TWI711615B - 作為可溶性鳥苷酸環化酶活化劑的雜環羧酸 - Google Patents
作為可溶性鳥苷酸環化酶活化劑的雜環羧酸 Download PDFInfo
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- TWI711615B TWI711615B TW104123596A TW104123596A TWI711615B TW I711615 B TWI711615 B TW I711615B TW 104123596 A TW104123596 A TW 104123596A TW 104123596 A TW104123596 A TW 104123596A TW I711615 B TWI711615 B TW I711615B
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- RWKGYDMSJZUVNO-UHFFFAOYSA-N methyl 5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate Chemical compound C1NCCC2=CC(C(=O)OC)=CN=C21 RWKGYDMSJZUVNO-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
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- ACQUKYSUICAHTK-UHFFFAOYSA-N tert-butyl 2-(bromomethyl)-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC=2C=CC(=NC=2CC1)CBr ACQUKYSUICAHTK-UHFFFAOYSA-N 0.000 description 1
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- UWOVCEFGMXDUDK-UHFFFAOYSA-N tert-butyl 6-(bromomethyl)-5,8-dimethyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CC2=C1C(C)=C(CBr)C=C2C UWOVCEFGMXDUDK-UHFFFAOYSA-N 0.000 description 1
- GTCULBWITFUYOK-UHFFFAOYSA-N tert-butyl 6-(bromomethyl)-8-(methoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC2=C(C=C(C=C2CC1)CBr)COC GTCULBWITFUYOK-UHFFFAOYSA-N 0.000 description 1
- KQAYOFLTZFOGBR-UHFFFAOYSA-N tert-butyl 6-(bromomethyl)-8-methyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CC2=C1C=C(CBr)C=C2C KQAYOFLTZFOGBR-UHFFFAOYSA-N 0.000 description 1
- MVFKSICKPQEITD-UHFFFAOYSA-N tert-butyl 7-(bromomethyl)-6-fluoro-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC2=C(CC1)C(=C(C=C2)CBr)F MVFKSICKPQEITD-UHFFFAOYSA-N 0.000 description 1
- PROWWHWPLUSRKW-UHFFFAOYSA-N tert-butyl 8-(bromomethyl)-6-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC2=C(CC1)C(=CC(=C2)CBr)C PROWWHWPLUSRKW-UHFFFAOYSA-N 0.000 description 1
- IPNBRMXNGHIWSI-UHFFFAOYSA-N tert-butyl 8-(bromomethyl)-6-methyl-3,5-dihydro-2H-1,4-benzoxazepine-4-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCOC2=C(C1)C(=CC(=C2)CBr)C IPNBRMXNGHIWSI-UHFFFAOYSA-N 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- DSPYCWLYGXGJNJ-UHFFFAOYSA-N tert-butyl n-prop-2-ynylcarbamate Chemical compound CC(C)(C)OC(=O)NCC#C DSPYCWLYGXGJNJ-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- YMYHIIMNMWCDJZ-UHFFFAOYSA-N tert-butyl-ethyl-dimethylsilane Chemical compound CC[Si](C)(C)C(C)(C)C YMYHIIMNMWCDJZ-UHFFFAOYSA-N 0.000 description 1
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- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
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- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
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- 230000001960 triggered effect Effects 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
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| KR102456406B1 (ko) | 2016-09-14 | 2022-10-19 | 게노마티카 인코포레이티드 | 1,3-지방 디올 화합물 및 그 유도체 |
| EP3525778A1 (de) | 2016-10-11 | 2019-08-21 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc aktivatoren und mineralocorticoid-rezeptor-antagonisten |
| CN106495999B (zh) * | 2016-10-18 | 2019-08-16 | 亳州学院 | 一种芳香醛及其合成方法 |
| US12491261B2 (en) | 2016-10-26 | 2025-12-09 | Acuitas Therapeutics, Inc. | Lipid nanoparticle formulations |
| CA3069554A1 (en) | 2017-07-14 | 2019-01-17 | Glaxosmithkline Intellectual Property Development Limited | Inhibitors of leucine rich repeat kinase 2 |
| WO2019036000A1 (en) * | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | LIPIDS FOR USE IN LIPID NANOPARTICLE FORMULATIONS |
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| WO2019207517A1 (en) * | 2018-04-27 | 2019-10-31 | Hetero Labs Limited | Process for preparation of ((3r,11br)-1,3,4,6,7,11b-hexahydro-9,10-di(methoxy-d 3)-3-(2-methylpropyl)-2h-benzo[a]quinolizin-2-one |
| JP7314173B2 (ja) | 2018-04-30 | 2023-07-25 | バイエル アクチェンゲゼルシャフト | 認知障害の治療のためのｓＧＣ活性化薬及びｓＧＣ刺激薬の使用 |
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| US12234217B2 (en) | 2018-12-03 | 2025-02-25 | Fmc Corporation | Method for preparing N-phenylpyrazole-1-carboxamides |
| EP3911675A1 (en) | 2019-01-17 | 2021-11-24 | Bayer Aktiengesellschaft | Methods to determine whether a subject is suitable of being treated with an agonist of soluble guanylyl cyclase (sgc) |
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| EP1906957A1 (en) | 2005-07-18 | 2008-04-09 | Bayer HealthCare AG | Novel use of activators and stimulators of soluble guanylate cyclase for the prevention or treatment of renal disorders |
| US20080045560A1 (en) | 2006-08-15 | 2008-02-21 | Wyeth | Pyrrolidine and related derivatives useful as PR modulators |
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| EP2207541B1 (en) | 2007-10-05 | 2014-10-29 | Sanofi-Aventis Deutschland GmbH | Use of sulfonyl-substituted 2-sulfonylaminobenzoic acid n-phenylamides in the treatment of pain |
| WO2009068652A1 (en) | 2007-11-30 | 2009-06-04 | Smithkline Beecham Corporation | 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines as soluble guanylate cyclase activators |
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| AU2009322836B2 (en) | 2008-11-25 | 2013-04-04 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| MA32967B1 (fr) | 2009-01-17 | 2012-01-02 | Bayer Schering Pharma Ag | Stimulateurs sgc d'activateurs sgc en combinaison avec des inhibiteurs pde5 dans le traitement du dysfonctionnement érectile |
| JP5411300B2 (ja) | 2009-02-26 | 2014-02-12 | メルク・シャープ・アンド・ドーム・コーポレーション | 可溶性グアニレートシクラーゼ活性化剤 |
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| RS54336B1 (sr) | 2010-02-05 | 2016-02-29 | Adverio Pharma Gmbh | Sgc stimulatori ili sgc aktivatori, sami za sebe i kombinovani sa pde5 inhibitorima za tretman cistične fibroze |
| ES2549979T3 (es) | 2010-05-26 | 2015-11-03 | Adverio Pharma Gmbh | El uso de estimuladores de la sGC, activadores de la sGC, solos y en combinaciones con inhibidores de la PDE5 para el tratamiento de esclerosis sistémica (EcS) |
| EP2585055A1 (de) | 2010-06-25 | 2013-05-01 | Bayer Intellectual Property GmbH | Verwendung von stimulatoren und aktivatoren der löslichen guanylatzyklase zur behandlung von sichelzellanämie und konservierung von blutersatzstoffen |
| US8895583B2 (en) | 2010-10-28 | 2014-11-25 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| US8569339B2 (en) | 2011-03-10 | 2013-10-29 | Boehringer Ingelheim International Gmbh | Soluble guanylate cyclase activators |
| WO2013025425A1 (en) * | 2011-08-12 | 2013-02-21 | Boehringer Ingelheim International Gmbh | Soluble guanylate cyclase activators |
| 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) |
| DK2892891T3 (da) | 2012-09-07 | 2019-10-14 | Boehringer Ingelheim Int | Alkoxypyrazoler som opløselige guanylatcyklaseaktivatorer |
| WO2015095515A1 (en) | 2013-12-20 | 2015-06-25 | Novartis Ag | Sgc activators for the treatment of glaucoma |
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