FI63754C - Foerfarande foer framstaellning av en terapeutiskt anvaendbar ftalan - Google Patents
Foerfarande foer framstaellning av en terapeutiskt anvaendbar ftalan Download PDFInfo
- Publication number
- FI63754C FI63754C FI770073A FI770073A FI63754C FI 63754 C FI63754 C FI 63754C FI 770073 A FI770073 A FI 770073A FI 770073 A FI770073 A FI 770073A FI 63754 C FI63754 C FI 63754C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- cyano
- dimethylaminopropyl
- trifluoromethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 15
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 n -propanoyl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 4
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 7
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- 238000010171 animal model Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 210000001772 blood platelet Anatomy 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YKOAIJCWPZQIQX-UHFFFAOYSA-N 1-[4-bromo-2-(hydroxymethyl)phenyl]-1-(4-chlorophenyl)-4-(dimethylamino)butan-1-ol Chemical compound C=1C=C(Br)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(Cl)C=C1 YKOAIJCWPZQIQX-UHFFFAOYSA-N 0.000 description 2
- WOLPGGGWZDXCNM-UHFFFAOYSA-N 3-[5-bromo-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical compound O1CC2=CC(Br)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WOLPGGGWZDXCNM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000000966 norepinephrine reuptake Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 1
- 210000002348 5-ht neuron Anatomy 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- VPWZLPOILJLUND-UHFFFAOYSA-N [4-bromo-2-(hydroxymethyl)phenyl]-(4-chlorophenyl)methanone Chemical compound OCC1=CC(Br)=CC=C1C(=O)C1=CC=C(Cl)C=C1 VPWZLPOILJLUND-UHFFFAOYSA-N 0.000 description 1
- GCJYYUGXODRJJT-UHFFFAOYSA-N [4-bromo-2-(hydroxymethyl)phenyl]-(4-fluorophenyl)methanol Chemical compound OCC1=CC(Br)=CC=C1C(O)C1=CC=C(F)C=C1 GCJYYUGXODRJJT-UHFFFAOYSA-N 0.000 description 1
- DSXGDABDEZITPU-UHFFFAOYSA-N [4-bromo-2-(hydroxymethyl)phenyl]-(4-fluorophenyl)methanone Chemical compound OCC1=CC(Br)=CC=C1C(=O)C1=CC=C(F)C=C1 DSXGDABDEZITPU-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
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- 230000037007 arousal Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
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- 230000000994 depressogenic effect Effects 0.000 description 1
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- 238000002635 electroconvulsive therapy Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- 229940093915 gynecological organic acid Drugs 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- NGPAITITALWALP-UHFFFAOYSA-M magnesium;n,n-dimethylpropan-1-amine;chloride Chemical compound [Mg+2].[Cl-].CN(C)CC[CH2-] NGPAITITALWALP-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 229960003057 nialamide Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB148676 | 1976-01-14 | ||
| GB1486/76A GB1526331A (en) | 1976-01-14 | 1976-01-14 | Phthalanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI770073A7 FI770073A7 (cs) | 1977-07-15 |
| FI63754B FI63754B (fi) | 1983-04-29 |
| FI63754C true FI63754C (fi) | 1983-08-10 |
Family
ID=9722860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI770073A FI63754C (fi) | 1976-01-14 | 1977-01-11 | Foerfarande foer framstaellning av en terapeutiskt anvaendbar ftalan |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4136193A (cs) |
| JP (1) | JPS52105162A (cs) |
| AT (1) | AT359488B (cs) |
| AU (1) | AU509445B2 (cs) |
| BE (1) | BE850401A (cs) |
| CA (1) | CA1094087A (cs) |
| CH (3) | CH626886A5 (cs) |
| DE (1) | DE2657013C2 (cs) |
| DK (1) | DK143275C (cs) |
| ES (1) | ES454980A1 (cs) |
| FI (1) | FI63754C (cs) |
| FR (1) | FR2338271A1 (cs) |
| GB (1) | GB1526331A (cs) |
| IE (1) | IE44055B1 (cs) |
| NL (2) | NL192451C (cs) |
| NO (2) | NO147243C (cs) |
| NZ (1) | NZ183001A (cs) |
| SE (1) | SE429551B (cs) |
| ZA (1) | ZA7757B (cs) |
Families Citing this family (162)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4602035A (en) * | 1983-12-07 | 1986-07-22 | Hoechst-Roussel Pharmaceuticals Inc. | Antidepressant (3-aryl-2,3-dihydrobenzofuran-3-yl)alkylamines |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| EP0759299B1 (en) * | 1995-08-16 | 2000-04-26 | Eli Lilly And Company | Potentiation of serotonin response |
| ATE205824T1 (de) * | 1997-07-08 | 2001-10-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| BR9714925A (pt) | 1997-11-11 | 2003-07-22 | Lundbeck & Co As H | Método para preparação de citalopran, composto e composição farmacêutica antidepressiva |
| WO2000023431A1 (en) | 1998-10-20 | 2000-04-27 | H. Lundbeck A/S | Method for the preparation of citalopram |
| AR021509A1 (es) * | 1998-12-08 | 2002-07-24 | Lundbeck & Co As H | Derivados de benzofurano, su preparacion y uso |
| KR20010081071A (ko) | 1998-12-08 | 2001-08-25 | 피터슨 존 메이달 | 벤조푸란 유도체, 그것들의 제조 및 사용 |
| EP1140886B1 (en) | 1998-12-23 | 2003-04-02 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| TR200102957T2 (tr) * | 1999-04-14 | 2004-12-21 | H. Lundbeck A/S | Sitalopram hazırlanması için metod. |
| ITMI991579A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991486A1 (it) * | 1999-07-06 | 2001-01-06 | Vis Farmaceutici S P A | Processo per la sintesi di citalopram |
| AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| TR200101874T1 (tr) * | 1999-10-25 | 2002-02-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem |
| ATE277032T1 (de) | 1999-10-25 | 2004-10-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| US6310222B1 (en) * | 1999-11-01 | 2001-10-30 | Sumika Fine Chemicals Co., Ltd. | Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| EA004742B1 (ru) | 1999-12-28 | 2004-08-26 | Х.Лундбекк А/С | Способ получения циталопрама |
| HUP0203840A3 (en) * | 1999-12-30 | 2005-02-28 | Lundbeck & Co As H | Method for the preparation of citalopram |
| HK1054392B (zh) * | 2000-01-14 | 2005-11-18 | H‧隆德贝克有限公司 | 製備5-氰基2-苯並[c]呋喃酮的方法 |
| US6433196B1 (en) | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| NL1017415C1 (nl) * | 2000-02-24 | 2001-05-18 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| IES20010143A2 (en) * | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| BR0109176A (pt) | 2000-03-13 | 2003-04-22 | Lundbeck & Co As H | Método para preparação de citalopram e composto da fórmula |
| EP1265881A1 (en) * | 2000-03-13 | 2002-12-18 | H. Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| KR20020080476A (ko) | 2000-03-14 | 2002-10-23 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조 방법 |
| IL151487A0 (en) * | 2000-03-16 | 2003-04-10 | Lundbeck & Co As H | Method for the preparation of 5-cyano-1-(4-flourophenyl)-1,3-dihydroisobenzofurans |
| CA2406383A1 (en) * | 2000-04-13 | 2001-10-25 | Mayo Foundation For Medical Education And Research | A.beta.42 lowering agents |
| US6977306B2 (en) | 2000-05-02 | 2005-12-20 | Sumitomo Chemical Company, Limited | Citalopram hydrobromide crystal and method for crystallization thereof |
| AR032455A1 (es) | 2000-05-12 | 2003-11-12 | Lundbeck & Co As H | Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva |
| KR100821912B1 (ko) * | 2000-05-12 | 2008-04-16 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조 방법 |
| WO2002004435A1 (en) * | 2000-07-06 | 2002-01-17 | H. Lundbeck A/S | Method for the preparation of citalopram |
| NZ523720A (en) * | 2000-07-21 | 2004-07-30 | H | Novel compounds and their use as glycine transport inhibitors |
| CA2353693C (en) * | 2000-08-10 | 2003-07-22 | H. Lundbeck A/S | Pharmaceutical composition containing citalopram |
| CA2354877C (en) * | 2000-08-18 | 2006-05-02 | H. Lundbeck A/S | Method for the preparation of citalopram |
| US20030232881A1 (en) * | 2000-10-27 | 2003-12-18 | H. Lundbeck A/S | Crystals of pharmaceutically acceptable salts of citalopram, methods of crystallization, and pharmaceutical compositions comprising them |
| US20030109577A1 (en) * | 2000-10-27 | 2003-06-12 | Ken Liljegren | Pharmaceutical composition containing citalopram |
| IT1319686B1 (it) * | 2000-12-12 | 2003-10-23 | C D Farmasint S R L | Procedimento di preparazione di citalopram. |
| IL147226A (en) * | 2000-12-22 | 2006-04-10 | Lundbeck & Co As H | Process for the preparation of pure citalopram |
| EA003459B1 (ru) * | 2000-12-28 | 2003-06-26 | Х.Лундбекк А/С | Способ получения чистого циталопрама |
| DE10112828C1 (de) * | 2000-12-28 | 2002-11-21 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| DE10164725B4 (de) * | 2000-12-28 | 2004-08-26 | H. Lundbeck A/S | Verfahren zur Herstellung von gereinigtem Citalopram |
| AU2001100195B4 (en) * | 2001-01-05 | 2001-12-20 | H Lundbeck As | Pharmaceutical composition containing citalopram. |
| WO2002060886A1 (en) * | 2001-01-30 | 2002-08-08 | Orion Corporation, Fermion | Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile |
| CN1492861A (zh) * | 2001-02-22 | 2004-04-28 | 纳特科药品有限公司 | 西酞普兰的制备方法 |
| GB0105627D0 (en) * | 2001-03-07 | 2001-04-25 | Cipla Ltd | Preparation of phthalanes |
| HRP20030811A2 (en) * | 2001-03-09 | 2005-08-31 | Ranbaxy Laboratories Limited | Process for the preparation of citalopram |
| SK14612003A3 (sk) * | 2001-05-01 | 2004-04-06 | H. Lundbeck A/S | Použitie enantiomérne čistého escitalopramu a farmaceutický prostriedok s obsahom escitalopramu |
| BG65271B1 (bg) * | 2001-06-18 | 2007-11-30 | H. Lundbeck A/S | Метод за получаване на циталопрам |
| AR034759A1 (es) * | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | Metodo para la preparacion de escitalopram |
| IN192057B (cs) * | 2001-07-19 | 2004-02-14 | Ranbaxy Lab Ltd | |
| HRP20031073A2 (en) * | 2001-07-31 | 2004-04-30 | Lundbeck & Co As H | Crystalline composition containing escitalopram |
| EP1288211A1 (en) * | 2001-08-28 | 2003-03-05 | Sekhsaria Chemicals Ltd. | Improved process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| US6967259B2 (en) * | 2001-09-24 | 2005-11-22 | Pharmachem Technologies Limited | Process for the preparation of Citalopram intermediate |
| WO2003031407A2 (en) * | 2001-10-12 | 2003-04-17 | Serenix Pharmaceuticals, Llc | β-LACTAMYL VASOPRESSIN VlaANTAGONISTS |
| IN192863B (cs) * | 2001-11-13 | 2004-05-22 | Ranbaxy Lab Ltd | |
| IS7239A (is) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| US7148364B2 (en) * | 2002-01-07 | 2006-12-12 | Sun Pharmaceutical Industries | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile |
| GB2387596B (en) * | 2002-02-27 | 2004-02-11 | Matrix Lab Ltd | Process |
| GB0204607D0 (en) * | 2002-02-27 | 2002-04-10 | Matrix Lab Ltd | Process |
| GB2385848A (en) * | 2002-02-27 | 2003-09-03 | Cipla Ltd | Citalopram salts |
| EP1346989A1 (en) * | 2002-03-21 | 2003-09-24 | Jubilant Organosys Limited | Improved process for the preparation of citalopram and its hydrobromide |
| WO2003080558A1 (fr) * | 2002-03-27 | 2003-10-02 | Bando Chemical Industries, Ltd. | Nouveau 1,3,5-tris(arylamino)benzène |
| CA2381341A1 (en) * | 2002-04-09 | 2003-10-09 | Torcan Chemical Ltd. | Process and intermediates for preparing escitalopram |
| FI20021421A0 (fi) * | 2002-07-30 | 2002-07-30 | Orion Corp Fermion | Valmistusmenetelmä |
| AR040970A1 (es) * | 2002-08-12 | 2005-04-27 | Lundbeck & Co As H | Metodo para la separacion de intermediarios que pueden ser utilizados para la preparacion de escitalopram |
| WO2004016602A1 (en) * | 2002-08-14 | 2004-02-26 | Natco Pharma Limited | Process for the preparation of high purity citalopram and its pharmaceutically acceptable salts |
| GB2385051B (en) * | 2002-08-29 | 2003-12-24 | Max India Ltd | Improved process for the preparation of 5-substituted-1 (4-fluorophenyl)-1,3-dihydro isobenzofurans |
| US6812355B2 (en) | 2002-10-22 | 2004-11-02 | Sekhsaria Chemicals Limited | Process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| US20050137255A1 (en) * | 2002-12-23 | 2005-06-23 | H. Lundbeck A/S | Crystalline escitalopram hydrobromide and methods for preparing the same |
| RS51092B (sr) * | 2002-12-23 | 2010-10-31 | H. Lundbeck A/S. | Escitalopram bromhidrat i postupak za njegovo pripremanje |
| AU2003242990A1 (en) * | 2003-01-17 | 2004-08-13 | Pulla Reddy Muddasani | Processes for the preparation of escitalopram and its precursor |
| EP1603548A4 (en) * | 2003-02-05 | 2007-10-10 | Myriad Genetics Inc | METHOD AND COMPOSITION FOR THE TREATMENT OF NEURODEEGENERATIVE DISEASES |
| ITMI20030479A1 (it) * | 2003-03-13 | 2004-09-14 | Adorkem Technology S P A | Procedimento per la preparazione di un ciano-isobenzofurano. |
| EP1486492A3 (en) * | 2003-06-10 | 2005-02-23 | Sun Pharmaceuticals Industries Ltd. | A process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran. |
| JP2007528857A (ja) * | 2003-07-11 | 2007-10-18 | ミリアド ジェネティクス， インコーポレイテッド | アルツハイマー病の処置のための薬学的方法、投与レジメンおよび投薬形態 |
| GB0317475D0 (en) * | 2003-07-25 | 2003-08-27 | Meditab Specialities Pvt Ltd | Product |
| ITFI20030202A1 (it) * | 2003-07-28 | 2005-01-29 | Synteco Spa | Processo per la preparazione di derivati del |
| PT1668014E (pt) * | 2003-09-17 | 2009-03-17 | Janssen Pharmaceutica Nv | Compostos heterocíclicos fundidos como moduladores do receptor de serotonina |
| SI1506963T1 (en) * | 2003-10-28 | 2005-10-31 | Adorkem Technology Spa | Method for the preparation of citalopram |
| CA2546422A1 (en) * | 2003-10-28 | 2005-05-12 | Wockhardt Limited | Improved process for the manufacture of citalopram hydrobromide |
| US20050143350A1 (en) * | 2003-11-19 | 2005-06-30 | Seed John C. | Combination drug therapy to treat obesity |
| CA2547639A1 (en) * | 2003-12-02 | 2005-06-16 | B&B Beheer Nv | Use of d4 and 5-ht2a antagonists, inverse agonists or partial agonists |
| ES2515092T3 (es) | 2003-12-11 | 2014-10-29 | Sunovion Pharmaceuticals Inc. | Combinación de un sedante y un modulador neurotransmisor y métodos de mejorar la calidad del sueño y de tratar la depresión |
| CN100569765C (zh) * | 2003-12-19 | 2009-12-16 | 杭州民生药业集团有限公司 | 西酞普兰中间体晶体碱 |
| TWI339651B (en) * | 2004-02-12 | 2011-04-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
| CA2559703A1 (en) * | 2004-02-16 | 2005-08-25 | Jubilant Organosys Limited | One pot synthesis of citalopram from 5-cyanophthalide |
| US20050196453A1 (en) * | 2004-03-05 | 2005-09-08 | H. Lundbeck A/S | Crystalline composition containing escitalopram |
| ITMI20040717A1 (it) * | 2004-04-09 | 2004-07-09 | Adorkem Technology Spa | Procedimento chemo-enzimatico per la preparazione dell'escitalopram |
| US20070293538A1 (en) * | 2004-04-13 | 2007-12-20 | Myriad Genetics, Incorporated | Pharmaceutical Composition And Methods For Treating Neurodegenerative Disorders |
| EP1737473A4 (en) * | 2004-04-19 | 2009-08-26 | Noven Therapeutics Llc | COMBINATIONS OF LITHIUM AND USES THEREOF |
| WO2005108683A1 (en) * | 2004-04-29 | 2005-11-17 | Keystone Retaining Wall Systems, Inc. | Veneers for walls, retaining walls and the like |
| WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| BRPI0514303A (pt) * | 2004-08-11 | 2008-06-10 | Myriad Genetics Inc | composição farmacêutica e método para tratar distúrbios neurodegenerativos |
| US7989645B2 (en) * | 2004-08-23 | 2011-08-02 | Sun Pharma Global Fze | Process for preparation of citalopram and enantiomers |
| ES2285972T1 (es) | 2004-08-23 | 2007-12-01 | Sun Pharmaceutical Industries Limited | Procedimiento de fabricacion de citalopram y enantiomeros. |
| US9597314B2 (en) | 2005-03-22 | 2017-03-21 | Azevan Pharmaceuticals, Inc. | Beta-lactamylalkanoic acids for treating premenstrual disorders |
| WO2006103550A1 (en) * | 2005-03-31 | 2006-10-05 | Ranbaxy Laboratories Limited | Processes for the preparation of citalopram and its intermediate 5-aminophthalide |
| AR056980A1 (es) | 2005-04-22 | 2007-11-07 | Wyeth Corp | Derivados de dihidrobenzofurano, composiciones farmaceuticas, y uso de los mismos |
| CA2604759A1 (en) * | 2005-04-22 | 2006-11-02 | Wyeth | Dihydrobenzofuran derivatives and uses thereof |
| BRPI0610785A2 (pt) * | 2005-04-22 | 2016-09-13 | Wyeth Corp | polimorfo cristalino, processo para preparar o mesmo, forma cristalina, composição, e, métodos para tratar uma doença, distúrbios, e uma condição |
| CA2605554A1 (en) | 2005-04-22 | 2006-11-02 | Wyeth | Benzofuranyl alkanamine derivatives and uses thereof as 5-ht2c agonists |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| TWI358407B (en) | 2005-06-22 | 2012-02-21 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersibl |
| US20070015138A1 (en) * | 2005-07-08 | 2007-01-18 | Braincells, Inc. | Methods for identifying agents and conditions that modulate neurogenesis |
| US20070015832A1 (en) * | 2005-07-14 | 2007-01-18 | Myriad Genetics, Incorporated | Methods of treating overactive bladder and urinary incontinence |
| RU2466991C2 (ru) * | 2005-07-19 | 2012-11-20 | Эйзеван Фармасьютиклз, Инк. | β-ЛАКТАМИЛЗАМЕЩЕННЫЕ АНАЛОГИ ФЕНИЛАЛАНИНА, ЦИСТЕИНА И СЕРИНА В КАЧЕСТВЕ АНТАГОНИСТОВ ВАЗОПРЕССИНА |
| AU2006272760A1 (en) * | 2005-07-22 | 2007-02-01 | Myriad Genetics, Inc. | High drug load formulations and dosage forms |
| US7598255B2 (en) * | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| CA2625153A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| JP2009513672A (ja) | 2005-10-31 | 2009-04-02 | ブレインセルス，インコーポレイティド | 神経発生のｇａｂａ受容体媒介調節 |
| EP1951726A2 (en) * | 2005-11-14 | 2008-08-06 | H.Lundbeck A/S | Method for the preparation of escitalopram |
| GB0601286D0 (en) | 2006-01-23 | 2006-03-01 | Sandoz Ag | Asymmetric synthesis |
| FR2912057B1 (fr) * | 2007-02-07 | 2009-04-17 | Sanofi Aventis Sa | Composition pharmaceutique contenant en association le saredutant et un inhibiteur selectif de la recapture de la serotonine ou un inhibiteur de la recapture de la serotonine/norepinephrine |
| CA2643199A1 (en) * | 2006-03-08 | 2007-09-13 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US20100216734A1 (en) * | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US20070225279A1 (en) * | 2006-03-24 | 2007-09-27 | Wyeth | Therapeutic combinations for the treatment of depression |
| US7858611B2 (en) * | 2006-05-09 | 2010-12-28 | Braincells Inc. | Neurogenesis by modulating angiotensin |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| EP2026813A2 (en) * | 2006-05-09 | 2009-02-25 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| US20100009983A1 (en) * | 2006-05-09 | 2010-01-14 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| WO2008006099A2 (en) * | 2006-07-07 | 2008-01-10 | Myriad Genetics, Inc. | Treatment of psychiatric disorders |
| WO2008059514A2 (en) * | 2006-07-31 | 2008-05-22 | Cadila Healthcare Limited | Process for preparing escitalopram |
| TW200817003A (en) * | 2006-07-31 | 2008-04-16 | Sanofi Aventis | Pharmaceutical composition comprising, in combination, saredutant and a selective serotonin peuptake inhibitor or a serotonin/norepinephrine reuptake inhibitor |
| MX2009002496A (es) * | 2006-09-08 | 2009-07-10 | Braincells Inc | Combinaciones que contienen un derivado de 4-acilaminopiridina. |
| WO2008034032A2 (en) * | 2006-09-14 | 2008-03-20 | Azevan Pharmaceuticals, Inc. | Beta-lactam cannabinoid receptor modulators |
| CA2663347A1 (en) * | 2006-09-19 | 2008-03-27 | Braincells, Inc. | Ppar mediated modulation of neurogenesis |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| JP4927497B2 (ja) * | 2006-10-25 | 2012-05-09 | 株式会社シスコ | 無湿乾燥用ホッパー装置 |
| CN100457747C (zh) * | 2006-11-21 | 2009-02-04 | 浙江大学 | 抗抑郁药西酞普兰关键中间体5-氰基苯酞的制备工艺 |
| US20080167363A1 (en) * | 2006-12-28 | 2008-07-10 | Braincells, Inc | Modulation of Neurogenesis By Melatoninergic Agents |
| EP2125017A2 (en) * | 2007-01-11 | 2009-12-02 | Braincells, Inc. | Modulation of neurogenesis with use of modafinil |
| US7566793B2 (en) * | 2007-04-23 | 2009-07-28 | Synthon Bv | Process for resolving citalopram |
| WO2008142379A2 (en) * | 2007-05-18 | 2008-11-27 | Cipla Limited | Process for the preparation of escitalopram via desmethylcitalopram, optical resolution and methylation of the s-isomer |
| US20080312318A1 (en) * | 2007-06-14 | 2008-12-18 | Protia, Llc | Deuterium-enriched escitalopram |
| EP2017271A1 (en) | 2007-07-06 | 2009-01-21 | Aurobindo Pharma Limited | Process for the preparation of escitalopram |
| US8022232B2 (en) * | 2007-09-11 | 2011-09-20 | H. Lundbeck A/S | Method for manufacture of escitalopram |
| KR101103118B1 (ko) * | 2007-11-02 | 2012-01-04 | 동아제약주식회사 | 신규한 1,3-디히드로-5-이소벤조퓨란카르보니트릴 유도체 화합물 및 이를 함유하는 조루증 치료용 약학조성물 |
| US20110034565A1 (en) | 2008-04-18 | 2011-02-10 | University College Dublin, National University Of Ireland, Dublin | Psycho-pharmaceuticals |
| EP2116231A1 (en) | 2008-05-07 | 2009-11-11 | Hexal Ag | Granulate comprising escitalopram oxalate |
| US20100087664A1 (en) * | 2008-10-07 | 2010-04-08 | Ravindra Vedantham | Preparation of citalopram and salts thereof |
| GR20080100696A (el) | 2008-10-23 | 2010-05-13 | Genepharm �.�. | Φαρμακοτεχνικη μορφη με βελτιωμενη γευση του φαρμακευτικα αποδεκτου αλατος εσιταλοπραμης |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| PH12012500796A1 (en) | 2009-10-23 | 2012-11-26 | Janssen Pharmaceutica Nv | Disubstituted octahydropyrrolo [3,4-c] pyrroles as orexin receptor modulators |
| JP2013535425A (ja) | 2010-07-01 | 2013-09-12 | アゼヴァン ファーマシューティカルズ，インコーポレイテッド | 心的外傷後ストレス障害を治療する方法 |
| WO2013081567A1 (en) | 2011-12-02 | 2013-06-06 | Mahmut Bilgic | Effervescent antipsychotic formulations |
| WO2013100870A1 (en) | 2011-12-02 | 2013-07-04 | Mahmut Bilgic | New antipsychotic compositions |
| WO2013110313A1 (en) * | 2012-01-23 | 2013-08-01 | H. Lundbeck A/S | Selective allosteric modulators of the serotonin transporter |
| AU2015237253B2 (en) | 2014-03-28 | 2019-11-14 | Azevan Pharmaceuticals, Inc. | Compositions and methods for treating neurodegenerative diseases |
| MA43817B1 (fr) | 2016-03-10 | 2022-04-29 | Janssen Pharmaceutica Nv | Méthodes de traitement de la dépression à l'aide d'antagonistes de récepteurs de l'orexine-2 |
| TW201919625A (zh) | 2017-09-15 | 2019-06-01 | 美商愛治凡製藥公司 | 用於治療腦損傷之組合物及方法 |
| KR20220049526A (ko) | 2019-07-19 | 2022-04-21 | 바이오엑셀 테라퓨틱스 인코포레이티드 | 비-진정성 덱스메데토미딘 치료 양생법 |
| US11806334B1 (en) | 2023-01-12 | 2023-11-07 | Bioxcel Therapeutics, Inc. | Non-sedating dexmedetomidine treatment regimens |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (cs) * | 1965-03-18 |
-
1976
- 1976-01-14 GB GB1486/76A patent/GB1526331A/en not_active Expired
- 1976-12-16 DE DE2657013A patent/DE2657013C2/de not_active Expired
- 1976-12-17 SE SE7614201A patent/SE429551B/xx not_active IP Right Cessation
- 1976-12-21 AT AT947276A patent/AT359488B/de active Protection Beyond IP Right Term
-
1977
- 1977-01-04 IE IE5/77A patent/IE44055B1/en not_active IP Right Cessation
- 1977-01-05 ZA ZA770057A patent/ZA7757B/xx unknown
- 1977-01-05 AU AU21073/77A patent/AU509445B2/en not_active Expired
- 1977-01-06 NZ NZ183001A patent/NZ183001A/en unknown
- 1977-01-07 US US05/757,619 patent/US4136193A/en not_active Expired - Lifetime
- 1977-01-11 FI FI770073A patent/FI63754C/fi not_active IP Right Cessation
- 1977-01-12 NL NL7700244A patent/NL192451C/nl not_active IP Right Cessation
- 1977-01-12 ES ES454980A patent/ES454980A1/es not_active Expired
- 1977-01-13 JP JP199777A patent/JPS52105162A/ja active Granted
- 1977-01-13 CH CH42377A patent/CH626886A5/de not_active IP Right Cessation
- 1977-01-13 CA CA000269610A patent/CA1094087A/en not_active Expired
- 1977-01-13 NO NO770109A patent/NO147243C/no unknown
- 1977-01-14 DK DK13177A patent/DK143275C/da active
- 1977-01-14 BE BE174098A patent/BE850401A/xx not_active IP Right Cessation
- 1977-01-14 FR FR7701079A patent/FR2338271A1/fr active Granted
-
1981
- 1981-06-01 CH CH357581A patent/CH632259A5/de not_active IP Right Cessation
- 1981-06-01 CH CH357481A patent/CH632258A5/de not_active IP Right Cessation
-
1996
- 1996-01-05 NO NO1996001C patent/NO1996001I1/no unknown
-
1997
- 1997-08-04 NL NL970031C patent/NL970031I2/nl unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L20 Extension date: 20020111 |
|
| MA | Patent expired |
Owner name: H. LUNDBECK A/S |