NO319078B1 - Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen - Google Patents
Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen Download PDFInfo
- Publication number
- NO319078B1 NO319078B1 NO20021994A NO20021994A NO319078B1 NO 319078 B1 NO319078 B1 NO 319078B1 NO 20021994 A NO20021994 A NO 20021994A NO 20021994 A NO20021994 A NO 20021994A NO 319078 B1 NO319078 B1 NO 319078B1
- Authority
- NO
- Norway
- Prior art keywords
- dichlorophenyl
- compound
- formula
- methyl
- cis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 title claims description 22
- 229960002073 sertraline Drugs 0.000 title claims description 22
- 239000000543 intermediate Substances 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- -1 methoxy, ethoxy Chemical group 0.000 claims description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 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 claims description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 13
- VGKDLMBJGBXTGI-SJKOYZFVSA-N (1r,4r)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJKOYZFVSA-N 0.000 description 12
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000011949 solid catalyst Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- VGKDLMBJGBXTGI-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C12=CC=CC=C2C(NC)CCC1C1=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-UHFFFAOYSA-N 0.000 description 3
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- RLJAZNIZTJTMHW-UHFFFAOYSA-N n-benzyl-4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C1=C(Cl)C(Cl)=CC=C1C(CC1)C2=CC=CC=C2C1=NCC1=CC=CC=C1 RLJAZNIZTJTMHW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229960003660 sertraline hydrochloride Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000000825 ultraviolet detection Methods 0.000 description 3
- JGMBHJNMQVKDMW-NSHDSACASA-N (4s)-4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1[C@H]1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-NSHDSACASA-N 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- MQRPIOBQLHVTPW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-[(3,4-dimethoxyphenyl)methyl]-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C1=C(OC)C(OC)=CC=C1CN=C1C2=CC=CC=C2C(C=2C=C(Cl)C(Cl)=CC=2)CC1 MQRPIOBQLHVTPW-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- PUKBOMXODMUDBW-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2CCC1 PUKBOMXODMUDBW-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- DPCXOOJTAKKWIC-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(Cl)C(Cl)=C1 DPCXOOJTAKKWIC-UHFFFAOYSA-N 0.000 description 1
- LYUMYEHBZWBIRA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-[(4-methoxyphenyl)methyl]-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C1=CC(OC)=CC=C1CN=C1C2=CC=CC=C2C(C=2C=C(Cl)C(Cl)=CC=2)CC1 LYUMYEHBZWBIRA-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 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 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- KHUIIQYMRBKTAV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C1=CC(Cl)=CC=C1CN=C1C2=CC=CC=C2C(C=2C=C(Cl)C(Cl)=CC=2)CC1 KHUIIQYMRBKTAV-UHFFFAOYSA-N 0.000 description 1
- AVIMZTWSMJIMQM-UHFFFAOYSA-N n-benzyl-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1CC(C=2C=C(Cl)C(Cl)=CC=2)C2=CC=CC=C2C1N(C)CC1=CC=CC=C1 AVIMZTWSMJIMQM-UHFFFAOYSA-N 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
- A23G3/40—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds characterised by the fats used
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/066—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the fat used
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/08—Chewing gum characterised by the composition containing organic or inorganic compounds of the chewing gum base
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Confectionery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199801540 | 1998-11-23 | ||
| PCT/DK2000/000586 WO2001030742A1 (en) | 1998-11-23 | 2000-10-20 | Improved synthesis of racemic sertraline |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20021994D0 NO20021994D0 (no) | 2002-04-26 |
| NO20021994L NO20021994L (no) | 2002-04-26 |
| NO319078B1 true NO319078B1 (no) | 2005-06-13 |
Family
ID=8105881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021994A NO319078B1 (no) | 1998-11-23 | 2002-04-26 | Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6787167B1 (et) |
| EP (2) | EP1133241B1 (et) |
| AT (2) | ATE306824T1 (et) |
| AU (3) | AU1031500A (et) |
| CA (1) | CA2351401C (et) |
| DE (1) | DE69927842T2 (et) |
| DK (2) | DK1133241T3 (et) |
| EA (1) | EA004371B1 (et) |
| EE (1) | EE04794B1 (et) |
| ES (1) | ES2249064T3 (et) |
| NO (1) | NO319078B1 (et) |
| UA (1) | UA71939C2 (et) |
| WO (3) | WO2000025598A1 (et) |
| ZA (1) | ZA200104630B (et) |
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| DE69921972T2 (de) * | 1998-03-04 | 2005-12-01 | Dandy A/S | Beschichteter kaugummi, verfahren zur herstellung und verwendung von einem oder mehreren festen aktiven stoffen |
| JP2003527359A (ja) | 2000-03-14 | 2003-09-16 | テバ ファーマシューティカル インダストリーズ リミティド | （＋）−シス−セルトラリンの製造のための新規方法 |
| EP1922937A3 (en) | 2001-03-23 | 2008-06-04 | Gumlink A/S | Coated degradable chewing gum with improved shelf life and process for preparing same |
| US7507427B2 (en) | 2001-03-23 | 2009-03-24 | Gumlink A/S | Coated degradable chewing gum with improved shelf life and process for preparing same |
| US20030027786A1 (en) | 2001-06-06 | 2003-02-06 | Karsten Maeder | Lipase inhibiting composition |
| ITMI20012322A1 (it) * | 2001-11-06 | 2003-05-06 | Perfetti Van Melle Spa | Composizioni orali solide anti-tartaro e anti-placca batterica, utilicome coadiuvanti nell'igiene odont-stomatologica |
| CA2483569A1 (en) | 2002-04-29 | 2003-11-13 | Tamar Nidam | Process for preparation of polymorphic form ii of sertraline hydrochloride, pharmaceutical formulations and methods of administration thereof |
| ES2311631T3 (es) | 2002-09-24 | 2009-02-16 | Gumlink A/S | Goma de mascar biodegradable que comprende por lo menos un polimero biodegradable de alto peso molecular. |
| ES2578252T3 (es) | 2002-09-24 | 2016-07-22 | Gumlink A/S | Goma de mascar que comprende al menos dos polímeros biodegradables diferentes |
| WO2004028267A1 (en) * | 2002-09-24 | 2004-04-08 | Gumlink A/S | Chewing gum having improved release of chewing gum ingredients |
| US20040175489A1 (en) * | 2003-03-03 | 2004-09-09 | Wm. Wrigley Jr. Company | Fast flavor release coating for confectionery |
| TW200503991A (en) * | 2003-04-14 | 2005-02-01 | Teva Pharma | Hydrogenation of imine intermediates of sertraline with catalysts |
| US7262327B2 (en) * | 2003-09-05 | 2007-08-28 | Teva Pharmaceutical Industries Ltd. | Recycling process for preparing sertraline |
| AU2003294811A1 (en) | 2003-12-08 | 2005-07-05 | Cadbury Holdings Limited | A solid oral tooth whithening composition |
| WO2006000233A1 (en) * | 2004-06-29 | 2006-01-05 | Fertin Pharma A/S | Tobacco alkaloid containing chewing gum |
| JP4875616B2 (ja) | 2004-07-06 | 2012-02-15 | ガムリンク エー／エス | 圧縮チューインガムタブレット |
| CA2581289C (en) | 2004-10-08 | 2016-03-22 | Gumlink A/S | Confectionery product |
| EP1817014B1 (en) | 2004-11-30 | 2012-08-22 | Fertin Pharma A/S | Method of providing fast relief to a user of a nicotine chewing gum |
| TW200640836A (en) | 2005-02-23 | 2006-12-01 | Teva Pharma | Processes for preparing sertraline |
| EP1976391B1 (en) | 2005-12-30 | 2010-10-20 | Cadbury Holdings Limited | Chewing gum composition containing chokeberry |
| TR200808115T1 (tr) * | 2006-04-28 | 2009-03-23 | Sandoz Ag | 4(S,R)-(3,4-diklorofenil)-3,4-dihidro-l(2H)-naftalin-l-ilid n]metilamin'ın Hazırlanması için Proses.@ |
| EP2012595A1 (en) | 2006-04-28 | 2009-01-14 | Gumlink A/S | Transparent confectionery product |
| ES2352147T3 (es) | 2006-09-29 | 2011-02-16 | Cadbury Holdings Limited | Goma de mascar que comprende polietileno. |
| US20080107771A1 (en) * | 2006-10-20 | 2008-05-08 | Wm. Wrigley Jr. Company | Apparatus and method of making center-filled confectionery product |
| FR2909376A1 (fr) * | 2006-11-30 | 2008-06-06 | Cerep Sa | Procedes de preparation de la desmethulsertraline ou d'un de ses sels pharmaceutiquement acceptables |
| WO2008145120A1 (en) | 2007-05-31 | 2008-12-04 | Gumlink A/S | Environmental chewing gum |
| MD3856G2 (ro) * | 2007-11-23 | 2009-10-31 | Валериу ФАЛА | Gumă de mestecat (variante) |
| WO2009080021A1 (en) | 2007-12-20 | 2009-07-02 | Fertin Pharma A/S | Compressed chewing gum tablet |
| DK2229156T3 (en) | 2007-12-20 | 2017-02-06 | Fertin Pharma As | CHEW GUM TABLE AND PROCEDURE FOR DOSING PHARMACEUTICAL ACTIVE INGREDIENTS IN SUCH CHEW GUM TABLE |
| WO2009080022A1 (en) | 2007-12-20 | 2009-07-02 | Fertin Pharma A/S | Compressed chewing gum tablet |
| MD3900G2 (ro) * | 2007-12-21 | 2009-12-31 | Валериу ФАЛА | Gumă de mestecat cu acţiune analgezică şi antistres (variante) |
| MD3857G2 (ro) * | 2007-12-21 | 2009-10-31 | Валериу ФАЛА | Gumă de mestecat pentru remineralizarea smalţului dentar (variante) |
| MD3878G2 (ro) * | 2008-02-18 | 2009-11-30 | Валериу ФАЛА | Gumă de mestecat (variante) |
| DK2282645T3 (en) | 2008-05-26 | 2015-07-13 | Fertin Pharma As | Flavor impregnation of a chewing gum |
| US8722117B2 (en) * | 2008-06-04 | 2014-05-13 | Wm. Wrigley Jr. Company | Method and apparatus for thermal sealing a filled confectionery product |
| EP2442668B1 (en) | 2009-06-19 | 2016-08-10 | Fertin Pharma A/S | Buffered gum base for high ph release |
| US20110038915A1 (en) * | 2009-08-14 | 2011-02-17 | Eduardo Jose Gonzalez | Chewing Gum Formula for Enhancing Psycho-Spirituality |
| US8293299B2 (en) | 2009-09-11 | 2012-10-23 | Kraft Foods Global Brands Llc | Containers and methods for dispensing multiple doses of a concentrated liquid, and shelf stable Concentrated liquids |
| GB201004890D0 (en) | 2010-03-23 | 2010-05-05 | Cadbury Uk Ltd | Confectionery product containing active and/or reactive components and methods of production thereof |
| EP2654738B1 (en) | 2010-12-21 | 2018-04-18 | Fertin Pharma A/S | Chewing gum composition comprising cross-linked polyacrylic acid |
| US10736335B2 (en) | 2011-11-17 | 2020-08-11 | Wm. Wrigley Jr. Company | Chewing gum compositions based on dried fruit powders |
| WO2013091631A1 (en) | 2011-12-22 | 2013-06-27 | Fertin Pharma A/S | Method of releasing nicotine from chewing gum |
| US11013248B2 (en) | 2012-05-25 | 2021-05-25 | Kraft Foods Group Brands Llc | Shelf stable, concentrated, liquid flavorings and methods of preparing beverages with the concentrated liquid flavorings |
| WO2014086358A1 (en) | 2012-12-07 | 2014-06-12 | Gumlink A/S | Compressed tablets |
| WO2014160064A1 (en) * | 2013-03-14 | 2014-10-02 | Ocean Spray Cranberries, Inc. | Flow agent methods and products |
| RU2558800C1 (ru) * | 2014-08-14 | 2015-08-10 | Сергей Васильевич Чуйкин | Способ местного лечения и профилактики основных стоматологических заболеваний у детей с церебральным параличом с применением жевательного фитокомплекса |
| KR102629093B1 (ko) * | 2015-02-27 | 2024-01-24 | 가부시키가이샤 롯데 | 추잉껌 |
| ES2940581T3 (es) * | 2015-11-30 | 2023-05-09 | Wrigley W M Jun Co | Gomas de mascar y mentas prensadas con características superficiales |
| US11311623B2 (en) | 2016-04-21 | 2022-04-26 | Fertin Pharma A/S | Nicotine delivery product, related uses and oral dosage forms, and methods of production |
| RU2747506C2 (ru) * | 2016-09-23 | 2021-05-06 | Вм. Ригли Джр. Компани | Стабильные ароматизирующие композиции, содержащие листья мяты |
| MX2019005928A (es) | 2016-11-18 | 2019-11-12 | Fertin Pharma As | Método para proporcionar beneficios para el cuidado bucal. |
| PL3541357T3 (pl) | 2016-11-18 | 2021-08-02 | Fertin Pharma A/S | Doustne podłoże dostarczające |
| US11058633B2 (en) | 2018-05-17 | 2021-07-13 | Fertin Pharma A/S | Disintegrating oral tablet suitable for active pharmaceutical ingredients |
| US11096896B2 (en) | 2018-05-17 | 2021-08-24 | Fertin Pharma A/S | Tablet dosage form for buccal absorption of active ingredients |
| US11096895B2 (en) | 2018-05-17 | 2021-08-24 | Fertin Pharma A/S | Oral tablet suitable for active pharmaceutical ingredients |
| US11135157B2 (en) | 2018-05-17 | 2021-10-05 | Fertin Pharma A/S | Oral tablet for delivery of active ingredients to the throat |
| WO2019219147A1 (en) | 2018-05-17 | 2019-11-21 | Fertin Pharma A/S | A tableted chewing gum suitable for active pharmaceutical ingredients |
| US11096894B2 (en) | 2018-05-17 | 2021-08-24 | Fertin Pharma A/S | Oral tablet for induced saliva generation |
| US11052047B2 (en) | 2018-05-17 | 2021-07-06 | Fertin Pharma A/S | Oral tablet suitable for fast release of active pharmaceutical ingredients |
| US11058641B2 (en) | 2018-05-17 | 2021-07-13 | Fertin Pharma A/S | Oral tablet for taste masking of active ingredients |
| US20190350858A1 (en) | 2018-05-17 | 2019-11-21 | Fertin Pharma A/S | Oral tablet for delivery of active ingredients to the gastrointestinal tract |
| GB201904767D0 (en) | 2019-04-04 | 2019-05-22 | Orexo Ab | New pharmaceutical compositions |
| CA3174693A1 (en) | 2020-05-08 | 2021-11-11 | Fertin Pharma A/S | Flowpack for oral delivery of active ingredients |
| US20230123099A1 (en) | 2021-10-15 | 2023-04-20 | Fertin Pharma A/S | Dextrose tablets with improved mouthfeel |
| WO2024002447A1 (en) | 2022-06-30 | 2024-01-04 | Fertin Pharma A/S | Flowpack with composition for improved taste masking of actives |
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-
1999
- 1999-11-03 WO PCT/DK1999/000598 patent/WO2000025598A1/en active Application Filing
- 1999-11-03 AU AU10315/00A patent/AU1031500A/en not_active Abandoned
- 1999-11-23 ES ES99972499T patent/ES2249064T3/es not_active Expired - Lifetime
- 1999-11-23 CA CA002351401A patent/CA2351401C/en not_active Expired - Fee Related
- 1999-11-23 AT AT99972499T patent/ATE306824T1/de not_active IP Right Cessation
- 1999-11-23 EE EEP200100274A patent/EE04794B1/et not_active IP Right Cessation
- 1999-11-23 DK DK99972499T patent/DK1133241T3/da active
- 1999-11-23 DE DE69927842T patent/DE69927842T2/de not_active Expired - Lifetime
- 1999-11-23 UA UA2001064422A patent/UA71939C2/uk unknown
- 1999-11-23 EA EA200100582A patent/EA004371B1/ru not_active IP Right Cessation
- 1999-11-23 EP EP99972499A patent/EP1133241B1/en not_active Expired - Lifetime
- 1999-11-23 US US09/856,540 patent/US6787167B1/en not_active Expired - Fee Related
- 1999-11-23 WO PCT/DK1999/000649 patent/WO2000030465A1/en active IP Right Grant
- 1999-11-23 AU AU13753/00A patent/AU1375300A/en not_active Abandoned
-
2000
- 2000-10-20 WO PCT/DK2000/000586 patent/WO2001030742A1/en active IP Right Grant
- 2000-10-20 AU AU79025/00A patent/AU7902500A/en not_active Abandoned
- 2000-10-20 DK DK00969235T patent/DK1224159T3/da active
- 2000-10-20 EP EP00969235A patent/EP1224159B1/en not_active Expired - Lifetime
- 2000-10-20 AT AT00969235T patent/ATE260237T1/de not_active IP Right Cessation
-
2001
- 2001-06-06 ZA ZA200104630A patent/ZA200104630B/xx unknown
-
2002
- 2002-04-26 NO NO20021994A patent/NO319078B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| UA71939C2 (en) | 2005-01-17 |
| EA004371B1 (ru) | 2004-04-29 |
| DE69927842D1 (de) | 2005-11-24 |
| CA2351401C (en) | 2005-11-22 |
| CA2351401A1 (en) | 2000-06-02 |
| EP1133241A1 (en) | 2001-09-19 |
| WO2000025598A1 (en) | 2000-05-11 |
| NO20021994D0 (no) | 2002-04-26 |
| NO20021994L (no) | 2002-04-26 |
| EP1224159B1 (en) | 2004-02-25 |
| WO2000030465A1 (en) | 2000-06-02 |
| EP1133241B1 (en) | 2005-10-19 |
| DE69927842T2 (de) | 2006-07-27 |
| ATE260237T1 (de) | 2004-03-15 |
| ZA200104630B (en) | 2002-11-27 |
| AU1031500A (en) | 2000-05-22 |
| EA200100582A1 (ru) | 2001-12-24 |
| ATE306824T1 (de) | 2005-11-15 |
| AU7902500A (en) | 2001-05-08 |
| ES2249064T3 (es) | 2006-03-16 |
| AU1375300A (en) | 2000-06-13 |
| WO2001030742A1 (en) | 2001-05-03 |
| US6787167B1 (en) | 2004-09-07 |
| EE200100274A (et) | 2002-10-15 |
| EP1224159A1 (en) | 2002-07-24 |
| DK1133241T3 (da) | 2006-02-13 |
| EE04794B1 (et) | 2007-04-16 |
| DK1224159T3 (da) | 2004-06-28 |
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