JP2008530240A5 - - Google Patents
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- 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
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- -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
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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 |
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-
2006
- 2006-02-16 AU AU2006214164A patent/AU2006214164B2/en not_active Ceased
- 2006-02-16 CA CA2597430A patent/CA2597430C/en not_active Expired - Fee Related
- 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 EP EP06735424A patent/EP1919882A2/en not_active Withdrawn
- 2006-02-16 CN CN2006800053106A patent/CN101142198B/zh not_active Expired - Fee Related
- 2006-02-16 SG SG201005267-8A patent/SG164378A1/en unknown
- 2006-02-16 KR KR1020077021347A patent/KR101364762B1/ko not_active Expired - Fee Related
- 2006-02-16 NZ NZ560712A patent/NZ560712A/en not_active IP Right Cessation
- 2006-02-16 MX MX2007009888A patent/MX2007009888A/es active IP Right Grant
- 2006-02-16 BR BRPI0607688-2A patent/BRPI0607688A2/pt not_active IP Right Cessation
- 2006-02-16 WO PCT/US2006/005761 patent/WO2006089177A2/en not_active Ceased
- 2006-02-17 TW TW095105351A patent/TWI385160B/zh not_active IP Right Cessation
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2007
- 2007-08-02 IL IL185016A patent/IL185016A/en not_active IP Right Cessation
- 2007-08-15 ZA ZA2007/06791A patent/ZA200706791B/en unknown
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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
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2013
- 2013-10-15 US US14/053,845 patent/US9090603B2/en not_active Expired - Fee Related
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