OA10479A - Apolipoprotein-b synthesis inhibitors - Google Patents

Apolipoprotein-b synthesis inhibitors Download PDF

Info

Publication number: OA10479A
Authority: OA; OAPI
Prior art keywords: formula; amino; alkyl; methyl; ch2ch3
Prior art date: 1994-10-27

Application number

OA60997A

Other languages

English (en)

Inventor

Jan Heeres

Leo Jacobus Jozef Backx

Robert Jozef Maria Hendrickx

Luc Alfons Leo Van Der Eycken

Didier De Chaffoy D Courcelles

Original Assignee

Janssen Pharmaceutica Nv

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.)

1994-10-27

Filing date

1997-04-25

Publication date

2002-04-09

1995-05-31 Priority claimed from US08/455,304 external-priority patent/US5521186A/en

1997-04-25 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2002-04-09 Publication of OA10479A publication Critical patent/OA10479A/en

Links

101710095342 Apolipoprotein B Proteins 0.000 title description 12
102100040202 Apolipoprotein B-100 Human genes 0.000 title description 12
230000015572 biosynthetic process Effects 0.000 title description 7
238000003786 synthesis reaction Methods 0.000 title description 5
239000003112 inhibitor Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 69
239000000203 mixture Substances 0.000 claims abstract description 35
239000002253 acid Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 9
125000004043 oxo group Chemical group O=* 0.000 claims abstract 2
-1 Cj.^alkyloxy Chemical group 0.000 claims description 32
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 16
125000004953 trihalomethyl group Chemical group 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 12
208000031226 Hyperlipidaemia Diseases 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 6
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
150000003536 tetrazoles Chemical group 0.000 claims description 4
150000003852 triazoles Chemical class 0.000 claims description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
150000002460 imidazoles Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
150000003230 pyrimidines Chemical group 0.000 claims 1
150000004867 thiadiazoles Chemical group 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
150000002431 hydrogen Chemical class 0.000 abstract description 6
150000003839 salts Chemical class 0.000 abstract description 5
239000003524 antilipemic agent Substances 0.000 abstract description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
150000001204 N-oxides Chemical class 0.000 abstract 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 51
239000000243 solution Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
239000000543 intermediate Substances 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
108010007622 LDL Lipoproteins Proteins 0.000 description 10
102000007330 LDL Lipoproteins Human genes 0.000 description 10
239000003480 eluent Substances 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 8
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 7
238000004440 column chromatography Methods 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
201000001320 Atherosclerosis Diseases 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
108010062497 VLDL Lipoproteins Proteins 0.000 description 6
239000007788 liquid Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
101150102415 Apob gene Proteins 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
MOQVHOPVBREXLY-UHFFFAOYSA-N 3h-dioxol-4-ylmethanol Chemical compound OCC1=COOC1 MOQVHOPVBREXLY-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
235000011118 potassium hydroxide Nutrition 0.000 description 4
229940093932 potassium hydroxide Drugs 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
MWRBNPKJOOWZPW-GPADLTIESA-N 1,2-di-[(9E)-octadecenoyl]-sn-glycero-3-phosphoethanolamine Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C\CCCCCCCC MWRBNPKJOOWZPW-GPADLTIESA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
208000035150 Hypercholesterolemia Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
IOCYQQQCJYMWDT-UHFFFAOYSA-N (3-ethyl-2-methoxyquinolin-6-yl)-(4-methoxycyclohexyl)methanone Chemical compound C=1C=C2N=C(OC)C(CC)=CC2=CC=1C(=O)C1CCC(OC)CC1 IOCYQQQCJYMWDT-UHFFFAOYSA-N 0.000 description 2
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 2
229940080296 2-naphthalenesulfonate Drugs 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
210000000941 bile Anatomy 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
239000006187 pill Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229940093956 potassium carbonate Drugs 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229940083542 sodium Drugs 0.000 description 2
235000015424 sodium Nutrition 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
229940083608 sodium hydroxide Drugs 0.000 description 2
239000008107 starch Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
108010071619 Apolipoproteins Proteins 0.000 description 1
102000007592 Apolipoproteins Human genes 0.000 description 1
102000018616 Apolipoproteins B Human genes 0.000 description 1
108010027006 Apolipoproteins B Proteins 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010008635 Cholestasis Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
208000026350 Inborn Genetic disease Diseases 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000002357 Ribes grossularia Nutrition 0.000 description 1
244000171263 Ribes grossularia Species 0.000 description 1
240000007651 Rubus glaucus Species 0.000 description 1
235000011034 Rubus glaucus Nutrition 0.000 description 1
235000009122 Rubus idaeus Nutrition 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 1
MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-N 0.000 description 1
208000037919 acquired disease Diseases 0.000 description 1
206010001584 alcohol abuse Diseases 0.000 description 1
208000025746 alcohol use disease Diseases 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003098 androgen Substances 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000007870 cholestasis Effects 0.000 description 1
231100000359 cholestasis Toxicity 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
108010037444 diisopropylglutathione ester Proteins 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
229940125753 fibrate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
208000016361 genetic disease Diseases 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
208000003532 hypothyroidism Diseases 0.000 description 1
230000002989 hypothyroidism Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
JPYAHQUNMYHNDY-MHECFPHRSA-N n-[(1r,2s)-2-(3,4-dimethoxyphenyl)-7-methoxy-6-propan-2-yloxy-1,2,3,4-tetrahydronaphthalen-1-yl]-n-methylformamide Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H](N(C)C=O)C2=CC(OC)=C(OC(C)C)C=C2CC1 JPYAHQUNMYHNDY-MHECFPHRSA-N 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000004252 protein component Nutrition 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000011002 quantification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- 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
- 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
- A61P3/06—Antihyperlipidemics
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

OA60997A 1994-10-27 1997-04-25 Apolipoprotein-b synthesis inhibitors OA10479A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP94203120		1994-10-27
US08/455,304 US5521186A (en)	1994-10-27	1995-05-31	Apolipoprotein-β synthesis inhibitors

Publications (1)

Publication Number	Publication Date
OA10479A true OA10479A (en)	2002-04-09

Family

ID=26136684

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60997A OA10479A (en)	1994-10-27	1997-04-25	Apolipoprotein-b synthesis inhibitors

Country Status (30)

Country	Link
US (1)	US5929075A (de)
EP (1)	EP0788496B1 (de)
JP (1)	JP3025907B2 (de)
KR (1)	KR100227231B1 (de)
CN (1)	CN1068000C (de)
AP (1)	AP779A (de)
AT (1)	ATE198889T1 (de)
AU (1)	AU697744C (de)
BG (1)	BG63694B1 (de)
BR (1)	BR9509436A (de)
CA (1)	CA2203274C (de)
CY (1)	CY2256B1 (de)
CZ (1)	CZ286476B6 (de)
DE (3)	DE122007000005I2 (de)
DK (1)	DK0788496T3 (de)
ES (1)	ES2155535T3 (de)
FI (1)	FI119548B (de)
GR (1)	GR3035519T3 (de)
HR (1)	HRP950532B1 (de)
HU (1)	HU219862B (de)
IL (1)	IL115771A (de)
LU (1)	LU91306I2 (de)
NO (1)	NO311937B1 (de)
NZ (1)	NZ295353A (de)
OA (1)	OA10479A (de)
PT (1)	PT788496E (de)
RO (1)	RO118715B1 (de)
SK (1)	SK281908B6 (de)
TR (1)	TR199501295A2 (de)
WO (1)	WO1996013499A1 (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20010023729A (ko) *	1997-11-03	2001-03-26	디르크 반테	지질 저하제 조성물
PL358909A1 (en) *	1998-04-27	2004-08-23	Janssen Pharmaceutica N.V.	Pellets having a core coated with a lipid lowering agent and a polymer
NZ512891A (en)	1998-12-22	2003-01-31	Janssen Pharmaceutica Nv	S-oxide lipid lowering compounds
DE19945982A1 (de) *	1999-09-24	2001-03-29	Knoll Ag	Geschwindigkeitsbestimmte Partikel
US20050132022A1 (en) *	2003-12-12	2005-06-16	International Business Machines Corporation	Computer system with LAN-based I/O
JP4994043B2 (ja) *	2004-01-21	2012-08-08	エランコ・アニマル・ヘルス・アイルランド・リミテッド	ミトラタピデ経口用溶液
US7649002B2 (en)	2004-02-04	2010-01-19	Pfizer Inc	(3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists
US7262318B2 (en) *	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
AU2005230397B2 (en) *	2004-04-09	2010-04-08	Elanco Animal Health Ireland Limited	Intermittent dosing regimen for the treatment of overweight with MTP-inhibitors
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
PA8660701A1 (es)	2005-02-04	2006-09-22	Pfizer Prod Inc	Agonistas de pyy y sus usos
EP1890767A2 (de) *	2005-05-27	2008-02-27	Pfizer Products Inc.	Kombinationstherapie zur behandlung von fettleibigkeit oder aufrechterhaltung des gewichtverlusts
CA2617654A1 (en) *	2005-08-04	2007-02-08	Pfizer Limited	Piperidinoyl-pyrrolidine and piperidinoyl-piperidine compounds
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
WO2007096763A2 (en) *	2006-02-23	2007-08-30	Pfizer Limited	Melanocortin type 4 receptor agonist piperidinoylpyrrolidines
US8383660B2 (en)	2006-03-10	2013-02-26	Pfizer Inc.	Dibenzyl amine compounds and derivatives
CN101583593A (zh)	2006-11-13	2009-11-18	辉瑞产品公司	二芳基、二吡啶基和芳基-吡啶基衍生物及其用途
CN101663262B (zh)	2006-12-01	2014-03-26	百时美施贵宝公司	用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物
ES2348530T3 (es)	2007-05-25	2010-12-09	Janssen Pharmaceutica, N.V.	Síntesis mejorada de metanosulfonato de (2s-cis)-2-(bromometil)-2-(4-clorofenil)-1,3 dioxolan-4-metanol (éster).
KR101280786B1 (ko) *	2008-08-06	2013-07-05	화이자 리미티드	멜라노코르틴 4 작용제로서 다이아제핀 및 다이아조칸 화합물
US9040539B2 (en) *	2010-05-19	2015-05-26	Sandoz Ag	Process for the preparation of chiral triazolones
BR112020018094A2 (pt)	2018-03-08	2020-12-22	Incyte Corporation	Compostos de aminopirazina diol como inibidores de pi3k-¿
US11046658B2 (en)	2018-07-02	2021-06-29	Incyte Corporation	Aminopyrazine derivatives as PI3K-γ inhibitors

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4313953A (en) *	1978-06-23	1982-02-02	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4218458A (en) *	1978-06-23	1980-08-19	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4766125A (en) *	1981-06-23	1988-08-23	Janssen Pharmaceutica N.V.	N-aryl-piperazinealkanamides useful for protecting hearts from myocardial injury caused by ischaemia, anoxia or hypoxia
US4619931A (en) *	1983-02-28	1986-10-28	Janssen Pharmaceutica, N.V.	[[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles
CA1292472C (en) *	1985-12-03	1991-11-26	Alfonsus Guilielmus Knaeps	Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl\|-1,3-dioxolan-2-yl\|methyl\|-1h-imidazoles and 1h-1,2,4-triazoles
NZ223799A (en) *	1987-03-25	1989-12-21	Janssen Pharmaceutica Nv	Azolylmethyl-dioxolanylmethoxyphenyl-piperazinyl-phenyl-triazolones and antimicrobial compositions
CA1331757C (en) *	1988-02-29	1994-08-30	Janssen Pharmaceutica Naamloze Vennootschap	5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols
AU6359594A (en) *	1993-03-04	1994-09-26	Cytoven International N.V.	Pharmaceutical tryptophan containing dipeptide compositions and methods of use thereof
US5521186A (en) *	1994-10-27	1996-05-28	Janssen Pharmaceutica N.V.	Apolipoprotein-β synthesis inhibitors

1995
- 1995-10-19 DE DE122007000005C patent/DE122007000005I2/de active Active
- 1995-10-19 RO RO97-00812A patent/RO118715B1/ro unknown
- 1995-10-19 BR BR9509436A patent/BR9509436A/pt not_active IP Right Cessation
- 1995-10-19 NZ NZ295353A patent/NZ295353A/en not_active IP Right Cessation
- 1995-10-19 WO PCT/EP1995/004111 patent/WO1996013499A1/en not_active Ceased
- 1995-10-19 AP APAP/P/1997/000968A patent/AP779A/en active
- 1995-10-19 KR KR1019970702662A patent/KR100227231B1/ko not_active Expired - Fee Related
- 1995-10-19 ES ES95937804T patent/ES2155535T3/es not_active Expired - Lifetime
- 1995-10-19 EP EP95937804A patent/EP0788496B1/de not_active Expired - Lifetime
- 1995-10-19 CA CA002203274A patent/CA2203274C/en not_active Expired - Fee Related
- 1995-10-19 DK DK95937804T patent/DK0788496T3/da active
- 1995-10-19 US US08/817,247 patent/US5929075A/en not_active Expired - Lifetime
- 1995-10-19 CN CN95195885A patent/CN1068000C/zh not_active Expired - Fee Related
- 1995-10-19 DE DE1995619995 patent/DE122007000005I1/de active Pending
- 1995-10-19 AU AU38680/95A patent/AU697744C/en not_active Ceased
- 1995-10-19 DE DE69519995T patent/DE69519995T2/de not_active Expired - Lifetime
- 1995-10-19 PT PT95937804T patent/PT788496E/pt unknown
- 1995-10-19 AT AT95937804T patent/ATE198889T1/de active
- 1995-10-19 SK SK507-97A patent/SK281908B6/sk not_active IP Right Cessation
- 1995-10-19 JP JP8514288A patent/JP3025907B2/ja not_active Expired - Fee Related
- 1995-10-19 HU HU9701956A patent/HU219862B/hu not_active IP Right Cessation
- 1995-10-19 CZ CZ19971198A patent/CZ286476B6/cs not_active IP Right Cessation
- 1995-10-20 TR TR95/01295A patent/TR199501295A2/xx unknown
- 1995-10-26 IL IL11577195A patent/IL115771A/xx not_active IP Right Cessation
- 1995-10-27 HR HR950532A patent/HRP950532B1/xx not_active IP Right Cessation
1997
- 1997-04-10 BG BG101402A patent/BG63694B1/bg unknown
- 1997-04-24 NO NO19971895A patent/NO311937B1/no not_active IP Right Cessation
- 1997-04-25 FI FI971784A patent/FI119548B/fi not_active IP Right Cessation
- 1997-04-25 OA OA60997A patent/OA10479A/en unknown
2001
- 2001-03-05 GR GR20010400359T patent/GR3035519T3/el unknown
2002
- 2002-01-04 CY CY0200004A patent/CY2256B1/xx unknown
2007
- 2007-01-17 LU LU91306C patent/LU91306I2/fr unknown

Also Published As

Publication number	Publication date
DK0788496T3 (da)	2001-06-18
HUT77360A (hu)	1998-03-30
FI119548B (fi)	2008-12-31
FI971784A0 (fi)	1997-04-25
MX9703074A (es)	1997-07-31
AU697744C (en)	2002-08-22
HU219862B (hu)	2001-08-28
CA2203274C (en)	2002-02-19
CA2203274A1 (en)	1996-05-09
NO311937B1 (no)	2002-02-18
JP3025907B2 (ja)	2000-03-27
BR9509436A (pt)	1998-01-06
JPH09511759A (ja)	1997-11-25
DE69519995D1 (en)	2001-03-01
KR100227231B1 (ko)	1999-11-01
AU3868095A (en)	1996-05-23
CZ119897A3 (cs)	1998-03-18
EP0788496A1 (de)	1997-08-13
CN1068000C (zh)	2001-07-04
BG63694B1 (bg)	2002-09-30
EP0788496B1 (de)	2001-01-24
LU91306I2 (fr)	2007-03-19
PT788496E (pt)	2001-07-31
ATE198889T1 (de)	2001-02-15
NZ295353A (en)	1998-08-26
TR199501295A2 (tr)	1996-06-21
DE122007000005I1 (de)	2007-04-26
NO971895L (no)	1997-04-24
FI971784L (fi)	1997-04-25
HRP950532B1 (en)	2001-06-30
IL115771A (en)	2000-02-29
DE122007000005I2 (de)	2008-04-24
HRP950532A2 (en)	1997-08-31
CZ286476B6 (en)	2000-04-12
DE69519995T2 (de)	2001-08-23
AP9700968A0 (en)	1997-04-30
AP779A (en)	1999-11-03
NO971895D0 (no)	1997-04-24
GR3035519T3 (en)	2001-06-29
RO118715B1 (ro)	2003-09-30
ES2155535T3 (es)	2001-05-16
WO1996013499A1 (en)	1996-05-09
US5929075A (en)	1999-07-27
CN1161695A (zh)	1997-10-08
AU697744B2 (en)	1998-10-15
CY2256B1 (en)	2003-07-04
BG101402A (en)	1997-10-31
SK50797A3 (en)	1998-04-08
IL115771A0 (en)	1996-01-19
SK281908B6 (sk)	2001-09-11

Publication	Publication Date	Title
OA10479A (en)	2002-04-09	Apolipoprotein-b synthesis inhibitors
US5521186A (en)	1996-05-28	Apolipoprotein-β synthesis inhibitors
CZ284318B6 (cs)	1998-10-14	Triazolové deriváty, způsob jejich přípravy a použití a meziprodukty tohoto postupu
HK1044762B (en)	2004-01-21	Oxazole and thiazole derivatives as neurotrophin production/secretion promoting agent
JPH10506652A (ja)	1998-06-30	トリアゾール系抗真菌薬
EP0871626B1 (de)	2001-11-07	Triazolone als apolipoprotein-b synthese ihibitoren
JP3415865B2 (ja)	2003-06-09	光学活性アゾール化合物およびその用途
MXPA97003074A (en)	1997-12-01	Synthesis of apoliprotein synthesis
HK1012186B (en)	2002-02-22	Triazolones as apolipoprotein-b synthesis inhibitors