WO2016037592A1 - 一种氨基磺酰基类化合物、其制备方法及用途 - Google Patents
一种氨基磺酰基类化合物、其制备方法及用途 Download PDFInfo
- Publication number
- WO2016037592A1 WO2016037592A1 PCT/CN2015/089471 CN2015089471W WO2016037592A1 WO 2016037592 A1 WO2016037592 A1 WO 2016037592A1 CN 2015089471 W CN2015089471 W CN 2015089471W WO 2016037592 A1 WO2016037592 A1 WO 2016037592A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- methyl
- formula
- alkyl
- Prior art date
Links
- 0 CC1*(C)*CC1CI Chemical compound CC1*(C)*CC1CI 0.000 description 2
- KBWHYRUAHXHHFO-UHFFFAOYSA-N BrCc1c[s]cc1 Chemical compound BrCc1c[s]cc1 KBWHYRUAHXHHFO-UHFFFAOYSA-N 0.000 description 1
- OXZHQCUHCSUIBY-UHFFFAOYSA-N CC(C)(C)OC(N(Cc1c[s]cc1)S(N)(=O)=O)=O Chemical compound CC(C)(C)OC(N(Cc1c[s]cc1)S(N)(=O)=O)=O OXZHQCUHCSUIBY-UHFFFAOYSA-N 0.000 description 1
- ZFGUXFGWKAZTDV-UHFFFAOYSA-N CC(C)(C)OC(NS(NCc1n[o]c2ccccc12)(=O)=O)=O Chemical compound CC(C)(C)OC(NS(NCc1n[o]c2ccccc12)(=O)=O)=O ZFGUXFGWKAZTDV-UHFFFAOYSA-N 0.000 description 1
- NJPJEUXBRLCEDZ-UHFFFAOYSA-N NCc1n[o]c2ccccc12 Chemical compound NCc1n[o]c2ccccc12 NJPJEUXBRLCEDZ-UHFFFAOYSA-N 0.000 description 1
- BIYRLLYJHRZROI-UHFFFAOYSA-N NS(NCc1c[s]cc1)(=O)=O Chemical compound NS(NCc1c[s]cc1)(=O)=O BIYRLLYJHRZROI-UHFFFAOYSA-N 0.000 description 1
- QCDAJRYSJYWUFX-UHFFFAOYSA-N NS(NCc1n[o]c2ccccc12)(=O)=O Chemical compound NS(NCc1n[o]c2ccccc12)(=O)=O QCDAJRYSJYWUFX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
Claims (10)
- 一种通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐:X为O、S、NH或CH2,Y为N或CH,当X为O或S时,若Q为苯环,则Y不为CH;Z为N-R5、O或CHR5,当X为O并且Y为N时,Z不为O或CH2;Q环为6~10元芳环,或含1~4个选自N、O、S中的杂原子的5~6元杂环或杂芳环,或者Q环不存在;m为0~4的整数;n为0至2的整数;p为1~2的整数;R1各自独立地为氢、氨基、卤素、三氟甲基、羟基、硝基、腈基、巯基、羧基、醛基、氧代(=O)基团、硫代(=S)基团、C1~C10烷基、C2~C10烯基、C2~C10炔基、C3~C10环烷基、C1~C10烷氧基、C1~C10烷酰基、C1~C10烷氧羰基、C1~C10烷酰氧基、-NR6R7、-CONR6R7、-OCONR6R7、C1~C10硫烷基、磺酸基、氨基甲酰基、磺酰基、C6~C10芳基、含1~4个选自N、O、S中的杂原子的4~10元杂环基、或含1~4个选自N、O、S中的杂原子的4~10元杂芳基;上述氨基、C1~C10烷氧基、C1~C10烷基、C1~C10烷酰基、C1~C10烷氧羰基、C1~C10烷酰氧基、磺酰基、C6~C10芳基、含1~4个选自N、O、S中的杂原子的4~10元杂环基或含1~4个选自N、O、S中的杂原子的4~10元杂芳基可任选地被一个或多个选自卤素、三氟甲基、羟基、硝基、氨基、腈基、羧基、醛基、C1~C10烷基、C1~C10烷氧基、C1~C10烷酰氧基、C1~C10烷氧羰基、C1~C10烷酰基、磺酰基、C1~C10烷磺酰基、苯基和苯甲基中的取代基取代;R2各自独立地为氢、氨基、卤素、三氟甲基、羟基、硝基、腈基、巯基、羧基、醛基、C1~C10烷基、C2~C10烯基、C2~C10炔基、C3~C10环烷基、C1~C10烷氧基、C1~C10烷酰基、C1~C10烷氧羰基、C1~C10烷酰氧基、-NR6R7、-CONR6R7、-OCONR6R7、C1~C10硫烷基、磺酸基、氨基甲酰基、磺酰基、C6~C10芳基、含1~4个选自N、O、S中的杂原子的4~10元杂环基、或含1~4个选自N、O、S中的杂原子的4~10元杂芳基;上述氨基、C1~C10烷氧基、C1~C10烷基、C1~C10烷酰基、C1~C10烷氧羰基、C1~C10烷酰氧基、磺酰基、C6~C10芳基、4~10元杂环基或4~10元杂芳基可任选地被一个或多个选自卤素、三氟甲基、羟基、硝基、氨基、腈基、羧基、醛基、C1~C10烷基、C1~C10烷氧基、C1~C10烷酰氧基、C1~C10烷氧羰基、C1~C10烷酰基、磺酰基、C1~C10烷磺酰基、苯基和苯甲基中的取代基取代;R3和R4各自独立地为H、氨基、三氟甲基、羟基、羧基、醛基、氨基、C1~C10烷基、C2~C10烯基、C2~C10炔基、C3~C10环烷基、C1~C10烷氧基、C1~C10烷氧羰基、C1~C10烷酰基、C1~C10烷酰氧基、磺酰基、C6~C10芳基、含1~4个选自N、O、S中的杂原子的4~10元杂环基、或含1~4个选自N、O、S中的杂原子的4~10元杂芳基;上述氨基、C1~C10烷基、C1~C10烷氧基、C1~C10烷氧羰基、C1~C10烷酰基、C1~C10烷酰氧基、磺酰基、C6~C10芳基、含1~4个选自N、O、S中的杂原子的4~10元杂环基或含1~4个选自N、O、S中的杂原子的4~10元杂芳基可任选地被一个或多个选自卤素、三氟甲基、羟基、硝基、氨基、腈基、羧基、醛基、C1~C10烷基、C1~C10烷氧基、C1~C10烷酰氧基、C1~C10烷氧羰基、C1~C10烷酰基、磺酰基、C1~C10烷磺酰基、苯基和苯甲基中的取代基取代;或R3与R4与跟其相连的N原子一起形成含1~4个选自N、S、O中的杂原子的4~8元杂环基或形成含1~4个选自N、S、O中的杂原子的4~8元杂芳基;R5为H或C1~C10烷基;R6和R7各自独立地为H或C1~C10烷基,或R6与R7与其相连的N原子一起形成含1~4个选自N、S、O中的杂原子的4~8元杂环基或形成含1~4个选自N、S、O中的杂原子的4~8元杂芳基。
- 根据权利要求1所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐,其中,Q环为苯环、含1~2个选自N、O、S中的杂原子的5~6元杂环或杂芳环,或者Q环不存在;m为0、1或2;n为0或1。
- 根据权利要求1所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐,其中,Z为O或N-R5;m为0、1或2;n为0或1;p为1;R1各自独立地为氢、卤素、三氟甲基、羟基、硝基、腈基、巯基、羧基、醛基、C1~C8烷基、C2~C8烯基、C2~C8炔基、C3~C8环烷基、C1~C8烷氧基、C1~C8烷酰基、C1~C8烷氧羰基、C1~C8烷酰氧基、-NR6R7、-CONR6R7、-OCONR6R7、C1~C8硫烷基、磺酰氨基、氨基甲酰基、磺酰基、C1~C8烷基磺酰基、C6~C10芳基、含1~3个选自N、O、S中的杂原子的4~10元杂环基或4~10元杂芳基;R2各自独立地为氢、卤素、三氟甲基、羟基、硝基、腈基、氨基、巯基、羧基、醛基、C1~C8烷基、C2~C8烯基、C2~C8炔基、C3~C8环烷基、C1~C8烷氧基、C1~C8烷酰基、C1~C8烷氧羰基、C1~C8烷酰氧基、-NR6R7、CONR6R7、-OCONR6R7、C1~C8硫烷基、磺酸基、磺酰氨基、氨基甲酰基、磺酰基、C1~C8烷基磺酰基、C6~C10芳基、含1~3个选自N、O、S中的杂原子的4~10元杂环基、或含1~3个选自N、O、S中的杂原子的4~10元杂芳基;R3和R4各自独立地为H或C1~C8烷基或5~6元杂芳基;或R3与R4与跟其相连的N原子一起形成含1~3个选自N、S、O中的杂原子的5~7元杂环基或形成含1~3个选自N、S、O中的杂原子的5~7元杂芳基;R5为H或C1~C3烷基;R6和R7各自独立地为H或C1~C8烷基,或R6与R7与其相连的N原子一起形成含1~3个选自N、S、O中的杂原子的5~7元杂环基或形成含1~3个选自N、S、O中的杂原子的5~7元杂芳基。
- 根据权利要求1所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐,其中,X为O、S或NH;Y为N或CH,且当X为O或S时,Y不为CH;Z为O或N-R5,且当X为O并且Y为N时,Z不为O或CH2;Q为苯环;m为0、1或2;n为0或1;p为1;R1为H、F、Cl、NO2、NH2、NHCOCH3或甲氧基;R2为H或甲基;R3和R4各自独立地为H、甲基、乙基或咪唑基;R5为H;R6和R7各自独立地为H或甲基。
- 根据权利要求1所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐,其中,所述通式I所示的氨基磺酰基类化合物为如下化合物:N-[(6-氯-苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(6-氟-苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(苯并异噻唑-3-基)甲基]-氨基磺酰胺;N-[(苯并异噁唑-3-基)甲基]-N’-甲基-氨基磺酰胺;N-[(苯并异噁唑-3-基)甲基]-N’,N’-二甲基-氨基磺酰胺;1-(苯并异噻唑-3-基)-甲氧基磺酰胺;N-[(6-氟-苯并吡唑-3-基)甲基]-氨基磺酰胺;N-[(5-甲氧基-苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(5-硝基-苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(5-氯-苯并异噁唑-3-基)甲基]-氨基磺酰胺;N-[(噻吩-3-基)甲基]-氨基磺酰胺;N-[(噻吩并[3,2-b]噻吩-3-基)甲基]-氨基磺酰胺;或N-[(2-氯-噻吩-3-基)甲基]-氨基磺酰胺。
- 一种根据权利要求1所述的通式I所示的氨基磺酰基类化合物的制备方法,所述通式I所示的氨基磺酰基类化合物通过如下方法之一制备:(1)当Z为NH时1)由溴代物II与保护基保护的氨基磺酰胺化合物VI经磺酰化、脱保护、胺化反应制备:其中,化合物II与化合物VI在碱存在下通过磺酰化反应得到化合物II-1,其中R8为保护基;在酸性条件下脱去保护基R8;胺化反应由R3-A、R4-A或A-R3-R4-B,与化合物I-1在碱存在的条件下通过胺化反应得到化合物I-2,其中A和B相同或不同,并且分别独立地为Cl、Br或I;或者2)化合物III与保护基保护的氨基磺酰氯VII经磺酰化、脱保护、胺化反应制备化合物I-2:其中,化合物III与化合物VII在碱催化下通过磺酰化反应得到化合物III-1,其中R8为保护基;化合物III-1在酸催化条件下通过脱保护反应得到化合物I-1;卤代烷R3-A、R4-A或A-R3-R4-B,在碱存在条件下与化合物I-1通过胺化反应得到化合物I-2,其中A和B相同或不同,并且分别独立地为Cl、Br或I;(2)当Z为O时化合物IV与化合物VII在碱的存在下通过磺酰化反应得到化合物IV-1,其中R8为保护基;或者在碱存在的条件下,化合物IV与氨基磺酰氯化合物VIII反应直接得到化合物I-3;化合物I-3在碱的存在下再通过胺化反应得到化合物I-4;(3)当Z为CH2时化合物V与HNR3R4经胺化反应制备得到化合物I-5;(4)当Z为N-R5或CH-R5时,由相应的通式I-2或通式I-5所示的化合物经烷基化反应制备得到,其中,X、Y、Q环、m、n、p、R1和R2与权利要求1中的定义相同;R3和R4除不为氢外,与权利要求1中的定义相同;R5为C1~C10烷基。
- 一种药物组合物,其包含治疗有效量的选自根据权利要求1至7中任一项所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体,或其药学上可接受的盐中的一种或多种以及药学上可接受的载体。
- 根据权利要求1至7中任一项所述的通式I所示的氨基磺酰基类化合物或其互变异构体、对映体、消旋体、或其药学上可接受的盐在制备用于治疗惊厥、癫痫、肥胖的疾病的药物中的用途。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201580042722.6A CN106687449B (zh) | 2014-09-12 | 2015-09-11 | 一种氨基磺酰基类化合物、其制备方法及用途 |
KR1020177007934A KR101941794B1 (ko) | 2014-09-12 | 2015-09-11 | 아미노설포닐계 화합물, 이의 제조 방법 및 용도 |
EP15840920.1A EP3192792B1 (en) | 2014-09-12 | 2015-09-11 | Aminosulfonyl-based compounds, preparation method therefor and use thereof |
JP2017514550A JP6454413B2 (ja) | 2014-09-12 | 2015-09-11 | アミノスルホニル系化合物、その製造方法、および使用 |
US15/509,796 US10093679B2 (en) | 2014-09-12 | 2015-09-11 | Amino sulfonyl-based compounds, the preparation method therefor and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410466628.0A CN105399697A (zh) | 2014-09-12 | 2014-09-12 | 一种氨基磺酰基类化合物、其制备方法及用途 |
CN201410466628.0 | 2014-09-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2016037592A1 true WO2016037592A1 (zh) | 2016-03-17 |
Family
ID=55458364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2015/089471 WO2016037592A1 (zh) | 2014-09-12 | 2015-09-11 | 一种氨基磺酰基类化合物、其制备方法及用途 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10093679B2 (zh) |
EP (1) | EP3192792B1 (zh) |
JP (1) | JP6454413B2 (zh) |
KR (1) | KR101941794B1 (zh) |
CN (2) | CN105399697A (zh) |
WO (1) | WO2016037592A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111925308A (zh) * | 2020-08-13 | 2020-11-13 | 广西民族大学 | 一种光催化合成n-取代砜二亚胺的方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106543095B (zh) * | 2016-09-23 | 2019-03-05 | 江苏大学 | 一种基于2-羟基苯乙酮肟及其衍生物一锅制备苯并异噁唑的方法 |
CN113651767B (zh) * | 2021-09-18 | 2023-06-09 | 江西中医药大学 | 一种苯并异噁唑类杂环化合物及其制备方法和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007095608A2 (en) * | 2006-02-15 | 2007-08-23 | Janssen Pharmaceutical, N.V. | Use of benzo-heteroaryl sulfamide derivatives for the treatment of disease modification of epileptogenesis |
CN101090896A (zh) * | 2004-08-24 | 2007-12-19 | 詹森药业有限公司 | 用作抗惊厥药的新的苯并稠合杂芳基氨基磺酰胺衍生物 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6033114B2 (ja) * | 1976-12-16 | 1985-08-01 | 大日本製薬株式会社 | 1,2−ベンズイソキサゾ−ル誘導体 |
DE3514696A1 (de) * | 1985-04-24 | 1986-11-06 | Bayer Ag, 5090 Leverkusen | N-indolylethyl-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung |
US6979686B1 (en) * | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
JP2000103782A (ja) * | 1998-07-31 | 2000-04-11 | Kyorin Pharmaceut Co Ltd | 環状アミン誘導体及びその製造方法 |
GB0321003D0 (en) * | 2003-09-09 | 2003-10-08 | Angeletti P Ist Richerche Bio | Compounds, compositions and uses |
US7429611B2 (en) * | 2004-09-23 | 2008-09-30 | Bristol-Myers Squibb Company | Indole inhibitors of 15-lipoxygenase |
EP1911747A1 (en) * | 2006-10-11 | 2008-04-16 | Laboratorios del Dr. Esteve S.A. | Sulfonamide substituted pyrazoline compounds, their preparation and use as CB1 modulators |
US20130253022A1 (en) * | 2010-11-30 | 2013-09-26 | Fox Chase Chemical Diversity Center, Inc. | Novel fluorinated sulfamides exhibiting neuroprotective action and their method of use |
-
2014
- 2014-09-12 CN CN201410466628.0A patent/CN105399697A/zh active Pending
-
2015
- 2015-09-11 WO PCT/CN2015/089471 patent/WO2016037592A1/zh active Application Filing
- 2015-09-11 US US15/509,796 patent/US10093679B2/en active Active
- 2015-09-11 KR KR1020177007934A patent/KR101941794B1/ko active IP Right Grant
- 2015-09-11 CN CN201580042722.6A patent/CN106687449B/zh active Active
- 2015-09-11 JP JP2017514550A patent/JP6454413B2/ja active Active
- 2015-09-11 EP EP15840920.1A patent/EP3192792B1/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101090896A (zh) * | 2004-08-24 | 2007-12-19 | 詹森药业有限公司 | 用作抗惊厥药的新的苯并稠合杂芳基氨基磺酰胺衍生物 |
WO2007095608A2 (en) * | 2006-02-15 | 2007-08-23 | Janssen Pharmaceutical, N.V. | Use of benzo-heteroaryl sulfamide derivatives for the treatment of disease modification of epileptogenesis |
Non-Patent Citations (4)
Title |
---|
LEE J.S. ET AL.: "Intramolecular Sulfamylation Reaction of N-(IH-indol-3-yl)ethylsulfamides: Synthesis of 2,3,4,9-Tetrahydro-1, 2-thiazino[5, 6-b]indole 1, 1-Dioxides", BULL KOREAN CHEM. SOC., vol. 09, no. 24, 31 December 2003 (2003-12-31), pages 1399 - 1402, XP055418127 * |
PARKER M. H. ET AL.: "Novel, Broad-Spectrum Anticonvulsants Containing a Sulfamide Group: Advancement of N-«Benzo[b]thien-3-yl)methyl)sulfamide (JNJ-26990990) into Human Clinical Studies", J. MED. CHEM., vol. 52, no. 23, 23 April 2009 (2009-04-23), pages 7528 - 7536, XP055418125 * |
PEDRAS M. S. C. ET AL.: "Toward the control of Leptosphaeria maculans: Design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin", BIORG. MED.CHEM., vol. 14, 17 April 2006 (2006-04-17), pages 4958 - 4979, XP027992764, DOI: doi:10.1016/j.bmc.2006.03.014 * |
See also references of EP3192792A4 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111925308A (zh) * | 2020-08-13 | 2020-11-13 | 广西民族大学 | 一种光催化合成n-取代砜二亚胺的方法 |
CN111925308B (zh) * | 2020-08-13 | 2022-03-22 | 广西民族大学 | 一种光催化合成n-取代砜二亚胺的方法 |
Also Published As
Publication number | Publication date |
---|---|
EP3192792B1 (en) | 2022-03-09 |
JP6454413B2 (ja) | 2019-01-16 |
KR101941794B1 (ko) | 2019-01-23 |
CN106687449A (zh) | 2017-05-17 |
CN106687449B (zh) | 2019-04-09 |
KR20170067728A (ko) | 2017-06-16 |
US20170298080A1 (en) | 2017-10-19 |
CN105399697A (zh) | 2016-03-16 |
EP3192792A4 (en) | 2018-05-30 |
US10093679B2 (en) | 2018-10-09 |
EP3192792A1 (en) | 2017-07-19 |
JP2017530958A (ja) | 2017-10-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2009331179B2 (en) | Novel bicyclic heterocyclic compound | |
CA2409715C (en) | .beta.-carboline derivatives useful as inhibitors of phosphodiesterase | |
CN105324362A (zh) | Ido抑制剂 | |
AU2005236055A1 (en) | Substituted thiazole and pyrimidine derivatives as melanocortin receptor modulators | |
SG182146A1 (en) | Inhibitors of protein tyrosine kinase activity | |
CA2633760A1 (en) | Anti-viral compounds | |
WO2001027105A1 (fr) | Composes de pyrimidine-5-carboxamide, procede de preparation et d'utilisation desdits composes | |
JP6250674B2 (ja) | N型カルシウムチャネル遮断剤としてのピロロピラゾール | |
BR112020000564A2 (pt) | novos derivados de heteroarilamida como inibidores seletivos das histonas desacetilases 1 e/ou 2 (hdac1-2) | |
WO2021052501A1 (zh) | 杂环酰胺类化合物、其可药用的盐及其制备方法和用途 | |
CA3095451A1 (en) | Ox2r compounds | |
EP2968331A1 (en) | Pyrimidine compounds as kinase inhibitors | |
JP4717210B2 (ja) | 男性の勃起機能障害の処置のための5−ヘテロシクリルピラゾロ[4,3−d]ピリミジン−7−オン | |
CA2700113A1 (en) | Indazole acrylic acid amide compound | |
WO2016037592A1 (zh) | 一种氨基磺酰基类化合物、其制备方法及用途 | |
WO2018028491A1 (zh) | 吲哚胺2,3-双加氧酶抑制剂及其在药学中的用途 | |
JP6867998B2 (ja) | ガンを処置するのに使用するための置換疎水性ベンゼンスルホンアミドチアゾール化合物 | |
US10526363B2 (en) | Substituted phosphoramidate compounds and uses thereof | |
CA3178647A1 (en) | Substituted tricyclic amides, analogues thereof, and methods using same | |
JP2019510053A (ja) | シクロフィリンの阻害のための化合物及びその使用 | |
WO2017008681A1 (zh) | 酰胺类衍生物、其制备方法及其在医药上的用途 | |
AU2004201386B2 (en) | 5-heterocyclyl pyrazolo[4,3-d]pyrimidin-7-ones for the treatment of male erectile dysfunction | |
JP2023503091A (ja) | Trpv4受容体リガンド | |
CA3178447A1 (en) | N-heteroarylalkyl-2-(heterocyclyl and heterocyclylmethyl) acetamide derivatives as sstr4 agonists | |
EP2784065B1 (en) | Glycine reuptake inhibitor and use thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 15840920 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15509796 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2017514550 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20177007934 Country of ref document: KR Kind code of ref document: A |
|
REEP | Request for entry into the european phase |
Ref document number: 2015840920 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2015840920 Country of ref document: EP |