TWI395734B - 製造ｎ-羥基-３-〔４-〔〔〔２-（２-甲基-１ｈ-吲哚-３-基）乙基〕胺基〕甲基〕苯基〕-２ｅ-２-丙烯醯胺之方法及用於該方法之起始物質 - Google Patents
製造ｎ-羥基-３-〔４-〔〔〔２-（２-甲基-１ｈ-吲哚-３-基）乙基〕胺基〕甲基〕苯基〕-２ｅ-２-丙烯醯胺之方法及用於該方法之起始物質 Download PDFInfo
- Publication number
- TWI395734B TWI395734B TW096120985A TW96120985A TWI395734B TW I395734 B TWI395734 B TW I395734B TW 096120985 A TW096120985 A TW 096120985A TW 96120985 A TW96120985 A TW 96120985A TW I395734 B TWI395734 B TW I395734B
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- Prior art keywords
- methyl
- mixture
- phenyl
- temperature
- sub
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 112
- 239000007858 starting material Substances 0.000 title description 8
- FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 239000000725 suspension Substances 0.000 claims description 51
- 239000011541 reaction mixture Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- CPVSLHQIPGTMLH-UHFFFAOYSA-N 2-(2-methyl-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=C(C)NC2=C1 CPVSLHQIPGTMLH-UHFFFAOYSA-N 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000010438 heat treatment Methods 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 16
- 239000012279 sodium borohydride Substances 0.000 claims description 16
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 16
- 150000002466 imines Chemical class 0.000 claims description 13
- -1 N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propene oxime Chemical class 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- AXNRBGTYILEHJU-SNAWJCMRSA-N Cc1[nH]c2ccccc2c1CCNCc3ccc(\C=C\CNO)cc3 Chemical compound Cc1[nH]c2ccccc2c1CCNCc3ccc(\C=C\CNO)cc3 AXNRBGTYILEHJU-SNAWJCMRSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- 238000010899 nucleation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 18
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XVXVAVCOKYEXMZ-ZHACJKMWSA-N (e)-3-[4-[[2-(2-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enoic acid Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(O)=O)C=C1 XVXVAVCOKYEXMZ-ZHACJKMWSA-N 0.000 description 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 compound 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 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 238000004896 high resolution mass spectrometry Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000003964 Histone deacetylase Human genes 0.000 description 2
- 108090000353 Histone deacetylase Proteins 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- HJNBYBRJNPEZPN-UHFFFAOYSA-N C1(=CC=CC=C1)NN.CC1=C(CCN)C2=CC=CC=C2N1 Chemical compound C1(=CC=CC=C1)NN.CC1=C(CCN)C2=CC=CC=C2N1 HJNBYBRJNPEZPN-UHFFFAOYSA-N 0.000 description 1
- 229940122964 Deacetylase inhibitor Drugs 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- IHMIXLHARPEFMC-ZZXKWVIFSA-N N-[2-(2-methyl-1H-indol-3-yl)ethyl]-N-[[4-[(E)-prop-1-enyl]phenyl]methyl]hydroxylamine Chemical compound ON(CCC1=C(NC2=CC=CC=C12)C)CC1=CC=C(C=C1)/C=C/C IHMIXLHARPEFMC-ZZXKWVIFSA-N 0.000 description 1
- FPOHNWQLNRZRFC-UHFFFAOYSA-N N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]-2-propenamide Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(C=CC(=O)NO)C=C1 FPOHNWQLNRZRFC-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002443 hydroxylamines Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CCRIVCWOXSIYEP-UHFFFAOYSA-N methyl prop-2-enoate;hydrochloride Chemical compound Cl.COC(=O)C=C CCRIVCWOXSIYEP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80452706P | 2006-06-12 | 2006-06-12 | |
| US86787806P | 2006-11-30 | 2006-11-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200815345A TW200815345A (en) | 2008-04-01 |
| TWI395734B true TWI395734B (zh) | 2013-05-11 |
Family
ID=38832681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096120985A TWI395734B (zh) | 2006-06-12 | 2007-06-11 | 製造ｎ-羥基-３-〔４-〔〔〔２-（２-甲基-１ｈ-吲哚-３-基）乙基〕胺基〕甲基〕苯基〕-２ｅ-２-丙烯醯胺之方法及用於該方法之起始物質 |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US20090306405A1 (show.php) |
| EP (2) | EP2032533B8 (show.php) |
| JP (2) | JP5431926B2 (show.php) |
| KR (2) | KR101493530B1 (show.php) |
| CN (4) | CN102167678B (show.php) |
| AR (1) | AR061296A1 (show.php) |
| AU (1) | AU2007257883B2 (show.php) |
| BR (1) | BRPI0712847A2 (show.php) |
| CA (1) | CA2653657C (show.php) |
| CL (2) | CL2007001691A1 (show.php) |
| DK (1) | DK2032533T3 (show.php) |
| EC (1) | ECSP088978A (show.php) |
| ES (2) | ES2553255T3 (show.php) |
| GT (1) | GT200800282A (show.php) |
| HR (1) | HRP20130798T1 (show.php) |
| IL (2) | IL195211A (show.php) |
| IN (1) | IN2015DN00910A (show.php) |
| JO (1) | JO2900B1 (show.php) |
| MA (1) | MA30513B1 (show.php) |
| MX (2) | MX2008015898A (show.php) |
| MY (1) | MY147576A (show.php) |
| NO (1) | NO341870B1 (show.php) |
| NZ (1) | NZ572707A (show.php) |
| PE (2) | PE20120221A1 (show.php) |
| PL (1) | PL2032533T3 (show.php) |
| PT (1) | PT2032533E (show.php) |
| RU (1) | RU2448090C2 (show.php) |
| TN (1) | TNSN08507A1 (show.php) |
| TW (1) | TWI395734B (show.php) |
| WO (1) | WO2007146718A2 (show.php) |
| ZA (1) | ZA200809490B (show.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT202000004075A1 (it) | 2020-02-27 | 2021-08-27 | Flamma Spa | Processo per la preparazione di panobinostat |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022577A2 (en) * | 2000-09-01 | 2002-03-21 | Novartis Ag | Hydroxamate derivatives useful as deacetylase inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB146260A (en) | 1918-07-11 | 1921-08-11 | Elektro Osmose Ag | A process for preparing proteids charged with immune substances |
| GB8531612D0 (en) * | 1985-12-23 | 1986-02-05 | Beecham Wuelfing Gmbh & Co Kg | Compounds |
| AU2002237261A1 (en) | 2001-01-09 | 2002-07-24 | Novartis Pharma Gmbh | Rapid method for screening compounds for in vivo activity |
| NZ544689A (en) | 2001-11-06 | 2007-08-31 | Novartis Ag | Cyclooxygenase-2 inhibitor/histone deacetylase inhibitor combination |
| AU2007257882B2 (en) * | 2006-06-12 | 2011-09-08 | Secura Bio Inc. | Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide |
-
2007
- 2007-06-07 IN IN910DEN2015 patent/IN2015DN00910A/en unknown
- 2007-06-07 WO PCT/US2007/070564 patent/WO2007146718A2/en not_active Ceased
- 2007-06-07 CN CN2011100629486A patent/CN102167678B/zh active Active
- 2007-06-07 US US12/302,572 patent/US20090306405A1/en not_active Abandoned
- 2007-06-07 MX MX2008015898A patent/MX2008015898A/es active IP Right Grant
- 2007-06-07 CA CA2653657A patent/CA2653657C/en active Active
- 2007-06-07 CN CN2012103501544A patent/CN103086944A/zh active Pending
- 2007-06-07 MX MX2012002221A patent/MX366213B/es unknown
- 2007-06-07 KR KR20087030232A patent/KR101493530B1/ko not_active Expired - Fee Related
- 2007-06-07 KR KR1020147026120A patent/KR101540194B1/ko not_active Expired - Fee Related
- 2007-06-07 BR BRPI0712847-9A patent/BRPI0712847A2/pt not_active IP Right Cessation
- 2007-06-07 PL PL07784350T patent/PL2032533T3/pl unknown
- 2007-06-07 AU AU2007257883A patent/AU2007257883B2/en not_active Ceased
- 2007-06-07 CN CN2011100630820A patent/CN102174008A/zh active Pending
- 2007-06-07 EP EP07784350.6A patent/EP2032533B8/en active Active
- 2007-06-07 NZ NZ572707A patent/NZ572707A/en not_active IP Right Cessation
- 2007-06-07 ES ES11179043.2T patent/ES2553255T3/es active Active
- 2007-06-07 ES ES07784350T patent/ES2416286T3/es active Active
- 2007-06-07 PT PT77843506T patent/PT2032533E/pt unknown
- 2007-06-07 DK DK07784350.6T patent/DK2032533T3/da active
- 2007-06-07 RU RU2008151726/04A patent/RU2448090C2/ru active
- 2007-06-07 JP JP2009515575A patent/JP5431926B2/ja active Active
- 2007-06-07 EP EP11179043.2A patent/EP2394991B1/en active Active
- 2007-06-07 CN CNA2007800217257A patent/CN101466674A/zh active Pending
- 2007-06-07 HR HRP20130798TT patent/HRP20130798T1/hr unknown
- 2007-06-08 PE PE2011002097A patent/PE20120221A1/es active IP Right Grant
- 2007-06-08 AR ARP070102498A patent/AR061296A1/es unknown
- 2007-06-08 PE PE2007000720A patent/PE20080851A1/es active IP Right Grant
- 2007-06-11 TW TW096120985A patent/TWI395734B/zh not_active IP Right Cessation
- 2007-06-11 CL CL200701691A patent/CL2007001691A1/es unknown
- 2007-06-12 JO JO2007219A patent/JO2900B1/en active
-
2008
- 2008-11-06 ZA ZA200809490A patent/ZA200809490B/xx unknown
- 2008-11-10 IL IL195211A patent/IL195211A/en active IP Right Grant
- 2008-11-28 MY MYPI20084865A patent/MY147576A/en unknown
- 2008-12-05 TN TNP2008000507A patent/TNSN08507A1/en unknown
- 2008-12-10 GT GT200800282A patent/GT200800282A/es unknown
- 2008-12-12 EC EC2008008978A patent/ECSP088978A/es unknown
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002022577A2 (en) * | 2000-09-01 | 2002-03-21 | Novartis Ag | Hydroxamate derivatives useful as deacetylase inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| GRANDBERG I.I. et al.,"INDOLES I. A New Method for the Synthesis of 2-Substituted Tryptamines" , CHEMISTRY OF HETEROCYCLIC COMPOUNDS, Volume: 4, Pages: 632-633, Published: 1968。 * |
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