JP2015524828A5 - - Google Patents
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- JP2015524828A5 JP2015524828A5 JP2015526856A JP2015526856A JP2015524828A5 JP 2015524828 A5 JP2015524828 A5 JP 2015524828A5 JP 2015526856 A JP2015526856 A JP 2015526856A JP 2015526856 A JP2015526856 A JP 2015526856A JP 2015524828 A5 JP2015524828 A5 JP 2015524828A5
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- JP
- Japan
- Prior art keywords
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- membered
- substituent
- substituents
- alkyl
- Prior art date
- 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.)
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- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 cyano, amino, hydroxyl Chemical group 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 15
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 7
- 239000005977 Ethylene Chemical group 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 206010020853 Hypertonic bladder Diseases 0.000 claims 2
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000020629 overactive bladder Diseases 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 claims 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 241000239366 Euphausiacea Species 0.000 claims 1
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010071289 Lower urinary tract symptoms Diseases 0.000 claims 1
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 1
- 239000002160 alpha blocker Substances 0.000 claims 1
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 claims 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 claims 1
- 229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 claims 1
- 229960000711 alprostadil Drugs 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960001123 epoprostenol Drugs 0.000 claims 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims 1
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- 150000004897 thiazines Chemical class 0.000 claims 1
- 230000002227 vasoactive effect Effects 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 claims 1
- 239000003071 vasodilator agent Substances 0.000 claims 1
- 0 *[C@](CI*)c1c(C(N(*)*)=O)c(*)nc(*)n1 Chemical compound *[C@](CI*)c1c(C(N(*)*)=O)c(*)nc(*)n1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210289185 | 2012-08-14 | ||
| CN201210289185.3 | 2012-08-14 | ||
| PCT/CN2013/000953 WO2014026467A1 (zh) | 2012-08-14 | 2013-08-14 | 双环取代的嘧啶类化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015524828A JP2015524828A (ja) | 2015-08-27 |
| JP2015524828A5 true JP2015524828A5 (https=) | 2016-11-10 |
| JP6037489B2 JP6037489B2 (ja) | 2016-12-07 |
Family
ID=50101233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015526856A Active JP6037489B2 (ja) | 2012-08-14 | 2013-08-14 | 二環性基置換ピリミジン化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9359371B2 (https=) |
| EP (1) | EP2886540B1 (https=) |
| JP (1) | JP6037489B2 (https=) |
| KR (1) | KR101794321B1 (https=) |
| CN (1) | CN104487434B (https=) |
| BR (1) | BR112015003232B1 (https=) |
| ES (1) | ES2641992T3 (https=) |
| WO (1) | WO2014026467A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101749314B1 (ko) | 2013-03-29 | 2017-07-03 | 수안주 파마 코포레이션 리미티드 | 비사이클릭-치환된 피리미딘 타입 pde-5 억제제의 프로드러그 |
| CN111406053B (zh) * | 2017-12-11 | 2023-03-31 | 轩竹生物科技股份有限公司 | 磷酸二酯酶-5抑制剂的晶型 |
| CN109438421A (zh) * | 2018-11-13 | 2019-03-08 | 扬州市三药制药有限公司 | 一种阿伐那非中间体的精制纯化方法 |
| WO2020177129A1 (zh) * | 2019-03-07 | 2020-09-10 | 华东理工大学 | 2,7-二氮杂-螺[4.4]壬烷类异羟肟酸嘧啶类化合物及其制备和应用 |
| WO2020177128A1 (zh) * | 2019-03-07 | 2020-09-10 | 华东理工大学 | 2,6-二氮杂螺[3.4]辛烷类嘧啶-异羟肟酸化合物及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1219609B1 (en) | 1999-09-16 | 2007-04-04 | Tanabe Seiyaku Co., Ltd. | Aromatic nitrogenous six-membered ring compounds |
| JP3637961B2 (ja) * | 1999-09-16 | 2005-04-13 | 田辺製薬株式会社 | 芳香族含窒素六員環化合物 |
| US7087597B1 (en) * | 1999-10-12 | 2006-08-08 | Takeda Pharmaceutical Company Limited | Pyrimidine 5-carboxamide compounds, process for producing the same and use thereof |
| JP2001233875A (ja) * | 1999-10-12 | 2001-08-28 | Takeda Chem Ind Ltd | ピリミジン−５−カルボキサミド化合物、その製造法およびその用途 |
| NZ522217A (en) * | 2000-04-28 | 2004-04-30 | Tanabe Seiyaku Co | Cyclic compounds |
| NZ524572A (en) | 2000-09-06 | 2004-08-27 | Tanabe Seiyaku Co | Oral compositions comprising phosphodiesterase inhibitors ( PDE inhibitor )and an acidic substance such as fumaric acid with improved drug efficacy due to decrease solubility in neutral and alkaline regions |
| JP4178816B2 (ja) * | 2001-03-15 | 2008-11-12 | 田辺三菱製薬株式会社 | 医薬組成物 |
| WO2008024974A1 (en) | 2006-08-24 | 2008-02-28 | Serenex, Inc. | Pyrimidine and pyrazine derivatives |
| NZ588830A (en) * | 2008-04-22 | 2012-11-30 | Portola Pharm Inc | Inhibitors of protein kinases |
| CN102372697A (zh) | 2010-08-19 | 2012-03-14 | 山东轩竹医药科技有限公司 | 取代的嘧啶类化合物 |
| US20140107100A1 (en) | 2010-11-24 | 2014-04-17 | Exelixis, Inc. | Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture |
| JP5697800B2 (ja) | 2011-07-21 | 2015-04-08 | シュエンジュウ・ファーマ・カンパニー・リミテッド | 複素環置換ピリミジン化合物 |
-
2013
- 2013-08-14 CN CN201380039519.4A patent/CN104487434B/zh active Active
- 2013-08-14 KR KR1020157006568A patent/KR101794321B1/ko active Active
- 2013-08-14 BR BR112015003232A patent/BR112015003232B1/pt active IP Right Grant
- 2013-08-14 WO PCT/CN2013/000953 patent/WO2014026467A1/zh not_active Ceased
- 2013-08-14 US US14/421,703 patent/US9359371B2/en active Active
- 2013-08-14 ES ES13829720.5T patent/ES2641992T3/es active Active
- 2013-08-14 EP EP13829720.5A patent/EP2886540B1/en active Active
- 2013-08-14 JP JP2015526856A patent/JP6037489B2/ja active Active
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