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CO4950609A1 - NEW COMPOUNDS - Google Patents

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Publication number
CO4950609A1
CO4950609A1 CO98021148A CO98021148A CO4950609A1 CO 4950609 A1 CO4950609 A1 CO 4950609A1 CO 98021148 A CO98021148 A CO 98021148A CO 98021148 A CO98021148 A CO 98021148A CO 4950609 A1 CO4950609 A1 CO 4950609A1
Authority
CO
Colombia
Prior art keywords
alkyl
oxygen
formula
group
sulfur
Prior art date
Application number
CO98021148A
Other languages
Spanish (es)
Inventor
Paul Adrian Wyman
Original Assignee
Smithkline Beecham Plc
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 GBGB9707874.5A external-priority patent/GB9707874D0/en
Priority claimed from GBGB9801632.2A external-priority patent/GB9801632D0/en
Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Publication of CO4950609A1 publication Critical patent/CO4950609A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/29—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • 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
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Un compuesto de fórmula (I) o una de sus sales: en la que Ra es un grupo de fórmula (i) en la que p1 es fenilo, arilo bicíclico, un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre, o un anillo heterocíclico bicíclico que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre; R1 es hidrógeno, halógeno, alquilo de C1-6 , cicloalquilo de C3-6 , COalquilo de C1-6 , alcoxi de C1-6 , hidroxi, hidroxialquilo de C1-6 , hidroxialcoxi de C1-6 , alcoxi de C1-6 alcoxi de C1-6 , alcanoilo de C1-6 , nitro, trifluorometilo, ciano, SR9 , SOR9 , SO2 R9 , SO2 NR10 R11 , CO2 R10 , CONR10 R11 , CO2 NR10 R11 , CONR10 (CH2 )c CO2 R11 , (CH2 )c NR10 R11 , (CH2 )c CONR10 R11 , (CH2 )c NR10 COR11 , (CH2 )c CO2alquilo de C1-6 , CO2 (CH2 )c OR10 , NR10 R11 , NR10 CO2 R11 , NR10 CONR10 R11 , CR10 =NOR11 , CNR10 =NOR11 , en las que R9 , R10 y R11 son independientemente hidrógeno o alquilo de C1-6 y c es 1 a 4; R2 es hidrógeno, halógeno, alquilo de C1-6 , cicloalquilo de C3-6 , cicloalquenilo de C3-6 , alcoxi de C1-6 , alcanoilo de C1-6 , arilo, aciloxi, hidroxi, nitro, trifluorometilo, ciano, CO2 R10 , CONR10 R11 , NR10 R11 , en las que R10 y R11 son como se ha definido para R1 ; - 2 -a es 1, 2 ó 3; o Ra es un grupo de fórmula (ii) en la que p2 y P3 son independientemente fenilo, arilo bicíclico, un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre, o un grupo heterocíclico bicíclico que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno o azufre; A es un enlace u oxígeno, S(O)m en cuya fórmula m es 0 a 2, carbonilo, o CH2 o NR4 en cuya fórmula R4 es hidrógeno o alquilo de C1-6 ; R1 es como se ha definido anteriormente para la fórmula (i) o R1 es un anillo heterocíclico de 5 a 7 miembros, que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno o azufre, opcionalmente sustituido con alquilo de C1-6 , halógeno o alcanoilo de C1-6 ; R2 y R3 son independientemente hidrógeno, halógeno, alquilo de C1-6 , cicloalquilo de C3-6 , cicloalquenilo de C3-6 , alcoxi de C1-6 , alcanoilo de C1-6 , arilo, aciloxi, hidroxi, nitro, trifluorometilo, ciano, CO2 R10 , CONR10 R11 , NR10 R11 en cuyas fórmulas R10 y R11 son como se ha definido para R1 ; y a y b son independientemente 1, 2 ó 3; L es un grupo de fórmula -Y-C(=V)-DG- en la que Y es -NH-, NR5 en la que R5 es alquilo de C1-6 , o Y es -CH2 - u -O-; V es oxígeno o azufre;D es nitrógeno, carbono o un grupo CH, G es hidrógeno o alquilo de C1-6 , con tal que D sea nitrógeno o un grupo CH, o G junto con Rb1 forma un grupo W en el que W es (CR16 R17 )t en cuya fórmula t es 2, 3 ó 4, y R16 y R17 son independientemente hidrógeno o alquilo de C1-6 o W es (CR16 R17 )u AND#8209;J en cuya fórmula u es 0, 1, 2 ó 3 y J es oxígeno, azufre, CR16 =CR17 , CR16 =N, CR16 O, =CR16 S o =CR16 -NR17 ;B es CH2 , oxígeno, S(O)p en cuya fórmula p es 0, 1 ó 2, NR6 en la que R6 es hidrógeno o alquilo de C1-6 o B es CR7 =CR8 en la que R7 y R8 son independientemente hidrógeno o alquilo de C1-6 ;Rc y Rd son independientemente hidrógeno o alquilo de C1-6 ;RY es un anillo heterocíclico de 5 a 7 miembros que contiene 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre, o RY es un grupo de fórmula AND#8209;NRe Rf en la queRe y Rf son independientemente hidrógeno, alquilo de C1-6 o aralquilo;Rb1 y Rb2 son independientemente hidrógeno, halógeno, hidroxi, alquilo de C1-6 , trifluorometilo, alcoxi de C1-6 o arilo, o Rb1 junto con G forma un grupo W según se ha definido anteriormente, y n es 0, 1, 2, 3 ó 4.A compound of formula (I) or a salt thereof: where Ra is a group of formula (i) where p1 is phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 selected heteroatoms between oxygen, nitrogen and sulfur, or a bicyclic heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur; R1 is hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, CO C1-6alkyl, C1-6 alkoxy, hydroxy, C1-6 hydroxyalkyl, C1-6 hydroxyalkoxy, C1-6 alkoxy alkoxy C1-6, C1-6 alkanoyl, nitro, trifluoromethyl, cyano, SR9, SOR9, SO2 R9, SO2 NR10 R11, CO2 R10, CONR10 R11, CO2 NR10 R11, CONR10 (CH2) c CO2 R11, (CH2) c NR10 R11, (CH2) c CONR10 R11, (CH2) c NR10 COR11, (CH2) c CO2 C1-6 alkyl, CO2 (CH2) c OR10, NR10 R11, NR10 CO2 R11, NR10 CONR10 R11, CR10 = NOR11, CNR10 = NOR11, where R9, R10 and R11 are independently hydrogen or C1-6 alkyl and c is 1 to 4; R2 is hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 alkoxy, C1-6 alkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2 R10 , CONR10 R11, NR10 R11, where R10 and R11 are as defined for R1; - 2 -a is 1, 2 or 3; or Ra is a group of formula (ii) in which p2 and P3 are independently phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, or a bicyclic heterocyclic group that it contains 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur; A is a bond or oxygen, S (O) m in whose formula m is 0 to 2, carbonyl, or CH2 or NR4 in whose formula R4 is hydrogen or C1-6 alkyl; R1 is as defined above for formula (i) or R1 is a 5-7 membered heterocyclic ring, containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur, optionally substituted with C1-6 alkyl, halogen or C1-6 alkanoyl; R2 and R3 are independently hydrogen, halogen, C1-6 alkyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, C1-6 alkoxy, C1-6 alkanoyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano , CO2 R10, CONR10 R11, NR10 R11 in whose formulas R10 and R11 are as defined for R1; and a and b are independently 1, 2 or 3; L is a group of formula -Y-C (= V) -DG- where Y is -NH-, NR5 where R5 is C1-6 alkyl, or Y is -CH2 - or -O-; V is oxygen or sulfur; D is nitrogen, carbon or a CH group, G is hydrogen or C1-6 alkyl, provided that D is nitrogen or a CH group, or G together with Rb1 forms a group W in which W is (CR16 R17) t in whose formula t is 2, 3 or 4, and R16 and R17 are independently hydrogen or C1-6 alkyl or W is (CR16 R17) or AND # 8209; J in whose formula u is 0, 1, 2 or 3 and J is oxygen, sulfur, CR16 = CR17, CR16 = N, CR16 O, = CR16 S or = CR16 -NR17; B is CH2, oxygen, S (O) p in whose formula p is 0, 1 or 2, NR6 where R6 is hydrogen or C1-6 alkyl or B is CR7 = CR8 where R7 and R8 are independently hydrogen or C1-6 alkyl; Rc and Rd are independently hydrogen or C1- alkyl 6; RY is a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, or RY is a group of formula AND # 8209; NRe Rf where Re and Rf are independently hydrogen, alkyl of C1-6 or aralkyl; Rb1 and Rb2 are independently hydr geno, halogen, hydroxy, C1-6alkyl, trifluoromethyl, C1-6alkoxy or aryl, or Rb1 together with G forms a group W as defined above, and n is 0, 1, 2, 3 or 4.

CO98021148A 1997-04-18 1998-04-17 NEW COMPOUNDS CO4950609A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9707874.5A GB9707874D0 (en) 1997-04-18 1997-04-18 Novel compounds
GBGB9801632.2A GB9801632D0 (en) 1998-01-26 1998-01-26 Novel compounds

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AR (1) AR012450A1 (en)
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WO (1) WO1998050346A2 (en)

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