KR101862420B1 - 치환된 ５－플루오로－１ｈ－피라졸로피리딘 및 그의 용도 - Google Patents
치환된 ５－플루오로－１ｈ－피라졸로피리딘 및 그의 용도 Download PDFInfo
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- KR101862420B1 KR101862420B1 KR1020127033601A KR20127033601A KR101862420B1 KR 101862420 B1 KR101862420 B1 KR 101862420B1 KR 1020127033601 A KR1020127033601 A KR 1020127033601A KR 20127033601 A KR20127033601 A KR 20127033601A KR 101862420 B1 KR101862420 B1 KR 101862420B1
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- fluoro
- methyl
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- LTYNYHHABUSSHS-UHFFFAOYSA-N 5-fluoro-1h-pyrazolo[4,3-b]pyridine Chemical class FC1=CC=C2NN=CC2=N1 LTYNYHHABUSSHS-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
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- 239000003814 drug Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 198
- 239000000203 mixture Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 46
- -1 Methyl {4,6-diamino-2- [5-fluoro-1- (2-fluorobenzyl) -lH- pyrazolo [3,4- b] pyridin- 3- yl] pyrimidin- } Carbamate hydrochloride Chemical compound 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 29
- 208000035475 disorder Diseases 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 24
- 239000012442 inert solvent Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 206010019280 Heart failures Diseases 0.000 claims description 15
- 230000002829 reductive effect Effects 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 13
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
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- 230000003176 fibrotic effect Effects 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 208000017169 kidney disease Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 6
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- 230000008569 process Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 4
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- 230000004761 fibrosis Effects 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 4
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- IQNFKTJVRCTRMX-UHFFFAOYSA-N 2-[5-fluoro-1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl]-5-methylpyrimidine-4,6-diamine 2,2,2-trifluoroethyl carbamate Chemical compound C(N)(OCC(F)(F)F)=O.CC=1C(=NC(=NC1N)C1=NN(C2=NC=C(C=C21)F)CC2=C(C=CC=C2)F)N IQNFKTJVRCTRMX-UHFFFAOYSA-N 0.000 claims description 3
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- FTZNNVLVFBLPQU-UHFFFAOYSA-N C(N)(O)=O.CC=1C(=NC(=NC1N)C1=NN(C2=NC=C(C=C21)F)CC2=C(C=CC=C2)F)N Chemical compound C(N)(O)=O.CC=1C(=NC(=NC1N)C1=NN(C2=NC=C(C=C21)F)CC2=C(C=CC=C2)F)N FTZNNVLVFBLPQU-UHFFFAOYSA-N 0.000 claims description 3
- ITOYZPGDCOBKFK-UHFFFAOYSA-N CNC(O)=O.CC=1C(=NC(=NC1N)C1=NN(C2=NC=C(C=C21)F)CC2=C(C=CC=C2)F)N Chemical compound CNC(O)=O.CC=1C(=NC(=NC1N)C1=NN(C2=NC=C(C=C21)F)CC2=C(C=CC=C2)F)N ITOYZPGDCOBKFK-UHFFFAOYSA-N 0.000 claims description 3
- 206010014664 Endocardial fibrosis Diseases 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- 208000008253 Systolic Heart Failure Diseases 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| DE102010021637.2 | 2010-05-26 | ||
| DE102010021637A DE102010021637A1 (de) | 2010-05-26 | 2010-05-26 | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| PCT/EP2011/058431 WO2011147809A1 (de) | 2010-05-26 | 2011-05-24 | Substituierte 5-fluor-1h-pyrazolopyridine und ihre verwendung |
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| KR20130116000A KR20130116000A (ko) | 2013-10-22 |
| KR101862420B1 true KR101862420B1 (ko) | 2018-07-04 |
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| DE102008063992A1 (de) * | 2008-12-19 | 2010-09-02 | Lerner, Zinoviy, Dipl.-Ing. | Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung |
| DK3415515T3 (da) | 2009-11-27 | 2020-03-16 | Adverio Pharma Gmbh | Fremgangsmåde til fremstilling af methyl-{4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamat |
| WO2011119518A1 (en) | 2010-03-25 | 2011-09-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| CA2800541C (en) | 2010-05-27 | 2016-03-22 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| PE20130779A1 (es) | 2010-07-09 | 2013-06-21 | Bayer Ip Gmbh | Pirimidinas y triazinas condensadas y su uso |
| US8895583B2 (en) | 2010-10-28 | 2014-11-25 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| DE102010043380A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Benzyl-substituierte Carbamate und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| DE102011007272A1 (de) | 2011-04-13 | 2012-10-18 | Bayer Pharma Aktiengesellschaft | Verzweigte 3-Phenylpropionsäure-Derivate und ihre Verwendung |
| WO2012143510A1 (de) | 2011-04-21 | 2012-10-26 | Bayer Intellectual Property Gmbh | Fluoralkyl-substituierte pyrazolopyridine und ihre verwendung |
| EP2594270A3 (en) * | 2011-11-18 | 2013-07-31 | BIP Patents | The use of sGC stimulators, sGC activators, alone and combinations with PDE5 inhibitors for the treatment of systemic sclerosis (SSc) |
| PE20190180A1 (es) * | 2011-11-25 | 2019-02-01 | Adverio Pharma Gmbh | Procedimiento de preparacion de 5-fluoro-1h-pirazolopiridinas sustituidas |
| CN102491974B (zh) | 2011-12-12 | 2013-08-07 | 南京药石药物研发有限公司 | 1-（2-氟苄基）-1H-吡唑并[3，4-b]吡啶-3-甲脒盐酸盐的合成方法 |
| DE102012200349A1 (de) * | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte annellierte Pyrimidine und Triazine und ihre Verwendung |
| DE102012200352A1 (de) * | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung |
| DE102012200360A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| WO2013131923A1 (de) | 2012-03-06 | 2013-09-12 | Bayer Intellectual Property Gmbh | Substituierte azabicyclen und ihre verwendung |
| WO2013144191A1 (de) | 2012-03-29 | 2013-10-03 | Bayer Intellectual Property Gmbh | Substituierte 2 -amino - 3 - cyanopyridine als inhibitoren des natrium calcium austausches und ihre verwendung bei kardiovaskulären erkrankungen |
| CA2879369C (en) | 2012-07-20 | 2020-09-22 | Bayer Pharma Aktiengesellschaft | Novel 5-aminotetrahydroquinoline-2-carboxylic acids and use thereof |
| JP6324956B2 (ja) | 2012-07-20 | 2018-05-16 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換アミノインダン−およびアミノテトラリンカルボン酸ならびにその使用 |
| BR112015012571B1 (pt) | 2012-11-30 | 2022-05-24 | Astellas Pharma Inc | Compostos de imidazopiridina e usos terapêuticos dos mesmos |
| WO2014128109A1 (en) | 2013-02-21 | 2014-08-28 | Bayer Pharma Aktiengesellschaft | Forms of methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridino-3-yl]pyrimidino-5-yl}methyl carbamate |
| EP2961755B1 (de) | 2013-03-01 | 2017-10-18 | Bayer Pharma Aktiengesellschaft | Trifluormethyl-substituierte annellierte pyrimidine und ihre verwendung |
| HK1222852A1 (zh) | 2013-06-21 | 2017-07-14 | Bayer Pharma Aktiengesellschaft | 二氨基杂芳基取代的吡唑 |
| CA2917682A1 (en) | 2013-07-10 | 2015-01-15 | Bayer Pharma Aktiengesellschaft | Benzyl-1h-pyrazolo[3,4-b]pyridines and use thereof |
| WO2015011086A1 (en) | 2013-07-25 | 2015-01-29 | Bayer Pharma Aktiengesellschaft | Sgc stimulators or sgc activators and pde5 inhibitors in combination with additional treatment for the therapy of cystic fibrosis |
| US20160221965A1 (en) | 2013-09-16 | 2016-08-04 | Bayer Pharma Aktiengesellschaft | Disubstituted trifluoromethyl pyrimidinones and their use |
| JP2016532721A (ja) | 2013-10-07 | 2016-10-20 | バイエル ファーマ アクチエンゲゼルシャフト | 環状チエノウラシルカルボキサミドおよびその使用 |
| US9783552B2 (en) | 2013-12-11 | 2017-10-10 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| WO2015088885A1 (en) | 2013-12-11 | 2015-06-18 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| EP3094327A1 (en) | 2014-01-13 | 2016-11-23 | Ironwood Pharmaceuticals, Inc. | USE OF sGC STIMULATORS FOR THE TREATMENT OF NEUROMUSCULAR DISORDERS |
| CA2944614A1 (en) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratoy tract diseases |
| WO2015150363A1 (de) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituierte cyclopentancarbonsäuren und ihre verwendung |
| EP3126340A2 (de) | 2014-04-03 | 2017-02-08 | Bayer Pharma Aktiengesellschaft | Chirale 2,5-disubstituierte cyclopentancarbonsäure-derivate und ihre verwendung |
| US9796733B2 (en) | 2014-06-04 | 2017-10-24 | Merck Sharp & Dohme Corp. | Imidazo-pyrazine derivatives useful as soluble guanylate cyclase activators |
| CN107074773A (zh) | 2014-09-09 | 2017-08-18 | 拜耳制药股份公司 | 取代的n,2‑二芳基喹啉‑4‑甲酰胺及其用途 |
| ES2712886T3 (es) | 2014-09-24 | 2019-05-16 | Bayer Pharma AG | Derivados de piridobenzazepina y piridobenzazocina que inhiben el factor XIa |
| EP3215498B1 (en) | 2014-11-03 | 2018-08-22 | Bayer Pharma Aktiengesellschaft | Hydroxyalkyl-substituted phenyltriazole derivatives and uses thereof |
| TW201625635A (zh) | 2014-11-21 | 2016-07-16 | 默沙東藥廠 | 作為可溶性鳥苷酸環化酶活化劑之三唑并吡基衍生物 |
| WO2016113205A1 (de) | 2015-01-13 | 2016-07-21 | Bayer Pharma Aktiengesellschaft | Substituierte pentafluorethylpyrimidinone und ihre verwendung |
| UY36586A (es) | 2015-03-26 | 2016-10-31 | Bayer Pharma AG | Heterociclilmetiltienouracilos y uso de los mismos |
| HK1243645A1 (zh) | 2015-05-06 | 2018-07-20 | Bayer Pharma Aktiengesellschaft | 单独和与pde5抑制剂组合的sgc刺激剂、sgc活化剂用於治疗伴随系统性硬化症(ssc)的指溃疡(du)的用途 |
| US10245264B2 (en) | 2015-05-27 | 2019-04-02 | Merck Sharp & Dohme Corp. | Substituted imidazo[1,2-a]pyrazines as soluble guanylate cyclase activators |
| US10213429B2 (en) | 2015-05-28 | 2019-02-26 | Merck Sharp & Dohme Corp. | Imidazo-pyrazinyl derivatives useful as soluble guanylate cyclase activators |
| LT3325013T (lt) | 2015-07-23 | 2020-11-10 | Bayer Pharma Aktiengesellschaft | Tirpios guanilatciklazės (sgc) stimuliatoriai/aktyvatoriai derinyje su nep inhibitoriumi ir (arba) angiotenzino aii antagonistu ir jų naudojimas |
| WO2017097671A1 (de) | 2015-12-10 | 2017-06-15 | Bayer Pharma Aktiengesellschaft | Substituierte perhydropyrrolo[3,4-c]pyrrol-derivate und ihre verwendung |
| EP3386979B1 (de) | 2015-12-10 | 2020-07-29 | Bayer Pharma Aktiengesellschaft | 2-phenyl-3-(piperazinomethyl)imidazo[1,2-a]pyridin-derivate als blocker der task-1 und task-2 kanäle zur behandlung von schlafbedingten atemstörungen |
| EA201891416A1 (ru) | 2015-12-14 | 2018-12-28 | Айронвуд Фармасьютикалз, Инк. | ПРИМЕНЕНИЕ СТИМУЛЯТОРОВ sGC ДЛЯ ЛЕЧЕНИЯ ДИСФУНКЦИИ ЖЕЛУДОЧНО-КИШЕЧНОГО СФИНКТЕРА |
| CN105461715B (zh) * | 2015-12-15 | 2017-03-29 | 郑州大明药物科技有限公司 | 一种利奥西呱中间体的合成方法 |
| WO2017107052A1 (en) | 2015-12-22 | 2017-06-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase stimulators |
| WO2017121692A1 (de) | 2016-01-15 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Substituierte sulfamide und ihre verwendung |
| AU2017216429B2 (en) * | 2016-02-01 | 2022-10-06 | Cyclerion Therapeutics, Inc. | Use of sGC stimulators for the treatment of Nonalcoholic Steatohepatitis (NASH) |
| WO2017153235A1 (de) | 2016-03-09 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | Substituierte n-cyclo-3-aryl-1-naphthamide und ihre verwendung |
| WO2017153231A1 (de) | 2016-03-09 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | Substituierte n-cyclo-2-arylisochinolinon-4-carboxamide und ihre verwendung |
| WO2017153234A1 (de) | 2016-03-09 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | Substituierte n-cyclo-2-arylchinolin-4-carboxamide und ihre verwendung |
| US20190119251A1 (en) | 2016-05-03 | 2019-04-25 | Bayer Pharma Aktiengesellschaft | Amide-substituted aryltriazole derivatives and uses thereof |
| AR108263A1 (es) | 2016-05-03 | 2018-08-01 | Bayer Pharma AG | Procedimiento para la preparación de derivados de 1-fenilo-1,2,4-triazol sustituidos por 5-hidroxialquilo |
| US10525041B2 (en) | 2016-05-03 | 2020-01-07 | Bayer Pharma Aktiengesellschaft | Fluoroalkyl-substituted aryltriazole derivatives and uses thereof |
| WO2017191117A1 (en) | 2016-05-03 | 2017-11-09 | Bayer Pharma Aktiengesellschaft | V1a receptor antagonists for use in the treatment of renal diseases |
| US10526314B2 (en) | 2016-05-03 | 2020-01-07 | Bayer Aktiengesellschaft | Hydroxyalkyl-substituted heteroaryltriazole derivatives and uses thereof |
| US9988367B2 (en) | 2016-05-03 | 2018-06-05 | Bayer Pharma Aktiengesellschaft | Amide-substituted pyridinyltriazole derivatives and uses thereof |
| CA3022755A1 (en) | 2016-05-03 | 2017-11-09 | Carsten Schmeck | Oxoalkyl-substituted phenyltriazole derivatives and uses thereof |
| JOP20170113B1 (ar) | 2016-05-09 | 2023-03-28 | Bayer Pharma AG | مركبات 5، 6، 7، 8-رباعي هيدرو [1، 2، 4] تريازولو [4، 3-أ] بيريدين 3(2h)-ون مستبدلة ومركبات 2، 5، 6، 7-رباعي هيدرو-3h-بيرولو [2، 1-ج] [1، 2، 4] تريازول-3-ون واستخداماتها |
| WO2017197555A1 (en) | 2016-05-16 | 2017-11-23 | Merck Sharp & Dohme Corp. | Fused pyrazine derivatives useful as soluble guanylate cyclase stimulators |
| EP3458063A4 (en) | 2016-05-18 | 2020-02-26 | Merck Sharp & Dohme Corp. | METHOD FOR USE OF TRIAZOLO-PYRAZINYL-SOLUBLE GUANYLATE CYCLASE ACTIVATORS IN FIBROTIC DISEASES |
| CN109689654A (zh) | 2016-07-11 | 2019-04-26 | 拜耳医药股份有限公司 | 7-取代的1-吡啶基-萘啶-3-甲酰胺类及其用途 |
| JOP20190005A1 (ar) | 2016-07-20 | 2019-01-20 | Bayer Ag | مركبات ديازاهيترو ثنائية الحلقة مستبدلة واستخداماتها |
| WO2018041771A1 (de) | 2016-09-02 | 2018-03-08 | Bayer Pharma Aktiengesellschaft | (1-methylcyclopropyl)methyl-substituierte thienouracile und ihre verwendung |
| JOP20190045A1 (ar) | 2016-09-14 | 2019-03-14 | Bayer Ag | مركبات أميد حمض 1- أريل-نفثيريدين-3-كربوكسيليك مستبدلة في الموضع 7 واستخدامها. |
| EP3296298A1 (de) | 2016-09-14 | 2018-03-21 | Bayer Pharma Aktiengesellschaft | 7-substituierte 1-aryl-naphthyridin-3-carbonsäureamide und ihre verwendung |
| MX2019003351A (es) | 2016-09-23 | 2019-08-05 | Bayer Ag | Tienouracilos n3-ciclicamente sustituidos y uso de los mismos. |
| WO2018069148A1 (de) | 2016-10-11 | 2018-04-19 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc aktivatoren und mineralocorticoid-rezeptor-antagonisten |
| WO2018069126A1 (de) * | 2016-10-11 | 2018-04-19 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc stimulatoren und mineralocorticoid-rezeptor-antagonisten |
| JOP20190080A1 (ar) | 2016-10-14 | 2019-04-11 | Bayer Pharma AG | مركبات مشتقة من 6-(1h-بيرازول-1-يل) بيريميدين-4- أمين مستبدل واستخداماتها |
| WO2018073144A1 (en) | 2016-10-20 | 2018-04-26 | Bayer Pharma Aktiengesellschaft | Hydroxyalkyl-substituted triazole derivatives and uses thereof |
| WO2018111795A2 (en) | 2016-12-13 | 2018-06-21 | Ironwood Pharmaceuticals, Inc. | Use of sgc stimulators for the treatment of esophageal motility disorders |
| JOP20190141A1 (ar) | 2016-12-21 | 2019-06-12 | Bayer Pharma AG | أشكال جرعات صيدلية تحتوي على مثبطات لقناة task-1 و task-3 واستخدامها في معالجة اضطراب تنفسي |
| JOP20190148A1 (ar) | 2016-12-21 | 2019-06-18 | Bayer Pharma AG | أشكال جرعات صيدلية تحتوي على مثبطات قنوات task-1 و task-3 واستخدامها لمعالجة الاضطرابات التنفسية |
| EP3338764A1 (de) | 2016-12-21 | 2018-06-27 | Bayer Pharma Aktiengesellschaft | Pharmazeutische darreichungsformen enthaltend inhibitoren von task-1 und task-3 kanälen und deren verwendung für die therapie von atemstörungen |
| EP3338803A1 (de) | 2016-12-21 | 2018-06-27 | Bayer Pharma Aktiengesellschaft | Pharmazeutische darreichungsformen enthaltend inhibitoren von task-1 und task-3 kanälen und deren verwendung für die therapie von atemstörungen |
| WO2018153899A1 (de) * | 2017-02-22 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit stimulatoren und/oder aktivatoren der löslichen guanylatcyclase (sgc) |
| AU2018251758B2 (en) | 2017-04-10 | 2021-11-18 | Bayer Aktiengesellschaft | Substituted N-arylethyl-2-arylquinoline-4-carboxamides and use thereof |
| TWI770157B (zh) | 2017-04-10 | 2022-07-11 | 德商拜耳廠股份有限公司 | 經取代之n-芳基乙基-2-胺基喹啉-4-甲醯胺及其用途 |
| CA3056501A1 (en) | 2017-04-11 | 2018-10-18 | Sunshine Lake Pharma Co., Ltd. | Fluorine-substituted indazole compounds and uses thereof |
| CN108690016B (zh) * | 2017-04-11 | 2022-08-12 | 广东东阳光药业有限公司 | 吡唑并吡啶类化合物及其用途 |
| WO2018227427A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Substituted bridged diazepane derivatives and use thereof |
| JOP20190284A1 (ar) | 2017-06-14 | 2019-12-11 | Bayer Pharma AG | مركبات إيميدازوبيريميدين مستبدلة بديازا ثنائي الحلقة واستخدامها للمعالجة من اضطرابات التنفس |
| EP3700898A1 (en) | 2017-10-24 | 2020-09-02 | Bayer Pharma Aktiengesellschaft | Substituted triazole derivatives and uses thereof |
| CA3079770A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Pharma Aktiengesellschaft | Amine substituted triazole derivatives and uses thereof |
| CU20200041A7 (es) * | 2017-10-24 | 2021-03-11 | Bayer Ag | Amidas de imidazopiridina sustituidas |
| EP3700897A1 (en) | 2017-10-24 | 2020-09-02 | Bayer Pharma Aktiengesellschaft | Substituted triazole derivatives and uses thereof |
| CA3084308A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Aktiengesellschaft | Substituted triazole derivatives and uses thereof |
| WO2019081306A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Pharma Aktiengesellschaft | SUBSTITUTED TRIAZOLE DERIVATIVES AND USES THEREOF |
| WO2019081291A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Aktiengesellschaft | PRODRUGS OF SUBSTITUTED TRIAZOLE DERIVATIVES AND USES THEREOF |
| MA50438B1 (fr) | 2017-10-24 | 2022-03-31 | Bayer Pharma AG | Promédicaments de dérivés de triazole substitués, et utilisations de ceux-ci |
| WO2019091847A1 (de) | 2017-11-07 | 2019-05-16 | Bayer Aktiengesellschaft | Substituierte 2,4-dihydro-3h-1,2,4-triazol-3-one und ihre verwendung |
| JP2021504396A (ja) | 2017-12-01 | 2021-02-15 | バイエル ファーマ アクチエンゲゼルシャフト | （３ｓ）−３−（４−クロロ−３−｛［（２ｓ，３ｒ）−２−（４−クロロフェニル）−４，４，４−トリフルオロ−３−メチルブタノイル］アミノ｝フェニル）−３−シクロ−プロピルプロパン酸を製造する方法及び医薬成分として使用するためのその結晶質形態 |
| US11897887B2 (en) * | 2017-12-19 | 2024-02-13 | Tisento Therapeutics Inc. | sGC stimulators |
| EP3553081A1 (en) | 2018-04-12 | 2019-10-16 | Bayer Aktiengesellschaft | Atrial natriuretic peptide engrafted antibodies |
| EP3553079A1 (en) | 2018-04-12 | 2019-10-16 | Bayer Aktiengesellschaft | C-type natriuretic peptide engrafted antibodies |
| EP3553082A1 (en) | 2018-04-12 | 2019-10-16 | Bayer Aktiengesellschaft | Brain natriuretic peptide engrafted antibodies |
| CN112055584A (zh) * | 2018-04-30 | 2020-12-08 | 拜耳公司 | sGC活化剂和sGC刺激剂用于治疗认知障碍的用途 |
| EP3566704A1 (en) | 2018-05-11 | 2019-11-13 | Bayer Aktiengesellschaft | The use of non-steroidal mineralocorticoid receptor antagonists alone or in combination for the treatment of muscular or neuromuscular diseases |
| MA52616A (fr) | 2018-05-15 | 2021-03-24 | Bayer Ag | Benzamides à substitution 1,3-thiazol-2-yl pour le traitement de maladies associées à la sensibilisation de fibres nerveuses |
| JOP20200294A1 (ar) | 2018-05-17 | 2020-11-17 | Bayer Ag | مشتقات ثنائي هيدروبيرازولو بيرازين كربوكساميد تحمل بدائل |
| EP3574905A1 (en) | 2018-05-30 | 2019-12-04 | Adverio Pharma GmbH | Method of identifying a subgroup of patients suffering from dcssc which benefits from a treatment with sgc stimulators and sgc activators in a higher degree than a control group |
| JP7542518B2 (ja) | 2018-07-11 | 2024-08-30 | ティセント セラピューティクス インコーポレーテッド | ミトコンドリア（ｍｉｔｏｃｈｏｎｒｉａｌ）障害の処置のためのｓＧＣ刺激剤の使用 |
| WO2020020789A1 (de) | 2018-07-24 | 2020-01-30 | Bayer Aktiengesellschaft | Oral applizierbare pharmazeutische darreichungsform mit modifizierter freisetzung |
| EP3826619A1 (de) | 2018-07-24 | 2021-06-02 | Bayer Aktiengesellschaft | Oral applizierbare pharmazeutische darreichungsform mit modifizierter freisetzung |
| US10905667B2 (en) | 2018-07-24 | 2021-02-02 | Bayer Pharma Aktiengesellschaft | Orally administrable modified-release pharmaceutical dosage form |
| US20210393624A1 (en) | 2018-11-27 | 2021-12-23 | Bayer Aktiengesellschaft | Process for producing pharmaceutical dosage forms containing task-1 and task-3 channel inhibitors, and the use of same in breathing disorder therapy |
| TWI830835B (zh) | 2018-12-17 | 2024-02-01 | 德商亞德維瑞醫藥有限公司 | 具改善性質之{4,6-二胺基-2-[5-氟-1-(2-氟芐基)-1H-吡唑並[3,4-b]吡啶-3-基]嘧啶-5-基}胺基甲酸甲酯活性化合物產物、其製造及調配物 |
| WO2020164008A1 (en) | 2019-02-13 | 2020-08-20 | Bayer Aktiengesellschaft | Process for the preparation of porous microparticles |
| WO2020216669A1 (de) | 2019-04-23 | 2020-10-29 | Bayer Aktiengesellschaft | Phenylsubstituierte imidazopyridinamide und ihre verwendung |
| PH12021552817A1 (en) | 2019-05-07 | 2022-09-28 | Bayer Ag | Masp inhibitory compounds and uses thereof |
| WO2020245342A1 (en) | 2019-06-07 | 2020-12-10 | Bayer Aktiengesellschaft | The use of sgc activators for the treatment of ophthalmologic diseases |
| GEP20247644B (en) | 2019-11-06 | 2024-07-10 | Bayer Ag | Inhibitors of adrenoreceptor adrac2 |
| WO2021094208A1 (en) | 2019-11-12 | 2021-05-20 | Bayer Aktiengesellschaft | Substituted imidazo pyrimidine ep3 antagonists |
| WO2021094209A1 (en) | 2019-11-12 | 2021-05-20 | Bayer Aktiengesellschaft | Substituted pyrrolo triazine carboxamide derivatives as prostaglandin ep3 receptor antagonists |
| WO2021094210A1 (en) | 2019-11-12 | 2021-05-20 | Bayer Aktiengesellschaft | Substituted pyrazine carboxamide derivatives as prostaglandin ep3 receptor antagonists |
| EP3822268A1 (en) | 2019-11-15 | 2021-05-19 | Bayer Aktiengesellschaft | Substituted hydantoinamides as adamts7 antagonists |
| EP3822265A1 (en) | 2019-11-15 | 2021-05-19 | Bayer AG | Substituted hydantoinamides as adamts7 antagonists |
| US20230067593A1 (en) * | 2020-02-03 | 2023-03-02 | Adverio Pharma Gmbh | Nanoformulations of methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3 -yl]pyrimidin-5-yl} carbamate |
| WO2021167458A1 (en) | 2020-02-21 | 2021-08-26 | Universiteit Maastricht | Use of a soluble guanylate cyclase (sgc) stimulator or of a combination of a sgc stimulator and an sgc activator for conditions wherein the heme group of sgc is oxidized or wherein sgc is deficient in heme |
| US20230083417A1 (en) | 2020-02-26 | 2023-03-16 | Universiteit Maastricht | Therapeutic combination for the treatment of brain ischemia and said therapeutic combination for use in the treatment of brain ischemia |
| US20230130739A1 (en) | 2020-03-26 | 2023-04-27 | Cyclerion Therapeutics, Inc. | DEUTERATED sGC STIMULATORS |
| EP3925953A1 (en) | 2020-06-16 | 2021-12-22 | Adverio Pharma GmbH | Process for preparing methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate |
| WO2022096394A1 (en) | 2020-11-04 | 2022-05-12 | Bayer Aktiengesellschaft | Masp inhibitory compounds and uses thereof |
| EP4011904A1 (en) | 2020-12-14 | 2022-06-15 | Bayer Aktiengesellschaft | Masp inhibitory compounds and uses thereof |
| WO2022112213A1 (en) | 2020-11-30 | 2022-06-02 | Bayer Aktiengesellschaft | Crystalline forms of 3-[[3-(4-chlorophenyl)-5-oxo-4-((2s)-3,3,3-trifluoro- 2-hydroxypropyl)-4,5-dihydro-1h-1,2,4-triazol-1-yl]methyl]-1-[3- (trifluoromethyl)pyridin-2-yl]-1h-1,2,4-triazole-5-carboxamide |
| AU2021398486A1 (en) | 2020-12-10 | 2023-06-22 | Bayer Aktiengesellschaft | The use of sgc activators for the treatment of ophthalmologic diseases |
| EP4011874A1 (en) | 2020-12-10 | 2022-06-15 | Bayer Aktiengesellschaft | Substituted pyrazolo piperidine carboxylic acids |
| CA3204495A1 (en) | 2020-12-10 | 2022-06-16 | Bayer Aktiengesellschaft | Substituted pyrazolo piperidine carboxylic acids |
| US20240109864A1 (en) | 2020-12-10 | 2024-04-04 | Bayer Aktiengesellschaft | Substituted pyrazolyl piperidine carboxylic acids |
| EP4011873A1 (en) | 2020-12-10 | 2022-06-15 | Bayer Aktiengesellschaft | Substituted pyrazolo piperidine carboxylic acids |
| TW202308634A (zh) | 2021-04-20 | 2023-03-01 | 美商賽克瑞恩醫療公司 | 使用sGC刺激劑之CNS疾病治療 |
| EP4326722A1 (en) | 2021-04-20 | 2024-02-28 | Tisento Therapeutics Inc. | Sgc stimulators |
| EP4396185A1 (en) | 2021-08-31 | 2024-07-10 | Teva Pharmaceuticals International GmbH | Solid state forms of vericiguat and process for preparation thereof |
| TW202342012A (zh) | 2021-12-29 | 2023-11-01 | 德商拜耳廠股份有限公司 | 製備用作醫藥活性化合物的（５ｓ）－｛［２－（４－羧基苯基）乙基］［２－（２－｛［３－氯－４＇－（三氟甲基）聯苯－４－基］甲氧基｝苯基）乙基］胺基｝－５，６，７，８－四氫喹啉－２－羧酸及其結晶形式之方法 |
| TW202342035A (zh) | 2021-12-29 | 2023-11-01 | 德商拜耳廠股份有限公司 | 醫藥乾粉吸入配製物 |
| TW202342034A (zh) | 2021-12-29 | 2023-11-01 | 德商拜耳廠股份有限公司 | 心肺病症之治療 |
| ES2956054B2 (es) | 2022-05-03 | 2024-07-01 | Moehs Iberica Sl | 2-(5-FLUORO-1-(2-FLUOROBENCIL)-1H-PIRAZOLO[3,4-b]PIRIDIN-3-IL)-5-NITROSOPIRIMIDIN-4,6-DIAMINA O UNA SAL DE LA MISMA, PROCEDIMIENTO PARA SU PREPARACION Y SU USO EN LA SINTESIS DE VERICIGUAT |
| CN119300815A (zh) | 2022-06-09 | 2025-01-10 | 拜耳公司 | 用于治疗女性射血分数保留型心力衰竭的可溶性鸟苷酸环化酶激活剂 |
| JP2025536343A (ja) | 2022-10-18 | 2025-11-05 | ティセント セラピューティクス インコーポレーテッド | ピリミジンｓｇｃ刺激剤 |
| EP4605080A1 (en) | 2022-10-18 | 2025-08-27 | Tisento Therapeutics Inc. | Treatment of mitochondrial diseases with sgc stimulators |
| CN116239609A (zh) * | 2022-12-06 | 2023-06-09 | 山东百诺医药股份有限公司 | 一种维立西呱的关键杂质及其制备方法 |
| AR133983A1 (es) | 2023-09-28 | 2025-11-19 | Bayer Ag | Carboxamidas heterocíclicas sustituidas y su uso |
| WO2025114276A1 (en) | 2023-12-01 | 2025-06-05 | Krka, D.D., Novo Mesto | Solid oral composition comprising vericiguat |
| US20250205235A1 (en) | 2023-12-20 | 2025-06-26 | Adverio Pharma Gmbh | Dose regimen for vericiguat |
| CN117924280B (zh) * | 2024-03-20 | 2024-07-12 | 中国人民解放军军事科学院军事医学研究院 | 取代噻吩基-5-氟-1h-吡唑并吡啶类化合物及其用途 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998016223A1 (de) | 1996-10-14 | 1998-04-23 | Bayer Aktiengesellschaft | Verwendung von 1-benzyl-3-(substituiertes-hetaryl)-kondensierten pyrazol-derivaten zur belandlung von speziellen erkrankungen des herz-kreislaufsystems und des zentralnervensystems |
| WO2000006569A1 (de) | 1998-07-29 | 2000-02-10 | Bayer Aktiengesellschaft | Mit sechsgliedrigen heterocyclischen ringen kondensierte substituierte pyrazolderivate |
| WO2003095451A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Healthcare Ag | Carbamat-substituierte pyrazolopyridine |
Family Cites Families (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01198481A (ja) * | 1988-02-01 | 1989-08-10 | Canon Inc | マイクロ波プラズマｃｖｄ法による堆積膜形成法 |
| GB9013750D0 (en) | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| EP0463754A1 (en) | 1990-06-25 | 1992-01-02 | Rohm And Haas Company | Stabilization of glutarimide polymers |
| DK181190D0 (da) | 1990-07-30 | 1990-07-30 | Lundbeck & Co As H | 3-aryl-indol- eller 3-aryl-indazolderivater |
| GB9301192D0 (en) | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
| GB9314412D0 (en) | 1993-07-13 | 1993-08-25 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| JP4351298B2 (ja) | 1996-10-14 | 2009-10-28 | バイエル・アクチエンゲゼルシヤフト | 新規へテロシクリルメチル置換ピラゾール誘導体 |
| US6008243A (en) | 1996-10-24 | 1999-12-28 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use |
| FR2757157B1 (fr) | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| HRP20020585B1 (hr) | 1997-11-12 | 2013-02-28 | Bayer Schering Pharma Aktiengesellschaft | 2-fenil supstituirani imidazotriazinoni kao inhibitori fosfodiesteraze |
| US6451805B1 (en) | 1997-11-14 | 2002-09-17 | Bayer Aktiengesellschaft | Substituted pyrazole derivatives for the treatment of cardiocirculatory diseases |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834045A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | (4-Amino-5-ethylpyrimidin-2-yl)-1-(2-fluorbenzyl)-1H-pyrazolo[3,4-b]pyridin |
| DE19846514A1 (de) | 1998-10-09 | 2000-04-20 | Bayer Ag | Neue Heterocyclyl-methyl-substituierte Pyrazole |
| GB0002666D0 (en) | 2000-02-04 | 2000-03-29 | Univ London | Blockade of voltage dependent sodium channels |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| CA2429308C (en) | 2000-11-22 | 2010-09-21 | Bayer Aktiengesellschaft | Novel lactam-substituted pyrazolopyridine derivatives |
| DE10057751A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Carbamat-substituierte Pyrazolopyridinderivate |
| DE10057754A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Sulfonamid-substituierte Pyrazolopyridinderivate |
| NZ526871A (en) | 2001-01-25 | 2006-01-27 | Bristol Myers Squibb Co | Pharmaceutical dosage forms of epothilones for oral administration |
| DE10122894A1 (de) | 2001-05-11 | 2002-11-14 | Bayer Ag | Neue Sulfonat-substituierte Pyrazolopyridinderivate |
| DE10132416A1 (de) | 2001-07-04 | 2003-01-16 | Bayer Ag | Neue Morpholin-überbrückte Pyrazolopyridinderivate |
| WO2003035005A2 (en) | 2001-10-26 | 2003-05-01 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
| US7790905B2 (en) | 2002-02-15 | 2010-09-07 | Mcneil-Ppc, Inc. | Pharmaceutical propylene glycol solvate compositions |
| WO2003076408A2 (en) | 2002-03-08 | 2003-09-18 | Abbott Laboratories | Indazole derivatives that are activators of soluble guanylate cyclase |
| GR1004350B (el) * | 2002-03-29 | 2003-09-26 | Συσκευη εισπνοων ξηρης σκονης | |
| DE10222550A1 (de) | 2002-05-17 | 2003-11-27 | Bayer Ag | Substituierte Benzyl-pyrazolopyridine |
| DE10232571A1 (de) | 2002-07-18 | 2004-02-05 | Bayer Ag | 4-Aminosubstituierte Pyrimidinderivate |
| DE10232572A1 (de) | 2002-07-18 | 2004-02-05 | Bayer Ag | Neue 2,5-disubstituierte Pyrimidinderivate |
| DE10242941A1 (de) | 2002-09-16 | 2004-03-18 | Bayer Ag | Substituiertes Pyrazolderivat |
| DE10244810A1 (de) | 2002-09-26 | 2004-04-08 | Bayer Ag | Neue Morpholin-überbrückte Indazolderivate |
| BRPI0306214B1 (pt) | 2002-11-20 | 2017-08-08 | Japan Tobacco Inc. | 4-oxoquinoline compound and use of this as a hiv integrase inhibitor |
| ATE480520T1 (de) | 2003-05-09 | 2010-09-15 | Asahi Glass Co Ltd | Verfahren zur herstellung von 3-substituiertem 2- chlor-5-fluorpyridin bzw. einem salz davon |
| JP4499721B2 (ja) | 2003-06-30 | 2010-07-07 | ヒフ バイオ，インク． | 化合物、組成物および方法 |
| PE20050483A1 (es) | 2003-10-31 | 2005-08-25 | Arena Pharm Inc | Derivados de tetrazol de formula (i), sus composiciones farmaceuticas y procesos para producir composiciones farmaceuticas |
| CN100355732C (zh) | 2003-11-03 | 2007-12-19 | 上海药明康德新药开发有限公司 | 2－氯－5－氟－烟酸酯及酸的制备方法 |
| DE10351903A1 (de) | 2003-11-06 | 2005-06-09 | Bayer Healthcare Ag | Neue Kombination |
| GB0403819D0 (en) | 2004-02-20 | 2004-03-24 | Merck Sharp & Dohme | New compounds |
| US7514463B2 (en) | 2004-08-20 | 2009-04-07 | University Of Kansas | Lonidamine analogues and their use in male contraception and cancer treatment |
| JP2008515825A (ja) | 2004-10-05 | 2008-05-15 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 気管支収縮および肺血管収縮の処置用のグアニル酸シクラーゼ刺激因子および一酸化窒素 |
| DE102005047945A1 (de) | 2005-07-16 | 2007-01-18 | Bayer Healthcare Ag | Verwendung von Aktivatoren der löslichen Guanylatzyklase zur Behandlung von Raynaud Phänomenen |
| BRPI0614001A2 (pt) | 2005-07-18 | 2011-03-01 | Bayer Healthcare Ag | uso de ativadores e estimuladores de guanilato ciclase solúvel para a prevenção ou tratamento de distúrbios renais |
| DE102006021733A1 (de) | 2006-05-09 | 2007-11-22 | Bayer Healthcare Ag | 3-Tetrazolylindazole und 3-Tetrazolylpyrazolopyridine sowie ihre Verwendung |
| DE102006043443A1 (de) | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| EP2170884A2 (en) | 2007-06-25 | 2010-04-07 | Boehringer Ingelheim International GmbH | Chemical compounds |
| JP5553751B2 (ja) | 2007-07-31 | 2014-07-16 | バーテックス ファーマシューティカルズ インコーポレイテッド | ５−フルオロ−１Ｈ−ピラゾロ［３，４−ｂ］ピリジン−３−アミンおよびその誘導体を調製するためのプロセス |
| JP2011513483A (ja) | 2008-03-10 | 2011-04-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | タンパク質キナーゼの阻害剤として有用なピリミジンおよびピリジン |
| DE102008063992A1 (de) * | 2008-12-19 | 2010-09-02 | Lerner, Zinoviy, Dipl.-Ing. | Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung |
| DE102009004245A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung |
| AR077898A1 (es) | 2009-08-26 | 2011-09-28 | Nycomed Gmbh | Metilpirrolopirimidincarboxamidas |
| DK3415515T3 (da) | 2009-11-27 | 2020-03-16 | Adverio Pharma Gmbh | Fremgangsmåde til fremstilling af methyl-{4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}methylcarbamat |
| UY33040A (es) | 2009-11-27 | 2011-06-30 | Bayer Schering Pahrma Akitengesellschaft | Nuevas formas polimorfas de {4,6diamino-2-[1-(2-fluorobencil-1h-pirazol[3,4-b]piridin-3-il]pirimidin-5-il}carbamato de metilo |
| UY33041A (es) | 2009-11-27 | 2011-06-30 | Bayer Schering Pharma Aktienegesellschaft | Procedimiento para la preparaciòn de {4,6-diamino-2-[1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}carbamato de metilo y su purificaciòn para el uso como principio activo farmacèutico |
| JP5960061B2 (ja) | 2009-12-18 | 2016-08-02 | エクソドス ライフ サイエンシーズ リミテッド パートナーシップ | 末梢血管疾患を治療するための方法および組成物 |
| WO2011115804A1 (en) | 2010-03-17 | 2011-09-22 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| MX2012013574A (es) * | 2010-05-26 | 2013-01-24 | Bayer Ip Gmbh | El uso de estimuladores de la sgc, activadores de la sgc, solos y en combinacion con inhibidores de la pde5 para el tratamiento de esclerosis sistemica (ecs). |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| CA2800541C (en) | 2010-05-27 | 2016-03-22 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| PE20130779A1 (es) | 2010-07-09 | 2013-06-21 | Bayer Ip Gmbh | Pirimidinas y triazinas condensadas y su uso |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010040234A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Verfahren zur Herstellung von 5-Flour-1H-pyrazolo[3,4-b]pyridin-3-carbonitril |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| DE102010043380A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Benzyl-substituierte Carbamate und ihre Verwendung |
| CA2835220A1 (en) | 2011-05-31 | 2012-12-06 | Theravance, Inc. | Neprilysin inhibitors |
| WO2013030288A1 (de) | 2011-09-02 | 2013-03-07 | Bayer Intellectual Property Gmbh | Substituierte annellierte pyrimidine und ihre verwendung |
| PE20190180A1 (es) | 2011-11-25 | 2019-02-01 | Adverio Pharma Gmbh | Procedimiento de preparacion de 5-fluoro-1h-pirazolopiridinas sustituidas |
| DE102012200352A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998016223A1 (de) | 1996-10-14 | 1998-04-23 | Bayer Aktiengesellschaft | Verwendung von 1-benzyl-3-(substituiertes-hetaryl)-kondensierten pyrazol-derivaten zur belandlung von speziellen erkrankungen des herz-kreislaufsystems und des zentralnervensystems |
| WO2000006569A1 (de) | 1998-07-29 | 2000-02-10 | Bayer Aktiengesellschaft | Mit sechsgliedrigen heterocyclischen ringen kondensierte substituierte pyrazolderivate |
| WO2003095451A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Healthcare Ag | Carbamat-substituierte pyrazolopyridine |
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