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
150000002170 ethers Chemical class 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
NWWORXYTJRPSMC-QKPAOTATSA-N ethyl 4-[2-[(2r,3r,4r,5s)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 NWWORXYTJRPSMC-QKPAOTATSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
208000006575 hypertriglyceridemia Diseases 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
210000004731 jugular vein Anatomy 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
229960001110 miglitol Drugs 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
229910000105 potassium hydride Inorganic materials 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229960001729 voglibose Drugs 0.000 description 2
239000008096 xylene Substances 0.000 description 2
FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 description 1
VCIPQQCYKMORDY-KBYFLBCBSA-N (2r,3r,4s,5s,6r)-2-(hydroxymethyl)-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)N[C@@H]1CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCIPQQCYKMORDY-KBYFLBCBSA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
QJLPWVUZFKETMK-LLVKDONJSA-N (5r)-1,5,7,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid Chemical compound O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1C[C@@H](O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-LLVKDONJSA-N 0.000 description 1
RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 1
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-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
HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
DMJDPMXHMLDKKK-UHFFFAOYSA-N 5,6-dichloroindene-1,3-dione Chemical compound C1=C(Cl)C(Cl)=CC2=C1C(=O)CC2=O DMJDPMXHMLDKKK-UHFFFAOYSA-N 0.000 description 1
FBQZCSALVZRRBN-UHFFFAOYSA-N 7,8-dichloro-4-(2-fluorophenyl)-5-oxo-2-propan-2-ylindeno[1,2-b]pyridine-3-carbaldehyde Chemical compound O=CC=1C(C(C)C)=NC=2C3=CC(Cl)=C(Cl)C=C3C(=O)C=2C=1C1=CC=CC=C1F FBQZCSALVZRRBN-UHFFFAOYSA-N 0.000 description 1
AVGQPAXMRYDVIM-UHFFFAOYSA-N 7,8-dichloro-4-(4-fluorophenyl)-3-(hydroxymethyl)-2-propan-2-yl-5h-indeno[1,2-b]pyridin-5-ol Chemical compound OCC=1C(C(C)C)=NC=2C3=CC(Cl)=C(Cl)C=C3C(O)C=2C=1C1=CC=C(F)C=C1 AVGQPAXMRYDVIM-UHFFFAOYSA-N 0.000 description 1
VESUREDLUKLYKJ-UHFFFAOYSA-N 7,8-dichloro-4-(4-fluorophenyl)-3-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-2-propan-2-yl-5h-indeno[1,2-b]pyridin-5-ol Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(F)C=1C(C(C)C)=NC=2C3=CC(Cl)=C(Cl)C=C3C(O)C=2C=1C1=CC=C(F)C=C1 VESUREDLUKLYKJ-UHFFFAOYSA-N 0.000 description 1
HNOBPDFDCJUHFI-UHFFFAOYSA-N 7,8-dichloro-4-(4-fluorophenyl)-3-[fluoro-[4-(trifluoromethyl)phenyl]methyl]-2-propan-2-ylindeno[1,2-b]pyridin-5-one Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(F)C=1C(C(C)C)=NC=2C3=CC(Cl)=C(Cl)C=C3C(=O)C=2C=1C1=CC=C(F)C=C1 HNOBPDFDCJUHFI-UHFFFAOYSA-N 0.000 description 1
ATXHDYLBAORYAQ-UHFFFAOYSA-N 7,8-dichloro-4-(4-fluorophenyl)-3-[hydroxy-[4-(trifluoromethyl)phenyl]methyl]-2-propan-2-ylindeno[1,2-b]pyridin-5-one Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(O)C=1C(C(C)C)=NC=2C3=CC(Cl)=C(Cl)C=C3C(=O)C=2C=1C1=CC=C(F)C=C1 ATXHDYLBAORYAQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229940122816 Amylase inhibitor Drugs 0.000 description 1
102000018616 Apolipoproteins B Human genes 0.000 description 1
108010027006 Apolipoproteins B Proteins 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
AMMUELMHFFPZTO-UHFFFAOYSA-N C(C)C(CCC[N-]CCCC(CC)(CC)CC)(CC)CC.[Li+] Chemical compound C(C)C(CCC[N-]CCCC(CC)(CC)CC)(CC)CC.[Li+] AMMUELMHFFPZTO-UHFFFAOYSA-N 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
108010028554 LDL Cholesterol Proteins 0.000 description 1
238000008214 LDL Cholesterol Methods 0.000 description 1
108010007622 LDL Lipoproteins Proteins 0.000 description 1
208000017170 Lipid metabolism disease Diseases 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
VCIPQQCYKMORDY-UHFFFAOYSA-N MDL 25637 Natural products OC1C(O)C(O)C(CO)NC1COC1C(O)C(O)C(O)C(CO)O1 VCIPQQCYKMORDY-UHFFFAOYSA-N 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QJLPWVUZFKETMK-UHFFFAOYSA-N Pradimicin Q Natural products O=C1C2=C(O)C=C(O)C=C2C(=O)C2=C1C(O)=C1CC(O)C(C=C(C(=C3O)C(O)=O)C)=C3C1=C2O QJLPWVUZFKETMK-UHFFFAOYSA-N 0.000 description 1
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
229910006124 SOCl2 Inorganic materials 0.000 description 1
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
OCTNNXHKAOLDJL-BMGYQPLYSA-N Salbostatin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 OCTNNXHKAOLDJL-BMGYQPLYSA-N 0.000 description 1
OCTNNXHKAOLDJL-UHFFFAOYSA-N Salbostatin Natural products OC1C(O)C(CO)OCC1NC1C(O)C(O)C(O)C(CO)=C1 OCTNNXHKAOLDJL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229930186167 Trestatin Natural products 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 1
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
101800000422 Vastatin Proteins 0.000 description 1
102400001190 Vastatin Human genes 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000009471 action Effects 0.000 description 1
COAIBTZEXXESAS-TZSLYBJXSA-N adiposin Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 COAIBTZEXXESAS-TZSLYBJXSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229960005370 atorvastatin Drugs 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229950001261 camiglibose Drugs 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000001085 differential centrifugation Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
201000005577 familial hyperlipidemia Diseases 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
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)
Animal Behavior & Ethology (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)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Other In-Based Heterocyclic Compounds (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 (es)
EP (1)	EP0825185A1 (es)
JP (1)	JPH1067751A (es)
KR (1)	KR980009247A (es)
CN (1)	CN1172803A (es)
AR (1)	AR007716A1 (es)
AU (1)	AU722365B2 (es)
BG (1)	BG61972B1 (es)
BR (1)	BR9703886A (es)
CA (1)	CA2209609A1 (es)
CO (1)	CO4870759A1 (es)
CZ (1)	CZ214797A3 (es)
DE (1)	DE19627430A1 (es)
EE (1)	EE9700151A (es)
HN (1)	HN1997000082A (es)
HR (1)	HRP970331A2 (es)
HU (1)	HUP9701158A1 (es)
ID (1)	ID17659A (es)
IL (1)	IL121235A0 (es)
MA (1)	MA24261A1 (es)
NO (1)	NO308738B1 (es)
NZ (1)	NZ328260A (es)
PE (1)	PE87798A1 (es)
PL (1)	PL320954A1 (es)
SG (1)	SG46782A1 (es)
SK (1)	SK92697A3 (es)
TN (1)	TNSN97116A1 (es)
TR (1)	TR199700583A2 (es)
YU (1)	YU28897A (es)
ZA (1)	ZA976021B (es)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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
WO2000038727A1 (en)	1998-12-23	2000-07-06	G.D. Searle Llc	Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications
PT1140185E (pt)	1998-12-23	2003-10-31	Searle Llc	Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com agentes sequestrantes de acido biliar para indicacoes cardiovasculares
PL348503A1 (en)	1998-12-23	2002-05-20	Searle Llc	Combinations of cholesteryl ester transfer protein inhibitors and fibric acid derivatives for cardiovascular indications
PT1140190E (pt)	1998-12-23	2003-02-28	Searle Llc	Combinacoes de inibidores do transporte ileal dos acidos biliares e agentes sequestrantes dos acidos biliares usadas para problemas cardiovasculares
AU2157400A (en)	1998-12-23	2000-07-31	G.D. Searle & Co.	Combinations of cholesteryl ester transfer protein inhibitors and hmg coa reductase inhibitors for cardiovascular indications
JP2002533412A (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コレステリルエステル転送タンパク質阻害剤の組み合わせ
WO2000038721A1 (en)	1998-12-23	2000-07-06	G.D. Searle Llc	Combinations of cholesteryl ester transfer protein inhibitors and nicotinic acid derivatives for cardiovascular indications
US6924313B1 (en)	1999-09-23	2005-08-02	Pfizer Inc.	Substituted tertiary-heteroalkylamines 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
US6683113B2 (en) *	1999-09-23	2004-01-27	Pharmacia Corporation	(R)-chiral halogenated substituted N,N-Bis-benzyl aminioalcohol compounds useful for inhibiting cholesteryl ester transfer protein activity
US6586434B2 (en)	2000-03-10	2003-07-01	G.D. Searle, Llc	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
US20050239782A1 (en) *	2001-04-18	2005-10-27	Heintzelman Geoffrey R	Arylindenopyridines and related therapeutic and prophylactic methods
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
OA12625A (en)	2001-06-22	2006-06-12	Pfizer Prod Inc	Pharmaceutical compositions of adsorbates of amorphous drug.
JP2004534812A (ja)	2001-06-22	2004-11-18	ファイザー・プロダクツ・インク	薬物および中性ポリマーの分散物の医薬組成物
BR0213501A (pt)	2001-11-02	2004-08-24	Searle Llc	Compostos de benzotiepina mono- e di-fluorada como inibidores de transporte de ácido biliar co-dependente de sódio apical (asbt) e captação de taurocolato
US6852753B2 (en)	2002-01-17	2005-02-08	Pharmacia Corporation	Alkyl/aryl hydroxy or keto thiepine compounds as inhibitors of apical sodium co-dependent bile acid transport (ASBT) and taurocholate uptake
DE60320940D1 (de)	2002-02-01	2008-06-26	Pfizer Prod Inc	Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien
US20040127510A1 (en)	2002-04-16	2004-07-01	Heintzelman Geoffrey R.	Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
BRPI0413277A (pt)	2003-08-04	2006-10-10	Pfizer Prod Inc	composições farmacêuticas de adsorvatos de medicamentos amorfos e materiais que formam microfases lipofìlicas
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.
MXPA06003357A (es) *	2003-09-26	2006-06-08	Japan Tobacco Inc	Metodo para inhibir la produccion de lipoproteina remanente.
DE602004023100D1 (de)	2003-10-08	2009-10-22	Lilly Co Eli	Verbindungen und verfahren zur behandlung von dyslipidemie
JP2007530550A (ja)	2004-03-26	2007-11-01	イーライリリーアンドカンパニー	異脂肪血症を治療するための化合物および方法
ES2384980T3 (es) *	2004-12-18	2012-07-16	Bayer Pharma Aktiengesellschaft	Derivados de tetrahidroquinolina sustituidos en 4 con cicloalquilo y su uso como medicamentos
WO2006082518A1 (en)	2005-02-03	2006-08-10	Pfizer Products Inc.	Pharmaceutical compositions with enhanced performance
JP2009512715A (ja)	2005-10-21	2009-03-26	ノバルティスアクチエンゲゼルシャフト	レニン阻害剤と抗異脂肪血症剤および／または抗肥満症剤の組み合わせ
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
WO2012027331A1 (en)	2010-08-27	2012-03-01	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 BG BG101746A patent/BG61972B1/bg unknown
- 1997-07-04 PL PL97320954A patent/PL320954A1/xx unknown
- 1997-07-04 ID IDP972332A patent/ID17659A/id unknown
- 1997-07-04 NZ NZ328260A patent/NZ328260A/en unknown
- 1997-07-04 IL IL12123597A patent/IL121235A0/xx unknown
- 1997-07-04 CA CA002209609A patent/CA2209609A1/en not_active Abandoned
- 1997-07-04 TR TR97/00583A patent/TR199700583A2/xx unknown
- 1997-07-07 NO NO973144A patent/NO308738B1/no not_active IP Right Cessation
- 1997-07-07 KR KR1019970031342A patent/KR980009247A/ko not_active Withdrawn
- 1997-07-07 HU HU9701158A patent/HUP9701158A1/hu unknown
- 1997-07-07 TN TNTNSN97116A patent/TNSN97116A1/fr unknown
- 1997-07-07 CZ CZ972147A patent/CZ214797A3/cs unknown
- 1997-07-07 CO CO97037764A patent/CO4870759A1/es unknown
- 1997-07-07 JP JP9195235A patent/JPH1067751A/ja active Pending
- 1997-07-07 MA MA24705A patent/MA24261A1/fr unknown
- 1997-07-07 ZA ZA9706021A patent/ZA976021B/xx unknown
- 1997-07-07 SK SK926-97A patent/SK92697A3/sk unknown
- 1997-07-07 PE PE1997000581A patent/PE87798A1/es not_active Application Discontinuation
- 1997-07-08 BR BR9703886A patent/BR9703886A/pt active Search and Examination
- 1997-07-08 EE EE9700151A patent/EE9700151A/xx unknown
- 1997-07-08 YU YU28897A patent/YU28897A/sh unknown
- 1997-07-08 CN CN97114558A patent/CN1172803A/zh active Pending

Also Published As

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

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
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
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
US6121330A (en)	2000-09-19	5-Hydroxyalkyl substituted phenyls and their use in medicaments for the treatment of arteriosclerosis and hyperlipoproteinaemia
AU730109B2 (en)	2001-02-22	2-amino-substituted pyridines which can be used for the treatment of arteriosclerosis and hyperclipoproteinaemia
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
IE911553A1 (en)	1991-11-20	Azabenzimidazoles in the treatment of asthma, arthritis and¹related diseases
MXPA97005093A (es)	1998-01-01	Piridinas condensadas biciclicas
MXPA97005084A (es)	1998-01-01	Piridinas condensadas con heterociclos,procedimiento para su produccion y su uso enmedicamentos
MXPA97002042A (es)	1998-07-03	Piridinas sustituidas por 2-arilo
MXPA99007244A (es)	2000-01-01	Piridinas 2-amino sustituidas para su uso en eltratamiento de la arteriosclerosis e hiperlipoproteinemia
IL139706A (en)	2001-05-20	3-amino-3-cyclopentyl-1-(4-trifluoromethyl phenyl)-propenone and its derivatives