LT4540B - Nauja r- -propilpiperonilamino ir jo analogų asimetrinė sintezė - Google Patents
Nauja r- -propilpiperonilamino ir jo analogų asimetrinė sintezė Download PDFInfo
- Publication number
- LT4540B LT4540B LT98-132A LT98132A LT4540B LT 4540 B LT4540 B LT 4540B LT 98132 A LT98132 A LT 98132A LT 4540 B LT4540 B LT 4540B
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- Lithuania
- Prior art keywords
- compound
- acid
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- alcohol
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- 238000011914 asymmetric synthesis Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 150
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 238000005984 hydrogenation reaction Methods 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 26
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 14
- 229910052684 Cerium Inorganic materials 0.000 claims description 12
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000003993 interaction Effects 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical group OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- QDMNKWNMUHNQNU-UHFFFAOYSA-I [Br-].[Mg+2].[Al+3].[Br-].[Br-].[Br-].[Br-] Chemical compound [Br-].[Mg+2].[Al+3].[Br-].[Br-].[Br-].[Br-] QDMNKWNMUHNQNU-UHFFFAOYSA-I 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003892 tartrate salts Chemical class 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 20
- 239000000543 intermediate Substances 0.000 abstract description 9
- 239000003602 elastase inhibitor Substances 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- -1 1,3-Benzodioxol-5-yl Chemical group 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- CAJNAUPLBUPIRU-CQSZACIVSA-N 1-(1,3-benzodioxol-5-yl)-n-[(1r)-1-phenylethyl]butan-1-imine Chemical compound C1([C@@H](C)N=C(CCC)C=2C=C3OCOC3=CC=2)=CC=CC=C1 CAJNAUPLBUPIRU-CQSZACIVSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 7
- 150000002466 imines Chemical class 0.000 description 7
- JJVFJKLPESJUDV-SBSPUUFOSA-N (1r)-1-(1,3-benzodioxol-5-yl)butan-1-amine;hydrochloride Chemical compound Cl.CCC[C@@H](N)C1=CC=C2OCOC2=C1 JJVFJKLPESJUDV-SBSPUUFOSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
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- IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 3
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
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- 238000001953 recrystallisation Methods 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- 239000011780 sodium chloride Substances 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
- 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
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PTBSGTKWHOOAEH-UHFFFAOYSA-I aluminum;magnesium;pentachloride Chemical compound [Mg+2].[Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-] PTBSGTKWHOOAEH-UHFFFAOYSA-I 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
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
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- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 230000006340 racemization Effects 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
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- 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 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003466 welding 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1395596P | 1996-03-22 | 1996-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT98132A LT98132A (en) | 1999-03-25 |
| LT4540B true LT4540B (lt) | 1999-08-25 |
Family
ID=21762727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT98-132A LT4540B (lt) | 1996-03-22 | 1998-09-18 | Nauja r- -propilpiperonilamino ir jo analogų asimetrinė sintezė |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5932749A (cs) |
| EP (1) | EP0888329A1 (cs) |
| JP (1) | JP2000506891A (cs) |
| KR (1) | KR20000064735A (cs) |
| CN (1) | CN1218463A (cs) |
| AR (1) | AR006521A1 (cs) |
| AU (1) | AU719633B2 (cs) |
| BR (1) | BR9708233A (cs) |
| CA (1) | CA2249401A1 (cs) |
| CZ (1) | CZ295098A3 (cs) |
| EA (1) | EA001207B1 (cs) |
| EE (1) | EE9800299A (cs) |
| HR (1) | HRP970165A2 (cs) |
| IL (1) | IL126223A0 (cs) |
| LT (1) | LT4540B (cs) |
| LV (1) | LV12259B (cs) |
| NO (1) | NO984344L (cs) |
| NZ (1) | NZ331875A (cs) |
| PL (1) | PL329070A1 (cs) |
| SI (1) | SI9720023A (cs) |
| SK (1) | SK127398A3 (cs) |
| WO (1) | WO1997034887A1 (cs) |
| ZA (1) | ZA972342B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5587299A (en) | 1998-08-31 | 2000-03-21 | Du Pont Pharmaceuticals Company | An efficient process for the preparation of a human leukocyte elastase inhibitor |
| CN1272322C (zh) * | 2001-09-12 | 2006-08-30 | 阿诺麦德股份有限公司 | 对映体纯的氨基取代稠合双环的合成 |
| NZ592831A (en) * | 2008-12-15 | 2013-06-28 | Taigen Biotechnology Co Ltd | Stereoselective synthesis of piperidine derivatives |
| US9126906B2 (en) | 2012-02-21 | 2015-09-08 | Celgene Corporation | Asymmetric synthetic processes for the preparation of aminosulfone compounds |
| AR090100A1 (es) | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| CN109069486A (zh) | 2015-12-14 | 2018-12-21 | X4 制药有限公司 | 治疗癌症的方法 |
| WO2017106328A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| US10610527B2 (en) | 2015-12-22 | 2020-04-07 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| WO2017177230A1 (en) | 2016-04-08 | 2017-10-12 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| EP3471727B1 (en) | 2016-06-21 | 2020-12-09 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| US10988465B2 (en) | 2016-06-21 | 2021-04-27 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| US11332470B2 (en) | 2016-06-21 | 2022-05-17 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| CN115515585A (zh) | 2020-03-10 | 2022-12-23 | X4 制药有限公司 | 用于治疗中性粒细胞减少症的方法 |
| EP4396305A4 (en) | 2021-09-01 | 2025-08-27 | Empathbio Inc | SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE ISOMERS (R)- OR (S)-MDMA |
| US20230109467A1 (en) * | 2021-09-17 | 2023-04-06 | ATAI Life Sciences AG | Preparation of optically active enantiomers of piperonyl amines by resolution of the diastereomeric salts |
| US11845736B2 (en) | 2021-10-01 | 2023-12-19 | Empathbio, Inc. | Prodrugs of MDMA, MDA, and derivatives thereof |
| EP4457222A2 (en) | 2021-12-28 | 2024-11-06 | EmpathBio, Inc. | Nitric oxide releasing prodrugs of mda and mdma |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0481671A1 (en) | 1990-10-15 | 1992-04-22 | Merck & Co. Inc. | New substituted azetidinones as anti-inflammatory and antidegenerative agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3819438A1 (de) * | 1987-06-30 | 1989-01-19 | Basf Ag | Verfahren zur herstellung von optisch aktiven 1-arylethylaminen |
| 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 IL IL12622397A patent/IL126223A0/xx unknown
- 1997-03-17 SI SI9720023A patent/SI9720023A/sl unknown
- 1997-03-17 KR KR1019980707470A patent/KR20000064735A/ko not_active Withdrawn
- 1997-03-17 BR BR9708233-3A patent/BR9708233A/pt unknown
- 1997-03-17 EP EP97914876A patent/EP0888329A1/en not_active Ceased
- 1997-03-17 SK SK1273-98A patent/SK127398A3/sk unknown
- 1997-03-17 AU AU21968/97A patent/AU719633B2/en not_active Ceased
- 1997-03-17 NZ NZ331875A patent/NZ331875A/xx unknown
- 1997-03-17 PL PL97329070A patent/PL329070A1/xx unknown
- 1997-03-17 EE EE9800299A patent/EE9800299A/xx unknown
- 1997-03-17 CA CA002249401A patent/CA2249401A1/en not_active Abandoned
- 1997-03-17 CN CN97194596A patent/CN1218463A/zh active Pending
- 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 WO PCT/US1997/003466 patent/WO1997034887A1/en not_active Application Discontinuation
- 1997-03-17 JP JP9533500A patent/JP2000506891A/ja active Pending
- 1997-03-18 ZA ZA972342A patent/ZA972342B/xx unknown
- 1997-03-21 US US08/822,996 patent/US5932749A/en not_active Expired - Fee Related
- 1997-03-21 AR ARP970101148A patent/AR006521A1/es unknown
- 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0481671A1 (en) | 1990-10-15 | 1992-04-22 | Merck & Co. Inc. | New substituted azetidinones as anti-inflammatory and antidegenerative agents |
Non-Patent Citations (4)
| Title |
|---|
| ELEVELD M B, HOGEVEEN H, SCHUDDE E P.: "Diastereoselective synthesis of chiral secondary amines with two chiral centers directly attached to the nitrogen atom", J ORG CHEM., 1986, pages 3635, XP002005655, DOI: doi:10.1021/jo00369a016 |
| GERHARD BRINGMANN ET AL.: "Chiral building blocks for the synthesis of nitrogen-containing natural products, 5. The enantioselective synthesis of optically active, benzene nucleus-substituted 1-phenylethylamines from the corresponding acetophenones", LIEBIGS ANNALEN DER CHEMIE, 1990, pages 795 |
| MING JUNG WU, LENDON N. PRIDGEN: "Synthesis of chiral .alpha.-alkyl phenethylamines via organometallic addition to chiral 2-aryl-1,3-oxazolidines", J. ORG. CHEM., 1991, pages 1340 |
| YUTAKA UKAJI ET AL.: "Diastereofacial Discrimination in the Reaction of Chiral Alkoxymethyl Oxime Ethers with Allyl Metallic Reagents", CHEMISTRY LETTERS, 1991, pages 173 |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ295098A3 (cs) | 1999-03-17 |
| LV12259A (lv) | 1999-04-20 |
| NO984344D0 (no) | 1998-09-18 |
| US5932749A (en) | 1999-08-03 |
| CN1218463A (zh) | 1999-06-02 |
| HRP970165A2 (en) | 1998-04-30 |
| EP0888329A1 (en) | 1999-01-07 |
| JP2000506891A (ja) | 2000-06-06 |
| NO984344L (no) | 1998-09-18 |
| SI9720023A (sl) | 1999-04-30 |
| KR20000064735A (ko) | 2000-11-06 |
| EA199800844A1 (ru) | 1999-02-25 |
| ZA972342B (en) | 1998-09-18 |
| NZ331875A (en) | 2000-01-28 |
| LV12259B (en) | 1999-09-20 |
| WO1997034887A1 (en) | 1997-09-25 |
| EA001207B1 (ru) | 2000-12-25 |
| IL126223A0 (en) | 1999-05-09 |
| BR9708233A (pt) | 2000-01-04 |
| AR006521A1 (es) | 1999-09-08 |
| LT98132A (en) | 1999-03-25 |
| PL329070A1 (en) | 1999-03-15 |
| AU719633B2 (en) | 2000-05-11 |
| CA2249401A1 (en) | 1997-09-25 |
| AU2196897A (en) | 1997-10-10 |
| SK127398A3 (en) | 1999-04-13 |
| EE9800299A (et) | 1999-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 20010317 |