JP2006515310A5 - - Google Patents
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- Publication number
- JP2006515310A5 JP2006515310A5 JP2004565816A JP2004565816A JP2006515310A5 JP 2006515310 A5 JP2006515310 A5 JP 2006515310A5 JP 2004565816 A JP2004565816 A JP 2004565816A JP 2004565816 A JP2004565816 A JP 2004565816A JP 2006515310 A5 JP2006515310 A5 JP 2006515310A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- dihydroisoindol
- pharmaceutically acceptable
- stereoisomer
- 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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- 150000001875 compounds Chemical class 0.000 claims 62
- 150000003839 salts Chemical class 0.000 claims 24
- 239000012453 solvate Substances 0.000 claims 24
- 239000003814 drug Substances 0.000 claims 22
- 239000000651 prodrug Substances 0.000 claims 21
- 229940002612 prodrug Drugs 0.000 claims 21
- 238000004519 manufacturing process Methods 0.000 claims 20
- 241000124008 Mammalia Species 0.000 claims 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- -1 3-cyclopropylmethoxy-4-difluoromethoxyphenyl Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- NMYSRJLHCZVHMX-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[3,4-bis(difluoromethoxy)phenyl]-n,n-dimethylpropanamide Chemical compound O=C1C2=CC=CC(NC(C)=O)=C2C(=O)N1C(CC(=O)N(C)C)C1=CC=C(OC(F)F)C(OC(F)F)=C1 NMYSRJLHCZVHMX-UHFFFAOYSA-N 0.000 claims 1
- ZDIMYZUGUMNLKL-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-n,n-dimethylpropanamide Chemical compound O=C1C2=CC=CC(NC(C)=O)=C2C(=O)N1C(CC(=O)N(C)C)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 ZDIMYZUGUMNLKL-UHFFFAOYSA-N 0.000 claims 1
- PNMNETUNJABIGE-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]propanamide Chemical compound O=C1C=2C(NC(=O)C)=CC=CC=2C(=O)N1C(CC(N)=O)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 PNMNETUNJABIGE-UHFFFAOYSA-N 0.000 claims 1
- CGSYCSBNONPYAH-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]propanoic acid Chemical compound O=C1C=2C(NC(=O)C)=CC=CC=2C(=O)N1C(CC(O)=O)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 CGSYCSBNONPYAH-UHFFFAOYSA-N 0.000 claims 1
- RATZQLNVDVMADG-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]-n,n-dimethylpropanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 RATZQLNVDVMADG-UHFFFAOYSA-N 0.000 claims 1
- ZBMDUPLBQYYSSM-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]-n-hydroxypropanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)NO)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 ZBMDUPLBQYYSSM-UHFFFAOYSA-N 0.000 claims 1
- GIWGNYYSCIELPD-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(N)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 GIWGNYYSCIELPD-UHFFFAOYSA-N 0.000 claims 1
- GMCGLHFSWYXMHS-UHFFFAOYSA-N 3-(4-acetamido-1,3-dioxoisoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoic acid Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 GMCGLHFSWYXMHS-UHFFFAOYSA-N 0.000 claims 1
- KPJCKOFTCSMTKO-UHFFFAOYSA-N 3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]-n,n-dimethylpropanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 KPJCKOFTCSMTKO-UHFFFAOYSA-N 0.000 claims 1
- GJMWVXJKYKBKSY-UHFFFAOYSA-N 3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]-n-hydroxypropanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)NO)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 GJMWVXJKYKBKSY-UHFFFAOYSA-N 0.000 claims 1
- QKCSSGBWAGLNIG-UHFFFAOYSA-N 3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(N)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 QKCSSGBWAGLNIG-UHFFFAOYSA-N 0.000 claims 1
- CXQFXXMEAOLQPJ-UHFFFAOYSA-N 3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoic acid Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 CXQFXXMEAOLQPJ-UHFFFAOYSA-N 0.000 claims 1
- RSKLHAIZYXWUMY-UHFFFAOYSA-N 3-(4-amino-3-oxo-1h-isoindol-2-yl)-3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-n,n-dimethylpropanamide Chemical compound C1C2=CC=CC(N)=C2C(=O)N1C(CC(=O)N(C)C)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 RSKLHAIZYXWUMY-UHFFFAOYSA-N 0.000 claims 1
- JHAVRBWNKNAERF-UHFFFAOYSA-N 3-[3,4-bis(difluoromethoxy)phenyl]-3-[4-(cyclopropanecarbonylamino)-3-oxo-1h-isoindol-2-yl]propanoic acid Chemical compound C=1C=C(OC(F)F)C(OC(F)F)=CC=1C(CC(=O)O)N(C(C1=2)=O)CC1=CC=CC=2NC(=O)C1CC1 JHAVRBWNKNAERF-UHFFFAOYSA-N 0.000 claims 1
- BBETXSAMADLPQG-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(1,3-dioxoisoindol-2-yl)-n-hydroxypropanamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(CC(=O)NO)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 BBETXSAMADLPQG-UHFFFAOYSA-N 0.000 claims 1
- URRMMOHXVKMEQE-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(1,3-dioxoisoindol-2-yl)propanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(CC(=O)O)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 URRMMOHXVKMEQE-UHFFFAOYSA-N 0.000 claims 1
- UONHGHCJNPCFTH-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(4-nitro-3-oxo-1h-isoindol-2-yl)propanoic acid Chemical compound C1C2=CC=CC([N+]([O-])=O)=C2C(=O)N1C(CC(=O)O)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 UONHGHCJNPCFTH-UHFFFAOYSA-N 0.000 claims 1
- PZCZJERSAONWMF-UHFFFAOYSA-N 3-[4-(cyclopropanecarbonylamino)-3-oxo-1h-isoindol-2-yl]-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoic acid Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 PZCZJERSAONWMF-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 claims 1
- 108010000817 Leuprolide Proteins 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 208000002399 aphthous stomatitis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 229960000997 bicalutamide Drugs 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 208000020670 canker sore Diseases 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 claims 1
- 229960004338 leuprorelin Drugs 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 210000001165 lymph node Anatomy 0.000 claims 1
- 210000004962 mammalian cell Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- BENDWIAVMODELR-UHFFFAOYSA-N methyl 3-(4-acetamido-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoate Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)OC)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 BENDWIAVMODELR-UHFFFAOYSA-N 0.000 claims 1
- SEYLOWHVLMDMHY-UHFFFAOYSA-N methyl 3-(4-amino-3-oxo-1h-isoindol-2-yl)-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoate Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)OC)N2C(C3=C(N)C=CC=C3C2)=O)=C1 SEYLOWHVLMDMHY-UHFFFAOYSA-N 0.000 claims 1
- LCSAIQDBIRVVHT-UHFFFAOYSA-N methyl 3-[3,4-bis(difluoromethoxy)phenyl]-3-[7-chloro-4-(cyclopropanecarbonylamino)-3-oxo-1h-isoindol-2-yl]propanoate Chemical compound C=1C=C(OC(F)F)C(OC(F)F)=CC=1C(CC(=O)OC)N(C1=O)CC(C(=CC=2)Cl)=C1C=2NC(=O)C1CC1 LCSAIQDBIRVVHT-UHFFFAOYSA-N 0.000 claims 1
- NQEDSOZFQXUPKW-UHFFFAOYSA-N methyl 3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(4-nitro-3-oxo-1h-isoindol-2-yl)propanoate Chemical compound C1C2=CC=CC([N+]([O-])=O)=C2C(=O)N1C(CC(=O)OC)C(C=1)=CC=C(OC(F)F)C=1OCC1CC1 NQEDSOZFQXUPKW-UHFFFAOYSA-N 0.000 claims 1
- RXODVOZOQUCBKM-UHFFFAOYSA-N methyl 3-[4-(cyclopropanecarbonylamino)-3-oxo-1h-isoindol-2-yl]-3-[4-(difluoromethoxy)-3-ethoxyphenyl]propanoate Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)OC)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 RXODVOZOQUCBKM-UHFFFAOYSA-N 0.000 claims 1
- IUXDYCMYPDJCRR-UHFFFAOYSA-N methyl 3-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-(4-nitro-3-oxo-1h-isoindol-2-yl)propanoate Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)OC)N2C(C3=C(C=CC=C3C2)[N+]([O-])=O)=O)=C1 IUXDYCMYPDJCRR-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- HPJXCPXWZXQLJT-UHFFFAOYSA-N n-[2-[1-[3,4-bis(difluoromethoxy)phenyl]-3-(dimethylamino)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C=1C=C(OC(F)F)C(OC(F)F)=CC=1C(CC(=O)N(C)C)N(C(C1=2)=O)CC1=CC=CC=2NC(=O)C1CC1 HPJXCPXWZXQLJT-UHFFFAOYSA-N 0.000 claims 1
- SGBDKKJUPRQUDI-UHFFFAOYSA-N n-[2-[1-[3,4-bis(difluoromethoxy)phenyl]-3-(hydroxyamino)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C=1C=C(OC(F)F)C(OC(F)F)=CC=1C(CC(=O)NO)N(C(C1=2)=O)CC1=CC=CC=2NC(=O)C1CC1 SGBDKKJUPRQUDI-UHFFFAOYSA-N 0.000 claims 1
- CDVJKBYRNUASOS-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 CDVJKBYRNUASOS-UHFFFAOYSA-N 0.000 claims 1
- ZPKWSSKKWFZWQR-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-2-methylsulfonylethyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 ZPKWSSKKWFZWQR-UHFFFAOYSA-N 0.000 claims 1
- XPDIHKBYHQCQMM-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-(dimethylamino)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)N(C)C)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 XPDIHKBYHQCQMM-UHFFFAOYSA-N 0.000 claims 1
- PMYPAKOPWFIPGP-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-(hydroxyamino)-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)NO)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 PMYPAKOPWFIPGP-UHFFFAOYSA-N 0.000 claims 1
- PDLUWKABAUZSBP-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-morpholin-4-yl-3-oxopropyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)N2CCOCC2)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 PDLUWKABAUZSBP-UHFFFAOYSA-N 0.000 claims 1
- HUVALBBFEOXNDH-UHFFFAOYSA-N n-[2-[1-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-morpholin-4-yl-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]acetamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(=O)N2CCOCC2)N2C(C3=C(NC(C)=O)C=CC=C3C2)=O)=C1 HUVALBBFEOXNDH-UHFFFAOYSA-N 0.000 claims 1
- QAKQJLFQAHNCHD-UHFFFAOYSA-N n-[2-[3-amino-1-[3,4-bis(difluoromethoxy)phenyl]-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C=1C=C(OC(F)F)C(OC(F)F)=CC=1C(CC(=O)N)N(C(C1=2)=O)CC1=CC=CC=2NC(=O)C1CC1 QAKQJLFQAHNCHD-UHFFFAOYSA-N 0.000 claims 1
- HBFYGEBAEMMUHD-UHFFFAOYSA-N n-[2-[3-amino-1-[4-(difluoromethoxy)-3-ethoxyphenyl]-3-oxopropyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical compound C1=C(OC(F)F)C(OCC)=CC(C(CC(N)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 HBFYGEBAEMMUHD-UHFFFAOYSA-N 0.000 claims 1
- 230000002611 ovarian Effects 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 238000000554 physical therapy Methods 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 229960002530 sargramostim Drugs 0.000 claims 1
- 108010038379 sargramostim Proteins 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
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| KR20050072790A (ko) * | 2002-11-06 | 2005-07-12 | 셀진 코포레이션 | 골수증식 질환의 치료 및 관리를 위한 선택적 시토킨 억제약물의 사용 방법 및 이를 포함하는 조성물 |
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-
2003
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- 2003-12-29 AU AU2003303511A patent/AU2003303511B2/en not_active Ceased
- 2003-12-29 BR BR0317885-4A patent/BR0317885A/pt not_active IP Right Cessation
- 2003-12-29 EP EP03808605A patent/EP1587474B1/en not_active Expired - Lifetime
- 2003-12-29 DE DE60330187T patent/DE60330187D1/de not_active Expired - Lifetime
- 2003-12-29 JP JP2004565816A patent/JP5269281B2/ja not_active Expired - Fee Related
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- 2003-12-29 WO PCT/US2003/041568 patent/WO2004060313A2/en not_active Ceased
- 2003-12-29 US US10/748,085 patent/US7173058B2/en not_active Expired - Fee Related
- 2003-12-29 CN CNA2003801099071A patent/CN1802353A/zh active Pending
- 2003-12-29 CA CA2511843A patent/CA2511843C/en not_active Expired - Fee Related
- 2003-12-29 AT AT03808605T patent/ATE449081T1/de not_active IP Right Cessation
- 2003-12-29 NZ NZ541487A patent/NZ541487A/en unknown
- 2003-12-29 ES ES03808605T patent/ES2333220T3/es not_active Expired - Lifetime
- 2003-12-29 ZA ZA200505308A patent/ZA200505308B/en unknown
- 2003-12-30 TW TW092137472A patent/TW200418779A/zh unknown
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2005
- 2005-06-28 IL IL169439A patent/IL169439A0/en unknown
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- 2006-11-16 US US11/601,355 patent/US7504427B2/en not_active Expired - Lifetime
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2009
- 2009-01-30 US US12/363,664 patent/US7893102B2/en not_active Expired - Fee Related
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2011
- 2011-01-20 US US13/010,738 patent/US8158672B2/en not_active Expired - Lifetime
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