MX2013005115A - Metodos y compuestos utiles en la sintesis de derivados de aminodihidrotiazina fusionados. - Google Patents
Metodos y compuestos utiles en la sintesis de derivados de aminodihidrotiazina fusionados.Info
- Publication number
- MX2013005115A MX2013005115A MX2013005115A MX2013005115A MX2013005115A MX 2013005115 A MX2013005115 A MX 2013005115A MX 2013005115 A MX2013005115 A MX 2013005115A MX 2013005115 A MX2013005115 A MX 2013005115A MX 2013005115 A MX2013005115 A MX 2013005115A
- Authority
- MX
- Mexico
- Prior art keywords
- further characterized
- compound
- salt
- formula
- mixture
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 240
- 238000000034 method Methods 0.000 title claims abstract description 121
- 230000015572 biosynthetic process Effects 0.000 title description 12
- 238000003786 synthesis reaction Methods 0.000 title description 10
- VNTNANCAPVJRJP-UHFFFAOYSA-N 3,4-dihydrothiazin-2-amine Chemical class NN1CCC=CS1 VNTNANCAPVJRJP-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 188
- -1 hydroxyhethyl Chemical group 0.000 claims description 159
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 124
- 150000003839 salts Chemical class 0.000 claims description 121
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 100
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 86
- 239000011737 fluorine Substances 0.000 claims description 81
- 229910052731 fluorine Inorganic materials 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 80
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 61
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
- 235000019439 ethyl acetate Nutrition 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 36
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 33
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
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- 238000010438 heat treatment Methods 0.000 claims description 27
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 18
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 12
- 239000011874 heated mixture Substances 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 12
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 12
- 150000003738 xylenes Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- 229910052725 zinc Inorganic materials 0.000 claims description 11
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 10
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical group CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 9
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 150000004703 alkoxides Chemical class 0.000 claims description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
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- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 claims description 3
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 claims description 3
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- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
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- 238000010899 nucleation Methods 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- JLPJFSCQKHRSQR-UHFFFAOYSA-N oxolan-3-one Chemical compound O=C1CCOC1 JLPJFSCQKHRSQR-UHFFFAOYSA-N 0.000 description 1
- RZTDESRVPFKCBH-UHFFFAOYSA-N p-Tol-Tol-p Natural products C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 238000010935 polish filtration Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- YOEWQQVKRJEPAE-UHFFFAOYSA-L succinylcholine chloride (anhydrous) Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C YOEWQQVKRJEPAE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- MWUCVUDHOLYUAM-UHFFFAOYSA-N tert-butyl 2-(1,1,1-trifluorobut-3-en-2-yloxy)acetate Chemical compound CC(C)(C)OC(=O)COC(C=C)C(F)(F)F MWUCVUDHOLYUAM-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161434849P | 2011-01-21 | 2011-01-21 | |
| PCT/US2012/022053 WO2012100179A1 (en) | 2011-01-21 | 2012-01-20 | Methods and compounds useful in the synthesis of fused aminodihydrothiazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2013005115A true MX2013005115A (es) | 2013-06-03 |
Family
ID=45563570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2013005115A MX2013005115A (es) | 2011-01-21 | 2012-01-20 | Metodos y compuestos utiles en la sintesis de derivados de aminodihidrotiazina fusionados. |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8426584B2 (enExample) |
| EP (1) | EP2665716B1 (enExample) |
| JP (2) | JP5993875B2 (enExample) |
| CN (2) | CN103502231A (enExample) |
| BR (1) | BR112013016241A2 (enExample) |
| CA (1) | CA2814014A1 (enExample) |
| ES (1) | ES2624288T3 (enExample) |
| IL (1) | IL226405A0 (enExample) |
| MX (1) | MX2013005115A (enExample) |
| RU (1) | RU2013138226A (enExample) |
| SG (2) | SG191710A1 (enExample) |
| WO (1) | WO2012100179A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0906962B8 (pt) | 2008-01-18 | 2021-05-25 | Eisai R&D Man Co Ltd | composto de aminodiidrotiazina fundido |
| GB0912777D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydropyrimidone derivatives |
| GB0912778D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydro-oxazine derivatives |
| GB201100181D0 (en) | 2011-01-06 | 2011-02-23 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101139D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| UY34278A (es) | 2011-08-25 | 2013-04-05 | Novartis Ag | Derivados novedosos de oxazina y su uso en el tratamiento de enfermedades |
| GB201212816D0 (en) * | 2012-07-19 | 2012-09-05 | Eisai Ltd | Novel compounds |
| TWI639607B (zh) | 2013-06-18 | 2018-11-01 | 美國禮來大藥廠 | Ｂａｃｅ抑制劑 |
| CA2963761C (en) * | 2014-10-10 | 2023-10-17 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition of fused aminodihydrothiazine derivative |
| KR102630042B1 (ko) | 2016-10-27 | 2024-01-29 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 알츠하이머병의 치료를 위한 항-a베타 원시섬유 항체 및 베타-세크레타제 bace1 억제제를 포함하는 조성물 |
| WO2020023530A2 (en) | 2018-07-24 | 2020-01-30 | Eisai R&D Management Co., Ltd. | Methods of treatment and prevention of alzheimer's disease |
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|---|---|---|---|---|
| US3235551A (en) | 1966-02-15 | Novel derivatives of | ||
| US3227713A (en) | 1966-01-04 | Azine derivatives | ||
| JPH0967355A (ja) | 1995-08-31 | 1997-03-11 | Tokyo Tanabe Co Ltd | チアジン誘導体、チアゾール誘導体及びそれらの製造方法 |
| AU2001258771A1 (en) | 2000-05-19 | 2001-11-26 | Takeda Chemical Industries Ltd. | -secretase inhibitors |
| US6562783B2 (en) | 2001-05-30 | 2003-05-13 | Neurologic, Inc. | Phosphinylmethyl and phosphorylmethyl succinic and glutauric acid analogs as β-secretase inhibitors |
| AU2003254844A1 (en) | 2002-08-09 | 2004-02-25 | Takeda Chemical Industries, Ltd. | Substituted amino compounds and use thereof |
| AU2003285012A1 (en) | 2002-10-24 | 2004-05-13 | Sepracor, Inc. | Compositions comprising zopiclone derivatives and methods of making and using the same |
| JP2004149429A (ja) | 2002-10-29 | 2004-05-27 | Takeda Chem Ind Ltd | インドール化合物およびその用途 |
| DE60329316D1 (de) | 2002-11-12 | 2009-10-29 | Merck & Co Inc | Phenylcarboxamide als beta-sekretase-hemmer zur behandlung von alzheimer |
| CA2548388A1 (en) | 2003-12-15 | 2005-06-30 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| JP2007530696A (ja) | 2004-03-30 | 2007-11-01 | メルク エンド カムパニー インコーポレーテッド | アスパラギン酸プロテアーゼ阻害剤として有用な２−アミノチアゾール化合物 |
| PE20060664A1 (es) | 2004-09-15 | 2006-08-04 | Novartis Ag | Amidas biciclicas como inhibidores de cinasa |
| CN101084198A (zh) | 2004-10-15 | 2007-12-05 | 阿斯利康(瑞典)有限公司 | 取代的氨基－嘧啶酮及其用途 |
| US20090221579A1 (en) | 2004-10-15 | 2009-09-03 | Jeffrey Scott Albert | Substituted Amino-Compounds and Uses Thereof |
| WO2006078577A1 (en) | 2005-01-19 | 2006-07-27 | Merck & Co., Inc. | Tertiary carbinamines having substituted heterocycles, which are active as inhibitors of beta-secretase, for the treatment of alzheimer's disease |
| WO2006138264A2 (en) | 2005-06-14 | 2006-12-28 | Schering Corporation | Aspartyl protease inhibitors |
| CA2615656A1 (en) | 2005-07-18 | 2007-01-25 | Merck & Co., Inc. | Spiropiperidine beta-secretase inhibitors for the treatment of alzheimer's disease |
| ES2537898T3 (es) | 2005-10-25 | 2015-06-15 | Shionogi & Co., Ltd. | Derivados de aminotiazolidina y aminotetrahidrotiazepina como inhibidores de BACE 1 |
| JP2009532464A (ja) | 2006-04-05 | 2009-09-10 | アストラゼネカ・アクチエボラーグ | ２−アミノピリミジン−４−オン及びＡβ−関連の病理を治療又は予防するためのその使用 |
| JP5117382B2 (ja) | 2006-05-31 | 2013-01-16 | 第一三共株式会社 | ７員環化合物の製造方法 |
| MX2009006228A (es) | 2006-12-12 | 2009-06-22 | Schering Corp | Inhibidores de aspartil proteasa. |
| EP2151435A4 (en) * | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| AU2008245082B8 (en) | 2007-04-24 | 2012-09-13 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives substituted with a cyclic group |
| EP2151436B1 (en) | 2007-05-29 | 2013-04-24 | Santen Pharmaceutical Co., Ltd | Novel 1,2,3,4-tetrahydroquinoxaline derivative which has, as substituent, phenyl group having sulfonic acid ester structure or sulfonic acid amide structure introduced therein and has glucocorticoid receptor-binding activity |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| BRPI0906962B8 (pt) | 2008-01-18 | 2021-05-25 | Eisai R&D Man Co Ltd | composto de aminodiidrotiazina fundido |
| TWI431004B (zh) | 2008-05-02 | 2014-03-21 | Lilly Co Eli | Ｂａｃｅ抑制劑 |
| WO2010013302A1 (ja) | 2008-07-28 | 2010-02-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スピロアミノジヒドロチアジン誘導体 |
| AU2009277485B2 (en) | 2008-07-28 | 2013-05-02 | Eisai R&D Management Co., Ltd. | Spiroaminodihydrothiazine derivatives |
| KR20110076965A (ko) | 2008-09-30 | 2011-07-06 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 신규한 축합 아미노 디하이드로티아진 유도체 |
| AR077277A1 (es) * | 2009-07-09 | 2011-08-17 | Lilly Co Eli | Compuestos de biciclo (1,3)tiazin-2-amina formulacion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para el tratamiento de la enfermedad de alzheimer |
| GB0912778D0 (en) * | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydro-oxazine derivatives |
| GB0912777D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydropyrimidone derivatives |
| MX2012015135A (es) | 2010-07-01 | 2013-05-06 | Amgen Inc | Compuestos heterociclicos y su uso como inhibidores de la actividad pi3k. |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
-
2012
- 2012-01-20 EP EP12702690.4A patent/EP2665716B1/en active Active
- 2012-01-20 CA CA2814014A patent/CA2814014A1/en not_active Abandoned
- 2012-01-20 US US13/355,030 patent/US8426584B2/en not_active Expired - Fee Related
- 2012-01-20 BR BR112013016241A patent/BR112013016241A2/pt not_active IP Right Cessation
- 2012-01-20 SG SG2013027461A patent/SG191710A1/en unknown
- 2012-01-20 RU RU2013138226/04A patent/RU2013138226A/ru not_active Application Discontinuation
- 2012-01-20 SG SG10201601516QA patent/SG10201601516QA/en unknown
- 2012-01-20 MX MX2013005115A patent/MX2013005115A/es active IP Right Grant
- 2012-01-20 JP JP2013550622A patent/JP5993875B2/ja not_active Expired - Fee Related
- 2012-01-20 CN CN201280004193.7A patent/CN103502231A/zh active Pending
- 2012-01-20 CN CN201610875412.9A patent/CN106632401B/zh not_active Expired - Fee Related
- 2012-01-20 WO PCT/US2012/022053 patent/WO2012100179A1/en not_active Ceased
- 2012-01-20 ES ES12702690.4T patent/ES2624288T3/es active Active
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2013
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- 2013-05-16 IL IL226405A patent/IL226405A0/en unknown
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2014
- 2014-06-26 US US14/316,321 patent/US8962858B2/en not_active Expired - Fee Related
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2016
- 2016-03-03 JP JP2016041508A patent/JP6087005B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8802871B2 (en) | 2014-08-12 |
| JP2016121177A (ja) | 2016-07-07 |
| BR112013016241A2 (pt) | 2016-07-12 |
| RU2013138226A (ru) | 2015-02-27 |
| EP2665716B1 (en) | 2017-03-08 |
| CN106632401A (zh) | 2017-05-10 |
| WO2012100179A1 (en) | 2012-07-26 |
| US8426584B2 (en) | 2013-04-23 |
| JP6087005B2 (ja) | 2017-03-01 |
| CA2814014A1 (en) | 2012-07-26 |
| JP2014503001A (ja) | 2014-02-06 |
| ES2624288T3 (es) | 2017-07-13 |
| US20130197244A1 (en) | 2013-08-01 |
| IL226405A0 (en) | 2013-07-31 |
| JP5993875B2 (ja) | 2016-09-14 |
| CN106632401B (zh) | 2020-12-29 |
| US20120190848A1 (en) | 2012-07-26 |
| US20140309429A1 (en) | 2014-10-16 |
| SG191710A1 (en) | 2013-08-30 |
| US8962858B2 (en) | 2015-02-24 |
| EP2665716A1 (en) | 2013-11-27 |
| CN103502231A (zh) | 2014-01-08 |
| SG10201601516QA (en) | 2016-03-30 |
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