ZA200306448B - New asymmetric process for the preparation of diaryl-methylpiperazines derivatives and novel asymmetric diarylmethylamines as intermediates. - Google Patents
New asymmetric process for the preparation of diaryl-methylpiperazines derivatives and novel asymmetric diarylmethylamines as intermediates. Download PDFInfo
- Publication number
- ZA200306448B ZA200306448B ZA200306448A ZA200306448A ZA200306448B ZA 200306448 B ZA200306448 B ZA 200306448B ZA 200306448 A ZA200306448 A ZA 200306448A ZA 200306448 A ZA200306448 A ZA 200306448A ZA 200306448 B ZA200306448 B ZA 200306448B
- Authority
- ZA
- South Africa
- Prior art keywords
- general formula
- compound
- give
- defined above
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000000543 intermediate Substances 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- -1 2-nitrobenzenesulfonyl group Chemical group 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000010306 acid treatment Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- CESUXLKAADQNTB-SSDOTTSWSA-N 2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@](N)=O CESUXLKAADQNTB-SSDOTTSWSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- CESUXLKAADQNTB-ZETCQYMHSA-N 2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](N)=O CESUXLKAADQNTB-ZETCQYMHSA-N 0.000 claims 2
- XRNBLQCAFWFFPM-UHFFFAOYSA-N 4-iodobenzamide Chemical class NC(=O)C1=CC=C(I)C=C1 XRNBLQCAFWFFPM-UHFFFAOYSA-N 0.000 claims 2
- NQICGNSARVCSGJ-BFNFPZTMSA-N [(1s,2r,5s)-5-methyl-2-propan-2-ylcyclohexyl] 4-methylbenzenesulfinate Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1OS(=O)C1=CC=C(C)C=C1 NQICGNSARVCSGJ-BFNFPZTMSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 7
- 238000011914 asymmetric synthesis Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 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 abstract description 3
- 230000029936 alkylation Effects 0.000 abstract description 3
- 238000005804 alkylation reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000002902 organometallic compounds Chemical class 0.000 abstract description 3
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 3
- 238000003776 cleavage reaction Methods 0.000 abstract description 2
- 230000007017 scission Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000002346 iodo group Chemical group I* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical group OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 238000006140 methanolysis reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ZZCMDNFADQTVQF-UHFFFAOYSA-N 4-[amino(quinolin-8-yl)methyl]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1C(N)C1=CC=CC2=CC=CN=C12 ZZCMDNFADQTVQF-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 1
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- QJCPEOFEBREKQB-UHFFFAOYSA-N benzenesulfinamide Chemical compound NS(=O)C1=CC=CC=C1 QJCPEOFEBREKQB-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010918 diastereoselective addition Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QPRRTJHYSKVXSM-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N(CCCl)CCCl QPRRTJHYSKVXSM-UHFFFAOYSA-N 0.000 description 1
- FMPWFHQUILGARU-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)N(CCCl)CCCl FMPWFHQUILGARU-UHFFFAOYSA-N 0.000 description 1
- GHOMPHXKTJFWCV-UHFFFAOYSA-N n,n-diethyl-4-iodobenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(I)C=C1 GHOMPHXKTJFWCV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0100764A SE0100764D0 (sv) | 2001-03-07 | 2001-03-07 | New assymetric process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306448B true ZA200306448B (en) | 2004-09-08 |
Family
ID=20283236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306448A ZA200306448B (en) | 2001-03-07 | 2003-08-19 | New asymmetric process for the preparation of diaryl-methylpiperazines derivatives and novel asymmetric diarylmethylamines as intermediates. |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7045625B2 (pt) |
| EP (1) | EP1368325B1 (pt) |
| JP (1) | JP2004522793A (pt) |
| KR (1) | KR100856996B1 (pt) |
| CN (2) | CN1244565C (pt) |
| AT (1) | ATE406354T1 (pt) |
| BR (1) | BR0207817A (pt) |
| CA (1) | CA2440104A1 (pt) |
| DE (1) | DE60228548D1 (pt) |
| DK (1) | DK1368325T3 (pt) |
| ES (1) | ES2311050T3 (pt) |
| HK (1) | HK1059436A1 (pt) |
| IL (1) | IL157460A0 (pt) |
| MX (1) | MXPA03007889A (pt) |
| NO (1) | NO325156B1 (pt) |
| NZ (1) | NZ527656A (pt) |
| PT (1) | PT1368325E (pt) |
| SE (1) | SE0100764D0 (pt) |
| SI (1) | SI1368325T1 (pt) |
| WO (1) | WO2002070492A1 (pt) |
| ZA (1) | ZA200306448B (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560781A (zh) * | 2022-03-01 | 2022-05-31 | 无锡捷化医药科技有限公司 | 一种n,n-二(2-氯乙基)-4-硝基苯基丙氨酸甲酯的制备方法 |
| CN114702457A (zh) * | 2022-03-30 | 2022-07-05 | 青岛科技大学 | 一种二芳基甲胺类化合物的绿色合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202238D0 (en) * | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
| DK0711289T3 (da) * | 1993-07-30 | 2000-11-06 | Delta Pharmaceuticals Inc | Piperazinforbindelser til anvendelse i terapi |
| SE9504661D0 (sv) * | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| SE9904673D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE0001209D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
-
2001
- 2001-03-07 SE SE0100764A patent/SE0100764D0/xx unknown
-
2002
- 2002-03-05 EP EP02701852A patent/EP1368325B1/en not_active Expired - Lifetime
- 2002-03-05 PT PT02701852T patent/PT1368325E/pt unknown
- 2002-03-05 SI SI200230739T patent/SI1368325T1/sl unknown
- 2002-03-05 MX MXPA03007889A patent/MXPA03007889A/es active IP Right Grant
- 2002-03-05 KR KR1020037011675A patent/KR100856996B1/ko not_active IP Right Cessation
- 2002-03-05 BR BR0207817-1A patent/BR0207817A/pt not_active IP Right Cessation
- 2002-03-05 DK DK02701852T patent/DK1368325T3/da active
- 2002-03-05 CN CNB028060326A patent/CN1244565C/zh not_active Expired - Fee Related
- 2002-03-05 JP JP2002569812A patent/JP2004522793A/ja active Pending
- 2002-03-05 WO PCT/SE2002/000376 patent/WO2002070492A1/en active IP Right Grant
- 2002-03-05 CN CNB2005100879382A patent/CN1295217C/zh not_active Expired - Fee Related
- 2002-03-05 IL IL15746002A patent/IL157460A0/xx unknown
- 2002-03-05 DE DE60228548T patent/DE60228548D1/de not_active Expired - Fee Related
- 2002-03-05 CA CA002440104A patent/CA2440104A1/en not_active Abandoned
- 2002-03-05 AT AT02701852T patent/ATE406354T1/de not_active IP Right Cessation
- 2002-03-05 US US10/468,989 patent/US7045625B2/en not_active Expired - Fee Related
- 2002-03-05 NZ NZ527656A patent/NZ527656A/en unknown
- 2002-03-05 ES ES02701852T patent/ES2311050T3/es not_active Expired - Lifetime
-
2003
- 2003-08-19 ZA ZA200306448A patent/ZA200306448B/en unknown
- 2003-09-05 NO NO20033944A patent/NO325156B1/no not_active IP Right Cessation
-
2004
- 2004-03-26 HK HK04102254.3A patent/HK1059436A1/xx not_active IP Right Cessation
-
2005
- 2005-11-22 US US11/285,672 patent/US7423154B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SE0100764D0 (sv) | 2001-03-07 |
| CN1721407A (zh) | 2006-01-18 |
| HK1059436A1 (en) | 2004-07-02 |
| JP2004522793A (ja) | 2004-07-29 |
| NO325156B1 (no) | 2008-02-11 |
| PT1368325E (pt) | 2008-10-27 |
| NO20033944D0 (no) | 2003-09-05 |
| US7423154B2 (en) | 2008-09-09 |
| DK1368325T3 (da) | 2008-11-24 |
| CN1494532A (zh) | 2004-05-05 |
| NO20033944L (no) | 2003-10-31 |
| US7045625B2 (en) | 2006-05-16 |
| KR20030080075A (ko) | 2003-10-10 |
| DE60228548D1 (de) | 2008-10-09 |
| CA2440104A1 (en) | 2002-09-12 |
| NZ527656A (en) | 2005-04-29 |
| MXPA03007889A (es) | 2003-12-04 |
| CN1295217C (zh) | 2007-01-17 |
| IL157460A0 (en) | 2004-03-28 |
| ES2311050T3 (es) | 2009-02-01 |
| ATE406354T1 (de) | 2008-09-15 |
| EP1368325B1 (en) | 2008-08-27 |
| EP1368325A1 (en) | 2003-12-10 |
| SI1368325T1 (sl) | 2008-12-31 |
| WO2002070492A1 (en) | 2002-09-12 |
| BR0207817A (pt) | 2004-03-09 |
| US20060074238A1 (en) | 2006-04-06 |
| KR100856996B1 (ko) | 2008-09-04 |
| US20040077861A1 (en) | 2004-04-22 |
| CN1244565C (zh) | 2006-03-08 |
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