JP2006512321A5 - - Google Patents
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- JP2006512321A5 JP2006512321A5 JP2004552505A JP2004552505A JP2006512321A5 JP 2006512321 A5 JP2006512321 A5 JP 2006512321A5 JP 2004552505 A JP2004552505 A JP 2004552505A JP 2004552505 A JP2004552505 A JP 2004552505A JP 2006512321 A5 JP2006512321 A5 JP 2006512321A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- amino
- carbonyl
- chlorothiophen
- oxomorpholin
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000012453 solvate Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 25
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 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 2
- 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 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010022562 Intermittent claudication Diseases 0.000 claims description 2
- 206010027476 Metastases Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- -1 pyridin-1-yl Chemical group 0.000 claims 73
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229920006395 saturated elastomer Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 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 3
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- IDMKVBMJPCIGGI-CYBMUJFWSA-N (2r)-2-[(5-chlorothiophene-2-carbonyl)amino]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]butanediamide Chemical compound N([C@H](CC(N)=O)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 IDMKVBMJPCIGGI-CYBMUJFWSA-N 0.000 claims 1
- FIKZIDFHDHGOTD-CYBMUJFWSA-N (3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-4-oxobutanoic acid Chemical compound N([C@H](CC(O)=O)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 FIKZIDFHDHGOTD-CYBMUJFWSA-N 0.000 claims 1
- NOCNGPMQRGBPMA-CYBMUJFWSA-N (3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-oxo-4-[4-(3-oxomorpholin-4-yl)anilino]butanoic acid Chemical compound N([C@H](CC(=O)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 NOCNGPMQRGBPMA-CYBMUJFWSA-N 0.000 claims 1
- SOYQZYRNPSWSNF-CQSZACIVSA-N (4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-5-oxo-5-[4-(3-oxomorpholin-4-yl)anilino]pentanoic acid Chemical compound N([C@H](CCC(=O)O)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 SOYQZYRNPSWSNF-CQSZACIVSA-N 0.000 claims 1
- 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 1
- DKUDMSKWQQJCRX-HXUWFJFHSA-N 4-chloro-n-[(2r)-4-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopentan-2-yl]benzamide 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)C=C1 DKUDMSKWQQJCRX-HXUWFJFHSA-N 0.000 claims 1
- 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 1
- QSQQHUWNCJCJAW-MRXNPFEDSA-N 5-bromo-n-[(2r)-4-methyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Br)S1 QSQQHUWNCJCJAW-MRXNPFEDSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NIXGDKRSIVLLGS-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pent-4-en-2-yl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)N[C@H](CC=C)C(=O)NC1=CC=C(N2C(COCC2)=O)C=C1 NIXGDKRSIVLLGS-OAHLLOKOSA-N 0.000 claims 1
- OKTMLDSEKPMWRC-OAHLLOKOSA-N 5-chloro-n-[(2r)-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pent-4-yn-2-yl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)N[C@H](CC#C)C(=O)NC1=CC=C(N2C(COCC2)=O)C=C1 OKTMLDSEKPMWRC-OAHLLOKOSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- WYDILNKRHWKIGY-CYBMUJFWSA-N 5-chloro-n-[(2r)-3-methoxy-1-oxo-1-[4-(3-oxomorpholin-4-yl)-3-(trifluoromethyl)anilino]propan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(C(N2C(COCC2)=O)=CC=1)C(F)(F)F)C(=O)C1=CC=C(Cl)S1 WYDILNKRHWKIGY-CYBMUJFWSA-N 0.000 claims 1
- 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 1
- 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 1
- MPCXIDUKWGATTR-GOSISDBHSA-N 5-chloro-n-[(2r)-3-methyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](C(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 MPCXIDUKWGATTR-GOSISDBHSA-N 0.000 claims 1
- 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 1
- XGMUVJSGPWKUHE-AWEZNQCLSA-N 5-chloro-n-[(2r)-3-methylsulfanyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]propan-2-yl]thiophene-2-carboxamide Chemical compound N([C@@H](CSC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 XGMUVJSGPWKUHE-AWEZNQCLSA-N 0.000 claims 1
- 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 1
- 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 1
- WZMDFROINKZZDM-ZJFPTPTDSA-N 5-chloro-n-[(2r)-3-methylsulfonyl-1-oxo-1-[4-(3-oxomorpholin-4-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(COCC1)=O)C(=O)C1=CC=C(Cl)S1 WZMDFROINKZZDM-ZJFPTPTDSA-N 0.000 claims 1
- MFCGDIFEVXITMZ-AWEZNQCLSA-N 5-chloro-n-[(2r)-3-methylsulfonyl-1-oxo-1-[4-(3-oxomorpholin-4-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(COCC1)=O)C(=O)C1=CC=C(Cl)S1 MFCGDIFEVXITMZ-AWEZNQCLSA-N 0.000 claims 1
- 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 1
- HBVUJUBSFKTDLO-OAHLLOKOSA-N 5-chloro-n-[(2r)-4-methoxy-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCOC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 HBVUJUBSFKTDLO-OAHLLOKOSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ZVBDDGSZXMMTTJ-MRXNPFEDSA-N 5-chloro-n-[(2r)-4-methyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pentan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CC(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 ZVBDDGSZXMMTTJ-MRXNPFEDSA-N 0.000 claims 1
- 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 1
- JIZMOCZTKHMOKI-OAHLLOKOSA-N 5-chloro-n-[(2r)-4-methylsulfanyl-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H](CCSC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 JIZMOCZTKHMOKI-OAHLLOKOSA-N 0.000 claims 1
- DBQXZSXTLSMNFD-JLTOFOAXSA-N 5-chloro-n-[(2r,3r)-3-ethoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H]([C@@H](C)OCC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 DBQXZSXTLSMNFD-JLTOFOAXSA-N 0.000 claims 1
- XTQGVEWJTAITAN-PIGZYNQJSA-N 5-chloro-n-[(2r,3r)-3-hydroxy-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H]([C@H](O)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 XTQGVEWJTAITAN-PIGZYNQJSA-N 0.000 claims 1
- JZWBQVCEEFWCJQ-BFUOFWGJSA-N 5-chloro-n-[(2r,3r)-3-methoxy-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H]([C@@H](C)OC)C(=O)NC=1C=C(C)C(N2C(COCC2)=O)=CC=1)C(=O)C1=CC=C(Cl)S1 JZWBQVCEEFWCJQ-BFUOFWGJSA-N 0.000 claims 1
- MJFLMMDDDAZVAI-KZULUSFZSA-N 5-chloro-n-[(2r,3r)-3-methoxy-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]thiophene-2-carboxamide Chemical compound N([C@H]([C@@H](C)OC)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 MJFLMMDDDAZVAI-KZULUSFZSA-N 0.000 claims 1
- ZJKUSSXXGFPAIZ-AWEZNQCLSA-N 5-chloro-n-[(2s)-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-AWEZNQCLSA-N 0.000 claims 1
- CAINJQZABOHLSW-INIZCTEOSA-N 5-chloro-n-[(2s)-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-INIZCTEOSA-N 0.000 claims 1
- HMIFPBWBFGURQV-INIZCTEOSA-N 5-chloro-n-[(2s)-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-INIZCTEOSA-N 0.000 claims 1
- BHLQMDIMXARSSM-SFHVURJKSA-N 5-chloro-n-[(2s)-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-SFHVURJKSA-N 0.000 claims 1
- PWIFLKGPDFKOAW-UKRRQHHQSA-N CC1=C(C=CC(=C1)NC[C@H]([C@@H](C)OC(=O)N)NC(=O)C2=CC=C(S2)Cl)N3CCOCC3=O Chemical compound CC1=C(C=CC(=C1)NC[C@H]([C@@H](C)OC(=O)N)NC(=O)C2=CC=C(S2)Cl)N3CCOCC3=O PWIFLKGPDFKOAW-UKRRQHHQSA-N 0.000 claims 1
- 108010054265 Factor VIIa Proteins 0.000 claims 1
- 108010074860 Factor Xa Proteins 0.000 claims 1
- RQXKBLSJCYBBFL-CYBMUJFWSA-N [(2r)-2-[(5-chlorothiophene-2-carbonyl)amino]-3-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-3-oxopropyl] carbamate Chemical compound N([C@H](COC(N)=O)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 RQXKBLSJCYBBFL-CYBMUJFWSA-N 0.000 claims 1
- PXFRKSPOZUZESB-PIGZYNQJSA-N [(2r,3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-oxo-4-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl] carbamate Chemical compound N([C@H]([C@H](OC(N)=O)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 PXFRKSPOZUZESB-PIGZYNQJSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 229950001902 dimevamide Drugs 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- UVBPFAROJLIVMV-AVVWSFFYSA-N n-[(2r)-1-[4-(3-azabicyclo[2.2.2]octan-3-yl)-3-(trifluoromethoxy)anilino]-3-methoxy-1-oxopropan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(OC(F)(F)F)C(N2C3CCC(CC3)C2)=CC=1)C(=O)C1=CC=C(Cl)S1 UVBPFAROJLIVMV-AVVWSFFYSA-N 0.000 claims 1
- ZEQCWHKBOMQPQY-PUJMQQBBSA-N n-[(2r)-1-[4-(3-azabicyclo[2.2.2]octan-3-yl)-3-chloroanilino]-3-methoxy-1-oxopropan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](COC)C(=O)NC=1C=C(Cl)C(N2C3CCC(CC3)C2)=CC=1)C(=O)C1=CC=C(Cl)S1 ZEQCWHKBOMQPQY-PUJMQQBBSA-N 0.000 claims 1
- CFQLEXVVTULQDP-CYBMUJFWSA-N n-[(2r)-3-amino-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopropan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CN)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 CFQLEXVVTULQDP-CYBMUJFWSA-N 0.000 claims 1
- SJIUIHNNCFTSPL-CYBMUJFWSA-N n-[(2r)-3-amino-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]propan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CN)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 SJIUIHNNCFTSPL-CYBMUJFWSA-N 0.000 claims 1
- QAYRGSJFWLREQS-CQSZACIVSA-N n-[(2r)-4-amino-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxobutan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CCN)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 QAYRGSJFWLREQS-CQSZACIVSA-N 0.000 claims 1
- IWAIRAQZYQZNBR-CQSZACIVSA-N n-[(2r)-4-amino-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]butan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CCN)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 IWAIRAQZYQZNBR-CQSZACIVSA-N 0.000 claims 1
- SOOKGTDDMKWBDA-OAHLLOKOSA-N n-[(2r)-5-amino-1-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-1-oxopentan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CCCN)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 SOOKGTDDMKWBDA-OAHLLOKOSA-N 0.000 claims 1
- XDQRFXGVNQAMFI-OAHLLOKOSA-N n-[(2r)-5-amino-1-oxo-1-[4-(3-oxomorpholin-4-yl)anilino]pentan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CCCN)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 XDQRFXGVNQAMFI-OAHLLOKOSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
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| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2006512321A JP2006512321A (ja) | 2006-04-13 |
| JP2006512321A5 true JP2006512321A5 (https=) | 2006-12-14 |
| JP4732757B2 JP4732757B2 (ja) | 2011-07-27 |
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| JP2004552505A Expired - Fee Related JP4732757B2 (ja) | 2002-11-21 | 2003-10-30 | カルボキサミド |
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| Country | Link |
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| 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=) |
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| 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
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