ZA200605839B - Carboxamide derivatives - Google Patents
Carboxamide derivatives Download PDFInfo
- Publication number
- ZA200605839B ZA200605839B ZA200605839A ZA200605839A ZA200605839B ZA 200605839 B ZA200605839 B ZA 200605839B ZA 200605839 A ZA200605839 A ZA 200605839A ZA 200605839 A ZA200605839 A ZA 200605839A ZA 200605839 B ZA200605839 B ZA 200605839B
- Authority
- ZA
- South Africa
- Prior art keywords
- denotes
- chlorophenyl
- oxo
- mono
- urea
- Prior art date
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- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000012453 solvate Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- -1 2-oxopiperidin- 1-yl Chemical group 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 108010074860 Factor Xa Proteins 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 208000007536 Thrombosis Diseases 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 108010039209 Blood Coagulation Factors Proteins 0.000 claims description 4
- 102000015081 Blood Coagulation Factors Human genes 0.000 claims description 4
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 206010022562 Intermittent claudication Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000002399 angioplasty Methods 0.000 claims description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
- 239000003114 blood coagulation factor Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims 20
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 12
- 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
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- LSIRKEFJYUWPEZ-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-1-(2-chlorophenyl)-2-[4-(1-methylpiperidin-4-yl)piperidin-1-yl]-2-oxoethyl]urea Chemical compound C1CN(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 LSIRKEFJYUWPEZ-XMMPIXPASA-N 0.000 claims 1
- SZGLHPFQKIUWTC-VZYDHVRKSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-(4-morpholin-4-ylpiperidin-1-yl)-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(O)=CC=C1[C@H](C(=O)N1CCC(CC1)N1CCOCC1)NC(=O)NC1=CC=C(Cl)C=C1 SZGLHPFQKIUWTC-VZYDHVRKSA-N 0.000 claims 1
- RPRFBYDSXLAIOV-GJFSDDNBSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-[4-(1-methylpiperidin-4-yl)piperidin-1-yl]-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC(O)=CC=2)CC1 RPRFBYDSXLAIOV-GJFSDDNBSA-N 0.000 claims 1
- TULCFWHZWFLHOZ-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-oxo-2-(4-piperidin-4-ylpiperidin-1-yl)ethyl]urea;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1[C@H](C(=O)N1CCC(CC1)C1CCNCC1)NC(=O)NC1=CC=C(Cl)C=C1 TULCFWHZWFLHOZ-GNAFDRTKSA-N 0.000 claims 1
- BKJXQOQIIKSWTK-BOXHHOBZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-cyclohexylpiperazin-1-yl)-2-oxo-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCN(C2CCCCC2)CC1 BKJXQOQIIKSWTK-BOXHHOBZSA-N 0.000 claims 1
- LQFJLONKXKWECV-BDQAORGHSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-morpholin-4-ylpiperidin-1-yl)-2-oxo-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCC(N2CCOCC2)CC1 LQFJLONKXKWECV-BDQAORGHSA-N 0.000 claims 1
- IYDPDDWCGYCEME-PPLJNSMQSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-ethylpiperazin-1-yl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CC)CCN1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 IYDPDDWCGYCEME-PPLJNSMQSA-N 0.000 claims 1
- PJYOTIORUIARDI-HSZRJFAPSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 PJYOTIORUIARDI-HSZRJFAPSA-N 0.000 claims 1
- PBPLZRDAQWTZOP-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(N2CCCCC2)CC1 PBPLZRDAQWTZOP-GNAFDRTKSA-N 0.000 claims 1
- WQHPPKLBOZGFPB-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-piperidin-4-ylpiperidin-1-yl)ethyl]urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(C2CCNCC2)CC1 WQHPPKLBOZGFPB-GNAFDRTKSA-N 0.000 claims 1
- OXZYVOYHRPBXIM-JOCHJYFZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(C=2C=CN=CC=2)CC1 OXZYVOYHRPBXIM-JOCHJYFZSA-N 0.000 claims 1
- WFFIYSJZJQQVKX-BOXHHOBZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-2-(4-piperidin-4-ylpiperidin-1-yl)-1-thiophen-2-ylethyl]urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCC(C2CCNCC2)CC1 WFFIYSJZJQQVKX-BOXHHOBZSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- UOCPNFUESUCHGS-CFAMDJDKSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.ClC1=CC=C(C=C1)NC(=O)N[C@H]([C@@H](C)OC)C(=O)N1C(CN(CC1)C=1C=NC=CC1)C Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.ClC1=CC=C(C=C1)NC(=O)N[C@H]([C@@H](C)OC)C(=O)N1C(CN(CC1)C=1C=NC=CC1)C UOCPNFUESUCHGS-CFAMDJDKSA-N 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 description 8
- 108090000190 Thrombin Proteins 0.000 description 7
- 229960004072 thrombin Drugs 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 208000001435 Thromboembolism Diseases 0.000 description 4
- 230000002785 anti-thrombosis Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 108010048049 Factor IXa Proteins 0.000 description 2
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 2
- 102000009123 Fibrin Human genes 0.000 description 2
- 108010073385 Fibrin Proteins 0.000 description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 108010000499 Thromboplastin Proteins 0.000 description 2
- 102000002262 Thromboplastin Human genes 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- 229950003499 fibrin Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000014508 negative regulation of coagulation Effects 0.000 description 2
- PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-N 0.000 description 1
- 108010014173 Factor X Proteins 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 150000008430 aromatic amides Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 230000004784 molecular pathogenesis Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
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- 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
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- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Health & Medical Sciences (AREA)
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- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE10358539A DE10358539A1 (de) | 2003-12-15 | 2003-12-15 | Carbonsäureamidderivate |
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ZA200605839B true ZA200605839B (en) | 2007-10-31 |
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ZA200605839A ZA200605839B (en) | 2003-12-15 | 2006-07-14 | Carboxamide derivatives |
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US (1) | US7951804B2 (pt) |
EP (1) | EP1694643A1 (pt) |
JP (1) | JP4990627B2 (pt) |
KR (1) | KR20060123305A (pt) |
CN (1) | CN1890216A (pt) |
AR (1) | AR047850A1 (pt) |
AU (1) | AU2004296956B2 (pt) |
BR (1) | BRPI0417153A (pt) |
CA (1) | CA2549548A1 (pt) |
DE (1) | DE10358539A1 (pt) |
RU (1) | RU2006125380A (pt) |
WO (1) | WO2005056528A1 (pt) |
ZA (1) | ZA200605839B (pt) |
Families Citing this family (9)
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JP4769082B2 (ja) * | 2003-12-17 | 2011-09-07 | 武田薬品工業株式会社 | ウレア誘導体、その製造法及び用途 |
US7678913B2 (en) | 2004-12-07 | 2010-03-16 | Portola Pharmaceuticals, Inc. | Ureas as factor Xa inhibitors |
US7601844B2 (en) * | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
TWI433838B (zh) | 2008-06-25 | 2014-04-11 | 必治妥美雅史谷比公司 | 作為趨化因子受體活性調節劑之六氫吡啶衍生物 |
US8642622B2 (en) | 2010-06-16 | 2014-02-04 | Bristol-Myers Squibb Company | Piperidinyl compound as a modulator of chemokine receptor activity |
EP2646030A1 (en) | 2010-12-03 | 2013-10-09 | Allergan, Inc. | Pharmaceutical compositions comprising 3,4- dihydroisoquinolin-2(1 h)-yl-3-phenylurea derivatives having formyl peptide receptor like-1 (fprl-1) agonist or antagonist activity |
FR2985256B1 (fr) * | 2011-12-30 | 2016-03-04 | Pitty Marc Henry | Derives piperazinyles pour le traitement de cancers |
CN111372576A (zh) | 2017-11-17 | 2020-07-03 | 塞尔利克斯生物私人有限公司 | 用于治疗眼部病症的组合物和方法 |
WO2022221686A1 (en) * | 2021-04-15 | 2022-10-20 | Pardes Biosciences, Inc. | Inhibitors of cysteine proteases and methods of use thereof |
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JPH0655758B2 (ja) * | 1984-08-24 | 1994-07-27 | 味の素株式会社 | アミノ酸誘導体 |
US5346907A (en) * | 1988-04-05 | 1994-09-13 | Abbott Laboratories | Amino acid analog CCK antagonists |
US5721251A (en) * | 1993-12-10 | 1998-02-24 | Merck & Co., Inc. | Piperidine, pyrrolidine and hexahydro-1H-azepines promote release of growth hormone |
IL115420A0 (en) * | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
JPH09227523A (ja) * | 1996-02-26 | 1997-09-02 | Toubishi Yakuhin Kogyo Kk | セリンから誘導される抗cck活性化合物 |
US5847148A (en) * | 1997-04-10 | 1998-12-08 | Pharmacia & Upjohn Company | Thiadiazole derivatives useful for the treatment of diseases related to connective tissue degradation |
DE10063008A1 (de) * | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
AU2002322585A1 (en) * | 2001-07-20 | 2003-03-03 | Adipogenix, Inc. | Fat accumulation-modulating compounds |
EP1499607B1 (en) * | 2001-12-04 | 2005-12-07 | Actelion Pharmaceuticals Ltd. | 4-(piperidyl- and pyrrolidyl-alkyl-ureido)-quinolines as urotensin ii receptor antagonists |
AU2002359458A1 (en) * | 2001-12-12 | 2003-06-23 | Eli Lilly And Company | Alanyl-piperidine heterocyclic derivatives useful against cardiovascular diseases |
EP1499591A1 (de) * | 2002-04-27 | 2005-01-26 | MERCK PATENT GmbH | Carbonsäureamide als inhibitoren des koagulationsfaktors xa |
US7220862B2 (en) * | 2002-06-05 | 2007-05-22 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
DE10302500A1 (de) * | 2003-01-23 | 2004-07-29 | Merck Patent Gmbh | Carbonsäureamidderivate |
US6846836B2 (en) * | 2003-04-18 | 2005-01-25 | Bristol-Myers Squibb Company | N-substituted phenylurea inhibitors of mitochondrial F1F0 ATP hydrolase |
BRPI0414777A (pt) * | 2003-09-26 | 2006-11-21 | Actelion Pharmaceuticals Ltd | compostos, composições farmacêuticas, uso de um ou mais compostos, e, método de tratar um paciente que sofre de um distúrbio |
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2003
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- 2004-11-19 KR KR1020067011538A patent/KR20060123305A/ko not_active Application Discontinuation
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2006
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Also Published As
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JP2007513987A (ja) | 2007-05-31 |
BRPI0417153A (pt) | 2007-03-06 |
RU2006125380A (ru) | 2008-01-27 |
CN1890216A (zh) | 2007-01-03 |
JP4990627B2 (ja) | 2012-08-01 |
KR20060123305A (ko) | 2006-12-01 |
AR047850A1 (es) | 2006-03-01 |
DE10358539A1 (de) | 2005-07-07 |
AU2004296956A1 (en) | 2005-06-23 |
US7951804B2 (en) | 2011-05-31 |
EP1694643A1 (de) | 2006-08-30 |
US20070123509A1 (en) | 2007-05-31 |
CA2549548A1 (en) | 2005-06-23 |
WO2005056528A1 (de) | 2005-06-23 |
AU2004296956B2 (en) | 2010-11-11 |
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