ES2231581T3 - Nuevos derivados de pirazolopiridina sustituidos con lactama. - Google Patents
Nuevos derivados de pirazolopiridina sustituidos con lactama.Info
- Publication number
- ES2231581T3 ES2231581T3 ES01997487T ES01997487T ES2231581T3 ES 2231581 T3 ES2231581 T3 ES 2231581T3 ES 01997487 T ES01997487 T ES 01997487T ES 01997487 T ES01997487 T ES 01997487T ES 2231581 T3 ES2231581 T3 ES 2231581T3
- Authority
- ES
- Spain
- Prior art keywords
- compounds
- formula
- group
- general formula
- necessary
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 150000004677 hydrates Chemical class 0.000 claims abstract description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 16
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 241000670727 Amida Species 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 208000001435 Thromboembolism Diseases 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 230000002425 cardiocirculatory effect Effects 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 206010020852 Hypertonia Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 210000000653 nervous system Anatomy 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- -1 organic nitrates Chemical class 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 description 10
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 235000019256 formaldehyde Nutrition 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 206010012289 Dementia Diseases 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 208000006011 Stroke Diseases 0.000 description 7
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- LQCFFAGUCURQEC-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridine-3-carboximidamide Chemical compound C12=NC=CC=C2C(C(=N)N)=NN1CC1=CC=CC=C1F LQCFFAGUCURQEC-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000003951 lactams Chemical class 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
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- 239000008096 xylene Substances 0.000 description 5
- QOMRCMAKWINLAN-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridine-3-carboxylic acid Chemical compound C12=NC=CC=C2C(C(=O)O)=NN1CC1=CC=CC=C1F QOMRCMAKWINLAN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FSVPXQBHTLFIIJ-UHFFFAOYSA-N 2-(2-oxo-1,3-oxazolidin-3-yl)acetonitrile Chemical compound O=C1OCCN1CC#N FSVPXQBHTLFIIJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010078321 Guanylate Cyclase Proteins 0.000 description 3
- 102000014469 Guanylate cyclase Human genes 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
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- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 201000004810 Vascular dementia Diseases 0.000 description 2
- OQQVFCKUDYMWGV-UHFFFAOYSA-N [5-[1-(phenylmethyl)-3-indazolyl]-2-furanyl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC=C1 OQQVFCKUDYMWGV-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| DE10057752 | 2000-11-22 | ||
| DE10057752 | 2000-11-22 | ||
| DE10122895A DE10122895A1 (de) | 2000-11-22 | 2001-05-11 | Neue Lactam-substituierte Pyrazolopyridinderivate |
| DE10122895 | 2001-05-11 |
Publications (1)
| Publication Number | Publication Date |
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| ES2231581T3 true ES2231581T3 (es) | 2005-05-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01997487T Expired - Lifetime ES2231581T3 (es) | 2000-11-22 | 2001-11-09 | Nuevos derivados de pirazolopiridina sustituidos con lactama. |
Country Status (7)
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| EP (1) | EP1339716B1 (https=) |
| JP (1) | JP4295505B2 (https=) |
| AU (1) | AU2002221827A1 (https=) |
| CA (1) | CA2429308C (https=) |
| ES (1) | ES2231581T3 (https=) |
| WO (1) | WO2002042299A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10220570A1 (de) * | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| DK1522314T3 (da) * | 2002-06-26 | 2014-05-26 | Ono Pharmaceutical Co | Midler for sygdomme forårsaget af vaskulær sammentrækning eller udvidelse |
| DE10232572A1 (de) * | 2002-07-18 | 2004-02-05 | Bayer Ag | Neue 2,5-disubstituierte Pyrimidinderivate |
| DE10244810A1 (de) | 2002-09-26 | 2004-04-08 | Bayer Ag | Neue Morpholin-überbrückte Indazolderivate |
| DE102006043443A1 (de) | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102006054757A1 (de) * | 2006-11-21 | 2008-05-29 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102007026392A1 (de) * | 2007-06-06 | 2008-12-11 | Bayer Healthcare Ag | Lösungen für die Perfusion und Konservierung von Organen und Geweben |
| AU2009322836B2 (en) | 2008-11-25 | 2013-04-04 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| 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 |
| DE102009012314A1 (de) * | 2009-03-09 | 2010-09-16 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Alkylcarbonsäuren und ihre Verwendung |
| CN102020616B (zh) * | 2009-09-11 | 2013-03-27 | 中国中化股份有限公司 | 一种2-(3-氧代吗啉基)乙腈的制备方法 |
| PH12012501023A1 (en) | 2009-11-27 | 2014-12-19 | Adverio Pharma Gmbh | Method for producing methyl - {4, 6-diamino -2-[1- (2-fluorobenzyl) -1h- pyrazolo [3,4-b] pyridino -3-yl] pyrimidino -5-yl} methyl carbamate and its purification for use thereof as pharmaceutical substance |
| 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 |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| UA107112C2 (uk) * | 2010-05-27 | 2014-11-25 | Мерк Шарп Енд Доме Корп. | Активатори розчинної гуанілатциклази |
| PE20130779A1 (es) | 2010-07-09 | 2013-06-21 | Bayer Ip Gmbh | Pirimidinas y triazinas condensadas y su uso |
| EP2590987B1 (de) * | 2010-07-09 | 2016-03-09 | Bayer Intellectual Property GmbH | Annellierte 4-aminopyrimidine und ihre verwendung als stimulatoren der löslichen guanylatcyclase |
| DE102010031665A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Oxazolidinone und Oxazinanone und ihre Verwendung |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| EP2632551B1 (en) | 2010-10-28 | 2016-07-06 | 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 |
| ES2583086T3 (es) | 2011-04-21 | 2016-09-19 | Bayer Intellectual Property Gmbh | Pirazolopiridinas sustituidas con fluoroalquilo y su uso |
| KR20140050029A (ko) * | 2011-07-06 | 2014-04-28 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 헤테로아릴-치환된 피라졸로피리딘 및 가용성 구아닐레이트 시클라제 자극제로서의 그의 용도 |
| CN104039784B (zh) | 2011-09-02 | 2017-08-22 | 拜耳知识产权有限责任公司 | 取代的增环嘧啶及其用途 |
| PE20142359A1 (es) | 2011-11-25 | 2015-01-09 | Bayer Pharma AG | Procedimiento de preparacion de 5-fluoro-1h-pirazolopiridinas sustituidas |
| DE102012200360A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| 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 |
| ES2644781T3 (es) | 2012-03-06 | 2017-11-30 | Bayer Intellectual Property Gmbh | Azabiciclos sustituidos y su uso |
| MX2015002399A (es) * | 2012-10-29 | 2015-06-10 | Hoffmann La Roche | Derivados de oxazolidinona 3,4-disustituidos y su uso como inhibidores del canal de potasio activado con calcio. |
| CN105102457A (zh) | 2013-02-21 | 2015-11-25 | 阿德弗里奥药品有限责任公司 | {4,6-二氨基-2-[1-(2-氟苄基)-1H-吡唑并[3,4-b]吡啶-3-基]嘧啶-5-基}甲基氨基甲酸甲酯的形式 |
| WO2014131760A1 (de) | 2013-03-01 | 2014-09-04 | Bayer Pharma Aktiengesellschaft | Trifluormethyl-substituierte annellierte pyrimidine und ihre verwendung |
| AU2014289312A1 (en) | 2013-07-10 | 2016-02-11 | Bayer Pharma Aktiengesellschaft | Benzyl-1H-pyrazolo(3,4-b)pyridines and use thereof |
| EP3062780A1 (en) | 2013-11-01 | 2016-09-07 | Bergen Teknologioverføring AS | Activators or stimulators of soluble guanylate cyclase for use in treating chronic fatigue syndrome |
| CN107580495A (zh) | 2015-05-06 | 2018-01-12 | 拜耳制药股份公司 | 单独和与PDE5抑制剂组合的sGC刺激剂、sGC活化剂用于治疗伴随系统性硬化症(SSc)的指溃疡(DU)的用途 |
| WO2017013010A1 (de) | 2015-07-23 | 2017-01-26 | Bayer Pharma Aktiengesellschaft | Stimulatoren und/oder aktivatoren der löslichen guanylatzyklase (sgc) in kombination mit einem inhibitor der neutralen endopeptidase (nep inhibitor) und/oder einem angiotensin aii-antagonisten und ihre verwendung |
| AU2016371762A1 (en) | 2015-12-14 | 2018-06-21 | Cyclerion Therapeutics, Inc. | Use of sGC stimulators for the treatment of gastrointestinal sphincter dysfunction |
| US10918639B2 (en) | 2016-10-11 | 2021-02-16 | Bayer Pharma Aktiengesellschaft | Combination containing SGC stimulators and mineralocorticoid receptor antagonists |
| CA3039735A1 (en) | 2016-10-11 | 2018-04-19 | Bayer Pharma Aktiengesellschaft | Combination containing sgc activators and mineralocorticoid receptor antagonists |
| WO2018111795A2 (en) | 2016-12-13 | 2018-06-21 | Ironwood Pharmaceuticals, Inc. | Use of sgc stimulators for the treatment of esophageal motility disorders |
| CA3100096A1 (en) | 2018-05-15 | 2019-11-21 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides for the treatment of diseases associated with nerve fiber sensitization |
| WO2020164008A1 (en) | 2019-02-13 | 2020-08-20 | Bayer Aktiengesellschaft | Process for the preparation of porous microparticles |
| WO2022057836A1 (zh) * | 2020-09-16 | 2022-03-24 | 南京明德新药研发有限公司 | 苯并脲环衍生物及其制备方法和应用 |
| CN117279923B (zh) * | 2021-04-27 | 2025-09-30 | 南京明德新药研发有限公司 | 六元杂芳并脲环的衍生物及其应用 |
Family Cites Families (8)
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|---|---|---|---|---|
| DE19642255A1 (de) | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| IL129416A0 (en) | 1996-10-14 | 2000-02-17 | Bayer Ag | New heterocyclylmethyl-substituted pyrazol derivatives |
| DE19649460A1 (de) | 1996-11-26 | 1998-05-28 | Bayer Ag | Neue substituierte Pyrazolderivate |
| US6451805B1 (en) | 1997-11-14 | 2002-09-17 | Bayer Aktiengesellschaft | Substituted pyrazole derivatives for the treatment of cardiocirculatory diseases |
| 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 |
| DE19834047A1 (de) * | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834044A1 (de) * | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE19846514A1 (de) | 1998-10-09 | 2000-04-20 | Bayer Ag | Neue Heterocyclyl-methyl-substituierte Pyrazole |
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2001
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- 2001-11-09 US US10/432,740 patent/US6903089B1/en not_active Expired - Fee Related
- 2001-11-09 AU AU2002221827A patent/AU2002221827A1/en not_active Abandoned
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- 2001-11-09 WO PCT/EP2001/012965 patent/WO2002042299A1/de not_active Ceased
- 2001-11-09 ES ES01997487T patent/ES2231581T3/es not_active Expired - Lifetime
- 2001-11-09 EP EP01997487A patent/EP1339716B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1339716A1 (de) | 2003-09-03 |
| WO2002042299A1 (de) | 2002-05-30 |
| JP4295505B2 (ja) | 2009-07-15 |
| CA2429308C (en) | 2010-09-21 |
| EP1339716B1 (de) | 2004-11-03 |
| AU2002221827A1 (en) | 2002-06-03 |
| US6903089B1 (en) | 2005-06-07 |
| JP2004520285A (ja) | 2004-07-08 |
| CA2429308A1 (en) | 2002-05-30 |
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