NO332354B1 - Pyrazolo[3,4-b]pyridin forbindelser, farmasoytisk preparat omfattende slike forbindelser samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom - Google Patents

Pyrazolo[3,4-b]pyridin forbindelser, farmasoytisk preparat omfattende slike forbindelser samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom Download PDF

Info

Publication number: NO332354B1
Authority: NO; Norway
Prior art keywords: ethyl; pyrazolo; pyran; tetrahydro; pyridin
Prior art date: 2002-12-23

Application number

NO20053600A

Other languages

English (en)

Norwegian (no)

Other versions

NO20053600L (no

NO20053600D0 (no

Inventor

Martin Redpath Johnson

Michael Dennis Dowle

Alison Judith Redgrave

Paul Spencer Jones

Caroline Mary Cook

Diane Mary Coe

Julie Nicole Hamblin

David George Allen

Christopher David Edlin

Mika Kristian Lindvall

Charlotte Jane Mitchell

Anthony William James Cooper

Original Assignee

Glaxo Group Ltd

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.)

2002-12-23

Filing date

2005-07-22

Publication date

2012-09-03

2002-12-24 Priority claimed from GB0230165A external-priority patent/GB0230165D0/en

2003-04-07 Priority claimed from GB0307998A external-priority patent/GB0307998D0/en

2005-07-22 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2005-07-22 Publication of NO20053600D0 publication Critical patent/NO20053600D0/no

2005-08-22 Publication of NO20053600L publication Critical patent/NO20053600L/no

2012-09-03 Publication of NO332354B1 publication Critical patent/NO332354B1/no

Links

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238000004519 manufacturing process Methods 0.000 title claims abstract description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 13
201000010099 disease Diseases 0.000 title description 8
239000008194 pharmaceutical composition Substances 0.000 title description 2
150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 176
125000000217 alkyl group Chemical group 0.000 claims abstract description 122
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 98
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 89
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125000000623 heterocyclic group Chemical group 0.000 claims abstract description 46
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NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 132
-1 hydroxyimino Chemical group 0.000 claims description 127
229960004979 fampridine Drugs 0.000 claims description 111
229910052757 nitrogen Inorganic materials 0.000 claims description 74
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125000001424 substituent group Chemical group 0.000 claims description 46
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125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
239000000460 chlorine Substances 0.000 claims description 34
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239000000126 substance Substances 0.000 claims description 32
125000003545 alkoxy group Chemical group 0.000 claims description 31
125000003118 aryl group Chemical group 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
239000011737 fluorine Substances 0.000 claims description 30
229910052731 fluorine Inorganic materials 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 26
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 25
150000001721 carbon Chemical group 0.000 claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
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RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 5
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125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 4
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FHDAFFDIINYJBH-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxolan-2-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2OCCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 FHDAFFDIINYJBH-UHFFFAOYSA-N 0.000 claims description 4
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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 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
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125000001544 thienyl group Chemical group 0.000 claims description 4
125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 3
XXXVUGIOAOGYII-UHFFFAOYSA-N 1-[4-[[1-ethyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]piperidin-1-yl]ethanone Chemical compound N=1C(C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(C)=O)CC1 XXXVUGIOAOGYII-UHFFFAOYSA-N 0.000 claims description 3
HCXYJRAWMUFIKU-UHFFFAOYSA-N 1-[4-[[1-ethyl-5-[3-(morpholin-4-ylmethyl)-1,2,4-oxadiazol-5-yl]pyrazolo[3,4-b]pyridin-4-yl]amino]piperidin-1-yl]ethanone Chemical compound N=1C(CN2CCOCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(C)=O)CC1 HCXYJRAWMUFIKU-UHFFFAOYSA-N 0.000 claims description 3
DZSUIHQGHLXFNA-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DZSUIHQGHLXFNA-UHFFFAOYSA-N 0.000 claims description 3
ONWXJMCAIRWEKW-UHFFFAOYSA-N 1-ethyl-6-methyl-n-(oxan-4-yl)-5-[5-(oxan-4-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2CCOCC2)OC=1C1=C(C)N=C2N(CC)N=CC2=C1NC1CCOCC1 ONWXJMCAIRWEKW-UHFFFAOYSA-N 0.000 claims description 3
YSAHVJSLXAIKQP-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxan-4-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2CCOCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YSAHVJSLXAIKQP-UHFFFAOYSA-N 0.000 claims description 3
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YQIFWOAOYUFYQS-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-propan-2-yl-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC(C)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YQIFWOAOYUFYQS-UHFFFAOYSA-N 0.000 claims description 3
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ZUILTZKVQRVTQS-UHFFFAOYSA-N 5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-4-yl)-1-propylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CCC)N=CC2=C1NC1CCOCC1 ZUILTZKVQRVTQS-UHFFFAOYSA-N 0.000 claims description 3
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KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
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125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
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KTVRYLLWSAKBQE-CYBMUJFWSA-N (4s)-4-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]-1,3-thiazolidin-2-one Chemical compound N=1N=C([C@@H]2NC(=O)SC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KTVRYLLWSAKBQE-CYBMUJFWSA-N 0.000 claims description 2
CVAXMIYRADIZRM-UHFFFAOYSA-N 1-[4-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]piperidin-1-yl]ethanone Chemical compound N=1N=C(C2CCN(CC2)C(C)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CVAXMIYRADIZRM-UHFFFAOYSA-N 0.000 claims description 2
YYQPNWDAHYNNDH-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCOC1 YYQPNWDAHYNNDH-UHFFFAOYSA-N 0.000 claims description 2
WCWOENKXBJFQNM-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1h-1,2,4-triazol-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1NC(C)=NC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WCWOENKXBJFQNM-UHFFFAOYSA-N 0.000 claims description 2
ZENDFWOFRUOXDJ-UHFFFAOYSA-N 1-ethyl-5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C=2C=CC(F)=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZENDFWOFRUOXDJ-UHFFFAOYSA-N 0.000 claims description 2
WQBQOJHYKSRNFC-UHFFFAOYSA-N 1-ethyl-5-[3-[(4-methylpiperazin-1-yl)methyl]-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CN2CCN(C)CC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WQBQOJHYKSRNFC-UHFFFAOYSA-N 0.000 claims description 2
ZOIGVSZGKZCAPP-UHFFFAOYSA-N 1-ethyl-5-[5-(2-methylpyrazol-3-yl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2N(N=CC=2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZOIGVSZGKZCAPP-UHFFFAOYSA-N 0.000 claims description 2
RAROYFBUEHDELU-UHFFFAOYSA-N 1-ethyl-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CS(C)(=O)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RAROYFBUEHDELU-UHFFFAOYSA-N 0.000 claims description 2
QHXXOWPCEDLXIO-UHFFFAOYSA-N 1-ethyl-5-[5-[(2-methylpropan-2-yl)oxymethyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(COC(C)(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QHXXOWPCEDLXIO-UHFFFAOYSA-N 0.000 claims description 2
CAWWLBXDODKJNS-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C(=NON=2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CAWWLBXDODKJNS-UHFFFAOYSA-N 0.000 claims description 2
GTDFYDJUUKTZAZ-IBGZPJMESA-N 1-ethyl-n-(oxan-4-yl)-5-[(4r)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C([C@H](N=1)C=2C=CC=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GTDFYDJUUKTZAZ-IBGZPJMESA-N 0.000 claims description 2
ZSQPYAOFXSYYPS-IBGZPJMESA-N 1-ethyl-n-(oxan-4-yl)-5-[(5r)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound O([C@@H](CN=1)C=2C=CC=CC=2)C=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZSQPYAOFXSYYPS-IBGZPJMESA-N 0.000 claims description 2
KVLMMBNWVFAIBM-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxolan-3-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2COCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KVLMMBNWVFAIBM-UHFFFAOYSA-N 0.000 claims description 2
DWFDHPYYCYEJGN-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-(4-methylphenyl)-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC=2C=CC(C)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DWFDHPYYCYEJGN-UHFFFAOYSA-N 0.000 claims description 2
ARBKPUCEQVJAAF-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-(oxan-4-yl)-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC2CCOCC2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ARBKPUCEQVJAAF-UHFFFAOYSA-N 0.000 claims description 2
RWIAMDUQGXFKKZ-MRXNPFEDSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(1r)-1-(4-methoxyphenyl)ethyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)N[C@H](C)C=2C=CC(OC)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RWIAMDUQGXFKKZ-MRXNPFEDSA-N 0.000 claims description 2
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KAVBNTHXLSERHF-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(2-methylphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C(=CC=CC=2)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KAVBNTHXLSERHF-UHFFFAOYSA-N 0.000 claims description 2
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MJMZBXYBWMBFNY-UHFFFAOYSA-N methyl 4-(4-nitrophenoxy)butanoate Chemical compound COC(=O)CCCOC1=CC=C([N+]([O-])=O)C=C1 MJMZBXYBWMBFNY-UHFFFAOYSA-N 0.000 description 1
SJFKGZZCMREBQH-UHFFFAOYSA-N methyl ethanimidate Chemical compound COC(C)=N SJFKGZZCMREBQH-UHFFFAOYSA-N 0.000 description 1
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SFIXCJOGEZAASK-UHFFFAOYSA-N n-[(2,3-dimethylphenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C(=C(C)C=CC=2)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SFIXCJOGEZAASK-UHFFFAOYSA-N 0.000 description 1
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GOZVQLHJHHUILN-UHFFFAOYSA-N n-cyclohexyl-1-ethyl-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CS(C)(=O)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 GOZVQLHJHHUILN-UHFFFAOYSA-N 0.000 description 1
JUTYFSQACWBXAI-UHFFFAOYSA-N n-cyclopentyl-1-ethyl-5-(5-methyl-1,3,4-thiadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)SC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCC1 JUTYFSQACWBXAI-UHFFFAOYSA-N 0.000 description 1
KGIBSINIIMFPQS-UHFFFAOYSA-N n-cyclopentyl-1-ethyl-5-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCC1 KGIBSINIIMFPQS-UHFFFAOYSA-N 0.000 description 1
WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
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BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
OWELBZTXHNMEKC-UHFFFAOYSA-N tert-butyl n-(4,4-difluorocyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(F)(F)CC1 OWELBZTXHNMEKC-UHFFFAOYSA-N 0.000 description 1
YFTMXYHCMSSHJJ-UHFFFAOYSA-N tert-butyl n-(4-fluorocyclohex-3-en-1-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(F)=CC1 YFTMXYHCMSSHJJ-UHFFFAOYSA-N 0.000 description 1
SMZKPZXYDDZDJG-UHFFFAOYSA-N tert-butyl n-(cyanomethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#N SMZKPZXYDDZDJG-UHFFFAOYSA-N 0.000 description 1
SJFVBEIRXRHKNI-UHFFFAOYSA-N tert-butyl n-[[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridine-5-carbonyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SJFVBEIRXRHKNI-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RPIXOLUIHUFDOY-UHFFFAOYSA-N thian-4-amine Chemical compound NC1CCSCC1 RPIXOLUIHUFDOY-UHFFFAOYSA-N 0.000 description 1
OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
GBNRIMMKLMTDLW-UHFFFAOYSA-N thiolan-3-amine Chemical compound NC1CCSC1 GBNRIMMKLMTDLW-UHFFFAOYSA-N 0.000 description 1
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210000001519 tissue Anatomy 0.000 description 1
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239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Immunology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO20053600A 2002-12-23 2005-07-22 Pyrazolo[3,4-b]pyridin forbindelser, farmasoytisk preparat omfattende slike forbindelser samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom NO332354B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB0230045.7A GB0230045D0 (en)	2002-12-23	2002-12-23	Compounds
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GB0307998A GB0307998D0 (en)	2003-04-07	2003-04-07	Compounds
PCT/EP2003/014867 WO2004056823A1 (en)	2002-12-23	2003-12-19	PYRAZOLO[3,4-b]PYRIDINE COMPOUNDS, AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

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Also Published As

Publication number	Publication date
JP2006513258A (ja)	2006-04-20
EP1581532B1 (en)	2010-04-28
DE60332396D1 (de)	2010-06-10
MXPA05006923A (es)	2005-08-18
AU2010202035A1 (en)	2010-06-10
CO5690642A2 (es)	2006-10-31
AU2010202035B9 (en)	2012-09-13
CA2511340A1 (en)	2004-07-08
CY1110676T1 (el)	2015-06-10
EP1581532A1 (en)	2005-10-05
TW200500364A (en)	2005-01-01
NZ570085A (en)	2009-02-28
PL377880A1 (pl)	2006-02-20
CA2511340C (en)	2013-02-05
US20060252790A1 (en)	2006-11-09
NO20053600L (no)	2005-08-22
ES2345385T3 (es)	2010-09-22
PT1581532E (pt)	2010-07-27
NO20053600D0 (no)	2005-07-22
HK1084384A1 (en)	2006-07-28
KR20050088214A (ko)	2005-09-02
TW201004956A (en)	2010-02-01
ATE466012T1 (de)	2010-05-15
WO2004056823A1 (en)	2004-07-08
BR0317645A (pt)	2005-12-06
JP4872068B2 (ja)	2012-02-08
IL169335A0 (en)	2007-07-04
AU2003293999B2 (en)	2010-05-27
AU2010202035B2 (en)	2012-08-30
AR043683A1 (es)	2005-08-10
AU2003293999A1 (en)	2004-07-14
TWI354671B (en)	2011-12-21
US7528148B2 (en)	2009-05-05
CN1751042B (zh)	2011-02-23
ZA200605901B (en)	2007-12-27
PL392790A1 (pl)	2011-01-03
KR101088848B1 (ko)	2011-12-06
NZ540923A (en)	2008-09-26
CN1751042A (zh)	2006-03-22
GB0230045D0 (en)	2003-01-29
SI1581532T1 (sl)	2010-08-31
DK1581532T3 (da)	2010-08-16
MA27615A1 (fr)	2005-11-01
IS2795B (is)	2012-08-15
IS7913A (is)	2005-06-23

Publication	Publication Date	Title
NO332354B1 (no)	2012-09-03	Pyrazolo[3,4-b]pyridin forbindelser, farmasoytisk preparat omfattende slike forbindelser samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom
EP1539753B1 (en)	2009-09-09	Pyrazolo(3,4-b)pyridine compounds, and their use as phosphodiesterase inhibitors
EP1940835B1 (en)	2011-03-30	Pyrazolo[3,4-b]pyridine compounds, and their use as pde4 inhibitors
WO2005058892A1 (en)	2005-06-30	Pyrazolo [3,4-b] pyridine compounds, and their use as phosphodiesterase inhibitors
WO2005090353A1 (en)	2005-09-29	PYRAZOLO[3,4-b]PYRIDINE COMPOUNDS, AND THEIR USE AS PDE4 INHIBITORS
RU2348633C2 (ru)	2009-03-10	ПИРАЗОЛО[3,4-b]ПИРИДИНОВЫЕ СОЕДИНЕНИЯ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ФОСФОДИЭСТЕРАЗ
RU2357967C2 (ru)	2009-06-10	ПРОИЗВОДНЫЕ ПИРАЗОЛО[3, 4-b]ПИРИДИНА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ (ВАРИАНТЫ), ПРИМЕНЕНИЕ (ВАРИАНТЫ), КОМПОЗИЦИЯ (ВАРИАНТЫ)
TWI283678B (en)	2007-07-11	Pyrazolo[3,4-b]pyridine compounds, and their use as phosphodiesterase inhibitors
AU2003285300B2 (en)	2010-02-11	Pyrazolo[3,4-b]pyridine compounds, and their use as phosphodiesterase inhibitors
EP1737857A1 (en)	2007-01-03	Pyrazolo[3,4-b] pyridine compounds, and their use as phosphodiesterase inhibitors

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2013-05-21	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: GLAXO GROUP LTD, GB
2014-07-21	MM1K	Lapsed by not paying the annual fees