoxy)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COCCOC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 MLNSGAWUUMWNBW-MRXNPFEDSA-N 0.000 claims description 2
- LHLUIQHWPRSJDS-OAHLLOKOSA-N 5-chloro-n-[(2r)-3-ethoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COCC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 LHLUIQHWPRSJDS-OAHLLOKOSA-N 0.000 claims description 2
- ZJKUSSXXGFPAIZ-CQSZACIVSA-N 5-chloro-n-[(2r)-3-methoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 ZJKUSSXXGFPAIZ-CQSZACIVSA-N 0.000 claims description 2
- BQSKEBNXQHTNNJ-OAHLLOKOSA-N 5-chloro-n-[(2r)-3-methoxy-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]propan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 BQSKEBNXQHTNNJ-OAHLLOKOSA-N 0.000 claims description 2
- GQGBCTDPYRSCIP-LJQANCHMSA-N 5-chloro-n-[(2r)-3-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](C(C)C)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 GQGBCTDPYRSCIP-LJQANCHMSA-N 0.000 claims description 2
- DKLNFHPMUBBQCO-LJQANCHMSA-N 5-chloro-n-[(2r)-3-methyl-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](C(C)C)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 DKLNFHPMUBBQCO-LJQANCHMSA-N 0.000 claims description 2
- XIZCIUBAJJKVPX-HNNXBMFYSA-N 5-chloro-n-[(2r)-3-methylsulfanyl-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]propan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](CSC)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 XIZCIUBAJJKVPX-HNNXBMFYSA-N 0.000 claims description 2
- VXUBAUZHVCVWCY-YFKXAPIDSA-N 5-chloro-n-[(2r)-3-methylsulfonyl-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](C(C)S(C)(=O)=O)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 VXUBAUZHVCVWCY-YFKXAPIDSA-N 0.000 claims description 2
- XPRJUCHOUKEQBY-HNNXBMFYSA-N 5-chloro-n-[(2r)-3-methylsulfonyl-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]propan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](CS(=O)(=O)C)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 XPRJUCHOUKEQBY-HNNXBMFYSA-N 0.000 claims description 2
- OYHSKMMZKNHQPJ-OAHLLOKOSA-N 5-chloro-n-[(2r)-4-methoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCOC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 OYHSKMMZKNHQPJ-OAHLLOKOSA-N 0.000 claims description 2
- HMIFPBWBFGURQV-MRXNPFEDSA-N 5-chloro-n-[(2r)-4-methyl-1-oxo-1-[4-(2-oxopyrazin-1-yl)anilino]pentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(C=NC=C1)=O)C(=O)C1=CC=C(Cl)S1 HMIFPBWBFGURQV-MRXNPFEDSA-N 0.000 claims description 2
- XPAHBZCRFFKYLP-QGZVFWFLSA-N 5-chloro-n-[(2r)-4-methyl-1-oxo-1-[4-(2-oxopyridin-1-yl)anilino]pentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(C=CC=C1)=O)C(=O)C1=CC=C(Cl)S1 XPAHBZCRFFKYLP-QGZVFWFLSA-N 0.000 claims description 2
- BHLQMDIMXARSSM-GOSISDBHSA-N 5-chloro-n-[(2r)-4-methyl-1-oxo-1-[[4-(2-oxopiperidin-1-yl)phenyl]methylamino]pentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NCC=1C=CC(=CC=1)N1C(CCCC1)=O)C(=O)C1=CC=C(Cl)S1 BHLQMDIMXARSSM-GOSISDBHSA-N 0.000 claims description 2
- BLBREQDRVBQTLU-QVKFZJNVSA-N 5-chloro-n-[(2r,3r)-3-(2-methoxyethoxy)-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H]([C@@H](C)OCCOC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 BLBREQDRVBQTLU-QVKFZJNVSA-N 0.000 claims description 2
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Classifications
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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
- C07D409/02—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
- 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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- 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
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- 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
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10254336.4 | 2002-11-21 | ||
| DE10254336A DE10254336A1 (de) | 2002-11-21 | 2002-11-21 | Carbonsäureamide |
| PCT/EP2003/012080 WO2004046138A1 (de) | 2002-11-21 | 2003-10-30 | Carbonsäureamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2506716A1 CA2506716A1 (en) | 2004-06-03 |
| CA2506716C true CA2506716C (en) | 2012-09-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2506716A Expired - Fee Related CA2506716C (en) | 2002-11-21 | 2003-10-30 | Carboxamides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7579346B2 (https=) |
| EP (1) | EP1562939B1 (https=) |
| JP (1) | JP4732757B2 (https=) |
| AR (1) | AR042115A1 (https=) |
| AT (1) | ATE421515T1 (https=) |
| AU (1) | AU2003286145B2 (https=) |
| CA (1) | CA2506716C (https=) |
| DE (2) | DE10254336A1 (https=) |
| ES (1) | ES2320876T3 (https=) |
| WO (1) | WO2004046138A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1571154A1 (en) * | 2004-03-03 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Beta-aminoacid-derivatives as factor Xa inhibitors |
| CA2565186A1 (en) * | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Substituted thiophen-carboxylic acid amides, the production and the use thereof in the form of a drug |
| KR20070012552A (ko) | 2004-05-13 | 2007-01-25 | 베링거 인겔하임 인터내셔날 게엠베하 | 신규한 치환된 티오펜카복스아미드, 이의 제조방법 및약제로서의 이의 용도 |
| WO2005111013A1 (de) * | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Substituierte thiophen-2-carbonsäureamide, deren herstellung und deren verwendung als arzneimittel |
| DE102004047840A1 (de) | 2004-09-29 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Thiophencarbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel |
| CN101094835B (zh) * | 2004-11-03 | 2011-07-27 | 弗·哈夫曼-拉罗切有限公司 | 二酰胺衍生物 |
| EP1724269A1 (en) * | 2005-05-20 | 2006-11-22 | Sanofi-Aventis Deutschland GmbH | Heteroaryl-carboxylic acid (sulfamoyl alkyl) amide - derivatives as factor Xa inhibitors |
| PE20070171A1 (es) * | 2005-06-30 | 2007-03-08 | Boehringer Ingelheim Int | GLICINAMIDAS SUSTITUIDAS CON EFECTO ANTITROMBOTICO E INHIBIDOR DEL FACTOR Xa |
| AR057976A1 (es) * | 2005-08-29 | 2008-01-09 | Boehringer Ingelheim Int | Biarilos sustituidos y su uso como medicamentos. |
| AU2010362639B2 (en) * | 2010-10-18 | 2016-10-27 | Apotex Pharmachem Inc. | Processes for the preparation of Rivaroxaban and intermediates thereof |
| WO2013031930A1 (ja) * | 2011-08-31 | 2013-03-07 | 味の素株式会社 | イミン誘導体 |
| CN105294669B (zh) * | 2014-10-24 | 2019-01-22 | 山东凯森制药有限公司 | 一种第十因子抑制剂及其制备方法和应用 |
| BR112021010453A2 (pt) * | 2018-12-19 | 2021-08-24 | Leo Pharma A/S | Composto, e, composição farmacêutica |
| EP4015501A1 (en) * | 2020-12-16 | 2022-06-22 | Consejo Superior de Investigaciones Científicas (CSIC) | N-benzyl-alpha-aminoamides as anaphase-promoting complex/cyclosome (apc/c) inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2123246C2 (de) * | 1971-05-11 | 1982-11-25 | Basf Ag, 6700 Ludwigshafen | 6-[p-(β-Phenyläthylaminoacetylamino)-phenyl]-4,5-dihydropyridazon-(3) |
| ES2186811T3 (es) * | 1995-12-29 | 2003-05-16 | Boehringer Ingelheim Pharma | Derivados de feniltiazol con propiedades anti-virus herpes. |
| WO2000029399A1 (en) * | 1998-11-12 | 2000-05-25 | Boehringer Ingelheim (Canada) Ltd. | Antiherpes compounds |
| EP1185509A2 (en) * | 1999-05-24 | 2002-03-13 | Cor Therapeutics, Inc. | INHIBITORS OF FACTOR Xa |
| US6906063B2 (en) * | 2000-02-04 | 2005-06-14 | Portola Pharmaceuticals, Inc. | Platelet ADP receptor inhibitors |
| DE10010425A1 (de) * | 2000-03-03 | 2001-09-06 | Bayer Ag | Substituierte 5-Methyldihydropyridazinone und ihre Verwendung |
| DE60140748D1 (de) * | 2000-06-30 | 2010-01-21 | Dainippon Sumitomo Pharma Co | Thiazol-derivate zur verwendung als entzündungshemmende mittel |
| DE10035144A1 (de) | 2000-07-19 | 2002-01-31 | Merck Patent Gmbh | Cyclische Aminosäurederivate |
| DE10063008A1 (de) * | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| DE10102322A1 (de) * | 2001-01-19 | 2002-07-25 | Merck Patent Gmbh | Phenylderivate |
-
2002
- 2002-11-21 DE DE10254336A patent/DE10254336A1/de not_active Withdrawn
-
2003
- 2003-10-30 AU AU2003286145A patent/AU2003286145B2/en not_active Ceased
- 2003-10-30 AT AT03776875T patent/ATE421515T1/de not_active IP Right Cessation
- 2003-10-30 WO PCT/EP2003/012080 patent/WO2004046138A1/de not_active Ceased
- 2003-10-30 DE DE50311133T patent/DE50311133D1/de not_active Expired - Lifetime
- 2003-10-30 CA CA2506716A patent/CA2506716C/en not_active Expired - Fee Related
- 2003-10-30 JP JP2004552505A patent/JP4732757B2/ja not_active Expired - Fee Related
- 2003-10-30 US US10/535,246 patent/US7579346B2/en not_active Expired - Fee Related
- 2003-10-30 EP EP03776875A patent/EP1562939B1/de not_active Expired - Lifetime
- 2003-10-30 ES ES03776875T patent/ES2320876T3/es not_active Expired - Lifetime
- 2003-11-21 AR ARP030104308A patent/AR042115A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2506716A1 (en) | 2004-06-03 |
| EP1562939B1 (de) | 2009-01-21 |
| ES2320876T3 (es) | 2009-05-29 |
| AR042115A1 (es) | 2005-06-08 |
| JP4732757B2 (ja) | 2011-07-27 |
| AU2003286145B2 (en) | 2009-11-12 |
| WO2004046138A1 (de) | 2004-06-03 |
| US20060052376A1 (en) | 2006-03-09 |
| US7579346B2 (en) | 2009-08-25 |
| DE10254336A1 (de) | 2004-06-03 |
| JP2006512321A (ja) | 2006-04-13 |
| ATE421515T1 (de) | 2009-02-15 |
| AU2003286145A1 (en) | 2004-06-15 |
| DE50311133D1 (en) | 2009-03-12 |
| EP1562939A1 (de) | 2005-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20141030 |