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| OF THE INVENTION The novel alkali metal N-aminohydrocarbyl- and N-aminoheterohydrocarbyl-D-... |
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| Process for preparing poly (glucaramides) |
| OF THE INVENTION The novel alkali metal N-aminohydrocarbyl- and N-aminoheterohydrocarbyl-D-... |
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Derivatives of monosaccharides as cell adhesion inhibitors
| Details |
Inventors: Arora, Sudershan K; Gupta, Jang Bahadur; Joshi, Vishwas D;
Assignee: Ranbaxy Laboratories Limited (New Delhi, IN)
Primary Examiner: Wilson; James O.
Assistant Examiner: Khare; Devesh
Attorney, Agent or Firm: Deshmukh, Esq.; Jayadeep R., Heibel, Esq.; George E.
This invention relates generally to compounds and processes for synthesizing derivatives of 2-3-O-isopropylidene-α-L-xylo-2-hexulofuranosonic acid. The compounds of this invention are useful, inter-alia, for the inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies, including inflammatory and autoimmune diseases, such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection and psoriasis. This invention also relates to pharmacological compositions containing derivatives of 2-3-O-isopropylidene-α-L-xylo-2-hexulofuranosonic acid and the methods of treating such pathologies as listed above. |
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DETAILED DESCRIPTION OF THE INVENTION The compounds of the present invention may be prepared by techniques well-known in the art and familiar to the average synthetic organic chemist.
In addition, the compounds of the present invention may be prepared by the following novel and inventive reaction sequence, which also show preferred R, R1 and R2 groups.
##STR5## 2,3-O-Isopropyl-1-0-alkyl or arylalkyl-6-deoxy-6-aminosubstituted-L-xylo-2-hexulofuranose compounds of Formula II, as shown in Scheme I, are prepared according to the method described in U.
S.
Pat.
No.
5,637,570 and are the intermediates for the synthesis of the compounds of Formula I of the present invention.
Thus, the following intermediates were prepared following the process as described in U.
S.
Pat.
No.
5,637,570: 2,3-O-isopropylidene-6-deoxy-6-hexamethyleneimino-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-hexamethyleneimino-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-hexamethyleneimino-1-O-heptyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-pyrrolidinyl-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-pyrrolidinyl-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-pyrrolidinyl-1-O-heptyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-morphilinyl-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-morphilinyl-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-morphilinyl-1-O-heptyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-piperidinyl-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-piperidinyl-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-piperidinyl-1-O-heptyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylpyrrolidinyl-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylpyrrolidinyl-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylpyrrolidinyl-1-O-heptyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylmorpholinyl-1-O-dodecyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylmorpholinyl-1-O-decyl-α-L-xylo-2-hexulofuranose 2,3-O-isopropylidene-6-deoxy-6-ethylmorpholinyl-1-O-heptyl-α-L-xylo-2-hexulofuranose
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