JP2010514796A5 - - Google Patents
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- JP2010514796A5 JP2010514796A5 JP2009544276A JP2009544276A JP2010514796A5 JP 2010514796 A5 JP2010514796 A5 JP 2010514796A5 JP 2009544276 A JP2009544276 A JP 2009544276A JP 2009544276 A JP2009544276 A JP 2009544276A JP 2010514796 A5 JP2010514796 A5 JP 2010514796A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- aryl
- formula
- aralkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 69
- -1 amino, hydroxyl Chemical group 0.000 claims description 65
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 150000004820 halides Chemical class 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 150000001408 amides Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000002825 nitriles Chemical class 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000005547 pivalate group Chemical group 0.000 claims description 7
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 4
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000004832 aryl thioethers Chemical class 0.000 claims description 3
- IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- 229940106681 chloroacetic acid Drugs 0.000 claims description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 3
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 3
- 229940013688 formic acid Drugs 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000005039 triarylmethyl group Chemical group 0.000 claims description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 3
- 229960004319 trichloroacetic acid Drugs 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- MKRZFOIRSLOYCE-UHFFFAOYSA-L zinc;methanesulfonate Chemical compound [Zn+2].CS([O-])(=O)=O.CS([O-])(=O)=O MKRZFOIRSLOYCE-UHFFFAOYSA-L 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- TVBJMUGQTNVVIW-UHFFFAOYSA-N P(O)(O)(O)=O.C1(CC1)C(=O)O Chemical compound P(O)(O)(O)=O.C1(CC1)C(=O)O TVBJMUGQTNVVIW-UHFFFAOYSA-N 0.000 claims 1
- 229910001115 Zinc-copper couple Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims 1
- CVSSUEMSGYVRDI-UHFFFAOYSA-N methanesulfonic acid zinc Chemical compound [Zn].CS(O)(=O)=O.CS(O)(=O)=O CVSSUEMSGYVRDI-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 0 C[C@]1C(CC2)(C(C)(*3)C3(C[C@@](C3CC(*)C4(*5)C5C(*)(*)CC5)C45[Mc])[C@@]23N)O[C@@]2C1N(*)C[C@@](C)C2 Chemical compound C[C@]1C(CC2)(C(C)(*3)C3(C[C@@](C3CC(*)C4(*5)C5C(*)(*)CC5)C45[Mc])[C@@]23N)O[C@@]2C1N(*)C[C@@](C)C2 0.000 description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87801806P | 2006-12-28 | 2006-12-28 | |
| US60/878,018 | 2006-12-28 | ||
| US94159607P | 2007-06-01 | 2007-06-01 | |
| US60/941,596 | 2007-06-01 | ||
| PCT/US2007/088990 WO2008083248A2 (en) | 2006-12-28 | 2007-12-27 | Cyclopamine analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010514796A JP2010514796A (ja) | 2010-05-06 |
| JP2010514796A5 true JP2010514796A5 (enExample) | 2011-02-17 |
| JP5412292B2 JP5412292B2 (ja) | 2014-02-12 |
Family
ID=39589207
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009544276A Active JP5412292B2 (ja) | 2006-12-28 | 2007-12-27 | シクロパミン類似体 |
| JP2009544277A Active JP5542448B2 (ja) | 2006-12-28 | 2007-12-27 | シクロパミン類似体の使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009544277A Active JP5542448B2 (ja) | 2006-12-28 | 2007-12-27 | シクロパミン類似体の使用方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (18) | US7812164B2 (enExample) |
| EP (4) | EP2443926A3 (enExample) |
| JP (2) | JP5412292B2 (enExample) |
| KR (2) | KR101489394B1 (enExample) |
| CN (2) | CN101677551B (enExample) |
| AR (1) | AR081107A1 (enExample) |
| AU (2) | AU2007339786B2 (enExample) |
| BR (2) | BRPI0720972B8 (enExample) |
| CA (2) | CA2674302C (enExample) |
| CL (1) | CL2007003854A1 (enExample) |
| DK (1) | DK2096917T3 (enExample) |
| ES (2) | ES2612746T3 (enExample) |
| IL (1) | IL199554B (enExample) |
| JO (1) | JO2947B1 (enExample) |
| MX (3) | MX2009007077A (enExample) |
| NO (3) | NO347310B1 (enExample) |
| NZ (2) | NZ578053A (enExample) |
| PE (1) | PE20090042A1 (enExample) |
| PL (1) | PL2096917T3 (enExample) |
| PT (1) | PT2096917E (enExample) |
| RU (2) | RU2486194C2 (enExample) |
| SG (2) | SG177930A1 (enExample) |
| TW (1) | TWI433674B (enExample) |
| WO (2) | WO2008083252A2 (enExample) |
| ZA (2) | ZA200904445B (enExample) |
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| US7964590B2 (en) | 2007-03-07 | 2011-06-21 | Infinity Discovery, Inc. | Cyclopamine lactam analogs and methods of use thereof |
| NZ579361A (en) | 2007-03-07 | 2012-04-27 | Infinity Discovery Inc | Heterocyclic cyclopamine analogs and methods of use thereof |
| US20100297118A1 (en) * | 2007-12-27 | 2010-11-25 | Macdougall John | Therapeutic Cancer Treatments |
| EP3190121B1 (en) * | 2007-12-27 | 2019-02-20 | Infinity Pharmaceuticals, Inc. | Methods for stereoselective reduction of cyclopamine 4-en-3-one derivative |
| CA2710377A1 (en) * | 2007-12-27 | 2009-07-09 | Infinity Pharmaceuticals, Inc. | Therapeutic cancer treatments |
| US20100222287A1 (en) * | 2007-12-27 | 2010-09-02 | Mcgovern Karen J | Therapeutic Cancer Treatments |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| WO2009099625A2 (en) * | 2008-02-08 | 2009-08-13 | The Board Of Regents Of The University Of Texas System | Cyclopamine tartrate salt and uses thereof |
| US20110275576A1 (en) * | 2009-01-06 | 2011-11-10 | Utah State University | Carbohydrate-Cyclopamine Conjugates as Anticancer Agents |
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| US20110065645A1 (en) * | 2009-09-10 | 2011-03-17 | The Regents Of The University Of California | Compositions and Methods for Modulating Neuron Degeneration and Neuron Guidance |
| WO2011057222A1 (en) * | 2009-11-06 | 2011-05-12 | Infinity Pharmaceuticals, Inc. | Oral formulations of a hedgehog pathway inhibitor |
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| CN103298474B (zh) | 2010-11-10 | 2016-06-29 | 无限药品股份有限公司 | 杂环化合物及其用途 |
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