SK20242000A3 - Paroxetínová soľ, spôsob jej prípravy a jej použitie - Google Patents

Paroxetínová soľ, spôsob jej prípravy a jej použitie Download PDF

Info

Publication number: SK20242000A3
Authority: SK; Slovakia
Prior art keywords: acid; benzoic; carboxylic; methyl; chloro
Prior art date: 1998-07-02

Application number

SK2024-2000A

Other languages

English (en)

Slovak (sk)

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

2001-07-10

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

2001-07-10 Publication of SK20242000A3 publication Critical patent/SK20242000A3/sk

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 48
150000003839 salts Chemical class 0.000 title 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 title claims description 21
229960002296 paroxetine Drugs 0.000 title claims description 20
238000000034 method Methods 0.000 claims abstract description 10
-1 amine salt Chemical class 0.000 claims description 745
239000002253 acid Substances 0.000 claims description 677
239000012458 free base Substances 0.000 claims description 15
239000000243 solution Substances 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000003921 oil Substances 0.000 claims description 5
239000012266 salt solution Substances 0.000 claims description 5
238000001704 evaporation Methods 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
238000002425 crystallisation Methods 0.000 claims description 3
230000008025 crystallization Effects 0.000 claims description 3
238000004108 freeze drying Methods 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
238000001694 spray drying Methods 0.000 claims description 3
208000007848 Alcoholism Diseases 0.000 claims description 2
208000019901 Anxiety disease Diseases 0.000 claims description 2
208000032841 Bulimia Diseases 0.000 claims description 2
206010006550 Bulimia nervosa Diseases 0.000 claims description 2
208000000094 Chronic Pain Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
208000019695 Migraine disease Diseases 0.000 claims description 2
208000008589 Obesity Diseases 0.000 claims description 2
208000002193 Pain Diseases 0.000 claims description 2
206010041250 Social phobia Diseases 0.000 claims description 2
201000007930 alcohol dependence Diseases 0.000 claims description 2
208000022531 anorexia Diseases 0.000 claims description 2
230000036506 anxiety Effects 0.000 claims description 2
206010061428 decreased appetite Diseases 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000011521 glass Substances 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
235000020824 obesity Nutrition 0.000 claims description 2
208000019906 panic disease Diseases 0.000 claims description 2
238000001291 vacuum drying Methods 0.000 claims description 2
230000032683 aging Effects 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
210000002784 stomach Anatomy 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 6
238000002560 therapeutic procedure Methods 0.000 abstract description 2
150000003053 piperidines Chemical class 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 97
239000005711 Benzoic acid Substances 0.000 description 67
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 57
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 49
239000004220 glutamic acid Substances 0.000 description 40
235000010233 benzoic acid Nutrition 0.000 description 29
235000019260 propionic acid Nutrition 0.000 description 15
PNUDNLMYGFJAPI-UHFFFAOYSA-N CC1(OC(C(O1)CC(=O)O)=O)C.C1(CCCC1)OC=1C=C(C(=O)O)C=CC1OC.C(C1=CC=CC=C1)(=O)NCCCC(C(=O)O)Br Chemical compound CC1(OC(C(O1)CC(=O)O)=O)C.C1(CCCC1)OC=1C=C(C(=O)O)C=CC1OC.C(C1=CC=CC=C1)(=O)NCCCC(C(=O)O)Br PNUDNLMYGFJAPI-UHFFFAOYSA-N 0.000 description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
FVTJKPXHBWMDCU-ASBJOMSESA-N CO[C@@](C(=O)O)(C(F)(F)F)C1=CC=CC=C1.C1(=CC=CC=C1)CCCCCCCCCCCCCCCCCC(=O)O.COC1=CC=C(C=C1)P(O)(=O)C1=CC=C(C=C1)OC Chemical compound CO[C@@](C(=O)O)(C(F)(F)F)C1=CC=CC=C1.C1(=CC=CC=C1)CCCCCCCCCCCCCCCCCC(=O)O.COC1=CC=C(C=C1)P(O)(=O)C1=CC=C(C=C1)OC FVTJKPXHBWMDCU-ASBJOMSESA-N 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 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
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 8
WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
239000002904 solvent Substances 0.000 description 7
NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
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 6
229960004889 salicylic acid Drugs 0.000 description 6
239000001384 succinic acid Substances 0.000 description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
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 5
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
239000011976 maleic acid Substances 0.000 description 5
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
239000007787 solid Substances 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 4
RNSKXEKDTXOLOC-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[(3-chloro-2-methylphenyl)carbamoyl]benzoic acid Chemical compound CC1=C(Cl)C=CC=C1NC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O RNSKXEKDTXOLOC-UHFFFAOYSA-N 0.000 description 4
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 4
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 4
229960004050 aminobenzoic acid Drugs 0.000 description 4
229940092714 benzenesulfonic acid Drugs 0.000 description 4
229930016911 cinnamic acid Natural products 0.000 description 4
235000013985 cinnamic acid Nutrition 0.000 description 4
235000019700 dicalcium phosphate Nutrition 0.000 description 4
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 4
VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
229960003424 phenylacetic acid Drugs 0.000 description 4
239000003279 phenylacetic acid Substances 0.000 description 4
229940079832 sodium starch glycolate Drugs 0.000 description 4
239000008109 sodium starch glycolate Substances 0.000 description 4
229920003109 sodium starch glycolate Polymers 0.000 description 4
239000012453 solvate Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
229960001367 tartaric acid Drugs 0.000 description 4
239000011975 tartaric acid Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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238000002360 preparation method Methods 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
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
229940005605 valeric acid Drugs 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
HVGRZDASOHMCSK-HZJYTTRNSA-N (13Z,16Z)-docosadienoic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCCCCC(O)=O HVGRZDASOHMCSK-HZJYTTRNSA-N 0.000 description 2
QQVDJLLNRSOCEL-UHFFFAOYSA-N (2-aminoethyl)phosphonic acid Chemical compound [NH3+]CCP(O)([O-])=O QQVDJLLNRSOCEL-UHFFFAOYSA-N 0.000 description 2
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PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 2
NJQRKFOZZUIMGW-UHFFFAOYSA-N 1,3,5-trichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=C(Cl)C=C1Cl NJQRKFOZZUIMGW-UHFFFAOYSA-N 0.000 description 2
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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FUCWJKJZOHOLEO-UHFFFAOYSA-N 10-formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxo-1-benzo[b][1,4]benzodioxepincarboxylic acid Chemical compound O=C1OC2=C(C)C(OC)=CC(C(O)=O)=C2OC2=C(C=O)C(O)=CC(C)=C21 FUCWJKJZOHOLEO-UHFFFAOYSA-N 0.000 description 2
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
MCDKTZLMNAVTIJ-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)-1,3-dihydroindene-2-carboxylic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NC1(C(=O)O)CC2=CC=CC=C2C1 MCDKTZLMNAVTIJ-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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LWUAMROXVQLJKA-UHFFFAOYSA-N 2-amino-3-chlorobenzoic acid Chemical compound NC1=C(Cl)C=CC=C1C(O)=O LWUAMROXVQLJKA-UHFFFAOYSA-N 0.000 description 2
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OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
IPOVLZSJBYKHHU-UHFFFAOYSA-N piperidin-3-ylmethanamine Chemical compound NCC1CCCNC1 IPOVLZSJBYKHHU-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
XYWJNTOURDMTPI-UHFFFAOYSA-N procodazole Chemical compound C1=CC=C2NC(CCC(=O)O)=NC2=C1 XYWJNTOURDMTPI-UHFFFAOYSA-N 0.000 description 1
ATLPLEZDTSBZQG-UHFFFAOYSA-N propan-2-ylphosphonic acid Chemical compound CC(C)P(O)(O)=O ATLPLEZDTSBZQG-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DLOBKMWCBFOUHP-UHFFFAOYSA-N pyrene-1-sulfonic acid Chemical compound C1=C2C(S(=O)(=O)O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 DLOBKMWCBFOUHP-UHFFFAOYSA-N 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 1
235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 1
239000011589 pyridoxal 5'-phosphate Substances 0.000 description 1
229960001327 pyridoxal phosphate Drugs 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
229960003656 ricinoleic acid Drugs 0.000 description 1
FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
WUILNKCFCLNXOK-CFBAGHHKSA-N salirasib Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CSC1=CC=CC=C1C(O)=O WUILNKCFCLNXOK-CFBAGHHKSA-N 0.000 description 1
229960000953 salsalate Drugs 0.000 description 1
ZNSIZMQNQCNRBW-UHFFFAOYSA-N sevelamer Chemical compound NCC=C.ClCC1CO1 ZNSIZMQNQCNRBW-UHFFFAOYSA-N 0.000 description 1
JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
201000009032 substance abuse Diseases 0.000 description 1
231100000736 substance abuse Toxicity 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
WRKFFLDTHRUFCE-UHFFFAOYSA-N tert-butyl 3-[[(4-fluorophenyl)methylamino]methyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1CNCC1=CC=C(F)C=C1 WRKFFLDTHRUFCE-UHFFFAOYSA-N 0.000 description 1
IYNZAVDBHAQODX-UHFFFAOYSA-N tert-butyl 4-(4-bromopyrazol-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(Br)=C1 IYNZAVDBHAQODX-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
GVZXSZWCZGKLRS-UHFFFAOYSA-N thieno[3,2-b]thiophene-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(=O)O)S2 GVZXSZWCZGKLRS-UHFFFAOYSA-N 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
MHMUCYJKZUZMNJ-OWOJBTEDSA-N trans-3-chloroacrylic acid Chemical compound OC(=O)\C=C\Cl MHMUCYJKZUZMNJ-OWOJBTEDSA-N 0.000 description 1
YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 description 1
QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
208000002271 trichotillomania Diseases 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
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
229960000604 valproic acid Drugs 0.000 description 1
WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
RQIDQEBURXNDKG-MDZDMXLPSA-N ximenic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCCCCCC(O)=O RQIDQEBURXNDKG-MDZDMXLPSA-N 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

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)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Psychiatry (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)

SK2024-2000A 1998-07-02 1999-06-30 Paroxetínová soľ, spôsob jej prípravy a jej použitie SK20242000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9814316.7A GB9814316D0 (en)	1998-07-02	1998-07-02	Novel compounds
PCT/EP1999/004543 WO2000001692A1 (en)	1998-07-02	1999-06-30	Salts of paroxetine

Publications (1)

Publication Number	Publication Date
SK20242000A3 true SK20242000A3 (sk)	2001-07-10

Family

ID=10834803

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK2024-2000A SK20242000A3 (sk)	1998-07-02	1999-06-30	Paroxetínová soľ, spôsob jej prípravy a jej použitie

Country Status (21)

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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1622630T3 (da)	2003-05-07	2012-12-17	Osteologix As	P009368epdk1
ATE342722T1 (de)	2003-05-07	2006-11-15	Osteologix As	Behandlung von knorpel/knochen-erkrankungen mit wasserlöslichen strontiumsalzen
PL1732575T3 (pl)	2004-02-26	2011-05-31	Osteologix As	Związki zawierające stron do stosowania w zapobieganiu lub leczeniu stanów nekrotycznych kości
CN101010087B (zh)	2004-05-06	2012-06-27	奥斯泰奥洛吉斯公司	用于制备金属有机盐的高收率和快速的合成方法
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
ES2058061T3 (es) *	1985-10-25	1994-11-01	Beecham Group Plc	Derivado de piperidina, su preparacion y su uso como medicamento.
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
KR100543614B1 (ko) *	1997-06-10	2006-01-20	신톤 비.브이.	4-페닐피페리딘 화합물
KR20010040711A (ko) *	1998-02-06	2001-05-15	피터 기딩스	파록세틴의 염

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 CA CA002336470A patent/CA2336470A1/en not_active Abandoned
- 1999-06-30 CZ CZ20004923A patent/CZ20004923A3/cs unknown
- 1999-06-30 JP JP2000558095A patent/JP2002519421A/ja active Pending
- 1999-06-30 TR TR2001/00055T patent/TR200100055T2/xx unknown
- 1999-06-30 WO PCT/EP1999/004543 patent/WO2000001692A1/en not_active Ceased
- 1999-06-30 EP EP99932772A patent/EP1091958A1/en not_active Withdrawn
- 1999-06-30 AP APAP/P/2000/002017A patent/AP2000002017A0/en unknown
- 1999-06-30 HU HU0103712A patent/HUP0103712A3/hu unknown
- 1999-06-30 EA EA200100098A patent/EA200100098A1/ru unknown
- 1999-06-30 SK SK2024-2000A patent/SK20242000A3/sk unknown
- 1999-06-30 BR BR9911679-0A patent/BR9911679A/pt not_active Application Discontinuation
- 1999-06-30 KR KR1020007015100A patent/KR20010053337A/ko not_active Withdrawn
- 1999-06-30 AU AU49039/99A patent/AU4903999A/en not_active Abandoned
- 1999-06-30 IL IL14038599A patent/IL140385A0/xx unknown
- 1999-06-30 PL PL99345365A patent/PL345365A1/xx not_active Application Discontinuation
- 1999-06-30 CN CN99810197A patent/CN1314906A/zh active Pending
- 1999-06-30 ID IDW20010252A patent/ID27766A/id 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
AU4903999A (en)	2000-01-24
EA200100098A1 (ru)	2001-08-27
HUP0103712A3 (en)	2002-09-30
BG105204A (en)	2001-11-30
HUP0103712A2 (hu)	2002-05-29
CA2336470A1 (en)	2000-01-13
BR9911679A (pt)	2002-01-29
WO2000001692A1 (en)	2000-01-13
AP2000002017A0 (en)	2000-12-31
ZA200100020B (en)	2002-03-25
AU2002100370A4 (en)	2002-06-06
ZA992899B (en)	2000-03-29
ID27766A (id)	2001-04-26
TR200100055T2 (tr)	2001-07-23
NO20006547L (no)	2001-02-12
CZ20004923A3 (cs)	2001-08-15
NO20006547D0 (no)	2000-12-21
KR20010053337A (ko)	2001-06-25
GB9814316D0 (en)	1998-09-02
EP1091958A1 (en)	2001-04-18
CN1314906A (zh)	2001-09-26
PL345365A1 (en)	2001-12-17
IL140385A0 (en)	2002-02-10
JP2002519421A (ja)	2002-07-02

Publication	Publication Date	Title
SK20242000A3 (sk)	2001-07-10	Paroxetínová soľ, spôsob jej prípravy a jej použitie
DE69527798T2 (de)	2003-01-02	Substituierte 4-biarylbutyr-oder 5-biarylpentasäuren und derivate als matrix metalloprotease inhibitoren
RU2529484C2 (ru)	2014-09-27	Ациламино-замещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств
US4499299A (en)	1985-02-12	Pharmaceutically active phenylcarboxylic acid derivatives
DE69514813T2 (de)	2000-08-17	Bicyclische diarylheterocyclen als cyclooxygenase-2-inhibitoren
CA2401778A1 (en)	2001-09-07	Benzamides and related inhibitors of factor xa
KR100938950B1 (ko)	2010-01-26	치환 페닐 알칸산 유도체 및 그 용도
HU183085B (en)	1984-04-28	Process for preparing new phenoxy-alkyl-carboxylic acid derivatives and pharmaceutical compositions containing thereof
HK68887A (en)	1987-10-02	Sulphonamides, process for their preparation and medicines containing these compounds
IE43142B1 (en)	1980-12-31	Phenylacetic acid derivatives
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
SU803856A3 (ru)	1981-02-07	Производные -/арил(алкил, алке-Нил)АМиНО/-бЕНзОйНОй КиСлОТы илифАРМАцЕВТичЕСКи пРиЕМлЕМыЕ СОли,ОблАдАющиЕ СпОСОбНОСТью СНижАТьуРОВЕНь липидОВ B СыВОРОТКЕ КРОВи
DE69023960T2 (de)	1996-10-17	Phenylalkan(en)säuren.
GB1476214A (en)	1977-06-10	Dibenzoxepin derivatives process for the preparation thereof and pharmaceutical compositions containing them
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