WO2007132234A1 - Compositions pharmaceutiques contenant de l'acide 5-aminolévulinique - Google Patents
Compositions pharmaceutiques contenant de l'acide 5-aminolévulinique Download PDFInfo
- Publication number
- WO2007132234A1 WO2007132234A1 PCT/GB2007/001791 GB2007001791W WO2007132234A1 WO 2007132234 A1 WO2007132234 A1 WO 2007132234A1 GB 2007001791 W GB2007001791 W GB 2007001791W WO 2007132234 A1 WO2007132234 A1 WO 2007132234A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ala ester
- product
- ala
- photosensitising
- agent
- Prior art date
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- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229960002749 aminolevulinic acid Drugs 0.000 title description 24
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 239000003814 drug Substances 0.000 claims abstract description 79
- 230000002165 photosensitisation Effects 0.000 claims abstract description 60
- -1 mitromycin Chemical compound 0.000 claims abstract description 54
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 53
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 30
- 229940127557 pharmaceutical product Drugs 0.000 claims abstract description 30
- 239000002243 precursor Substances 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims description 134
- 238000011282 treatment Methods 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 206010028980 Neoplasm Diseases 0.000 claims description 27
- 208000015181 infectious disease Diseases 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
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- 239000000203 mixture Substances 0.000 claims description 20
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- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
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- 230000003612 virological effect Effects 0.000 claims description 5
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
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- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 13
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- 229940124530 sulfonamide Drugs 0.000 description 1
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- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
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- 229960000565 tazarotene Drugs 0.000 description 1
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- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960001608 teicoplanin Drugs 0.000 description 1
- 229960001114 temocillin Drugs 0.000 description 1
- BVCKFLJARNKCSS-DWPRYXJFSA-N temocillin Chemical compound N([C@]1(OC)C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C=1C=CSC=1 BVCKFLJARNKCSS-DWPRYXJFSA-N 0.000 description 1
- 229960004556 tenofovir Drugs 0.000 description 1
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WSWJIZXMAUYHOE-UHFFFAOYSA-N tetroxoprim Chemical compound C1=C(OC)C(OCCOC)=C(OC)C=C1CC1=CN=C(N)N=C1N WSWJIZXMAUYHOE-UHFFFAOYSA-N 0.000 description 1
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- 229960004659 ticarcillin Drugs 0.000 description 1
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- 229960005053 tinidazole Drugs 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960005041 troleandomycin Drugs 0.000 description 1
- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
- 229960000497 trovafloxacin Drugs 0.000 description 1
- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
- UULSDCUWMKTMND-UHFFFAOYSA-N tryparsamide Chemical compound NC(=O)CNC1=CC=C([As](O)(O)=O)C=C1 UULSDCUWMKTMND-UHFFFAOYSA-N 0.000 description 1
- 229950000574 tryparsamide Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000003741 urothelium Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940093257 valacyclovir Drugs 0.000 description 1
- 229960002149 valganciclovir Drugs 0.000 description 1
- 208000010531 varicella zoster infection Diseases 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Definitions
- This invention relates to pharmaceutical products comprising 5- aminolevulinic acid (5-ALA) or a precursor or derivative thereof (e.g. a 5- ALA ester) in combination with a non-photosensitising therapeutic agent arid their use in treating conditions caused by or associated with drug-resistant micro-organisms or cells.
- the invention concerns the use of such products in the treatment or prevention of infectious diseases and/or cancer.
- Multi-drug resistance is an increasing problem in the field of infectious diseases.
- the use of antimicrobial agents to counter, for example, bacterial infections is becoming increasingly ineffective.
- Staphylococcus aureus S.
- S. aureus which is responsible for causing skin infections, as well as infecting wounds and burns.
- Toxic strains of S. aureus can enter the bloodstream as a result of such infections and this in turn may lead to serious complications and even life-threatening conditions such as toxaemia (toxic shock syndrome), endocarditis and pneumonia.
- Resistant strains of S. aureus include methicillin-resistant S. aureus (MRSA) which is now becoming a major cause of hospital-acquired infection and which causes significant infection and morbidity of hundreds of patients each year.
- MRSA methicillin-resistant S. aureus
- MRSA has now developed resistance to a wide variety of antimicrobials including erythromycin, tetracyclines, sulphonamides and chloramphenicol. MRSA is therefore now a serious threat to health.
- Certain MRSA strains of S. aureus also exist which are only susceptible to treatment by a single group of antibiotics, namely the glycopeptides such as vancomycin. These strains are known as vancomycin- resistant Staphylococcus aureus or VRSA.
- vancomycin- resistant Staphylococcus aureus or VRSA.
- resistant micro-organisms include P. acnes, group A' Streptococci, Enterococci, Acinetobacter haumannii (causes pneumonia), Candida (especially C. lusitaniae) and Cryptococcus.
- MDRs multi-drug resistant pumps
- PDT photodynamic therapy
- the invention provides a pharmaceutical product comprising a phot ⁇ sensitiser which is 5-ALA or a precursor or derivative thereof and a non-photosensitising therapeutic agent.
- the invention provides a kit containing a photosensitiser as hereinbefore defined and, separately, a non-photosensitising therapeutic agent as hereinbefore defined.
- the invention provides a pharmaceutical product or kit as hereinbefore defined for use as a medicament.
- pharmaceutical product as used herein is intended to encompass any combination of actives which comprises: (i) a photosensitiser which is 5-ALA or a precursor or derivative thereof; and (ii) a non-photosensitising therapeutic agent. More specifically, it includes combinations wherein said photosensitiser and said non-photosensitising therapeutic agent are provided separately (e.g. in separate containers, packages, tubes, vials, etc.), as a combined preparation (e.g. as a layered tablet) or as an intimate mixture (e.g. as a single composition).
- the photosensitiser which is 5-ALA or a precursor or derivative thereof and a non-photosensitising therapeutic agent are provided separately.
- precursors refers to precursors for 5-ALA which are converted metabolically to it and are thus essentially equivalent thereto.
- precursor covers biological precursors for protoporphyrin in the metabolic pathway for haem biosynthesis.
- derivatives include pharmaceutically acceptable salts and chemically modified agents, for example esters such as ALA esters.
- esters such as ALA esters.
- 5-ALA and derivatives thereof e.g. ALA esters
- 5-ALA and all such derivatives of 5-ALA, as well as their pharmaceutically acceptable salts, are suitable for use in the products and methods herein described.
- the 5-ALA derivatives useful in accordance with the invention may be any derivative of 5-ALA capable of forming protoporphyrin IX (PpIX) or any other photosensitiser (e.g. a PpIX derivative) in vivo.
- such derivatives will be a precursor of PpIX or of a PpIX derivative (e.g. a PpIX ester) in the biosynthetic pathway for haem and which are therefore capable of inducing an accumulation of PpIX at the site to be treated following administration in vivo.
- Suitable precursors of PpEK or PpIX derivatives include 5-ALA prodrugs which might be able to form 5-ALA in vivo as an intermediate in the biosynthesis of PpIX or which may be converted (e.g. enzymatically) to porphyrins without forming 5-ALA as an intermediate.
- 5-ALA esters are among the preferred compounds for use in the products and methods herein described.
- 5-ALA and esters of 5-ALA, and N-substituted derivatives thereof are preferred photosensitisers for use in the invention.
- Those compounds in which the 5-amino group is unsubstituted i.e. 5-ALA and 5-ALA esters
- 5-ALA esters are especially preferred.
- Esters of 5-aminolevuline acid with substituted or unsubstituted, preferably substituted, alkanols, i.e. alkyl esters or, more preferably, substituted alkyl esters are especially preferred photosensitisers for use in the invention. Examples of such compounds include those of general formula I:
- R 1 represents a substituted or unsubstituted, preferably substituted, straight-chained, branched or cyclic alkyl group (e.g. a substituted straight-chained alkyl group); and each R 2 independently represents a hydrogen atom or an optionally substituted alkyl group, e.g. a group R 1 ) and pharmaceutically acceptable salts thereof.
- alkyl unless stated otherwise, includes any long or short chain, cyclic, straight-chained or branched aliphatic saturated or unsaturated hydrocarbon group.
- the unsaturated alkyl groups may be mono- or polyunsaturated and include both alkenyl and alkynyl groups.
- such groups may contain up to 40 atoms.
- alkyl groups containing up to 30, preferably up to 10, particularly preferably up to 8, especially preferably up to 6, e.g. up to 4 carbon atoms are preferred.
- the substituted alkyl R 1 and R 2 groups may be mono or poly-substituted.
- Suitable substitue ⁇ ts may be selected from hydroxy, alkoxy, acy ⁇ oxy, alkoxycarbonyloxy, amino, aryl, nitro, oxo, fluoro, -SR 3 , -NR 3 2 and -PR 3 2 groups, and each alkyl group may be optionally interrupted by one or more -O-, -NR 3 -, -S- or -PR 3 - groups, in which R 3 is a hydrogen atom or a C 1-6 alkyl group).
- Preferred substituted alkyl R 1 groups include those carrying one or more oxo groups, preferably straight-chained C 4-I2 alkyl (e.g.
- C 8-10 alkyl groups substituted by one, two or three (preferably two or three) oxo groups.
- examples of such groups include 3,6-dioxa-l-octyl and 3,6,9-trioxa-l-decyl groups.
- Particularly preferred for use in the invention are those compounds of formula I in which at least one R 2 represents a hydrogen atom.
- each R 2 represents a hydrogen atom.
- R 1 represents an unsubstituted alkyl group (preferably Ci - 8 alkyl, e.g. Ci -6 alkyl) or more preferably an alkyl group (e.g. Cj -2 alkyl, especially Ci alkyl) substituted by a substituent as hereinbefore defined (e.g. by an aryl group such as phenyl or by an alkoxy group such as methoxy) are also preferred.
- an unsubstituted alkyl group preferably Ci - 8 alkyl, e.g. Ci -6 alkyl
- an alkyl group e.g. Cj -2 alkyl, especially Ci alkyl
- a substituent as hereinbefore defined e.g. by an aryl group such as phenyl or by an alkoxy group such as methoxy
- Unsubstituted alkyl groups which may be used in the invention include both branched and straight-chained hydrocarbon groups.
- Compounds of formula I in which R 1 is a C 4-8 , preferably a C 5-8 , straight chain alkyl group which is branched by one or more C 1-6 (e.g. Ci -2 alkyl) groups are preferred.
- Representative examples of suitable unsubstituted branched alkyl groups include 2-methylpentyl, 4- methylpentyl, 1-ethylbutyl and 3, 3 -dimethyl- 1 -butyl. 4-methylpentyl is particularly preferred.
- R 1 is a Ci -I0 straight-chained alkyl group
- suitable unsubstituted alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl and octyl (e.g. n-propyl, n-butyl, n-pentyl, n-hexyl and n-octyl).
- Hexyl, especially n-hexyl is a particularly preferred group.
- Methyl is also particularly preferred.
- R 1 represents a Ci_ 2 alkyl group (preferably a Ci alkyl group) optionally substituted by an aryl group.
- R 1 represents an alkyl group (e.g. C 1-2 alkyl, especially Ci alkyl) substituted by an aryl group (e.g. phenyl).
- Preferred substituted alkyl R 1 groups which may be present in compounds of formula I include Cj -6 alkyl, preferably Ci -4 alkyl, particularly preferably Ci or C 2 alkyl (e.g. Ci alkyl) substituted (preferably terminally substituted) by an optionally substituted aryl group.
- aryl group is meant a group which is aromatic.
- Preferred aryl groups comprise up to 20 carbon atoms, more preferably up to 12 carbon atoms, for example, 10 or 6 carbon atoms.
- Aryl groups which may be present in the compounds of the invention may be heteroaromatic (e.g. 5-7 membered heteroaromatics) but are preferably non- heteroaromatic.
- non-heteroaromatic is meant an aryl group having an aromatic system comprising electrons originating solely from carbon atoms.
- Preferred aryl groups include phenyl and napthyl, especially phenyl. In preferred compounds for use in the invention one or two aryl groups may be present, preferably one.
- Aryl groups which may be present in the compounds of the invention may optionally be substituted by one or more (e.g. 1 to 5), more preferably one or two, groups (e.g. one group).
- the aryl group is substituted at the meta or para position, most preferably the para position.
- Suitable substituent groups may include haloalkyl (e.g. trifluoromethyl), alkoxy (i.e. -OR groups wherein R is preferably a Ci -6 alkyl group), halo (e.g. iodo, bromo, more especially chloro and fluoro), nitro and Ci -6 alkyl (preferably Ci -4 alkyl).
- Preferred Ci -6 alkyl groups include methyl, isopropyl and t-butyl, particularly methyl. Particularly preferred substituent groups include chloro and nitro. Still more preferably the aryl group is unsubstituted.
- Preferred compounds for use in the invention include methyl ALA ester, ethyl ALA ester, propyl ALA ester, butyl ALA ester, pentyl ALA ester, hexyl ALA ester, octyl ALA ester, 2-methoxyethyl ALA ester, 2-methylpentyl ALA ester, 4- methylpentyl ALA ester, 1-ethylbutyl ALA ester, 3, 3 -dimethyl- 1 -butyl ALA ester, benzyl ALA ester, 4-isopropylbenzyl ALA ester, 4-methylbenzyl ALA ester, 2- methylbenzyl ALA ester, 3-methylbenzyl ALA este
- ALA ester ethyl ALA ester, 2-methoxyethyl ALA ester, benzyl ALA ester, A- isopropylbenzyl ALA ester, 4-methylbenzyl ALA ester, 2-methylbenzyl ALA ester, 3-methylbenzyl ALA ester, 4-[t-butyl]benzyl ALA ester, 4-[trifluoromethyl]benzyl ALA ester, 4-methoxybenzyl ALA ester, 3,4-[di-chloro]benzyl ALA ester, A- chlorobenzyl ALA ester, 4-fluorobenzyl ALA ester, 2-fluorobenzyl ALA ester, 3- fluorobenzyl ALA ester, 2,3,4,5,6-pentafluorobenzyl ALA ester, 3-nitrobenzyl ALA ester, 4-nitrobenzyl ALA ester, 2-phenylethyl ALA ester, 4-phenylbutyl ALA este
- ALA ester 4-isopropylbenzyl ALA ester, 4-methylbenzyl ALA ester, 2- methylbenzyl ALA ester, 3-methylbenzyl ALA ester, 4-[t-butyl]benzyl ALA ester, 4-[trifluoromethyl]benzyl ALA ester, 4-methoxybenzyl ALA ester, 3,4-[di- chlorojbenzyl ALA ester, 4-chlorobenzyl ALA ester, 4-fluorobenzyl ALA ester, 2- fluorobenzyl ALA ester, 3-fluorobenzyl ALA ester, 2,3,4,5,6-pentafluorobenzyl
- ALA ester 3-nitrobenzyl ALA ester, 4-nitrobenzyl ALA ester, 2-phenylethyl ALA ester, 4-phenylbutyl ALA ester, 3-pyridinyl-methyl ALA ester, 4-diphenyl-methyl ALA ester and benzyl-5-[(l-acetyloxyethoxy)-carbonyl]amino levulinate.
- Especially preferred compounds for use in the products and methods herein described include benzyl ALA ester, 4-isopropylbenzyl ALA ester and A- methylbenzyl ALA ester, especially benzyl ALA ester. 4-Nitrobenzyl ALA ester, A- chlorobenzyl ALA ester and benzyl ALA ester are especially preferred.
- the compounds for use in the invention may be prepared by any conventional procedure available in the art (e.g. as described in WO02/10120 to PhotoCure ASA).
- esters of 5-ALA may be prepared by reaction of 5- ALA with the appropriate alcohol in the presence of base.
- compounds for use in the invention may be available commercially (e.g. from PhotoCure ASA, Norway).
- the compounds for use in the invention may be in the form of a free amine (e.g. -NH 2 , -NHR 2 or -NR 2 R 2 ) or preferably in the form of a physiologically acceptable salt.
- Such salts preferably are acid addition salts with physiologically acceptable organic or inorganic acids. Suitable acids include, for example, hydrochloric, nitric, hydrobromic, phosphoric, sulphuric, sulphonic and sulphonic acid derivatives.
- Particularly preferred salts are acid addition salts with sulphonic acid or sulphonic acid derivatives as described in WO2005/092838 to PhotoCure ASA, the entire contents of which are incorporated herein by reference. Procedures for salt formation are conventional in the art.
- the photosensitiser is provided in combination with at least one (e.g. one or two, preferably one) non-photosensitising therapeutic agent.
- a non-photosensitising therapeutic agent is meant any therapeutic agent which, on irradiation with light, is unable to undergo a conversion to cytotoxic form.
- the non- photosensitising therapeutic agent is a conventional therapeutic agent (i.e. an agent already commercially available for therapeutic and/or preventative treatment).
- the non- ⁇ hotosensitising therapeutic agent maybe an agent in respect of which certain cells (especially micro-organism cells or cancer cells) have acquired a degree of tolerance or resistance.
- drugs are associated with resistance problems.
- P. acnes Erythromycin, clinidamycin, doxicycline, minocycline and tetracycline
- S. aureus Methicillin, penicillins, erythromycin, tetracycline, fusidic acid and quinolones
- Enterococci Vancomycin (some strains often resistant to all antibiotics); Acinetobacter baumannii (causes pneumonia) - some strains can resist all antibiotics;
- Candida e.g. C. lusitaniae
- amphotericin e.g. C. lusitaniae
- non- photosensitising therapeutic agent is either an anti-infective agent or an anti-cancer agent.
- Preferred anti-infective agents include anti-bacterial, anti-fungal, anti-viral and anti-protozoal agents, especially anti-bacterial agents.
- Preferred anti-bacterial agents present in the pharmaceutical products of the invention are aminoglycosides, antimycobacterials, cephalosporins and beta- lactams, amphenicols, polypeptides, lincosamides, macrolides, penicillins, quinolones, sulphonamides and diaminopyrimidines, tetracyclines, oxazolidinones and nitrofurans.
- Other anti-bacterial agents that may be present include fusidinic acid, azelaic acid and metronidazole.
- Suitable aminoglycosides for use in the invention include framycetin, kanamycin, neomycin, paromomycin, streptomycin, andramycin, tobramycin, gentamicin and sissomicin.
- antimycobacterials which maybe present in the products of the invention include rifampicin, rifamycin sodium, rifaximin, rifamide, rifatnin and rifabutin.
- cephalosporins and beta-lactams present in the products of the invention are cephalothin, cephazolin,.cephradine, cefroxadine, cefadroxil, cefatrizine, cephalexin, pivcephalexin, cefaclor, cefazolin, cefprozil, cephamandole, cefuroxime, cefuroxime, cefonicid, ceforanide, cefotiam, cefotaxime, cefmenoxime, cefodizime, ceftizoxime, ceftriaxone, cefixime, cefoxitin, cefdinir, cefetamet pivoxil, cefpodoxime proxetil, ceftibuten, latamoxef, ceftazidime, cefoperazone, cefpiramide, cefsulodin, cefepime, cefpirome, cefoxitin, cefmetazole, cefo
- Preferred amphenicols present in the products of the invention are chloramphenicols (e.g. chloramphenicol), thiamphenicol and azidamfenicol.
- Preferred polypeptides present in the products of the invention are glycopeptides (e.g. vancomycin, teicoplanin and ramoplanin).
- Preferred lincosamides present in the products of the invention are lincomycin and clindamycin.
- Preferred macrolides present in the products of the invention are erythromycin, spiramycin, oleandomycin, triacetyloleandomycin, josamycin, kitasamycin, midecamycin, rokitamycin, azithromycin, clarithromycin, dirithromycin, roxithromycin, flurithromycin, pristinamycin and virginiamycin.
- Preferred penicillans present in the products of the invention are benzylpenicillan, phenoxymethylpenicillan, phenethicillan, propicillan, methicillan, cloxacillan, dicloxacillan, flucloxacillin, oxacillin, nafcillin, ampicillin, amoxycillan, bacampicillin, hetacillin, metampicillin, pivampicillin, carbenicillin, carfecillin, carindacillin, sulbenicillin, ticarcillin, azlocillin, mezlocillin, piperacillin, temocillin, mecillinam and pivmecillinam.
- Preferred quinolones present in the products of the invention are nalidixic acid, oxolinic acid, cinoxacin, acrosoxacin, pipemidic acid, flumequine, ciprofloxacin, enoxacin, fleroxacin, grepafloxacin, levofloxacin, lomefloxacin, nadifloxacin, norfloxacin, ofloxacin, pefloxacin, rufloxacin, sparfloxacin, trovafloxacin, danofloxacin, enrofloxacin, marbofloxacin and difloxacin.
- Preferred sulphonamides and diaminopyrimidines present in the products of the invention are sulphanilamide, sulphapyridine, sulphadiazine, sulphadimidine, sulphafurazole, sulphamethoxazole, sulphadimethoxine, sulphamethoxydiazine, sulphamethoxypyridazine, sulfadoxine, sulfametopyrazine, sulphaguanidine, succinylsulphathiazole, phthalylsulphathiazole, silver sulphadiazine, mafenide acetate, sulphasalazine, trimethoprim, baquiloprim, brodimoprim, ormetoprim, tetroxoprim and co-trimoxazole.
- Preferred tetracyclines present in the products of the present invention are chlortetracycline, oxyte
- a preferred oxazolidinone present in the products of the invention is linezolid.
- Examples of preferred anti-bacterial agents include chloramphenicol, tetracyclines (e.g. oxytetracycline), penicillin derivatives (e.g. phenoxymethylpenicillin, ampicillin, methicillin), cephalosporin derivatives (e.g. cephalexin), fusidinic acid, vancomycin, erythromycin, azelaic acid and metronidazole.
- tetracyclines e.g. oxytetracycline
- penicillin derivatives e.g. phenoxymethylpenicillin, ampicillin, methicillin
- cephalosporin derivatives e.g. cephalexin
- fusidinic acid vancomycin
- erythromycin erythromycin
- azelaic acid metronidazole.
- Preferred anti-fungal agents present in the pharmaceutical products of the invention are polyene antifungals (e.g. amphotericin, nystatin), imidazole antifungals (ketoconazole, miconazole, flutrimazole, econazole, clotrimazole, fenticonazole), thiocarbamate antifungals and triazole antifungals (e.g. fluconazole, itraconazole, voriconazole).
- Other antifungals that may be present include caspofungin, flucytosine, griseofulvin and terbinafine.
- Examples of preferred anti-fungals include griseofulvin, nystatin and amphotericin B.
- Preferred anti- viral agents present in the pharmaceutical products of the invention are monoclonal antibodies, peptidomimetics (e.g. indinavir, lopinavir, nelfmavir, ritonavir, saquinavir), polynucleotides (e.g. amligen), purines and pyrimidones (e.g. acyclovir, adafovir, cidofovir, didanosine, famciclovir, floxuridine, ganciclovir, idoxuridine, lamivudine, stavudine, tenofovir, valacyclovir, valganciclovir, zidovudine).
- Other anti-viral agents that may be present include interferons, podophyllotoxin and ribavirin.
- Examples of preferred anti-virals include acyclovir, zidovudine and indinavir.
- Preferred anti-protozoal agents present in the pharmaceutical products of the invention are trivalent arsenicals (e.g. melarsoprol), pentavalent arsenicals (e.g. acetarsol, tryparsamide), aromatic diamidines (e.g. pentamidine), antimony compounds (e.g. meglumine antimonate, sodium stibogluconate), dichloroacetamides (e.g. diloxanide), halogenated hydroxyquinolines (e.g. di- iodohydroxyquinoline) and nitrofurans (e.g. furazolidone, nifuratel, nifurtimox), 5- nitroimidazoles (e.g.
- anti-protozoal agents that may be present include atovaquone, benznidazole, dehydroemetine, eflornithine, mepacrine, suramin and puramycin.
- Preferred anti-cancer agents present in the pharmaceutical products of the invention are antineoplastic agents.
- Representative examples of ariti-neoplastic agents include alkaloids (e.g. incristine, vinblastine, vinorelbine, topotecan, teniposiode, paclitaxel, etoposide and docetaxel), alkylating agents (e.g.
- alkyl sulfonates such as busulfan
- aziridines e.g. carboquone, ethylenimines and methylmelamines
- nitrogen mustards e.g. chlorambucil, cyclophosphamide, estramustin, ifosfamide and melphalan
- nitrosurea derivatives e.g. carmustine and lomustine
- antibiotics e.g. mitomycins, doxorubicin, daunorubicin, epirubicin and bleomycins
- antimetabolites e.g. folic acid analogues and antagonists such as methotrexate and raltitrexed
- purine analogues e.g.
- 6-mercaptopurine 6-mercaptopurine
- pyrimidine analogues e.g. tegafur, gemcitabine, fluorouracil and cytarabine
- cytokines enzymes (e.g. L-asparginase, ranpirnase)
- immunomodulators e.g. interferons, immunotoxins, monoclonal antibodies
- taxanes topoisomerase inhibitors
- platinum complexes e.g. carboplatin, oxaliplatin and cisplatin
- hormonal agents e.g. androgens, estrogens, antiestrogens
- aromatase inhibitors e.g. androgens, estrogens, antiestrogens
- Other anti-neoplastic agents for use in the invention include imiquimod, irenotecan, leucovorin, levamisole, etopisde and hydroxyurea.
- Preferred anti-cancer agents for use in the invention include 5-fluorouracil, imiquimod, cytokines, mitomycin C, epirubicin, irenotecan, oxalipatin, leucovorin, levamisole, doxorubicin, cisplatin, etoposide, doxirubicin, methotrexate, taxanes, topoisomerase inhibitors, hydoroxyurea and vinorelbine.
- antibiotics such as mitomycin and pyrimidine analogues such as 5-fiuorouracil.
- the non-photosensitising therapeutic agent e.g. anti-bacterial agent
- the pharmaceutical products herein described is other than an acne treatment agent (as used herein, "acne” includes both inflammatory and noninflammatory diseases of the pilobaceous unit).
- an acne treatment agent as used herein, "acne” includes both inflammatory and noninflammatory diseases of the pilobaceous unit.
- the non- photosensitising therapeutic agent e.g.
- anti-bacterial agent is not a: retinoid such as acitretin, isotretinion, tretinion or tazarotene, a peroxide such as benzoyl peroxide, an antibiotic such as tetracycline, clindamycin, erythromycin, doxycycline, oxytetracycline, minocycline, trimethoprim and metronidazole, a hormone such as co-cyprindiol (cyproterone acetate with ethinyllestradiol), an azelaic acid or derivative thereof (e.g. as described in WO03/045893 to PhotoCure ASA), adapalene, nicotinamide or salicyclic acid.
- retinoid such as acitretin, isotretinion, tretinion or tazarotene
- a peroxide such as benzoyl peroxide
- an antibiotic such as
- the non-photosensitising therapeutic agent e.g. anti-cancer agent
- the pharmaceutical product is not an angiogenic drug (e.g. TNP-470, angiostatin or an integrin ⁇ v ⁇ 3 antagonist) or an immunotherapy agent (e.g. antibody or effector such as macrophage activating factor).
- an angiogenic drug e.g. TNP-470, angiostatin or an integrin ⁇ v ⁇ 3 antagonist
- an immunotherapy agent e.g. antibody or effector such as macrophage activating factor
- non-photosensitising therapeutic agents for use in the invention may be prepared by any conventional procedure available in the prior art. Alternatively, in most cases, these will be commercially available.
- the photosensitiser and non-photosensitising therapeutic agent may each be formulated in any conventional manner with one or more physiologically acceptable carriers or excipients according to techniques well known in the art.
- the photosensitiser and the therapeutic agent may be provided separately, in a combined preparation or in a single composition (e.g. as in intimate mixture, dispersion or suspension).
- the photosensitiser and the therapeutic agent need not be formulated in an identical manner.
- one component e.g. the photosensitiser
- the remaining component e.g. the non-photosensitising therapeutic agent
- formulating the individual components of the product in an identical fashion e.g. both components maybe provided as creams or as aqueous solutions) will be most convenient.
- the individual components will typically be provided in a single dosage form, e.g. in a tablet or capsule, in which the individual components are separated from one another, for example by way of distinct layers in a tablet or in separate compartments of a capsule.
- Combined preparations may also be provided in the form of tablets having a central core comprising one active component and an outer coating in which the second active is present.
- the pharmaceutical product according to the invention comprises a photosensitiser as herein before defined, a non-photosensitising therapeutic agent and preferably one or more physiologically acceptable carriers or excipients. Such compositions form a further aspect of the invention.
- any given formulation comprises the photosensitiser, the therapeutic agent or both, it may additionally comprise one or more physiologically acceptable carriers or excipients.
- Other agents such as lubricating agents, wetting agents, emulsifying agents, suspending agents, preserving agents, flavouring agents, odour enhancers and/or adsorption enhancers e.g. surface penetration enhancers mentioned below, and the like may also be present.
- Solubilising and/or stabilising agents may also be used, e.g. cyclodextrins (CD) ⁇ , ⁇ , ⁇ and HP-cyclodextrin.
- Penetration enhancers may have a beneficial effect in enhancing the photosensitising effect of the photosensitiser present in the products and kits of the invention.
- Surface penetration assisting agents especially dialkylsulphoxides such as dimethylsulphoxide (DMSO) may therefore be included in the formulations of the invention (e.g. in the photosensitiser-containing component).
- the surface penetration assisting agent may be any of the skin penetration assisting agents described in the pharmaceutical literature, e.g. chelators (e.g. EDTA), surfactants (e.g. sodium dodecyl sulfate), non-surfactants, bile salts (sodium deoxycholate) and fatty acids (e.g. oleic acid).
- Examples of appropriate surface penetration assisting agents include isopropanol, HPE-101 (available from Hisamitsu), DMSO and other dialkylsulphoxides, in particular n-decylmethyl sulphoxide (NDMS), dimethylsulphacetamide, dimethylfornamide (DMFA), dimethylacetamide, glycols, various pyrrolidone derivatives (Woodford et al., J. Toxicol. Cut. & Ocular Toxicology, 1986, 5: 167-177) and Azone® (Stoughton et al, DrugDpv. Ind. Pharm. 1983 , 9: 725-744) or mixtures thereof.
- the surface penetration agent may conveniently be provided in a concentration range of 0.2 to 50 % by weight of the total weight of the formulation in which it is present, e.g. about 10 % by weight of the. total weight of the formulation in which it is present.
- Chelating agents may also have a beneficial effect in enhancing the photosensitising effect of the photosensitiser present in the products and kits of the invention.
- Chelating agents may, for example, be included in order to enhance the accumulation of Pp since the chelation of iron by the chelating agent prevents its incorporation into Pp to form haem by the action of the enzyme ferrochelatase, thereby leading to a build up of Pp. The photosensitising effect is therefore enhanced.
- Suitable chelating agents that may be included in the formulations of the invention (e.g. in the photosensitiser-containing formulation) include aminopolycarboxylic acids, such as any of the chelants described in the literature for metal detoxification or for the chelation of paramagnetic metal ions in magnetic resonance imaging contrast agents. Particular mention may be made of EDTA, CDTA (cyelohexane triamine tetraacetic acid), DTPA and DOTA and well known derivatives and analogues thereof. EDTA and DTPA are particularly preferred. To achieve the iron-chelating effect, desferoxamine and other siderophores may also be used, e.g. in conjunction with aminopolycarboxylic acid chelating agents such as EDTA.
- aminopolycarboxylic acids such as any of the chelants described in the literature for metal detoxification or for the chelation of paramagnetic metal ions in magnetic resonance imaging contrast agents. Particular mention may be made of EDTA, CDTA (cy
- the chelating agent may conveniently be used at a concentration of 0.05 to 20%, e.g. 0.1 to 10% by weight based on the formulation in which it is present.
- the desired concentration of photosensitiser and the non-photosensitising therapeutic agent in the pharmaceutical products and kits of the invention will vary depending on several factors including the chemical nature of the compound, the nature and chemical composition of the formulation in which this is presented, the intended mode of administration, the nature of the disease to be treated and the subject to be treated. Generally, however, the concentration of photosensitiser is conveniently in the range 1 to 40%, e.g. 2 to 25, preferably 5 to 20% by weight. The concentration of the non-photosensitising therapeutic agent is conveniently in the range 0.1 to 50%, e.g. 0.5 to 30%, preferably 1 to 20% by weight. Concentrations are by weight of the formulation in which the photosensitiser and/or therapeutic agent are present.
- the formulations of the products and kits of the invention may be administered systemically (e.g. orally or parenterally) or, more preferably, locally (e.g. by injection or, most preferably, topically) at or near an affected site, for example a site of infection or tumor growth.
- the route of administration will depend on the severity and nature of the disease to be treated, the location of the disease and the nature of the photosensifiser and the non-photosensitising agent to be administered.
- the photosensitiser and non-photosensitising therapeutic agent may be administered by the same route, or more preferably, by different routes. Generally, however, local administration, still more preferably topical application, will be preferred for the photosensitiser.
- the non-photosensitiser is preferably administered systemically, e.g. orally.
- Preferred formulations may take any form suitable for the route of administration. These include gels, creams, ointments, sprays, lotions, salves, sticks, soaps, powders, aerosols, drops, solutions, tablets, powders, capsules and any other conventional pharmaceutical forms in the art. Gels, creams and ointments are generally preferred for the formulation comprising photosensitiser. Tablets and capsules are preferred for the formulation comprising the non-photosensitising therapeutic agent.
- Ointments, gels and creams may, for example, be formulated with an aqueous or oily base with the addition of suitable thickening and/or gelling agents.
- Lotions may be formulated with an aqueous or oily base and will, in general, also contain one or more emulsifying, dispersing, suspending, thickening or colouring agents.
- Powders may be formed with the aid of any suitable powder base.
- Drops and solutions may be formulated with an aqueous or non-aqueous base also comprising one or more dispersing, solubilising or suspending agents. Aerosol sprays are conveniently delivered from pressurised packs, with the use of a suitable propellant. Tablets and capsules may be prepared by any conventional manner known in the art.
- the photosensitiser and the non-photosensitising therapeutic agent may be administered simultaneously, sequentially or separately or in any desired combination thereof. However, these will preferably be administered sequentially or separately in phases (e.g. in two different and/or concurrent phases) of a treatment regime.
- a first phase of treatment involves administration of the photosensitising agent followed by PDT. This is subsequently followed by a second phase of treatment in which the non- photosensitising therapeutic agent is administered.
- administration of the non-photosensitising agent e.g. an anti-infective or anti-cancer agent
- administration of the non-photosensitising agent may be carried out in the conventional manner (e.g.
- a further alternative treatment regime may involve both pre-treatment with 5-ALA based PDT, followed by further courses of 5-ALA based PDT during a course of conventional treatment with a non- photosensitising agent, e.g. an anti-infective or anti-cancer agent.
- a non- photosensitising agent e.g. an anti-infective or anti-cancer agent.
- the individual dosages of photosensitiser and non- photosensitising therapeutic agent required to achieve the desired effect will depend on the mode and route of administration, the agents employed, the disease to be treated, etc.
- the photosensitiser and non-photosensitising agent are provided in the products or kits of the invention in an amount (e.g. dosage form (or dosage forms)) which when used, e.g. in an appropriate dose, in a particular treatment regime provides a combined therapeutic effect which exceeds that which could be obtained by use of the non-photosensitising agent alone.
- the products or kits of the invention comprise the photosensitiser and non-photosensitising agent in an amount (e.g.
- the products or kits of the. invention comprise the photosensitiser and non-photosensitising agent in an amount (e.g. dosage form (or forms)) such that in use, e.g. in an appropriate dose, these have a combined therapeutic effect which exceeds the expected additive therapeutic effect of the non-photosensitising agent alone. and the photosensitiser alone.
- Such an enhanced effect has a number of advantages. Firstly, improved treatment may be achieved and diseases that could not otherwise be treated by either 5-ALA based PDT or the non-photosensitising therapeutic agent alone may become treatable. Secondly, by using 5-ALA based PDT to enhance the effect of the non- photosensitising therapeutic agent, active agents that have essentially become redundant due to the development of resistance may once more be effective. This in turn means that the use of more sophisticated therapeutics may be minimised, thus reducing the potential that cells or micro-organisms may develop a resistance to them. Thirdly, by using 5-ALA based PDT to enhance the effect of the non- photosensitising therapeutic agent, this agent may be used in lower doses thereby minimising any undesirable side effects. Hence in a preferred aspect of the invention, the non-photosensitising therapeutic agent may be provided in a sub- therapeutic dose.
- the total dosage of the non-photosensitising therapeutic agent administered, e.g. by systemic administration, is preferably sub-therapeutic.
- a “subtherapeutic" dose of an agent is meant that less than the amount conventionally known and used for treatment using that agent alone is required.
- the total dosage of the photosensitiser administered in any particular treatment regime may also be sub-therapeutic, e.g: in the range 0.1 to 50 mg/kg, preferably 1 to 10 mg/kg body weight.
- PDT may be carried out by administration of the photosensitiser and then exposing the area to be treated to light to achieve the desired effect of "activating" the cells to treatment by the non-photosensitising agent. This can generally be of the order of a few minutes to 96 hours, preferably 15 minutes to 3 hours. The length of time before light administration is also dependant on the mode of administration, the dose and particular agent employed.
- the wavelength of light used for irradiation may be selected to achieve a more efficacious photosensitizing effect.
- the most effective light is • light in the wavelength range 300-800 nm, typically 400-700 nm.
- the irradiation will in general be applied at a dose level of 10 to 100 Joules/cm 2 with an intensity of 20-200 mW/cm 2 when a laser is used or a dose of 10-lOOJ/cm 2 with an intensity of 50-150m W/cm 2 when a lamp is applied.
- Irradiation is preferably performed for 5 to 30 minutes, preferably for 15 minutes.
- a single irradiation may be used or alternatively a light split dose in which the light dose is delivered in a number of fractions, e.g. a few minutes to a few hours between irradiations, may be used. Multiple irradiations may also be applied.
- the pharmaceutical products and kits herein described may be used in the treatment of various diseases, in particular, in the treatment of infections (e.g. bacterial, fungal, viral and protozoal) and cancer.
- infections e.g. bacterial, fungal, viral and protozoal
- the invention provides a pharmaceutical product or kit as hereinbefore defined for use as a medicament, preferably for the treatment and/or prevention of infections (e.g. bacterial, fungal, viral or protozoal infections) and cancer.
- infections e.g. bacterial, fungal, viral or protozoal infections
- cancer e.g. bacterial, fungal, viral or protozoal infections
- the invention provides the use of a photosensitiser as hereinbefore defined and a non-photosensitising therapeutic agent as hereinbefore defined in the manufacture of a medicament for use in the treatment and/or prevention of infections or cancer.
- a photosensitiser as hereinbefore defined in the manufacture of a medicament comprising said photosensitiser and a non-photosensitising therapeutic agent as hereinbefore defined for use in the treatment and/or prevention of infections or cancer.
- the invention provides the use of a non- photosensitising therapeutic agent as hereinbefore defined in the manufacture of a medicament comprising said therapeutic agent and a photosensitiser as hereinbefore defined for use in the treatment and/or prevention of infections or cancer.
- the invention provides a method of treatment of infection or cancer in a human or non-human animal, said method comprising administering to said animal a product as hereinbefore defined and photoactivating said photosensitiser.
- the pharmaceutical products and kits of the present invention are particularly suitable for use in the treatment of infections and cancers of internal and external body surfaces, e.g. the skin and all other epithelial and serosal surfaces.
- Such surfaces include, for example, mucosa, the linings of organs, e.g. the respiratory, gastro-intestinal and genito-urinary tracts, and glands with ducts which empty onto such surfaces (e.g.
- Such surfaces include for example the lining of the vagina, the endometrium and the urothelium. Such surfaces may also include cavities formed in the body following excision of diseased or cancerous tissue, e.g. brain cavities following the excision of tumours such as gliomas.
- Exemplary surfaces thus include: (i) skin and conjunctiva; (ii) the lining of the mouth, pharynx, oesophagus, stomach, intestines and intestinal appendages, rectum, and anal canal; (iii) the lining of the nasal passages, nasal sinuses, nasopharynx, trachea, bronchi, and bronchioles; (iv) the lining of the ureters, urinary bladder, and urethra; (v) the lining of the vagina, uterine cervix, and uterus; (vi) the parietal and visceral pleura; (vii) the lining of the peritoneal and pelvic cavities, and the surface of the organs contained within those cavities; (viii) the dura mater and meninges; (ix) any tumours in solid tissues that can be made accessible to photoactivating light, e.g. either directly, at the time of surgery, or via an optical fibre
- resistant microorganism a micro-organism that has developed or otherwise acquired a degree of tolerance or immunity to at least one therapeutic agent previously found to be effective in killing or at least in reducing the proliferative activity of said micro- organism.
- resistant or multi-resistant micro-organisms examples include the following: Pathogenic bacteria: Helicobacter pylori (peptic ulcers), Chlamydia trachomatis (genital infections), Staphylococcus aureus (abcesses, skin infections), ;
- pathogenic bacteria Bacillus anthracis, Borrelia burgdorferi, Escherichia coli, Haemophilus influenza, Legionella pneumophila, Viro cholerae, Streptococcus, Neisseria, P. acnes, Enterococci, Acinetobacter baumannii;
- Pathogenic viruses Human papillovirus (skin and mucous menbranes), Rotavirus (enteral), Nordwalk (gastrointestinal), Hantavirus (gastrointestinal);
- Candida oral, vaginal, gastrointestinal
- Giardia lamblia upper small intestine
- Microsporidia gastrointestinal
- Bacterial diseases that may be treated using the pharmaceutical products and kits of the invention include actinomycosis, bacterial vaginosis, biliary-tract infections, cervicitis, chancroid, chlamydial infections, diphtheria, endometritis, epididymitis, gastro-enteritis, gonorrhoea, peritonitis, proctitus, prostatitus, septicaemia, skin infections (e.g.
- Fungal diseases that may be treated using the pharmaceutical products and kits of the invention include aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidomycosis, crytococcosis, dermatophytoses, endocarditus, eye infections, histoplasmosis, infections in immunocompromised patients, meningitis, mucormycosis, mycetoma, nail infections, paracoccidioidomycosis, peritonitis, pityriasis versicolor, Pneumocystis carinii pneumonia, protothecosis, respiratory-tract infections, skin infections, sporotrichosis and tinea.
- aspergillosis blastomycosis, candidiasis, chromoblastomycosis, coccidomycosis, crytococcosis, dermatophytoses, endocarditus, eye infections, histoplasmosis
- Viral diseases that may be treated using the pharmaceutical products and kits of the invention include encephalitis, gastro-enteritis, haemorrhagic fevers, hantavirus pulmonary syndrome, hepatitis, herpes virus infections (e.g. cytomegalovirus infections, Epstein-barr virus infections, herpes simplex infections, , herpesvirus simiae infections, varicella-zoster infections), HIV infections and measles.
- herpes virus infections e.g. cytomegalovirus infections, Epstein-barr virus infections, herpes simplex infections, , herpesvirus simiae infections, varicella-zoster infections
- HIV infections and measles include encephalitis, gastro-enteritis, haemorrhagic fevers, hantavirus pulmonary syndrome, hepatitis, herpes virus infections (e.g. cytomegalovirus infections, Epstein-barr virus infections, herpes simplex infections, , her
- Protozoal diseases that may be treated using the pharmaceutical products and kits of the invention include amoebic infections, acanthamoeba infections, amoebiasis, naegleria infections, babesiosis, balantidiasis, blastocystis hominis infection, coccidiosis, cryptosporidiosis, cyclosporiasis, gastro-enteritis, giardiasis, infections in immunocompromised patients, isosporiasis, leishmaniasis, malaria, microsporidiosis, Pneumocystis carnii pneumonia, toxoplasmosis, trichomoniasis, african trypanosomiasis and american trypanosomiasis.
- Particularly preferred combinations of actives for use in the prevention and/or treatment of infections according to the invention include the following:
- Bacterial infections ALA esters (methyl, hexyl or benzyl) + chloramphenicol, tetracycline (e.g. oxytetracyclin), penicillin derivatives (e.g. phenoxymethylpenicillin, ampicillin, metacillin), cephalosporin derivatives (e.g. cephalexin), fusidinic acid, vancomycin, erythromycin, azelaic acid or metronidazole;
- ALA esters methyl, hexyl or benzyl
- chloramphenicol e.g. oxytetracyclin
- penicillin derivatives e.g. phenoxymethylpenicillin, ampicillin, metacillin
- cephalosporin derivatives e.g. cephalexin
- fusidinic acid vancomycin
- erythromycin erythromycin
- azelaic acid or metronidazole metronidazole
- Viral infections ALA esters (methyl, hexyl or benzyl) + aciclovir, zidovudine or indinavir.
- the pharmaceutical products and kits of the present invention may also be used to treat and/or prevent cancer, in particular drug-resistant or multi-drug resistant cancer.
- drug-resistant cancer is meant a cancer which has become tolerant to conventional treatment with one or more anti-neoplastic agents.
- Cancers that may be treated using the pharmaceutical products and kits of the invention include both malignant and pre-malignant abnormalities, such as for example carcinoid tumours and secretory neoplasms, gestational trophoblastic tumours, histiocytic syndromes, acute leukaemias, chronic leukaemias, lymphomas (e.g.
- Hodgkin's disease mycosis fungoides, noii-Hodgkin's lymphomas, AIDS related lymphoma, Burkitt's syndrome, MALT lymphoma), malignant neoplasms, myeloma, neuroblastoma, polycythaemia vera, retinoblastoma, sarcomas and skin disorders such as actinic keratosis, skin cancer, non-melanoma skin cancer, etc., bladder cancer, colon cancer, rectal cancer, gastric cancer and esophageal cancer.
- the products and kits herein described may be used in treating any of the following: actinic keratosis, non-melanoma skin cancer, bladder cancer, colon cancer, rectal cancer, gastric cancer, and esophageal cancer.
- actives for use in the prevention and/or treatment of cancer according to the invention include the following:
- ⁇ Skin cancer ALA methyl ester + 5-fluorouracil, imiquimod, cytokines or any combination thereof;
- Bladder cancer ALA hexyl ester + mitomycin C and/or epirubicin; Colon cancer: ALA esters (hexyl, benzyl or methyl) + 5-fluorouracil, irenotecan, oxalipatin, leucovorin, levamisole or any combination thereof;
- Rectal cancer ALA esters (hexyl, benzyl or methyl) + 5-fluorouracil and/or leucovorin;
- ALA esters hexyl, benzyl or methyl + 5-fluorouracil, doxorubicin, mitomycin C, cisplatin, epirubicin, etoposide, leucovorin, doxirubicin, methotrexate or any combination thereof;
- Esophageal cancer Esophageal cancer: ALA esters (hexyl, benzyl or methyl) + taxanes, topoisomerase inhibitors, hydroxyurea, vinorelbine or any combination thereof.
- Example 1 Cream comprising 5-aminolevulinic acid methyl ester and 5- fluorouracil for treatment of actinic keratosis
- 5- Fluorouracil is mixed into a cream comprising 20% 5-aminolevulinic acid ester (Metvix® from Photocure ASA, Norway) using a pestle and mortar.
- the final concentration of 5-fluorouracil in the cream is 5 % (w/w).
- the cream is filled into a tube (2 g cream per tube). The cream is topically applied to the affected area of the skin 3 hours prior to photodynamic therapy treatment.
- Example 2 - Kit comprising 5-aminolevulinic acid methyl ester and 5-fluorouracil for treatment of non-melanoma skin cancer
- a cream (20 g) comprising 5-fluorouracil (5-FU) in Unguentum Merck is prepared using a pestle and mortar.
- the final concentration of 5-fluorouracil in the cream is 2 % (w/w).
- This cream is packed together with a tube of Metvix® as a kit with a package insert describing its intended use: "The Metvix® cream is to be used for photodynamic treatment (PDT) on day one.
- the 5-FU cream is to be used twice daily from day 2 for about 2 weeks.
- the combined PDT/5-FU treatment may be repeated as required.”
- Example 3 Kit comprising 5-aminolevulinic acid hexyl ester and Mitomycin for treatment of bladder cancer
- HAL 5-aminolevulinic acid hexyl ester hydrochloride
- the kit has a package insert descibing the use of the product: " follow the instructions for therapeutic use of Hexvix® in week 1. Perform treatment of the bladder cancer with Mutamycin according to the instructions for Mutamycin® in weeks 2, 3 and 4. Repeat both Hexvix® and the Mundamycin® treatment if necessary.”
- Example 4 Cream comprising methyl aminolevulinate (5-aminolevulinic acid methyl ester) and metronidazole for treatment of bacterial infection
- Metronidazole is mixed into a cream comprising 168 mg/g methyl aminolevulinate (Metvix® from Photocure ASA, Norway). The final concentration of metronidazole in the cream is 1 % (w/w). The cream is filled into a tube (2 g cream per tube). The cream is topically applied to the affected area of the skin 3 hours prior to photodynamic therapy treatment.
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Organic Chemistry (AREA)
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Abstract
L'invention concerne un produit pharmaceutique contenant un agent photosensibilisant (5-ALA ou un précurseur ou un dérivé de ce composé), et un agent thérapeutique non photosensibilisant, par exemple 5-fluorouracile, mitromycine, métronidazole etc.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB0609809.9A GB0609809D0 (en) | 2006-05-17 | 2006-05-17 | Product |
GB0609809.9 | 2006-05-17 |
Publications (1)
Publication Number | Publication Date |
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WO2007132234A1 true WO2007132234A1 (fr) | 2007-11-22 |
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PCT/GB2007/001791 WO2007132234A1 (fr) | 2006-05-17 | 2007-05-16 | Compositions pharmaceutiques contenant de l'acide 5-aminolévulinique |
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WO (1) | WO2007132234A1 (fr) |
Cited By (10)
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---|---|---|---|---|
WO2009074811A2 (fr) * | 2007-12-12 | 2009-06-18 | Photocure Asa | Utilisation |
US20110224598A1 (en) * | 2010-03-12 | 2011-09-15 | Daniel Barolet | Radiant near infrared light emitting diode exposure as skin preparation |
JP2012529451A (ja) * | 2009-06-11 | 2012-11-22 | フォトキュア エイエスエイ | 5−アミノレブリン酸を含む固体組成物 |
WO2013053904A1 (fr) * | 2011-10-14 | 2013-04-18 | Photocure Asa | Endoprothèse |
WO2013166318A1 (fr) * | 2012-05-02 | 2013-11-07 | Spectrum Pharmaceuticals, Inc. | Thérapie d'association pour traiter le cancer de la vessie |
EP2767277A1 (fr) * | 2011-10-12 | 2014-08-20 | SBI Pharmaceuticals Co., Ltd. | Agent thérapeutique et/ou agent prophylactique pour des effets secondaires de médicaments anticancéreux |
EP2754439A3 (fr) * | 2007-01-11 | 2014-10-01 | Photocure ASA | Utilisation de dérivés de l'acide Aminolevulinique |
JP5920901B2 (ja) * | 2012-07-19 | 2016-05-18 | Sbiファーマ株式会社 | インフルエンザウイルス感染症の予防・治療剤 |
CN114133398A (zh) * | 2021-12-31 | 2022-03-04 | 中南民族大学 | 氨基酸取代的阿昔洛韦类三环核苷衍生物及其合成方法和应用 |
IT202100015368A1 (it) * | 2021-06-11 | 2022-12-11 | Univ Degli Studi Di Torino | Trattamento terapeutico di tumori tramite blocco dell'asse sintesi-esportazione dell'eme |
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2006
- 2006-05-17 GB GBGB0609809.9A patent/GB0609809D0/en not_active Ceased
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JP2014012725A (ja) * | 2007-12-12 | 2014-01-23 | Photocure Asa | 使用 |
WO2009074811A3 (fr) * | 2007-12-12 | 2009-08-06 | Photocure Asa | Utilisation |
JP2011507808A (ja) * | 2007-12-12 | 2011-03-10 | フォトキュア エイエスエイ | 使用 |
WO2009074811A2 (fr) * | 2007-12-12 | 2009-06-18 | Photocure Asa | Utilisation |
AU2008334426B2 (en) * | 2007-12-12 | 2014-03-27 | Photocure Asa | Use of 5-aminolevulinic acid and derivatives in a solid form for photodynamic treatment and diagnosis |
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US20110224598A1 (en) * | 2010-03-12 | 2011-09-15 | Daniel Barolet | Radiant near infrared light emitting diode exposure as skin preparation |
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