CN102584673A - N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的多晶型物 - Google Patents
N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的多晶型物 Download PDFInfo
- Publication number
- CN102584673A CN102584673A CN2012100147350A CN201210014735A CN102584673A CN 102584673 A CN102584673 A CN 102584673A CN 2012100147350 A CN2012100147350 A CN 2012100147350A CN 201210014735 A CN201210014735 A CN 201210014735A CN 102584673 A CN102584673 A CN 102584673A
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- Prior art keywords
- methyl
- ethyl
- phenyl
- amino
- indole
- 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.)
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Links
- 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 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 124
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 124
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 124
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 95
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical class C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UWTATZPHSA-M (R)-lactate Chemical compound C[C@@H](O)C([O-])=O JVTAAEKCZFNVCJ-UWTATZPHSA-M 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 abstract description 73
- 238000000034 method Methods 0.000 abstract description 21
- 230000008569 process Effects 0.000 abstract description 5
- 239000012458 free base Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- 239000003513 alkali Substances 0.000 description 51
- 238000005755 formation reaction Methods 0.000 description 50
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 45
- 235000019441 ethanol Nutrition 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 31
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- 238000003756 stirring Methods 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 24
- 238000000926 separation method Methods 0.000 description 24
- 150000004682 monohydrates Chemical class 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- 229960000448 lactic acid Drugs 0.000 description 20
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 229940095064 tartrate Drugs 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 229960000658 sumatriptan succinate Drugs 0.000 description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000004310 lactic acid Substances 0.000 description 9
- 235000014655 lactic acid Nutrition 0.000 description 9
- 229940049920 malate Drugs 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
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- -1 thinner Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
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- 150000001875 compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- BSYNFGPFPYSTTM-UHFFFAOYSA-N 2-hydroxypropanoic acid;hydrate Chemical compound O.CC(O)C(O)=O BSYNFGPFPYSTTM-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 102000003964 Histone deacetylase Human genes 0.000 description 3
- 108090000353 Histone deacetylase Proteins 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
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- 150000007524 organic acids Chemical class 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
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- 239000003981 vehicle Substances 0.000 description 3
- STGNLGBPLOVYMA-MAZDBSFSSA-N (E)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O STGNLGBPLOVYMA-MAZDBSFSSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 238000007614 solvation Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000005144 thermotropism Effects 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-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
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000005949 negative regulation of histone deacetylation Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960003708 sumatriptan Drugs 0.000 description 1
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Images
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
- C07D207/18—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
-
- 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
- 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
-
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epidemiology (AREA)
Abstract
Description
Claims (3)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80451706P | 2006-06-12 | 2006-06-12 | |
US60/804,517 | 2006-06-12 | ||
US88322407P | 2007-01-03 | 2007-01-03 | |
US60/883,224 | 2007-01-03 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2007800216589A Division CN101641328B (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的多晶型物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102584673A true CN102584673A (zh) | 2012-07-18 |
CN102584673B CN102584673B (zh) | 2014-08-06 |
Family
ID=38832679
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201210014735.0A Active CN102584673B (zh) | 2006-06-12 | 2007-06-07 | N-羟基-3-[4-[[[2-(2-甲基-1h-吲哚-3-基)乙基]氨基]甲基]苯基]-2e-2-丙烯酰胺的多晶型物 |
Country Status (29)
Country | Link |
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US (1) | US7989494B2 (zh) |
EP (2) | EP2409967A1 (zh) |
JP (3) | JP2009540006A (zh) |
KR (4) | KR20140142335A (zh) |
CN (1) | CN102584673B (zh) |
AR (1) | AR061297A1 (zh) |
AU (1) | AU2007257881B2 (zh) |
BR (1) | BRPI0712993A2 (zh) |
CA (1) | CA2650263A1 (zh) |
CL (1) | CL2007001689A1 (zh) |
CR (1) | CR10440A (zh) |
EA (1) | EA017984B1 (zh) |
EC (1) | ECSP088976A (zh) |
GE (1) | GEP20115175B (zh) |
GT (1) | GT200800280A (zh) |
IL (1) | IL195015A (zh) |
MA (1) | MA30511B1 (zh) |
ME (1) | ME00529B (zh) |
MX (1) | MX2008015900A (zh) |
MY (1) | MY149337A (zh) |
NI (1) | NI200800306A (zh) |
NO (1) | NO20090135L (zh) |
PE (1) | PE20080852A1 (zh) |
PH (1) | PH12012501725A1 (zh) |
SM (1) | SMP200900001B (zh) |
TN (1) | TNSN08495A1 (zh) |
TW (2) | TWI453196B (zh) |
UY (1) | UY30406A1 (zh) |
WO (1) | WO2007146716A2 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017032281A1 (zh) * | 2015-08-21 | 2017-03-02 | 苏州晶云药物科技有限公司 | 帕比司他乳酸盐的新晶型 |
CN106866491A (zh) * | 2015-12-10 | 2017-06-20 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ⅰ及其制备方法和用途 |
CN106866492A (zh) * | 2015-12-10 | 2017-06-20 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ii及其制备方法和用途 |
Families Citing this family (9)
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BRPI0712771A2 (pt) * | 2006-06-12 | 2012-09-25 | Novartis Ag | sais de n-hidróxi-3-[4-[[[2-(2-metil-1h-indol-3-il)etil]amino] metil]fenil]-2e-2-propenamida |
AU2008204928B2 (en) * | 2007-01-10 | 2011-03-31 | Novartis Ag | Formulations of deacetylase inhibitors |
WO2018092151A1 (en) * | 2016-11-21 | 2018-05-24 | Msn Laboratories Private Limited, R&D Center | Process for the preparation of 2-(e)-n-hydroxy-3-[4-[[[2-(2-methyl-1h-indol-3-yl) ethyl]amino]methyl]phenyl]-2-propenamide 2-hydroxypropanoic acid (1:1) and its polymorphs thereof |
WO2018163114A1 (en) * | 2017-03-10 | 2018-09-13 | Shilpa Medicare Limited | Amorphous panobinostat and its lactate salt |
US10537585B2 (en) | 2017-12-18 | 2020-01-21 | Dexcel Pharma Technologies Ltd. | Compositions comprising dexamethasone |
JP7409383B2 (ja) * | 2019-08-20 | 2024-01-09 | 小野薬品工業株式会社 | S1p5受容体作動活性を有する化合物の塩および結晶形 |
GB201913124D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
GB201913122D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
GB201913121D0 (en) | 2019-09-11 | 2019-10-23 | Seald As | Compositions and methods for treatment of cholangiocarcinoma |
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Publication number | Priority date | Publication date | Assignee | Title |
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PE20020354A1 (es) * | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
US7402603B2 (en) | 2001-11-06 | 2008-07-22 | Novartis Ag | Cyclooxygenase-2 inhibitor/histone deacetylase inhibitor combination |
WO2003048774A1 (en) | 2001-12-07 | 2003-06-12 | Novartis Ag | Use of alpha-tubulin acetylation levels as a biomarker for protein deacetylase inhibitors |
MXPA05012464A (es) | 2003-05-21 | 2006-01-30 | Novartis Ag | Combinacion de inhibidores de deacetilasa de histona con agentes quimioterapeuticos. |
WO2005013958A1 (en) | 2003-08-07 | 2005-02-17 | Novartis Ag | Histone deacetylase inhibitors as immunosuppressants |
CA2537991A1 (en) | 2003-09-23 | 2005-03-31 | Novartis Ag | Combination of a vegf receptor inhibitor with a chemotherapeutic agent |
BRPI0712771A2 (pt) | 2006-06-12 | 2012-09-25 | Novartis Ag | sais de n-hidróxi-3-[4-[[[2-(2-metil-1h-indol-3-il)etil]amino] metil]fenil]-2e-2-propenamida |
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WO2017032281A1 (zh) * | 2015-08-21 | 2017-03-02 | 苏州晶云药物科技有限公司 | 帕比司他乳酸盐的新晶型 |
CN106866491A (zh) * | 2015-12-10 | 2017-06-20 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ⅰ及其制备方法和用途 |
CN106866492A (zh) * | 2015-12-10 | 2017-06-20 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ii及其制备方法和用途 |
CN106866492B (zh) * | 2015-12-10 | 2021-11-26 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ii及其制备方法和用途 |
CN106866491B (zh) * | 2015-12-10 | 2021-12-10 | 江苏豪森药业集团有限公司 | 帕比司他乳酸盐晶型ⅰ及其制备方法和用途 |
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