AU2003286145B2 - Carboxamides - Google Patents
Carboxamides Download PDFInfo
- Publication number
- AU2003286145B2 AU2003286145B2 AU2003286145A AU2003286145A AU2003286145B2 AU 2003286145 B2 AU2003286145 B2 AU 2003286145B2 AU 2003286145 A AU2003286145 A AU 2003286145A AU 2003286145 A AU2003286145 A AU 2003286145A AU 2003286145 B2 AU2003286145 B2 AU 2003286145B2
- Authority
- AU
- Australia
- 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.)
- Ceased
Links
- 150000003857 carboxamides Chemical class 0.000 title description 2
- -1 car bonyl oxygen Chemical compound 0.000 claims description 237
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 47
- 239000012453 solvate Substances 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 16
- 229940080818 propionamide Drugs 0.000 claims description 16
- 108010074860 Factor Xa Proteins 0.000 claims description 14
- 208000007536 Thrombosis Diseases 0.000 claims description 14
- 125000003118 aryl group Chemical group 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
- 239000002253 acid Substances 0.000 claims description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 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
- 208000006011 Stroke Diseases 0.000 claims description 7
- 238000002399 angioplasty Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 208000010125 myocardial infarction 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
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 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
- 208000037803 restenosis Diseases 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 229950001902 dimevamide Drugs 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 108010039209 Blood Coagulation Factors Proteins 0.000 claims description 3
- 102000015081 Blood Coagulation Factors Human genes 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000003114 blood coagulation factor Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 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
- 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
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- BPXCLLWXDHBFRH-UHFFFAOYSA-N 3-methoxypropanamide Chemical compound COCCC(N)=O BPXCLLWXDHBFRH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- ATSQOLIXZIECLF-UHFFFAOYSA-N 5-chloro-n-[3-[3-methyl-4-(2-oxopiperidin-1-yl)anilino]-3-oxopropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(CCCC2)=O)C(C)=CC=1NC(=O)CCNC(=O)C1=CC=C(Cl)S1 ATSQOLIXZIECLF-UHFFFAOYSA-N 0.000 claims 1
- 241000556679 Pholis Species 0.000 claims 1
- 208000024980 claudication Diseases 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000000132 electrospray ionisation Methods 0.000 description 95
- 235000013350 formula milk Nutrition 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 108090000190 Thrombin Proteins 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229960004072 thrombin Drugs 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000003146 anticoagulant agent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 108010048049 Factor IXa Proteins 0.000 description 5
- 239000012317 TBTU Substances 0.000 description 5
- 208000001435 Thromboembolism Diseases 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 230000002785 anti-thrombosis Effects 0.000 description 5
- 229940127219 anticoagulant drug Drugs 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000023555 blood coagulation Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- BVKWVMOTHUYVKL-UHFFFAOYSA-N 1-(4-amino-2-methylphenyl)piperidin-2-one Chemical compound CC1=CC(N)=CC=C1N1C(=O)CCCC1 BVKWVMOTHUYVKL-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000014508 negative regulation of coagulation Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UTYNKNJNZWFYRD-PFEQFJNWSA-N (2r)-2-amino-4-methyl-n-[4-(3-oxomorpholin-4-yl)phenyl]pentanamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1N1C(=O)COCC1 UTYNKNJNZWFYRD-PFEQFJNWSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 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 description 2
- 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 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 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
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
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- 239000011877 solvent mixture Substances 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- HYTQJXVSUVRUGL-MRXNPFEDSA-N tert-butyl (3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-4-oxobutanoate Chemical compound N([C@H](CC(=O)OC(C)(C)C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 HYTQJXVSUVRUGL-MRXNPFEDSA-N 0.000 description 1
- YHKKVXSPKWPJCC-MRXNPFEDSA-N tert-butyl (3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-oxo-4-[4-(3-oxomorpholin-4-yl)anilino]butanoate Chemical compound N([C@H](CC(=O)OC(C)(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 YHKKVXSPKWPJCC-MRXNPFEDSA-N 0.000 description 1
- WHCUHRITAMKXQB-QGZVFWFLSA-N tert-butyl (4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-5-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-5-oxopentanoate Chemical compound N([C@H](CCC(=O)OC(C)(C)C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 WHCUHRITAMKXQB-QGZVFWFLSA-N 0.000 description 1
- LECYJDLYRRFGCH-GOSISDBHSA-N tert-butyl (4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-5-oxo-5-[4-(2-oxopiperidin-1-yl)anilino]pentanoate Chemical compound N([C@H](CCC(=O)OC(C)(C)C)C(=O)NC=1C=CC(=CC=1)N1C(CCCC1)=O)C(=O)C1=CC=C(Cl)S1 LECYJDLYRRFGCH-GOSISDBHSA-N 0.000 description 1
- AQMCCKUFLFJASE-QGZVFWFLSA-N tert-butyl (4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-5-oxo-5-[4-(3-oxomorpholin-4-yl)anilino]pentanoate Chemical compound N([C@H](CCC(=O)OC(C)(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 AQMCCKUFLFJASE-QGZVFWFLSA-N 0.000 description 1
- SGFVHSXGHNHATC-UHFFFAOYSA-N tert-butyl 4-(4-aminophenyl)-3-oxopiperazine-1-carboxylate Chemical compound O=C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1 SGFVHSXGHNHATC-UHFFFAOYSA-N 0.000 description 1
- ILMYKMBFQWDQLG-MRXNPFEDSA-N tert-butyl 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](CNC(=O)OC(C)(C)C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 ILMYKMBFQWDQLG-MRXNPFEDSA-N 0.000 description 1
- BELSQADCWRBSRT-MRXNPFEDSA-N tert-butyl n-[(2r)-2-[(5-chlorothiophene-2-carbonyl)amino]-3-oxo-3-[4-(3-oxomorpholin-4-yl)anilino]propyl]carbamate Chemical compound N([C@H](CNC(=O)OC(C)(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 BELSQADCWRBSRT-MRXNPFEDSA-N 0.000 description 1
- MIVLRSWXELUEIQ-QGZVFWFLSA-N tert-butyl n-[(3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-4-oxobutyl]carbamate Chemical compound N([C@H](CCNC(=O)OC(C)(C)C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 MIVLRSWXELUEIQ-QGZVFWFLSA-N 0.000 description 1
- BLAZHCUMJHHGOG-QGZVFWFLSA-N tert-butyl n-[(3r)-3-[(5-chlorothiophene-2-carbonyl)amino]-4-oxo-4-[4-(3-oxomorpholin-4-yl)anilino]butyl]carbamate Chemical compound N([C@H](CCNC(=O)OC(C)(C)C)C(=O)NC=1C=CC(=CC=1)N1C(COCC1)=O)C(=O)C1=CC=C(Cl)S1 BLAZHCUMJHHGOG-QGZVFWFLSA-N 0.000 description 1
- DUAMBQYLICRRHR-GOSISDBHSA-N tert-butyl n-[(4r)-4-[(5-chlorothiophene-2-carbonyl)amino]-5-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]-5-oxopentyl]carbamate Chemical compound N([C@H](CCCNC(=O)OC(C)(C)C)C(=O)NC=1C=C(C(=CC=1)N1C(COCC1)=O)C)C(=O)C1=CC=C(Cl)S1 DUAMBQYLICRRHR-GOSISDBHSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 125000005500 uronium group Chemical group 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- 239000011782 vitamin Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- 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
- 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 |
|---|---|
| AU2003286145A1 AU2003286145A1 (en) | 2004-06-15 |
| AU2003286145B2 true AU2003286145B2 (en) | 2009-11-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003286145A Ceased AU2003286145B2 (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 |
| CA2506716C (en) | 2012-09-04 |
| 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 |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |