Process for preparing scopine esters
First Claim
Patent Images
1. A process for preparing a compound of formula 1 from a compound of formula 2
the process comprising reacting in one step the compound of formula 2 with a compound of formula 3
wherein:
- X−
is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate;
R1 is hydroxy, C1-C4-alkyl, C1-C4-alkoxy, CF3, or fluorine;
Ar is phenyl, naphthyl, thienyl, and furyl, each optionally mono- or disubstituted with one or two groups selected from C1-C4-alkyl, C1-C4-alkoxy, hydroxy, fluorine, chlorine, bromine, or CF3;
Y−
is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate; and
R is hydroxy, methoxy, ethoxy, O—
N-succinimide, O—
N-phthalimide, phenyloxy, nitrophenyloxy, fluorophenyloxy, pentafluorophenyloxy, vinyloxy, 2-allyloxy, —
S-methyl, —
S-ethyl, or —
S-phenyl.
2 Assignments
0 Petitions
Accused Products
Abstract
A process for preparing a compound of formula 1
from a compound of formula 2
the process comprising reacting in one step the compound of formula 2 with a compound of formula 3
wherein:
X− is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate;
R1 is hydroxy, C1-C4-alkyl, C1-C4-alkoxy, CF3, or fluorine;
Ar is phenyl, naphthyl, thienyl, and furyl, each optionally mono- or disubstituted with one or two groups selected from C1-C4-alkyl, C1-C4-alkoxy, hydroxy, fluorine, chlorine, bromine, or CF3;
Y− is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate; and
R is hydroxy, methoxy, ethoxy, O—N-succinimide, O—N-phthalimide, phenyloxy, nitrophenyloxy, fluorophenyloxy, pentafluorophenyloxy, vinyloxy, 2-allyloxy, —S-methyl, —S-ethyl, or —S-phenyl.
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Citations
25 Claims
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1. A process for preparing a compound of formula 1
from a compound of formula 2 the process comprising reacting in one step the compound of formula 2 with a compound of formula 3 wherein: -
X−
is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate;
R1 is hydroxy, C1-C4-alkyl, C1-C4-alkoxy, CF3, or fluorine;
Ar is phenyl, naphthyl, thienyl, and furyl, each optionally mono- or disubstituted with one or two groups selected from C1-C4-alkyl, C1-C4-alkoxy, hydroxy, fluorine, chlorine, bromine, or CF3;
Y−
is chlorine, bromine, iodine, methanesulfonate, or trifluoromethanesulfonate; and
R is hydroxy, methoxy, ethoxy, O—
N-succinimide, O—
N-phthalimide, phenyloxy, nitrophenyloxy, fluorophenyloxy, pentafluorophenyloxy, vinyloxy, 2-allyloxy, —
S-methyl, —
S-ethyl, or —
S-phenyl.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25)
X−
is bromine, methanesulfonate, or trifluoromethanesulfonate;
R1 is hydroxy, methyl, CF3, or fluorine;
Ar is phenyl, thienyl, or furyl;
Y−
is bromine, methanesulfonate, or trifluoromethanesulfonate; and
R is hydroxy, O—
N-succinimide, O—
N-phthalimide, vinyloxy, or 2-allyloxy.
-
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3. The process according to claim 1, wherein:
-
X−
is bromine, methanesulfonate, or trifluoromethanesulfonate;
R1 is hydroxy or methyl;
Ar is phenyl or thienyl;
Y−
is bromine, methanesulfonate, or trifluoromethanesulfonate; and
R is hydroxy, O—
N-succinimide, O—
N-phthalimide, vinyloxy, or 2-allyloxy.
-
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4. The process according to claim 3, wherein R is vinyloxy or 2-allyloxy.
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5. The process according to claim 1, wherein the reaction is carried out in an organic solvent selected from acetonitrile, nitromethane, formamide, dimethylformamide, N-methylpyrrolidinone, dimethylsulfoxide, or dimethylacetamide.
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6. The process according to claim 2, wherein the reaction is carried out in an organic solvent selected from acetonitrile, nitromethane, formamide, dimethylformamide, N-methylpyrrolidinone, dimethylsulfoxide, or dimethylacetamide.
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7. The process according to claim 3, wherein the reaction is carried out in an organic solvent selected from acetonitrile, nitromethane, formamide, dimethylformamide, N-methylpyrrolidinone, dimethylsulfoxide, or dimethylacetamide.
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8. The process according to claim 4, wherein the reaction is carried out in an organic solvent selected from acetonitrile, nitromethane, formamide, dimethylformamide, N-methylpyrrolidinone, dimethylsulfoxide, or dimethylacetamide.
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9. The process according to claim 1, wherein R is hydroxy and activating reagents selected from carbonyldiimidazole, carbonyldi-1,2,4-triazole, dicyclohexylcarbodiimide, and ethyldimethylaminopropylcarbodiimide are used.
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10. The process according to claim 2, wherein R is hydroxy and activating reagents selected from carbonyldiimidazole, carbonyldi-1,2,4-triazole, dicyclohexylcarbodiimide, and ethyldimethylaminopropylcarbodiimide are used.
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11. The process according to claim 3, wherein R is hydroxy and activating reagents selected from carbonyldiimidazole, carbonyldi-1,2,4-triazole, dicyclohexyl carbodiimide, and ethyldimethylaminopropylcarbodiimide are used.
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12. The process according to claim 4, wherein R is hydroxy and activating reagents selected from carbonyldiimidazole, carbonyldi-1,2,4-triazole, dicyclohexyl carbodiimide, and ethyldimethylaminopropylcarbodiimide are used.
-
13. The process according to claim 1, wherein the reaction is carried out at a temperature below 30°
- C.
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14. The process according to claim 1, wherein the reaction is carried out at a temperature between −
- 20°
C. and 20°
C.
- 20°
-
15. The process according to claim 2, wherein the reaction is carried out at a temperature between −
- 20°
C. and 20°
C.
- 20°
-
16. The process according to claim 3, wherein the reaction is carried out at a temperature between −
- 20°
C. and 20°
C.
- 20°
-
17. The process according to claim 4, wherein the reaction is carried out at a temperature between −
- 20°
C. and 20°
C.
- 20°
-
18. The process according to claim 1, wherein the reaction is carried out in the presence of an organic or inorganic base.
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19. The process according to claim 2, wherein the reaction is carried out in the presence of an organic or inorganic base.
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20. The process according to claim 3, wherein the reaction is carried out in the presence of an organic or inorganic base.
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21. The process according to claim 4, wherein the reaction is carried out in the presence of an organic or inorganic base.
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22. The process according to claim 1, wherein R1 is hydroxy and the reaction is carried out in the presence of zeolites as catalyst.
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23. The process according to claim 2, wherein R1 is hydroxy and the reaction is carried out in the presence of zeolites as catalyst.
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24. The process according to claim 3, wherein R1 is hydroxy and the reaction is carried out in the presence of zeolites as catalyst.
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25. The process according to claim 4, wherein R1 is hydroxy and the reaction is carried out in the presence of zeolites as catalyst.
Specification
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Current AssigneeBoehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
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Original AssigneeBoehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
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InventorsPfrengle, Waldemar Franz-Augustin, Rall, Werner, Brandenburg, Joerg
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Primary Examiner(s)Huang, Evelyn Mei
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Application NumberUS10/339,480Publication NumberTime in Patent Office516 DaysField of Search546/91, 549/59, 549/60, 549/473, 560/100, 560/101, 562/468US Class Current546/91CPC Class CodesA61P 11/00 Drugs for disorders of the ...A61P 11/06 AntiasthmaticsC07D 451/10 acylated by aliphatic or ar...
