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US4239709A
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Process for preparing optically active oxazaphosphorins
Assignee: Otsuka Pharmaceutical Co Ltd
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Filing: 1979-05-29
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Granted: 1980-12-16
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Expires: 1999-05-29
Abstract
Abstract Novel method optically active oxazaphosphorin derivatives represented by the general formula (I), ##STR1## wherein R 1 , R 2 and R 3 are respectively different from each other and are hydrogen atom(s), lower alkyl group(s), aralkyl group(s), or aryl group(s); and X is a halogen atom. The novel oxazaphosphorin derivative is prepared by reacting an optically active amino alcohol derivative represented by the general formula (II), ##STR2## wherein R 1 , R 2 and R 3 are the same as defined above, with a phosphorus compound represented by the general formula (III), POX.sub.3 wherein X is the same as defined above. The novel optically active oxazaphosphorin derivatives are useful as intermediates for preparing optically active cyclophosphamide derivatives which are useful therapeutical agents for curing against follicular lymphoadenopathy, lymphosarcomatosis, Hodgkin's disease, lymphosarcoma cell leukaemia, reticulum-cell sarcoma or the like.
Inventors
- 👤 Tadao Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 20:06
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6581; C07F9/6584; C07F9/65842; C07F9/65846; A; A61; A61P; A61P31/00; A61P31/04; C07F9/06; C07F9/22; C07F9/26
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
98 words
A process for preparing an optically active oxazaphosphorin derivative represented by the general formula, ##STR7## wherein R 1 , R 2 and R 3 are respectively different from each other, and are each hydrogen atom, a lower alkyl group, an aralkyl group, or an aryl group; and X is a halogen atom, which is prepared by reacting an optically active aminoalcohol represented by the general formula, ##STR8## wherein R 1 , R 2 and R 3 are the same as defined above with a phosphor compound represented by the general formula, POX.sub.3 wherein X is a halogen atom.
Claim 2
Dependent Claim
98 words
A process for preparing an optically active oxazaphosphorin derivative represented by the general formula, ##STR7## wherein R 1 , R 2 and R 3 are respectively different from each other, and are each hydrogen atom, a lower alkyl group, an aralkyl group, or an aryl group; and X is a halogen atom, which is prepared by reacting an optically active aminoalcohol represented by the general formula, ##STR8## wherein R 1 , R 2 and R 3 are the same as defined above with a phosphor compound represented by the general formula, POX.sub.3 wherein X is a halogen atom.
Claim 3
Dependent Claim
20 words
A process according to claim 1, wherein the reaction is carried out in the absence or presence of a solvent.
Claim 4
Dependent Claim
23 words
A process according to claim 2, wherein the solvent is a saturated hydrocarbon, a halogenated aliphatic hydrocarbon, an aromatic hydrocarbon or an ether.
Claim 5
Dependent Claim
16 words
A process according to claim 3, wherein the saturated hydrocarbon is n-heptane, n-hexane, isooctane or cyclohexane.
Claim 6
Dependent Claim
17 words
A process according to claim 3, wherein the halogenated aliphatic hydrocarbon is methylene chloride, chloroform or 1,2-dichloroethane.
Claim 7
Dependent Claim
15 words
A process according to claim 3, wherein the aromatic hydrocarbon is benzene, toluene or xylene.
Claim 8
Dependent Claim
19 words
A process according to claim 3, wherein the ether is dimethylether, diethlether, isopropylether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, diglyme or triglyme.
Claim 9
Dependent Claim
19 words
A process according to claim 1, wherein the reaction is carried out in the presence of a basic compound.
Claim 10
Dependent Claim
14 words
A process according to claim 8, wherein the basic compound is a tertiary amine.
Claim 11
Dependent Claim
17 words
A process according to claim 9, wherein the tertiary amine is triethylamine, triisopropylamine, N,N-dimethylaniline, pyridine or quinoline.
Claim 12
Dependent Claim
15 words
A process according to claim 8, wherein the basic compound is an inorganic basic compound.
Claim 13
Dependent Claim
19 words
A process according to claim 11, wherein the inorganic basic compound is anhydrous potassium carbonate or anhydrous sodium carbonate.
Claim 14
Dependent Claim
23 words
A process according to claim 1, wherein the reaction is carried out at a temperature within the range from -70° to 100° C.
Claim 15
Dependent Claim
19 words
A process according to claim 13, wherein the reaction temperature is the range of from -70° to 50° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-16 | 1984-06-16 | 1984-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-16 | 1988-06-16 | 1988-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-16 | 1992-06-16 | 1992-12-16 | $7700.00 | Window Closed / Lapsed |