Process for the Manufacture of Non-Steroidal Anti-Inflammatory Agents and Intermediates Thereof
AssigneeIntendis GmbH
InventorSteffen SCHWEIZER
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Abstract
The current invention describes novel chiral synthetic routes and intermediates for the manufacture of chiral anti-inflammatory agents of general formula VIII in which at least one of the groups X1, X2, X3 is selected from fluoro, chloro, bromo, hydroxy, methoxy, ethoxy, trifluoromethyl, amino whereas the other groups X1, X2, X3 have the meaning of a hydrogen atom, in which at least one of the groups Z1, Z2, Z3 is selected from —O—, —S—, —N(—CH3)—, whereas the other groups Z1, Z2, Z3 have the meaning of a —CH2— group, and in which Ar is an aromatic group.
Claims27
-18. (canceled)
A process for producing a compound according to formula VIII
- in which at least one of the groups X1, X2, X3 is fluoro, chloro, bromo, hydroxy, methoxy, ethoxy, trifluoromethyl or amino
- and the other groups X1, X2, X3 are hydrogen,
- and in which at least one of the groups Z1, Z2, Z3 is —O—, —S—, —NH—, or —N(—CH3)—, and the other groups Z1, Z2, Z3 are —CH2— groups
- and in which Ar stands for an aromatic group comprising reducing an enantiomerically pure imine of formula VII
- in which
- at least one of the groups X1, X2, X3 is fluoro, chloro, bromo, hydroxy, methoxy, ethoxy, trifluoromethyl or amino and the other groups X1, X2, X3 are hydrogen,
- and in which at least one of the groups Z1, Z2, Z3 is —O—, —S—, —NH— or —N(—CH3)—, and the other groups Z1, Z2, Z3 are —CH2— groups
- and in which Ar stands for an aromatic group.
An enantiomerically pure compound of formula I
- wherein:
- Z1
- Z2
- Z3
- X1
- X2
- X3
- enantiomer
- a)
- O
- F
- R
- b)
- O
- F
- R
- c)
- O
- F
- R
- d)
- NH
- F
- R
- e)
- S
- F
- R
- f)
- NH
- Cl
- R
- g)
- NH
- Cl
- R
- h)
- S
- Cl
- R
- i)
- S
- CF3
- R
- j)
- S
- CF3
- R
- k)
- O
- CF3
- R
- l)
- O
- O—CH3
- R
- m)
- O
- O—CH3
- R
- n)
- O
- O
- O—CH3
- R
- o)
- O
- F
- R
- p)
- NH
- F
- R
- q)
- NH
- NH2
- R
- r)
- NH
- NH2
- R
- s)
- O
- Br
- R
- t)
- O
- F
- S
- u)
- O
- F
- S
- v)
- O
- F
- S
- w)
- NH
- F
- S
- x)
- S
- F
- S
- y)
- NH
- Cl
- S
- z)
- NH
- Cl
- S
- aa)
- S
- Cl
- S
- bb)
- S
- CF3
- S
- cc)
- S
- CF3
- S
- dd)
- O
- CF3
- S
- ee)
- O
- O—CH3
- S
- ff)
- O
- O—CH3
- S
- gg)
- O
- O
- O—CH3
- S
- hh)
- O
- F
- S
- ii)
- NH
- F
- S
- jj)
- NH
- NH2
- S
- kk)
- NH
- NH2
- S
- ll)
- O
- Br
- S.
Dependencies are inferred from the claim text.