EA009385B1 - Способ энантиоселективного синтеза отдельных энантиомеров модафинила асиметричным окислением - Google Patents
Способ энантиоселективного синтеза отдельных энантиомеров модафинила асиметричным окислением Download PDFInfo
- Publication number
- EA009385B1 EA009385B1 EA200600593A EA200600593A EA009385B1 EA 009385 B1 EA009385 B1 EA 009385B1 EA 200600593 A EA200600593 A EA 200600593A EA 200600593 A EA200600593 A EA 200600593A EA 009385 B1 EA009385 B1 EA 009385B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- chiral ligand
- purity
- metal complex
- sulfoxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 146
- 238000007254 oxidation reaction Methods 0.000 title claims description 73
- 230000003647 oxidation Effects 0.000 title claims description 67
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 title claims description 29
- 229960001165 modafinil Drugs 0.000 title claims description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title description 43
- 230000008569 process Effects 0.000 title description 18
- 230000015572 biosynthetic process Effects 0.000 title description 17
- 238000003786 synthesis reaction Methods 0.000 title description 7
- -1 sulphoxide compound Chemical class 0.000 claims abstract description 76
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000007800 oxidant agent Substances 0.000 claims abstract description 35
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 16
- 239000003446 ligand Substances 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 150000003462 sulfoxides Chemical class 0.000 claims description 49
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 150000004696 coordination complex Chemical class 0.000 claims description 31
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 27
- 229910052719 titanium Inorganic materials 0.000 claims description 27
- 239000010936 titanium Substances 0.000 claims description 27
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 14
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
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- QARQPIWTMBRJFX-UHFFFAOYSA-N modafinil acid Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)O)C1=CC=CC=C1 QARQPIWTMBRJFX-UHFFFAOYSA-N 0.000 claims description 10
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- KJPGMBAVZUTLAA-UHFFFAOYSA-N o-methyl 3,3-diphenylpropanethioate Chemical compound C=1C=CC=CC=1C(CC(=S)OC)C1=CC=CC=C1 KJPGMBAVZUTLAA-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000010956 selective crystallization Methods 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
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- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- CKIWWDLKOCDKHX-UHFFFAOYSA-N 2-benzhydrylsulfinylacetonitrile Chemical compound C=1C=CC=CC=1C(S(CC#N)=O)C1=CC=CC=C1 CKIWWDLKOCDKHX-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 230000002862 amidating effect Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
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- 239000002585 base Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HCRQRIFRHGPWBH-UHFFFAOYSA-N 2-benzhydrylsulfanylacetamide Chemical compound C=1C=CC=CC=1C(SCC(=O)N)C1=CC=CC=C1 HCRQRIFRHGPWBH-UHFFFAOYSA-N 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 22
- 150000003568 thioethers Chemical class 0.000 description 22
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- 230000000694 effects Effects 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940124530 sulfonamide Drugs 0.000 description 12
- 150000003456 sulfonamides Chemical class 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- BIASHYVHAQBNGV-UHFFFAOYSA-N 3,3-diphenylpropanethioic s-acid Chemical compound C=1C=CC=CC=1C(CC(=S)O)C1=CC=CC=C1 BIASHYVHAQBNGV-UHFFFAOYSA-N 0.000 description 11
- 125000004434 sulfur atom Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- YFGHCGITMMYXAQ-LJQANCHMSA-N armodafinil Chemical compound C=1C=CC=CC=1C([S@](=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-LJQANCHMSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- 229910021529 ammonia Inorganic materials 0.000 description 6
- YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 description 6
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- 125000000304 alkynyl group Chemical group 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical class N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000011914 asymmetric synthesis Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
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- 238000004128 high performance liquid chromatography Methods 0.000 description 4
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- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- 150000003609 titanium compounds Chemical class 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- SLRFIGRURFZMHI-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine;toluene Chemical compound CC1=CC=CC=C1.CCN(C(C)C)C(C)C SLRFIGRURFZMHI-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 150000004843 oxaziridines Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical class [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same 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
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03292312A EP1516869A1 (en) | 2003-09-19 | 2003-09-19 | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US50708903P | 2003-10-01 | 2003-10-01 | |
| PCT/IB2004/003026 WO2005028428A1 (en) | 2003-09-19 | 2004-09-17 | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200600593A1 EA200600593A1 (ru) | 2006-08-25 |
| EA009385B1 true EA009385B1 (ru) | 2007-12-28 |
Family
ID=34178643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200600593A EA009385B1 (ru) | 2003-09-19 | 2004-09-17 | Способ энантиоселективного синтеза отдельных энантиомеров модафинила асиметричным окислением |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7317126B2 (enExample) |
| EP (2) | EP1516869A1 (enExample) |
| JP (1) | JP4713480B2 (enExample) |
| KR (1) | KR101136703B1 (enExample) |
| CN (1) | CN100404502C (enExample) |
| AT (1) | ATE365711T1 (enExample) |
| AU (1) | AU2004274248B2 (enExample) |
| BR (1) | BRPI0414298B1 (enExample) |
| CA (1) | CA2538697C (enExample) |
| DE (1) | DE602004007278T2 (enExample) |
| DK (1) | DK1663963T3 (enExample) |
| EA (1) | EA009385B1 (enExample) |
| ES (1) | ES2289556T3 (enExample) |
| MX (1) | MXPA06002935A (enExample) |
| NZ (1) | NZ545739A (enExample) |
| PL (1) | PL1663963T3 (enExample) |
| PT (1) | PT1663963E (enExample) |
| SI (1) | SI1663963T1 (enExample) |
| UA (1) | UA85196C2 (enExample) |
| WO (1) | WO2005028428A1 (enExample) |
| ZA (1) | ZA200601962B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2448954C1 (ru) * | 2010-10-18 | 2012-04-27 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Способ получения сульфоксидов |
| RU2477316C1 (ru) * | 2011-12-29 | 2013-03-10 | Учреждение Российской академии наук Институт экологии и генетики микроорганизмов Уральского отделения РАН | Биокаталитический способ получения (r)-фенилметилового сульфоксида |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| EP1702915A1 (en) * | 2005-03-14 | 2006-09-20 | Cephalon France | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
| CN1321978C (zh) * | 2005-04-29 | 2007-06-20 | 浙江工业大学 | 一种2－（二苯基甲基亚硫酰基）乙酰胺的合成方法 |
| WO2007027328A2 (en) * | 2005-07-28 | 2007-03-08 | University Of Iowa Research Foundation | Microbial sulfoxidation and amidation of benzhdrylsulfanyl carboxylic acids and uses thereof |
| US20070293702A1 (en) * | 2006-02-21 | 2007-12-20 | Viviana Braude | Novel crystalline forms of armodafinil and preparation thereof |
| WO2007103221A2 (en) | 2006-03-01 | 2007-09-13 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of armodafinil |
| WO2008070143A1 (en) * | 2006-12-06 | 2008-06-12 | Teva Pharmaceutical Industries Ltd. | Processes for preparing armodafinil intermediate |
| EP2155664A2 (en) * | 2007-06-04 | 2010-02-24 | Generics Ýuk¨Limited | Novel process |
| WO2009024863A2 (en) * | 2007-06-26 | 2009-02-26 | Actavis Group Ptc Ehf | Process for the preparation of modafinil enantiomers |
| US7960586B2 (en) * | 2007-08-16 | 2011-06-14 | Teva Pharmaceutical Industries Ltd. | Purification of armodafinil |
| CN102471290B (zh) * | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| AU2011203970A1 (en) * | 2010-01-07 | 2012-07-12 | Vivus, Inc. | Treatment of obstructive sleep apnea syndrome with a combination of a carbonic anhydrase inhibitor and an additional active agent |
| EP2649187B1 (en) | 2010-12-08 | 2017-11-22 | Codexis, Inc. | Biocatalysts and methods for the synthesis of armodafinil |
| FR2970711B1 (fr) * | 2011-01-20 | 2016-03-04 | Hopitaux Paris Assist Publique | La lauflumide et ses enantiomeres, preparation et utilisations therapeutiques |
| CN104447440B (zh) * | 2013-09-12 | 2016-05-18 | 中国科学院大连化学物理研究所 | 一种催化不对称氧化硫醚的方法 |
| CN104045588A (zh) * | 2014-06-11 | 2014-09-17 | 江苏斯威森生物医药工程研究中心有限公司 | 一种2-(4,4’-二卤-二苯基甲基亚磺酰)乙酰胺的合成方法 |
| HUE035104T2 (en) | 2014-08-13 | 2018-05-02 | Red Bull Gmbh | Heterocyclic compounds with activity memory stimulating activity |
| CA2989243C (en) | 2014-08-13 | 2023-03-14 | Red Bull Gmbh | Heterocyclic compounds with working memory enhancing activity |
| US9616068B2 (en) | 2014-10-27 | 2017-04-11 | Pohela LLC | Animal training using cognitive enhancement |
| CN110698482A (zh) * | 2019-10-29 | 2020-01-17 | 株洲千金药业股份有限公司 | 一种s型手性亚砜类化合物的制备方法 |
| CN110746428A (zh) * | 2019-10-29 | 2020-02-04 | 株洲千金药业股份有限公司 | 一种r型手性亚砜类化合物的制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4177290A (en) * | 1977-03-31 | 1979-12-04 | Laboratoire L. Lafon | Acetamide derivatives |
| EP0233106A1 (fr) * | 1986-01-31 | 1987-08-19 | Laboratoire L. Lafon | (-)-Benzhydrylsulfinylacétamide, procédé de préparation et utilisation en thérapeutique |
| WO2002010125A1 (en) * | 2000-07-27 | 2002-02-07 | Teva Pharmaceutical Industries Ltd. | Crystalline and pure modafinil, and process of preparing the same |
| EP1260501A1 (en) * | 2001-05-13 | 2002-11-27 | Chemagis Ltd. | Process for the preparation of diphenylmethylthioacetamide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127722A (en) * | 1975-10-02 | 1978-11-28 | Laboratoire L. Lafon | Benzhydrylsulphinyl derivatives |
| FR2528038B2 (fr) * | 1982-06-04 | 1985-08-09 | Lafon Labor | Derives de benzhydrylsulfinylacetamide et leur utilisation en therapeutique |
| US20040048931A1 (en) | 2002-07-12 | 2004-03-11 | Craig Heacock | Modafinil pharmaceutical compositions |
| FR2849029B1 (fr) | 2002-12-20 | 2005-03-18 | Lafon Labor | Procede de preparation et formes cristallines des enantiomeres optiques du modafinil. |
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
-
2003
- 2003-09-19 EP EP03292312A patent/EP1516869A1/en not_active Withdrawn
-
2004
- 2004-09-17 WO PCT/IB2004/003026 patent/WO2005028428A1/en not_active Ceased
- 2004-09-17 CN CNB2004800298265A patent/CN100404502C/zh not_active Expired - Fee Related
- 2004-09-17 DE DE602004007278T patent/DE602004007278T2/de not_active Expired - Lifetime
- 2004-09-17 ES ES04769402T patent/ES2289556T3/es not_active Expired - Lifetime
- 2004-09-17 EP EP04769402A patent/EP1663963B1/en not_active Expired - Lifetime
- 2004-09-17 PL PL04769402T patent/PL1663963T3/pl unknown
- 2004-09-17 EA EA200600593A patent/EA009385B1/ru not_active IP Right Cessation
- 2004-09-17 UA UAA200604415A patent/UA85196C2/ru unknown
- 2004-09-17 MX MXPA06002935A patent/MXPA06002935A/es active IP Right Grant
- 2004-09-17 CA CA2538697A patent/CA2538697C/en not_active Expired - Fee Related
- 2004-09-17 AU AU2004274248A patent/AU2004274248B2/en not_active Expired
- 2004-09-17 AT AT04769402T patent/ATE365711T1/de active
- 2004-09-17 SI SI200430411T patent/SI1663963T1/sl unknown
- 2004-09-17 JP JP2006526728A patent/JP4713480B2/ja not_active Expired - Fee Related
- 2004-09-17 PT PT04769402T patent/PT1663963E/pt unknown
- 2004-09-17 US US10/943,360 patent/US7317126B2/en not_active Expired - Fee Related
- 2004-09-17 KR KR1020067007002A patent/KR101136703B1/ko not_active Expired - Fee Related
- 2004-09-17 NZ NZ545739A patent/NZ545739A/en not_active IP Right Cessation
- 2004-09-17 DK DK04769402T patent/DK1663963T3/da active
- 2004-09-17 BR BRPI0414298-5A patent/BRPI0414298B1/pt not_active IP Right Cessation
-
2006
- 2006-03-08 ZA ZA200601962A patent/ZA200601962B/en unknown
-
2007
- 2007-10-30 US US11/929,030 patent/US7812193B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4177290A (en) * | 1977-03-31 | 1979-12-04 | Laboratoire L. Lafon | Acetamide derivatives |
| EP0233106A1 (fr) * | 1986-01-31 | 1987-08-19 | Laboratoire L. Lafon | (-)-Benzhydrylsulfinylacétamide, procédé de préparation et utilisation en thérapeutique |
| WO2002010125A1 (en) * | 2000-07-27 | 2002-02-07 | Teva Pharmaceutical Industries Ltd. | Crystalline and pure modafinil, and process of preparing the same |
| EP1260501A1 (en) * | 2001-05-13 | 2002-11-27 | Chemagis Ltd. | Process for the preparation of diphenylmethylthioacetamide |
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| Title |
|---|
| COTTON H. ET AL.: "Asymmetric synthesis of esomeprazole", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 11, no. 18, 22 September 2000 (2000-09-22), pages 3819-3825, XP004224163, ISSN: 0957-4166, cited in the application, abstract * |
| MICHEL MADESCLAIRE: "Synthesis of sulfoxides by oxidation of thioethers", TETRAHEDRON., vol. 42, no. 20, 1986, pages 5459-5495, XP002269656, OXFORD, GB, cited in the application, page 5461 - page 5462 * |
| PITCHEN P. ET AL.: "AN EFFICIENT ASYMMETRI OXIDATION OF SULFIDES TO SULFOXIDES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 106, 26 December 1984 (1984-12-26), pages 8188-8193, XP000644322, ISSN: 0002-7863, cited in the application, abstract; tables I, II * |
| S. H. ZHAO ET AL.: "Asymmetric oxidation of sulfides mediated by chiral titanium complexes: mechanistic and synthetic aspects", TETRAHEDRON.., vol. 43, no. 21, 1987, pages 5135-5144, XP002269655, OXFORD, GB, cited in the application, page 5141; claims 1-4 * |
| S.H. ZHAO ET AL.: "Organic syntheses, vol. VIII", 1993, JOHN WILEY AND SONS, NEW YORK, XP001091383, cited in the application, page 464 - page 467 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2448954C1 (ru) * | 2010-10-18 | 2012-04-27 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Способ получения сульфоксидов |
| RU2477316C1 (ru) * | 2011-12-29 | 2013-03-10 | Учреждение Российской академии наук Институт экологии и генетики микроорганизмов Уральского отделения РАН | Биокаталитический способ получения (r)-фенилметилового сульфоксида |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004274248A1 (en) | 2005-03-31 |
| CA2538697A1 (en) | 2005-03-31 |
| JP2007505891A (ja) | 2007-03-15 |
| ES2289556T3 (es) | 2008-02-01 |
| UA85196C2 (ru) | 2009-01-12 |
| BRPI0414298A (pt) | 2006-11-14 |
| WO2005028428A1 (en) | 2005-03-31 |
| EP1663963A1 (en) | 2006-06-07 |
| DE602004007278D1 (de) | 2007-08-09 |
| SI1663963T1 (sl) | 2007-12-31 |
| KR20070009968A (ko) | 2007-01-19 |
| BRPI0414298B1 (pt) | 2021-06-08 |
| CN1867544A (zh) | 2006-11-22 |
| PL1663963T3 (pl) | 2007-11-30 |
| ATE365711T1 (de) | 2007-07-15 |
| KR101136703B1 (ko) | 2012-05-24 |
| AU2004274248B2 (en) | 2010-08-26 |
| EP1516869A1 (en) | 2005-03-23 |
| DE602004007278T2 (de) | 2008-02-28 |
| NZ545739A (en) | 2010-01-29 |
| CA2538697C (en) | 2012-11-13 |
| US7317126B2 (en) | 2008-01-08 |
| DK1663963T3 (da) | 2007-10-29 |
| MXPA06002935A (es) | 2006-06-14 |
| EA200600593A1 (ru) | 2006-08-25 |
| US20080171896A1 (en) | 2008-07-17 |
| EP1663963B1 (en) | 2007-06-27 |
| CN100404502C (zh) | 2008-07-23 |
| PT1663963E (pt) | 2007-10-19 |
| ZA200601962B (en) | 2007-06-27 |
| JP4713480B2 (ja) | 2011-06-29 |
| US20050080256A1 (en) | 2005-04-14 |
| US7812193B2 (en) | 2010-10-12 |
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