CA2646368A1 - O-desmethylvenlafaxine essentiellement pure et ses procedes de preparation - Google Patents

O-desmethylvenlafaxine essentiellement pure et ses procedes de preparation Download PDF

Info

Publication number: CA2646368A1
Authority: CA; Canada
Prior art keywords: desmethylvenlafaxine; substantially pure; preparing; mixture; desmethylvenlafaxine according
Prior art date: 2006-04-17
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.): Abandoned

Application number

CA002646368A

Other languages

English (en)

Inventor

Valerie Niddam-Hildesheim

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teva Pharmaceutical Industries Ltd

Original Assignee

Individual

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.)

2006-04-17

Filing date

2007-04-17

Publication date

2007-10-25

2007-04-17 Application filed by Individual filed Critical Individual

2007-10-25 Publication of CA2646368A1 publication Critical patent/CA2646368A1/fr

Status Abandoned legal-status Critical Current

Links

KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 title claims abstract description 132
238000000034 method Methods 0.000 title claims abstract description 59
239000000203 mixture Substances 0.000 claims description 102
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 60
238000004128 high performance liquid chromatography Methods 0.000 claims description 55
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
238000004519 manufacturing process Methods 0.000 claims description 51
PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 47
229960004688 venlafaxine Drugs 0.000 claims description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 42
239000012535 impurity Substances 0.000 claims description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 36
239000003480 eluent Substances 0.000 claims description 36
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
238000003556 assay Methods 0.000 claims description 24
BHCUWXACHAFFSK-UHFFFAOYSA-N 4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenol Chemical compound C1CCCCC1(O)C(CN)C1=CC=C(O)C=C1 BHCUWXACHAFFSK-UHFFFAOYSA-N 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 22
239000000725 suspension Substances 0.000 claims description 20
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
239000003960 organic solvent Substances 0.000 claims description 17
239000000546 pharmaceutical excipient Substances 0.000 claims description 17
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
-1 C1-C8 alkyl thiolate Chemical class 0.000 claims description 15
239000000243 solution Substances 0.000 claims description 15
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
229910052979 sodium sulfide Inorganic materials 0.000 claims description 13
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
238000009835 boiling Methods 0.000 claims description 11
238000010438 heat treatment Methods 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
238000001556 precipitation Methods 0.000 claims description 8
239000002002 slurry Substances 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000001384 succinic acid Substances 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
238000004458 analytical method Methods 0.000 claims description 6
150000007944 thiolates Chemical class 0.000 claims description 6
239000012296 anti-solvent Substances 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
238000000634 powder X-ray diffraction Methods 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 4
239000007900 aqueous suspension Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
XRZRPHKMCVBSLA-UHFFFAOYSA-M sodium;dodecane-1-thiolate Chemical group [Na+].CCCCCCCCCCCC[S-] XRZRPHKMCVBSLA-UHFFFAOYSA-M 0.000 claims description 3
238000012360 testing method Methods 0.000 claims description 3
DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 claims description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
239000003921 oil Substances 0.000 claims description 2
229910052710 silicon Inorganic materials 0.000 claims description 2
239000010703 silicon Substances 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims 3
150000008041 alkali metal carbonates Chemical class 0.000 claims 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
239000011877 solvent mixture Substances 0.000 claims 2
230000001335 demethylating effect Effects 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
239000007787 solid Substances 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 23
239000008186 active pharmaceutical agent Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000007788 liquid Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
235000015165 citric acid Nutrition 0.000 description 9
239000002552 dosage form Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 8
210000003739 neck Anatomy 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000006227 byproduct Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
239000003826 tablet Substances 0.000 description 6
238000007907 direct compression Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
229940032147 starch Drugs 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229920002125 Sokalan® Polymers 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000017858 demethylation Effects 0.000 description 4
238000010520 demethylation reaction Methods 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229940014259 gelatin Drugs 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
229920000609 methyl cellulose Polymers 0.000 description 4
235000010981 methylcellulose Nutrition 0.000 description 4
239000001923 methylcellulose Substances 0.000 description 4
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 4
239000008247 solid mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
241000220479 Acacia Species 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
229920002907 Guar gum Polymers 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
235000010643 Leucaena leucocephala Nutrition 0.000 description 3
239000005913 Maltodextrin Substances 0.000 description 3
229920002774 Maltodextrin Polymers 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
235000010443 alginic acid Nutrition 0.000 description 3
229920000615 alginic acid Polymers 0.000 description 3
239000000783 alginic acid Substances 0.000 description 3
229960001126 alginic acid Drugs 0.000 description 3
150000004781 alginic acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229960001631 carbomer Drugs 0.000 description 3
229940063834 carboxymethylcellulose sodium Drugs 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
235000010417 guar gum Nutrition 0.000 description 3
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239000000314 lubricant Substances 0.000 description 3
229940035034 maltodextrin Drugs 0.000 description 3
229960002900 methylcellulose Drugs 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
229920003124 powdered cellulose Polymers 0.000 description 3
235000019814 powdered cellulose Nutrition 0.000 description 3
235000010413 sodium alginate Nutrition 0.000 description 3
239000000661 sodium alginate Substances 0.000 description 3
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239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
229940033134 talc Drugs 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound 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 GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
229920001353 Dextrin Polymers 0.000 description 2
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239000004097 EU approved flavor enhancer Substances 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
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235000011054 acetic acid Nutrition 0.000 description 2
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SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
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WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
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BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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238000002347 injection Methods 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
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229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
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WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
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229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
229940057977 zinc stearate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- 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
- A61P25/24—Antidepressants
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA002646368A 2006-04-17 2007-04-17 O-desmethylvenlafaxine essentiellement pure et ses procedes de preparation Abandoned CA2646368A1 (fr)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date	Title
US79280106P	2006-04-17	2006-04-17
US60/792,801		2006-04-17
US79673906P	2006-05-01	2006-05-01
US60/796,739		2006-05-01
US87295506P	2006-12-04	2006-12-04
US60/872,955		2006-12-04
US89916607P	2007-02-01	2007-02-01
US60/899,166		2007-02-01
US90241807P	2007-02-20	2007-02-20
US60/902,418		2007-02-20
US90398807P	2007-02-27	2007-02-27
US60/903,988		2007-02-27
PCT/US2007/009558 WO2007120923A1 (fr)	2006-04-17	2007-04-17	O-desméthylvenlafaxine essentiellement pure et ses procédés de préparation

Publications (1)

Publication Number	Publication Date
CA2646368A1 true CA2646368A1 (fr)	2007-10-25

Family

ID=39750904

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002646368A Abandoned CA2646368A1 (fr)	2006-04-17	2007-04-17	O-desmethylvenlafaxine essentiellement pure et ses procedes de preparation

Country Status (6)

Country	Link
EP (1)	EP2007708A1 (fr)
JP (1)	JP2008546718A (fr)
CA (1)	CA2646368A1 (fr)
IL (1)	IL193398A0 (fr)
MX (1)	MX2007016172A (fr)
WO (1)	WO2007120923A1 (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX2007016179A (es)	2006-04-17	2008-03-11	Teva Pharma	Formas cristalinas de o-desmetilvenlafaxina.
WO2008035369A2 (fr) *	2006-06-30	2008-03-27	Alembic Limited	Nouvelle forme de o-desméthyl venlafaxine
US20090062572A1 (en)	2006-07-26	2009-03-05	Valerie Niddam-Hildesheim	Processes for the synthesis of O-desmethylvenlafaxine
US20090069601A1 (en) *	2006-07-26	2009-03-12	Valerie Niddam-Hildesheim	Processes for the synthesis of O-desmethylvenlafaxine
CA2656285A1 (fr) *	2006-07-26	2008-01-31	Teva Pharmaceutical Industries Ltd.	Procedes pour la synthese d'o-desmethylvenlafaxine
US20100121108A1 (en) *	2006-08-04	2010-05-13	Medichem, S.A.	Process for synthesizing desvenlafaxine free base and salts or solvates thereof
EP2049465A2 (fr) *	2007-03-14	2009-04-22	Teva Pharmaceutical Industries Ltd.	Procédés pour préparer des états solides de succinate d'o-desméthylvenlafaxine
CA2703647A1 (fr) *	2007-10-26	2009-04-30	Generics [Uk] Limited	Procede de preparation de o-desmethylvenlafaxine
WO2009070311A2 (fr)	2007-11-26	2009-06-04	Teva Pharmaceutical Industries Ltd.	Formes cristallines de fumarate de o-desméthylvenlafaxine
WO2009084038A2 (fr) *	2007-12-28	2009-07-09	Ind-Swift Laboratories Limited	Procédé amélioré d'élaboration d'o-desméthyl venlafaxine
CA2717580A1 (fr) *	2008-03-06	2009-12-17	Teva Pharmaceutical Industries Ltd.	Procedes de preparation de la o-desmethylvenlafaxine, exempte de ses impuretes dimeres
CZ2008756A3 (cs)	2008-11-27	2010-03-24	Zentiva, A. S.	Zpusob prípravy desvenlafaxinu a jeho solí
ES2343050B1 (es) *	2008-12-16	2011-06-14	Chemo Iberica, S.A.	Procedimiento para la preparacion de desvenlafaxina y sus sales de adicion de acido farmaceuticamente aceptables.
CZ200969A3 (cs)	2009-02-06	2010-06-30	Zentiva, K.S.	Nové soli desvenlafaxinu a zpusob jejich prípravy
CZ302145B6 (cs)	2009-07-15	2010-11-10	Zentiva, K. S.	Zpusob prípravy desvenlafaxinu a jeho solí
WO2011121452A2 (fr)	2010-03-29	2011-10-06	Pliva Hrvatska D.O.O.	Formes cristallines du fumarate de o-desméthylvenlafaxine
CZ303249B6 (cs)	2010-04-06	2012-06-20	Zentiva, K.S.	Zpusob výroby 4-(2-(substituovaných)-1-(1-hydroxycyklohexyl)ethyl)fenolu O-demethylací jejich methyletheru pomocí nepáchnoucích aromatických thiolu
JP6751200B2 (ja)	2017-02-09	2020-09-02	アールエルファインケムプライベートリミテッド	１−［２−（ジメチルアミノ）−１−（４−ヒドロキシフェニル）エチル］−シクロヘキサノール及びその塩の製造方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6197828B1 (en) *	1998-12-01	2001-03-06	Sepracor, Inc.	Derivatives of (+)-venlafaxine and methods of preparing and using the same
ES2305606T3 (es)	1999-04-06	2008-11-01	Sepracor Inc.	Succinato de o-desmetilvenlafaxina.
ATE369330T1 (de)	2001-02-12	2007-08-15	Wyeth Corp	O-desmethyl-venlafaxine succinat salz
UA80543C2 (en) *	2001-12-04	2007-10-10	Wyeth Corp	Method for the preparation of o-desmethylvenlafaxine
WO2007071404A1 (fr) *	2005-12-20	2007-06-28	Synthon B.V.	Procédé de fabrication de la desvenlafaxine

2007
- 2007-04-17 EP EP07755727A patent/EP2007708A1/fr not_active Withdrawn
- 2007-04-17 MX MX2007016172A patent/MX2007016172A/es unknown
- 2007-04-17 JP JP2008517241A patent/JP2008546718A/ja active Pending
- 2007-04-17 WO PCT/US2007/009558 patent/WO2007120923A1/fr not_active Ceased
- 2007-04-17 CA CA002646368A patent/CA2646368A1/fr not_active Abandoned
2008
- 2008-08-12 IL IL193398A patent/IL193398A0/en unknown

Also Published As

Publication number	Publication date
JP2008546718A (ja)	2008-12-25
EP2007708A1 (fr)	2008-12-31
MX2007016172A (es)	2008-03-10
IL193398A0 (en)	2009-05-04
WO2007120923A1 (fr)	2007-10-25

Publication	Publication Date	Title
CA2646368A1 (fr)	2007-10-25	O-desmethylvenlafaxine essentiellement pure et ses procedes de preparation
US20090292142A1 (en)	2009-11-26	Substantially pure O-desmethylvenlafaxine and processes for preparing it
US20080161607A1 (en)	2008-07-03	Processes for preparation of polymorphic form II of sertraline hydrochloride
US20210317085A1 (en)	2021-10-14	Solid state forms of omecamtiv mecarbil & omecamtiv mecarbil dihcl
US20080033054A1 (en)	2008-02-07	Process for preparing memantine hydrochloride substantially free of impurities
US12492213B2 (en)	2025-12-09	Solid state forms of sep-363856 and process for preparation thereof
EP3652193A1 (fr)	2020-05-20	Nouvelles formes polymorphes cristallines du bardoxolone méthyle
CN101472878A (zh)	2009-07-01	O-去甲基文拉法辛晶型
US20090012182A1 (en)	2009-01-08	Crystal forms of O-desmethylvenlafaxine succinate
US20080027128A1 (en)	2008-01-31	Duloxetine HCL polymorphs
WO2024218682A1 (fr)	2024-10-24	Formes à l'état solide de fosgonimeton et leurs sels
WO2007038253A2 (fr)	2007-04-05	Dnt-maleate, procedes de preparation de dernier
US20070191471A1 (en)	2007-08-16	DNT-fumarate and methods of preparation thereof

Legal Events

Date	Code	Title	Description
2008-08-25	EEER	Examination request
2012-01-12	FZDE	Discontinued