DE10130835A1 - Diphenyl-Derivate - Google Patents

Diphenyl-Derivate

Info

Publication number: DE10130835A1
Authority: DE; Germany
Prior art keywords: alkyl; substituted; different; alkoxy; phenyl
Prior art date: 2001-03-12
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE10130835A

Other languages

German (de)

English (en)

Inventor

Helmut Haning

Michael Woltering

Gunter Schmidt

Christiane Faeste

Hilmar Bischoff

Axel Kretschmer

Verena Voehringer

Peter Ellinghaus

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

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.)

2001-03-12

Filing date

2001-06-27

Publication date

2002-09-19

2001-06-27 Application filed by Bayer AG filed Critical Bayer AG

2001-06-27 Priority to DE10130835A priority Critical patent/DE10130835A1/de

2002-02-26 Priority to US10/082,022 priority patent/US6777442B2/en

2002-02-27 Priority to CA002440282A priority patent/CA2440282A1/en

2002-02-27 Priority to EP02719938A priority patent/EP1370523A1/de

2002-02-27 Priority to PCT/EP2002/002065 priority patent/WO2002072539A1/de

2002-03-11 Priority to PE2002000187A priority patent/PE20021044A1/es

2002-03-11 Priority to HN2002000052A priority patent/HN2002000052A/es

2002-09-19 Publication of DE10130835A1 publication Critical patent/DE10130835A1/de

Status Withdrawn legal-status Critical Current

Links

125000006267 biphenyl group Chemical group 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 56
238000000034 method Methods 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 10
208000008589 Obesity Diseases 0.000 claims abstract description 7
235000020824 obesity Nutrition 0.000 claims abstract description 7
239000005495 thyroid hormone Substances 0.000 claims abstract description 6
229940036555 thyroid hormone Drugs 0.000 claims abstract description 6
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 3
206010003210 Arteriosclerosis Diseases 0.000 claims abstract 2
208000011775 arteriosclerosis disease Diseases 0.000 claims abstract 2
-1 cyano, nitro, amino Chemical group 0.000 claims description 119
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 91
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 73
239000001257 hydrogen Substances 0.000 claims description 73
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 70
229910052736 halogen Inorganic materials 0.000 claims description 63
150000002367 halogens Chemical class 0.000 claims description 63
125000000623 heterocyclic group Chemical group 0.000 claims description 57
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 51
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
150000002431 hydrogen Chemical class 0.000 claims description 43
125000005842 heteroatom Chemical group 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 35
239000000460 chlorine Substances 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
229910052731 fluorine Inorganic materials 0.000 claims description 28
125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 26
239000011737 fluorine Substances 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
229910052794 bromium Inorganic materials 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 23
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000004076 pyridyl group Chemical group 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
150000004677 hydrates Chemical class 0.000 claims description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 14
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000012453 solvate Substances 0.000 claims description 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000002098 pyridazinyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000005002 aryl methyl group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
239000000543 intermediate Substances 0.000 claims description 4
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
229940002612 prodrug Drugs 0.000 claims description 3
239000000651 prodrug Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
201000010099 disease Diseases 0.000 claims 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
238000011321 prophylaxis Methods 0.000 claims 3
230000002265 prevention Effects 0.000 claims 1
208000032928 Dyslipidaemia Diseases 0.000 abstract description 2
206010018498 Goitre Diseases 0.000 abstract description 2
208000017170 Lipid metabolism disease Diseases 0.000 abstract description 2
208000024770 Thyroid neoplasm Diseases 0.000 abstract description 2
201000003872 goiter Diseases 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
125000004432 carbon atom Chemical group C* 0.000 description 22
239000000126 substance Substances 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
238000012360 testing method Methods 0.000 description 18
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 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 description 10
241001465754 Metazoa Species 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 8
239000004480 active ingredient Substances 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
QYLZTMMBHDBYME-UHFFFAOYSA-N (3-bromo-4-phenylmethoxyphenyl)methoxy-tert-butyl-dimethylsilane Chemical compound BrC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1OCC1=CC=CC=C1 QYLZTMMBHDBYME-UHFFFAOYSA-N 0.000 description 5
FOWREKVIPOMJSO-UHFFFAOYSA-N (4-bromo-3,5-dimethylphenoxy)-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)OC1=CC(C)=C(Br)C(C)=C1 FOWREKVIPOMJSO-UHFFFAOYSA-N 0.000 description 5
LUVSDKZPRITQQP-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-4-phenylmethoxybenzaldehyde Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 LUVSDKZPRITQQP-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
101001009079 Homo sapiens Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Proteins 0.000 description 5
DPWCSJXMCZKADY-UHFFFAOYSA-N [2,6-dimethyl-4-tri(propan-2-yl)silyloxyphenyl]-[3-(4-fluorophenyl)sulfonyl-4-phenylmethoxyphenyl]methanol Chemical compound CC1=CC(O[Si](C(C)C)(C(C)C)C(C)C)=CC(C)=C1C(O)C(C=C1S(=O)(=O)C=2C=CC(F)=CC=2)=CC=C1OCC1=CC=CC=C1 DPWCSJXMCZKADY-UHFFFAOYSA-N 0.000 description 5
HJURWTMUCFCBQD-UHFFFAOYSA-N [4-[[3-(4-fluorophenyl)sulfonyl-4-phenylmethoxyphenyl]methyl]-3,5-dimethylphenoxy]-tri(propan-2-yl)silane Chemical compound CC1=CC(O[Si](C(C)C)(C(C)C)C(C)C)=CC(C)=C1CC(C=C1S(=O)(=O)C=2C=CC(F)=CC=2)=CC=C1OCC1=CC=CC=C1 HJURWTMUCFCBQD-UHFFFAOYSA-N 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
230000037396 body weight Effects 0.000 description 5
235000012000 cholesterol Nutrition 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
ACMJFTBIXIJITR-UHFFFAOYSA-N 4-[[3-(4-fluorophenyl)sulfonyl-4-phenylmethoxyphenyl]methyl]-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1CC(C=C1S(=O)(=O)C=2C=CC(F)=CC=2)=CC=C1OCC1=CC=CC=C1 ACMJFTBIXIJITR-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
102100027391 Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Human genes 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
230000014509 gene expression Effects 0.000 description 4
108020004999 messenger RNA Proteins 0.000 description 4
239000012071 phase Substances 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
LDXCLIDRDMAUAX-UHFFFAOYSA-N (3-bromo-4-phenylmethoxyphenyl)methanol Chemical compound BrC1=CC(CO)=CC=C1OCC1=CC=CC=C1 LDXCLIDRDMAUAX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
108060001084 Luciferase Proteins 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
NNICBSFHFQGLFX-UHFFFAOYSA-N [3-(4-fluorophenyl)sulfonyl-4-phenylmethoxyphenyl]methanol Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C1=CC(CO)=CC=C1OCC1=CC=CC=C1 NNICBSFHFQGLFX-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
210000004027 cell Anatomy 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
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
230000002526 effect on cardiovascular system Effects 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 2
SSWDPJORPKQDCH-UHFFFAOYSA-N 2-[4-[[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenyl]methyl]-3,5-dimethylphenoxy]acetic acid Chemical compound CC1=CC(OCC(O)=O)=CC(C)=C1CC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 SSWDPJORPKQDCH-UHFFFAOYSA-N 0.000 description 2
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 2
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920001304 Solutol HS 15 Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- 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)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Vascular Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Urology & Nephrology (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE10130835A 2001-03-12 2001-06-27 Diphenyl-Derivate Withdrawn DE10130835A1 (de)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
DE10130835A DE10130835A1 (de)	2001-03-12	2001-06-27	Diphenyl-Derivate
US10/082,022 US6777442B2 (en)	2001-03-12	2002-02-26	Diphenyl derivatives
CA002440282A CA2440282A1 (en)	2001-03-12	2002-02-27	Diphenyl derivatives
EP02719938A EP1370523A1 (de)	2001-03-12	2002-02-27	Diphenyl-derivate
PCT/EP2002/002065 WO2002072539A1 (de)	2001-03-12	2002-02-27	Diphenyl-derivate
PE2002000187A PE20021044A1 (es)	2001-03-12	2002-03-11	Derivados de difenilo
HN2002000052A HN2002000052A (es)	2001-03-12	2002-03-11	Derivados de difenilo

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10111651		2001-03-12
DE10130835A DE10130835A1 (de)	2001-03-12	2001-06-27	Diphenyl-Derivate

Publications (1)

Publication Number	Publication Date
DE10130835A1 true DE10130835A1 (de)	2002-09-19

Family

ID=7677048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE10130835A Withdrawn DE10130835A1 (de)	2001-03-12	2001-06-27	Diphenyl-Derivate

Country Status (4)

Country	Link
DE (1)	DE10130835A1 (es)
GT (1)	GT200200047A (es)
HN (1)	HN2002000052A (es)
PE (1)	PE20021044A1 (es)

2001
- 2001-06-27 DE DE10130835A patent/DE10130835A1/de not_active Withdrawn
2002
- 2002-03-11 GT GT200200047A patent/GT200200047A/es unknown
- 2002-03-11 HN HN2002000052A patent/HN2002000052A/es unknown
- 2002-03-11 PE PE2002000187A patent/PE20021044A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
PE20021044A1 (es)	2002-12-12
HN2002000052A (es)	2003-06-06
GT200200047A (es)	2003-02-13

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EP1324987A1 (de)	2003-07-09	Indazole mit thyroid-hormon-ähnlicher wirkung, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE69429591T2 (de)	2002-08-01	Therapeutisch wirksame Verbindungen
DE2654796A1 (de)	1978-06-08	Polyoxygenierte labdan-derivate
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