SK127398A3 - Novel asymmetric synthesis of r-'alpha'-propyl-piperonyl amine and its analogs - Google Patents

Novel asymmetric synthesis of r-'alpha'-propyl-piperonyl amine and its analogs Download PDF

Info

Publication number: SK127398A3
Authority: SK; Slovakia
Prior art keywords: compound; acid; hours; temperature; alcohol
Prior art date: 1996-03-22

Application number

SK1273-98A

Other languages

English (en)

Slovak (sk)

Inventor

Hui-Yin Li

Luigi Anzalone

Robert E Waltermire

Original Assignee

Du Pont Pharm Co

Priority date (The priority date 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 date listed.)

1996-03-22

Filing date

1997-03-17

Publication date

1999-04-13

1997-03-17 Application filed by Du Pont Pharm Co filed Critical Du Pont Pharm Co

1999-04-13 Publication of SK127398A3 publication Critical patent/SK127398A3/sk

Links

238000011914 asymmetric synthesis Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 101
238000000034 method Methods 0.000 claims abstract description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 136
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 91
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 45
150000003839 salts Chemical group 0.000 claims description 45
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
239000001257 hydrogen Substances 0.000 claims description 44
238000005984 hydrogenation reaction Methods 0.000 claims description 43
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 20
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 18
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
229910000564 Raney nickel Inorganic materials 0.000 claims description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
-1 allyl magnesium Chemical compound 0.000 claims description 10
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 8
229910052684 Cerium Inorganic materials 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 8
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 7
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical group CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 7
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical compound OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
230000002194 synthesizing effect Effects 0.000 claims description 4
150000003892 tartrate salts Chemical class 0.000 claims description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
230000036571 hydration Effects 0.000 claims 1
238000006703 hydration reaction Methods 0.000 claims 1
229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
229910052749 magnesium Inorganic materials 0.000 claims 1
239000011777 magnesium Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 11
239000003602 elastase inhibitor Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 76
238000006243 chemical reaction Methods 0.000 description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 19
239000003054 catalyst Substances 0.000 description 17
238000007792 addition Methods 0.000 description 16
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
150000002466 imines Chemical class 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
239000012458 free base Substances 0.000 description 6
150000004795 grignard reagents Chemical class 0.000 description 6
239000000725 suspension Substances 0.000 description 6
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 5
239000002738 chelating agent Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
239000007818 Grignard reagent Substances 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000012071 phase Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000011975 tartaric acid Substances 0.000 description 4
235000002906 tartaric acid Nutrition 0.000 description 4
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
IJXJGQCXFSSHNL-QMMMGPOBSA-N (R)-(-)-2-Phenylglycinol Chemical compound OC[C@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-QMMMGPOBSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 2
LBQQOZCTSFHMHQ-UHFFFAOYSA-N 2-oxo-4-phenoxyazetidine-1-carboxamide Chemical compound O(C1=CC=CC=C1)C1N(C(C1)=O)C(=O)N LBQQOZCTSFHMHQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
102000016387 Pancreatic elastase Human genes 0.000 description 2
108010067372 Pancreatic elastase Proteins 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006264 debenzylation reaction Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 2
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 2
CYSFUFRXDOAOMP-UHFFFAOYSA-M magnesium;prop-1-ene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C=C CYSFUFRXDOAOMP-UHFFFAOYSA-M 0.000 description 2
RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
229960002510 mandelic acid Drugs 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UNNGDZIQTSGWFG-UHFFFAOYSA-N 1-(furan-2-yl)butan-1-amine Chemical compound CCCC(N)C1=CC=CO1 UNNGDZIQTSGWFG-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
ZWFRWORXTLECGO-UHFFFAOYSA-N 1-hexan-3-ylpiperidine Chemical compound CCCC(CC)N1CCCCC1 ZWFRWORXTLECGO-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
NHHKFHYXRITNEY-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-phenyl-1,3-oxazolidine Chemical compound C1=CC(OC)=CC=C1C1NC(C=2C=CC=CC=2)OC1 NHHKFHYXRITNEY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
150000000703 Cerium Chemical class 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
241000220304 Prunus dulcis Species 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
150000001785 cerium compounds Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010918 diastereoselective addition Methods 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
229940081310 piperonal Drugs 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000037452 priming Effects 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005204 segregation Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229950005792 tenoate Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
238000003260 vortexing Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

SK1273-98A 1996-03-22 1997-03-17 Novel asymmetric synthesis of r-'alpha'-propyl-piperonyl amine and its analogs SK127398A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1395596P	1996-03-22	1996-03-22
PCT/US1997/003466 WO1997034887A1 (en)	1996-03-22	1997-03-17	NOVEL ASYMMETRIC SYNTHESIS OF R-α-PROPYL-PIPERONYL AMINE AND ITS ANALOGS

Publications (1)

Publication Number	Publication Date
SK127398A3 true SK127398A3 (en)	1999-04-13

Family

ID=21762727

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1273-98A SK127398A3 (en)	1996-03-22	1997-03-17	Novel asymmetric synthesis of r-'alpha'-propyl-piperonyl amine and its analogs

Country Status (23)

Country	Link
US (1)	US5932749A (pt)
EP (1)	EP0888329A1 (pt)
JP (1)	JP2000506891A (pt)
KR (1)	KR20000064735A (pt)
CN (1)	CN1218463A (pt)
AR (1)	AR006521A1 (pt)
AU (1)	AU719633B2 (pt)
BR (1)	BR9708233A (pt)
CA (1)	CA2249401A1 (pt)
CZ (1)	CZ295098A3 (pt)
EA (1)	EA001207B1 (pt)
EE (1)	EE9800299A (pt)
HR (1)	HRP970165A2 (pt)
IL (1)	IL126223A0 (pt)
LT (1)	LT4540B (pt)
LV (1)	LV12259B (pt)
NO (1)	NO984344L (pt)
NZ (1)	NZ331875A (pt)
PL (1)	PL329070A1 (pt)
SI (1)	SI9720023A (pt)
SK (1)	SK127398A3 (pt)
WO (1)	WO1997034887A1 (pt)
ZA (1)	ZA972342B (pt)

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WO2003022785A2 (en) *	2001-09-12	2003-03-20	Anormed Inc.	Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
TWI386395B (zh) *	2008-12-15	2013-02-21	Taigen Biotechnology Co Ltd	哌啶衍生物的立體有擇合成
AR090100A1 (es)	2012-02-21	2014-10-22	Celgene Corp	Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina
US9126906B2 (en)	2012-02-21	2015-09-08	Celgene Corporation	Asymmetric synthetic processes for the preparation of aminosulfone compounds
CN109069426B (zh)	2015-12-14	2021-10-29	X4 制药有限公司	治疗癌症的方法
WO2017106332A1 (en)	2015-12-14	2017-06-22	X4 Pharmaceuticals, Inc.	Methods for treating cancer
PL3393468T3 (pl)	2015-12-22	2023-01-23	X4 Pharmaceuticals, Inc.	Metody leczenia niedoboru odporności
US11337969B2 (en)	2016-04-08	2022-05-24	X4 Pharmaceuticals, Inc.	Methods for treating cancer
WO2017223243A1 (en)	2016-06-21	2017-12-28	X4 Pharmaceuticals, Inc.	Cxcr4 inhibitors and uses thereof
CN109640988A (zh)	2016-06-21	2019-04-16	X4 制药有限公司	Cxcr4抑制剂及其用途
ES2870920T3 (es)	2016-06-21	2021-10-28	X4 Pharmaceuticals Inc	Inhibidores de CXCR4 y usos de los mismos
US10548889B1 (en)	2018-08-31	2020-02-04	X4 Pharmaceuticals, Inc.	Compositions of CXCR4 inhibitors and methods of preparation and use
CA3171250A1 (en)	2020-03-10	2021-09-16	E. Lynne KELLEY	Methods for treating neutropenia
US12492178B2 (en)	2021-09-01	2025-12-09	Empathbio, Inc.	Stable polymorph of R-MDMA HCl
MX2024002291A (es)	2021-09-01	2024-06-28	Empathbio Inc	Sintesis de mdma o sus isomeros de mdma opticamente activos (r)- o (s).
WO2023044027A1 (en) *	2021-09-17	2023-03-23	ATAI Life Sciences AG	Preparation of optically active enantiomers of piperonyl amines by resolution of the diastereomeric salts
WO2023056102A1 (en)	2021-10-01	2023-04-06	ATAI Life Sciences AG	Novel prodrugs of mdma, mda, and derivatives thereof
US11912680B2 (en)	2021-12-28	2024-02-27	Empathbio, Inc.	Nitric oxide releasing prodrugs of MDA and MDMA

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DE3819438A1 (de) *	1987-06-30	1989-01-19	Basf Ag	Verfahren zur herstellung von optisch aktiven 1-arylethylaminen
IL99658A0 (en) *	1990-10-15	1992-08-18	Merck & Co Inc	Substituted azetidinones and pharmaceutical compositions containing them
US5149838A (en) *	1991-09-20	1992-09-22	Merck & Co., Inc.	Intermediates for substituted azetidinones useful as anti-inflammatory and antidegenerative agents

1997
- 1997-03-17 PL PL97329070A patent/PL329070A1/xx unknown
- 1997-03-17 SI SI9720023A patent/SI9720023A/sl unknown
- 1997-03-17 EP EP97914876A patent/EP0888329A1/en not_active Ceased
- 1997-03-17 BR BR9708233-3A patent/BR9708233A/pt unknown
- 1997-03-17 JP JP9533500A patent/JP2000506891A/ja active Pending
- 1997-03-17 EE EE9800299A patent/EE9800299A/xx unknown
- 1997-03-17 SK SK1273-98A patent/SK127398A3/sk unknown
- 1997-03-17 KR KR1019980707470A patent/KR20000064735A/ko not_active Withdrawn
- 1997-03-17 WO PCT/US1997/003466 patent/WO1997034887A1/en not_active Ceased
- 1997-03-17 NZ NZ331875A patent/NZ331875A/xx unknown
- 1997-03-17 IL IL12622397A patent/IL126223A0/xx unknown
- 1997-03-17 CA CA002249401A patent/CA2249401A1/en not_active Abandoned
- 1997-03-17 CZ CZ982950A patent/CZ295098A3/cs unknown
- 1997-03-17 EA EA199800844A patent/EA001207B1/ru not_active IP Right Cessation
- 1997-03-17 AU AU21968/97A patent/AU719633B2/en not_active Ceased
- 1997-03-17 CN CN97194596A patent/CN1218463A/zh active Pending
- 1997-03-18 ZA ZA972342A patent/ZA972342B/xx unknown
- 1997-03-21 AR ARP970101148A patent/AR006521A1/es unknown
- 1997-03-21 US US08/822,996 patent/US5932749A/en not_active Expired - Fee Related
- 1997-03-21 HR HR60/013,955A patent/HRP970165A2/xx not_active Application Discontinuation
1998
- 1998-09-18 NO NO984344A patent/NO984344L/no unknown
- 1998-09-18 LT LT98-132A patent/LT4540B/lt not_active IP Right Cessation
- 1998-09-21 LV LVP-98-185A patent/LV12259B/en unknown

Also Published As

Publication number	Publication date
HRP970165A2 (en)	1998-04-30
NZ331875A (en)	2000-01-28
ZA972342B (en)	1998-09-18
NO984344D0 (no)	1998-09-18
AU719633B2 (en)	2000-05-11
CA2249401A1 (en)	1997-09-25
LT4540B (lt)	1999-08-25
AR006521A1 (es)	1999-09-08
CZ295098A3 (cs)	1999-03-17
SI9720023A (sl)	1999-04-30
EA001207B1 (ru)	2000-12-25
JP2000506891A (ja)	2000-06-06
US5932749A (en)	1999-08-03
LV12259B (en)	1999-09-20
AU2196897A (en)	1997-10-10
EA199800844A1 (ru)	1999-02-25
CN1218463A (zh)	1999-06-02
WO1997034887A1 (en)	1997-09-25
BR9708233A (pt)	2000-01-04
LT98132A (en)	1999-03-25
PL329070A1 (en)	1999-03-15
KR20000064735A (ko)	2000-11-06
LV12259A (lv)	1999-04-20
NO984344L (no)	1998-09-18
EE9800299A (et)	1999-06-15
IL126223A0 (en)	1999-05-09
EP0888329A1 (en)	1999-01-07

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