US20040082798A1 - Novel amino dicarboxylic acid derivatives with pharmaceutical properties - Google Patents
Novel amino dicarboxylic acid derivatives with pharmaceutical properties Download PDFInfo
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- US20040082798A1 US20040082798A1 US10/469,817 US46981703A US2004082798A1 US 20040082798 A1 US20040082798 A1 US 20040082798A1 US 46981703 A US46981703 A US 46981703A US 2004082798 A1 US2004082798 A1 US 2004082798A1
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- -1 amino dicarboxylic acid derivatives Chemical class 0.000 title claims description 179
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000003814 drug Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 475
- 125000000217 alkyl group Chemical group 0.000 claims description 182
- 239000001257 hydrogen Substances 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 127
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 91
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000003545 alkoxy group Chemical group 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical group 0.000 claims description 66
- 229910052717 sulfur Inorganic materials 0.000 claims description 66
- 125000001188 haloalkyl group Chemical group 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 53
- 150000003254 radicals Chemical class 0.000 claims description 51
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
- 230000008569 process Effects 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
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- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
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- 230000001537 neural effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- 238000010647 peptide synthesis reaction Methods 0.000 description 1
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- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 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
- 238000006268 reductive amination reaction Methods 0.000 description 1
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- 208000037803 restenosis Diseases 0.000 description 1
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- 208000019116 sleep disease Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
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- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229940083618 sodium nitroprusside Drugs 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
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- 230000002537 thrombolytic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
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- 208000019553 vascular disease Diseases 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/581,261 US7705043B2 (en) | 2001-03-07 | 2006-10-10 | Substituted aminodicarboxylic acid derivatives having pharmaceutical properties |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10110750.1 | 2001-03-07 | ||
DE10110750A DE10110750A1 (de) | 2001-03-07 | 2001-03-07 | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
PCT/EP2002/001891 WO2002070510A2 (de) | 2001-03-07 | 2002-02-22 | Aminodicarbonsäurederivate mit pharmazeutischen eigenschaften |
Related Child Applications (1)
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US11/581,261 Continuation US7705043B2 (en) | 2001-03-07 | 2006-10-10 | Substituted aminodicarboxylic acid derivatives having pharmaceutical properties |
Publications (1)
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US20040082798A1 true US20040082798A1 (en) | 2004-04-29 |
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US10/469,817 Abandoned US20040082798A1 (en) | 2001-03-07 | 2002-02-22 | Novel amino dicarboxylic acid derivatives with pharmaceutical properties |
US11/581,261 Expired - Fee Related US7705043B2 (en) | 2001-03-07 | 2006-10-10 | Substituted aminodicarboxylic acid derivatives having pharmaceutical properties |
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Application Number | Title | Priority Date | Filing Date |
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US11/581,261 Expired - Fee Related US7705043B2 (en) | 2001-03-07 | 2006-10-10 | Substituted aminodicarboxylic acid derivatives having pharmaceutical properties |
Country Status (7)
Country | Link |
---|---|
US (2) | US20040082798A1 (ja) |
EP (1) | EP1368335A2 (ja) |
JP (1) | JP4535679B2 (ja) |
AU (1) | AU2002234645A1 (ja) |
CA (1) | CA2439756C (ja) |
DE (1) | DE10110750A1 (ja) |
WO (1) | WO2002070510A2 (ja) |
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US20050009870A1 (en) * | 2003-07-11 | 2005-01-13 | Sher Philip M. | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
US20050282820A1 (en) * | 2004-06-17 | 2005-12-22 | Wyeth | Processes for preparing gonadotropin releasing hormone receptor antagonists |
US20050288366A1 (en) * | 2001-03-01 | 2005-12-29 | Bayer Aktiengesellschaft | Novel aminodicarboxylic acid derivatives |
US20060111355A1 (en) * | 2004-11-23 | 2006-05-25 | Wyeth | Gonadotropin releasing hormone receptor antagonists |
US20060189619A1 (en) * | 2005-02-24 | 2006-08-24 | Wyeth | 3-({4-[2-(4-Tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl}methyl)pyrido[2,3-b]]pyrazi ne compounds |
US20060189618A1 (en) * | 2005-02-18 | 2006-08-24 | Wyeth | 4-Substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US20060189616A1 (en) * | 2005-02-18 | 2006-08-24 | Wyeth | 7-Substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US20060189617A1 (en) * | 2005-02-18 | 2006-08-24 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
US20060264631A1 (en) * | 2005-05-18 | 2006-11-23 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
US20060270848A1 (en) * | 2005-05-26 | 2006-11-30 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of gonadotropin releasing hormone receptor |
US20060281768A1 (en) * | 2005-06-10 | 2006-12-14 | Gaul Michael D | Thienopyrimidine and thienopyridine kinase modulators |
US20070135477A1 (en) * | 2003-07-03 | 2007-06-14 | Astex Therapeuctics, Limited | Benzimidazole derivatives and their use as protein kinases inhibitors |
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US20080071095A1 (en) * | 2004-06-24 | 2008-03-20 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette Transporters |
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US20080085886A1 (en) * | 2006-08-21 | 2008-04-10 | Genentech, Inc. | Aza-benzofuranyl compounds and methods of use |
US20080132495A1 (en) * | 2004-12-30 | 2008-06-05 | Astex Therapeutics Limited | Pyrazole Compounds that Modulate the Activity of Cdk, Gsk and Aurora Kinases |
US20090088463A1 (en) * | 2005-11-01 | 2009-04-02 | Benjamin Pelcman | Pyrazoles Useful in the Treatment of Inflammation |
US20090105272A1 (en) * | 2005-12-24 | 2009-04-23 | Grootenhuis Peter D J | Prodrugs of modulators of ABC transporters |
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US20090186918A1 (en) * | 2005-10-31 | 2009-07-23 | Benjamin Pelcman | Triazole Compounds as Lipoxygenase Inhibitors |
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US20090291993A1 (en) * | 2005-10-21 | 2009-11-26 | Stephan Bartel | Difluorophenol Derivatives and Their Use |
US20100029772A1 (en) * | 2005-10-21 | 2010-02-04 | Stephan Bartel | Dicarboxylic Acid Derivatives and their Use |
US7696210B2 (en) | 2004-06-17 | 2010-04-13 | Wyeth | Gonadotropin releasing hormone receptor antagonists |
US20100168240A1 (en) * | 2007-03-29 | 2010-07-01 | Bayer Schering Pharma Aktiengesellschaft | Substituted dibenzoic acid derivatives and use thereof |
US20100184739A1 (en) * | 2004-06-24 | 2010-07-22 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette Transporters |
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Publication number | Publication date |
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WO2002070510A2 (de) | 2002-09-12 |
EP1368335A2 (de) | 2003-12-10 |
CA2439756C (en) | 2011-01-11 |
US20070179139A1 (en) | 2007-08-02 |
JP2004529111A (ja) | 2004-09-24 |
DE10110750A1 (de) | 2002-09-12 |
AU2002234645A1 (en) | 2002-09-19 |
WO2002070510A3 (de) | 2003-01-30 |
US7705043B2 (en) | 2010-04-27 |
CA2439756A1 (en) | 2002-09-12 |
JP4535679B2 (ja) | 2010-09-01 |
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