HRP20100651T1 - 5,7-DIAMINOPIRAZOLO[4,3-d]PIRIMIDINI S AKTIVNOSCU INHIBITORA PDE-5 - Google Patents
5,7-DIAMINOPIRAZOLO[4,3-d]PIRIMIDINI S AKTIVNOSCU INHIBITORA PDE-5 Download PDFInfo
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- HRP20100651T1 HRP20100651T1 HR20100651T HRP20100651T HRP20100651T1 HR P20100651 T1 HRP20100651 T1 HR P20100651T1 HR 20100651 T HR20100651 T HR 20100651T HR P20100651 T HRP20100651 T HR P20100651T HR P20100651 T1 HRP20100651 T1 HR P20100651T1
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- ZTAWTRPFJHKMRU-UHFFFAOYSA-N 7-deaza-8-aza-2,6-diaminopurine Chemical class NC1=NC(N)=C2NN=CC2=N1 ZTAWTRPFJHKMRU-UHFFFAOYSA-N 0.000 title 1
- 101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 89
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 68
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 43
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 40
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 40
- 239000001301 oxygen Chemical group 0.000 claims abstract 40
- 125000005842 heteroatom Chemical group 0.000 claims abstract 37
- 239000011593 sulfur Chemical group 0.000 claims abstract 33
- 229910052717 sulfur Chemical group 0.000 claims abstract 33
- 125000004429 atom Chemical group 0.000 claims abstract 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 27
- 239000001257 hydrogen Substances 0.000 claims abstract 27
- -1 5-trifluoromethyl-1,2,4-triazol-3-yl Chemical group 0.000 claims abstract 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 22
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract 10
- 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 5
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract 3
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000006413 ring segment Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 239000005864 Sulphur Substances 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- ZUHZNKJIJDAJFD-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 ZUHZNKJIJDAJFD-UHFFFAOYSA-N 0.000 claims 2
- PTRFPGZJULTQHY-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 PTRFPGZJULTQHY-UHFFFAOYSA-N 0.000 claims 2
- OLYAXYOJQGRXCA-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 OLYAXYOJQGRXCA-UHFFFAOYSA-N 0.000 claims 2
- HXOCQKOPTWWGOM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[methyl(propyl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)CCC)=NC=1NC1=CC(C)=CC=N1 HXOCQKOPTWWGOM-UHFFFAOYSA-N 0.000 claims 2
- FXAPHZLIRCXSHM-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-(4-fluoro-3-methylanilino)-5-[methyl(propan-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC=C(F)C(C)=C1 FXAPHZLIRCXSHM-UHFFFAOYSA-N 0.000 claims 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 2
- DNUMLNJTFKGLMZ-UHFFFAOYSA-N 3-[1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]-2h-1,2,4-oxadiazol-5-one Chemical compound C12=NC(N(C)CC)=NC(NC=3N=CC=C(C)C=3)=C2N(CCOCC)N=C1C1=NC(=O)ON1 DNUMLNJTFKGLMZ-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010002153 Anal fissure Diseases 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 claims 2
- 208000016583 Anus disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 206010005053 Bladder neck obstruction Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000032544 Cicatrix Diseases 0.000 claims 2
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- 206010013935 Dysmenorrhoea Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000009531 Fissure in Ano Diseases 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
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- 229910002651 NO3 Inorganic materials 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
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- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims 2
- 208000005107 Premature Birth Diseases 0.000 claims 2
- 206010036590 Premature baby Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims 2
- 206010040893 Skin necrosis Diseases 0.000 claims 2
- 208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 206010001053 acute respiratory failure Diseases 0.000 claims 2
- 125000005466 alkylenyl group Chemical group 0.000 claims 2
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- 210000004204 blood vessel Anatomy 0.000 claims 2
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- 230000004761 fibrosis Effects 0.000 claims 2
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- 230000003676 hair loss Effects 0.000 claims 2
- 208000014617 hemorrhoid Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000008991 intestinal motility Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
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- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
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- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
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- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 231100000241 scar Toxicity 0.000 claims 2
- 230000037387 scars Effects 0.000 claims 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- GOKSXAJRWZYOPL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-(4-fluoro-3-methylanilino)pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)CC)=NC=1NC1=CC=C(F)C(C)=C1 GOKSXAJRWZYOPL-UHFFFAOYSA-N 0.000 claims 1
- ULKQZAYKKRMQHT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-[(2-methoxypyrimidin-4-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)CC)=NC=1NC1=CC=NC(OC)=N1 ULKQZAYKKRMQHT-UHFFFAOYSA-N 0.000 claims 1
- VHDKFSITIVUYGS-UHFFFAOYSA-N 1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]-5-(propan-2-ylamino)pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(NC(C)C)=NC=1NC1=CC(C)=CC=N1 VHDKFSITIVUYGS-UHFFFAOYSA-N 0.000 claims 1
- PHBHZBQVOZBEPW-UHFFFAOYSA-N 1-[2-(2,2-difluoroethoxy)ethyl]-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC(F)F)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 PHBHZBQVOZBEPW-UHFFFAOYSA-N 0.000 claims 1
- UMJCJYXTGHKSEF-UHFFFAOYSA-N 1-[2-(2,2-difluoroethoxy)ethyl]-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC(F)F)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 UMJCJYXTGHKSEF-UHFFFAOYSA-N 0.000 claims 1
- RUOASMKTCSCEFG-UHFFFAOYSA-N 1-[2-(3-fluoropropoxy)ethyl]-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCCCF)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 RUOASMKTCSCEFG-UHFFFAOYSA-N 0.000 claims 1
- QAPMQHSUOJHXEP-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)ethyl]-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical class C=12N(CCOCC3CC3)N=C(C(O)=O)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 QAPMQHSUOJHXEP-UHFFFAOYSA-N 0.000 claims 1
- NVORJBTVWKLQKI-UHFFFAOYSA-N 1-[2-(cyclopropylmethoxy)ethyl]-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical class C=12N(CCOCC3CC3)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 NVORJBTVWKLQKI-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- YGVZDIKWVXYLDL-UHFFFAOYSA-N 2-(dimethylamino)ethyl 5-(dimethylamino)-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylate Chemical compound C=12N(CCOCC)N=C(C(=O)OCCN(C)C)C2=NC(N(C)C)=NC=1NC1=CC(C)=CC=N1 YGVZDIKWVXYLDL-UHFFFAOYSA-N 0.000 claims 1
- FQAWADJQDGOZNN-UHFFFAOYSA-N 3-[1-(2-ethoxyethyl)-5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidin-3-yl]-2h-1,2,4-oxadiazol-5-one Chemical compound C12=NC(N(C)C(C)C)=NC(NC=3N=CC=C(C)C=3)=C2N(CCOCC)N=C1C1=NC(=O)ON1 FQAWADJQDGOZNN-UHFFFAOYSA-N 0.000 claims 1
- XUIQMJKVVCTMKZ-UHFFFAOYSA-N 5-(diethylamino)-1-[2-(2,2-difluoroethoxy)ethyl]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCC(F)F)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(CC)CC)=NC=1NC1=CC(C)=CC=N1 XUIQMJKVVCTMKZ-UHFFFAOYSA-N 0.000 claims 1
- OODLQWGZZKCNMK-UHFFFAOYSA-N 5-(diethylamino)-1-[2-(3-fluoropropoxy)ethyl]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCCCF)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(CC)CC)=NC=1NC1=CC(C)=CC=N1 OODLQWGZZKCNMK-UHFFFAOYSA-N 0.000 claims 1
- USPKUTPIUYJNPU-UHFFFAOYSA-N 5-[cyclobutyl(methyl)amino]-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)C2CCC2)=NC=1NC1=CC(C)=CC=N1 USPKUTPIUYJNPU-UHFFFAOYSA-N 0.000 claims 1
- VPOVDEQHKDSSOA-UHFFFAOYSA-N 5-[ethyl(methyl)amino]-1-[2-(3-fluoropropoxy)ethyl]-7-[(4-methylpyridin-2-yl)amino]-n-methylsulfonylpyrazolo[4,3-d]pyrimidine-3-carboxamide Chemical compound C=12N(CCOCCCF)N=C(C(=O)NS(C)(=O)=O)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 VPOVDEQHKDSSOA-UHFFFAOYSA-N 0.000 claims 1
- SHXHBGYPPYAGQC-UHFFFAOYSA-N 5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]-1-(2-propan-2-yloxyethyl)pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOC(C)C)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 SHXHBGYPPYAGQC-UHFFFAOYSA-N 0.000 claims 1
- KSSDSJGVUIINBC-UHFFFAOYSA-N 5-[methyl(propan-2-yl)amino]-7-[(4-methylpyridin-2-yl)amino]-1-(2-propoxyethyl)pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical class C=12N(CCOCCC)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC=N1 KSSDSJGVUIINBC-UHFFFAOYSA-N 0.000 claims 1
- SODJGBFMTJXCCS-UHFFFAOYSA-N 7-(3,4-dimethylanilino)-1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical compound C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)CC)=NC=1NC1=CC=C(C)C(C)=C1 SODJGBFMTJXCCS-UHFFFAOYSA-N 0.000 claims 1
- WLBIWMGZPYVCHV-UHFFFAOYSA-N 7-[(4,6-dimethylpyridin-2-yl)amino]-1-(2-ethoxyethyl)-5-[methyl(propan-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylic acid Chemical class C=12N(CCOCC)N=C(C(O)=O)C2=NC(N(C)C(C)C)=NC=1NC1=CC(C)=CC(C)=N1 WLBIWMGZPYVCHV-UHFFFAOYSA-N 0.000 claims 1
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- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- MWJCGMSTJUEASS-UHFFFAOYSA-N ethyl 1-(2-ethoxyethyl)-5-[ethyl(methyl)amino]-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylate Chemical compound C=12N(CCOCC)N=C(C(=O)OCC)C2=NC(N(C)CC)=NC=1NC1=CC(C)=CC=N1 MWJCGMSTJUEASS-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000003119 guanylate cyclase activator Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002462 imidazolines Chemical class 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KTEHUXPXWAOYEE-UHFFFAOYSA-N methyl 1-(2-ethoxyethyl)-5-[methyl(propan-2-yl)amino]-7-[(6-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylate Chemical compound C=12N(CCOCC)N=C(C(=O)OC)C2=NC(N(C)C(C)C)=NC=1NC1=CC=CC(C)=N1 KTEHUXPXWAOYEE-UHFFFAOYSA-N 0.000 claims 1
- VWDCNBWFAGYJNA-GJZGRUSLSA-N methyl 5-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1-(2-ethoxyethyl)-7-[(4-methylpyridin-2-yl)amino]pyrazolo[4,3-d]pyrimidine-3-carboxylate Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(N=C1C(C(=O)OC)=NN(CCOCC)C1=1)=NC=1NC1=CC(C)=CC=N1 VWDCNBWFAGYJNA-GJZGRUSLSA-N 0.000 claims 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 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 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims 1
- 229960001233 pregabalin Drugs 0.000 claims 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract 3
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
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- Emergency Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB0327319.0A GB0327319D0 (en) | 2003-11-24 | 2003-11-24 | Novel pharmaceuticals |
PCT/IB2004/003747 WO2005049616A1 (en) | 2003-11-24 | 2004-11-12 | 5,7-DIAMINOPYRAZOLO [4,3-d] PYRIMIDINES WITH PDE-5 INHIBITING ACTIVITY |
Publications (1)
Publication Number | Publication Date |
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HRP20100651T1 true HRP20100651T1 (hr) | 2011-01-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20100651T HRP20100651T1 (hr) | 2003-11-24 | 2010-11-26 | 5,7-DIAMINOPIRAZOLO[4,3-d]PIRIMIDINI S AKTIVNOSCU INHIBITORA PDE-5 |
Country Status (44)
Families Citing this family (50)
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CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
WO2006034440A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
WO2006034441A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
WO2006034341A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
TW200626138A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
JP5094398B2 (ja) | 2004-09-20 | 2012-12-12 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環式誘導体およびステアロイル−CoAデサチュラーゼのメディエータとしてのそれらの使用 |
CA2585557C (en) * | 2004-10-28 | 2009-08-18 | Pharmacia & Upjohn Company Llc | Pyrazolo[4,3-d] pyrimidine derivatives useful as pde-5 inhibitors |
BRPI0609225A2 (pt) | 2005-05-12 | 2010-03-09 | Pfizer | formas cristalinas anidras de n-[1-(2-etoxietil)-5-(n-etil-n-metilamino)-7-(4-metilpiridi n-2-il-amino)-1h-pirazolo[4,3-d]pirimidina-3-carbonil] metanossulfonamida, composição farmacêutica compreendendo as mesmas e uso das mesmas |
AU2006343359A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
NL1029244C2 (nl) * | 2005-06-10 | 2006-12-12 | Ronald Silfried Marlin | Middel ter vergroting van het mannelijk geslachtsorgaan. |
DE102005050377A1 (de) * | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Heterocyclische Verbindungen und ihre Verwendung |
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US7601713B2 (en) | 2005-12-15 | 2009-10-13 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
EP1820502A1 (en) * | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
WO2007113243A2 (en) * | 2006-03-31 | 2007-10-11 | Investigación Y Clínica Andrológicas S.L. | Use of pde 5 inhibitors for the treatment of overactive bladder |
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DE102008063992A1 (de) * | 2008-12-19 | 2010-09-02 | Lerner, Zinoviy, Dipl.-Ing. | Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung |
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JP6110937B2 (ja) | 2012-05-04 | 2017-04-05 | ファイザー・インク | APP、BACE1、およびBACE2の阻害剤としての複素環式置換ヘキサヒドロピラノ[3,4−d][1,3]チアジン−2−アミン化合物 |
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CN107787322B (zh) | 2015-06-17 | 2023-07-07 | 辉瑞大药厂 | 三环化合物以及它们作为磷酸二酯酶抑制剂的用途 |
JP2018531924A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | テトラヒドロピラノ[3,4−d][1,3]オキサジン誘導体、およびbace阻害剤としてのその使用 |
JP2018531923A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | N−[2−(2−アミノ−6,6−二置換−4,4a,5,6−テトラヒドロピラノ[3,4−d][1,3]チアジン−8a(8H)−イル)−1,3−チアゾール−4−イル]アミド |
JP2018534251A (ja) | 2015-09-24 | 2018-11-22 | ファイザー・インク | Bace阻害剤として有用なn−[2−(3−アミノ−2,5−ジメチル−1,1−ジオキシド−5,6−ジヒドロ−2h−1,2,4−チアジアジン−5−イル)−1,3−チアゾール−4−イル]アミド |
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HUE054857T2 (hu) | 2016-07-01 | 2021-10-28 | Pfizer | 5,7-dihidro-pirrolo-piridinszármazékok neurológiai és neurodegeneratív betegségek kezelésére |
DK3642202T3 (da) | 2017-06-22 | 2023-01-30 | Pfizer | Dihydro-pyrrolo-pyridin-derivater |
CN112154145B (zh) | 2018-03-23 | 2023-10-17 | 辉瑞大药厂 | 哌嗪氮杂螺衍生物 |
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TW444018B (en) * | 1992-12-17 | 2001-07-01 | Pfizer | Pyrazolopyrimidines |
GB9823102D0 (en) * | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
AU5995699A (en) * | 1998-10-23 | 2000-05-15 | Bunnage, Mark Edward | Pyrazolopyrimidinone cgmp pde5 inhibitors for the treatment of sexual dysfunction |
DE10031236A1 (de) * | 2000-06-27 | 2002-01-10 | Qiagen Gmbh | Verwendung von Carbonsäuren und anderen Additiven in Kombination mit kationischen Verbindungen zur Stabilisierung von Nukleinsäuren in biologischen Materialien |
DE10031584A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
EP1348707B1 (en) * | 2002-03-28 | 2010-08-25 | Ustav Experimentalni Botaniky AV CR, v.v.i. (Institute of Experimental Botany Academy of Sciences of the Czech Republic, PRO) | Pyrazolo[4,3-d]pyrimidines, processes for their preparation and methods for therapy |
JP4015176B2 (ja) * | 2003-04-29 | 2007-11-28 | ファイザー・インク | 高血圧症の治療に有用な5,7−ジアミノピラゾロ4,3−ジピリミジン類 |
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