AP282A - Novel derivatives of (p. substituted phenyl) oxybutane amines, their processes of production and the pharmaceutical compositions containing them. - Google Patents

Novel derivatives of (p. substituted phenyl) oxybutane amines, their processes of production and the pharmaceutical compositions containing them. Download PDF

Info

Publication number: AP282A
Authority: AP; ARIPO
Prior art keywords: formula; compound; group; derivative; hal
Prior art date: 1990-10-17

Application number

APAP/P/1991/000328A

Other languages

English (en)

Other versions

AP9100328A0 (en

Inventor

Paule Bonnet

Remi Delansorne

Maurice Faure

Michel Lanquetin

Serge Zunino

Original Assignee

Laboratoire Theramex

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.)

1990-10-17

Filing date

1991-10-17

Publication date

1993-09-08

1991-10-17 Application filed by Laboratoire Theramex filed Critical Laboratoire Theramex

1991-10-31 Publication of AP9100328A0 publication Critical patent/AP9100328A0/xx

1993-09-08 Application granted granted Critical

1993-09-08 Publication of AP282A publication Critical patent/AP282A/en

Links

238000000034 method Methods 0.000 title claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
150000001412 amines Chemical class 0.000 title claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title abstract description 5
239000004480 active ingredient Substances 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 69
-1 4-substitutedphenyl Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
NZXGDKLTTHIYTB-UHFFFAOYSA-N 2-piperazin-1-yl-1h-benzimidazole Chemical class C1CNCCN1C1=NC2=CC=CC=C2N1 NZXGDKLTTHIYTB-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
125000001743 benzylic group Chemical group 0.000 claims description 5
229940075420 xanthine Drugs 0.000 claims description 5
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 4
YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical compound ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 claims description 4
230000000144 pharmacologic effect Effects 0.000 claims description 4
150000004986 phenylenediamines Chemical class 0.000 claims description 4
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
XPLSBZLHKGHHDJ-UHFFFAOYSA-N 8-piperazin-1-yl-3,7-dihydropurine-2,6-dione Chemical class N1C=2C(=O)NC(=O)NC=2N=C1N1CCNCC1 XPLSBZLHKGHHDJ-UHFFFAOYSA-N 0.000 claims description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 3
150000001556 benzimidazoles Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims description 2
BIXPVMGMGJHDSI-UHFFFAOYSA-N 8-(piperidin-1-ylamino)-3,7-dihydropurine-2,6-dione Chemical class N1C=2C(=O)NC(=O)NC=2N=C1NN1CCCCC1 BIXPVMGMGJHDSI-UHFFFAOYSA-N 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
239000001273 butane Substances 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
150000004292 cyclic ethers Chemical class 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
HZCHWCXWHAUOLH-UHFFFAOYSA-N n-piperidin-1-yl-1h-benzimidazol-2-amine Chemical compound C1CCCCN1NC1=NC2=CC=CC=C2N1 HZCHWCXWHAUOLH-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000005646 oximino group Chemical group 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
150000003527 tetrahydropyrans Chemical class 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims 1
201000009961 allergic asthma Diseases 0.000 claims 1
208000026935 allergic disease Diseases 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical class CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 1
229910052742 iron Inorganic materials 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
239000007800 oxidant agent Substances 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
150000004885 piperazines Chemical class 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
230000011514 reflex Effects 0.000 claims 1
125000003277 amino group Chemical group 0.000 abstract description 3
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical class CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000000047 product Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000002211 ultraviolet spectrum Methods 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000000155 melt Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LCPFEKUSZCVXOD-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-1-chlorobutan-1-ol Chemical compound CCCC(O)(Cl)C1=CC=C(C(C)(C)C)C=C1 LCPFEKUSZCVXOD-UHFFFAOYSA-N 0.000 description 2
YKSVXVKIYYQWBB-UHFFFAOYSA-N 1-butylpiperazine Chemical compound CCCCN1CCNCC1 YKSVXVKIYYQWBB-UHFFFAOYSA-N 0.000 description 2
AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
HDDNMPHXSUSADO-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NCC1=CC=C(F)C=C1 HDDNMPHXSUSADO-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
VRJHQPZVIGNGMX-UHFFFAOYSA-N piperidine-4-one Natural products O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
229960000278 theophylline Drugs 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
FGFWTHUIJBKWIR-UHFFFAOYSA-N 1-(9h-xanthen-9-yl)piperazine Chemical compound C1CNCCN1C1C2=CC=CC=C2OC2=CC=CC=C21 FGFWTHUIJBKWIR-UHFFFAOYSA-N 0.000 description 1
IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
UBXGZTRRRHVEAJ-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-2-piperazin-1-ylbenzimidazole Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1N1CCNCC1 UBXGZTRRRHVEAJ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
PXOHMAGZUFXBSG-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)-4-chlorobutoxy]oxane Chemical compound C1=CC(C(C)(C)C)=CC=C1C(Cl)CCCOC1OCCCC1 PXOHMAGZUFXBSG-UHFFFAOYSA-N 0.000 description 1
PGXALMVNIRPELS-UHFFFAOYSA-N 2-chloro-1-[(4-fluorophenyl)methyl]benzimidazole Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1Cl PGXALMVNIRPELS-UHFFFAOYSA-N 0.000 description 1
QWBBOBUOKAVBBW-UHFFFAOYSA-N 2-chloro-4-[(4-fluorophenyl)methyl]-1h-benzimidazole Chemical compound C1=CC(F)=CC=C1CC1=CC=CC2=C1NC(Cl)=N2 QWBBOBUOKAVBBW-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
XCHUSIDICONYDX-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-chlorobutan-1-ol Chemical compound CC(C)(C)C1=CC=C(C(Cl)CCCO)C=C1 XCHUSIDICONYDX-UHFFFAOYSA-N 0.000 description 1
CTPZWLAIYOQCNW-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-chlorobutan-2-one Chemical compound CC(=O)CC(Cl)C1=CC=C(C(C)(C)C)C=C1 CTPZWLAIYOQCNW-UHFFFAOYSA-N 0.000 description 1
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
LKMOVYWEDIGANL-UHFFFAOYSA-N 8-chloro-7-[(4-fluorophenyl)methyl]-1,3-dimethylpurine-2,6-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=C(Cl)N1CC1=CC=C(F)C=C1 LKMOVYWEDIGANL-UHFFFAOYSA-N 0.000 description 1
RYIGNEOBDRVTHA-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2 RYIGNEOBDRVTHA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241001072332 Monia Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 1
229960004754 astemizole Drugs 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000013844 butane Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940046892 lead acetate Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000005334 phenylbutanes Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000003643 water by type Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

APAP/P/1991/000328A 1990-10-17 1991-10-17 Novel derivatives of (p. substituted phenyl) oxybutane amines, their processes of production and the pharmaceutical compositions containing them. AP282A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR909012562A FR2668150B1 (fr)	1990-10-17	1990-10-17	Nouveaux derives du terbutylphenyl 1-amino 4-hydroxybutane, leurs procedes de preparation et les compositions pharmaceutiques en renfermant.

Publications (2)

Publication Number	Publication Date
AP9100328A0 AP9100328A0 (en)	1991-10-31
AP282A true AP282A (en)	1993-09-08

Family

ID=9401134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1991/000328A AP282A (en)	1990-10-17	1991-10-17	Novel derivatives of (p. substituted phenyl) oxybutane amines, their processes of production and the pharmaceutical compositions containing them.

Country Status (23)

Country	Link
US (1)	US5461059A (pl)
EP (1)	EP0505543A1 (pl)
JP (1)	JPH05503298A (pl)
KR (1)	KR927003589A (pl)
AP (1)	AP282A (pl)
BG (1)	BG60680B1 (pl)
BR (1)	BR9106188A (pl)
CA (1)	CA2071911A1 (pl)
CZ (1)	CZ182292A3 (pl)
FI (1)	FI922773L (pl)
FR (2)	FR2668150B1 (pl)
HU (1)	HUT61297A (pl)
IE (1)	IE913636A1 (pl)
IL (1)	IL99776A0 (pl)
MA (1)	MA22321A1 (pl)
NO (1)	NO922358L (pl)
NZ (1)	NZ240274A (pl)
OA (1)	OA09835A (pl)
PL (2)	PL169452B1 (pl)
PT (1)	PT99266A (pl)
RO (1)	RO108241B1 (pl)
WO (1)	WO1992006977A1 (pl)
ZA (1)	ZA918282B (pl)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2048109B1 (es) *	1992-07-20	1994-12-16	Espanola Prod Quimicos	Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol.
CA2161876A1 (en) *	1993-05-20	1994-12-08	Den-Ichi Momose	1-(2-benzimidazolyl)-1,5-diazacyclooctane compounds
ES2072193B1 (es) *	1993-05-21	1996-02-16	Espanola Prod Quimicos	Nuevos derivados del1-fenilmetil bencimidazol piperacinas.
US5691323A (en) *	1995-05-12	1997-11-25	Merck & Co., Inc.	Muscarine antagonists
FR2727865B1 (fr) *	1994-12-08	1997-07-18	Esteve Labor Dr	Utilisation des derives de 2-(4-(azolybutyl)-piperazinyl- (methyl))-benzimidazole et analogues ainsi que de leurs sels, pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme
WO1997036592A1 (en) *	1996-04-03	1997-10-09	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
MXPA02012272A (es) *	2000-07-04	2003-04-25	Novo Nordisk As	Compuestos heterociclicos que son inhibidores de la enzima dipeptidilpeptidasa-iv.
WO2004009091A1 (en) *	2002-06-17	2004-01-29	Glaxo Group Limited	Purine derivatives as liver x receptor agonists

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US4695575A (en) *	1984-11-13	1987-09-22	Janssen Pharmaceutica, N.V.	4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines
EP0282133A2 (en) *	1987-03-09	1988-09-14	Janssen Pharmaceutica N.V.	1-alkyl substituted benzimidazole derivatives
US4908372A (en) *	1988-10-13	1990-03-13	Merrell Dow Pharmaceuticals Inc.	Antihistaminic piperidinyl benzimidazoles
EP0393738A1 (en) *	1989-04-07	1990-10-24	Janssen Pharmaceutica N.V.	Hydroxyalkylfuranyl derivatives

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NL297097A (pl) *	1962-08-31
US3161645A (en) *	1962-12-18	1964-12-15	Res Lab Dr C Janssen N V	1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds
US3491103A (en) *	1963-12-19	1970-01-20	Sandoz Ag	Certain 4h-benzo(4,5)cyclohepta-(1,2-b) thiophenes
US4219559A (en) *	1979-01-10	1980-08-26	Janssen Pharmaceutica N.V.	N-Heterocyclyl-4-piperidinamines
JPS5879983A (ja) *	1981-11-06	1983-05-13	Kanebo Ltd	新規なベンズイミダゾ−ル誘導体、その製造法およびその医薬組成物
MY106964A (en) *	1988-04-28	1995-08-30	Schering Corp	Fused polycyclic compounds, compositions, methods of manufacture, and their use as paf antagonists, antihistamines and/or antiinflammatory agents.
US5217980A (en) *	1990-07-19	1993-06-08	Janssen Pharmaceutica N.V.	Oxazolyl and piperidinyl substituted benimidazolyl compounds

1990
- 1990-10-17 FR FR909012562A patent/FR2668150B1/fr not_active Expired - Fee Related
1991
- 1991-10-11 FR FR919112515A patent/FR2670783B1/fr not_active Expired - Fee Related
- 1991-10-16 MA MA22603A patent/MA22321A1/fr unknown
- 1991-10-17 KR KR1019920701452A patent/KR927003589A/ko not_active Ceased
- 1991-10-17 BR BR919106188A patent/BR9106188A/pt not_active Application Discontinuation
- 1991-10-17 EP EP91918443A patent/EP0505543A1/fr not_active Withdrawn
- 1991-10-17 ZA ZA918282A patent/ZA918282B/xx unknown
- 1991-10-17 PL PL91310562A patent/PL169452B1/pl unknown
- 1991-10-17 CA CA002071911A patent/CA2071911A1/fr not_active Abandoned
- 1991-10-17 HU HU922176A patent/HUT61297A/hu unknown
- 1991-10-17 AP APAP/P/1991/000328A patent/AP282A/en active
- 1991-10-17 PL PL91295029A patent/PL169022B1/pl unknown
- 1991-10-17 JP JP3517705A patent/JPH05503298A/ja active Pending
- 1991-10-17 WO PCT/FR1991/000811 patent/WO1992006977A1/fr not_active Ceased
- 1991-10-17 IL IL99776A patent/IL99776A0/xx unknown
- 1991-10-17 PT PT99266A patent/PT99266A/pt not_active Application Discontinuation
- 1991-10-17 FI FI922773A patent/FI922773L/fi not_active Application Discontinuation
- 1991-10-17 NZ NZ240274A patent/NZ240274A/en unknown
- 1991-10-17 RO RO92-0818A patent/RO108241B1/ro unknown
- 1991-10-17 IE IE363691A patent/IE913636A1/en not_active Application Discontinuation
- 1991-10-17 US US07/861,816 patent/US5461059A/en not_active Expired - Fee Related
1992
- 1992-06-15 CZ CS921822A patent/CZ182292A3/cs unknown
- 1992-06-16 BG BG96487A patent/BG60680B1/bg unknown
- 1992-06-16 NO NO92922358A patent/NO922358L/no unknown
- 1992-06-17 OA OA60229A patent/OA09835A/fr unknown

Patent Citations (4)

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Publication number	Priority date	Publication date	Assignee	Title
US4695575A (en) *	1984-11-13	1987-09-22	Janssen Pharmaceutica, N.V.	4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines
EP0282133A2 (en) *	1987-03-09	1988-09-14	Janssen Pharmaceutica N.V.	1-alkyl substituted benzimidazole derivatives
US4908372A (en) *	1988-10-13	1990-03-13	Merrell Dow Pharmaceuticals Inc.	Antihistaminic piperidinyl benzimidazoles
EP0393738A1 (en) *	1989-04-07	1990-10-24	Janssen Pharmaceutica N.V.	Hydroxyalkylfuranyl derivatives

Also Published As

Publication number	Publication date
EP0505543A1 (fr)	1992-09-30
KR927003589A (ko)	1992-12-18
FR2670783B1 (fr)	1994-11-18
HU9202176D0 (en)	1992-10-28
FR2668150B1 (fr)	1994-11-18
FI922773A7 (fi)	1992-06-16
PL169452B1 (pl)	1996-07-31
CZ182292A3 (en)	1993-01-13
MA22321A1 (fr)	1992-07-01
AP9100328A0 (en)	1991-10-31
BG60680B1 (bg)	1995-12-29
NZ240274A (en)	1995-07-26
PT99266A (pt)	1992-08-31
FI922773A0 (fi)	1992-06-16
ZA918282B (en)	1992-07-29
NO922358D0 (no)	1992-06-16
US5461059A (en)	1995-10-24
BR9106188A (pt)	1993-03-16
PL169022B1 (pl)	1996-05-31
JPH05503298A (ja)	1993-06-03
WO1992006977A1 (fr)	1992-04-30
RO108241B1 (ro)	1994-03-31
HUT61297A (en)	1992-12-28
BG96487A (bg)	1993-12-24
NO922358L (no)	1992-08-11
IL99776A0 (en)	1992-08-18
IE913636A1 (en)	1992-04-22
CA2071911A1 (fr)	1992-04-18
FI922773L (fi)	1992-06-16
OA09835A (fr)	1994-08-15
FR2670783A1 (fr)	1992-06-26
FR2668150A1 (fr)	1992-04-24

Publication	Publication Date	Title
US4912219A (en)	1990-03-27	2-[4-pyrimidin-2-yl amino)piperidin-1-yl]benzimidazole compound
US4904666A (en)	1990-02-27	Pyrazolo(3,4-d)pyrimidine compounds, compositions and method of use
US4548820A (en)	1985-10-22	Xanthine compounds
US5877187A (en)	1999-03-02	Benzimidazole derivatives with antihistaminic activity
Dal Piaz et al.	1996	4, 5-Functionalized 6-phenyl-3 (2H)-pyridazinones: synthesis and evaluation of antinociceptive activity
US4904676A (en)	1990-02-27	Amino-oxazole compounds having dopaminergic activity
PL151889B1 (en)	1990-10-31	Method of obtaining novel derivatives of thaizole
CA2063172A1 (en)	1992-09-26	4-aryl-thiazole or imidazole derivatives
NZ197101A (en)	1984-03-16	4,5-dihydro-1,2,4-triazolo(4,3-a)quinoxalin-4-ones
EP0074768A2 (en)	1983-03-23	Alkanoylanilides
US5059601A (en)	1991-10-22	Imidazolone derivatives with activity on central nervous system and antihypertensive activity, preparation methods thereof, and pharmaceutical compositions containing them
SK89693A3 (en)	1994-03-09	New 4,5-dihydro-4-oxopyrolo[1,2-a]-quinoxalines and responsive azaanalogues and method of their preparation
HU185975B (en)	1985-04-28	Process forproducing new, benzoaxazolinone derivatives substituted with an aminoalkohol- or aminoketone chain at the 6 position and pharmaceutically acceptable salts thereof
IE913636A1 (en)	1992-04-22	Novel derivatives of(p.substituted phenyl) oxybutane amines,¹their processes of production and the pharmaceutical¹compositions containing them
US5244894A (en)	1993-09-14	2-aminopyrimidine-4-carboxamide derivatives, their preparation and their use in therapeutics
EP0784055A1 (en)	1997-07-16	Pyrimidinylpyrazole derivative
EP0406739A2 (en)	1991-01-09	Piperidine derivative, method for preparation thereof, and a pharmaceutical composition comprising the same
US4948808A (en)	1990-08-14	Guanidinobenzoic ester derivative
US4603130A (en)	1986-07-29	1-substituted-2-(piperazinyl or homopiperazinyl)-benzimidazole compounds and pharmaceutical composition
US4824836A (en)	1989-04-25	Spiro (4,5) decone compounds
IE921319A1 (en)	1992-11-04	2-aminopyrimidine-4-carboxamide derivatives, their¹preparation and their application in therapy
US5198441A (en)	1993-03-30	Derivatives of 1,2-dihydro 2-oxo quinoxalines, their preparation and their use in therapy
EP0287971B1 (en)	1993-02-24	Benzimidazole derivatives and process for their preparations
AU764468B2 (en)	2003-08-21	Substituted 1-(piperidin-4-yl)-3-(aryl)-isothioureas, their preparation and therapeutic use
Merlos et al.	1990	Structure-activity relationships in a series of xanthine derivatives with antibronchoconstrictory and bronchodilatory activities