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(12) Patent Application Publication (10) Pub. No.: US 2007/0161543 A1 Yu Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2007/0161543 A1 Yu Et Al US 2007 O161543A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0161543 A1 Yu et al. (43) Pub. Date: Jul. 12, 2007 (54) N-(PHOSPHONOALKYL)-AMINO ACIDS, (52) U.S. Cl. .............................. 514/7: 514/114: 530/331; DERVATIVES THEREOF AND 558/170 COMPOSITIONS AND METHODS OF USE (76) Inventors: Ruey J. Yu, Chalfont, PA (US); Eugene J. Van Scott, Abington, PA (US) (57) ABSTRACT Correspondence Address: AKN GUMPSTRAUSS HAUER & FELD The present invention relates to an N-(phosphonoalkyl)- 6. COMMERCE SQUARE amino acid, a related compound or a derivative thereof, the 2005 MARKET STREET, SUITE 2200 N-(phosphonoalkyl)-amino acid, related compound or PHILADELPHIA, PA 19103 (US) derivative thereof being in a form as a free acid, salt, partial salt, lactone, amide or ester, or in Stereoisomeric or non (21) Appl. No.: 11/621,287 Stereoisomeric form, other than N-(phosphonomethyl)-gly (22) Filed: Jan. 9, 2007 cine or N.N-bis(phosphonomethyl)-glycine. Also included is a composition including an N-(phosphonoalkyl)-amino acid, Related U.S. Application Data a related compound or a derivative thereof in a form as a free (60) Provisional application No. 60/757,614, filed on Jan. acid, salt, partial salt, lactone, amide or ester, or in Stereoi 10, 2006. sy u. Is Someric or non-stereoisomeric form, and a cosmetically or pharmaceutically acceptable vehicle for topical or systemic Publication Classification administration to a mammalian Subject, as well as a method of administering an effective amount of Such a composition (51) Int. Cl. A6 IK 38/05 (2006.01) for alleviating or improving a condition, disorder, symptom A6 IK 3/66 (2006.01) or syndrome associated with at least one of a nervous, C07K 5/10 (2006.01) vascular, musculoskeletal or cutaneous system. US 2007/01 6 1543 A1 Jul. 12, 2007 N-(PHOSPHONOALKYL)-AMINO ACIDS, derivative thereof, the N-(phosphonoalkyl)-amino acid, DERVATIVES THEREOF AND COMPOSITIONS related compound or derivative thereof being in a form as a AND METHODS OF USE free acid, salt, partial salt, lactone, amide or ester, or in Stereoisomeric or non-stereoisomeric form, other than CROSS-REFERENCE TO RELATED N-(phosphonomethyl)-glycine or N.N-bis(phosphonom APPLICATIONS ethyl)-glycine. 0001) This application claims the benefit under 35 U.S.C. 0006 Another aspect of the present invention relates to S 119(e) of U.S. Provisional Application No. 60/757,614, an N-(phosphonoalkyl)-amino acid compound, a related filed Jan. 10, 2006, the entire disclosure of which is hereby compound or a compound derived therefrom, the compound incorporated herein by reference. includes the group consisting of N-(phosphonoalkyl)-pro line and a compound or derivative thereof having the BACKGROUND OF THE INVENTION following formula: 0002 The present invention relates to an N-(phospho noalkyl)-amino acid, a related compound or a derivative thereof, the N-(phosphonoalkyl)-amino acid, related com wherein R is H, an alkyl group having 1 to 19 carbon atoms, pound or derivative thereof being in a form as a free acid, an aryl group having 6 to 19 carbon atoms or an aralkyl salt, partial salt, lactone, amide or ester, or in Stereoisomeric group having 7 to 19 carbon atoms; and R can also carry or non-stereoisomeric form, other than N-(phosphonom OH, -SH, -SCH, -NH = NR,R, COR4, NH ethyl)-glycine or N,N-bis(phosphonomethyl)-glycine. The CONH, -NHC(=NR)NH, imidazole, pyrrolidine or present invention also relates to a composition including an other heterocyclic group; m is an integer from 0 to 5; R is N-(phosphonoalkyl)-amino acid, a related compound or a a phosphonoalkyl group having a formula derivative thereof in a form as a free acid, salt, partial salt, (HO)PO(CH), ; R is H or a phosphonoalkyl group lactone, amide or ester, or in Stereoisomeric or non-stereoi having a formula (HO)PO(CH), ; n is an integer from 1 Someric form, and a cosmetically or pharmaceutically to 9; R is —NH2 or —ORs. Rs is H, an alkyl group having acceptable vehicle for topical or systemic administration to 1 to 19 carbon atoms, an aryl group having 6 to 19 carbon a mammalian Subject, as well as a method of administering atoms or an aralkyl group having 7 to 19 carbon atoms; and an effective amount of Such a composition for alleviating or the H attached to any carbon atom can be substituted by I. improving a condition, disorder, symptom or syndrome F, Cl, Br, OH oran alkoxy group having 1 to 9 carbon atoms: associated with at least one of a nervous, vascular, muscu and wherein the N-(phosphonoalkyl)-amino acid, related loskeletal or cutaneous system. compound or derivative thereof is in a form as a free acid, salt, partial salt, lactone, amide or ester, or in a stereoiso 0003 N-(Phosphonomethyl)-glycine is listed as glypho meric or non-stereoisomeric form; provided that the com sate, CHNOP, molecular weight 169, in The Merck pound is not N-(phosphonomethyl)-glycine or N,N-bis(pho Index, 13" edition, 2001, page 803. The mono(isopropy sphonomethyl)-glycine. lamine) salt of N-(phosphonomethyl)-glycine is a primary active ingredient in Roundup(R) herbicide. N,N-Bis(pho 0007 Another aspect of the present invention relates to a sphonomethyl)-glycine is listed as glyphosine, composition comprising an N-(phosphonoalkyl)-amino CH, NO,P, molecular weight 263, in The Merck Index, acid, a related compound or a derivative thereof, the 13 edition, 2001, page 804. This compound is listed as plant N-(phosphonoalkyl)-amino acid, related compound or growth regulator known to cause chlorosis in green plants, derivative thereof being in a form as a free acid, salt, partial and also used as a chemical ripener. U.S. Pat. No. 3,288,846 salt, lactone, amide or ester, or in Stereoisomeric or non entitled “Processes for Preparing Organo-Phosphonic Stereoisomeric form, and a cosmetically or pharmaceutically Acids' describes a synthesis of N-substituted aminometh acceptable vehicle for topical or systemic administration to ylenephosphonic acid. U.S. Pat. No. 3,799,758 entitled a mammalian Subject. “N-Phosphonomethyl-Glycine Phytotoxicant Composi 0008. Yet another aspect of the present invention relates tions' describes N-(phosphonomethyl)-glycine and its to a method of alleviating or improving a condition, disor derivatives useful as phytotoxicants and herbicides. U.S. der, symptom or syndrome associated with at least one of a Pat. No. 3,853,530 entitled “Regulating Plants with nervous, vascular, musculoskeletal or cutaneous system, the N-phosphonomethyl-Glycine and Derivatives Thereof method comprising administering to a mammalian Subject describes the use of N-Phosphonomethyl-glycine and having the disorder, symptom or syndrome an amount derivatives useful for regulating the natural growth and effective for alleviating or improving the condition, disorder, development of plants. symptom or syndrome of a composition comprising an 0004 There has been no teaching, suggestion or impli N-(phosphonoalkyl)-amino acid, a related compound or a cation about the use of N-(phosphonomethyl)-glycine or its derivative thereof, the N-(phosphonoalkyl)-amino acid, derivatives for topical or systemic administration to mam related compound or derivative thereof being in a form as a mals, including humans. The present inventors have deter free acid, salt, partial salt, lactone, amide or ester, or in mined that such compounds are useful for treating various Stereoisomeric or non-stereoisomeric form, and a cosmeti medical and cosmetic conditions in animals, such as mam cally or pharmaceutically acceptable vehicle for topical or mals, and including humans. systemic administration to the mammalian Subject. 0009. The cosmetic conditions and medical disorders, BRIEF SUMMARY OF THE INVENTION symptoms or syndromes associated with at least one of a 0005 One aspect of the present invention relates to an nervous, vascular, musculoskeletal or cutaneous system, and N-(phosphonoalkyl)-amino acid, a related compound or a others, include, by way of example and not limitation, itch, US 2007/01 6 1543 A1 Jul. 12, 2007 pain, inflammation, erythema, eczema, dermatitis, derma N-(phosphonomethyl)-amino acids can be formed including toses, arthritis, acne, rosacea, dry skin, ichthyosis, keratoses, different stereoisomers such as D. L. and DL forms. psoriasis, pigmented skin, aging related skin changes. The 0017 Some amino acids are metabolites or are related to compositions may also be used for skin lightening. or derived from the common amino acids. Other amino acids 0010. As used herein, the singular forms an’, and have amino group(s) at other positions of the carbon chain, “the include plural referents unless the context clearly such as the B or Y position. Still other amino acids are found dictates otherwise. Thus, for example, reference to “a com in nature produced by microorganisms or plants. Certain pound” includes a plurality of Such compounds. amino acids, such as taurine, can have a Sulfonic acid group instead of a carboxyl group. Peptides are derived from DETAILED DESCRIPTION OF THE amino acids, and the peptides are called related amino acids INVENTION or amino acid derivatives. Other organic compounds which have at least one carboxyl group and at least one alkaline 0011. As noted above, the present invention relates to an group Such as amino, imino or guanidino group are also N-(phosphonoalkyl)-amino acid, a related compound or a called “related amino acids. As used herein, all these derivative thereof, the N-(phosphonoalkyl)-amino acid, compounds are called related amino acids. Representative, related compound or derivative thereof being in a form as a but non-limiting related amino acids include: B-alanine, free acid, salt, partial salt, lactone, amide or ester, or in y-aminobutanoic acid, B-aminoisobutanoic acid, anserine, Stereoisomeric or non-stereoisomeric form, other than aminolevulinic acid, camosine, canaline, canavanine, citrul N-(phosphonomethyl)-glycine or N.N-bis(phosphonom line, creatine, creatinine, cysteine Sulfinic acid, cystine, ethyl)-glycine.
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