HRP20120368A2 - Postupci sinteze spiro-oksindolskih spojeva - Google Patents
Postupci sinteze spiro-oksindolskih spojeva Download PDFInfo
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- HRP20120368A2 HRP20120368A2 HRP20120368AA HRP20120368A HRP20120368A2 HR P20120368 A2 HRP20120368 A2 HR P20120368A2 HR P20120368A A HRP20120368A A HR P20120368AA HR P20120368 A HRP20120368 A HR P20120368A HR P20120368 A2 HRP20120368 A2 HR P20120368A2
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- 238000010189 synthetic method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 79
- 230000008569 process Effects 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims description 212
- 150000003839 salts Chemical class 0.000 claims description 100
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 10
- 239000007818 Grignard reagent Substances 0.000 claims description 7
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 15
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- 239000012071 phase Substances 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
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- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
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- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 7
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 238000004296 chiral HPLC Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229960004198 guanidine Drugs 0.000 description 5
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- 208000004296 neuralgia Diseases 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine group Chemical group N[C@H](CCCCN)C(=O)O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 4
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 230000004941 influx Effects 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- KICNGTSGLUFGHH-UHFFFAOYSA-N spiro[1h-indole-3,7'-6h-furo[2,3-f][1,3]benzodioxole]-2-one Chemical compound C1OC2=CC=3OCOC=3C=C2C21C1=CC=CC=C1NC2=O KICNGTSGLUFGHH-UHFFFAOYSA-N 0.000 description 3
- IKLODGBPSWONQT-UHFFFAOYSA-N spiro[1h-indole-3,8'-3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine]-2-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2NC1=O IKLODGBPSWONQT-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
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| US25133509P | 2009-10-14 | 2009-10-14 | |
| PCT/US2010/052704 WO2011047174A1 (en) | 2009-10-14 | 2010-10-14 | Synthetic methods for spiro-oxindole compounds |
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| HRP20120368A2 true HRP20120368A2 (hr) | 2012-06-30 |
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| HRP20140486AT HRP20140486T1 (hr) | 2009-10-14 | 2014-05-29 | Postupci sinteze spojeva spirooksindola |
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| JP (3) | JP5752136B2 (ja) |
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| CN (1) | CN102753556B (ja) |
| AU (2) | AU2010306768B2 (ja) |
| BR (1) | BR112012008993A2 (ja) |
| CA (1) | CA2777543A1 (ja) |
| CL (3) | CL2012000953A1 (ja) |
| CO (1) | CO6531444A2 (ja) |
| EC (1) | ECSP12011815A (ja) |
| ES (1) | ES2467166T3 (ja) |
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| MY (2) | MY165579A (ja) |
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| WO (1) | WO2011047174A1 (ja) |
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