KR20130089157A - 신규 방법 - Google Patents
신규 방법 Download PDFInfo
- Publication number
- KR20130089157A KR20130089157A KR20127032795A KR20127032795A KR20130089157A KR 20130089157 A KR20130089157 A KR 20130089157A KR 20127032795 A KR20127032795 A KR 20127032795A KR 20127032795 A KR20127032795 A KR 20127032795A KR 20130089157 A KR20130089157 A KR 20130089157A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- preparing
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- -1 alkyl 2-oxocyclopentanecarboxylate Chemical compound 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000003567 thiocyanates Chemical class 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 7
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 4
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- YONAGTZTYKICLQ-UHFFFAOYSA-N 2-(4-oxo-2-sulfanylidene-6,7-dihydro-5h-cyclopenta[d]pyrimidin-1-yl)acetic acid Chemical compound O=C1NC(=S)N(CC(=O)O)C2=C1CCC2 YONAGTZTYKICLQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 0 *COC(C(CCC1)=C1NCC(O)=O)=O Chemical compound *COC(C(CCC1)=C1NCC(O)=O)=O 0.000 description 2
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 2
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 2
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- CQBYREFQWDUSJY-UHFFFAOYSA-N n',n'-diethyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCN(CC)CC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 CQBYREFQWDUSJY-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- UKIMKMRBLRDSCX-UHFFFAOYSA-M sodium;2-[(2-methoxycarbonylcyclopenten-1-yl)amino]acetate Chemical compound [Na+].COC(=O)C1=C(NCC([O-])=O)CCC1 UKIMKMRBLRDSCX-UHFFFAOYSA-M 0.000 description 2
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
- DJGRXBDYBUKPOC-UHFFFAOYSA-N 2-[2-[(4-fluorophenyl)methylsulfanyl]-4-oxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-1-yl]acetic acid Chemical compound OC(=O)CN1C=2CCCC=2C(=O)N=C1SCC1=CC=C(F)C=C1 DJGRXBDYBUKPOC-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 description 1
- HIMSXOOFWOOYFK-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]benzaldehyde Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C=O)C=C1 HIMSXOOFWOOYFK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PZBBESSUKAHBHD-UHFFFAOYSA-N methyl 2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1CCCC1=O PZBBESSUKAHBHD-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000009862 primary prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 230000009863 secondary prevention Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34522410P | 2010-05-17 | 2010-05-17 | |
| US61/345,224 | 2010-05-17 | ||
| PCT/US2011/036821 WO2011146494A1 (en) | 2010-05-17 | 2011-05-17 | Novel processes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130089157A true KR20130089157A (ko) | 2013-08-09 |
Family
ID=44992024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20127032795A Abandoned KR20130089157A (ko) | 2010-05-17 | 2011-05-17 | 신규 방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US9447052B2 (enExample) |
| EP (1) | EP2571857B1 (enExample) |
| JP (1) | JP6027529B2 (enExample) |
| KR (1) | KR20130089157A (enExample) |
| CN (2) | CN103003249B (enExample) |
| AR (1) | AR081399A1 (enExample) |
| AU (1) | AU2011256270B2 (enExample) |
| BR (1) | BR112012030532A2 (enExample) |
| CA (1) | CA2799520C (enExample) |
| CL (1) | CL2012003206A1 (enExample) |
| CO (1) | CO6630197A2 (enExample) |
| CR (1) | CR20120630A (enExample) |
| DO (1) | DOP2012000289A (enExample) |
| EA (1) | EA026569B1 (enExample) |
| IL (1) | IL223068A0 (enExample) |
| MA (1) | MA34301B1 (enExample) |
| MX (1) | MX2012013387A (enExample) |
| NZ (1) | NZ603672A (enExample) |
| PE (1) | PE20130318A1 (enExample) |
| PH (1) | PH12012502247A1 (enExample) |
| SG (1) | SG185559A1 (enExample) |
| TW (1) | TW201209043A (enExample) |
| UY (1) | UY33388A (enExample) |
| WO (1) | WO2011146494A1 (enExample) |
| ZA (1) | ZA201208631B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33388A (es) * | 2010-05-17 | 2011-12-01 | Glaxo Group Ltd | Nuevos procesos para la preparacion de compuestos de pirimidinona |
| WO2015087239A1 (en) | 2013-12-11 | 2015-06-18 | Ranbaxy Laboratories Limited | Processes for the preparation of darapladib and its intermediates |
| WO2015092687A2 (en) | 2013-12-17 | 2015-06-25 | Ranbaxy Laboratories Limited | Process for the purification of darapladib |
| US11583596B2 (en) | 2017-09-26 | 2023-02-21 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Radiolabeled Darapladib and analogs thereof and their use as imaging compounds |
| US10866963B2 (en) * | 2017-12-28 | 2020-12-15 | Dropbox, Inc. | File system authentication |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1143516B (de) | 1961-04-27 | 1963-02-14 | Bayer Ag | Verfahren zur Herstellung von Peptiden |
| US4277465A (en) | 1978-08-26 | 1981-07-07 | Kyoto Yakuhin Kogyo Kabushiki Kaisha | Adjuvant for promoting absorption of therapeutically active substances through the digestive tract |
| US4235776A (en) * | 1979-03-15 | 1980-11-25 | Eli Lilly And Company | Tetrahydro-2H-benzo[c]pyrroles |
| DE2941597A1 (de) * | 1979-10-13 | 1981-04-23 | Basf Ag, 6700 Ludwigshafen | Piperidinderivate von 4,5-dialkyl-3-hydroxy-pyrrol-2-carbonsaeureestern, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| US4619941A (en) * | 1984-11-19 | 1986-10-28 | American Cyanamid Company | N-[(1H-imidazol-1-yl)alkyl]-1H-indolecarboxamides useful as thromboxane synthetase inhibitors and antihypertensive agents |
| JP2001522844A (ja) * | 1997-11-06 | 2001-11-20 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ピリミジノン化合物およびそれを含有する医薬組成物 |
| US6750228B1 (en) | 1997-11-14 | 2004-06-15 | Pharmacia Corporation | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
| US6503745B1 (en) | 1998-11-05 | 2003-01-07 | Biocryst Pharmaceuticals, Inc. | Cyclopentane and cyclopentene compounds and use for detecting influenza virus |
| PT1175408E (pt) | 1999-05-01 | 2005-04-29 | Smithkline Beecham Plc | Derivados sulfonamida |
| BRPI0108396B1 (pt) * | 2000-02-16 | 2015-05-19 | Smithkline Beecham Plc | Derivados de pirimidina-4-ona como inibidores de ldl-pla2 |
| GB0119795D0 (en) * | 2001-08-14 | 2001-10-03 | Smithkline Beecham Plc | Novel process |
| UY33388A (es) * | 2010-05-17 | 2011-12-01 | Glaxo Group Ltd | Nuevos procesos para la preparacion de compuestos de pirimidinona |
-
2011
- 2011-05-16 UY UY33388A patent/UY33388A/es not_active Application Discontinuation
- 2011-05-16 TW TW100117029A patent/TW201209043A/zh unknown
- 2011-05-16 AR ARP110101679 patent/AR081399A1/es unknown
- 2011-05-17 BR BR112012030532A patent/BR112012030532A2/pt not_active IP Right Cessation
- 2011-05-17 SG SG2012083648A patent/SG185559A1/en unknown
- 2011-05-17 MX MX2012013387A patent/MX2012013387A/es unknown
- 2011-05-17 NZ NZ60367211A patent/NZ603672A/en not_active IP Right Cessation
- 2011-05-17 KR KR20127032795A patent/KR20130089157A/ko not_active Abandoned
- 2011-05-17 US US13/698,102 patent/US9447052B2/en not_active Expired - Fee Related
- 2011-05-17 JP JP2013511295A patent/JP6027529B2/ja not_active Expired - Fee Related
- 2011-05-17 PE PE2012002160A patent/PE20130318A1/es not_active Application Discontinuation
- 2011-05-17 EA EA201291235A patent/EA026569B1/ru not_active IP Right Cessation
- 2011-05-17 CA CA2799520A patent/CA2799520C/en not_active Expired - Fee Related
- 2011-05-17 MA MA35441A patent/MA34301B1/fr unknown
- 2011-05-17 WO PCT/US2011/036821 patent/WO2011146494A1/en not_active Ceased
- 2011-05-17 PH PH1/2012/502247A patent/PH12012502247A1/en unknown
- 2011-05-17 CN CN201180035126.7A patent/CN103003249B/zh not_active Expired - Fee Related
- 2011-05-17 EP EP11784095.9A patent/EP2571857B1/en active Active
- 2011-05-17 CN CN201610182606.0A patent/CN105837520A/zh active Pending
- 2011-05-17 AU AU2011256270A patent/AU2011256270B2/en not_active Ceased
-
2012
- 2012-11-15 DO DO2012000289A patent/DOP2012000289A/es unknown
- 2012-11-15 IL IL223068A patent/IL223068A0/en unknown
- 2012-11-16 CL CL2012003206A patent/CL2012003206A1/es unknown
- 2012-11-16 CO CO12208170A patent/CO6630197A2/es unknown
- 2012-11-16 ZA ZA2012/08631A patent/ZA201208631B/en unknown
- 2012-12-12 CR CR20120630A patent/CR20120630A/es unknown
-
2016
- 2016-08-12 US US15/235,468 patent/US9725420B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2138483C1 (ru) | Способ получения производных 3-хинолонкарбоновой кислоты | |
| US9725420B2 (en) | Processes | |
| JP4048119B2 (ja) | ２−（４−クロロベンゾイルアミノ）−３−［２（１ｈ）−キノールリノン−４−イル］プロピオン酸の製造方法 | |
| HU204258B (en) | Process for producing intermediates for producing quinoline derivatives of antibacterial activity | |
| JP3007050B2 (ja) | イミダゾベンゾジアゼピン誘導体の製造方法 | |
| JPWO2014103811A1 (ja) | 精製されたアミン化合物の製造方法 | |
| JP2846042B2 (ja) | インドールカルボン酸誘導体の製造法 | |
| JP2000026425A (ja) | キノロンカルボン酸とナフチリドンカルボン酸及びそのエステルの製造方法 | |
| DE69512495T2 (de) | Verfahren zur Herstellung von Chinolin-2-yl-benzoesäure | |
| JP2010510253A5 (enExample) | ||
| HRP20040606A2 (en) | A process for producing phenserine and its analog | |
| CN1300141C (zh) | 制造非核苷hiv－1逆转录酶抑制剂的方法和中间体 | |
| US20080194623A1 (en) | Method for the Synthesis of Quinoline Derivatives | |
| EP4423104A1 (en) | Stereoselective steroidal reductions | |
| KR20100102606A (ko) | 2ｈ-크로멘-3-카르바메이트 유도체의 제조방법 | |
| US20040010146A1 (en) | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides | |
| SK13592001A3 (sk) | Syntéza 3-amino-3-arylpropanoátov | |
| JP2003514908A (ja) | テトラヒドロ−［１，８］−ナフチリジンに向けた方法および中間体 | |
| JP2004506634A (ja) | イミダゾピリジン類の製造方法 | |
| CN103906739A (zh) | 用于制备hcv的大环蛋白酶抑制剂的方法和中间体 | |
| JPH09169748A (ja) | ２−アミノチアゾール−５−カルボニトリル誘導体の製造方法 | |
| NZ626732B2 (en) | Process for the preparation of (5-fluoro-2-methyl-3-quinolin-2-ylmethyl-indol-1-yl)-acetic acid esters | |
| HK1199449B (en) | Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20121214 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20160516 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20170210 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20170703 |
|
| PC1904 | Unpaid initial registration fee |