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AR031867A1 - COMPOUNDS DERIVED FROM PHENOXIBENCILAMINE AS SSRI, ITS USE IN THE PREPARATION OF MEDICINES, PROCEDURE OF PREPARATION OF THE COMPOUND AND USEFUL INTERMEDIARIES - Google Patents

COMPOUNDS DERIVED FROM PHENOXIBENCILAMINE AS SSRI, ITS USE IN THE PREPARATION OF MEDICINES, PROCEDURE OF PREPARATION OF THE COMPOUND AND USEFUL INTERMEDIARIES

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Publication number
AR031867A1
AR031867A1 ARP010104114A ARP010104114A AR031867A1 AR 031867 A1 AR031867 A1 AR 031867A1 AR P010104114 A ARP010104114 A AR P010104114A AR P010104114 A ARP010104114 A AR P010104114A AR 031867 A1 AR031867 A1 AR 031867A1
Authority
AR
Argentina
Prior art keywords
alkyl
compounds
preparation
heterocyclic ring
independently substituted
Prior art date
Application number
ARP010104114A
Other languages
Spanish (es)
Original Assignee
Pfizer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0021593A external-priority patent/GB0021593D0/en
Priority claimed from GB0107116A external-priority patent/GB0107116D0/en
Application filed by Pfizer filed Critical Pfizer
Publication of AR031867A1 publication Critical patent/AR031867A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Reproductive Health (AREA)
  • Pain & Pain Management (AREA)
  • Gynecology & Obstetrics (AREA)
  • Addiction (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un compuesto derivado de fenoxibencilamina de formula general (1), sus sales, solvatos o polimorfos farmacéuticamente aceptables, donde: R1 y R2, que pueden ser iguales o diferentes, son H, alquilo C1-6 o (CH2)d-cicloalquilo C3-6, donde d es 0, 1, 2 o 3; o R1 y R2 junto con el nitrogeno al que están unidos forman un anillo de azetidina; uno de Z o Y es -SR3 y el otro de Z o Y es halogeno o -R3; donde R3 es independientemente alquilo C1-4 opcionalmente sustituido con fluor; excepto que R3 no es CF3; o Z e Y están unidos de manera que, junto con los átomos de interconexion, Z e Y forman un anillo carbocíclico o heterocíclico de 5 a 7 miembros, condensado, que puede ser saturado, insaturado o aromático, y donde, cuando Z e Y forman un anillo heterocíclico, además de átomos de C, el enlace contiene uno o dos heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrogeno; con la condicion que cuando R5 es fluor y R2 es metilo, entonces el anillo condensado no es 1,3-dioxolano y Z e Y juntos no forman un anillo de fenilo condensado; R4 y R5, que pueden ser iguales o diferentes, son: A-X, donde A es -CH=CH- o -(CH2)p-, donde p es 0, 1 o 2; X es hidrogeno, F, Cl, Br, I, CONR6R7, SO2NR6R7, SO2NHC(=O)R6, OH, alcoxi C1-4, NR8SO2R9, NO2, NR6R11, CN, CO2R10, CHO, SR10, S(O)R9, o SO2R10; R6, R7, R8 y R10, que pueden ser iguales o diferentes, son hidrogeno o alquilo C1-6 opcionalmente sustituido independientemente con uno o más R12; R9 es alquilo C1-6 opcionalmente sustituido independientemente con uno o más R12, R11 es hidrogeno, alquilo C1-6 opcionalmente sustituido independientemente con uno o más R12, C(O)R6, CO2R9, C(O)NHR6 o SO2NR6R7; R12 es F, OH, CO2H, cicloalquilo C3-6, NH2, CONH2, alcoxi C1-6, alcoxi C1-6-carbonilo o un anillo heterocíclico de 5 o 6 miembros que contiene 1, 2 o 3 heteroátomos seleccionados entre N, S y O, opcionalmente sustituido independientemente con uno o más R13; o R6 y R7, junto con el nitrogeno al que están unidos, forman un anillo heterocíclico de 4, 5 o 6 miembros opcionalmente sustituido independientemente con uno o más R13; o un anillo heterocíclico de 5 o 6 miembros que contiene 1, 2 o 3 heteroátomos seleccionados entre N, S y O, opcionalmente sustituido independientemente con uno o más R13; donde R13 es hidroxi, alcoxi C1-4, F, alquilo C1-6, haloalquilo, haloalcoxi, -NH2, -NH(alquilo C1-6) o -N(alquilo C1-6)2. Compuestos de éter difenílico que inhiben la reabsorcion de monoaminas. En particular los compuestos presentan actividad como inhibidores selectivos de la reabsorcion de serotonina (SSRI, del inglés selective serotonin re-uptake inhibitors) y tienen utilidad, por tanto en diversas áreas terapéuticas. Más notablemente, los compuestos de la presente son utiles en el tratamiento o prevencion de diversos trastornos, incluidos aquellos en los que está implicada la regulacion de la funcion de los transportadores de monoaminas, tales como depresion, trastorno de hiperactividad con déficit de atencion, trastorno obsesivo compulsivo, trastorno de estrés post-traumático, trastornos de abuso de sustancias y disfuncion sexual, incluida eyaculacion precoz, y a las formulaciones farmacéuticas que contienen tales compuestos. Se describe también su uso en la preparacion de medicamentos, proceso para la preparacion de los compuestos e intermediarios utiles en su fabricacion.A compound derived from phenoxybenzylamine of general formula (1), its pharmaceutically acceptable salts, solvates or polymorphs, where: R1 and R2, which may be the same or different, are H, C1-6 alkyl or (CH2) d-cycloalkyl C3- 6, where d is 0, 1, 2 or 3; or R1 and R2 together with the nitrogen to which they are attached form an azetidine ring; one of Z or Y is -SR3 and the other of Z or Y is halogen or -R3; where R3 is independently C1-4 alkyl optionally substituted with fluorine; except that R3 is not CF3; or Z and Y are attached so that, together with the interconnection atoms, Z and Y form a condensed, 5- to 7-membered carbocyclic or heterocyclic ring, which can be saturated, unsaturated or aromatic, and where, when Z and Y they form a heterocyclic ring, in addition to C atoms, the bond contains one or two heteroatoms independently selected from oxygen, sulfur and nitrogen; with the proviso that when R5 is fluorine and R2 is methyl, then the condensed ring is not 1,3-dioxolane and Z and Y together do not form a condensed phenyl ring; R4 and R5, which may be the same or different, are: A-X, where A is -CH = CH- or - (CH2) p-, where p is 0, 1 or 2; X is hydrogen, F, Cl, Br, I, CONR6R7, SO2NR6R7, SO2NHC (= O) R6, OH, C1-4 alkoxy, NR8SO2R9, NO2, NR6R11, CN, CO2R10, CHO, SR10, S (O) R9, or SO2R10; R6, R7, R8 and R10, which may be the same or different, are hydrogen or C1-6 alkyl optionally independently substituted with one or more R12; R9 is C1-6 alkyl optionally independently substituted with one or more R12, R11 is hydrogen, C1-6 alkyl optionally substituted independently with one or more R12, C (O) R6, CO2R9, C (O) NHR6 or SO2NR6R7; R12 is F, OH, CO2H, C3-6 cycloalkyl, NH2, CONH2, C1-6 alkoxy, C1-6 alkoxycarbonyl or a 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, S and O, optionally independently substituted with one or more R13; or R6 and R7, together with the nitrogen to which they are attached, form a 4, 5 or 6-membered heterocyclic ring optionally independently substituted with one or more R13; or a 5 or 6 membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, S and O, optionally independently substituted with one or more R13; where R13 is hydroxy, C1-4 alkoxy, F, C1-6 alkyl, haloalkyl, haloalkoxy, -NH2, -NH (C1-6 alkyl) or -N (C1-6 alkyl) 2. Diphenyl ether compounds that inhibit the reabsorption of monoamines. In particular, the compounds have activity as selective serotonin reuptake inhibitors (SSRIs) and are useful, therefore in various therapeutic areas. Most notably, the compounds herein are useful in the treatment or prevention of various disorders, including those in which the regulation of the function of monoamine transporters is involved, such as depression, attention deficit hyperactivity disorder, disorder Obsessive compulsive, post-traumatic stress disorder, substance abuse disorders and sexual dysfunction, including premature ejaculation, and to pharmaceutical formulations containing such compounds. Its use is also described in the preparation of medicines, process for the preparation of compounds and useful intermediates in its manufacture.

ARP010104114A 2000-08-31 2001-08-29 COMPOUNDS DERIVED FROM PHENOXIBENCILAMINE AS SSRI, ITS USE IN THE PREPARATION OF MEDICINES, PROCEDURE OF PREPARATION OF THE COMPOUND AND USEFUL INTERMEDIARIES AR031867A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0021593A GB0021593D0 (en) 2000-08-31 2000-08-31 Diphenyl ether compounds useful in therapy
GB0107116A GB0107116D0 (en) 2001-03-21 2001-03-21 Novel compounds

Publications (1)

Publication Number Publication Date
AR031867A1 true AR031867A1 (en) 2003-10-08

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EP (1) EP1313701A1 (en)
JP (1) JP2004507523A (en)
KR (1) KR20030029889A (en)
CN (1) CN1449380A (en)
AP (1) AP2001002265A0 (en)
AR (1) AR031867A1 (en)
AU (1) AU2001278650A1 (en)
BG (1) BG107544A (en)
BR (1) BR0113610A (en)
CA (1) CA2420969A1 (en)
CZ (1) CZ2003467A3 (en)
DO (1) DOP2001000242A (en)
DZ (1) DZ3414A1 (en)
EA (1) EA200300206A1 (en)
EE (1) EE200300084A (en)
HN (1) HN2001000191A (en)
HR (1) HRP20030141A2 (en)
HU (1) HUP0303385A2 (en)
IL (1) IL154343A0 (en)
IS (1) IS6704A (en)
MA (1) MA26945A1 (en)
MX (1) MXPA03001848A (en)
NO (1) NO20030842L (en)
NZ (1) NZ523951A (en)
OA (1) OA12372A (en)
PA (1) PA8526701A1 (en)
PE (1) PE20020346A1 (en)
PL (1) PL360743A1 (en)
SK (1) SK2012003A3 (en)
TN (1) TNSN01131A1 (en)
UY (1) UY26924A1 (en)
WO (1) WO2002018333A1 (en)

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