HUP0401998A2

HUP0401998A2 - PDE9 inhibitorok alkalmazása olyan gyógyszer előállítására, amellyel inzulin-rezisztencia szindróma és 2-es típusú diabétesz kezelhető

PDE9 inhibitorok alkalmazása olyan gyógyszer előállítására, amellyel inzulin-rezisztencia szindróma és 2-es típusú diabétesz kezelhető Download PDF

Info

Publication number: HUP0401998A2
Authority: HU; Hungary
Prior art keywords: alkyl; group; optionally substituted; phenyl; inhibitor
Prior art date: 2001-11-02

Application number

HU0401998A

Other languages

English (en)

Hungarian (hu)

Inventor

David Albert Fryburg

Earl Michael Gibbs

Original Assignee

Pfizer Products Inc.,

Priority date

2001-11-02

Filing date

2002-09-12

Publication date

2005-01-28

2002-09-12 Application filed by Pfizer Products Inc., filed Critical Pfizer Products Inc.,

2005-01-28 Publication of HUP0401998A2 publication Critical patent/HUP0401998A2/hu

Links

229940076380 PDE9 inhibitor Drugs 0.000 title claims abstract description 58
208000031773 Insulin resistance syndrome Diseases 0.000 title claims abstract description 43
208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 30
238000011282 treatment Methods 0.000 title claims abstract description 28
239000003814 drug Substances 0.000 title claims description 28
238000004519 manufacturing process Methods 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims abstract description 119
150000003839 salts Chemical class 0.000 claims abstract description 87
RVEJWGYZBXCGGM-DNVCBOLYSA-N chembl2179094 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 RVEJWGYZBXCGGM-DNVCBOLYSA-N 0.000 claims abstract description 44
-1 phenoxy, phenyl Chemical group 0.000 claims description 119
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 88
229940002612 prodrug Drugs 0.000 claims description 87
239000000651 prodrug Substances 0.000 claims description 87
239000012453 solvate Substances 0.000 claims description 80
125000000217 alkyl group Chemical group 0.000 claims description 72
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 61
239000002904 solvent Substances 0.000 claims description 58
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
229910052757 nitrogen Inorganic materials 0.000 claims description 47
102000004877 Insulin Human genes 0.000 claims description 44
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229940125396 insulin Drugs 0.000 claims description 44
125000001072 heteroaryl group Chemical group 0.000 claims description 36
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
239000000556 agonist Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
241000124008 Mammalia Species 0.000 claims description 20
239000003085 diluting agent Substances 0.000 claims description 20
239000002552 dosage form Substances 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 19
229940079593 drug Drugs 0.000 claims description 19
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 17
239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 17
102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 15
239000003937 drug carrier Substances 0.000 claims description 15
108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 15
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
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229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
230000009977 dual effect Effects 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
229940123659 Sorbitol dehydrogenase inhibitor Drugs 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 claims description 9
UORHIBXCPUHXFY-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-3-propan-2-yl-2,4-dihydropyrazolo[4,3-d]pyrimidin-7-one Chemical compound CC(C)C1=NNC(C(N2)=O)=C1N=C2CC1=CC=CC(Cl)=C1 UORHIBXCPUHXFY-UHFFFAOYSA-N 0.000 claims description 9
102000014156 AMP-Activated Protein Kinases Human genes 0.000 claims description 8
108010011376 AMP-Activated Protein Kinases Proteins 0.000 claims description 8
208000032928 Dyslipidaemia Diseases 0.000 claims description 8
208000017170 Lipid metabolism disease Diseases 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
229940123208 Biguanide Drugs 0.000 claims description 7
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 7
108010016731 PPAR gamma Proteins 0.000 claims description 7
102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 7
239000003873 peroxisome proliferator activated receptor gamma antagonist Substances 0.000 claims description 7
125000005647 linker group Chemical class 0.000 claims description 6
239000003909 protein kinase inhibitor Substances 0.000 claims description 6
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 5
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 5
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
108090000623 proteins and genes Proteins 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
229940043355 kinase inhibitor Drugs 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
102000004169 proteins and genes Human genes 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
102400001190 Vastatin Human genes 0.000 claims description 2
101800000422 Vastatin Proteins 0.000 claims description 2
229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims description 2
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 2
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 claims description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 8
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 5
229940124186 Dehydrogenase inhibitor Drugs 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 17
238000002360 preparation method Methods 0.000 abstract description 14
206010020772 Hypertension Diseases 0.000 abstract description 8
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
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230000002829 reductive effect Effects 0.000 description 79
ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 64
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
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238000005160 1H NMR spectroscopy Methods 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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235000019341 magnesium sulphate Nutrition 0.000 description 25
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BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 15
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238000003756 stirring Methods 0.000 description 9
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