CZ20004923A3 - Soli paroxetinu - Google Patents

Soli paroxetinu Download PDF

Info

Publication number: CZ20004923A3
Authority: CZ; Czechia
Prior art keywords: acid; carboxylic; benzoic; chloro; methyl
Prior art date: 1998-07-02

Application number

CZ20004923A

Other languages

Czech (cs)

English (en)

Inventor

Victor Witold Jacewicz

Original Assignee

Smithkline Beecham Plc

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.)

1998-07-02

Filing date

1999-06-30

Publication date

2001-08-15

1999-06-30 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2001-08-15 Publication of CZ20004923A3 publication Critical patent/CZ20004923A3/cs

Links

AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical class C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 title claims description 42
238000000034 method Methods 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims description 492
-1 organic acid salt Chemical class 0.000 claims description 274
150000003839 salts Chemical class 0.000 claims description 34
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 20
229960002296 paroxetine Drugs 0.000 claims description 20
239000012458 free base Substances 0.000 claims description 15
150000007513 acids Chemical class 0.000 claims description 14
239000000243 solution Substances 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 8
239000012266 salt solution Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000011521 glass Substances 0.000 claims description 2
230000000069 prophylactic effect Effects 0.000 claims description 2
239000007921 spray Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 4
238000002560 therapeutic procedure Methods 0.000 abstract description 2
150000003053 piperidines Chemical class 0.000 abstract 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 140
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 112
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 81
239000005711 Benzoic acid Substances 0.000 description 71
235000010233 benzoic acid Nutrition 0.000 description 71
235000019260 propionic acid Nutrition 0.000 description 38
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 36
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 26
229960002989 glutamic acid Drugs 0.000 description 20
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 14
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
229960005261 aspartic acid Drugs 0.000 description 13
239000004220 glutamic acid Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 13
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 11
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 10
235000013985 cinnamic acid Nutrition 0.000 description 10
229930016911 cinnamic acid Natural products 0.000 description 10
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 10
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 9
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
208000035475 disorder Diseases 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
239000011976 maleic acid Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 6
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 5
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 5
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
238000009472 formulation Methods 0.000 description 5
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 5
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 5
229960004889 salicylic acid Drugs 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 4
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
229940124277 aminobutyric acid Drugs 0.000 description 4
UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 4
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 4
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
229960003692 gamma aminobutyric acid Drugs 0.000 description 4
HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 4
239000012453 solvate Substances 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 3
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 3
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 3
GPVDHNVGGIAOQT-UHFFFAOYSA-N 2,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 3
PJUXPMVQAZLJEX-UHFFFAOYSA-N 2-(carboxymethylamino)benzoic acid Chemical compound OC(=O)CNC1=CC=CC=C1C(O)=O PJUXPMVQAZLJEX-UHFFFAOYSA-N 0.000 description 3
YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 description 3
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 3
QURCVMIEKCOAJU-UHFFFAOYSA-N 3-Hydroxy 4-Methoxy Cinnamic acid Chemical compound COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 3
WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 3
XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 3
IFLKEBSJTZGCJG-UHFFFAOYSA-N 5-methyl-2-thiophenecarboxylic acid Natural products CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HOKKHZGPKSLGJE-UHFFFAOYSA-N N-methyl-D-aspartic acid Natural products CNC(C(O)=O)CC(O)=O HOKKHZGPKSLGJE-UHFFFAOYSA-N 0.000 description 3
MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 3
YPGCWEMNNLXISK-UHFFFAOYSA-N alpha-phenylpropionic acid Natural products OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Natural products CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
RTGHRDFWYQHVFW-UHFFFAOYSA-N beta-Ketoadipic acid Natural products OC(=O)CCC(=O)CC(O)=O RTGHRDFWYQHVFW-UHFFFAOYSA-N 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
229960002969 oleic acid Drugs 0.000 description 3
230000002265 prevention Effects 0.000 description 3
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 3
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 3
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 3
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PLQMEXSCSAIXGB-SAXRGWBVSA-N (+)-artemisinic acid Chemical compound C1=C(C)CC[C@H]2[C@H](C)CC[C@@H](C(=C)C(O)=O)[C@H]21 PLQMEXSCSAIXGB-SAXRGWBVSA-N 0.000 description 2
VACHUYIREGFMSP-UHFFFAOYSA-N (+)-threo-9,10-Dihydroxy-octadecansaeure Natural products CCCCCCCCC(O)C(O)CCCCCCCC(O)=O VACHUYIREGFMSP-UHFFFAOYSA-N 0.000 description 2
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BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 2
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CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 2
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AQTUACKQXJNHFQ-ZCFIWIBFSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-ZCFIWIBFSA-N 0.000 description 2
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AQTUACKQXJNHFQ-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-LURJTMIESA-N 0.000 description 2
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ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
FNZBSNUICNVAAM-UHFFFAOYSA-N trimethyl-[methyl-[methyl-(methyl-phenyl-trimethylsilyloxysilyl)oxy-phenylsilyl]oxy-phenylsilyl]oxysilane Chemical compound C=1C=CC=CC=1[Si](C)(O[Si](C)(C)C)O[Si](C)(C=1C=CC=CC=1)O[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1 FNZBSNUICNVAAM-UHFFFAOYSA-N 0.000 description 1
FJDWNXHRKLLNHK-UHFFFAOYSA-N triphenylsilylformic acid Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(=O)O)C1=CC=CC=C1 FJDWNXHRKLLNHK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
BEOUGZFCUMNGOU-UHFFFAOYSA-N tuberculostearic acid Chemical compound CCCCCCCCC(C)CCCCCCCCC(O)=O BEOUGZFCUMNGOU-UHFFFAOYSA-N 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 1
LOIYMIARKYCTBW-UHFFFAOYSA-N urocanic acid Chemical compound OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
FEBNTWHYQKGEIQ-SUKRRCERSA-N valerenic acid Chemical compound C[C@@H]1CC[C@@H](\C=C(/C)C(O)=O)C2=C(C)CC[C@H]12 FEBNTWHYQKGEIQ-SUKRRCERSA-N 0.000 description 1
FUHPCDQQVWLRRY-UHFFFAOYSA-N valerenic acid Natural products CC1CCC(C=C(/C)C(=O)O)C2C1CC=C2C FUHPCDQQVWLRRY-UHFFFAOYSA-N 0.000 description 1
WJHZBTMHUNVIKC-UHFFFAOYSA-N valerylsalicylic acid Chemical compound CCCCC(=O)OC1=CC=CC=C1C(O)=O WJHZBTMHUNVIKC-UHFFFAOYSA-N 0.000 description 1
229960000604 valproic acid Drugs 0.000 description 1
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
FBZONXHGGPHHIY-UHFFFAOYSA-N xanthurenic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC(O)=C21 FBZONXHGGPHHIY-UHFFFAOYSA-N 0.000 description 1
CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 description 1
BIDDLDNGQCUOJQ-SDNWHVSQSA-N α-phenylcinnamic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C\C1=CC=CC=C1 BIDDLDNGQCUOJQ-SDNWHVSQSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/22—Anxiolytics
- 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

Landscapes

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

CZ20004923A 1998-07-02 1999-06-30 Soli paroxetinu CZ20004923A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9814316.7A GB9814316D0 (en)	1998-07-02	1998-07-02	Novel compounds

Publications (1)

Publication Number	Publication Date
CZ20004923A3 true CZ20004923A3 (cs)	2001-08-15

Family

ID=10834803

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20004923A CZ20004923A3 (cs)	1998-07-02	1999-06-30	Soli paroxetinu

Country Status (21)

Country	Link
EP (1)	EP1091958A1 (no)
JP (1)	JP2002519421A (no)
KR (1)	KR20010053337A (no)
CN (1)	CN1314906A (no)
AP (1)	AP2000002017A0 (no)
AU (2)	AU4903999A (no)
BG (1)	BG105204A (no)
BR (1)	BR9911679A (no)
CA (1)	CA2336470A1 (no)
CZ (1)	CZ20004923A3 (no)
EA (1)	EA200100098A1 (no)
GB (1)	GB9814316D0 (no)
HU (1)	HUP0103712A3 (no)
ID (1)	ID27766A (no)
IL (1)	IL140385A0 (no)
NO (1)	NO20006547L (no)
PL (1)	PL345365A1 (no)
SK (1)	SK20242000A3 (no)
TR (1)	TR200100055T2 (no)
WO (1)	WO2000001692A1 (no)
ZA (2)	ZA992899B (no)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1622630B1 (en)	2003-05-07	2012-08-29	Osteologix A/S	Strontium combinations for the prophylaxis/treatment of cartilage and/or bone conditions
ES2275218T3 (es)	2003-05-07	2007-06-01	Osteologix A/S	Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos.
US20080167513A1 (en)	2004-02-26	2008-07-10	Osteologlx A/S	Strontium-Containing Compounds for Use in the Prevention or Treatment of Necrotic Bone Conditions
US7589235B2 (en)	2004-05-06	2009-09-15	Osteologix, A/S	High yield and rapid synthesis methods for producing metallo-organic salts
KR100672184B1 (ko) *	2004-09-21	2007-01-19	주식회사종근당	파록세틴의 콜린산 또는 콜린산 유도체 염
ES2745411T3 (es)	2006-07-27	2020-03-02	Wang Nai Fang	Compuestos y composiciones de arilsulfanilo para administración de agentes activos
CN109212055B (zh) *	2018-08-19	2021-05-07	丁立平	一种测定饮用水中四种痕量单卤代苯乙酸的气相色谱-质谱联用法
CN109342633B (zh) *	2018-11-27	2020-10-02	北京市化工职业病防治院	尿液中苯、甲苯和二甲苯代谢物的检测方法
CN111337460B (zh) *	2018-12-18	2021-09-17	中国科学院大连化学物理研究所	一种高稳定性Halo-tag探针及其合成和生物应用
CN116283778B (zh) *	2023-02-23	2025-08-29	江苏理工学院	一种吡唑羧酸类化合物及其制备方法和应用
US20250091996A1 (en)	2023-09-15	2025-03-20	King Faisal University	2-(1h-imidazole-1-carbonyl)benzoic acid as an anticancer compound

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8430581D0 (en) *	1984-12-04	1985-01-09	Ferrosan As	Treatment
EP0223403B1 (en) *	1985-10-25	1993-08-04	Beecham Group Plc	Piperidine derivative, its preparation, and its use as medicament
CA2206592A1 (en) *	1996-05-30	1997-11-30	Shu-Zhong Wang	Method of producing amorphous paroxetine hydrochloride
HU221921B1 (hu) *	1996-07-08	2003-02-28	Richter Gedeon Vegyészeti Gyár Rt.	N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására
SK283394B6 (sk) *	1997-06-10	2003-07-01	Synthon B. V.	Zlúčeniny 4-fenylpiperidínu a jej farmaceuticky prijateľné soli, spôsob ich prípravy, liečivo s ich obsahom a ich použitie
SK11812000A3 (sk) *	1998-02-06	2001-08-06	Smithkline Beecham Plc	Soli paroxetínu, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie

1998
- 1998-07-02 GB GBGB9814316.7A patent/GB9814316D0/en not_active Ceased
1999
- 1999-04-23 ZA ZA9902899A patent/ZA992899B/xx unknown
- 1999-06-30 BR BR9911679-0A patent/BR9911679A/pt not_active Application Discontinuation
- 1999-06-30 SK SK2024-2000A patent/SK20242000A3/sk unknown
- 1999-06-30 CA CA002336470A patent/CA2336470A1/en not_active Abandoned
- 1999-06-30 PL PL99345365A patent/PL345365A1/xx not_active Application Discontinuation
- 1999-06-30 WO PCT/EP1999/004543 patent/WO2000001692A1/en not_active Ceased
- 1999-06-30 AU AU49039/99A patent/AU4903999A/en not_active Abandoned
- 1999-06-30 JP JP2000558095A patent/JP2002519421A/ja active Pending
- 1999-06-30 CN CN99810197A patent/CN1314906A/zh active Pending
- 1999-06-30 AP APAP/P/2000/002017A patent/AP2000002017A0/en unknown
- 1999-06-30 EP EP99932772A patent/EP1091958A1/en not_active Withdrawn
- 1999-06-30 EA EA200100098A patent/EA200100098A1/ru unknown
- 1999-06-30 CZ CZ20004923A patent/CZ20004923A3/cs unknown
- 1999-06-30 TR TR2001/00055T patent/TR200100055T2/xx unknown
- 1999-06-30 KR KR1020007015100A patent/KR20010053337A/ko not_active Withdrawn
- 1999-06-30 HU HU0103712A patent/HUP0103712A3/hu unknown
- 1999-06-30 ID IDW20010252A patent/ID27766A/id unknown
- 1999-06-30 IL IL14038599A patent/IL140385A0/xx unknown
2000
- 2000-12-21 NO NO20006547A patent/NO20006547L/no not_active Application Discontinuation
2001
- 2001-01-02 ZA ZA200100020A patent/ZA200100020B/en unknown
- 2001-01-31 BG BG105204A patent/BG105204A/xx unknown
- 2001-07-11 AU AU2002100370A patent/AU2002100370A4/en not_active Expired

Also Published As

Publication number	Publication date
ZA200100020B (en)	2002-03-25
BG105204A (en)	2001-11-30
NO20006547D0 (no)	2000-12-21
KR20010053337A (ko)	2001-06-25
ZA992899B (en)	2000-03-29
TR200100055T2 (tr)	2001-07-23
BR9911679A (pt)	2002-01-29
HUP0103712A2 (hu)	2002-05-29
HUP0103712A3 (en)	2002-09-30
AP2000002017A0 (en)	2000-12-31
AU4903999A (en)	2000-01-24
GB9814316D0 (en)	1998-09-02
IL140385A0 (en)	2002-02-10
NO20006547L (no)	2001-02-12
EA200100098A1 (ru)	2001-08-27
PL345365A1 (en)	2001-12-17
JP2002519421A (ja)	2002-07-02
CN1314906A (zh)	2001-09-26
AU2002100370A4 (en)	2002-06-06
SK20242000A3 (sk)	2001-07-10
ID27766A (id)	2001-04-26
WO2000001692A1 (en)	2000-01-13
EP1091958A1 (en)	2001-04-18
CA2336470A1 (en)	2000-01-13

Publication	Publication Date	Title
CZ20004923A3 (cs)	2001-08-15	Soli paroxetinu
US8071616B2 (en)	2011-12-06	Pyridine, quinoline, and isoquinoline N-oxides as kinase inhibitors
SU1097194A3 (ru)	1984-06-07	Способ получени производных феноксиалкилкарбоновой кислоты, а также их натриевых солей, сложных эфиров и амидов
DE69527798T2 (de)	2003-01-02	Substituierte 4-biarylbutyr-oder 5-biarylpentasäuren und derivate als matrix metalloprotease inhibitoren
JP4846978B2 (ja)	2011-12-28	タンパク質チロシンホスファターゼのオキシンドールヒドラジンモジュレータ
SU1443800A3 (ru)	1988-12-07	Способ получени производных тиазолидин-4(S)-карбоновой кислоты или ее солей с щелочными или щелочноземельными металлами,или ее сложных эфиров
WO2002022592A3 (en)	2002-06-27	Substituted urea neuropeptide y y5 receptor antagonists
JP2010504286A (ja)	2010-02-12	スフィンゴシン−１−リン酸（ｓ１ｐ）受容体アゴニスト及び／又はアンタゴニスト生物活性を有するヘテロ芳香族化合物
JP2010143937A (ja)	2010-07-01	抗凝血薬として用いるクマリン誘導体
WO2004065365A1 (ja)	2004-08-05	８−アザプロスタグランジン誘導体およびその医薬用途
JP2006504767A (ja)	2006-02-09	フェニル化合物
KR20040017812A (ko)	2004-02-27	심장병 환자 및 대사 장애를 위한 갑상선 호르몬 수용체길항근ⅱ
NO156650C (no)	1987-10-28	Fremgangsmaate for fremstilling av optisk aktiv 2-(6-methoxy-2-nafthyl)-propionsyre og salter, estere, ortho-estere og amider derav.
CS212758B2 (en)	1982-03-26	Method of preparing p-aminobenzoic acid derivatives and salts thereof
JPH02503316A (ja)	1990-10-11	化合物
EP1258473A1 (en)	2002-11-20	Benzoic acid derivatives, process for producing the same and drugs containing the same as the active ingredient
MXPA01000133A (en)	2001-09-07	Salts of paroxetine
CN1083825C (zh)	2002-05-01	生产2－(取代的苯甲酰基)－1,3－环己烷二酮的方法
HU215432B (hu)	1999-04-28	Eljárás aldóz-reduktáz-gátló aktivitású tetrazol-ecetsav-származékok és az ezeket tartalmazó gyógyszerkészítmények előállítására
JPH0278675A (ja)	1990-03-19	ベンゾフラニル酢酸誘導体、その製法、粘液調節剤および抗ヒスタミン剤
DE69108553T2 (de)	1995-08-03	Inhibitoren fur angiotensin umwandelnde enzyme.
WO2002004439A3 (en)	2002-09-26	Thiophene retinoids
RU96119966A (ru)	1998-12-27	Производное хинола для лечения недержания мочи
JPH08208672A (ja)	1996-08-13	ホスホノスルホネート塩スクアレンシンセターゼ抑制剤
JP2774836B2 (ja)	1998-07-09	チオフェン誘導体，及び該化合物を含有する医薬組成物