JP2008536836A - 抗がん剤の調製方法 - Google Patents
抗がん剤の調製方法 Download PDFInfo
- Publication number
- JP2008536836A JP2008536836A JP2008505592A JP2008505592A JP2008536836A JP 2008536836 A JP2008536836 A JP 2008536836A JP 2008505592 A JP2008505592 A JP 2008505592A JP 2008505592 A JP2008505592 A JP 2008505592A JP 2008536836 A JP2008536836 A JP 2008536836A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- toluene
- hours
- temperature
- anastrozole
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000002246 antineoplastic agent Substances 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 213
- 238000000034 method Methods 0.000 claims abstract description 120
- 239000002904 solvent Substances 0.000 claims abstract description 66
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 claims abstract description 63
- 229960002932 anastrozole Drugs 0.000 claims abstract description 62
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 47
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 33
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 33
- ZEQDWUSZTQOXGL-UHFFFAOYSA-N 2-(2-methylpropyl)benzonitrile Chemical compound CC(C)CC1=CC=CC=C1C#N ZEQDWUSZTQOXGL-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000005997 bromomethyl group Chemical group 0.000 claims abstract description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 26
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 10
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 69
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 49
- 239000000725 suspension Substances 0.000 claims description 40
- 239000012074 organic phase Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000008346 aqueous phase Substances 0.000 claims description 27
- 229930195733 hydrocarbon Natural products 0.000 claims description 26
- 150000002430 hydrocarbons Chemical class 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000012296 anti-solvent Substances 0.000 claims description 19
- 239000012535 impurity Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 239000011259 mixed solution Substances 0.000 claims description 13
- 238000005893 bromination reaction Methods 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 108010037444 diisopropylglutathione ester Proteins 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 230000031709 bromination Effects 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- LRKBACPCJTXJNF-UHFFFAOYSA-N 2-propan-2-ylbenzonitrile Chemical compound CC(C)C1=CC=CC=C1C#N LRKBACPCJTXJNF-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- UHMBCUNKPNNBSD-UHFFFAOYSA-N 2-[3-(2-cyanopropan-2-yl)-5-(1,2,4-triazol-4-ylmethyl)phenyl]-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2C=NN=C2)=C1 UHMBCUNKPNNBSD-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 2
- SJECEXNMZXMXNE-UHFFFAOYSA-N 2-[3-(2-cyanopropan-2-yl)-5-methylphenyl]-2-methylpropanenitrile Chemical compound CC1=CC(C(C)(C)C#N)=CC(C(C)(C)C#N)=C1 SJECEXNMZXMXNE-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 239000003480 eluent Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- -1 (2-cyclopropanol) toluene Chemical compound 0.000 description 4
- 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 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 230000002051 biphasic effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 239000012455 biphasic mixture Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KKLJTVADLAPVOW-UHFFFAOYSA-N 3-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)CN=NC(C)(C)C#N KKLJTVADLAPVOW-UHFFFAOYSA-N 0.000 description 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
- 229940122815 Aromatase inhibitor Drugs 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66913205P | 2005-04-06 | 2005-04-06 | |
| US69452805P | 2005-06-27 | 2005-06-27 | |
| PCT/US2006/013140 WO2006108155A2 (en) | 2005-04-06 | 2006-04-06 | Process for the preparation of anastrozole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008536836A true JP2008536836A (ja) | 2008-09-11 |
| JP2008536836A5 JP2008536836A5 (enExample) | 2009-12-10 |
Family
ID=36694325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008505592A Pending JP2008536836A (ja) | 2005-04-06 | 2006-04-06 | 抗がん剤の調製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7692025B2 (enExample) |
| EP (2) | EP2172449A3 (enExample) |
| JP (1) | JP2008536836A (enExample) |
| KR (1) | KR20080000621A (enExample) |
| CA (1) | CA2601649A1 (enExample) |
| IL (1) | IL184944A0 (enExample) |
| MX (1) | MX2007012394A (enExample) |
| WO (1) | WO2006108155A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006108155A2 (en) * | 2005-04-06 | 2006-10-12 | Sicor, Inc. | Process for the preparation of anastrozole |
| AR061016A1 (es) * | 2006-05-19 | 2008-07-30 | Synthon Bv | Proceso para la purificacion de anastrozol |
| WO2007141799A1 (en) * | 2006-06-05 | 2007-12-13 | Cadila Healthcare Limited | A process for preparing pure anastrozole |
| US7989636B2 (en) * | 2006-10-17 | 2011-08-02 | Cipla Limited | Process for the preparation of pure anastrozole |
| WO2009010991A2 (en) * | 2007-07-17 | 2009-01-22 | Ind-Swift Laboratories Limited | Purification process to prepare highly pure anastrozole |
| EP2343278A1 (en) | 2010-01-07 | 2011-07-13 | Hexal AG | A process for preparing trisubstituted phenyl derivatives comprising a (1H-1,2,4-triazol-1-yl)alkyl group |
| CN106083748B (zh) * | 2016-06-21 | 2019-08-16 | 扬子江药业集团江苏海慈生物药业有限公司 | 一种阿那曲唑的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6419067A (en) * | 1987-06-16 | 1989-01-23 | Ici Plc | (substituted-aralkyl) heterocyclic compound, manufacture, and pharmacological and veteriary composition having aromatase inhibition |
| JPH07138234A (ja) * | 1993-11-11 | 1995-05-30 | Kureha Chem Ind Co Ltd | アゾリルメチルシクロアルカノール誘導体の製造方法 |
| JP2002541143A (ja) * | 1999-03-30 | 2002-12-03 | ゲデッケ・ゲーエムベーハー | 炭酸セシウムの存在下における活性芳香族化合物によるアザ複素環化合物のアリール化方法 |
Family Cites Families (19)
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| WO2005089511A2 (en) | 2004-03-19 | 2005-09-29 | Transform Pharmaceuticals, Inc. | Novel pharmaceutical forms, and methods of making and using the same |
| WO2005105762A1 (en) * | 2004-05-05 | 2005-11-10 | Natco Pharma Limited | Improved process for the preparation of high purity anastrozole |
| GB0412492D0 (en) | 2004-06-04 | 2004-07-07 | Sterix Ltd | Compound |
| US20060035950A1 (en) * | 2004-08-09 | 2006-02-16 | Mohammed Alnabari | Novel processes for preparing substantially pure anastrozole |
| US20060189670A1 (en) | 2005-02-22 | 2006-08-24 | Glenmark Pharmaceuticals Limited | Process for the preparation of anastrozole and intermediates thereof |
| EP1705168A1 (en) * | 2005-03-21 | 2006-09-27 | Helm AG | Improved process for side-chain bromination of alkyl-benzenes |
| WO2006108155A2 (en) | 2005-04-06 | 2006-10-12 | Sicor, Inc. | Process for the preparation of anastrozole |
| CN101233100A (zh) | 2005-06-27 | 2008-07-30 | 西科尔公司 | 阿那曲唑中间体的杂质及其应用 |
| WO2007054963A2 (en) | 2005-09-30 | 2007-05-18 | Cadila Healthcare Limited | A process for the preparation of pure anastrozole |
| WO2007039913A1 (en) * | 2005-10-05 | 2007-04-12 | Usv Limited | Process for the preparation of 2,2’-[5-(1,2,4-triazole-1-ylmethyl) -1,3-phenylene] di (2-methylpropionitrile). |
| WO2007039919A1 (en) | 2005-10-06 | 2007-04-12 | Natco Pharma Limited | Crystalline forms of anastrozole |
| US20070100148A1 (en) | 2005-10-31 | 2007-05-03 | Veerender Murki | Process for preparing anastrozole |
| EP1994014A4 (en) | 2006-03-10 | 2010-01-20 | Shilpa Medicare Ltd | IMPROVED PROCESS FOR HIGH-PURITY ANASTROZOL |
| AR061016A1 (es) | 2006-05-19 | 2008-07-30 | Synthon Bv | Proceso para la purificacion de anastrozol |
| WO2007141799A1 (en) | 2006-06-05 | 2007-12-13 | Cadila Healthcare Limited | A process for preparing pure anastrozole |
| FR2904821B1 (fr) | 2006-08-09 | 2009-02-20 | Air Liquide | Procede de purification d'hydrogene |
| WO2008034644A2 (en) | 2006-09-22 | 2008-03-27 | Synthon B.V. | Process for making anastrozole |
| US7989636B2 (en) | 2006-10-17 | 2011-08-02 | Cipla Limited | Process for the preparation of pure anastrozole |
| US20080177081A1 (en) * | 2007-01-19 | 2008-07-24 | Formosa Laboratories, Inc. | Process for Preparation of Anastrozole |
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- 2006-04-06 KR KR1020077024768A patent/KR20080000621A/ko not_active Ceased
- 2006-04-06 EP EP09174323A patent/EP2172449A3/en not_active Withdrawn
- 2006-04-06 MX MX2007012394A patent/MX2007012394A/es unknown
- 2006-04-06 JP JP2008505592A patent/JP2008536836A/ja active Pending
- 2006-04-06 US US11/400,639 patent/US7692025B2/en not_active Expired - Fee Related
- 2006-04-06 EP EP06740751A patent/EP1751121A2/en not_active Withdrawn
- 2006-04-06 CA CA002601649A patent/CA2601649A1/en not_active Abandoned
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2007
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2009
- 2009-11-17 US US12/592,066 patent/US20100099888A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| US20060276657A1 (en) | 2006-12-07 |
| CA2601649A1 (en) | 2006-10-12 |
| MX2007012394A (es) | 2007-11-07 |
| KR20080000621A (ko) | 2008-01-02 |
| IL184944A0 (en) | 2007-12-03 |
| EP1751121A2 (en) | 2007-02-14 |
| US7692025B2 (en) | 2010-04-06 |
| WO2006108155A2 (en) | 2006-10-12 |
| EP2172449A2 (en) | 2010-04-07 |
| WO2006108155A3 (en) | 2006-11-23 |
| EP2172449A3 (en) | 2011-06-22 |
| US20100099888A1 (en) | 2010-04-22 |
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