AR035347A1 - Compuestos de tiadiazoles y oxadiazoles, proceso de preparacion, composiciones farmaceuticas y uso para la preparacion de composiciones farmaceuticas de los mismos. - Google Patents
Compuestos de tiadiazoles y oxadiazoles, proceso de preparacion, composiciones farmaceuticas y uso para la preparacion de composiciones farmaceuticas de los mismos.Info
- Publication number
- AR035347A1 AR035347A1 ARP010104558A ARP010104558A AR035347A1 AR 035347 A1 AR035347 A1 AR 035347A1 AR P010104558 A ARP010104558 A AR P010104558A AR P010104558 A ARP010104558 A AR P010104558A AR 035347 A1 AR035347 A1 AR 035347A1
- Authority
- AR
- Argentina
- Prior art keywords
- nr9r10
- different
- heterocycle
- same
- lower alkyl
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
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- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Transplantation (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
Compuestos de fórmula (1), donde: Y es O ó S; R1 es: alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo, cicloalquenilo, heterociclo, arilo o un grupo policíclico; cada uno optativamente sustituido con uno o varios grupos X1-R4, idénticos o diferentes, en donde: X1 es: un solo enlace, alquileno inferior, alquenileno C2-6, cicloalquileno, arileno o heterociclo divalente y R4 es: 1) H, =O, NO2, CN, halógeno, haloalquilo inferior, alquilo inferior, bioisóstero de ácido carboxílico, 2) COOR5, C(=O)R5, C(=S)R5, SO2R5, SOR5, SO3R5, SR5, OR5, 3) C(=O)NR7R8, C(=S)NR7R8, C(=N-CN)NR7R8, C(=N-SO2NH2)NR7R8, C(=CH-NO2)NR7R8, C(=NR7)NHR8, C(=NR7)R8, C(=NR9)NHR8, C(=NR9)R8, SO2NR7R8 o NR7R8 en donde R7 y R8 son iguales o diferentes y se seleccionan de OH, R5, R6, C(=O)NR5R6, C(=O)R5, SO2R5, C(=NR9)NHR10, C(=NR9)R10, C(=CH-NO2)NR9R10, C(=N-SO2NH2)NR9R10, C(=N-CN)NR9R10 o C(=S)NR9R10; R2 es: alquilo inferior, alquenilo C2-10, alquinilo C2-10, cicloalquilo, cicloalquenilo, heterociclo, arilo; cada uno optativamente sustituido con uno o varios grupos que son iguales o diferentes y que se seleccionan de: 1) H, bioisóstero de ácido carboxílico, haloalquilo inferior, halógeno, 2) COOR5, OR5, SO2R5, 3) SO2NR11R12, C(=O)NR11R12 o NR11R12 en donde R11 y R12 son iguales o diferentes y se seleccionan de OH, R5, R6, C(=O)NR5R6, C(=O)R5, SO2R5, C(=S)NR9R10, C(=CH-NO2)NR9R10, C(=N-CN)NR9R10, C(=N-SO2NH2)NR9R10, C(=NR9)NHR10 o C(=NR9)R10; R3 es X2-R'3 en donde: X2 es un solo enlace o un grupo seleccionado de alquileno C1-4, alquenileno C2-6, alquinileno C2-6, cada uno optativamente sustituido con uno o varios grupos que son iguales o diferentes y que se seleccionan de: 1) H, alquilo C1-3, cicloalquilo C3-4, arilo, heterociclo, =O, CN, 2) OR5, =NR5 o 3) NR13R14 en donde R13 y R14 son iguales o diferentes y se seleccionan de R5, R6, C(=O)NR5R6, C(=O)R5, SO2R5, C(=S)NR9R10, C(=CH-NO2)NR9R10, C(=NR9)NHR10 o C(=NR9)R10; R'3 es: cicloalquilo, cicloalquenilo, arilo, heterociclo o un grupo policíclico; cada uno optativamente sustituido con uno o varios grupos X3-R17, idénticos o diferentes, en donde: X3 es: un solo enlace, alquileno inferior, alquenileno C2-6, alquinileno C2-6, cicloalquileno, arileno, heterociclo divalente o un grupo heterocíclico divalente y R17 es: 1) H, =O, NO2, CN, haloalquilo inferior, halógeno, bioisóstero de ácido carboxílico, cicloalquilo, 2) COOR5, C(=O)R5, C(=S)R5, SO2R5, SOR5, SO3R5, SR5, OR5, 3) C(=O)NR15R16, C(=S)NR15R16, C(=N-CN)NR15R16, C(=N-SO2NH2)NR15R16, C(=CH-NO2)NR15R16, SO2NR15R16, C(=NR15)NHR16, C(=NR15)R16, C(=NR9)NHR16, C(=NR9)R16 o NR15R16 en donde R15 y R16 son iguales o diferentes y se seleccionan de OH, R5, R6, C(=O)NR5R6, C(=O)R5, SO2R5, C(=S)NR9R10, C(=CH-NO2)NR9R10, C(=N-CN)NR9R10, C(=N-SO2NH2)NR9R10, C(=NR9)NHR10 o C(=NR9)R10, 4) heterociclo optativamente sustituido con uno o varios grupos R5; en donde, R5 y R6 son iguales o diferentes y se seleccionan de: H, alquilo inferior, alquenilo C2-6, alquinilo C2-6, X4-cicloalquilo, X4-cicloalquenilo, X4-arilo, X4-heterociclo o X4-grupo policíclico, en donde X4 es un solo enlace, alquileno inferior o alquenilo de C2-6; cada uno optativamente sustituido con uno o varios grupos que son iguales o diferentes y que se seleccionan de: halógeno, =O, COOR20, CN, OR20, alquilo inferior optativamente sustituido con OR20, O-alquilo inferior optativamente sustituido con OR20, C(=O)-alquilo inferior, haloalquilo inferior, X5-N(R18R19), en donde X5 es un solo enlace o alquileno inferior y R18, R19 y R20 son iguales o diferentes y se seleccionan de H o alquilo inferior; X6-heterociclo, X6-arilo, X6-cicloalquilo, X6-cicloalquenilo, X6-grupo policíclico en donde X6 se selecciona de un solo enlace o alquileno inferior, estos grupos optativamente se sustituyen con uno o varios grupos, idénticos o diferentes, seleccionados de halógenos, COOR21, OR21, o (CH2)nNR21R22 en donde n es 0, 1 ó 2 y R21 y R22 son iguales o diferentes y se seleccionan de H o alquilo inferior; R9 se selecciona de H, CN, OH, alquilo inferior, O-alquilo inferior, arilo, heterociclo, SO2NH2 o X5-N(R18R19) en donde X5 es un solo enlace o alquileno inferior y R18 y R19 son iguales o diferentes y se seleccionan de H o alquilo inferior; R10 se selecciona de hidrógeno, alquilo inferior, ciclopropilo o heterociclo; o un derivado farmacéuticamente aceptable de él, con la condición de que el compuesto de la fórmula (1) no sea etil éster del ácido 4-[2-formilimino-5-(4-metoxi-fenil)-[1,3,4]tiadiazol-3-il]-butírico, etil éster del ácido 4-[5-(4-cloro-fenil)-2-formilimino-[1,3,4]tiadiazol-3-il]-butírico. Composiciones farmacéuticas que comprende un compuesto de la fórmula (1) y un vehículo farmacéuticamente aceptable. El uso de dichos compuestos para fabricar un medicamento útil para tratamiento con inhibidores selectivos de fosfodiesterasa-7 (PDE7), enfermedades relacionadas con células T, autoinmunes, inflamatorias, respiratorias, del sistema nervioso central (CNS), alérgicas, endócrinas o exócrinas del páncreas, gastrointestinales, dolor visceral, inflamatoria del intestino, osteoartritis, esclerosis múltiple, pulmonar obstructiva crónica (COPD), asma, cáncer, síndrome de inmunodeficiencia adquirida (SIDA) o rechazo de trasplantes. Proceso para preparar los compuestos de la fórmula (1) que comprende reacción de una hidracina de S2C y MeX, reacción con cloruro de acilo, ciclación y reacción con amina R1NH2. Los compuestos son inhibidores selectivos de PDE7, activos a concentraciones micromolares o preferentemente nanomolares.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00402710A EP1193261A1 (en) | 2000-10-02 | 2000-10-02 | New thiadiazoles and their use as phosphodiesterase-7 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035347A1 true AR035347A1 (es) | 2004-05-12 |
Family
ID=8173891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010104558A AR035347A1 (es) | 2000-10-02 | 2001-09-27 | Compuestos de tiadiazoles y oxadiazoles, proceso de preparacion, composiciones farmaceuticas y uso para la preparacion de composiciones farmaceuticas de los mismos. |
Country Status (43)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1597385A1 (en) * | 2002-11-13 | 2005-11-23 | Bayer HealthCare AG | DIAGNOSTICS AND THERAPEUTICS FOR DISEASES ASSOCIATED WITH HUMAN PHOSPHODIESTERASE 7A1 (PDE7a1) |
| ES2217956B1 (es) * | 2003-01-23 | 2006-04-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| JP2006219374A (ja) | 2003-06-13 | 2006-08-24 | Daiichi Asubio Pharma Co Ltd | Ｐｄｅ７阻害作用を有するイミダゾトリアジノン誘導体 |
| JP2006219373A (ja) | 2003-06-13 | 2006-08-24 | Daiichi Asubio Pharma Co Ltd | Ｐｄｅ７阻害作用を有するピリジニルピラゾロピリミジノン誘導体 |
| JP4810426B2 (ja) | 2004-07-01 | 2011-11-09 | 第一三共株式会社 | Ｐｄｅ７阻害作用を有するチエノピラゾール誘導体 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| US7985756B2 (en) | 2005-10-21 | 2011-07-26 | Braincells Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| JP2009536669A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス，インコーポレイティド | アンジオテンシン調節による神経新生 |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| JP2010502722A (ja) | 2006-09-08 | 2010-01-28 | ブレインセルス，インコーポレイティド | ４−アシルアミノピリジン誘導体を含む組み合わせ |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| CA2681650C (en) * | 2007-03-27 | 2016-11-22 | Omeros Corporation | The use of pde7 inhibitors for the treatment of movement disorders |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| MD3995C2 (ro) * | 2009-05-11 | 2010-07-31 | Государственный Университет Молд0 | Utilizare a di(µ-Ofenoxi)-di{[2-(4-aminobenzensulfamido)-5-etil-1,3,4-tiadiazol]-3,5-dibromosalicilidentiosemicarbazonato(-1)-cupru} în calitate de inhibitor al proliferării celulelor T-47D ale cancerului mamar |
| US8703768B2 (en) | 2010-06-09 | 2014-04-22 | Hoffmann-La Roche Inc. | Nitrogen containing heteroaryl compounds |
| RU2661410C2 (ru) | 2010-11-08 | 2018-07-16 | Омерос Корпорейшн | Лечение зависимости и расстройства побуждений с применением ингибиторов фдэ7 |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| CN102276625B (zh) * | 2011-08-24 | 2013-07-17 | 天津药物研究院 | 噻二唑衍生物 |
| EP2804603A1 (en) | 2012-01-10 | 2014-11-26 | President and Fellows of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| CN103288777A (zh) * | 2013-05-28 | 2013-09-11 | 浙江禾田化工有限公司 | 特丁噻草隆关键中间体2-甲基氨基-5-叔丁基-1,3,4-噻二唑的合成方法 |
| US9416652B2 (en) | 2013-08-08 | 2016-08-16 | Vetco Gray Inc. | Sensing magnetized portions of a wellhead system to monitor fatigue loading |
| CN107849611A (zh) * | 2015-06-12 | 2018-03-27 | 奥瑞泽恩基因组学股份有限公司 | 与lsd1抑制剂相关的生物标志物及其用途 |
| CN107674042B (zh) * | 2017-09-28 | 2020-09-25 | 河南科技大学 | 一种超声波无溶剂合成噻二唑类化合物的方法 |
| CN113480486B (zh) * | 2021-07-30 | 2022-05-24 | 赣南师范大学 | 一种3-胺基-1,2,4-三唑类衍生物及其制备方法和应用 |
| WO2024038090A1 (en) | 2022-08-18 | 2024-02-22 | Mitodicure Gmbh | Use of substituted benzoxazole and benzofuran compounds for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exertional intolerance |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE251979C (es) | ||||
| FR2388806A1 (fr) | 1977-04-25 | 1978-11-24 | Gulf Oil Corp | Nouvelles 3-benzyl-2-methylimino-5-phenyl4-1,3,4 thiadiazolines et leur application au desherbage chimique de cultures |
| DK270880A (da) | 1979-07-09 | 1981-01-10 | Gulf Oil Corp | Phenyliminothiadiazolidiner deres fremstilling og anvendelse i plantevaekstregulerende midler |
| DD247003A1 (de) * | 1985-11-07 | 1987-06-24 | Hydrierwerk Rodleben Veb | Verfahren zur herstellung von in 2-stellung mit amninhaltigen gruppen subst. 7 h-1,3,4-thiadiazolo(3,2-a)pyrimidinen |
| DD251979A1 (de) * | 1986-08-01 | 1987-12-02 | Neubauer T Paedagog Hochschule | Verfahren zur herstellung von s-triazinylsubstituierten 2-imino-1,3,4-oxadiazolinen |
| DE4418066A1 (de) | 1994-05-24 | 1995-11-30 | Bayer Ag | Substituierte Thiadiazoline |
| DE69909592T4 (de) * | 1998-02-17 | 2005-03-24 | Roche Diagnostics Gmbh | Verwendung von thiadiazolo[4,3-a]pyridine derivaten |
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2000
- 2000-10-02 EP EP00402710A patent/EP1193261A1/en not_active Withdrawn
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2001
- 2001-09-19 SV SV2001000633A patent/SV2003000633A/es not_active Application Discontinuation
- 2001-09-26 TN TNTNSN01139A patent/TNSN01139A1/en unknown
- 2001-09-27 PE PE2001000964A patent/PE20020419A1/es not_active Application Discontinuation
- 2001-09-27 GT GT200100196A patent/GT200100196A/es unknown
- 2001-09-27 AR ARP010104558A patent/AR035347A1/es unknown
- 2001-09-27 HN HN2001000217A patent/HN2001000217A/es unknown
- 2001-09-27 PA PA20018529501A patent/PA8529501A1/es unknown
- 2001-10-01 BR BR0114391-3A patent/BR0114391A/pt not_active IP Right Cessation
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