IL123600A - History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them - Google Patents

History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them

Info

Publication number: IL123600A
Authority: IL; Israel
Prior art keywords: group; equal; formula; mmol; compounds
Prior art date: 1995-09-15

Application number

IL12360096A

Other languages

English (en)

Hebrew (he)

Other versions

IL123600A0 (en

Original Assignee

Sanofi 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.)

1995-09-15

Filing date

1996-09-12

Publication date

2001-05-20

1995-09-15 Priority claimed from FR9510815A external-priority patent/FR2738822B1/fr

1995-09-21 Priority claimed from FR9511083A external-priority patent/FR2739100B1/fr

1996-09-12 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1998-10-30 Publication of IL123600A0 publication Critical patent/IL123600A0/xx

2001-05-20 Publication of IL123600A publication Critical patent/IL123600A/en

Links

238000002360 preparation method Methods 0.000 title description 5
150000007660 quinolones Chemical class 0.000 title description 2
238000002560 therapeutic procedure Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 93
-1 4-(thieno [3, 2-c] pyridin-4-yl) -1- piperazinyl group Chemical group 0.000 claims abstract description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000003277 amino group Chemical group 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
150000007513 acids Chemical class 0.000 claims abstract description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 10
RVGRTFBJOXMFAX-UHFFFAOYSA-N 4-piperazin-1-ylthieno[3,2-c]pyridine Chemical compound C1CNCCN1C1=NC=CC2=C1C=CS2 RVGRTFBJOXMFAX-UHFFFAOYSA-N 0.000 claims description 9
ABERUOJGWHYBJL-UHFFFAOYSA-N (4-fluorophenyl)-piperidin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCNCC1 ABERUOJGWHYBJL-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
239000000952 serotonin receptor agonist Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
239000000203 mixture Substances 0.000 description 64
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
230000008018 melting Effects 0.000 description 29
238000002844 melting Methods 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
239000000047 product Substances 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000012429 reaction media Substances 0.000 description 23
239000000243 solution Substances 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
238000010992 reflux Methods 0.000 description 15
239000000725 suspension Substances 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
238000003756 stirring Methods 0.000 description 14
238000001816 cooling Methods 0.000 description 13
239000000377 silicon dioxide Substances 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 8
238000000034 method Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 6
229960003708 sumatriptan Drugs 0.000 description 6
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
239000000872 buffer Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
229940076279 serotonin Drugs 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
210000000056 organ Anatomy 0.000 description 4
230000004044 response Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000126 substance Substances 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000003420 antiserotonin agent Substances 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009870 specific binding Effects 0.000 description 3
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 3
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
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 2
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 2
BOHJSUWGUHQCDO-UHFFFAOYSA-N 3-acetyloxy-5-[(4-methoxyphenyl)methylamino]-5-oxopent-2-enoic acid Chemical compound COC1=CC=C(CNC(=O)CC(OC(C)=O)=CC(O)=O)C=C1 BOHJSUWGUHQCDO-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
FCEKDEBSESGRDL-UHFFFAOYSA-N 4-(2-hydroxyethyl)-1-methyl-2-oxoquinoline-6-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCO)=CC(=O)N(C)C2=C1 FCEKDEBSESGRDL-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000027455 binding Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000009989 contractile response Effects 0.000 description 2
230000008602 contraction Effects 0.000 description 2
OCXGTPDKNBIOTF-UHFFFAOYSA-N dibromo(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 OCXGTPDKNBIOTF-UHFFFAOYSA-N 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
210000003752 saphenous vein Anatomy 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000007944 thiolates Chemical class 0.000 description 2
230000002537 thrombolytic effect Effects 0.000 description 2
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
PCNXPHMCSOGYBN-UHFFFAOYSA-N 1-bromo-n-methylmethanesulfonamide Chemical compound CNS(=O)(=O)CBr PCNXPHMCSOGYBN-UHFFFAOYSA-N 0.000 description 1
LJOWXAVFQRZSRJ-UHFFFAOYSA-N 2-(1,2-dihydroquinolin-2-yl)acetic acid Chemical compound C1=CC=C2C=CC(CC(=O)O)NC2=C1 LJOWXAVFQRZSRJ-UHFFFAOYSA-N 0.000 description 1
PPRXDTMAYMNTSV-UHFFFAOYSA-N 2-(6-chloro-1-methyl-2-oxoquinolin-4-yl)acetic acid Chemical compound C1=C(Cl)C=C2C(CC(O)=O)=CC(=O)N(C)C2=C1 PPRXDTMAYMNTSV-UHFFFAOYSA-N 0.000 description 1
NZVXGVBWKLNEDV-UHFFFAOYSA-N 2-(6-cyano-1-methyl-2-oxoquinolin-4-yl)acetic acid Chemical compound C1=C(C#N)C=C2C(CC(O)=O)=CC(=O)N(C)C2=C1 NZVXGVBWKLNEDV-UHFFFAOYSA-N 0.000 description 1
BXZAMTBIPGEPCY-UHFFFAOYSA-N 2-(6-methoxy-1-methyl-2-oxoquinolin-4-yl)acetic acid Chemical compound CN1C(=O)C=C(CC(O)=O)C2=CC(OC)=CC=C21 BXZAMTBIPGEPCY-UHFFFAOYSA-N 0.000 description 1
VGFPQMGFJQAUFB-UHFFFAOYSA-N 2-(6-methoxy-2-oxo-1h-quinolin-4-yl)acetic acid Chemical compound N1C(=O)C=C(CC(O)=O)C2=CC(OC)=CC=C21 VGFPQMGFJQAUFB-UHFFFAOYSA-N 0.000 description 1
DZWWOSFEOQILFN-UHFFFAOYSA-N 2-[7-fluoro-2-oxo-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]quinolin-1-yl]acetamide;hydrochloride Chemical compound Cl.C=1C(=O)N(CC(=O)N)C2=CC(F)=CC=C2C=1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 DZWWOSFEOQILFN-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
QPIOVNJLOVNTMW-UHFFFAOYSA-N 2-bromo-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CBr QPIOVNJLOVNTMW-UHFFFAOYSA-N 0.000 description 1
LBVZINOLAFTARU-UHFFFAOYSA-N 2-bromo-n-methylacetamide Chemical compound CNC(=O)CBr LBVZINOLAFTARU-UHFFFAOYSA-N 0.000 description 1
RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 1
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
SJLMITFMNDOSJI-UHFFFAOYSA-N 3-acetyloxy-5-[(4-chlorophenyl)methylamino]-5-oxopent-2-enoic acid Chemical compound CC(=O)OC(=CC(O)=O)CC(=O)NCC1=CC=C(Cl)C=C1 SJLMITFMNDOSJI-UHFFFAOYSA-N 0.000 description 1
NYUZDKTZMGZBNA-UHFFFAOYSA-N 3-acetyloxy-5-[(4-fluorophenyl)methylamino]-5-oxopent-2-enoic acid Chemical compound CC(=O)OC(=CC(O)=O)CC(=O)NCC1=CC=C(F)C=C1 NYUZDKTZMGZBNA-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
YOEGEAHPQGODAE-UHFFFAOYSA-N 4-(2-bromoethyl)-1-methyl-2-oxoquinoline-6-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCBr)=CC(=O)N(C)C2=C1 YOEGEAHPQGODAE-UHFFFAOYSA-N 0.000 description 1
FRGGVDJQPNKQCS-UHFFFAOYSA-N 4-(2-chloroethyl)-6-fluoro-1-methylquinolin-2-one Chemical compound C1=C(F)C=C2C(CCCl)=CC(=O)N(C)C2=C1 FRGGVDJQPNKQCS-UHFFFAOYSA-N 0.000 description 1
ZBNXJBFROPBBCC-UHFFFAOYSA-N 4-(2-chloroethyl)-6-methoxy-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCCl)C2=CC(OC)=CC=C21 ZBNXJBFROPBBCC-UHFFFAOYSA-N 0.000 description 1
UOSXHELVDCMRDP-UHFFFAOYSA-N 4-(2-chloroethyl)-6-nitro-1h-quinolin-2-one Chemical compound N1C(=O)C=C(CCCl)C2=CC([N+](=O)[O-])=CC=C21 UOSXHELVDCMRDP-UHFFFAOYSA-N 0.000 description 1
XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
VLWRKVBQUANIGI-UHFFFAOYSA-N 4-fluoro-n-methylaniline Chemical compound CNC1=CC=C(F)C=C1 VLWRKVBQUANIGI-UHFFFAOYSA-N 0.000 description 1
KSLCKYGESXPNNB-UHFFFAOYSA-N 6-amino-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C12=CC(N)=CC=C2NC(=O)C=C1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 KSLCKYGESXPNNB-UHFFFAOYSA-N 0.000 description 1
ZKFJZZHAPNFBGW-UHFFFAOYSA-N 6-chloro-4-(2-chloroethyl)-1-methylquinolin-2-one Chemical compound C1=C(Cl)C=C2C(CCCl)=CC(=O)N(C)C2=C1 ZKFJZZHAPNFBGW-UHFFFAOYSA-N 0.000 description 1
IDEXVWAQOYDAEX-UHFFFAOYSA-N 6-methoxy-1-methyl-4-[2-(4-thieno[3,2-c]pyridin-4-ylpiperazin-1-yl)ethyl]quinolin-2-one Chemical compound C12=CC(OC)=CC=C2N(C)C(=O)C=C1CCN(CC1)CCN1C1=NC=CC2=C1C=CS2 IDEXVWAQOYDAEX-UHFFFAOYSA-N 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
- 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
- A61K31/47—Quinolines; Isoquinolines
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

IL12360096A 1995-09-15 1996-09-12 History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them IL123600A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR9510815A FR2738822B1 (fr)	1995-09-15	1995-09-15	Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique
FR9511083A FR2739100B1 (fr)	1995-09-21	1995-09-21	Derives de 4-(omega-(4-(4-fluorobenzoyl)piperidin-1-yl)- alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique
PCT/FR1996/001401 WO1997010238A1 (fr)	1995-09-15	1996-09-12	Derives de quinolein-2(1h)-one comme antagonistes de la serotonine

Publications (2)

Publication Number	Publication Date
IL123600A0 IL123600A0 (en)	1998-10-30
IL123600A true IL123600A (en)	2001-05-20

Family

ID=26232206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12360096A IL123600A (en)	1995-09-15	1996-09-12	History of quinolone - 2 (1H), their preparation and pharmaceutical preparations containing them

Country Status (29)

Country	Link
US (1)	US5958924A (pl)
EP (1)	EP0850235B1 (pl)
JP (1)	JP3335362B2 (pl)
KR (1)	KR100422850B1 (pl)
CN (1)	CN1094490C (pl)
AR (1)	AR003996A1 (pl)
AT (1)	ATE187172T1 (pl)
AU (1)	AU715879B2 (pl)
BG (1)	BG63779B1 (pl)
BR (1)	BR9610579A (pl)
CA (1)	CA2228038C (pl)
CO (1)	CO4750663A1 (pl)
CZ (1)	CZ288149B6 (pl)
DE (1)	DE69605430T2 (pl)
DK (1)	DK0850235T3 (pl)
EE (1)	EE04116B1 (pl)
ES (1)	ES2142089T3 (pl)
GR (1)	GR3032618T3 (pl)
HU (1)	HU222745B1 (pl)
IL (1)	IL123600A (pl)
NO (1)	NO323841B1 (pl)
NZ (1)	NZ318436A (pl)
PL (1)	PL184808B1 (pl)
RU (1)	RU2167874C2 (pl)
SI (1)	SI0850235T1 (pl)
SK (1)	SK282222B6 (pl)
TR (1)	TR199800464T1 (pl)
UA (1)	UA44332C2 (pl)
WO (1)	WO1997010238A1 (pl)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9610579A (pt) *	1995-09-15	1999-07-06	Sanofi Synthelabo	Derivados de quinolein-2(1H)-ona como antagonistas da serotonina
FR2761067B1 (fr) *	1997-03-20	1999-04-23	Synthelabo	Derives de quinolein-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
FR2797874B1 (fr) *	1999-08-27	2002-03-29	Adir	Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA2398388A1 (en) *	2000-01-20	2001-07-26	Koji Kato	Novel piperidine compound and pharmaceutical thereof
FR2812548B1 (fr) *	2000-08-01	2002-09-20	Sanofi Synthelabo	Utilisation de derives de quinolein-2(1h)-one ou un de leurs sels pharmaceutiquement acceptable pour la preparation d'un medicament destine au traitement de l'insuffisance renale
RU2267485C2 (ru) *	2003-10-07	2006-01-10	Общество С Ограниченной Ответственностью "Асинэкс Медхим"	Производные 3-аминометилхинолона-2 в качестве ингибиторов no-синтетазы и способ их получения, биологически активные соединения и фармацевтическая композиция на их основе
RU2284325C2 (ru) *	2003-12-17	2006-09-27	Общество С Ограниченной Ответственностью "Асинэкс Медхим"	Производные фенил-3-аминометил-хинолона-2 в качестве ингибиторов no-синтетазы, способ их получения, биологически активные соединения и фармацевтическая композиция на их основе
GB0420722D0 (en) *	2004-09-17	2004-10-20	Addex Pharmaceuticals Sa	Novel allosteric modulators
TWI320783B (en)	2005-04-14	2010-02-21	Otsuka Pharma Co Ltd	Heterocyclic compound
TWI417095B (zh)	2006-03-15	2013-12-01	Janssen Pharmaceuticals Inc	１，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途
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1996
- 1996-09-12 BR BR9610579A patent/BR9610579A/pt not_active Application Discontinuation
- 1996-09-12 CA CA002228038A patent/CA2228038C/en not_active Expired - Fee Related
- 1996-09-12 AR ARP960104322A patent/AR003996A1/es active IP Right Grant
- 1996-09-12 EP EP96931112A patent/EP0850235B1/fr not_active Expired - Lifetime
- 1996-09-12 CO CO96048698A patent/CO4750663A1/es unknown
- 1996-09-12 SI SI9630151T patent/SI0850235T1/xx unknown
- 1996-09-12 PL PL96325467A patent/PL184808B1/pl not_active IP Right Cessation
- 1996-09-12 UA UA98031235A patent/UA44332C2/uk unknown
- 1996-09-12 TR TR1998/00464T patent/TR199800464T1/xx unknown
- 1996-09-12 ES ES96931112T patent/ES2142089T3/es not_active Expired - Lifetime
- 1996-09-12 CZ CZ1998786A patent/CZ288149B6/cs not_active IP Right Cessation
- 1996-09-12 WO PCT/FR1996/001401 patent/WO1997010238A1/fr not_active Ceased
- 1996-09-12 IL IL12360096A patent/IL123600A/en not_active IP Right Cessation
- 1996-09-12 SK SK346-98A patent/SK282222B6/sk not_active IP Right Cessation
- 1996-09-12 RU RU98106501/04A patent/RU2167874C2/ru not_active IP Right Cessation
- 1996-09-12 AU AU69919/96A patent/AU715879B2/en not_active Ceased
- 1996-09-12 EE EE9800089A patent/EE04116B1/xx not_active IP Right Cessation
- 1996-09-12 NZ NZ318436A patent/NZ318436A/xx not_active IP Right Cessation
- 1996-09-12 KR KR10-1998-0701920A patent/KR100422850B1/ko not_active Expired - Fee Related
- 1996-09-12 DK DK96931112T patent/DK0850235T3/da active
- 1996-09-12 DE DE69605430T patent/DE69605430T2/de not_active Expired - Lifetime
- 1996-09-12 HU HU9802940A patent/HU222745B1/hu not_active IP Right Cessation
- 1996-09-12 AT AT96931112T patent/ATE187172T1/de active
- 1996-09-12 US US09/011,482 patent/US5958924A/en not_active Expired - Lifetime
- 1996-09-12 JP JP51170797A patent/JP3335362B2/ja not_active Expired - Fee Related
- 1996-09-12 CN CN96198333A patent/CN1094490C/zh not_active Expired - Fee Related
1998
- 1998-03-11 BG BG102316A patent/BG63779B1/bg unknown
- 1998-03-13 NO NO19981141A patent/NO323841B1/no not_active IP Right Cessation
2000
- 2000-02-09 GR GR20000400317T patent/GR3032618T3/el unknown

Also Published As

Publication number	Publication date
NO981141D0 (no)	1998-03-13
NZ318436A (en)	1999-02-25
RU2167874C2 (ru)	2001-05-27
IL123600A0 (en)	1998-10-30
HU222745B1 (hu)	2003-09-29
MX9802028A (es)	1998-09-30
PL184808B1 (pl)	2002-12-31
CZ78698A3 (cs)	1998-06-17
EP0850235B1 (fr)	1999-12-01
SI0850235T1 (en)	2000-04-30
SK34698A3 (en)	1998-08-05
DK0850235T3 (da)	2000-05-29
EE04116B1 (et)	2003-08-15
EP0850235A1 (fr)	1998-07-01
NO323841B1 (no)	2007-07-09
CO4750663A1 (es)	1999-03-31
GR3032618T3 (en)	2000-05-31
CZ288149B6 (en)	2001-05-16
DE69605430T2 (de)	2000-07-13
PL325467A1 (en)	1998-07-20
UA44332C2 (uk)	2002-02-15
NO981141L (no)	1998-05-15
AU6991996A (en)	1997-04-01
SK282222B6 (sk)	2001-12-03
HK1014868A1 (en)	1999-10-08
AU715879B2 (en)	2000-02-10
TR199800464T1 (xx)	1998-05-21
DE69605430D1 (de)	2000-01-05
ES2142089T3 (es)	2000-04-01
KR19990044666A (ko)	1999-06-25
BG63779B1 (bg)	2002-12-29
AR003996A1 (es)	1998-09-30
CA2228038C (en)	2009-04-21
CN1094490C (zh)	2002-11-20
HUP9802940A2 (hu)	1999-05-28
CN1202168A (zh)	1998-12-16
HUP9802940A3 (en)	2001-11-28
CA2228038A1 (en)	1997-03-20
JPH11514982A (ja)	1999-12-21
WO1997010238A1 (fr)	1997-03-20
ATE187172T1 (de)	1999-12-15
BR9610579A (pt)	1999-07-06
KR100422850B1 (ko)	2004-07-23
US5958924A (en)	1999-09-28
BG102316A (en)	1999-03-31
EE9800089A (et)	1998-10-15
JP3335362B2 (ja)	2002-10-15

Legal Events

Date	Code	Title
2001-10-31	FF	Patent granted
2002-09-12	NE	Application for restoration - patent lapsed through non-payment of renewal fees (section 60, patents law, 5727-1967)
2003-03-12	KB	Patent renewed
2006-10-30	KB	Patent renewed
2010-11-30	KB	Patent renewed
2015-04-30	MM9K	Patent not in force due to non-payment of renewal fees

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AU715879B2 (en)	2000-02-10	2(1H)-quinolone derivatives as serotonin antagonists
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JPH0687856A (ja)	1994-03-29	８‐クロロ‐１１‐〔１‐〔（５‐メチル‐３‐ピリジル）メチル〕‐４‐ピペリジリデン〕‐６，１１‐ジヒドロ‐５Ｈ‐ベンゾ〔５，６〕シクロヘプタ〔１，２‐ｂ〕ピリジン
EP0487745A1 (en)	1992-06-03	Pyridine derivative with angiotensin ii antagonism
BG107672A (bg)	2004-01-30	Антагонисти на метаботропни глутамат рецептори
PL165502B1 (pl)	1994-12-30	Sposób wytwarzania nowych pochodnych aminopirymidyny PL PL PL PL PL
CA3016830A1 (en)	2017-09-14	Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof
EP3240783B1 (en)	2018-11-21	New benzimidazole derivatives as antihistamine agents
JPS6346077B2 (pl)	1988-09-13
JPS60214778A (ja)	1985-10-28	Ν置換３，４−ジヒドロピリミジン誘導体ならびにその製造法および用途
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FR2761071A1 (fr)	1998-09-25	Derives de quinolein-2(1h)-one et de dihydroquinolein-2(1h)- one, leur preparation et leur application en therapeutique
CN116848117B (zh)	2026-01-02	作为Wee-1抑制剂的稠环化合物
PL191409B1 (pl)	2006-05-31	Pochodna tiadiazolilopirydazyny, jej zastosowanie i sposób wytwarzania oraz kompozycja farmaceutyczna
JPH07267951A (ja)	1995-10-17	アンジオテンシンｉｉ拮抗剤としての新規イミダゾピリジン誘導体
MXPA98002028A (en)	1998-11-16	Quinolein-2 (1h) -ona derivatives as seroton antagonists
JP2860688B2 (ja)	1999-02-24	インドール誘導体
JPH0625250A (ja)	1994-02-01	チエノ〔３，４−ｄ〕イミダゾール誘導体、その製造法およびそれを含有する循環器官用剤
EP0265947B1 (en)	1990-10-17	Dihydropyridine derivatives, process for their preparation, pharmaceutical composition and use
IE913102A1 (en)	1992-03-11	Therapeutic agents
HK1014868B (en)	2000-10-27	Quinolein-2(1h)-one derivatives as serotonin antagonists
FR2738822A1 (fr)	1997-03-21	Derives de 4-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique
JP2585497B2 (ja)	1997-02-26	アンジオテンシン２拮抗性ピリジン誘導体
FR2739100A1 (fr)	1997-03-28	Derives de 4-(omega-(4-(4-fluorobenzoyl)piperidin-1-yl)- alkyl)quinolein-2(1h)-one, leur preparation et leur application en therapeutique
HK1240223B (en)	2019-09-06	New benzimidazole derivatives as antihistamine agents