EA016140B1 - Способ получения бисфуранового спирта - Google Patents
Способ получения бисфуранового спирта Download PDFInfo
- Publication number
- EA016140B1 EA016140B1 EA200802074A EA200802074A EA016140B1 EA 016140 B1 EA016140 B1 EA 016140B1 EA 200802074 A EA200802074 A EA 200802074A EA 200802074 A EA200802074 A EA 200802074A EA 016140 B1 EA016140 B1 EA 016140B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- reaction
- solvent
- bisfuran alcohol
- bisfuran
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 34
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 4
- 150000002602 lanthanoids Chemical class 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- QYVLFKNPUCXXQJ-UHFFFAOYSA-N 8-naphthalen-1-ylnaphthalen-1-ol Chemical compound C1=CC=C2C(C=3C=CC=C4C=CC=C(C=34)O)=CC=CC2=C1 QYVLFKNPUCXXQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 27
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- RCDXYCHYMULCDZ-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-ol Chemical compound O1CCC2C(O)COC21 RCDXYCHYMULCDZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ATFVTAOSZBVGHC-UHFFFAOYSA-N Glycolaldehyde dimer Chemical compound OC1COC(O)CO1 ATFVTAOSZBVGHC-UHFFFAOYSA-N 0.000 description 3
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- -1 Aminoethylphosphoric acid diesters Chemical class 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004030 hiv protease inhibitor Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940122440 HIV protease inhibitor Drugs 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000004185 countercurrent chromatography Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- GCSAXWHQFYOIFE-UHFFFAOYSA-N dipyridin-2-yl carbonate Chemical compound C=1C=CC=NC=1OC(=O)OC1=CC=CC=N1 GCSAXWHQFYOIFE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CFPVQGQJRGIWSP-UHFFFAOYSA-N scandium(3+) Chemical compound [Sc+3] CFPVQGQJRGIWSP-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/42—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78712606P | 2006-03-29 | 2006-03-29 | |
| PCT/US2007/007564 WO2007126812A2 (en) | 2006-03-29 | 2007-03-29 | Process for preparation of hiv protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200802074A1 EA200802074A1 (ru) | 2009-02-27 |
| EA016140B1 true EA016140B1 (ru) | 2012-02-28 |
Family
ID=38323963
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200802074A EA016140B1 (ru) | 2006-03-29 | 2007-03-29 | Способ получения бисфуранового спирта |
| EA201100994A EA020088B1 (ru) | 2006-03-29 | 2007-03-29 | Способ получения производных бисфуранового спирта, соединения, соль, фармацевтическая композиция на ее основе, способ лечения или профилактики ретровирусных инфекций с ее помощью |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201100994A EA020088B1 (ru) | 2006-03-29 | 2007-03-29 | Способ получения производных бисфуранового спирта, соединения, соль, фармацевтическая композиция на ее основе, способ лечения или профилактики ретровирусных инфекций с ее помощью |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US20110065631A1 (enExample) |
| EP (2) | EP2570416B1 (enExample) |
| JP (2) | JP5430395B2 (enExample) |
| KR (2) | KR101429300B1 (enExample) |
| CN (2) | CN102516259B (enExample) |
| AP (2) | AP2013006690A0 (enExample) |
| AU (1) | AU2007245194B2 (enExample) |
| BR (1) | BRPI0710199A2 (enExample) |
| CA (1) | CA2647316C (enExample) |
| DK (1) | DK1999133T3 (enExample) |
| EA (2) | EA016140B1 (enExample) |
| ES (2) | ES2572001T3 (enExample) |
| HR (2) | HRP20140626A2 (enExample) |
| IL (2) | IL194122A (enExample) |
| MX (1) | MX2008012398A (enExample) |
| NO (2) | NO342102B1 (enExample) |
| NZ (2) | NZ596074A (enExample) |
| PL (1) | PL1999133T3 (enExample) |
| PT (1) | PT1999133E (enExample) |
| SG (1) | SG170794A1 (enExample) |
| SI (1) | SI1999133T1 (enExample) |
| UA (1) | UA97241C2 (enExample) |
| WO (1) | WO2007126812A2 (enExample) |
| ZA (1) | ZA200808046B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8921415B2 (en) | 2009-01-29 | 2014-12-30 | Mapi Pharma Ltd. | Polymorphs of darunavir |
| PL2528923T3 (pl) | 2010-01-28 | 2015-01-30 | Mapi Pharma Ltd | Sposób wytwarzania darunawiru i pochodnych darunawiru |
| CN102190638A (zh) * | 2010-03-16 | 2011-09-21 | 中国科学院上海药物研究所 | 联芳基醇二胺类化合物、其药物组合物、制备方法及应用 |
| CN102584748B (zh) * | 2011-01-13 | 2015-02-11 | 浙江九洲药业股份有限公司 | 夫沙那韦中间体的制备方法 |
| EP2702045B1 (en) * | 2011-04-26 | 2017-10-18 | Mylan Laboratories Ltd. | Novel process for the preparation of etravirine |
| ES2661705T3 (es) | 2011-10-07 | 2018-04-03 | Gilead Sciences, Inc. | Métodos para la preparación de análogos de nucleótidos antivirales |
| EP2634180A1 (en) | 2012-03-01 | 2013-09-04 | Lonza Ltd. | Enzymatic process for the preparation of butyrolactones |
| CN103664976B (zh) * | 2013-12-12 | 2015-11-04 | 惠州市莱佛士制药技术有限公司 | 一种顺式六氢呋喃并[2,3-b]呋喃-3-醇的制备方法 |
| ES2802376T3 (es) | 2014-02-12 | 2021-01-19 | Firmenich Incorporated | Procedimiento mejorado para la síntesis de 1-bencil-3-(1-(isoxazol-4-ilmetil)-1h-pirazol-4-il)imidazolidin-2,4-dionas sustituidas |
| WO2016106050A1 (en) | 2014-12-26 | 2016-06-30 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| JP6435907B2 (ja) * | 2015-02-16 | 2018-12-12 | 住友化学株式会社 | ヘキサヒドロフロフラノール誘導体の製造方法 |
| CN108610227B (zh) * | 2016-12-10 | 2021-02-09 | 中国科学院大连化学物理研究所 | 一种制备双环芳香化合物的方法 |
| RU2020116571A (ru) | 2017-12-07 | 2021-11-22 | Эмори Юниверсити | N4-гидроксицитидин и производные и связанные с этим противовирусные применения |
| MX2021008751A (es) | 2019-01-25 | 2021-11-12 | Univ Brown | Composiciones y metodos para tratar, prevenir o revertir la inflamacion y los trastornos asociados a la edad. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026749A1 (en) * | 1993-05-14 | 1994-11-24 | Merck & Co., Inc. | Hiv protease inhibitors |
| WO2002067239A2 (en) * | 2000-10-24 | 2002-08-29 | Glaxo Group Limited | Process for preparing intermediates of hiv protease inhibitors |
| US20040121316A1 (en) * | 2002-04-26 | 2004-06-24 | Gilead Sciences, Inc. | Method and compositions for identifying anti-HIV therapeutic compounds |
| WO2005042772A1 (en) * | 2003-10-24 | 2005-05-12 | Gilead Sciences, Inc. | Methods and compositions for identifying therapeutic compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1369001A (en) * | 1995-12-13 | 2001-03-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
| ATE401298T1 (de) | 1999-12-23 | 2008-08-15 | Ampac Fine Chemicals Llc | Verbessertes verfahren zur herstellung von 2s,3s- n-isobutyl-n-(2-hydroxy-3-amino-4-phenylbutyl)- - nitrobenzenesulfonylamid hydrochlorid und anderen derivaten von 2-hydroxy-1,3-diamin |
| EP1436884A2 (en) | 2001-07-20 | 2004-07-14 | Koninklijke Philips Electronics N.V. | Oscillating circuit, converter with such oscillating circuit, and preconditioner with such converter |
| US20050239054A1 (en) * | 2002-04-26 | 2005-10-27 | Arimilli Murty N | Method and compositions for identifying anti-HIV therapeutic compounds |
-
2007
- 2007-03-29 EA EA200802074A patent/EA016140B1/ru not_active IP Right Cessation
- 2007-03-29 NZ NZ596074A patent/NZ596074A/xx not_active IP Right Cessation
- 2007-03-29 HR HRP20140626AA patent/HRP20140626A2/hr not_active Application Discontinuation
- 2007-03-29 EA EA201100994A patent/EA020088B1/ru not_active IP Right Cessation
- 2007-03-29 SG SG201102217-5A patent/SG170794A1/en unknown
- 2007-03-29 PL PL07754134T patent/PL1999133T3/pl unknown
- 2007-03-29 BR BRPI0710199-6A patent/BRPI0710199A2/pt not_active IP Right Cessation
- 2007-03-29 AP AP2013006690A patent/AP2013006690A0/xx unknown
- 2007-03-29 ES ES12192910T patent/ES2572001T3/es active Active
- 2007-03-29 KR KR1020087026569A patent/KR101429300B1/ko active Active
- 2007-03-29 PT PT77541340T patent/PT1999133E/pt unknown
- 2007-03-29 AU AU2007245194A patent/AU2007245194B2/en active Active
- 2007-03-29 CA CA2647316A patent/CA2647316C/en active Active
- 2007-03-29 DK DK07754134.0T patent/DK1999133T3/da active
- 2007-03-29 SI SI200731323T patent/SI1999133T1/sl unknown
- 2007-03-29 US US12/293,450 patent/US20110065631A1/en not_active Abandoned
- 2007-03-29 CN CN201110315578.2A patent/CN102516259B/zh active Active
- 2007-03-29 EP EP12192910.3A patent/EP2570416B1/en active Active
- 2007-03-29 HR HRP20080554AA patent/HRP20080554B1/hr not_active IP Right Cessation
- 2007-03-29 NZ NZ571302A patent/NZ571302A/en not_active IP Right Cessation
- 2007-03-29 MX MX2008012398A patent/MX2008012398A/es active IP Right Grant
- 2007-03-29 KR KR1020137034899A patent/KR101395377B1/ko active Active
- 2007-03-29 JP JP2009502946A patent/JP5430395B2/ja active Active
- 2007-03-29 US US11/729,522 patent/US8173623B2/en active Active
- 2007-03-29 WO PCT/US2007/007564 patent/WO2007126812A2/en not_active Ceased
- 2007-03-29 UA UAA200811574A patent/UA97241C2/uk unknown
- 2007-03-29 ES ES07754134T patent/ES2430557T3/es active Active
- 2007-03-29 CN CN2007800178888A patent/CN101448838B/zh active Active
- 2007-03-29 AP AP2008004641A patent/AP2757A/xx active
- 2007-03-29 EP EP07754134.0A patent/EP1999133B1/en active Active
-
2008
- 2008-09-16 IL IL194122A patent/IL194122A/en not_active IP Right Cessation
- 2008-09-19 ZA ZA200808046A patent/ZA200808046B/xx unknown
- 2008-10-28 NO NO20084547A patent/NO342102B1/no unknown
-
2012
- 2012-02-21 US US13/401,659 patent/US8431745B2/en active Active
- 2012-12-12 JP JP2012271186A patent/JP2013082717A/ja not_active Withdrawn
-
2013
- 2013-02-27 US US13/779,188 patent/US20130172295A1/en not_active Abandoned
- 2013-03-12 IL IL225167A patent/IL225167A/en not_active IP Right Cessation
-
2018
- 2018-01-17 NO NO20180086A patent/NO342965B1/no unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026749A1 (en) * | 1993-05-14 | 1994-11-24 | Merck & Co., Inc. | Hiv protease inhibitors |
| WO2002067239A2 (en) * | 2000-10-24 | 2002-08-29 | Glaxo Group Limited | Process for preparing intermediates of hiv protease inhibitors |
| US20040121316A1 (en) * | 2002-04-26 | 2004-06-24 | Gilead Sciences, Inc. | Method and compositions for identifying anti-HIV therapeutic compounds |
| WO2005042772A1 (en) * | 2003-10-24 | 2005-05-12 | Gilead Sciences, Inc. | Methods and compositions for identifying therapeutic compounds |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2647316C (en) | Process for preparation of hiv protease inhibitors | |
| CN117843525B (zh) | (2s,3r,4r)-4,5-二羟基异亮氨酸衍生物及中间体的制备方法 | |
| CN114805206B (zh) | 高光学纯度瑞美吉泮中间体的工业化制备方法 | |
| WO1995010266A1 (fr) | Inhibiteur de synthese de monoxyde d'azote | |
| Kudyba et al. | Highly diastereoselective Henry reaction of nitro compounds with chiral derivatives of glyoxylic acid | |
| Czech et al. | Cesium fluoride assisted synthesis of macrocyclic polyethers with aromatic subunits | |
| WO2020243754A1 (en) | LIGAND-ENABLED ß-C(sp3)–H LACTONIZATION FOR ß-C–H FUNCTIONALIZATIONS | |
| JP6201823B2 (ja) | ４’−ｏ−グルコシル−５−ｏ−メチルビサミノールの製造方法 | |
| KR100547958B1 (ko) | 키랄 크라운에테르를 기저로한 ｌｃ용 키랄 고정상, 이의키랄 칼럼 및 이의 제조방법 | |
| EP2221300B1 (en) | Methods for resolution of the mixture of the optical isomers, especially the racemate of pinocembrin | |
| JPH0684367B2 (ja) | フオルスコリン誘導体の新規製造法 | |
| JPS6218539B2 (enExample) | ||
| CN1216023C (zh) | 反式－（＋）－水合蒎醇制备方法 | |
| JP2000344758A (ja) | （メタ）アクリル酸エステルの製造方法 | |
| CN114835694A (zh) | 一种在水介质中合成手性3，4-二氢-2h-吡喃类化合物的方法 | |
| JP4568002B2 (ja) | 光学活性な２−フルオロ−１，３−ジオール誘導体およびその製造方法 | |
| JPH03251577A (ja) | 光学活性スチレンオキシドの立体化学反転法および光学活性グリコール誘導体の製法 | |
| WO2002044136A1 (en) | PROCESSES FOR PREPARATION OF N-PROTECTED-ss-AMINO ALCOHOLS AND N-PROTECTED-ss-AMINO EPOXIDES | |
| US20060014939A1 (en) | Novel C6-substituted furanoid sugar amino acids and improved process for preparing the same | |
| JP2006089493A (ja) | 光学活性コバルト（ｉｉ）錯体 | |
| Goel | Synthesis of Novel Tröger’s Base-Derived Helical Scaffolds | |
| JP3210683B2 (ja) | 異性体分離法 | |
| CN118852080A (zh) | 一种手性氨基色满酮衍生物及其合成方法 | |
| JPH0217198A (ja) | ２’−デオキシ−β−シチジン誘導体およびその塩の製造法 | |
| JPS60126280A (ja) | 光学活性エピクロルヒドリンの製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |