ZA200103680B - Benzamide derivatives and their use as APOB-100 secretion inhibitors. - Google Patents
Benzamide derivatives and their use as APOB-100 secretion inhibitors. Download PDFInfo
- Publication number
- ZA200103680B ZA200103680B ZA200103680A ZA200103680A ZA200103680B ZA 200103680 B ZA200103680 B ZA 200103680B ZA 200103680 A ZA200103680 A ZA 200103680A ZA 200103680 A ZA200103680 A ZA 200103680A ZA 200103680 B ZA200103680 B ZA 200103680B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- phenyl
- amide
- carboxylic acid
- biphenyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 4
- 150000003936 benzamides Chemical class 0.000 title description 2
- 230000028327 secretion Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 151
- -1 polycyclic radicals Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- IQOMYCGTGFGDFN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IQOMYCGTGFGDFN-UHFFFAOYSA-N 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 150000003254 radicals Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 31
- 238000006467 substitution reaction Methods 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 125000006413 ring segment Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- HMMQTXASHXABQR-UHFFFAOYSA-N 4-methyl-2-(4-propan-2-ylphenyl)benzoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(C)=CC=C1C(O)=O HMMQTXASHXABQR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- JMJSDHIQIDERGA-UHFFFAOYSA-N 3-methoxy-2-(4-propan-2-ylphenyl)benzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1C1=CC=C(C(C)C)C=C1 JMJSDHIQIDERGA-UHFFFAOYSA-N 0.000 claims description 5
- PBEVLYIOMJEMOA-UHFFFAOYSA-N 3-methyl-2-(4-propan-2-ylphenyl)benzoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=C(C)C=CC=C1C(O)=O PBEVLYIOMJEMOA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005518 carboxamido group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002971 oxazolyl group Chemical class 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- XBWKOWZGGKOHBN-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC(C(F)(F)F)=C1 XBWKOWZGGKOHBN-UHFFFAOYSA-N 0.000 claims description 2
- ILMBLFOACOFDEV-UHFFFAOYSA-N 4-methoxy-2-phenylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(C=2C=CC=CC=2)=C1 ILMBLFOACOFDEV-UHFFFAOYSA-N 0.000 claims description 2
- DGHJKOUXAHNRAP-UHFFFAOYSA-N 4-methyloxadiazole Chemical group CC1=CON=N1 DGHJKOUXAHNRAP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 2
- OKGWPQKATHOJEB-UHFFFAOYSA-N n-[4-[4-[(3-acetylphenyl)methyl]piperazin-1-yl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound CC(=O)C1=CC=CC(CN2CCN(CC2)C=2C=CC(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1 OKGWPQKATHOJEB-UHFFFAOYSA-N 0.000 claims description 2
- UZTYCZDKDFFKGD-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-2-phenoxybenzamide Chemical compound C=1C=CC=C(OC=2C=CC=CC=2)C=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC(C#N)=C1 UZTYCZDKDFFKGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- AFVUJJNEILZYJQ-UHFFFAOYSA-N 1-[4-(4-aminophenyl)-1-piperazinyl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N)C=C1 AFVUJJNEILZYJQ-UHFFFAOYSA-N 0.000 claims 1
- CQHDMGPUOAEHTD-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)benzoic acid Chemical compound CC1=CC(C)=CC=C1C1=CC=CC=C1C(O)=O CQHDMGPUOAEHTD-UHFFFAOYSA-N 0.000 claims 1
- CYPULEPXAXULTM-UHFFFAOYSA-N 2-(4-ethylphenyl)benzoic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=CC=C1C(O)=O CYPULEPXAXULTM-UHFFFAOYSA-N 0.000 claims 1
- IPLPMLYQQDEHHD-UHFFFAOYSA-N 2-(4-methoxyphenyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1C(O)=O IPLPMLYQQDEHHD-UHFFFAOYSA-N 0.000 claims 1
- ZTBDDZNRMUSDEN-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)benzoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=CC=C1C(O)=O ZTBDDZNRMUSDEN-UHFFFAOYSA-N 0.000 claims 1
- GPGMUYMJVMCVAK-UHFFFAOYSA-N 3-[[4-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]piperazin-1-yl]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CN2CCN(CC2)C=2C=CC(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1 GPGMUYMJVMCVAK-UHFFFAOYSA-N 0.000 claims 1
- PUWYOKWULRGDMN-UHFFFAOYSA-N 4-chloro-2-(4-propan-2-ylphenyl)benzoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(Cl)=CC=C1C(O)=O PUWYOKWULRGDMN-UHFFFAOYSA-N 0.000 claims 1
- FFXVVIXBXBQZLL-UHFFFAOYSA-N 4-methyl-2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound CC1=CC=C(C(O)=O)C(C=2C=CC(=CC=2)C(F)(F)F)=C1 FFXVVIXBXBQZLL-UHFFFAOYSA-N 0.000 claims 1
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- 241000006460 Cyana Species 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- IFPFSVVTZDBISK-UHFFFAOYSA-N ethyl 2-[4-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IFPFSVVTZDBISK-UHFFFAOYSA-N 0.000 claims 1
- UBMHKIQQMDQJFE-UHFFFAOYSA-N n-[4-[4-(3-cyanobenzoyl)piperazin-1-yl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(N2CCN(CC2)C(=O)C=2C=C(C=CC=2)C#N)C=C1 UBMHKIQQMDQJFE-UHFFFAOYSA-N 0.000 claims 1
- ANJAKNGINXFPRE-UHFFFAOYSA-N n-[4-[4-(furan-2-ylmethyl)piperazin-1-yl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(N2CCN(CC=3OC=CC=3)CC2)C=C1 ANJAKNGINXFPRE-UHFFFAOYSA-N 0.000 claims 1
- TXYAGPLFSDMXFV-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-2-(4-fluorophenyl)benzamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(N2CCN(CC=3C=C(C=CC=3)C#N)CC2)C=C1 TXYAGPLFSDMXFV-UHFFFAOYSA-N 0.000 claims 1
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- KXNJKSBHOPAOJE-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-3-methoxy-2-(4-propan-2-ylphenyl)benzamide Chemical compound C=1C=C(C(C)C)C=CC=1C=1C(OC)=CC=CC=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC(C#N)=C1 KXNJKSBHOPAOJE-UHFFFAOYSA-N 0.000 claims 1
- WIDDDQISDYVWLB-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-3-methoxy-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1C(OC)=CC=CC=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC(C#N)=C1 WIDDDQISDYVWLB-UHFFFAOYSA-N 0.000 claims 1
- KTRNKMSJCSDRJG-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-3-methyl-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1C(C)=CC=CC=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC(C#N)=C1 KTRNKMSJCSDRJG-UHFFFAOYSA-N 0.000 claims 1
- DRHBVJOJNZUTJX-UHFFFAOYSA-N n-[4-[4-[(3-fluorophenyl)methyl]piperazin-1-yl]phenyl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound FC1=CC=CC(CN2CCN(CC2)C=2C=CC(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1 DRHBVJOJNZUTJX-UHFFFAOYSA-N 0.000 claims 1
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- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- HXFGSJBBIKUTOW-UHFFFAOYSA-N methyl 3-[[4-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]piperazin-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2CCN(CC2)C=2C=CC(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=C1 HXFGSJBBIKUTOW-UHFFFAOYSA-N 0.000 description 1
- LRFVEICOELGZOF-UHFFFAOYSA-N methyl 3-methoxy-2-(4-propan-2-ylphenyl)benzoate Chemical compound COC(=O)C1=CC=CC(OC)=C1C1=CC=C(C(C)C)C=C1 LRFVEICOELGZOF-UHFFFAOYSA-N 0.000 description 1
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- MBWHJGVNRSSNDZ-UHFFFAOYSA-N n-[4-[4-(2-amino-2-oxoethyl)piperazin-1-yl]phenyl]-3-methoxy-2-(4-propan-2-ylphenyl)benzamide Chemical compound C=1C=C(C(C)C)C=CC=1C=1C(OC)=CC=CC=1C(=O)NC(C=C1)=CC=C1N1CCN(CC(N)=O)CC1 MBWHJGVNRSSNDZ-UHFFFAOYSA-N 0.000 description 1
- CSJISFGCRJPEDJ-UHFFFAOYSA-N n-[4-[4-(2-amino-2-oxoethyl)piperazin-1-yl]phenyl]-3-methyl-2-(4-propan-2-ylphenyl)benzamide Chemical compound C1=CC(C(C)C)=CC=C1C1=C(C)C=CC=C1C(=O)NC1=CC=C(N2CCN(CC(N)=O)CC2)C=C1 CSJISFGCRJPEDJ-UHFFFAOYSA-N 0.000 description 1
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- WZKMJAVHKZMGDV-UHFFFAOYSA-N n-[4-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-2-pyrrol-1-ylbenzamide Chemical compound C=1C=CC=C(N2C=CC=C2)C=1C(=O)NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC(C#N)=C1 WZKMJAVHKZMGDV-UHFFFAOYSA-N 0.000 description 1
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- GCSOXUVISUKQBS-UHFFFAOYSA-N tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC(N)=C1 GCSOXUVISUKQBS-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9826412.0A GB9826412D0 (en) | 1998-12-03 | 1998-12-03 | Chemical compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200103680B true ZA200103680B (en) | 2002-06-14 |
Family
ID=10843463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200103680A ZA200103680B (en) | 1998-12-03 | 2001-05-07 | Benzamide derivatives and their use as APOB-100 secretion inhibitors. |
Country Status (22)
Country | Link |
---|---|
US (1) | US6552022B1 (no) |
EP (1) | EP1135378A1 (no) |
JP (1) | JP2002531444A (no) |
KR (1) | KR20010081112A (no) |
CN (1) | CN1131222C (no) |
AR (1) | AR021434A1 (no) |
AU (1) | AU750259B2 (no) |
BR (1) | BR9915895A (no) |
CA (1) | CA2353394A1 (no) |
CO (1) | CO5140117A1 (no) |
CZ (1) | CZ20011973A3 (no) |
GB (1) | GB9826412D0 (no) |
HU (1) | HUP0104497A3 (no) |
IL (1) | IL142913A0 (no) |
NO (1) | NO20012688D0 (no) |
NZ (1) | NZ511481A (no) |
PE (1) | PE20001562A1 (no) |
PL (1) | PL348042A1 (no) |
TR (1) | TR200101513T2 (no) |
TW (1) | TW515796B (no) |
WO (1) | WO2000032582A1 (no) |
ZA (1) | ZA200103680B (no) |
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US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
AU6824700A (en) * | 1999-07-20 | 2001-02-05 | Novartis Ag | Organic compounds |
ES2240420T3 (es) * | 2000-01-18 | 2005-10-16 | Novartis Ag | Carboxamidas utiles como inhibidores de la proteina de transferencia de trigliceridos microsomicos y de la secrecion de apolipoproteina b. |
GB0013378D0 (en) * | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Use of therapeutic benzamide derivatives |
GB0013383D0 (en) * | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
GB0013346D0 (en) * | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
JO2654B1 (en) * | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
IL155196A0 (en) * | 2000-10-05 | 2003-11-23 | Fujisawa Pharmaceutical Co | Benzamide derivatives and pharmaceutical compositions containing the same |
JO2409B1 (en) | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
DE10101150A1 (de) | 2001-01-12 | 2002-07-18 | Bayer Ag | Verfahren zur Herstellung trifluormethyl-substituierter Biphenylcarbonsäuren und neue trichlormethyl-und trifluormethyl-substituierte Biphenylcarbonitrile |
JP2004520346A (ja) * | 2001-01-15 | 2004-07-08 | グラクソ グループ リミテッド | Ldl受容体発現のインデューサーとしてのアリールピペリジン誘導体 |
EP1351937A1 (en) * | 2001-01-15 | 2003-10-15 | Glaxo Group Limited | Aryl piperidine derivatives as inducers of ldl-receptor expression |
US20040077654A1 (en) * | 2001-01-15 | 2004-04-22 | Bouillot Anne Marie Jeanne | Aryl piperidine and piperazine derivatives as inducers of ldl-receptor expression |
JO2390B1 (en) * | 2001-04-06 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Diphenylcarboxamides act as lipid-lowering agents |
GB0109287D0 (en) * | 2001-04-12 | 2001-05-30 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
BR0209932A (pt) | 2001-05-22 | 2004-10-13 | Neurogen Corp | Composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, preparação farmacêutica embalada, métodos para modular ligação de mch a um receptor de mch e de mvc, para alterar a atividade de transdução de sinal de um receptor de mch em uma célula, para tratar uma doença ou distúrbio associado com a ativação de receptor de mch patogênico obesidade e para determinar a presença ou ausência de receptor de mch em uma amostra, e, uso de um composto |
EP1935885A3 (en) * | 2001-05-22 | 2008-10-15 | Neurogen Corporation | Melanin concentrating hormone receptor ligands : substituted 1-benzyl-4-aryl piperazine analogues. |
WO2002098839A1 (fr) * | 2001-06-01 | 2002-12-12 | Tanabe Seiyaku Co., Ltd. | Biphenylcarboxamides et procede de preparation de ceux-ci |
US6727264B1 (en) | 2001-07-05 | 2004-04-27 | Synaptic Pharmaceutical Corporation | Substituted anilinic piperidines as MCH selective antagonists |
AU2002344567A1 (en) * | 2001-11-28 | 2003-06-10 | Daiso Co., Ltd. | Heterocyclic amide compounds as apolipoprotein b inhibitors |
GB0129013D0 (en) * | 2001-12-04 | 2002-01-23 | Glaxo Group Ltd | Compounds |
GB0129015D0 (en) * | 2001-12-04 | 2002-01-23 | Glaxo Group Ltd | Compounds |
CN1943786A (zh) | 2002-02-28 | 2007-04-11 | 日本烟草产业株式会社 | 酯化合物及其医药用途 |
UA79300C2 (en) | 2002-08-12 | 2007-06-11 | Janssen Pharmaceutica Nv | N-aryl piperidine substituted biphenylcarboxamides as inhibitors of apolipoprotein b secretion |
WO2004039795A2 (en) * | 2002-10-29 | 2004-05-13 | Fujisawa Pharmaceutical Co., Ltd. | Amide compounds for the treatment of hyperlipidemia |
EP1669345A4 (en) | 2003-08-29 | 2008-02-20 | Japan Tobacco Inc | ESTER DERIVATIVE AND MEDICAL USE THEREOF |
UA83510C2 (en) * | 2003-12-09 | 2008-07-25 | Янссен Фармацевтика Н.В. | N-aryl piperidine substituted biphenylcarboxamides as inhibitors of apolipoprotein b |
JP4846709B2 (ja) * | 2004-03-10 | 2011-12-28 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 5員複素環で置換されているmtp阻害性アリールピペリジン若しくはピペラジン |
EP1799664A1 (en) | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
BRPI0515505A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e sua utilização como inibidores da estearoil-coa desaturase |
CA2580787A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
CA2580845A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
EP1799668A1 (en) | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
US8541457B2 (en) | 2005-06-03 | 2013-09-24 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors |
GB0521244D0 (en) | 2005-10-19 | 2005-11-30 | Astrazeneca Ab | Benzamide compounds |
US8183239B2 (en) * | 2005-10-31 | 2012-05-22 | Janssen Pharmaceutica Nv | Substituted piperazines and piperidines as modulators of the neuropeptide Y2 receptor |
JO2653B1 (en) | 2006-10-24 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Tetrahydroflavin 1-carboxylic acid substituted with pyridine or pyrazine inhibit MTB |
JP5525261B2 (ja) * | 2006-10-24 | 2014-06-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Mtp阻害性テトラヒドロ−ナフタレン−1−カルボン酸誘導体 |
JO2972B1 (en) * | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
WO2008148868A1 (en) | 2007-06-08 | 2008-12-11 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
WO2008148840A1 (en) | 2007-06-08 | 2008-12-11 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
WO2008148851A1 (en) | 2007-06-08 | 2008-12-11 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
JP5579170B2 (ja) | 2008-06-05 | 2014-08-27 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Dgat阻害剤とppar作動薬を含有する薬剤組み合わせ物 |
EA201001847A1 (ru) * | 2008-06-11 | 2011-08-30 | Айрм Ллк | Соединения и композиции, применяемые для лечения малярии |
EP2523664A4 (en) * | 2010-01-13 | 2013-06-26 | Tempero Pharmaceuticals Inc | COMPOUNDS AND METHODS |
MA43706B1 (fr) | 2016-03-17 | 2020-09-30 | Hoffmann La Roche | Dérivé de 5-éthyl-4-méthyl-pyrazole-3-carboxamide ayant une activité en tant qu'agoniste de taar |
AR109304A1 (es) | 2016-08-10 | 2018-11-21 | Sumitomo Chemical Co | Compuesto de oxadiazol y su uso |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES291187A1 (es) * | 1963-04-04 | 1964-01-16 | American Cyanamid Co | Un procedimiento para preparar piperazinas sustituidas |
US4022900A (en) | 1970-09-09 | 1977-05-10 | Marion Laboratories, Inc. | Compositions containing 1,2,3,4-tetrahydroisoquinolines used as hypotensive agents |
GB9119932D0 (en) | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
GB9119920D0 (en) * | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
DE69232003T2 (de) * | 1991-09-18 | 2002-04-25 | Glaxo Group Ltd | Benzanilidderivate als 5-HT1D-Antagonisten |
WO1996040640A1 (en) | 1995-06-07 | 1996-12-19 | Pfizer Inc. | BIPHENYL-2-CARBOXYLIC ACID-TETRAHYDRO-ISOQUINOLIN-6-YL AMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN AND/OR APOLIPOPROTEIN B (Apo B) SECRETION |
CA2272719C (en) * | 1996-11-27 | 2002-10-01 | Pfizer Limited | Apo b-secretion/mtp inhibitory amides |
-
1998
- 1998-12-03 GB GBGB9826412.0A patent/GB9826412D0/en not_active Ceased
-
1999
- 1999-11-30 AR ARP990106079A patent/AR021434A1/es not_active Application Discontinuation
- 1999-12-01 AU AU16566/00A patent/AU750259B2/en not_active Ceased
- 1999-12-01 CA CA002353394A patent/CA2353394A1/en not_active Abandoned
- 1999-12-01 NZ NZ511481A patent/NZ511481A/en unknown
- 1999-12-01 CN CN99815925A patent/CN1131222C/zh not_active Expired - Lifetime
- 1999-12-01 PE PE1999001202A patent/PE20001562A1/es not_active Application Discontinuation
- 1999-12-01 IL IL14291399A patent/IL142913A0/xx unknown
- 1999-12-01 CO CO99075519A patent/CO5140117A1/es unknown
- 1999-12-01 TR TR2001/01513T patent/TR200101513T2/xx unknown
- 1999-12-01 BR BR9915895-7A patent/BR9915895A/pt not_active IP Right Cessation
- 1999-12-01 US US09/831,844 patent/US6552022B1/en not_active Expired - Fee Related
- 1999-12-01 JP JP2000585224A patent/JP2002531444A/ja active Pending
- 1999-12-01 KR KR1020017006936A patent/KR20010081112A/ko not_active Application Discontinuation
- 1999-12-01 HU HU0104497A patent/HUP0104497A3/hu unknown
- 1999-12-01 EP EP99959369A patent/EP1135378A1/en not_active Withdrawn
- 1999-12-01 CZ CZ20011973A patent/CZ20011973A3/cs unknown
- 1999-12-01 WO PCT/EP1999/009320 patent/WO2000032582A1/en not_active Application Discontinuation
- 1999-12-01 PL PL99348042A patent/PL348042A1/xx not_active Application Discontinuation
- 1999-12-06 TW TW088121321A patent/TW515796B/zh not_active IP Right Cessation
-
2001
- 2001-05-07 ZA ZA200103680A patent/ZA200103680B/en unknown
- 2001-05-31 NO NO20012688A patent/NO20012688D0/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2000032582A1 (en) | 2000-06-08 |
GB9826412D0 (en) | 1999-01-27 |
CN1131222C (zh) | 2003-12-17 |
NO20012688L (no) | 2001-05-31 |
CA2353394A1 (en) | 2000-06-08 |
AU1656600A (en) | 2000-06-19 |
JP2002531444A (ja) | 2002-09-24 |
CO5140117A1 (es) | 2002-03-22 |
AR021434A1 (es) | 2002-07-17 |
CN1334808A (zh) | 2002-02-06 |
TR200101513T2 (tr) | 2001-10-22 |
PL348042A1 (en) | 2002-05-06 |
CZ20011973A3 (cs) | 2001-09-12 |
HUP0104497A3 (en) | 2002-07-29 |
EP1135378A1 (en) | 2001-09-26 |
NO20012688D0 (no) | 2001-05-31 |
TW515796B (en) | 2003-01-01 |
KR20010081112A (ko) | 2001-08-27 |
IL142913A0 (en) | 2002-04-21 |
BR9915895A (pt) | 2001-08-21 |
HUP0104497A2 (hu) | 2002-05-29 |
AU750259B2 (en) | 2002-07-11 |
NZ511481A (en) | 2003-11-28 |
PE20001562A1 (es) | 2001-01-26 |
US6552022B1 (en) | 2003-04-22 |
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