NO319078B1 - Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen - Google Patents

Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen Download PDF

Info

Publication number: NO319078B1
Authority: NO; Norway
Prior art keywords: dichlorophenyl; compound; formula; methyl; cis
Prior art date: 1998-11-23

Application number

NO20021994A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021994D0 (no

NO20021994L (no

Inventor

Soeren Bols Pedersen

Erik Fischer

Svend Peter Treppendahl

Original Assignee

Hexal As

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.)

1998-11-23

Filing date

2002-04-26

Publication date

2005-06-13

2002-04-26 Application filed by Hexal As filed Critical Hexal As

2002-04-26 Publication of NO20021994D0 publication Critical patent/NO20021994D0/no

2002-04-26 Publication of NO20021994L publication Critical patent/NO20021994L/no

2005-06-13 Publication of NO319078B1 publication Critical patent/NO319078B1/no

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)
Saccharide Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)

NO20021994A 1998-11-23 2002-04-26 Fremgangsmate for fremstilling av racemisk sertralin, samt mellomprodukter ved fremstillingen NO319078B1 (no)

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 (de)
EP (2)	EP1133241B1 (de)
AT (2)	ATE306824T1 (de)
AU (3)	AU1031500A (de)
CA (1)	CA2351401C (de)
DE (1)	DE69927842T2 (de)
DK (2)	DK1133241T3 (de)
EA (1)	EA004371B1 (de)
EE (1)	EE04794B1 (de)
ES (1)	ES2249064T3 (de)
NO (1)	NO319078B1 (de)
UA (1)	UA71939C2 (de)
WO (3)	WO2000025598A1 (de)
ZA (1)	ZA200104630B (de)

Families Citing this family (67)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA72206C2 (en) *	1998-03-04	2005-02-15	Dandy S	Coated chewing gum, method of obtaining thereof and using one or several active ingredients in solid form
KR20070002101A (ko)	2000-03-14	2007-01-04	테바 파마슈티컬 인더스트리즈 리미티드	(+)-시스-세르트랄린의 신규한 제조 방법
EP1922937A3 (de)	2001-03-23	2008-06-04	Gumlink A/S	Beschichtetes und abbaubares Kaugummi mit verlängerter Haltbarkeit und Herstellungsverfahren dafür
DE60230020D1 (de)	2001-03-23	2009-01-08	Gumlinck As	Beschichteter, abbaubarer kaugummi mit verbesserter haltbarkeit sowie verfahren zu seiner herstellung
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
AU2003251290A1 (en)	2002-04-29	2003-11-17	Teva Pharmaceutical Industries Ltd.	Process for preparation of polymorphic form ii of sertraline hydrochloride, pharmaceutical formulations and methods of administration thereof
CN1668206A (zh) *	2002-09-24	2005-09-14	古木林科有限公司	改进口香糖成分释放的口香糖
WO2004028268A1 (en) *	2002-09-24	2004-04-08	Gumlink A/S	Chewing gum comprising at least two different biodegradable polymers
WO2004028266A1 (en)	2002-09-24	2004-04-08	Gumlink A/S	Biodegradable chewing gum comprising at least one high molecular weight biodegradable polymer
EP1599100A2 (de) *	2003-03-03	2005-11-30	Wm. Wrigley Jr. Company	Überzug für süsswaren mit schneller geschmacksabgabe
MXPA05011038A (es)	2003-04-14	2006-01-24	Teva Pharma	Hidrogenacion de compuestos intermedios de imina de sertralina con catalizadores.
CA2537804A1 (en) *	2003-09-05	2005-03-17	Teva Pharmaceutical Industries Ltd	A 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
DK1765304T4 (da)	2004-07-06	2019-06-03	Fertin Pharma As	Komprimattyggegummitablet
AU2004323874A1 (en)	2004-10-08	2006-04-13	Gumlink A/S	Confectionery product
WO2006058536A1 (en)	2004-11-30	2006-06-08	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
DK1976391T3 (da)	2005-12-30	2011-01-10	Cadbury Holdings Ltd	Tyggegummipræparat indeholdende aroniabær
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.@
US8574643B2 (en)	2006-04-28	2013-11-05	Intercontinental Great Brands Llc	Transparent confectionery product
MX2009002217A (es)	2006-09-29	2009-04-16	Cadbury Holdings Ltd	Goma de mascar que comprende polietileno.
MX2009004202A (es) *	2006-10-20	2009-07-08	Wrigley W M Jun Co	Aparato y metodo para fabricar un producto de confiteria con centro relleno.
FR2909376A1 (fr) *	2006-11-30	2008-06-06	Cerep Sa	Procedes de preparation de la desmethulsertraline ou d'un de ses sels pharmaceutiquement acceptables
EP2682002A1 (de)	2007-05-31	2014-01-08	Gumlink A/S	Umweltfreundlicher Kaugummi
MD3856G2 (ro) *	2007-11-23	2009-10-31	Валериу ФАЛА	Gumă de mestecat (variante)
WO2009080022A1 (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
WO2009080021A1 (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)
EP2282645B1 (de)	2008-05-26	2015-04-15	Fertin Pharma A/S	Geschmacksimprägnierung eines kaugummikerns
US8722117B2 (en) *	2008-06-04	2014-05-13	Wm. Wrigley Jr. Company	Method and apparatus for thermal sealing a filled confectionery product
DK2442668T3 (en)	2009-06-19	2016-12-12	Fertin Pharma As	Buffered RUBBER 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
DK2654738T3 (en)	2010-12-21	2018-07-23	Fertin Pharma As	CHEESE GUM COMPOSITION COMPREHENSIVE CROSS-POLYACRYLIC ACID
BR112014011933B1 (pt)	2011-11-17	2021-06-01	Wm. Wrigley Jr. Company	Composições de goma de mascar com base em pós de fruta seca
EP2793849A1 (de)	2011-12-22	2014-10-29	Fertin Pharma A/S	Verfahren zur freisetzung von nicotin aus kaugummi
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
US20150313847A1 (en)	2012-12-07	2015-11-05	Gumlink A/S	Compressed Tablets
US20160000125A1 (en) *	2013-03-14	2016-01-07	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
WO2016136250A1 (ja) *	2015-02-27	2016-09-01	株式会社ロッテ	チューインガム
CN108366576A (zh) *	2015-11-30	2018-08-03	Wm.雷格利Jr.公司	具有表面特征的口香糖和压制薄荷糖
WO2017182084A1 (en)	2016-04-21	2017-10-26	Fertin Pharma A/S	Nicotine delivery product, related uses and oral dosage forms, and methods of production
WO2018057836A1 (en) *	2016-09-23	2018-03-29	Wm. Wrigley Jr. Company	Stable flavor compositions containing mint leaves
ES2860802T3 (es)	2016-11-18	2021-10-05	Fertin Pharma As	Comprimido que comprende un aglutinante separado y eritritol
CN109963553B (zh)	2016-11-18	2022-11-22	费尔廷制药公司	经口递送载剂
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
ES2951848T3 (es)	2018-05-17	2023-10-25	Fertin Pharma As	Un chicle en comprimidos adecuado para principios farmacéuticos activos ingredientes
US20190350858A1 (en)	2018-05-17	2019-11-21	Fertin Pharma A/S	Oral tablet for delivery of active ingredients to the gastrointestinal tract
US11135157B2 (en)	2018-05-17	2021-10-05	Fertin Pharma A/S	Oral tablet for delivery of active ingredients to the throat
US11096894B2 (en)	2018-05-17	2021-08-24	Fertin Pharma A/S	Oral tablet for induced saliva generation
US11058641B2 (en)	2018-05-17	2021-07-13	Fertin Pharma A/S	Oral tablet for taste masking of active ingredients
US11096895B2 (en)	2018-05-17	2021-08-24	Fertin Pharma A/S	Oral tablet suitable for active pharmaceutical ingredients
US11052047B2 (en)	2018-05-17	2021-07-06	Fertin Pharma A/S	Oral tablet suitable for fast release of active pharmaceutical ingredients
GB201904767D0 (en)	2019-04-04	2019-05-22	Orexo Ab	New pharmaceutical compositions
US12257346B2 (en)	2020-05-08	2025-03-25	Fertin Pharma A/S	Oral powder mixture with small sized particles
US20230123099A1 (en)	2021-10-15	2023-04-20	Fertin Pharma A/S	Dextrose tablets with improved mouthfeel
CA3260936A1 (en)	2022-06-30	2024-01-04	Fertin Pharma A/S	FLOWING SET WITH COMPOSITION FOR IMPROVED TASTE MASKING OF ACTIVE AGENTS
WO2025002519A1 (en)	2023-06-29	2025-01-02	Fertin Pharma A/S	Oral tablet with improved uniformity of content of actives
DK202330347A1 (en)	2023-11-25	2025-06-12	Fertin Pharma As	Coated soft chew tablets suitable for antacids

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB711187A (en)	1952-03-29	1954-06-23	Edgar Victor Johnson	Improvements in or relating to chewing gum
US3632358A (en)	1968-04-18	1972-01-04	Philip Morris Inc	Chewing gum with freeze-dried food particles
US3795744A (en)	1970-10-21	1974-03-05	Lotte Co Ltd	Flavor variable chewing gum and methods of preparing the same
US3962463A (en) *	1972-04-03	1976-06-08	Life Savers, Inc.	Chewing gum having surface impregnated, microencapsulated flavor particles
US4250195A (en)	1979-09-24	1981-02-10	Life Savers, Inc.	Method for applying soft flexible sugar coating to fresh chewing gum and coated chewing gum product
US4317838A (en) *	1979-09-24	1982-03-02	Life Savers, Inc.	Method for applying sugarless coating to chewing gum and confections
US4536518A (en) *	1979-11-01	1985-08-20	Pfizer Inc.	Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine
US4385071A (en)	1981-08-10	1983-05-24	Donna Yakimischak	Chewing gum flavor combination
NL8600050A (nl) *	1986-01-13	1987-08-03	Sanico Nv	Farmaceutisch preparaat met vertraagde afgifte van het werkzame bestanddeel en werkwijze voor de bereiding er van.
US4803082A (en)	1987-10-28	1989-02-07	Warner-Lambert Company	Flavor and sweetness enhancement delivery systems and method of preparation
US4938971A (en)	1988-06-29	1990-07-03	Wm. Wrigley Jr. Company	Fluid fruit juice and edible plasticizer composition having low moisture content
CA1332533C (en) *	1988-11-04	1994-10-18	Albert H. Chapdelaine	Emulsifiers for flavor prolongation in chewing gum
US5057328A (en) *	1988-11-14	1991-10-15	Warner-Lambert Company	Food acid delivery systems containing polyvinyl acetate
WO1990006689A1 (en)	1989-05-17	1990-06-28	Wm. Wrigley Jr. Company	Use of spice ingredients to enhance flavor duration of chewing gum
EP0414932A1 (de)	1989-08-29	1991-03-06	Csemege Edesipari Gyar	Kaugummimasse
GR1000987B (el)	1989-10-10	1993-03-31	Warner Labert Company	Συμπυκνωμα χυμου φρουτων σε τσιχλα.
FI905333A7 (fi) *	1989-10-31	1991-05-01	Warner Lambert Co	Kapseloitu antosysteemi makeutus- ja aromiaineita varten ja menetelmä sen valmistamiseksi
CA2070061C (en) *	1991-06-07	2004-02-10	Shigeyuki Takama	Physiologically active polypeptide-containing pharmaceutical composition
GB9114948D0 (en) *	1991-07-11	1991-08-28	Pfizer Ltd	Process for preparing sertraline intermediates
NZ243667A (en)	1991-08-02	1995-02-24	Kurihara Yoshie	Chewing gum containing coated curculin derivative or fruit containing curculin
DE69230807T2 (de)	1991-11-12	2000-07-06	Wm. Wrigley Jr. Co., Chicago	Nichtklebender kaugummi mit hoher aromaintensität und verminderter plastifizierung
US5334397A (en)	1992-07-14	1994-08-02	Amurol Products Company	Bubble gum formulation
US5320854A (en)	1992-12-16	1994-06-14	Wm. Wrigley Jr. Company	Chewing gum containing stabilized hygroscopic ingredients
JPH09501311A (ja)	1993-06-23	1997-02-10	ダブリューエムリグリージュニアカンパニー	改良されたチューイングガムおよびキャンディー製品
PH31445A (en)	1994-04-12	1998-11-03	Wrigley W M Jun Co	Fruit flavored chewing gum with prolonged flavor intensity.
US5529783A (en) *	1994-12-19	1996-06-25	Mcneil-Ppc, Inc.	Rotor granulation and coating of acetaminophen, pseudoephedrine, chlorpheniramine, and, optionally dextromethorphan
WO1997000619A1 (en) *	1995-06-20	1997-01-09	Wm. Wrigley Jr. Company	Improved chewing gum containing sucrose fatty acid esters
FR2777000B1 (fr) *	1998-04-01	2002-09-27	Catalys	Procede de preparation de la sertraline racemique
US7375087B2 (en)	2002-08-08	2008-05-20	Kissei Pharmaceutical Co., Ltd.	Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
RU2214297C1 (ru)	2002-09-18	2003-10-20	Подобедов Александр Васильевич	Способ перегонки жидкости и устройство для его осуществления
EP3094084A1 (de)	2005-08-10	2016-11-16	Mitsubishi Electric Corporation	Aufzeichnungsmedium, wiedergabevorrichtung und wiedergabeverfahren

1999
- 1999-11-03 AU AU10315/00A patent/AU1031500A/en not_active Abandoned
- 1999-11-03 WO PCT/DK1999/000598 patent/WO2000025598A1/en not_active Ceased
- 1999-11-23 AU AU13753/00A patent/AU1375300A/en not_active Abandoned
- 1999-11-23 WO PCT/DK1999/000649 patent/WO2000030465A1/en not_active Ceased
- 1999-11-23 EE EEP200100274A patent/EE04794B1/xx not_active IP Right Cessation
- 1999-11-23 US US09/856,540 patent/US6787167B1/en not_active Expired - Fee Related
- 1999-11-23 AT AT99972499T patent/ATE306824T1/de not_active IP Right Cessation
- 1999-11-23 UA UA2001064422A patent/UA71939C2/uk unknown
- 1999-11-23 DK DK99972499T patent/DK1133241T3/da active
- 1999-11-23 CA CA002351401A patent/CA2351401C/en not_active Expired - Fee Related
- 1999-11-23 DE DE69927842T patent/DE69927842T2/de not_active Expired - Lifetime
- 1999-11-23 EA EA200100582A patent/EA004371B1/ru not_active IP Right Cessation
- 1999-11-23 ES ES99972499T patent/ES2249064T3/es not_active Expired - Lifetime
- 1999-11-23 EP EP99972499A patent/EP1133241B1/de not_active Expired - Lifetime
2000
- 2000-10-20 EP EP00969235A patent/EP1224159B1/de not_active Expired - Lifetime
- 2000-10-20 AU AU79025/00A patent/AU7902500A/en not_active Abandoned
- 2000-10-20 WO PCT/DK2000/000586 patent/WO2001030742A1/en not_active Ceased
- 2000-10-20 AT AT00969235T patent/ATE260237T1/de not_active IP Right Cessation
- 2000-10-20 DK DK00969235T patent/DK1224159T3/da active
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
EP1224159A1 (de)	2002-07-24
CA2351401C (en)	2005-11-22
ZA200104630B (en)	2002-11-27
EE04794B1 (et)	2007-04-16
EP1133241B1 (de)	2005-10-19
CA2351401A1 (en)	2000-06-02
EP1224159B1 (de)	2004-02-25
US6787167B1 (en)	2004-09-07
EP1133241A1 (de)	2001-09-19
WO2000025598A1 (en)	2000-05-11
EA004371B1 (ru)	2004-04-29
AU7902500A (en)	2001-05-08
DE69927842D1 (de)	2005-11-24
NO20021994D0 (no)	2002-04-26
NO20021994L (no)	2002-04-26
DE69927842T2 (de)	2006-07-27
ES2249064T3 (es)	2006-03-16
ATE260237T1 (de)	2004-03-15
WO2000030465A1 (en)	2000-06-02
DK1133241T3 (da)	2006-02-13
WO2001030742A1 (en)	2001-05-03
AU1375300A (en)	2000-06-13
EA200100582A1 (ru)	2001-12-24
DK1224159T3 (da)	2004-06-28
AU1031500A (en)	2000-05-22
EE200100274A (et)	2002-10-15
ATE306824T1 (de)	2005-11-15

Legal Events

Date	Code	Title	Description
2010-05-31	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP1224159B1 (de)	2004-02-25	Racemisch sertralin synthese
EP0030081B1 (de)	1983-03-02	Antidepressiv wirkende Derivate des cis-4-Phenyl-1,2,3,4-tetrahydro-1-naphthalin-amins und pharmazeutische Zusammensetzungen daraus
EP0028901B1 (de)	1983-03-02	Antidepressiv wirkende Derivate des trans-4-Phenyl-1,2,3,4-tetrahydro-1-naphthalin-amins und pharmazeutische Zusammensetzungen daraus
IE70061B1 (en)	1996-10-16	Process of recycling amine isomer
US7893262B2 (en)	2011-02-22	Process for the preparation of 2H-chromenes
US7361770B2 (en)	2008-04-22	Process for preparation of valsartan
PL192489B1 (pl)	2006-10-31	Nowy sposób wytwarzania ketiminy
US20090253746A1 (en)	2009-10-08	Synthesis and Preparations of Intermediates and New Polymorphs Thereof Useful For The Preparation Of Donepezil Hydrochlcoride
DK174219B1 (da)	2002-09-30	Forbedret syntese af racemisk sertralin
US20120253051A1 (en)	2012-10-04	Process for the preparation of ropinirole and salts thereof
NO173541B (no)	1993-09-20	Analogifremgangsmaate for fremstilling av terapeutisk aktive polycykliske aminer
WO2003099761A1 (en)	2003-12-04	Process for the manufacture of sertraline
US7345201B2 (en)	2008-03-18	Processes for preparing sertraline
NO176516B (no)	1995-01-09	Fremgangsmåte for fremstilling av et farmasöytisk mellomprodukt, utgangsmateriale for fremstilling derav, og anvendelse ved videre fremstilling
US20070260090A1 (en)	2007-11-08	Highly Steroselective Synthesis of Sertraline
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