ZA200601399B - Stable polymorph of bifeprunox mesylate - Google Patents

Stable polymorph of bifeprunox mesylate Download PDF

Info

Publication number: ZA200601399B
Authority: ZA; South Africa
Prior art keywords: biphenyl; crystalline polymorph; piperazinyl; yimethyl; benzoxazolone
Prior art date: 2003-08-18

Application number

ZA200601399A

Other languages

English (en)

Inventor

Zwier Klaas

Eijgendaal Irene

Klein Gerrit

Ter-Amstel Van Maria J L Horst

Original Assignee

Solvay Pharmaceutical B V

Priority date (The priority date 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 date listed.)

2003-08-18

Filing date

2006-02-16

Publication date

2007-04-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34924088&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200601399(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-02-16 Application filed by Solvay Pharmaceutical B V filed Critical Solvay Pharmaceutical B V

2007-04-25 Publication of ZA200601399B publication Critical patent/ZA200601399B/en

Links

ONWKHSGOYGLGPO-UHFFFAOYSA-N methanesulfonic acid;7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3h-1,3-benzoxazol-2-one Chemical compound CS(O)(=O)=O.C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 ONWKHSGOYGLGPO-UHFFFAOYSA-N 0.000 title claims description 36
239000000203 mixture Substances 0.000 claims description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
239000013078 crystal Substances 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
239000004305 biphenyl Substances 0.000 claims description 9
238000002844 melting Methods 0.000 claims description 8
230000008018 melting Effects 0.000 claims description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
238000010521 absorption reaction Methods 0.000 claims description 7
238000002329 infrared spectrum Methods 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
229940079832 sodium starch glycolate Drugs 0.000 claims description 7
239000008109 sodium starch glycolate Substances 0.000 claims description 7
229920003109 sodium starch glycolate Polymers 0.000 claims description 7
229920000168 Microcrystalline cellulose Polymers 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 6
235000019813 microcrystalline cellulose Nutrition 0.000 claims description 6
239000008108 microcrystalline cellulose Substances 0.000 claims description 6
229940016286 microcrystalline cellulose Drugs 0.000 claims description 6
229940045902 sodium stearyl fumarate Drugs 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 5
239000004471 Glycine Substances 0.000 claims description 5
229960001021 lactose monohydrate Drugs 0.000 claims description 5
235000010290 biphenyl Nutrition 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
238000000634 powder X-ray diffraction Methods 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
238000002441 X-ray diffraction Methods 0.000 claims description 3
238000005102 attenuated total reflection Methods 0.000 claims description 3
-1 lactulose monohydrate Chemical class 0.000 claims description 3
239000000377 silicon dioxide Substances 0.000 claims description 3
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
229960001375 lactose Drugs 0.000 claims description 2
239000008101 lactose Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
230000001747 exhibiting effect Effects 0.000 claims 6
208000015114 central nervous system disease Diseases 0.000 claims 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
238000012926 crystallographic analysis Methods 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229960000511 lactulose Drugs 0.000 claims 1
PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 claims 1
201000000980 schizophrenia Diseases 0.000 claims 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 75
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 19
238000003756 stirring Methods 0.000 description 14
239000007787 solid Substances 0.000 description 11
238000010926 purge Methods 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 5
238000006073 displacement reaction Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
229960004592 isopropanol Drugs 0.000 description 4
238000012986 modification Methods 0.000 description 4
230000004048 modification Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
CLCPWTXGFUIRJE-UHFFFAOYSA-N 7-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=CC2=C1OC(=O)N2 CLCPWTXGFUIRJE-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229950009087 bifeprunox Drugs 0.000 description 3
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
RSCLKRDPCPYTGC-UHFFFAOYSA-N 156016-33-0 Chemical compound CC(=O)NC1=CC(Cl)=CC([N+]([O-])=O)=C1O RSCLKRDPCPYTGC-UHFFFAOYSA-N 0.000 description 2
MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005384 cross polarization magic-angle spinning Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229940127557 pharmaceutical product Drugs 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000005855 radiation Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
STFSJTPVIIDAQX-LTRPLHCISA-M sodium;(e)-4-octadecoxy-4-oxobut-2-enoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C([O-])=O STFSJTPVIIDAQX-LTRPLHCISA-M 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
RTFPTPXBTIUISM-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylbenzene Chemical group BrCC1=CC=CC(C=2C=CC=CC=2)=C1 RTFPTPXBTIUISM-UHFFFAOYSA-N 0.000 description 1
SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
CRZGVTHVMCEWRC-UHFFFAOYSA-N 5-chloro-7-nitro-3h-1,3-benzoxazol-2-one Chemical compound [O-][N+](=O)C1=CC(Cl)=CC2=C1OC(=O)N2 CRZGVTHVMCEWRC-UHFFFAOYSA-N 0.000 description 1
CMFIWMWBTZQTQH-IDTAVKCVSA-N 9-[(2r,3r,4s,5s)-3,4-dihydroxy-5-(2-methylpropylsulfanylmethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CSCC(C)C)O[C@H]1N1C(NC=NC2=O)=C2N=C1 CMFIWMWBTZQTQH-IDTAVKCVSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001550224 Apha Species 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
229910016523 CuKa Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910000661 Mercury cadmium telluride Inorganic materials 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
MCMSPRNYOJJPIZ-UHFFFAOYSA-N cadmium;mercury;tellurium Chemical compound [Cd]=[Te]=[Hg] MCMSPRNYOJJPIZ-UHFFFAOYSA-N 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
238000005564 crystal structure determination Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000006260 foam Substances 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
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
HGDAFIJKXCFHPG-UHFFFAOYSA-N n-(5-chloro-2-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1O HGDAFIJKXCFHPG-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000010951 particle size reduction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000012207 quantitative assay Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000004467 single crystal X-ray diffraction Methods 0.000 description 1
238000000373 single-crystal X-ray diffraction data Methods 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychology (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicinal Preparation (AREA)

ZA200601399A 2003-08-18 2006-02-16 Stable polymorph of bifeprunox mesylate ZA200601399B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP03102573		2003-08-18

Publications (1)

Publication Number	Publication Date
ZA200601399B true ZA200601399B (en)	2007-04-25

Family

ID=34924088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200601399A ZA200601399B (en)	2003-08-18	2006-02-16	Stable polymorph of bifeprunox mesylate

Country Status (26)

Country	Link
EP (1)	EP1656358B1 (sr)
JP (1)	JP2007502802A (sr)
CN (1)	CN100422159C (sr)
AR (1)	AR045362A1 (sr)
AT (1)	ATE499348T1 (sr)
AU (1)	AU2004265104B2 (sr)
BR (1)	BRPI0413617A (sr)
CA (1)	CA2536149C (sr)
DE (1)	DE602004031534D1 (sr)
DK (1)	DK1656358T3 (sr)
EA (1)	EA008182B1 (sr)
ES (1)	ES2361508T3 (sr)
IS (1)	IS8279A (sr)
ME (1)	MEP37108A (sr)
MX (1)	MXPA06001881A (sr)
MY (1)	MY139462A (sr)
NO (1)	NO20061265L (sr)
NZ (1)	NZ545415A (sr)
PL (1)	PL1656358T3 (sr)
PT (1)	PT1656358E (sr)
RS (1)	RS20060113A (sr)
SI (1)	SI1656358T1 (sr)
TW (1)	TWI336695B (sr)
UA (1)	UA85562C2 (sr)
WO (1)	WO2005016898A2 (sr)
ZA (1)	ZA200601399B (sr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7423040B2 (en) *	2005-02-18	2008-09-09	Irene Eijgendaal	Stable crystalline form of bifeprunox mesylate, dosage forms thereof and methods for using same
WO2007144422A2 (en) *	2006-06-16	2007-12-21	Solvay Pharmaceuticals B.V.	Combination preparations comprising bifeprunox and l-dopa
EP2059245A1 (en)	2006-08-31	2009-05-20	Solvay Pharmaceuticals B.V.	Bifeprunox doses for treating schizophrenia
WO2011023796A1 (en)	2009-08-31	2011-03-03	Abbott Healthcare Products B.V.	Bifeprunox for treating addiction
US9675101B2 (en)	2013-03-15	2017-06-13	Whirlpool Corporation	High performance adjustable juicer with whole foods feed chute

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT889889E (pt) *	1996-03-29	2007-01-31	Duphar Int Res	Composto de piperazina e piperidina
IL127497A (en) *	1997-12-18	2002-07-25	Pfizer Prod Inc	Medicinal products containing piperazinyl-heterocyclic compounds for the treatment of psychiatric disorders
AU2003999A (en) *	1997-12-19	1999-07-12	Advanced Research And Technology Institute, Inc.	Modulators of ryanodine receptors comprising 2-(aryl)-4,7-dioxobenzothiazoles and analogues thereof
AR034206A1 (es) *	2001-02-16	2004-02-04	Solvay Pharm Bv	Un procedimiento para la preparacion de mesilatos de derivados de piperazina y dichos mesilatos

2004
- 2004-08-13 AR ARP040102906A patent/AR045362A1/es unknown
- 2004-08-16 TW TW093124532A patent/TWI336695B/zh not_active IP Right Cessation
- 2004-08-16 MY MYPI20043324A patent/MY139462A/en unknown
- 2004-08-18 UA UAA200602994A patent/UA85562C2/ru unknown
- 2004-08-18 CA CA2536149A patent/CA2536149C/en not_active Expired - Fee Related
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- 2004-08-18 DE DE602004031534T patent/DE602004031534D1/de not_active Expired - Lifetime
- 2004-08-18 NZ NZ545415A patent/NZ545415A/en not_active IP Right Cessation
- 2004-08-18 EA EA200600442A patent/EA008182B1/ru not_active IP Right Cessation
- 2004-08-18 BR BRPI0413617-9A patent/BRPI0413617A/pt not_active IP Right Cessation
- 2004-08-18 PL PL04766517T patent/PL1656358T3/pl unknown
- 2004-08-18 SI SI200431663T patent/SI1656358T1/sl unknown
- 2004-08-18 PT PT04766517T patent/PT1656358E/pt unknown
- 2004-08-18 JP JP2006523633A patent/JP2007502802A/ja active Pending
- 2004-08-18 ES ES04766517T patent/ES2361508T3/es not_active Expired - Lifetime
- 2004-08-18 AU AU2004265104A patent/AU2004265104B2/en not_active Ceased
- 2004-08-18 CN CNB2004800235660A patent/CN100422159C/zh not_active Expired - Fee Related
- 2004-08-18 AT AT04766517T patent/ATE499348T1/de active
- 2004-08-18 MX MXPA06001881A patent/MXPA06001881A/es active IP Right Grant
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- 2004-08-18 ME MEP-371/08A patent/MEP37108A/xx unknown
- 2004-08-18 DK DK04766517.9T patent/DK1656358T3/da active
2006
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- 2006-02-16 ZA ZA200601399A patent/ZA200601399B/en unknown
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Also Published As

Publication number	Publication date
AR045362A1 (es)	2005-10-26
PT1656358E (pt)	2011-05-12
TWI336695B (en)	2011-02-01
ES2361508T3 (es)	2011-06-17
MY139462A (en)	2009-10-30
EA200600442A1 (ru)	2006-08-25
EA008182B1 (ru)	2007-04-27
WO2005016898A3 (en)	2005-04-07
MEP37108A (en)	2011-02-10
RS20060113A (sr)	2008-09-29
JP2007502802A (ja)	2007-02-15
CA2536149A1 (en)	2005-02-24
EP1656358B1 (en)	2011-02-23
IS8279A (is)	2006-01-31
MXPA06001881A (es)	2006-05-17
EP1656358A2 (en)	2006-05-17
TW200513462A (en)	2005-04-16
AU2004265104B2 (en)	2009-06-04
CN100422159C (zh)	2008-10-01
WO2005016898B1 (en)	2005-05-19
DE602004031534D1 (de)	2011-04-07
BRPI0413617A (pt)	2006-10-17
SI1656358T1 (sl)	2011-06-30
AU2004265104A1 (en)	2005-02-24
PL1656358T3 (pl)	2011-07-29
NZ545415A (en)	2009-11-27
ATE499348T1 (de)	2011-03-15
CA2536149C (en)	2011-03-22
UA85562C2 (en)	2009-02-10
WO2005016898A2 (en)	2005-02-24
CN1835935A (zh)	2006-09-20
NO20061265L (no)	2006-05-09
DK1656358T3 (da)	2011-05-30

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