HRP970331A2 - Pyridine fused to a bicyclic ring - Google Patents

Pyridine fused to a bicyclic ring

Info

Publication number: HRP970331A2
Authority: HR; Croatia
Prior art keywords: chain; carbon atoms; straight; substituted; branched alkyl
Prior art date: 1996-07-08

Application number

HR19627430.3A

Other languages

English (en)

Croatian (hr)

Inventor

Joachim Schuhmacher

Original Assignee

Joachim Schuhmacher

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.)

1996-07-08

Filing date

1997-06-17

Publication date

1998-08-31

1997-06-17 Application filed by Joachim Schuhmacher filed Critical Joachim Schuhmacher

1998-08-31 Publication of HRP970331A2 publication Critical patent/HRP970331A2/hr

Links

JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 12
125000002619 bicyclic group Chemical group 0.000 title claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 68
125000000217 alkyl group Chemical group 0.000 claims description 38
150000001875 compounds Chemical class 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 23
229910052801 chlorine Inorganic materials 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 21
239000011737 fluorine Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
-1 tetrahydronaphthalenyl Chemical group 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 10
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 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
150000003222 pyridines Chemical class 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000001041 indolyl group Chemical group 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 4
208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims description 4
208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
238000007239 Wittig reaction Methods 0.000 claims description 3
238000007796 conventional method Methods 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
208000020346 hyperlipoproteinemia Diseases 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000002524 organometallic group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
238000003747 Grignard reaction Methods 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
229910052804 chromium Inorganic materials 0.000 claims 1
239000011651 chromium Chemical group 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
238000012360 testing method Methods 0.000 description 22
239000000243 solution Substances 0.000 description 20
102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 16
108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 16
239000000126 substance Substances 0.000 description 16
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000203 mixture Substances 0.000 description 9
210000002966 serum Anatomy 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
230000009467 reduction Effects 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
239000000523 sample Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
235000012000 cholesterol Nutrition 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
239000012071 phase Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
108090001030 Lipoproteins Proteins 0.000 description 4
102000004895 Lipoproteins Human genes 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
238000011534 incubation Methods 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
238000012546 transfer Methods 0.000 description 4
150000003626 triacylglycerols Chemical class 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
108010010234 HDL Lipoproteins Proteins 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000011324 bead Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052987 metal hydride Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000009747 swallowing Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010053567 Coagulopathies Diseases 0.000 description 2
208000031288 Combined hyperlipidaemia Diseases 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
208000032928 Dyslipidaemia Diseases 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
108010023302 HDL Cholesterol Proteins 0.000 description 2
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 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000699673 Mesocricetus auratus Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
229920002684 Sepharose Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 2
229960002632 acarbose Drugs 0.000 description 2
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003392 amylase inhibitor Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
238000009395 breeding Methods 0.000 description 2
230000001488 breeding effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229950005499 carbon tetrachloride Drugs 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
229960005110 cerivastatin Drugs 0.000 description 2
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
230000035602 clotting Effects 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229950000269 emiglitate Drugs 0.000 description 2
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VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
FMUJIJVVYZXXIU-UHFFFAOYSA-N lithium;trifluoromethylbenzene Chemical compound [Li+].FC(F)(F)C1=CC=[C-]C=C1 FMUJIJVVYZXXIU-UHFFFAOYSA-N 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QBZUNIPJVKAQQC-XQRVVYSFSA-N methyl (z)-3-amino-4-methylpent-2-enoate Chemical compound COC(=O)\C=C(/N)C(C)C QBZUNIPJVKAQQC-XQRVVYSFSA-N 0.000 description 1
LXENPZUQYDSBJW-UHFFFAOYSA-N methyl 7,8-dichloro-4-(4-fluorophenyl)-5-oxo-2-propan-2-ylindeno[1,2-b]pyridine-3-carboxylate Chemical compound COC(=O)C1=C(C(C)C)N=C2C3=CC(Cl)=C(Cl)C=C3C(=O)C2=C1C1=CC=C(F)C=C1 LXENPZUQYDSBJW-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000902 placebo Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
230000009862 primary prevention Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012465 retentate Substances 0.000 description 1
230000004141 reverse cholesterol transport Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000009863 secondary prevention Effects 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229950001790 tendamistat Drugs 0.000 description 1
108010037401 tendamistate Proteins 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
RIUWBIIVUYSTCN-UHFFFAOYSA-N trilithium borate Chemical compound [Li+].[Li+].[Li+].[O-]B([O-])[O-] RIUWBIIVUYSTCN-UHFFFAOYSA-N 0.000 description 1
GGAUJFNZKFHHGA-UHFFFAOYSA-M triphenyl-[[3-(trifluoromethyl)phenyl]methyl]phosphanium;bromide Chemical compound [Br-].FC(F)(F)C1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GGAUJFNZKFHHGA-UHFFFAOYSA-M 0.000 description 1
WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
- 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
- A61P9/10—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

HR19627430.3A 1996-07-08 1997-06-17 Pyridine fused to a bicyclic ring HRP970331A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19627430A DE19627430A1 (de)	1996-07-08	1996-07-08	Bicyclisch kondensierte Pyridine

Publications (1)

Publication Number	Publication Date
HRP970331A2 true HRP970331A2 (en)	1998-08-31

Family

ID=7799218

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR19627430.3A HRP970331A2 (en)	1996-07-08	1997-06-17	Pyridine fused to a bicyclic ring

Country Status (30)

Country	Link
US (1)	US6063788A (xx)
EP (1)	EP0825185A1 (xx)
JP (1)	JPH1067751A (xx)
KR (1)	KR980009247A (xx)
CN (1)	CN1172803A (xx)
AR (1)	AR007716A1 (xx)
AU (1)	AU722365B2 (xx)
BG (1)	BG61972B1 (xx)
BR (1)	BR9703886A (xx)
CA (1)	CA2209609A1 (xx)
CO (1)	CO4870759A1 (xx)
CZ (1)	CZ214797A3 (xx)
DE (1)	DE19627430A1 (xx)
EE (1)	EE9700151A (xx)
HN (1)	HN1997000082A (xx)
HR (1)	HRP970331A2 (xx)
HU (1)	HUP9701158A1 (xx)
ID (1)	ID17659A (xx)
IL (1)	IL121235A0 (xx)
MA (1)	MA24261A1 (xx)
NO (1)	NO308738B1 (xx)
NZ (1)	NZ328260A (xx)
PE (1)	PE87798A1 (xx)
PL (1)	PL320954A1 (xx)
SG (1)	SG46782A1 (xx)
SK (1)	SK92697A3 (xx)
TN (1)	TNSN97116A1 (xx)
TR (1)	TR199700583A2 (xx)
YU (1)	YU28897A (xx)
ZA (1)	ZA976021B (xx)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6642268B2 (en)	1994-09-13	2003-11-04	G.D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors
US6268392B1 (en)	1994-09-13	2001-07-31	G. D. Searle & Co.	Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors
US6262277B1 (en)	1994-09-13	2001-07-17	G.D. Searle And Company	Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
AU776664B2 (en)	1998-12-23	2004-09-16	G.D. Searle Llc	Combinations of cholesteryl ester transfer protein inhibitors and fibric acid derivatives for cardiovascular indications
ES2203239T3 (es)	1998-12-23	2004-04-01	G.D. Searle Llc	Combinaciones de inhibidores de la proteina de transferencia de ester de colesterilo y de agentes secuestrantes de acidos biliares para indicaciones cardiovasculares.
US6462091B1 (en)	1998-12-23	2002-10-08	G.D. Searle & Co.	Combinations of cholesteryl ester transfer protein inhibitors and HMG coA reductase inhibitors for cardiovascular indications
JP2002533414A (ja)	1998-12-23	2002-10-08	ジー．ディー．サールエルエルシー	心臓血管に適用するための回腸胆汁酸輸送阻害剤および胆汁酸隔離剤の組み合わせ
US6489366B1 (en)	1998-12-23	2002-12-03	G. D. Searle, Llc	Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications
NZ512536A (en)	1998-12-23	2003-11-28	G	Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications
IL143947A0 (en)	1998-12-23	2002-04-21	Searle Llc	Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications
US6521607B1 (en) *	1999-09-23	2003-02-18	Pharmacia Corporation	(R)-chiral halogenated substituted N-phenoxy N-phenyl aminoalcohol compounds useful for inhibiting cholesteryl ester transfer protein activity
US20010018446A1 (en)	1999-09-23	2001-08-30	G.D. Searle & Co.	Substituted N-Aliphatic-N-Aromatictertiary-Heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
US6924313B1 (en)	1999-09-23	2005-08-02	Pfizer Inc.	Substituted tertiary-heteroalkylamines useful for inhibiting cholesteryl ester transfer protein activity
US6794544B2 (en)	2000-03-10	2004-09-21	Pharmacia Corporation	Method for the preparation of tetrahydrobenzothiepines
US20040219619A1 (en) *	2000-07-21	2004-11-04	Ester Fernandez-Salas	Methods of identifying compounds that alter toxin persistence and/or protease activity
US6958328B2 (en) *	2001-04-18	2005-10-25	Ortho-Mcneil Pharmaceutical, Inc	Arylindenopyridines and related therapeutic and prophylactic methods
US6903109B2 (en)	2001-04-18	2005-06-07	Ortho-Muniel Pharmaceutical, Inc.	Arylindenopyridines and related therapeutic and prophylactic methods
US20050239782A1 (en) *	2001-04-18	2005-10-27	Heintzelman Geoffrey R	Arylindenopyridines and related therapeutic and prophylactic methods
CA2450957A1 (en)	2001-06-22	2003-01-03	Pfizer Products Inc.	Pharmaceutical compositions of dispersions of drugs and neutral polymers
WO2003000238A1 (en)	2001-06-22	2003-01-03	Pfizer Products Inc.	Pharmaceutical compositions of adsorbates of amorphous drug
JP2005518347A (ja)	2001-11-02	2005-06-23	ジー．ディー．サールエルエルシー	頂端ナトリウム共依存性胆汁酸輸送（ａｓｂｔ）およびタウロコール酸塩取り込みの阻害剤としての新規一および二フッ化ベンゾチエピン化合物
MXPA04006255A (es)	2002-01-17	2004-09-27	Pharmacia Corp	Compuestos novedosos de alquil/aril hidroxi o ceto tiepina como inhibidores del transporte del acido biliar codependiente del sodio apical y la captacion de taurocolato.
JP2005523262A (ja) *	2002-02-01	2005-08-04	ファイザー・プロダクツ・インク	薬物及び親油性ミクロ相形成物質の非晶質分散物の医薬組成物
US20040127510A1 (en)	2002-04-16	2004-07-01	Heintzelman Geoffrey R.	Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
CL2004001884A1 (es)	2003-08-04	2005-06-03	Pfizer Prod Inc	Procedimiento de secado por pulverizacion para la formacion de dispersiones solidas amorfas de un farmaco y polimeros.
JP2007501218A (ja)	2003-08-04	2007-01-25	ファイザー・プロダクツ・インク	非晶質薬物の吸着物および親油性ミクロ相形成物質の医薬組成物
SG146695A1 (en)	2003-09-26	2008-10-30	Japan Tobacco Inc	Method of inhibiting remnant lipoprotein production
JP4773969B2 (ja)	2003-10-08	2011-09-14	イーライリリーアンドカンパニー	脂質代謝異常の治療ための化合物及び方法
DK1732933T3 (da)	2004-03-26	2008-10-27	Lilly Co Eli	Forobindelser til behandling af dyslipidæmi
EP1828137B1 (de) *	2004-12-18	2012-04-25	Bayer Pharma Aktiengesellschaft	4-cycloalkyl-substituierte tetrahydrochinolinderivate und deren verwendung als medikamente
WO2006082518A1 (en)	2005-02-03	2006-08-10	Pfizer Products Inc.	Pharmaceutical compositions with enhanced performance
BRPI0617621A2 (pt)	2005-10-21	2011-08-02	Novartis Ag	combinação de compostos orgánicos
DE102006012548A1 (de) *	2006-03-18	2007-09-20	Bayer Healthcare Ag	Substituierte Chromanol-Derivate und ihre Verwendung
PA8801401A1 (es) *	2007-10-25	2009-05-15	Janssen Pharmaceutica Nv	Arilindenopirimidinas y su uso como adenosina a2a
US20130156720A1 (en)	2010-08-27	2013-06-20	Ironwood Pharmaceuticals, Inc.	Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5169857A (en) *	1988-01-20	1992-12-08	Bayer Aktiengesellschaft	7-(polysubstituted pyridyl)-hept-6-endates useful for treating hyperproteinaemia, lipoproteinaemia or arteriosclerosis
GB8626344D0 (en) *	1986-11-04	1986-12-03	Zyma Sa	Bicyclic compounds
NO177005C (no) *	1988-01-20	1995-07-05	Bayer Ag	Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen
IE892088L (en) *	1988-07-12	1990-01-12	William Henry Deryk Morris	Quinoline derivatives, their production and use
ZA911046B (en) *	1990-02-26	1992-10-28	Squibb & Sons Inc	Quinoline and pyridine anchors for hmg-coa reductase inhibitors
JPH059179A (ja) *	1990-09-27	1993-01-19	Takeda Chem Ind Ltd	複素環化合物、その製造法及びａｃａｔ阻害剤

1996
- 1996-07-08 DE DE19627430A patent/DE19627430A1/de not_active Withdrawn
1997
- 1997-06-16 HN HN1997000082A patent/HN1997000082A/es unknown
- 1997-06-17 HR HR19627430.3A patent/HRP970331A2/hr not_active Application Discontinuation
- 1997-06-18 SG SG1997002082A patent/SG46782A1/en unknown
- 1997-06-25 EP EP97110360A patent/EP0825185A1/de not_active Withdrawn
- 1997-06-27 US US08/883,067 patent/US6063788A/en not_active Expired - Fee Related
- 1997-07-02 AR ARP970102972A patent/AR007716A1/es not_active Application Discontinuation
- 1997-07-03 AU AU28448/97A patent/AU722365B2/en not_active Ceased
- 1997-07-04 ID IDP972332A patent/ID17659A/id unknown
- 1997-07-04 IL IL12123597A patent/IL121235A0/xx unknown
- 1997-07-04 CA CA002209609A patent/CA2209609A1/en not_active Abandoned
- 1997-07-04 PL PL97320954A patent/PL320954A1/xx unknown
- 1997-07-04 BG BG101746A patent/BG61972B1/bg unknown
- 1997-07-04 TR TR97/00583A patent/TR199700583A2/xx unknown
- 1997-07-04 NZ NZ328260A patent/NZ328260A/en unknown
- 1997-07-07 HU HU9701158A patent/HUP9701158A1/hu unknown
- 1997-07-07 PE PE1997000581A patent/PE87798A1/es not_active Application Discontinuation
- 1997-07-07 JP JP9195235A patent/JPH1067751A/ja active Pending
- 1997-07-07 SK SK926-97A patent/SK92697A3/sk unknown
- 1997-07-07 MA MA24705A patent/MA24261A1/fr unknown
- 1997-07-07 NO NO973144A patent/NO308738B1/no not_active IP Right Cessation
- 1997-07-07 CO CO97037764A patent/CO4870759A1/es unknown
- 1997-07-07 KR KR1019970031342A patent/KR980009247A/ko not_active Application Discontinuation
- 1997-07-07 TN TNTNSN97116A patent/TNSN97116A1/fr unknown
- 1997-07-07 CZ CZ972147A patent/CZ214797A3/cs unknown
- 1997-07-07 ZA ZA9706021A patent/ZA976021B/xx unknown
- 1997-07-08 EE EE9700151A patent/EE9700151A/xx unknown
- 1997-07-08 BR BR9703886A patent/BR9703886A/pt active Search and Examination
- 1997-07-08 CN CN97114558A patent/CN1172803A/zh active Pending
- 1997-07-08 YU YU28897A patent/YU28897A/sh unknown

Also Published As

Publication number	Publication date
HU9701158D0 (en)	1997-09-29
HN1997000082A (es)	1997-12-26
HUP9701158A1 (hu)	1999-09-28
BG101746A (en)	1998-03-31
SK92697A3 (en)	1998-02-04
BR9703886A (pt)	1998-11-03
JPH1067751A (ja)	1998-03-10
YU28897A (xx)	2000-03-21
CO4870759A1 (es)	1999-12-27
EE9700151A (et)	1998-02-16
IL121235A0 (en)	1998-01-04
MA24261A1 (fr)	1998-04-01
SG46782A1 (en)	1998-02-20
NZ328260A (en)	1998-09-24
NO308738B1 (no)	2000-10-23
NO973144D0 (no)	1997-07-07
DE19627430A1 (de)	1998-01-15
TR199700583A2 (xx)	1998-01-21
TNSN97116A1 (fr)	2005-03-15
PE87798A1 (es)	1999-02-13
US6063788A (en)	2000-05-16
ZA976021B (en)	1998-02-02
AU722365B2 (en)	2000-08-03
EP0825185A1 (de)	1998-02-25
AU2844897A (en)	1998-01-15
PL320954A1 (en)	1998-01-19
ID17659A (id)	1998-01-15
NO973144L (no)	1998-01-09
CA2209609A1 (en)	1998-01-08
KR980009247A (ko)	1998-04-30
CZ214797A3 (cs)	1998-01-14
BG61972B1 (bg)	1998-11-30
AR007716A1 (es)	1999-11-10
CN1172803A (zh)	1998-02-11

Legal Events

Date	Code	Title
1998-08-31	A1OB	Publication of a patent application
1998-12-22	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2003-08-30	ODBC	Application rejected

Publication	Publication Date	Title
HRP970331A2 (en)	1998-08-31	Pyridine fused to a bicyclic ring
CA2209825C (en)	2006-02-14	Heterocyclic-fused pyridines
HRP970105A2 (en)	1998-04-30	2-aryl substituted pyridines
US6291477B1 (en)	2001-09-18	Tetrahydroquinolines, processes for their preparation, pharmaceutical compositions containing them, and their use to prevent or treat hyperlipoproteinaemia
CA2209640C (en)	2009-09-22	Cycloalkano-pyridines
US6387929B1 (en)	2002-05-14	4-heteroaryl-tetrahydroquinolines and their use as inhibitors of the cholesterin-ester transfer protein
US6207671B1 (en)	2001-03-27	Cycloalkano-pyridines
OA10970A (en)	2001-11-05	Substituted pyrido- or pyrimido- containing 6,6-or6,7-bicyclic derivatives
JPH0327380A (ja)	1991-02-05	１ｈ―イミダゾ〔４，５―ｃ〕キノリン―４―アミン類
JP2001513790A (ja)	2001-09-04	５−オキシ置換キノリン類およびコレステロールエステル輸送タンパク質阻害剤としてのそれらの使用
US6121330A (en)	2000-09-19	5-Hydroxyalkyl substituted phenyls and their use in medicaments for the treatment of arteriosclerosis and hyperlipoproteinaemia
JP2001517646A (ja)	2001-10-09	ベンジルビフェニルおよび類似化合物、ならびに動脈硬化症および異脂肪血症を治療するためのそれらの適用
AU730109B2 (en)	2001-02-22	2-amino-substituted pyridines which can be used for the treatment of arteriosclerosis and hyperclipoproteinaemia
IE911553A1 (en)	1991-11-20	Azabenzimidazoles in the treatment of asthma, arthritis and¹related diseases
MXPA97005093A (en)	1998-01-01	Bicicli condensed pyridine
MXPA97005084A (en)	1998-01-01	Condensed pyridine with heterocicles, procedure for its production and its use immediately
MXPA97002042A (en)	1998-07-03	Pyridine replaced by 2-ar
IL139706A (en)	2001-05-20	3-amino-3-cyclopentyl-1-(4-trifluoromethyl phenyl)-propenone and its derivatives
MXPA00002771A (en)	2001-06-26	Benzyl-biphenyls and analogous compounds and the application thereof in order to treat arteriosclerosis and dyslipidaemia