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US4404150A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyclic pyrophosphate derivatives and their preparation

Assignee: Sankin Industry Co Ltd
•
Filing: 1981-02-05
•
Granted: 1983-09-13
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Expires: 2001-02-05
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Abstract

Abstract A cyclic pyrophosphate derivative having the formula ##STR1## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents alkyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; a method of preparing the same, a dental filling material comprising the same and a method of filling dental cavities are disclosed.

Inventors

  • 👤 Masayoshi Tsunekawa
  • 👤 Nobuyoshi Miyoshi
  • 👤 Tamotsu Komura

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 23:23
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6578; C07F9/06; C07F9/08; C07F9/09; C07F9/098; C07F9/6571; C07F9/6574

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 73 words
A cyclic pyrophosphate derivative having the formula (I): ##STR24## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy.
Claim 2
Dependent Claim 73 words
A cyclic pyrophosphate derivative having the formula (I): ##STR24## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy.
Claim 3
Dependent Claim 18 words
The cyclic pyrophosphate according to claim 1, wherein A is a direct bond between the two penyl rings.
Claim 4
Dependent Claim 12 words
The cyclic pyrophosphate according to claim 1, wherein A is dimethyl methylene.
Claim 5
Dependent Claim 12 words
The cyclic pyrophosphate according to claim 1, wherein A is phenyl methylene.
Claim 6
Dependent Claim 11 words
The cyclic pyrophosphate according to claim 1, wherein A is sulfonyl.
Claim 7
Dependent Claim 11 words
The cyclic pyrophosphate according to claim 1, wherein A is oxy.
Claim 8
Dependent Claim 11 words
The cyclic pyrophosphate according to claim 1, wherein A is cyclohexylidene.
Claim 9
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein every R 2 is hydrogen.
Claim 10
Dependent Claim 16 words
The cyclic pyrophosphate according to claim 1, wherein two of the R 2 groups are halogen.
Claim 11
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein every R 2 is halogen.
Claim 12
Dependent Claim 12 words
The cyclic pyropshophate according to claim 1, wherein R 1 is allyl.
Claim 13
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 2-methacryloyloxy ethyl.
Claim 14
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 1-methyl-2-methacryloyloxy ethyl.
Claim 15
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is 2-halo-3-methacryloyloxy ethyl.
Claim 16
Dependent Claim 13 words
The cyclic pyrophosphate according to claim 1, wherein R 1 is acryloyloxy ethyl.
Claim 17
Dependent Claim 163 words
A process for the production of cyclic pyrophosphate derivatives having the formula (I) ##STR25## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; the process comprising: reacting, under anhydrous conditions, a phenol derivative having the formula (II) ##STR26## with a phosphoryl halide to give the phosphoryl dihalide derivative having the formula (III) ##STR27## wherein X is halogen; adding to the phosphoryl dihalide derivative having the formula (III), under anhydrous conditions, an alcohol having the formula R.sup.1 --OH to obtain a phosphoryl halide derivative having the formula (IV) ##STR28## which is then hydrolyzed, in the presence of a base, to provide the cyclic pyrophosphate derivative having the formula (I).
Claim 18
Dependent Claim 163 words
A process for the production of cyclic pyrophosphate derivatives having the formula (I) ##STR25## wherein A represents a direct bond between the two phenyl rings or a divalent moiety selected from the group consisting of lower alkylene, aryl substituted lower alkylene, cycloalkylidene, sulfonyl and oxy; R 1 represents allyl, acryloyloxy lower alkyl or methacryloyloxy lower alkyl, in which the lower alkyl can be substituted with halogen; and R 2 represents independently hydrogen, halogen, lower alkyl or lower alkoxy; the process comprising: reacting, under anhydrous conditions, a phenol derivative having the formula (II) ##STR26## with a phosphoryl halide to give the phosphoryl dihalide derivative having the formula (III) ##STR27## wherein X is halogen; adding to the phosphoryl dihalide derivative having the formula (III), under anhydrous conditions, an alcohol having the formula R.sup.1 --OH to obtain a phosphoryl halide derivative having the formula (IV) ##STR28## which is then hydrolyzed, in the presence of a base, to provide the cyclic pyrophosphate derivative having the formula (I).
Claim 19
Dependent Claim 15 words
The process according to claim 16, wherein the base, present during hydrolysis, is an amine.

References Cited (Backward Citations)

US3476699A Cited
GB2082184A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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