ZA200308261B - Processes and intermediates for preparing benzyl epoxides. - Google Patents
Processes and intermediates for preparing benzyl epoxides. Download PDFInfo
- Publication number
- ZA200308261B ZA200308261B ZA200308261A ZA200308261A ZA200308261B ZA 200308261 B ZA200308261 B ZA 200308261B ZA 200308261 A ZA200308261 A ZA 200308261A ZA 200308261 A ZA200308261 A ZA 200308261A ZA 200308261 B ZA200308261 B ZA 200308261B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- optionally substituted
- halogen
- phenyl
- cycloalkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 110
- -1 benzyl epoxides Chemical class 0.000 title claims description 38
- 239000000543 intermediate Substances 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 285
- 150000002367 halogens Chemical class 0.000 claims description 122
- 229910052736 halogen Inorganic materials 0.000 claims description 103
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
- 229910052799 carbon Inorganic materials 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000003342 alkenyl group Chemical group 0.000 claims description 51
- 125000000304 alkynyl group Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 49
- 125000001246 bromo group Chemical group Br* 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 21
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 150000002118 epoxides Chemical class 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 229910052744 lithium Inorganic materials 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 3
- 125000002346 iodo group Chemical group I* 0.000 claims 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 3
- 239000010948 rhodium Substances 0.000 claims 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims 3
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 150000001559 benzoic acids Chemical class 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- ZIMRMCAQMJKGDJ-INIZCTEOSA-N methyl (2s)-3-(3,5-difluorophenyl)-2-(phenylmethoxycarbonylamino)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)OCC=1C=CC=CC=1)C1=CC(F)=CC(F)=C1 ZIMRMCAQMJKGDJ-INIZCTEOSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- CPDCSUDWYWFWOW-NSHDSACASA-N tert-butyl n-[(2s)-1-chloro-3-(3,5-difluorophenyl)-1-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C(Cl)=O)CC1=CC(F)=CC(F)=C1 CPDCSUDWYWFWOW-NSHDSACASA-N 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- CQYMOICHLLQQAH-UHFFFAOYSA-N (r)-binaphane Chemical compound C1C2=CC=C3C=CC=CC3=C2C(C2=CC=CC=C2C=C2)=C2CP1C1=CC=CC=C1P(C1)CC2=CC=C(C=CC=C3)C3=C2C2=C1C=CC1=CC=CC=C21 CQYMOICHLLQQAH-UHFFFAOYSA-N 0.000 claims 1
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 claims 1
- 229910014585 C2-Ce Inorganic materials 0.000 claims 1
- 102100028139 Oxytocin receptor Human genes 0.000 claims 1
- 101710103206 Oxytocin receptor Proteins 0.000 claims 1
- GYKMEKRMASHMIH-VSJLXWSYSA-N [(3r,4r)-1-benzyl-4-diphenylphosphanylpyrrolidin-3-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@H]1[C@@H](CN(C1)CC=1C=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 GYKMEKRMASHMIH-VSJLXWSYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000005587 carbonate group Chemical group 0.000 claims 1
- FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 claims 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- BFMKBYZEJOQYIM-UCGGBYDDSA-N tert-butyl (2s,4s)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound C([C@@H]1C[C@@H](CN1C(=O)OC(C)(C)C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BFMKBYZEJOQYIM-UCGGBYDDSA-N 0.000 claims 1
- UDEJEOLNSNYQSX-UHFFFAOYSA-J tetrasodium;2,4,6,8-tetraoxido-1,3,5,7,2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraoxatetraphosphocane 2,4,6,8-tetraoxide Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])(=O)O1 UDEJEOLNSNYQSX-UHFFFAOYSA-J 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07C229/34—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 containing six-membered aromatic rings
- C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28577201P | 2001-04-23 | 2001-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308261B true ZA200308261B (en) | 2004-05-24 |
Family
ID=23095626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308261A ZA200308261B (en) | 2001-04-23 | 2003-10-23 | Processes and intermediates for preparing benzyl epoxides. |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6849750B2 (es) |
| EP (1) | EP1381597B1 (es) |
| JP (1) | JP2004529152A (es) |
| KR (1) | KR20040047750A (es) |
| CN (1) | CN1612871A (es) |
| AP (1) | AP2003002897A0 (es) |
| AR (1) | AR035960A1 (es) |
| AT (1) | ATE401299T1 (es) |
| BR (1) | BR0209163A (es) |
| CA (1) | CA2445163A1 (es) |
| CO (1) | CO5650163A2 (es) |
| DE (1) | DE60227652D1 (es) |
| EA (1) | EA007535B1 (es) |
| ES (1) | ES2309170T3 (es) |
| IL (2) | IL158585A0 (es) |
| MX (1) | MXPA03009723A (es) |
| NO (1) | NO20034738L (es) |
| NZ (1) | NZ529169A (es) |
| OA (1) | OA12597A (es) |
| PE (1) | PE20021068A1 (es) |
| PL (1) | PL365058A1 (es) |
| WO (1) | WO2002085877A2 (es) |
| ZA (1) | ZA200308261B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0228410D0 (en) * | 2002-12-05 | 2003-01-08 | Glaxo Group Ltd | Novel Compounds |
| US20050239836A1 (en) | 2004-03-09 | 2005-10-27 | Varghese John | Substituted hydroxyethylamine aspartyl protease inhibitors |
| US7385085B2 (en) | 2004-07-09 | 2008-06-10 | Elan Pharmaceuticals, Inc. | Oxime derivative substituted hydroxyethylamine aspartyl protease inhibitors |
| WO2007047305A1 (en) | 2005-10-12 | 2007-04-26 | Elan Pharmaceuticals, Inc. | Methods of treating amyloidosis using cyclopropyl derivative aspartyl protease inhibitors |
| WO2019168874A1 (en) | 2018-02-27 | 2019-09-06 | The Research Foundation For The State University Of New York | Difluoromethoxylation and trifluoromethoxylation compositions and methods for synthesizing same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2788044B2 (ja) | 1989-02-06 | 1998-08-20 | サントリー株式会社 | マレイミド誘導体およびそれを有効成分として含有する農園芸用殺菌剤 |
| US5583238A (en) | 1990-11-19 | 1996-12-10 | G. D. Searle & Co. | Method for making intermediates useful in synthesis of retroviral protease inhibitors |
| US5482947A (en) | 1990-11-19 | 1996-01-09 | Talley; John J. | Retroviral protease inhibitors |
| US5559256A (en) * | 1992-07-20 | 1996-09-24 | E. R. Squibb & Sons, Inc. | Aminediol protease inhibitors |
| AU669223B2 (en) | 1992-08-25 | 1996-05-30 | G.D. Searle & Co. | Sulfonylalkanoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US5481011A (en) * | 1994-12-13 | 1996-01-02 | Bristol-Myers Squibb Company | Process for preparing N-protected amino acid α-halomethyl ketones and alcohols from N-protected amino acid esters |
| US5985911A (en) * | 1997-01-07 | 1999-11-16 | Abbott Laboratories | C-terminal ketone inhibitors of matrix metalloproteinases and TNFα secretion |
| WO1998033795A1 (en) * | 1997-02-04 | 1998-08-06 | The Regents Of The University Of California | Nanomolar, non-peptide inhibitors of cathepsin d |
| CA2273643A1 (en) | 1998-06-09 | 1999-12-09 | F. Hoffmann-La Roche Ag | Stereoselective reduction of carbonyl compounds |
| DE60124080T2 (de) | 2000-03-23 | 2007-03-01 | Elan Pharmaceuticals, Inc., San Francisco | Verbindungen und verfahren zur behandlung der alzheimerschen krankheit |
| EP1299352B1 (en) | 2000-06-30 | 2005-12-28 | Elan Pharmaceuticals, Inc. | Compounds to treat alzheimer's disease |
| PE20020276A1 (es) | 2000-06-30 | 2002-04-06 | Elan Pharm Inc | COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER |
| US20030096864A1 (en) | 2000-06-30 | 2003-05-22 | Fang Lawrence Y. | Compounds to treat alzheimer's disease |
| US6846813B2 (en) | 2000-06-30 | 2005-01-25 | Pharmacia & Upjohn Company | Compounds to treat alzheimer's disease |
| AU2002360508A1 (en) | 2001-12-06 | 2003-06-23 | Elan Pharmaceuticals, Inc. | Substituted hydroxyethylamines |
-
2002
- 2002-04-19 AR ARP020101444A patent/AR035960A1/es unknown
- 2002-04-23 AT AT02728882T patent/ATE401299T1/de not_active IP Right Cessation
- 2002-04-23 OA OA1200300276A patent/OA12597A/en unknown
- 2002-04-23 NZ NZ529169A patent/NZ529169A/en unknown
- 2002-04-23 PE PE2002000343A patent/PE20021068A1/es not_active Application Discontinuation
- 2002-04-23 MX MXPA03009723A patent/MXPA03009723A/es active IP Right Grant
- 2002-04-23 CA CA002445163A patent/CA2445163A1/en not_active Abandoned
- 2002-04-23 KR KR10-2003-7013902A patent/KR20040047750A/ko not_active Application Discontinuation
- 2002-04-23 CN CNA02812636XA patent/CN1612871A/zh active Pending
- 2002-04-23 WO PCT/US2002/012591 patent/WO2002085877A2/en active IP Right Grant
- 2002-04-23 JP JP2002583404A patent/JP2004529152A/ja active Pending
- 2002-04-23 ES ES02728882T patent/ES2309170T3/es not_active Expired - Lifetime
- 2002-04-23 EP EP02728882A patent/EP1381597B1/en not_active Expired - Lifetime
- 2002-04-23 DE DE60227652T patent/DE60227652D1/de not_active Expired - Fee Related
- 2002-04-23 AP APAP/P/2003/002897A patent/AP2003002897A0/en unknown
- 2002-04-23 PL PL02365058A patent/PL365058A1/xx not_active Application Discontinuation
- 2002-04-23 EA EA200301133A patent/EA007535B1/ru not_active IP Right Cessation
- 2002-04-23 US US10/128,122 patent/US6849750B2/en not_active Expired - Fee Related
- 2002-04-23 IL IL15858502A patent/IL158585A0/xx unknown
- 2002-04-23 BR BR0209163-1A patent/BR0209163A/pt not_active IP Right Cessation
-
2003
- 2003-10-23 IL IL158585A patent/IL158585A/en not_active IP Right Cessation
- 2003-10-23 ZA ZA200308261A patent/ZA200308261B/en unknown
- 2003-10-23 NO NO20034738A patent/NO20034738L/no not_active Application Discontinuation
- 2003-11-20 CO CO03102567A patent/CO5650163A2/es not_active Application Discontinuation
-
2005
- 2005-02-01 US US11/048,389 patent/US7638646B2/en not_active Expired - Fee Related
-
2009
- 2009-12-23 US US12/646,526 patent/US20100099898A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2445163A1 (en) | 2002-10-31 |
| EP1381597B1 (en) | 2008-07-16 |
| BR0209163A (pt) | 2004-08-24 |
| US7638646B2 (en) | 2009-12-29 |
| KR20040047750A (ko) | 2004-06-05 |
| WO2002085877A2 (en) | 2002-10-31 |
| CO5650163A2 (es) | 2006-06-30 |
| EA200301133A1 (ru) | 2004-04-29 |
| IL158585A (en) | 2009-06-15 |
| AR035960A1 (es) | 2004-07-28 |
| NO20034738D0 (no) | 2003-10-23 |
| NZ529169A (en) | 2005-06-24 |
| ES2309170T3 (es) | 2008-12-16 |
| AP2003002897A0 (en) | 2003-12-31 |
| OA12597A (en) | 2006-06-08 |
| US20050130936A1 (en) | 2005-06-16 |
| MXPA03009723A (es) | 2004-03-16 |
| EA007535B1 (ru) | 2006-10-27 |
| US20030004360A1 (en) | 2003-01-02 |
| ATE401299T1 (de) | 2008-08-15 |
| NO20034738L (no) | 2003-12-04 |
| EP1381597A2 (en) | 2004-01-21 |
| IL158585A0 (en) | 2004-05-12 |
| PE20021068A1 (es) | 2002-12-11 |
| US6849750B2 (en) | 2005-02-01 |
| DE60227652D1 (de) | 2008-08-28 |
| US20100099898A1 (en) | 2010-04-22 |
| WO2002085877A3 (en) | 2003-03-06 |
| PL365058A1 (en) | 2004-12-27 |
| CN1612871A (zh) | 2005-05-04 |
| JP2004529152A (ja) | 2004-09-24 |
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