CS404891A3 - Quinoline derivatives, process of their preparation and pharmaceutical compositions containing said compounds - Google Patents

Quinoline derivatives, process of their preparation and pharmaceutical compositions containing said compounds Download PDF

Info

Publication number: CS404891A3
Authority: CS; Czechoslovakia
Prior art keywords: formula; compounds; hydrogen; compound; quinolinone
Prior art date: 1988-10-11

Application number

CS914048A

Other languages

Czech (cs)

English (en)

Inventor

Philippe Manoury

Daniel Obitz

Michel Peynot

Jonathan Frost

Original Assignee

Synthelabo

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.)

1988-10-11

Filing date

1991-12-23

Publication date

1992-04-15

1991-12-23 Application filed by Synthelabo filed Critical Synthelabo

1992-04-15 Publication of CS404891A3 publication Critical patent/CS404891A3/cs

Links

150000001875 compounds Chemical class 0.000 title claims description 79
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 7
230000008569 process Effects 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
150000007513 acids Chemical class 0.000 claims abstract description 5
229910052731 fluorine Chemical group 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
-1 tetrahydronaphthalenyl Chemical group 0.000 claims description 11
150000002148 esters Chemical class 0.000 claims description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
MWIXENPCUPDSOS-QMMMGPOBSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanehydrazide Chemical compound NNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWIXENPCUPDSOS-QMMMGPOBSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
150000003248 quinolines Chemical class 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
239000011737 fluorine Chemical group 0.000 abstract description 2
125000005843 halogen group Chemical group 0.000 abstract description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 abstract 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 abstract 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000000203 mixture Substances 0.000 description 36
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 25
238000003756 stirring Methods 0.000 description 22
239000000243 solution Substances 0.000 description 18
239000000725 suspension Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000001816 cooling Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000872 buffer Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000010992 reflux Methods 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
239000012265 solid product Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
230000000694 effects Effects 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000000155 melt Substances 0.000 description 7
NNHOCNIVPRRFFB-UHFFFAOYSA-N 2-(2-oxo-3,4-dihydro-1h-quinolin-4-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)CC(=O)NC2=C1 NNHOCNIVPRRFFB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000027455 binding Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
238000003556 assay Methods 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
230000009870 specific binding Effects 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XUHPYOVEVMTWNH-UHFFFAOYSA-N 4-(2-hydroxyethyl)-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCO)C2=CC(C)=CC=C21 XUHPYOVEVMTWNH-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000013049 sediment Substances 0.000 description 4
230000002295 serotoninergic effect Effects 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
UXVHMJOEWPQFFT-UHFFFAOYSA-N 2-(2-oxo-1h-quinolin-4-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC(=O)NC2=C1 UXVHMJOEWPQFFT-UHFFFAOYSA-N 0.000 description 3
HAFFANOEWVBHRX-UHFFFAOYSA-N 4-(2-hydroxyethyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(CCO)CC(=O)NC2=C1 HAFFANOEWVBHRX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229940076279 serotonin Drugs 0.000 description 3
229950001675 spiperone Drugs 0.000 description 3
SOCSGMHMTZRARN-UHFFFAOYSA-N (2,6-dioxo-3h-pyran-3-yl) acetate Chemical compound CC(=O)OC1C=CC(=O)OC1=O SOCSGMHMTZRARN-UHFFFAOYSA-N 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NHQHUBOLAKEMOP-UHFFFAOYSA-N 1-(2-chloroethyl)-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CCCl)C(=O)CCC2=C1 NHQHUBOLAKEMOP-UHFFFAOYSA-N 0.000 description 2
CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
PLEPMKYNIWPRSI-UHFFFAOYSA-N 3-acetyloxy-5-anilino-5-oxopent-2-enoic acid Chemical compound CC(=O)OC(=CC(O)=O)CC(=O)NC1=CC=CC=C1 PLEPMKYNIWPRSI-UHFFFAOYSA-N 0.000 description 2
RKESVMFIRZZEKY-UHFFFAOYSA-N 4-(2-chloroethyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(CCCl)CC(=O)NC2=C1 RKESVMFIRZZEKY-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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230000008485 antagonism Effects 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
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238000004587 chromatography analysis Methods 0.000 description 2
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RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
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238000005984 hydrogenation reaction Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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KLDVSXHBYSMHNT-UHFFFAOYSA-N methyl 2-(2-oxo-1h-quinolin-4-yl)acetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC(=O)NC2=C1 KLDVSXHBYSMHNT-UHFFFAOYSA-N 0.000 description 2
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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IWUSEHGANVYEQR-UHFFFAOYSA-N (2,6-dioxo-3h-pyran-4-yl) acetate Chemical compound CC(=O)OC1=CC(=O)OC(=O)C1 IWUSEHGANVYEQR-UHFFFAOYSA-N 0.000 description 1
YEZCXUSENFZWJO-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CCO)C(=O)CCC2=C1 YEZCXUSENFZWJO-UHFFFAOYSA-N 0.000 description 1
XDYRIGIBUWJCMR-UHFFFAOYSA-N 1-(7-methoxynaphthalen-1-yl)piperazine Chemical compound C12=CC(OC)=CC=C2C=CC=C1N1CCNCC1 XDYRIGIBUWJCMR-UHFFFAOYSA-N 0.000 description 1
KSINUERPPVUVKN-UHFFFAOYSA-N 2-(5-fluoro-2-oxo-1h-quinolin-4-yl)acetic acid Chemical compound C1=CC(F)=C2C(CC(=O)O)=CC(=O)NC2=C1 KSINUERPPVUVKN-UHFFFAOYSA-N 0.000 description 1
GTBYPAOBFWQMRV-UHFFFAOYSA-N 2-(6-methyl-2-oxo-1h-quinolin-4-yl)acetic acid Chemical compound N1C(=O)C=C(CC(O)=O)C2=CC(C)=CC=C21 GTBYPAOBFWQMRV-UHFFFAOYSA-N 0.000 description 1
IUOAPZODPUAZAN-UHFFFAOYSA-N 2-(7-fluoro-2-oxo-1h-quinolin-4-yl)acetic acid Chemical compound FC1=CC=C2C(CC(=O)O)=CC(=O)NC2=C1 IUOAPZODPUAZAN-UHFFFAOYSA-N 0.000 description 1
TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
VRHZUJMLXLZSNZ-UHFFFAOYSA-N 4-(2-chloroethyl)-1h-quinolin-2-one Chemical compound C1=CC=C2C(CCCl)=CC(=O)NC2=C1 VRHZUJMLXLZSNZ-UHFFFAOYSA-N 0.000 description 1
TUYMVHRMMXWWQI-UHFFFAOYSA-N 4-(2-chloroethyl)-6-methyl-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCCl)C2=CC(C)=CC=C21 TUYMVHRMMXWWQI-UHFFFAOYSA-N 0.000 description 1
BLZJVRZXDASPTC-UHFFFAOYSA-N 4-(2-chloroethyl)-7-fluoro-1h-quinolin-2-one Chemical compound ClCCC1=CC(=O)NC2=CC(F)=CC=C21 BLZJVRZXDASPTC-UHFFFAOYSA-N 0.000 description 1
DQPHQQYRMCMEGI-UHFFFAOYSA-N 4-(2-hydroxyethyl)-1-methylquinolin-2-one Chemical compound C1=CC=C2C(CCO)=CC(=O)N(C)C2=C1 DQPHQQYRMCMEGI-UHFFFAOYSA-N 0.000 description 1
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
108091005479 5-HT2 receptors Proteins 0.000 description 1
108091005482 5-HT4 receptors Proteins 0.000 description 1
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical class C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
WFIKYLCAGCPOPE-UHFFFAOYSA-N 7-fluoro-4-(2-hydroxyethyl)-1h-quinolin-2-one Chemical compound FC1=CC=C2C(CCO)=CC(=O)NC2=C1 WFIKYLCAGCPOPE-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
241000252095 Congridae Species 0.000 description 1
235000014375 Curcuma Nutrition 0.000 description 1
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BTEITVCBGQBRIQ-WDBKTSHHSA-N N[C@@H](CC1=CC=C(C=C1)O)C(=O)NN.O=C1NC2=CC=CC=C2C(C1)CC(=O)O Chemical compound N[C@@H](CC1=CC=C(C=C1)O)C(=O)NN.O=C1NC2=CC=CC=C2C(C1)CC(=O)O BTEITVCBGQBRIQ-WDBKTSHHSA-N 0.000 description 1
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MASVCBBIUQRUKL-UHFFFAOYSA-N POPOP Chemical compound C=1N=C(C=2C=CC(=CC=2)C=2OC(=CN=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 MASVCBBIUQRUKL-UHFFFAOYSA-N 0.000 description 1
DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
241000906446 Theraps Species 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
230000000794 anti-serotonin Effects 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
244000309464 bull Species 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
230000008859 change Effects 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
230000010807 negative regulation of binding Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
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229960004441 tyrosine Drugs 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Quinoline Compounds (AREA)

CS914048A 1988-10-11 1991-12-23 Quinoline derivatives, process of their preparation and pharmaceutical compositions containing said compounds CS404891A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8813324A FR2637591B1 (fr)	1988-10-11	1988-10-11	Derives de quinoleinone, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
CS404891A3 true CS404891A3 (en)	1992-04-15

Family

ID=9370884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS914048A CS404891A3 (en)	1988-10-11	1991-12-23	Quinoline derivatives, process of their preparation and pharmaceutical compositions containing said compounds

Country Status (20)

Country	Link
US (1)	US4983607A (de)
EP (1)	EP0364327B1 (de)
JP (1)	JPH02157267A (de)
KR (1)	KR900006317A (de)
AT (1)	ATE71617T1 (de)
AU (1)	AU619349B2 (de)
CS (1)	CS404891A3 (de)
DE (1)	DE68900717D1 (de)
DK (1)	DK500189A (de)
ES (1)	ES2037980T3 (de)
FI (1)	FI91748C (de)
FR (1)	FR2637591B1 (de)
GR (1)	GR3003921T3 (de)
HU (1)	HU204813B (de)
IE (1)	IE61830B1 (de)
IL (1)	IL91930A (de)
NO (1)	NO173058C (de)
NZ (1)	NZ230959A (de)
PT (1)	PT91939B (de)
ZA (1)	ZA897672B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2635105B1 (fr) *	1988-08-03	1991-01-25	Synthelabo	Derives de piperazine et leur procede de preparation
US5457099A (en) *	1992-07-02	1995-10-10	Sawai Pharmaceutical Co., Ltd.	Carbostyril derivatives and antiallergic agent
DK148392D0 (da) *	1992-12-09	1992-12-09	Lundbeck & Co As H	Heterocykliske forbindelser
US5607946A (en) *	1993-03-05	1997-03-04	Merck Sharp & Dohme Ltd.	Quinolone derivatives as dopamine D4 ligands
CA2158457C (en) *	1993-03-16	2001-04-17	Bertrand Leo Chenard	Naphthalene derivatives
FR2737723B1 (fr) *	1995-08-09	1997-09-05	Synthelabo	Derives de 1-(2-(1h-inden-3-yl)ethyl)-4-(naphtalen-1-yl)- piperazine, leur preparation et leur application en therapeutique
FR2738823B1 (fr) *	1995-09-15	1997-10-31	Synthelabo	Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique
FR2761071B1 (fr) *	1997-03-20	1999-12-03	Synthelabo	Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique
FR2761067B1 (fr) *	1997-03-20	1999-04-23	Synthelabo	Derives de quinolein-2-(1h)-one, leur preparation et leur application en therapeutique
US6562837B1 (en) *	1998-10-21	2003-05-13	Korea Institute Of Science & Technology	Use of tetrahydroisoquinoline compounds for the treatment of septicemia
ES2332770T3 (es)	2000-11-07	2010-02-12	Novartis Ag	Derivados de indolilmaleimida como inhibidores de la proteina quinasa c.
US7053092B2 (en) *	2001-01-29	2006-05-30	Otsuka Pharmaceutical Co., Ltd.	5-HT1a receptor subtype agonist
US8703772B2 (en)	2001-09-25	2014-04-22	Otsuka Pharmaceutical Co., Ltd.	Low hygroscopic aripiprazole drug substance and processes for the preparation thereof
AR033485A1 (es) *	2001-09-25	2003-12-26	Otsuka Pharma Co Ltd	Sustancia medicinal de aripiprazol de baja higroscopicidad y proceso para la preparacion de la misma
TW200803855A (en) *	2006-02-24	2008-01-16	Kalypsys Inc	Quinolones useful as inducible nitric oxide synthase inhibitors
JP2011520956A (ja) *	2008-05-20	2011-07-21	アストラゼネカ・アクチエボラーグ	不安大うつ病性障害を処置する方法
MA41168A (fr) *	2014-12-17	2017-10-24	Acraf	Nouveaux composés antibactériens

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54128588A (en) *	1978-03-29	1979-10-05	Dainippon Pharmaceut Co Ltd	Antidepressive drugs consisting mainly of 2-(1-piperazinyl)- 4-phenylquinoline
JPS54130587A (en) *	1978-03-30	1979-10-09	Otsuka Pharmaceut Co Ltd	Carbostyryl derivative
PH17194A (en) *	1980-03-06	1984-06-19	Otsuka Pharma Co Ltd	Novel carbostyril derivatives,and pharmaceutical composition containing the same
US4284768A (en) *	1980-07-02	1981-08-18	American Home Products Corporation	1,2-Dihydro-4-amino-2-oxo-3-quinoline-carboxylic acid derivatives
GB8827189D0 (en) *	1988-11-21	1988-12-29	Fujisawa Pharmaceutical Co	2(1h)-quinolinone compounds processes for preparation thereof & pharmaceutical composition comprising same

1988
- 1988-10-11 FR FR8813324A patent/FR2637591B1/fr not_active Expired - Fee Related
1989
- 1989-10-02 DE DE8989402700T patent/DE68900717D1/de not_active Expired - Lifetime
- 1989-10-02 EP EP89402700A patent/EP0364327B1/de not_active Expired - Lifetime
- 1989-10-02 AT AT89402700T patent/ATE71617T1/de not_active IP Right Cessation
- 1989-10-02 ES ES198989402700T patent/ES2037980T3/es not_active Expired - Lifetime
- 1989-10-09 ZA ZA897672A patent/ZA897672B/xx unknown
- 1989-10-10 PT PT91939A patent/PT91939B/pt not_active IP Right Cessation
- 1989-10-10 FI FI894803A patent/FI91748C/fi not_active IP Right Cessation
- 1989-10-10 AU AU42750/89A patent/AU619349B2/en not_active Ceased
- 1989-10-10 IE IE326589A patent/IE61830B1/en not_active IP Right Cessation
- 1989-10-10 DK DK500189A patent/DK500189A/da not_active Application Discontinuation
- 1989-10-10 IL IL91930A patent/IL91930A/xx not_active IP Right Cessation
- 1989-10-10 HU HU895268A patent/HU204813B/hu not_active IP Right Cessation
- 1989-10-10 NZ NZ230959A patent/NZ230959A/en unknown
- 1989-10-10 KR KR1019890014520A patent/KR900006317A/ko not_active Withdrawn
- 1989-10-10 US US07/417,970 patent/US4983607A/en not_active Expired - Lifetime
- 1989-10-10 NO NO894036A patent/NO173058C/no not_active IP Right Cessation
- 1989-10-11 JP JP1266051A patent/JPH02157267A/ja active Pending
1991
- 1991-12-23 CS CS914048A patent/CS404891A3/cs unknown
1992
- 1992-02-27 GR GR920400344T patent/GR3003921T3/el unknown

Also Published As

Publication number	Publication date
PT91939B (pt)	1995-05-31
AU619349B2 (en)	1992-01-23
ES2037980T3 (es)	1993-07-01
PT91939A (pt)	1990-04-30
NO894036D0 (no)	1989-10-10
DE68900717D1 (de)	1992-02-27
HU204813B (en)	1992-02-28
IL91930A (en)	1993-08-18
NZ230959A (en)	1990-12-21
FI894803A0 (fi)	1989-10-10
DK500189A (da)	1990-04-12
NO173058C (no)	1993-10-20
NO173058B (no)	1993-07-12
EP0364327B1 (de)	1992-01-15
ATE71617T1 (de)	1992-02-15
ZA897672B (en)	1990-07-25
FR2637591A1 (fr)	1990-04-13
IE61830B1 (en)	1994-11-30
IE893265L (en)	1990-04-11
FI91748C (fi)	1994-08-10
FI894803L (fi)	1990-04-12
FR2637591B1 (fr)	1992-10-23
KR900006317A (ko)	1990-05-07
GR3003921T3 (de)	1993-03-16
HUT51612A (en)	1990-05-28
FI91748B (fi)	1994-04-29
NO894036L (no)	1990-04-17
DK500189D0 (da)	1989-10-10
US4983607A (en)	1991-01-08
IL91930A0 (en)	1990-06-10
HU895268D0 (en)	1990-01-28
JPH02157267A (ja)	1990-06-18
EP0364327A1 (de)	1990-04-18
AU4275089A (en)	1990-04-26

Publication	Publication Date	Title
CS404891A3 (en)	1992-04-15	Quinoline derivatives, process of their preparation and pharmaceutical compositions containing said compounds
RU2182150C2 (ru)	2002-05-10	Производные бензимидазола, антигистаминная фармацевтическая композиция и способ лечения аллергических заболеваний
US4668686A (en)	1987-05-26	Imidazoquinoline antithrombrogenic cardiotonic agents
US5753663A (en)	1998-05-19	Pyrimidine derivatives
US5010079A (en)	1991-04-23	Indolone derivatives, their preparation and their application in therapy
JP5518928B2 (ja)	2014-06-11	光学活性ピペリジン誘導体の酸付加塩及びその製法
PT99154A (pt)	1993-12-31	Processo para a preparacao de derivados de indole, uteis como agentes anti-alergicos e anti-inflamatorios
PT88206B (pt)	1995-05-04	Processo para a preparacao de derivados de 2-{(4-piperidinil)-metil}-1,2,3,4-tetrahidro-9h-pirido{3,4-b}indol e de composicoes farmaceuticas que os contem
JPS6289679A (ja)	1987-04-24	ピペリジン誘導体
JP3057095B2 (ja)	2000-06-26	イサチン誘導体、その製造方法及びその使用方法
CZ51694A3 (en)	1994-10-19	Benzoxazine derivatives, process of their preparation and pharmaceutical composition in which said derivatives are comprised
US4243666A (en)	1981-01-06	4-Amino-2-piperidino-quinazolines
HU201543B (en)	1990-11-28	Process for production of derivatives of 2-(/piperin-4-il/-methil/)-1,2,3,4-tetrahydro-izoquinoline and medical compositions containing them
US20090306144A1 (en)	2009-12-10	Pyridine derivatives of alkyl oxindoles as 5-ht7 receptor active agents
US5597819A (en)	1997-01-28	Phenothiazine cytokine inhibitors
CS248020B2 (en)	1987-01-15	Production method of the (+)-enantiomere or (+-)-racemical 4a,9b-trans-hexahydro-1h-pyridoindole derivatives
US6436987B1 (en)	2002-08-20	Crystalline forms of (3S-trans)-2-[3,4-dihydro-4-hydroxy-3-(phenylmethyl)-2H-1-benzopyran-7-yl]-4-(trifluoromethyl)-benzoic acid
US7910591B2 (en)	2011-03-22	Piperazine derivatives of alkyl oxindoles
EP1751106B1 (de)	2008-10-29	Piperazinderivate von alkyloxindolen
SK16798A3 (en)	1998-08-05	1-[2-(2,3-dihydro-1h-inden-1-yl)ethyl]-4-(naphthalen- -1-yl)piperazine derivatives, preparation thereof and therapeutical use thereof
HU215598B (hu)	1999-01-28	Eljárás optikailag aktív 1-fenil-pirrolidon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására