US20060009399A1 - Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors - Google Patents

Info

Publication number

US20060009399A1

US20060009399A1 US11/216,515 US21651505A US2006009399A1 US 20060009399 A1 US20060009399 A1 US 20060009399A1 US 21651505 A US21651505 A US 21651505A US 2006009399 A1 US2006009399 A1 US 2006009399A1

Authority

US

United States

Prior art keywords

alkyl

group

aryl

independently selected

substituted

Prior art date

2001-09-21

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.)

Abandoned

Links

• USPTO
• USPTO PatentCenter
• USPTO Assignment
• Espacenet
• Global Dossier
• Discuss

• 239000003112 inhibitor Substances 0.000 title claims abstract description 96
• 229930182558 Sterol Natural products 0.000 title claims abstract description 80
• 238000010521 absorption reaction Methods 0.000 title claims abstract description 80
• 235000003702 sterols Nutrition 0.000 title claims abstract description 80
• 150000003432 sterols Chemical class 0.000 title claims abstract description 76
• 208000008589 Obesity Diseases 0.000 title claims abstract description 61
• 235000020824 obesity Nutrition 0.000 title claims abstract description 60
• 238000011282 treatment Methods 0.000 title claims abstract description 47
• 238000000034 method Methods 0.000 title claims abstract description 45
• 230000001225 therapeutic effect Effects 0.000 title claims abstract description 44
• 239000000203 mixture Substances 0.000 claims abstract description 109
• 239000003814 drug Substances 0.000 claims abstract description 66
• 229940079593 drug Drugs 0.000 claims abstract description 47
• 150000001875 compounds Chemical class 0.000 claims description 146
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 124
• 125000000217 alkyl group Chemical group 0.000 claims description 120
• 229910052739 hydrogen Inorganic materials 0.000 claims description 114
• -1 R7-benzyl Chemical group 0.000 claims description 109
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 98
• 125000003118 aryl group Chemical group 0.000 claims description 89
• 239000001257 hydrogen Substances 0.000 claims description 71
• 125000001424 substituent group Chemical group 0.000 claims description 60
• 125000005843 halogen group Chemical class 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 33
• 125000001072 heteroaryl group Chemical class 0.000 claims description 32
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000002947 alkylene group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
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• 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
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• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical class 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
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• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
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• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
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• 241000124008 Mammalia Species 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 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
• 108090000623 proteins and genes Proteins 0.000 claims description 6
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims description 5
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
• ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 claims description 5
• 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 239000002899 monoamine oxidase inhibitor Substances 0.000 claims description 5
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 5
• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 5
• DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims description 5
• 102000005962 receptors Human genes 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 239000003762 serotonin receptor affecting agent Substances 0.000 claims description 5
• 230000000476 thermogenic effect Effects 0.000 claims description 5
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 4
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
• 229910018830 PO3H Inorganic materials 0.000 claims description 4
• 229910006069 SO3H Inorganic materials 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004104 aryloxy group Chemical class 0.000 claims description 4
• 125000002047 benzodioxolyl group Chemical class O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000051 benzyloxy group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 4
• DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims description 4
• 229960001582 fenfluramine Drugs 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 229960000395 phenylpropanolamine Drugs 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
• 229940098747 AMPA receptor antagonist Drugs 0.000 claims description 3
• 239000000775 AMPA receptor antagonist Substances 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 102000004864 Fibroblast growth factor 10 Human genes 0.000 claims description 3
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• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 3
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• 239000002981 blocking agent Substances 0.000 claims description 3
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• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• BMQVDVJKPMGHDO-UHFFFAOYSA-K magnesium;potassium;chloride;sulfate;trihydrate Chemical compound O.O.O.[Mg+2].[Cl-].[K+].[O-]S([O-])(=O)=O BMQVDVJKPMGHDO-UHFFFAOYSA-K 0.000 claims description 3
• 229960000299 mazindol Drugs 0.000 claims description 3
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• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 3
• 229940095064 tartrate Drugs 0.000 claims description 3
• 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
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• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 2
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