NO890521L - Substituerte pyrimidiner. - Google Patents

Substituerte pyrimidiner.

Info

Publication number: NO890521L
Authority: NO; Norway
Prior art keywords: substituted; aryl; formula; trifluoromethyl; alkyl
Prior art date: 1988-02-25

Application number

NO89890521A

Other languages

English (en)

Norwegian (no)

Other versions

NO890521D0 (no

Inventor

Peter Fey

Rolf Angerbauer

Walter Huebsch

Hilmar Bischoff

Dieter Petzinna

Delf Schmidt

Guenter Thomas

Original Assignee

Bayer Ag

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.)

1988-02-25

Filing date

1989-02-08

Publication date

1989-08-28

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25865194&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO890521(L) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-02-25 Priority claimed from DE3805913A external-priority patent/DE3805913A1/de

1988-11-24 Priority claimed from IT8822721A external-priority patent/IT1227543B/it

1989-02-08 Application filed by Bayer Ag filed Critical Bayer Ag

1989-02-08 Publication of NO890521D0 publication Critical patent/NO890521D0/no

1989-08-28 Publication of NO890521L publication Critical patent/NO890521L/no

Links

150000003230 pyrimidines Chemical class 0.000 title claims description 23
238000002360 preparation method Methods 0.000 claims abstract description 11
-1 dialkylsulfamoyl Chemical group 0.000 claims description 170
125000000217 alkyl group Chemical group 0.000 claims description 81
125000003118 aryl group Chemical group 0.000 claims description 81
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 71
125000003545 alkoxy group Chemical group 0.000 claims description 65
125000004414 alkyl thio group Chemical group 0.000 claims description 59
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 58
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 56
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 46
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000004093 cyano group Chemical group *C#N 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 41
150000002367 halogens Chemical group 0.000 claims description 41
125000005110 aryl thio group Chemical group 0.000 claims description 39
125000004104 aryloxy group Chemical group 0.000 claims description 39
125000001072 heteroaryl group Chemical group 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000003710 aryl alkyl group Chemical group 0.000 claims description 36
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 36
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
239000000460 chlorine Chemical group 0.000 claims description 34
229910052801 chlorine Inorganic materials 0.000 claims description 34
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 34
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 32
229910052731 fluorine Inorganic materials 0.000 claims description 30
239000011737 fluorine Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 28
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
229910052794 bromium Inorganic materials 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 21
125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 21
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 20
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 17
125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 16
150000001299 aldehydes Chemical class 0.000 claims description 16
125000001153 fluoro group Chemical group F* 0.000 claims description 15
125000002541 furyl group Chemical group 0.000 claims description 15
125000005956 isoquinolyl group Chemical group 0.000 claims description 15
125000005493 quinolyl group Chemical group 0.000 claims description 15
125000001544 thienyl group Chemical group 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 14
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 13
150000002596 lactones Chemical class 0.000 claims description 13
125000003373 pyrazinyl group Chemical group 0.000 claims description 13
125000002098 pyridazinyl group Chemical group 0.000 claims description 13
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 11
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 11
150000002576 ketones Chemical class 0.000 claims description 11
125000002971 oxazolyl group Chemical group 0.000 claims description 11
239000011734 sodium Substances 0.000 claims description 11
125000000335 thiazolyl group Chemical group 0.000 claims description 11
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 claims description 10
239000002253 acid Substances 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
125000001041 indolyl group Chemical group 0.000 claims description 9
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
150000001735 carboxylic acids Chemical class 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000001786 isothiazolyl group Chemical group 0.000 claims description 7
125000000842 isoxazolyl group Chemical group 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
239000012312 sodium hydride Substances 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 5
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
MUMHLNVTWIKASW-UHFFFAOYSA-N benzyl hypofluorite Chemical compound FOCC1=CC=CC=C1 MUMHLNVTWIKASW-UHFFFAOYSA-N 0.000 claims 1
150000004677 hydrates Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 45
230000000694 effects Effects 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000005160 1H NMR spectroscopy Methods 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000002904 solvent Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 12
150000002430 hydrocarbons Chemical group 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
235000015424 sodium Nutrition 0.000 description 9
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 8
150000002170 ethers Chemical class 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
238000007127 saponification reaction Methods 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000003513 alkali Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
238000006798 ring closing metathesis reaction Methods 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
239000008096 xylene Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000037396 body weight Effects 0.000 description 4
150000001718 carbodiimides Chemical class 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
150000002168 ethanoic acid esters Chemical class 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052987 metal hydride Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 3
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 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
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 3
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 3
150000004681 metal hydrides Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
XRQAZXMSTPXVCD-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=NC1C1=CC=C(F)C=C1 XRQAZXMSTPXVCD-UHFFFAOYSA-N 0.000 description 1
ILJPHPVLMYMDTN-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-2,6-dimethylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)N=C1C1=CC=C(F)C=C1 ILJPHPVLMYMDTN-UHFFFAOYSA-N 0.000 description 1
PKYAJIKGVYYYLK-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-2-phenyl-6-propan-2-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(C)C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(F)C=C1 PKYAJIKGVYYYLK-UHFFFAOYSA-N 0.000 description 1
DVVAGJCGTFTZJN-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-6-methyl-2-phenyl-1,4-dihydropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)NC1C1=CC=C(F)C=C1 DVVAGJCGTFTZJN-UHFFFAOYSA-N 0.000 description 1
RKAAEZSKIBVVGC-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(F)C=C1 RKAAEZSKIBVVGC-UHFFFAOYSA-N 0.000 description 1
XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000004362 fungal culture Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
HZRMTWQRDMYLNW-UHFFFAOYSA-N lithium metaborate Chemical compound [Li+].[O-]B=O HZRMTWQRDMYLNW-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
ORVKLMUCEUFGET-BUHFOSPRSA-N methyl (e)-7-[4-(4-fluorophenyl)-2-phenyl-6-propan-2-ylpyrimidin-5-yl]-5-hydroxy-3-oxohept-6-enoate Chemical compound COC(=O)CC(=O)CC(O)\C=C\C1=C(C(C)C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(F)C=C1 ORVKLMUCEUFGET-BUHFOSPRSA-N 0.000 description 1
LAMGLADUERXMPQ-OUKQBFOZSA-N methyl (e)-7-[4-(4-fluorophenyl)-6-methyl-2-phenylpyrimidin-5-yl]-5-hydroxy-3-oxohept-6-enoate Chemical compound COC(=O)CC(=O)CC(O)\C=C\C1=C(C)N=C(C=2C=CC=CC=2)N=C1C1=CC=C(F)C=C1 LAMGLADUERXMPQ-OUKQBFOZSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
GCOCYGLSBKOTBU-ZHACJKMWSA-N n-[(e)-2-diethoxyphosphorylethenyl]cyclohexanamine Chemical compound CCOP(=O)(OCC)\C=C\NC1CCCCC1 GCOCYGLSBKOTBU-ZHACJKMWSA-N 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
125000004673 propylcarbonyl group Chemical group 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO89890521A 1988-02-25 1989-02-08 Substituerte pyrimidiner. NO890521L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3805913A DE3805913A1 (de)	1988-02-25	1988-02-25	Substituierte pyrimidine
IT8822721A IT1227543B (it)	1988-11-24	1988-11-24	Pirimidine sostituite.

Publications (2)

Publication Number	Publication Date
NO890521D0 NO890521D0 (no)	1989-02-08
NO890521L true NO890521L (no)	1989-08-28

Family

ID=25865194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO89890521A NO890521L (no)	1988-02-25	1989-02-08	Substituerte pyrimidiner.

Country Status (9)

Country	Link
EP (1)	EP0330057A2 (pt)
JP (1)	JPH01261377A (pt)
CN (1)	CN1036954A (pt)
AU (1)	AU3020289A (pt)
DK (1)	DK88989D0 (pt)
FI (1)	FI890868A7 (pt)
IL (1)	IL89376A0 (pt)
NO (1)	NO890521L (pt)
PT (1)	PT89809A (pt)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT87929B (pt) *	1987-07-10	1995-03-01	Hoechst Ag	Processo para a preparacao de derivados de acido 3-desmetil-mevalonico e de composicoes farmaceuticas que os contem
DE3826814A1 (de) *	1988-08-06	1990-02-08	Hoechst Ag	Neue 6-fluor-3,5-dihydroxycarbonsaeuren und deren derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte
DE3832570A1 (de) *	1988-09-24	1990-03-29	Hoechst Ag	7-substituierte derivate der 3,5-dihydroxyhept-6-insaeure, verfahren zur ihrer herstellung, ihre verwendung als arzneimittel, sowie zwischenprodukte
JP2648897B2 (ja)	1991-07-01	1997-09-03	塩野義製薬株式会社	ピリミジン誘導体
EP0705837B1 (en)	1994-09-06	2002-08-07	Ube Industries, Ltd.	Preparation of 3-Oxy-5-oxo-6-heptenoic acid derivatives
AR008789A1 (es)	1996-07-31	2000-02-23	Bayer Corp	Piridinas y bifenilos substituidos
GB0001621D0 (en)	2000-01-26	2000-03-15	Astrazeneca Ab	Pharmaceutical compositions
TW200614993A (en) *	2004-06-11	2006-05-16	Akzo Nobel Nv	4-phenyl-pyrimidine-2-carbonitrile derivatives
US8372877B2 (en)	2010-04-16	2013-02-12	Cumberland Pharmaceuticals	Stabilized statin formulations
EP2626069A4 (en)	2010-10-06	2014-03-19	Univ Tokyo	Prophylactic and/or therapeutic agent against lymphedema
EP3184103A1 (en)	2015-12-21	2017-06-28	Hexal AG	Pharmaceutical composition comprising atorvastatin or a salt thereof

1989
- 1989-02-08 NO NO89890521A patent/NO890521L/no unknown
- 1989-02-15 EP EP89102536A patent/EP0330057A2/de not_active Withdrawn
- 1989-02-22 IL IL89376A patent/IL89376A0/xx unknown
- 1989-02-22 AU AU30202/89A patent/AU3020289A/en not_active Abandoned
- 1989-02-22 JP JP1040462A patent/JPH01261377A/ja active Pending
- 1989-02-23 PT PT89809A patent/PT89809A/pt not_active Application Discontinuation
- 1989-02-23 FI FI890868A patent/FI890868A7/fi not_active Application Discontinuation
- 1989-02-24 DK DK088989A patent/DK88989D0/da unknown
- 1989-02-25 CN CN89101168A patent/CN1036954A/zh active Pending

Also Published As

Publication number	Publication date
DK88989D0 (da)	1989-02-24
FI890868A7 (fi)	1989-08-26
NO890521D0 (no)	1989-02-08
IL89376A0 (en)	1989-09-10
FI890868A0 (fi)	1989-02-23
AU3020289A (en)	1989-08-31
CN1036954A (zh)	1989-11-08
PT89809A (pt)	1989-10-04
EP0330057A2 (de)	1989-08-30
JPH01261377A (ja)	1989-10-18

Publication	Publication Date	Title
KR0132432B1 (ko)	1998-04-17	치환 피리딘
EP0235164B1 (en)	1990-07-25	Imidazole analogs of mevalonolactone and derivatives thereof
KR900001212B1 (ko)	1990-02-28	메바로노락톤 및 그것의 유도체의 헤테로사이클릭 유사체 및 그것의 생산방법 및 약학적인 그것의 용도
IE893987L (en)	1990-06-14	Substituted 2-pyridones and pyrid-2-thiones, processes for¹their preparation and their use in medicaments
CZ290093A3 (en)	1994-08-17	Hexahydronaphthalene ester derivatives, process of their preparation and pharmaceutical preparations in which they are comprised
CA2046734A1 (en)	1992-01-14	Substituted pyrrolo-pyridines pharmaceuticals
NO881411L (no)	1988-10-17	Substituerte pyrroler.
NO890521L (no)	1989-08-28	Substituerte pyrimidiner.
JP2712107B2 (ja)	1998-02-10	二置換ピリジン類
JPH01272584A (ja)	1989-10-31	５―置換１Ｈ―ピラゾロ［３，４―ｂ］ピリジン誘導体、その製法と薬学的組成物
EP0312269B1 (en)	1993-06-16	3,5-dihydroxy-6,8-nonadienoic acids and derivatives as hypocholesterolemic agents
KR900009006B1 (ko)	1990-12-17	메발로락톤의 동족체 및 그것의 유도체의 제조방법
US4829081A (en)	1989-05-09	Analogs of mevalonolactone and derivatives thereof
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