JP2008530240A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008530240A5 JP2008530240A5 JP2007556341A JP2007556341A JP2008530240A5 JP 2008530240 A5 JP2008530240 A5 JP 2008530240A5 JP 2007556341 A JP2007556341 A JP 2007556341A JP 2007556341 A JP2007556341 A JP 2007556341A JP 2008530240 A5 JP2008530240 A5 JP 2008530240A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- substituted
- methoxy
- isoxazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 2,3-dihydro-benzo [1,4] dioxinyl Chemical group 0.000 claims 122
- 125000001072 heteroaryl group Chemical group 0.000 claims 68
- 125000000623 heterocyclic group Chemical group 0.000 claims 55
- 125000003107 substituted aryl group Chemical group 0.000 claims 51
- 125000003710 aryl alkyl group Chemical group 0.000 claims 47
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 45
- 125000000547 substituted alkyl group Chemical group 0.000 claims 45
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 45
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 41
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 41
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 30
- 125000004438 haloalkoxy group Chemical group 0.000 claims 28
- 125000001188 haloalkyl group Chemical group 0.000 claims 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 27
- 125000001475 halogen functional group Chemical group 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000004404 heteroalkyl group Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 22
- 239000012453 solvate Substances 0.000 claims 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000000539 amino acid group Chemical group 0.000 claims 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 125000005907 alkyl ester group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 10
- 125000001041 indolyl group Chemical group 0.000 claims 10
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000002971 oxazolyl group Chemical group 0.000 claims 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 8
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 235000010290 biphenyl Nutrition 0.000 claims 6
- 239000004305 biphenyl Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 229920003169 water-soluble polymer Polymers 0.000 claims 6
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000002062 proliferating effect Effects 0.000 claims 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 230000017531 blood circulation Effects 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229940080818 propionamide Drugs 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- TVQIPXUZARIUKU-UHFFFAOYSA-N 2-amino-3-(4-methoxyphenyl)-n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]propanamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C(=O)NC1=CC(C=2C(=NOC=2)C=2C=C(OC)C(OC)=C(OC)C=2)=CC=C1OC TVQIPXUZARIUKU-UHFFFAOYSA-N 0.000 claims 1
- JJCHPMHGSKCKQQ-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-3-phenylpropanamide;hydrochloride Chemical compound Cl.COC1=CC=C(C=2C(=NOC=2)C=2C=C(OC)C(OC)=C(OC)C=2)C=C1NC(=O)C(N)CC1=CC=CC=C1 JJCHPMHGSKCKQQ-UHFFFAOYSA-N 0.000 claims 1
- INSKQMXYATXROK-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-4-methylpentanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)C(N)CC(C)C)C(OC)=CC=C1C1=CON=C1C1=CC(OC)=C(OC)C(OC)=C1 INSKQMXYATXROK-UHFFFAOYSA-N 0.000 claims 1
- DPEXZURXDJIYRS-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-3-phenylpropanamide;hydrochloride Chemical compound Cl.COC1=CC=C(C2=C(ON=C2)C=2C=C(OC)C(OC)=C(OC)C=2)C=C1NC(=O)C(N)CC1=CC=CC=C1 DPEXZURXDJIYRS-UHFFFAOYSA-N 0.000 claims 1
- RMIVPAWTINOYTN-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-4-methylpentanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)C(N)CC(C)C)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 RMIVPAWTINOYTN-UHFFFAOYSA-N 0.000 claims 1
- VZNQTDOSOYRZPS-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]propanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)C(C)N)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 VZNQTDOSOYRZPS-UHFFFAOYSA-N 0.000 claims 1
- PSRRXIUWMZYALZ-UHFFFAOYSA-N 2-methoxyethyl n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCOC)=CC(C=2C(=NOC=2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 PSRRXIUWMZYALZ-UHFFFAOYSA-N 0.000 claims 1
- JCQRFUQJIGLYDR-UHFFFAOYSA-N 2-methoxyethyl n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCCOC)=CC(C2=C(ON=C2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 JCQRFUQJIGLYDR-UHFFFAOYSA-N 0.000 claims 1
- SIQBIFMWHGKQKZ-UHFFFAOYSA-N 3-(2-methoxyethoxy)-n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]propanamide Chemical compound C1=C(OC)C(NC(=O)CCOCCOC)=CC(C=2C(=NOC=2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 SIQBIFMWHGKQKZ-UHFFFAOYSA-N 0.000 claims 1
- XWPXYTXYADFILK-UHFFFAOYSA-N 3-(2-methoxyethoxy)-n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]propanamide Chemical compound C1=C(OC)C(NC(=O)CCOCCOC)=CC(C2=C(ON=C2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 XWPXYTXYADFILK-UHFFFAOYSA-N 0.000 claims 1
- MRCBOEZXJKMWGG-UHFFFAOYSA-N 3-amino-n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-4-methylpentanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)CC(N)C(C)C)C(OC)=CC=C1C1=CON=C1C1=CC(OC)=C(OC)C(OC)=C1 MRCBOEZXJKMWGG-UHFFFAOYSA-N 0.000 claims 1
- DONBOJXLJJTXSS-UHFFFAOYSA-N 3-amino-n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-4-methylpentanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)CC(N)C(C)C)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 DONBOJXLJJTXSS-UHFFFAOYSA-N 0.000 claims 1
- JFWYJRZRRPGIOA-UHFFFAOYSA-N 4-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-4-oxobutanoic acid Chemical compound C1=C(NC(=O)CCC(O)=O)C(OC)=CC=C1C1=CON=C1C1=CC(OC)=C(OC)C(OC)=C1 JFWYJRZRRPGIOA-UHFFFAOYSA-N 0.000 claims 1
- CGAQPAVWCRJOPA-UHFFFAOYSA-N 4-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-4-oxobutanoic acid Chemical compound C1=C(NC(=O)CCC(O)=O)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 CGAQPAVWCRJOPA-UHFFFAOYSA-N 0.000 claims 1
- SPBKZHRBFBNYHP-UHFFFAOYSA-N 4-amino-5-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-5-oxopentanoic acid;hydrochloride Chemical compound Cl.C1=C(NC(=O)C(N)CCC(O)=O)C(OC)=CC=C1C1=CON=C1C1=CC(OC)=C(OC)C(OC)=C1 SPBKZHRBFBNYHP-UHFFFAOYSA-N 0.000 claims 1
- KVVGJFZAUGRDBT-UHFFFAOYSA-N 5-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-5-oxopentanoic acid Chemical compound C1=C(NC(=O)CCCC(O)=O)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 KVVGJFZAUGRDBT-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- BXIDEXLELKJLOV-UHFFFAOYSA-N [3-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-3-oxopropyl]azanium;chloride Chemical compound [Cl-].C1=C(NC(=O)CC[NH3+])C(OC)=CC=C1C1=CON=C1C1=CC(OC)=C(OC)C(OC)=C1 BXIDEXLELKJLOV-UHFFFAOYSA-N 0.000 claims 1
- IVRHAIDNQBFRNI-UHFFFAOYSA-N [3-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-3-oxopropyl]azanium;chloride Chemical compound [Cl-].C1=C(NC(=O)CC[NH3+])C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 IVRHAIDNQBFRNI-UHFFFAOYSA-N 0.000 claims 1
- ZEBJSGPCWOFKPK-UHFFFAOYSA-N [4-carboxy-1-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]anilino]-1-oxobutan-2-yl]azanium;chloride Chemical compound Cl.C1=C(NC(=O)C(N)CCC(O)=O)C(OC)=CC=C1C1=C(C=2C=C(OC)C(OC)=C(OC)C=2)ON=C1 ZEBJSGPCWOFKPK-UHFFFAOYSA-N 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 235000009697 arginine Nutrition 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 235000004554 glutamine Nutrition 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 235000014304 histidine Nutrition 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- PZDDSZNXNWYHDQ-UHFFFAOYSA-N n-[2-methoxy-5-[3-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-3-[2-(methylamino)ethylamino]propanamide Chemical compound C1=C(OC)C(NC(=O)CCNCCNC)=CC(C=2C(=NOC=2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 PZDDSZNXNWYHDQ-UHFFFAOYSA-N 0.000 claims 1
- HUWNXPVCNHSXPN-UHFFFAOYSA-N n-[2-methoxy-5-[5-(3,4,5-trimethoxyphenyl)-1,2-oxazol-4-yl]phenyl]-3-[2-(methylamino)ethylamino]propanamide Chemical compound C1=C(OC)C(NC(=O)CCNCCNC)=CC(C2=C(ON=C2)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 HUWNXPVCNHSXPN-UHFFFAOYSA-N 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 0 *c1c(*)[o]nc1* Chemical compound *c1c(*)[o]nc1* 0.000 description 2
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65389005P | 2005-02-17 | 2005-02-17 | |
| US60/653,890 | 2005-02-17 | ||
| US66011205P | 2005-03-08 | 2005-03-08 | |
| US60/660,112 | 2005-03-08 | ||
| US73391205P | 2005-11-04 | 2005-11-04 | |
| US60/733,912 | 2005-11-04 | ||
| PCT/US2006/005761 WO2006089177A2 (en) | 2005-02-17 | 2006-02-16 | Isoxazole combretastin derivatives for the treatment of disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008530240A JP2008530240A (ja) | 2008-08-07 |
| JP2008530240A5 true JP2008530240A5 (https=) | 2009-04-02 |
| JP5123671B2 JP5123671B2 (ja) | 2013-01-23 |
Family
ID=36607371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007556341A Expired - Fee Related JP5123671B2 (ja) | 2005-02-17 | 2006-02-16 | 増殖性疾患の治療のための化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US7884094B2 (https=) |
| EP (1) | EP1919882A2 (https=) |
| JP (1) | JP5123671B2 (https=) |
| KR (1) | KR101364762B1 (https=) |
| CN (1) | CN101142198B (https=) |
| AU (1) | AU2006214164B2 (https=) |
| BR (1) | BRPI0607688A2 (https=) |
| CA (1) | CA2597430C (https=) |
| IL (1) | IL185016A (https=) |
| MX (1) | MX2007009888A (https=) |
| NZ (1) | NZ560712A (https=) |
| SG (1) | SG164378A1 (https=) |
| TW (1) | TWI385160B (https=) |
| WO (1) | WO2006089177A2 (https=) |
| ZA (1) | ZA200706791B (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2663837B2 (ja) | 1993-06-16 | 1997-10-15 | 住友金属工業株式会社 | 鋼帯の蛇行制御装置 |
| TWI297335B (en) | 2001-07-10 | 2008-06-01 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI332943B (en) | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI252847B (en) | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| TWI330079B (en) | 2003-01-15 | 2010-09-11 | Synta Pharmaceuticals Corp | Treatment for cancers |
| CA2546002C (en) | 2003-11-20 | 2012-09-18 | Janssen Pharmaceutica N.V. | 7-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(adp-ribose) polymerase inhibitors |
| BRPI0416206A (pt) | 2003-11-20 | 2006-12-26 | Janssen Pharmaceutica Nv | 2-quinolinonas e 2-quinoxalinonas substituìdas por 6-alquenila e 6-fenilalquila como inibidores de polimerase de poli(adp-ribose) |
| PL1781604T3 (pl) | 2004-06-23 | 2014-01-31 | Synta Pharmaceuticals Corp | Sole bis(tiohydrazydoamidu) do leczenia nowotworów |
| SG154433A1 (en) | 2004-06-30 | 2009-08-28 | Janssen Pharmaceutica Nv | Phthalazine derivatives as parp inhibitors |
| EA011552B1 (ru) | 2004-06-30 | 2009-04-28 | Янссен Фармацевтика Н.В. | Производные хиназолиндиона в качестве ингибиторов parp |
| ATE540936T1 (de) | 2004-06-30 | 2012-01-15 | Janssen Pharmaceutica Nv | Substituierte 2-alkyl-chinazolinonderivate als parp-hemmer |
| MX2007009888A (es) | 2005-02-17 | 2007-10-16 | Synta Pharmaceuticals Corp | Compuestos para el tratamiento de trastornos proliferativos. |
| MX2007012688A (es) | 2005-04-15 | 2008-03-14 | Synta Pharmaceuticals Corp | Terapia de combinacion para el cancer con compuestos de bis(tiohidrazida) amida. |
| RU2475478C2 (ru) | 2006-08-21 | 2013-02-20 | Синта Фармасьютиклз Корп. | Соединения для лечения пролиферативных расстройств |
| JP2010502616A (ja) | 2006-08-31 | 2010-01-28 | シンタ ファーマシューティカルズ コーポレーション | 癌を治療するためのビス（チオヒドラジドアミド）の組み合わせ |
| JP2010503674A (ja) * | 2006-09-14 | 2010-02-04 | シンタ ファーマシューティカルズ コーポレーション | 血管形成治療用化合物 |
| US8299256B2 (en) | 2007-03-08 | 2012-10-30 | Janssen Pharmaceutica Nv | Quinolinone derivatives as PARP and TANK inhibitors |
| DE102007036685A1 (de) | 2007-08-03 | 2009-02-05 | Innora Gmbh | Verbesserte arzneimittelbeschichtete Medizinprodukte deren Herstellung und Verwendung |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8404713B2 (en) | 2007-10-26 | 2013-03-26 | Janssen Pharmaceutica Nv | Quinolinone derivatives as PARP inhibitors |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN101981013B (zh) | 2008-03-27 | 2013-05-29 | 詹森药业有限公司 | 作为parp和微管蛋白聚合抑制剂的四氢菲啶酮和四氢环戊二烯并喹啉酮 |
| ES2367760T3 (es) | 2008-03-27 | 2011-11-08 | Janssen Pharmaceutica, N.V. | Derivados de quinazolinona como inhibidores de la polimerización de la tubulina. |
| ES2439767T3 (es) * | 2008-08-01 | 2014-01-24 | Purdue Pharma Lp | Compuestos de tetrahidropiridinilo y dihidropirrolilo y uso de los mismos |
| TWI392673B (zh) | 2008-08-27 | 2013-04-11 | Calcimedica Inc | 調控細胞內鈣離子濃度之化合物 |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8143269B2 (en) | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| SG178106A1 (en) * | 2009-08-05 | 2012-03-29 | Versitech Ltd | Antiviral compounds and methods of making and using thereof |
| EP2477982A4 (en) | 2009-09-16 | 2013-04-03 | Calcimedica Inc | COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| JP6112486B2 (ja) | 2010-04-27 | 2017-04-12 | カルシメディカ，インク． | 細胞内カルシウムを調節する化合物 |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8906943B2 (en) | 2010-08-05 | 2014-12-09 | John R. Cashman | Synthetic compounds and methods to decrease nicotine self-administration |
| EP2609095A4 (en) | 2010-08-27 | 2014-06-18 | Calcimedica Inc | COMPOUNDS MODULATING INTRACELLULAR CALCIUM |
| US8802895B2 (en) * | 2010-10-18 | 2014-08-12 | Cleveland State University | Amide derivatives of benzene-sulfonanilide, pharmaceutical composition thereof and method for cancer treatment using the same |
| CN102731488A (zh) * | 2011-04-02 | 2012-10-17 | 中国医学科学院药物研究所 | 苯并咪唑类衍生物、及其制法和药物组合物与用途 |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| JP6280546B2 (ja) | 2012-06-26 | 2018-02-14 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法 |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| KR20160061911A (ko) | 2013-04-08 | 2016-06-01 | 데니스 엠. 브라운 | 최적하 투여된 화학 화합물의 치료 효과 |
| US20150073008A1 (en) * | 2013-09-12 | 2015-03-12 | Merz Pharma Gmbh & Co. Kgaa | Topical Application of Vinca Alkaloids for the Treatment of Actinic Keratosis |
| WO2015057964A2 (en) * | 2013-10-16 | 2015-04-23 | The Board Of Regents Of The University Of Texas System | Modulation of mrtf-a activity in pathologic fibrosis and wound healing |
| JP6524069B2 (ja) * | 2014-04-30 | 2019-06-05 | 日本カーバイド工業株式会社 | オキシラン化合物及びそれを用いた含窒素複素環式化合物を製造する方法 |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| US9783519B2 (en) * | 2015-06-18 | 2017-10-10 | Hong Kong Baptist University | Palladium/silver co-catalyzed tandem reactions synthesis of phenylacetophenone derivatives by oxabenzonorbornadienes with terminal alkynes and their anti-tumor or anti-cancer activities |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| CN108358864B (zh) * | 2017-12-15 | 2020-07-17 | 五邑大学 | 一种2-酰基-5-苯基噁唑类微管蛋白抑制剂的制备方法及应用 |
| CN108707147A (zh) * | 2018-06-20 | 2018-10-26 | 桑文军 | 一种新型微管蛋白抑制剂及其在抗肿瘤药物中的应用 |
| JP2023528537A (ja) | 2020-03-20 | 2023-07-04 | カルシメディカ，インク． | 急性肺傷害及び急性呼吸窮迫症候群を処置するための方法及び組成物 |
| CA3198798A1 (en) | 2020-11-13 | 2022-05-19 | Kenneth Stauderman | Improved synthesis of crac channel inhibitors |
| CN112979567B (zh) * | 2021-03-05 | 2023-07-18 | 中国医科大学 | Cdk12小分子抑制剂的化合物及其应用 |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996237A (en) * | 1987-01-06 | 1991-02-26 | Arizona Board Of Regents | Combretastatin A-4 |
| CA1338645C (en) * | 1987-01-06 | 1996-10-15 | George R. Pettit | Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins" |
| US5663053A (en) * | 1992-02-11 | 1997-09-02 | Smithkline Beecham Corporation | Inhibition of inflammatory lipid mediators |
| US5430062A (en) * | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
| US5731353A (en) * | 1993-09-08 | 1998-03-24 | Ajinomoto Co., Inc. | Stilbene derivatives and pharmaceutical compositions containing them |
| US5561122A (en) * | 1994-12-22 | 1996-10-01 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Combretastatin A-4 prodrug |
| TW334418B (en) * | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| EP0833664A1 (en) * | 1995-06-12 | 1998-04-08 | G.D. SEARLE & CO. | Combination of a cyclooxygenase-2 inhibitor and a leukotriene b 4? receptor antagonist for the treatment of inflammations |
| ES2247604T3 (es) * | 1995-06-12 | 2006-03-01 | G.D. SEARLE & CO. | Composiciones que comprenden un inhibidor de ciclooxigenasa-2 y un inhibidor de 5-lipoxigenasa. |
| BR9611047A (pt) | 1995-10-17 | 2000-03-08 | Searle & Co | Processo de deteção de ciclo oxigenase-2 |
| US5859035A (en) * | 1996-04-03 | 1999-01-12 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
| DE69729946T2 (de) | 1996-10-15 | 2005-01-20 | G.D. Searle Llc | Verwendung von cyclooxygenase-2 inhibitoren zur behandlung und verbeugung von neoplasia |
| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| US5886015A (en) * | 1997-06-02 | 1999-03-23 | Rohm And Haas Company | Benzyloxy substituted aromatics and their use as fungicides and insecticides |
| AU8127298A (en) | 1997-07-09 | 1999-02-08 | Nippon Soda Co., Ltd. | Isoxazole compounds, process for the preparation thereof, and insecticides and acaricides |
| US5972986A (en) * | 1997-10-14 | 1999-10-26 | G.D. Searle & Co. | Method of using cyclooxygenase-2 inhibitors in the treatment and prevention of neoplasia |
| WO1999051246A1 (en) * | 1998-04-03 | 1999-10-14 | Ajinomoto Co., Inc. | Antitumor agents |
| JP4191825B2 (ja) | 1998-09-10 | 2008-12-03 | あすか製薬株式会社 | ５−アミノイソキサゾール誘導体 |
| GEP20033045B (en) | 1998-09-17 | 2003-08-25 | Bristol Myers Squibb Co | Method for Treating Diabetes |
| WO2000048606A1 (en) * | 1999-02-18 | 2000-08-24 | Oxigene, Inc. | Compositions and methods for use in targeting vascular destruction |
| US6849656B1 (en) * | 1999-09-17 | 2005-02-01 | Baylor University | Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents |
| CA2407967C (en) * | 2000-03-10 | 2010-10-05 | Baylor University | Tubulin binding ligands and corresponding prodrug constructs |
| AU2001273040A1 (en) | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| EP1317453B1 (en) | 2000-09-15 | 2006-08-09 | Vertex Pharmaceuticals Incorporated | Isoxazoles and their use as inhibitors of erk |
| US20030105141A1 (en) * | 2001-04-17 | 2003-06-05 | Ping Gao | Finely self-emulsifiable pharmaceutical composition |
| US20020169881A1 (en) * | 2001-05-10 | 2002-11-14 | International Business Machines Corporation | Method and apparatus for distributed access to services in a network data processing system |
| AU2002337843A1 (en) | 2001-10-12 | 2003-04-22 | Onconova Therapeutics, Inc. | Processes for the preparation of substituted isoxazoles and 2-isoxazolines |
| CA2473740A1 (en) | 2002-01-18 | 2003-07-31 | David Solow-Cordero | Methods of treating conditions associated with an edg receptor |
| EP1336602A1 (en) | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
| EP1494662B1 (en) | 2002-04-11 | 2012-11-28 | Children's Medical Center Corporation | Tnp-470-hpma-methacrylic acid copolymer conjugates and use thereof |
| MXPA05000862A (es) | 2002-07-31 | 2005-04-19 | Pharmacia Corp | Forma de dosificacion farmaceutica capaz de mantener un perfil de disolucion estable tras el almacenamiento. |
| EP1542995A1 (en) | 2002-09-18 | 2005-06-22 | Pfizer Products Inc. | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
| SI1611112T1 (sl) | 2003-02-11 | 2012-12-31 | Vernalis (R&D) Limited | Izoksazolne spojine kot inhibitorji vroäśinskih ĺ ok proteinov |
| WO2004087153A2 (en) | 2003-03-28 | 2004-10-14 | Chiron Corporation | Use of organic compounds for immunopotentiation |
| MXPA05011523A (es) | 2003-04-30 | 2006-01-23 | Inst For Pharm Discovery Inc | Heteroarilos sustituidos como inhibidores de proteinas de tirosina fosfatasas. |
| WO2004110351A2 (en) | 2003-05-14 | 2004-12-23 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis c virus |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| GB0315111D0 (en) | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| ITRM20030355A1 (it) | 2003-07-18 | 2005-01-19 | Sigma Tau Ind Farmaceuti | Composti ad attivita' citotossica derivati della combretastatina. |
| TWI339206B (en) * | 2003-09-04 | 2011-03-21 | Vertex Pharma | Compositions useful as inhibitors of protein kinases |
| WO2005044194A2 (en) | 2003-10-28 | 2005-05-19 | Pharmacia Corporation | TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR |
| KR100544347B1 (ko) * | 2003-12-11 | 2006-01-23 | 한국생명공학연구원 | 디아릴이소옥사졸계 화합물을 유효성분으로 함유하는 암 예방 및 치료용 약학적 조성물 |
| WO2005066162A1 (en) | 2003-12-23 | 2005-07-21 | Human Biomolecular Research Institute | Synthetic compounds and derivatives as modulators of smoking or nicotine ingestion and lung cancer |
| MX2007009888A (es) | 2005-02-17 | 2007-10-16 | Synta Pharmaceuticals Corp | Compuestos para el tratamiento de trastornos proliferativos. |
| WO2006092059A1 (en) | 2005-03-04 | 2006-09-08 | Fan Wu | Design and synthesis of novel antimicrobials |
| WO2006124687A1 (en) | 2005-05-12 | 2006-11-23 | University Of Medicine And Dentistry Of New Jersey | Opioid receptor subtype-selective agents |
-
2006
- 2006-02-16 MX MX2007009888A patent/MX2007009888A/es active IP Right Grant
- 2006-02-16 SG SG201005267-8A patent/SG164378A1/en unknown
- 2006-02-16 BR BRPI0607688-2A patent/BRPI0607688A2/pt not_active IP Right Cessation
- 2006-02-16 KR KR1020077021347A patent/KR101364762B1/ko not_active Expired - Fee Related
- 2006-02-16 CN CN2006800053106A patent/CN101142198B/zh not_active Expired - Fee Related
- 2006-02-16 WO PCT/US2006/005761 patent/WO2006089177A2/en not_active Ceased
- 2006-02-16 JP JP2007556341A patent/JP5123671B2/ja not_active Expired - Fee Related
- 2006-02-16 US US11/355,922 patent/US7884094B2/en not_active Expired - Fee Related
- 2006-02-16 AU AU2006214164A patent/AU2006214164B2/en not_active Ceased
- 2006-02-16 EP EP06735424A patent/EP1919882A2/en not_active Withdrawn
- 2006-02-16 CA CA2597430A patent/CA2597430C/en not_active Expired - Fee Related
- 2006-02-16 NZ NZ560712A patent/NZ560712A/en not_active IP Right Cessation
- 2006-02-17 TW TW095105351A patent/TWI385160B/zh not_active IP Right Cessation
-
2007
- 2007-08-02 IL IL185016A patent/IL185016A/en not_active IP Right Cessation
- 2007-08-15 ZA ZA2007/06791A patent/ZA200706791B/en unknown
-
2010
- 2010-09-16 US US12/883,883 patent/US8269017B2/en not_active Expired - Fee Related
-
2012
- 2012-07-26 US US13/558,886 patent/US8598366B2/en not_active Expired - Fee Related
-
2013
- 2013-10-15 US US14/053,845 patent/US9090603B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008530240A5 (https=) | ||
| CA2597430A1 (en) | Isoxazole combretastin derivatives for the treatment of disorders | |
| JP6955648B2 (ja) | 異常炎症反応に関連する状態を処置するための方法および組成物 | |
| RU2539917C2 (ru) | Способы лечения синдрома сосудистой утечки | |
| JP2009504763A5 (https=) | ||
| US20100279410A1 (en) | Compounds for the treatment of proliferative disorders | |
| JP2009530398A5 (https=) | ||
| JP2009529059A5 (https=) | ||
| RU2009105179A (ru) | Сульфониламинокарбонилпроизводные амидов холевой кислоты для применения в качестве иммуномодуляторов | |
| HRP20110076T1 (hr) | Farmaceutske kombinacije koje sadrže 3-(3-dimetilamino-1-etil-2-metil-propil)-fenol i paracetamol | |
| JP2015512413A5 (https=) | ||
| JP2021522247A (ja) | 肝疾患における好中球エラスターゼ阻害薬の使用 | |
| JP2010503674A5 (https=) | ||
| JP2010502736A5 (https=) | ||
| JP2010503674A (ja) | 血管形成治療用化合物 | |
| JP2020520910A5 (https=) | ||
| JP2023553989A5 (https=) | ||
| JP2009515996A (ja) | 増殖性疾患の治療のためのチアゾール | |
| JP2009515996A5 (https=) | ||
| JP2004536788A5 (https=) | ||
| RU2019104928A (ru) | Производное индола, используемое в качестве ингибитора CRTH2 | |
| RU2019123592A (ru) | Производные оксазола для применения при лечении рака | |
| JP2020510655A5 (https=) | ||
| RU2017134594A (ru) | Фармацевтическая композиция, включающая полипептид |