HRP20120939T1 - Postupak za enantioselektivnu sintezu jednostrukih enantiomera derivata tio-supstituiranog arilmetansulfinila pomoä†u asimetriäśne oksidacije - Google Patents
Postupak za enantioselektivnu sintezu jednostrukih enantiomera derivata tio-supstituiranog arilmetansulfinila pomoä†u asimetriäśne oksidacije Download PDFInfo
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- HRP20120939T1 HRP20120939T1 HRP20120939TT HRP20120939T HRP20120939T1 HR P20120939 T1 HRP20120939 T1 HR P20120939T1 HR P20120939T T HRP20120939T T HR P20120939TT HR P20120939 T HRP20120939 T HR P20120939T HR P20120939 T1 HRP20120939 T1 HR P20120939T1
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- alkyl
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- whenever
- independently selected
- chiral ligand
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- 238000000034 method Methods 0.000 title claims 35
- 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 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 230000003647 oxidation Effects 0.000 title 1
- 238000007254 oxidation reaction Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000003446 ligand Substances 0.000 claims 12
- 229910052751 metal Inorganic materials 0.000 claims 11
- 239000002184 metal Substances 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 8
- -1 sulfoxide compound Chemical class 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000007800 oxidant agent Substances 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 150000003462 sulfoxides Chemical class 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000002736 metal compounds Chemical class 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- CFVMQQXRNGNVFQ-UHFFFAOYSA-N 2-sulfinylacetamide Chemical compound NC(=O)C=S=O CFVMQQXRNGNVFQ-UHFFFAOYSA-N 0.000 claims 1
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (34)
1. Postupak za dobivanje sulfoksidnog spoja sa formulom (I) bilo kao jednostrukog enantiomera ili u enantiomerno obogaćenom obliku :
[image]
pri čemu:
Ar je:
[image]
gdje:
X je veza, O, S(O)2, NH, OCH2, CH2NH, S(O2)NH;
R2 je odabran od H, F, Cl, Br, I, OR16, NR17R18, NHOH, NO2, CN, CF3, C1-C6 alkila, C2-C6 alkenila, C2-C6 alkinila, C3-C7 cikloalkila, C(=O)R16, CO2R16, OC(=O)R16 C(=O)NR17R18, NR15C(=O)R16NR15CO2R16, OC(=O)NR17R18 i NR15C(=S)R16; alternativno dvije R2 skupine se mogu kombinirati da tvore metilendioksi skupinu, etilendioksi skupinu; ili propilendioksi skupinu,
Ar1 je fenil proizvoljno supstituiran sa 0-5 R3;
C5-C10 cikloalkenil proizvoljno supstituiran sa 0-5 R3;
C5-C10 člana heteroarilna skupina proizvoljno supstituirana sa 0-5 R3, pri čemu navedeni heteroaril sadrži jedan, dva, ili tri heteroatoma koji su odabrani od N, O, S, ili Se; pri čemu:
R3 je odabran od H, F, Cl, Br, I, OR16, OCF3, NR17R18, NHOH, NO2, CN, CF3, CH2OR18, C1-C6 alkila, C2-C6 alkenila, C2-C6 alkinila, C3-C7 cikloalkila, 3-7 članog heterocikloalkila, fenila, 5 ili 6 članog heteroarila, C7-C10 arilalkila, C(=O)R16, CO2R16, OC(=O)R16, C(-O)NR17R18, NR15C(=O)R16, NR15CO2R16, OC(=O)NR17R18, NR15C(=S)R18, 1 NR15S(=O)2R16;
alternativno, dvije R3 skupine se mogu kombinirati da tvore metilendioksi skupinu, etilendioksi skupinu, ili propilendioksi skupinu;
Y je C1-C6 alkilen;
R1 je odabran od CN, C(=O)R14, CO2Rn, C(=O)NR12R13, C(-O)NR21OR22, C(=NR11)NR12R13, OC(=O)R11, OC(=O)NR12R13, NR12R13, NR21NR12R13, NR21C(=O)R14, NR21C(O)NR12R13, NR21S(O)2R11, NR21S(O)2NR12R13,
R1 uvijek kada se pojavljuje je neovisno odabran od H, C1-C6 alkila, C3-C7 cikloalkila, C3-C10 arila, arilalkila; pri čemu navedene alkilna, arilna, arilalkilna skupine su proizvoljno supstituirane sa jednom do tri R20 skupine;
R12 i R13 uvijek kada se pojavljuju su svaki neovisno odabrani od H, C1-C6 alkila, C6-C10 arila, i NR23R24, ili R12 i R13, zajedno sa dušikom na koji su spojeni, tvore 3-7 člani heterociklički prsten;
pri čemu navedene alkilna i arilna skupina i heterociklički prsten su proizvoljno supstituirani sa jednom do tri R20 skupine;
R14 uvijek kada se pojavljuje je neovisno odabran od C1-C6 alkila, C6-C10 arila, i arilalkila; pri čemu navedene alkilne, arilne i arilalkilne skupine su proizvoljno supstituirane sa jednom do tri R20 skupine;
R15 uvijek kada se pojavljuje je neovisno odabran od H, C1-C6 alkila;
R16 uvijek kada se pojavljuje je neovisno odabran od H, C1-C8 alkila, i C5-C10 arila; pri čemu navedene alkilna i arilna skupina su proizvoljno supstituirane sa jednom do tri R20 skupine;
R17 i R18 uvijek kada se pojavljuju su svaki neovisno odabrani od H, C1-C5 alkila i C6-C10 arila, ili R17 i R18, zajedno sa dušikom na koji su spojeni, tvore 3-7 člani heterociklički prsten;
pri čemu navedene alkilna i arilna skupina i heterociklički prsten su proizvoljno supstituirane sa jednom do dvije okso skupine;
R20 uvijek kada se pojavljuje je neovisno odabran od F, Cl, Br, I, OR22, NR23R24, NHOH, NO2, CN, CF3, C1-C6 alkila proizvoljno supstituiranog sa jednim do tri OH, C2-C6 alkenila, C2-C6 alkinila, C3-C7 cikloalkila, 3-7 članog hcterocikloalkila, fenila, supstituiran sa nula do jednim OR25, 5 ili 6 članog heteroarila, arilalkila, =O, C(-O)R22, CO2R22, OC(=O)R22, C(-O)NR23R24, NR21C(=O)R22, NR21CO2R22, te OC(=O)NR23R24;
R21 uvijek kada se pojavljuje je neovisno odabran od H i C1-C6, alkila;
R22 uvijek kada se pojavljuje je neovisno odabran od H, C1-C6 alkila, C1-C6 alkil-OH i C6-C10 arila;
R23 i R24 uvijek kada se pojavljuje su svaki neovisno odabrani od H, C1-C6 alkila, i C6-C10 arila, ili R23 i R24, zajedno sa dušikom na koji su spojeni, tvore 3-7 člani heterociklički prsten koji je proizvoljno supstituiran sa jednom do tri okso skupine;
R25 uvijek kada se pojavljuje je neovisno odabran od H, F, Cl, Br, C1-C8 alkila, i C1-C8 alkiloksi;
x je 1, 2, 3 ili 4;
naznačen time da sadrži korake:
a) kontakta pro-kiralnog sulfida sa formulom (II)
[image]
pri čemu Ar, Y i R1 su kako je gore definirano,
sa kompleksom titanijevog kiralnog liganda, bazom i oksidacijskim sredstvom u organskom otapalu; te proizvoljno
b) izolacije tako dobivenog sulfoksida sa formulom (I).
2. Postupak prema zahtjevu 1, naznačen time da Y je CH2 ili CH2CH2.
3. Postupak prema zahtjevu 1 ili 2, naznačen time da R1 je CN, C(=O)R14, CO2R11, C(=O)NR12R13, C(=O)NR2lOR22 i NR12R13.
4. Postupak prema zahtjevu 3, naznačen time da R1 je CN, CO2R1l, C(=O)NH2 ili C(=O)NHOH.
5. Postupak prema zahtjevu 1, naznačen time da R3 je odabran od F, Cl, Br, I.
6. Postupak prema bilo kojem od zahtjeva 1 do 5, naznačen time da R2 je H.
7. Postupak prema zahtjevu 1, naznačen time da metalni kiralni ligand je kompleks titanijevog dialkiltartrata.
8. Postupak prema zahtjevima 1 do 7, naznačen time da je metalni kiralni kompleks pripremljen od metalnog spoja, kiralnog liganda i vode.
9. Postupak prema zahtjevu 8, naznačen time da je kompleks metalnog kiralnog liganda pripremljen sa 0,1-1 ekvivalenata vode u odnosu na metalni spoj.
10. Postupak prema zahtjevu 9, naznačen time da je kompleks metalnog kiralnog liganda pripremljen sa 0,4-0,8 ekvivalenata vode u odnosu na metalni spoj.
11. Postupak prema zahtjevima 1 do 10, naznačen time da baza je tercijarni amin.
12. Postupak prema zahtjevu 11, naznačen time da tercijarni amin je diizopropiletilamin ili trietilamin.
13. Postupak prema zahtjevima 1 do 12, naznačen time da se korak a) provodi u prisutnosti od 0,01 do 2 ekvivalenta, poželjno od 0,05-0,5 ekvivalenata baze u odnosu na sulfid.
14. Postupak prema zahtjevu 13, naznačen time da se korak a) provodi u prisutnosti od 0,05-0,5 ekvivalenta baze u odnosu na sulfid.
15. Postupak prema zahtjevu 13 ili 14, naznačen time da se korak a) provodi u prisutnosti 0,1 do 0,3 ekvivalenta baze.
16. Postupak prema zahtjevima 13 ili 14, naznačen time da se korak a) provodi u prisutnosti 0,05-0,5 ekvivalenata kompleksa metalnog kiralnog liganda u odnosu na sulfid.
17. Postupak prema zahtjevu 16, naznačen time da se korak a) provodi u prisutnosti 0.1- 0,3 ekvivalenata kompleksa metalnog kiralnog liganda.
18. Postupak prema zahtjevima 1 do 17, naznačen time da se kompleks metalnog kiralnog liganda priprema na temperaturi između 20-70°C.
19. Postupak prema zahtjevu 18, naznačen time da se kompleks metalnog kiralnog liganda priprema na temperaturi između 40-60°C.
20. Postupak prema zahtjevu 19, naznačen time da se kompleks metalnog kiralnog liganda priprema na temperaturi između 50-55°C.
21. Postupak prema zahtjevima 1 do 20, naznačen time da se oksidacijsko sredstvo dovodi u kontakt sa sulfidom, kompleksom metalnog kiralnog liganda i bazom na temperaturi između 0-60°C.
22. Postupak prema zahtjevu 21, naznačen time da se oksidacijsko sredstvo dovodi u kontakt sa sulfidom, kompleksom metalnog kiralnog liganda i bazom na sobnoj temperaturi, koja je između 20-25°C.
23. Postupak prema zahtjevima 1 do 22, naznačen time da oksidacijsko sredstvo je vodikov peroksid, tert-butil hidroperoksid i kumen hidroperoksid.
24. Postupak prema zahtjevu 23, naznačen time da oksidacijsko sredstvo je kumen hidroperoksid.
25. Postupak prema zahtjevima 1 do 24, naznačen time da je dobiveni sulfoksid izravno izoliran pomoću filtracije.
26. Postupak prema zahtjevima 1 do 25, naznačen time da postupak nadalje sadrži korak kristalizacije produkta dobivenog u koraku b)
27. Postupak prema zahtjevu 26, naznačen time da se kristalizacija provodi u smjesi organskog otapala sa vodom.
28. Postupak prema zahtjevu 27, naznačen time da organsko otapalo je alkohol.
29. Postupak prema zahtjevu 27, naznačen time da voda predstavlja do 40 % volumenski smjese.
30. Postupak prema zahtjevu 26, naznačen time da kristalizacija je preferencijalna kristalizacija.
31. Postupak prema zahtjevima 1 do 30 naznačen time da je sulfoksid spoja sa formulom (I) dobiven sa enantiomernim viškom od barem 80 %.
32. Postupak prema zahtjevu 31, naznačen time da enantiomerni višak je barem 95 %.
33. Postupak prema zahtjevu 32, naznačen time da enantiomerni višak je barem 99 %.
34. Sulfoksid spoja sa formulom (I) naznačen time da je odabran od:
- (-) ili (+)-2-[2-(4-klorofenil)benzil]sulfmil acetamida;
- (-) ili (+) 2-[([1,1-bifenil]-2-ilmetil)sulfmil]acetamida;
- (-) ili (+) 2-[2-(3,4-diklorofenoksi)-benzil]sulfinil acetamida.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05290560A EP1702915A1 (en) | 2005-03-14 | 2005-03-14 | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
| US11/374,227 US7893111B2 (en) | 2005-03-14 | 2006-03-13 | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
| PCT/IB2006/000552 WO2006097814A1 (en) | 2005-03-14 | 2006-03-14 | Process for enantioselective synthesis of single enantiomers of thio-substituted arylmethanesulfinyl derivatives by asymmetric oxidation |
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| Publication Number | Publication Date |
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| HRP20120939T1 true HRP20120939T1 (hr) | 2013-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| HRP20120939TT HRP20120939T1 (hr) | 2005-03-14 | 2012-11-19 | Postupak za enantioselektivnu sintezu jednostrukih enantiomera derivata tio-supstituiranog arilmetansulfinila pomoä†u asimetriäśne oksidacije |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7893111B2 (hr) |
| EP (2) | EP1702915A1 (hr) |
| JP (2) | JP5192370B2 (hr) |
| KR (1) | KR101256881B1 (hr) |
| CN (1) | CN101142176B (hr) |
| AR (1) | AR053167A1 (hr) |
| AU (1) | AU2006224292B2 (hr) |
| BR (1) | BRPI0607968A2 (hr) |
| CA (1) | CA2599690C (hr) |
| DK (1) | DK1863760T3 (hr) |
| ES (1) | ES2392452T3 (hr) |
| HK (1) | HK1105950A1 (hr) |
| HR (1) | HRP20120939T1 (hr) |
| IL (1) | IL185585A (hr) |
| MX (1) | MX2007011159A (hr) |
| MY (1) | MY157717A (hr) |
| NO (1) | NO20074438L (hr) |
| NZ (1) | NZ560986A (hr) |
| SI (1) | SI1863760T1 (hr) |
| TW (1) | TWI364412B (hr) |
| WO (1) | WO2006097814A1 (hr) |
| ZA (1) | ZA200707267B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ2009172A3 (cs) * | 2009-03-17 | 2010-09-29 | Zentiva, K.S. | Zpusob výroby (S)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazolu |
| CN104447440B (zh) * | 2013-09-12 | 2016-05-18 | 中国科学院大连化学物理研究所 | 一种催化不对称氧化硫醚的方法 |
| SI3860998T1 (sl) | 2018-10-05 | 2024-06-28 | Annapurna Bio Inc. | Spojine in sestavki za zdravljenje stanj, povezanih z aktivnostjo apj-receptorja |
| CN110698482A (zh) * | 2019-10-29 | 2020-01-17 | 株洲千金药业股份有限公司 | 一种s型手性亚砜类化合物的制备方法 |
| CN110746428A (zh) * | 2019-10-29 | 2020-02-04 | 株洲千金药业股份有限公司 | 一种r型手性亚砜类化合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127722A (en) | 1975-10-02 | 1978-11-28 | Laboratoire L. Lafon | Benzhydrylsulphinyl derivatives |
| DE2708449C3 (de) | 1977-02-26 | 1981-01-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zum gleichmäßigen Färben von bahnförmigen Textilien aus modifizierten Polyesterfasern auf Baumfärbeapparaten |
| GB1584462A (en) | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2593809B1 (fr) * | 1986-01-31 | 1988-07-22 | Lafon Labor | Benzhydrylsulfinylacetamide, procede de preparation et utilisation en therapeutique |
| DE10224722C1 (de) | 2002-05-30 | 2003-08-14 | Leibniz Inst Fuer Festkoerper | Hochfeste, plastisch verformbare Formkörper aus Titanlegierungen |
| FR2849029B1 (fr) | 2002-12-20 | 2005-03-18 | Lafon Labor | Procede de preparation et formes cristallines des enantiomeres optiques du modafinil. |
| EP1437345A1 (en) | 2003-01-13 | 2004-07-14 | Organisation de Synthese Mondiale Orsymonde | Novel method for preparing methyl 2-diphenylmethylsulfinylacetate |
| EP1477476B1 (en) | 2003-05-16 | 2009-09-09 | Cephalon France | Modafinil synthesis process |
| EP1516869A1 (en) | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| US7297817B2 (en) * | 2004-04-13 | 2007-11-20 | Cephalon France | Thio-substituted arylmethanesulfinyl derivatives |
| US7449481B2 (en) * | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
| EP1586560A1 (en) * | 2004-04-13 | 2005-10-19 | Cephalon, Inc. | Thio-substituted arylmethanesulfinyl derivatives |
| US20060086667A1 (en) | 2004-09-13 | 2006-04-27 | Cephalon, Inc., U.S. Corporation | Methods for the separation of enantiomeric sulfinylacetamides |
| EP1634861A1 (en) | 2004-09-13 | 2006-03-15 | Cephalon, Inc. | Methods for the separation of modafinil |
-
2005
- 2005-03-14 EP EP05290560A patent/EP1702915A1/en not_active Withdrawn
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2006
- 2006-03-13 AR ARP060100957A patent/AR053167A1/es not_active Application Discontinuation
- 2006-03-13 US US11/374,227 patent/US7893111B2/en not_active Expired - Fee Related
- 2006-03-14 EP EP06710540A patent/EP1863760B1/en active Active
- 2006-03-14 MY MYPI20061095A patent/MY157717A/en unknown
- 2006-03-14 KR KR1020077023553A patent/KR101256881B1/ko not_active IP Right Cessation
- 2006-03-14 BR BRPI0607968-7A patent/BRPI0607968A2/pt not_active IP Right Cessation
- 2006-03-14 NZ NZ560986A patent/NZ560986A/en not_active IP Right Cessation
- 2006-03-14 SI SI200631473T patent/SI1863760T1/sl unknown
- 2006-03-14 MX MX2007011159A patent/MX2007011159A/es active IP Right Grant
- 2006-03-14 CN CN2006800082077A patent/CN101142176B/zh not_active Expired - Fee Related
- 2006-03-14 AU AU2006224292A patent/AU2006224292B2/en not_active Ceased
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- 2006-03-14 TW TW095108615A patent/TWI364412B/zh not_active IP Right Cessation
- 2006-03-14 JP JP2008501435A patent/JP5192370B2/ja not_active Expired - Fee Related
- 2006-03-14 DK DK06710540.3T patent/DK1863760T3/da active
- 2006-03-14 WO PCT/IB2006/000552 patent/WO2006097814A1/en not_active Application Discontinuation
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2007
- 2007-08-28 ZA ZA200707267A patent/ZA200707267B/xx unknown
- 2007-08-29 IL IL185585A patent/IL185585A/en not_active IP Right Cessation
- 2007-09-03 NO NO20074438A patent/NO20074438L/no not_active Application Discontinuation
- 2007-12-13 HK HK07113577.7A patent/HK1105950A1/xx not_active IP Right Cessation
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- 2012-10-02 JP JP2012220208A patent/JP5698201B2/ja not_active Expired - Fee Related
- 2012-11-19 HR HRP20120939TT patent/HRP20120939T1/hr unknown
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