JP2010505933A5 - - Google Patents
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- Publication number
- JP2010505933A5 JP2010505933A5 JP2009531919A JP2009531919A JP2010505933A5 JP 2010505933 A5 JP2010505933 A5 JP 2010505933A5 JP 2009531919 A JP2009531919 A JP 2009531919A JP 2009531919 A JP2009531919 A JP 2009531919A JP 2010505933 A5 JP2010505933 A5 JP 2010505933A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- phenyl
- methanone
- dihydroxy
- isoindol
- 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 description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 208000002193 Pain Diseases 0.000 claims description 42
- 238000011282 treatment Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 230000002265 prevention Effects 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 208000024891 symptom Diseases 0.000 claims description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- -1 NR c Inorganic materials 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 101150053721 Cdk5 gene Proteins 0.000 claims description 14
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- 239000003429 antifungal agent Substances 0.000 claims description 14
- 229940121375 antifungal agent Drugs 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 8
- 208000004454 Hyperalgesia Diseases 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
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- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 230000002538 fungal effect Effects 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- YYVAXCVMFDJHBF-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-methylpiperazin-1-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)N2CCN(C)CC2)=C1O YYVAXCVMFDJHBF-UHFFFAOYSA-N 0.000 claims description 6
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 6
- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 230000005875 antibody response Effects 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
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- 230000001575 pathological effect Effects 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 230000029812 viral genome replication Effects 0.000 claims description 5
- RKWHYDXSPNNDBR-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[4-(3-morpholin-4-ylpropoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(OCCCN4CCOCC4)C=CC=C3C2)=C1O RKWHYDXSPNNDBR-UHFFFAOYSA-N 0.000 claims description 4
- JVQQVJXMYAIHFT-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-hydroxy-1-methylpiperidin-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)C2(O)CCN(C)CC2)=C1O JVQQVJXMYAIHFT-UHFFFAOYSA-N 0.000 claims description 4
- HIIKFACAQJEYEI-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(1-methylpiperidin-4-yl)amino]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(NC4CCN(C)CC4)=CC=C3C2)=C1O HIIKFACAQJEYEI-UHFFFAOYSA-N 0.000 claims description 4
- IMCANAAIYOYWDU-UHFFFAOYSA-N (5-chloro-2,4-dihydroxyphenyl)-[5-(4-methylpiperazin-1-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1CN(C)CCN1C1=CC=C(CN(C2)C(=O)C=3C(=CC(O)=C(Cl)C=3)O)C2=C1 IMCANAAIYOYWDU-UHFFFAOYSA-N 0.000 claims description 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 4
- 206010058019 Cancer Pain Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 4
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 4
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 4
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- 208000035154 Hyperesthesia Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 4
- 208000001294 Nociceptive Pain Diseases 0.000 claims description 4
- 241000223960 Plasmodium falciparum Species 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 208000035868 Vascular inflammations Diseases 0.000 claims description 4
- 206010047095 Vascular pain Diseases 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 206010053552 allodynia Diseases 0.000 claims description 4
- 239000003096 antiparasitic agent Substances 0.000 claims description 4
- 229940125687 antiparasitic agent Drugs 0.000 claims description 4
- 239000003904 antiprotozoal agent Substances 0.000 claims description 4
- 208000037849 arterial hypertension Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- 230000009610 hypersensitivity Effects 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 230000000926 neurological effect Effects 0.000 claims description 4
- IFRGXKKQHBVPCQ-UHFFFAOYSA-N onalespib Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCN(C)CC4)=CC=C3C2)=C1O IFRGXKKQHBVPCQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003071 parasitic effect Effects 0.000 claims description 4
- 208000004371 toothache Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
- 208000009935 visceral pain Diseases 0.000 claims description 4
- YCAYPVJEOCBCCR-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-piperazin-1-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)N2CCNCC2)=C1O YCAYPVJEOCBCCR-UHFFFAOYSA-N 0.000 claims description 3
- JGSGWWWQXTYLGD-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(dimethylamino)methyl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(CN(C)C)=CC=C3C2)=C1O JGSGWWWQXTYLGD-UHFFFAOYSA-N 0.000 claims description 3
- QVVRLPMMRCAKBP-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[2-(dimethylamino)ethoxy]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(OCCN(C)C)=CC=C3C2)=C1O QVVRLPMMRCAKBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 241000282412 Homo Species 0.000 claims description 3
- 244000052616 bacterial pathogen Species 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- SSZRLOSKSNZFFK-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(4-fluoro-1,3-dihydroisoindol-2-yl)methanone;hydrochloride Chemical compound Cl.C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(F)C=CC=C3C2)=C1O SSZRLOSKSNZFFK-UHFFFAOYSA-N 0.000 claims description 2
- KPWQHNKPRDITRE-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-fluoro-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(F)=CC=C3C2)=C1O KPWQHNKPRDITRE-UHFFFAOYSA-N 0.000 claims description 2
- CGDIZMUZKWJVOO-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-hydroxy-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(O)=CC=C3C2)=C1O CGDIZMUZKWJVOO-UHFFFAOYSA-N 0.000 claims description 2
- XGWIZXRDVRVZEK-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-methoxy-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1C2=CC(OC)=CC=C2CN1C(=O)C1=CC(C(C)C)=C(O)C=C1O XGWIZXRDVRVZEK-UHFFFAOYSA-N 0.000 claims description 2
- JUTGATVTVPQMEL-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-methyl-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(C)=CC=C3C2)=C1O JUTGATVTVPQMEL-UHFFFAOYSA-N 0.000 claims description 2
- LUCGOGCKXFESLJ-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-(5-morpholin-4-yl-1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)N2CCOCC2)=C1O LUCGOGCKXFESLJ-UHFFFAOYSA-N 0.000 claims description 2
- BHIGZZZLNMKWKD-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[4-(4-methylpiperazin-1-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(N4CCN(C)CC4)C=CC=C3C2)=C1O BHIGZZZLNMKWKD-UHFFFAOYSA-N 0.000 claims description 2
- HHHYTVUIDNOPQP-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[4-(piperidin-4-ylamino)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(NC4CCNCC4)C=CC=C3C2)=C1O HHHYTVUIDNOPQP-UHFFFAOYSA-N 0.000 claims description 2
- HXJZVSQZQZCYGZ-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[4-[2-(2-methoxyethoxy)ethoxy]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1C=2C(OCCOCCOC)=CC=CC=2CN1C(=O)C1=CC(C(C)C)=C(O)C=C1O HXJZVSQZQZCYGZ-UHFFFAOYSA-N 0.000 claims description 2
- IVIKKSNFTPZPFF-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[4-[2-(dimethylamino)ethoxy]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(OCCN(C)C)C=CC=C3C2)=C1O IVIKKSNFTPZPFF-UHFFFAOYSA-N 0.000 claims description 2
- LYUXFHBOSWVIRE-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(2-methoxyethoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1C2=CC(OCCOC)=CC=C2CN1C(=O)C1=CC(C(C)C)=C(O)C=C1O LYUXFHBOSWVIRE-UHFFFAOYSA-N 0.000 claims description 2
- AMUHXLKGSWMZEA-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(3-morpholin-4-ylpropoxy)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(OCCCN4CCOCC4)=CC=C3C2)=C1O AMUHXLKGSWMZEA-UHFFFAOYSA-N 0.000 claims description 2
- SVHNLCFHSPNERJ-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-hydroxypiperidin-4-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)C2(O)CCNCC2)=C1O SVHNLCFHSPNERJ-UHFFFAOYSA-N 0.000 claims description 2
- UONLQFDHEGREOV-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-morpholin-4-ylpiperidin-1-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)N2CCC(CC2)N2CCOCC2)=C1O UONLQFDHEGREOV-UHFFFAOYSA-N 0.000 claims description 2
- PEDLIUGWZBQXFP-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-piperazin-1-ylphenyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)C=2C=CC(=CC=2)N2CCNCC2)=C1O PEDLIUGWZBQXFP-UHFFFAOYSA-N 0.000 claims description 2
- MTRYSRYJRINGBV-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(4-propan-2-ylpiperazin-1-yl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1CN(C(C)C)CCN1C1=CC=C(CN(C2)C(=O)C=3C(=CC(O)=C(C(C)C)C=3)O)C2=C1 MTRYSRYJRINGBV-UHFFFAOYSA-N 0.000 claims description 2
- IBDJXXHTJPHOJQ-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(morpholin-4-ylmethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCOCC4)=CC=C3C2)=C1O IBDJXXHTJPHOJQ-UHFFFAOYSA-N 0.000 claims description 2
- AFCDQRNSLCTCHH-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(piperidin-1-ylmethyl)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(CN4CCCCC4)=CC=C3C2)=C1O AFCDQRNSLCTCHH-UHFFFAOYSA-N 0.000 claims description 2
- ZSOPJQACGPRLBY-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-(piperidin-4-ylamino)-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(NC4CCNCC4)=CC=C3C2)=C1O ZSOPJQACGPRLBY-UHFFFAOYSA-N 0.000 claims description 2
- RKICJLSKDUSLPK-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[2-(2,2-dimethylpropylamino)ethoxy]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(OCCNCC(C)(C)C)=CC=C3C2)=C1O RKICJLSKDUSLPK-UHFFFAOYSA-N 0.000 claims description 2
- QHIUCJMWZIQBCV-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[4-(2-hydroxyethyl)piperazin-1-yl]-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(=CC=C3C2)N2CCN(CCO)CC2)=C1O QHIUCJMWZIQBCV-UHFFFAOYSA-N 0.000 claims description 2
- IOBATCZTSZQFKE-UHFFFAOYSA-N (2,4-dihydroxy-5-propan-2-ylphenyl)-[6-[2-(dimethylamino)ethoxy]-4-methyl-1,3-dihydroisoindol-2-yl]methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(C)C=C(OCCN(C)C)C=C3C2)=C1O IOBATCZTSZQFKE-UHFFFAOYSA-N 0.000 claims description 2
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- AGHRSYDXIACWAH-UHFFFAOYSA-N (3-tert-butyl-4-hydroxyphenyl)-(1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(=O)N2CC3=CC=CC=C3C2)=C1 AGHRSYDXIACWAH-UHFFFAOYSA-N 0.000 claims description 2
- NRRDDJRMRDLCEE-UHFFFAOYSA-N (3-tert-butyl-4-hydroxyphenyl)-(2,3-dihydroindol-1-yl)methanone Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(=O)N2C3=CC=CC=C3CC2)=C1 NRRDDJRMRDLCEE-UHFFFAOYSA-N 0.000 claims description 2
- DOBRSHLMCIYEEI-UHFFFAOYSA-N (4,7-difluoro-1,3-dihydroisoindol-2-yl)-(2,4-dihydroxy-5-propan-2-ylphenyl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=C(C(=CC=C3F)F)C2)=C1O DOBRSHLMCIYEEI-UHFFFAOYSA-N 0.000 claims description 2
- JGKVBQVQYZFVMN-UHFFFAOYSA-N (5-amino-1,3-dihydroisoindol-2-yl)-(2,4-dihydroxy-5-propan-2-ylphenyl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(N)=CC=C3C2)=C1O JGKVBQVQYZFVMN-UHFFFAOYSA-N 0.000 claims description 2
- OTKZPCDLOLLPPV-UHFFFAOYSA-N (5-bromo-2,4-dihydroxyphenyl)-(1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(Br)C(O)=CC(O)=C1C(=O)N1CC2=CC=CC=C2C1 OTKZPCDLOLLPPV-UHFFFAOYSA-N 0.000 claims description 2
- JUVRJNYFHAUUEF-UHFFFAOYSA-N (5-butan-2-yl-2,4-dihydroxyphenyl)-(1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(O)C(C(C)CC)=CC(C(=O)N2CC3=CC=CC=C3C2)=C1O JUVRJNYFHAUUEF-UHFFFAOYSA-N 0.000 claims description 2
- FBMKRVXJVXRCOJ-UHFFFAOYSA-N (5-chloro-1,3-dihydroisoindol-2-yl)-(2,4-dihydroxy-5-propan-2-ylphenyl)methanone Chemical compound C1=C(O)C(C(C)C)=CC(C(=O)N2CC3=CC(Cl)=CC=C3C2)=C1O FBMKRVXJVXRCOJ-UHFFFAOYSA-N 0.000 claims description 2
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| BR112014029301A2 (pt) | 2012-05-25 | 2017-07-25 | Berg Llc | métodos de tratamento de síndrome metabólica através de modulação da proteína choque térmico (hsp) 90-beta |
| EA031804B1 (ru) | 2014-02-03 | 2019-02-28 | Вайтаи Фармасьютиклз, Инк. | Дигидропирролопиридиновые ингибиторы ror-гамма |
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- 2007-10-12 EP EP07824166.8A patent/EP2073804B1/en not_active Not-in-force
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