AR068893A1 - Proceso para sintetizar compuestos derivados de acido fosfonico y acido fosfinico - Google Patents
Proceso para sintetizar compuestos derivados de acido fosfonico y acido fosfinicoInfo
- Publication number
- AR068893A1 AR068893A1 ARP080104508A ARP080104508A AR068893A1 AR 068893 A1 AR068893 A1 AR 068893A1 AR P080104508 A ARP080104508 A AR P080104508A AR P080104508 A ARP080104508 A AR P080104508A AR 068893 A1 AR068893 A1 AR 068893A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- alkoxy
- optionally substituted
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 13
- 238000000034 method Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 32
- 125000001424 substituent group Chemical group 0.000 abstract 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 17
- -1 -N-C1-6 dialkyl Chemical group 0.000 abstract 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 14
- 229910052736 halogen Inorganic materials 0.000 abstract 12
- 150000002367 halogens Chemical class 0.000 abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract 10
- 239000001257 hydrogen Substances 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 9
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 abstract 9
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 7
- 125000004429 atom Chemical group 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000004104 aryloxy group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001721 carbon Chemical group 0.000 abstract 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 abstract 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- SEQLHCOPAWAOAU-SNAWJCMRSA-N [1-(5-chloro-1-benzothiophen-3-yl)-2-[[(e)-2-(3,5-dichlorophenyl)ethenyl]amino]-2-oxoethyl]-methylphosphinic acid Chemical compound C=1SC2=CC=C(Cl)C=C2C=1C(P(O)(=O)C)C(=O)N\C=C\C1=CC(Cl)=CC(Cl)=C1 SEQLHCOPAWAOAU-SNAWJCMRSA-N 0.000 abstract 1
- AAWWTPVQFZNTEM-ONEGZZNKSA-N [1-(5-chloro-1-benzothiophen-3-yl)-2-[[(e)-2-(3,5-dichlorophenyl)ethenyl]amino]-2-oxoethyl]phosphonic acid Chemical compound C=1SC2=CC=C(Cl)C=C2C=1C(P(O)(=O)O)C(=O)N\C=C\C1=CC(Cl)=CC(Cl)=C1 AAWWTPVQFZNTEM-ONEGZZNKSA-N 0.000 abstract 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000005018 aryl alkenyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
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- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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Abstract
La presente se refiere a un proceso mejorado para sintetizar compuestos inhibidores de quimasa del ácido fosfonico y fosfínico. Reivindicacion 1: Un proceso para preparar un compuesto de formula (1) una sal del mismo, donde el anillo A se selecciona independientemente del grupo integrado por arilo, heteroarilo, y, heterociclilo fusionado con benzo, opcionalmente sustituido con R2 y R3; R2 es uno a tres sustituyentes seleccionados independientemente del grupo integrado por alquilo C1-4, metoxi, alcoxi C2-6, -OCH2-alquenilo C2-6, NH2, -NH(alquilo C1-6), -N-dialquilo C1-6, arilo, heteroarilo, halogeno, hidroxi, y nitro, donde dichos sustituyentes alquilo C1-4, alquenilo C2-6 y alcoxi C2-6 de R2 están opcionalmente sustituidos con un sustituyente seleccionado independientemente del grupo integrado por -NR11R12, arilo, heteroarilo, uno a tres halogenos e hidroxi; R11 y R12 son sustituyentes seleccionados independientemente del grupo integrado por hidrogeno, alquilo C1-6, y arilo; donde dicho sustituyente alquilo C1-6 de R11 o es opcionalmente sustituido con un sustituyente seleccionado del grupo integrado por hidroxi, arilo, -C(=O)alcoxi C1-4, y NR15R16; R15 y R16 son sustituyentes seleccionados independientemente del grupo integrado por hidrogeno, alquilo C1-6, y arilo, y dicho R15 y R16 se toman opcionalmente juntos con los átomos a los cuales están unidos para formar un anillo de cinco a siete miembros; R3 es uno a tres sustituyentes seleccionados independientemente del grupo integrado por alquilo C1-6, alquenilo C2-6, alcoxi C1-6, -OCH2-alquenilo C2-6, NH2, -NH(alquilo C1-6), -N-dialquilo C1-6, -NHC(=O)Cy, -N(alquilo C1-6)C(=O)Cy, -C(=O)alcoxi C1-4, -C(=O)NR17R18, -C(=O)NH-cicloalquilo, -C(=O)N-alquilo C1-6-cicloalquilo, -C(=O)NHCy, -C(=O)N(alquilo C1-6)Cy, -C(=O)Cy, -OC(=O)NR19R20, halogeno, hidroxi, nitro, ciano, arilo y ariloxi, donde dicho -alquilo C1-6 y alcoxi C1-6 están opcionalmente sustituidos con uno a tres sustituyentes seleccionados independientemente del grupo integrado por -NR21R22, -NH-cicloalquilo, -N(alquil C1-6)cicloalquilo, -NHCy, -N(alquilo C1-6)Cy, -NHC(O)-alquilo C1-6-alcoxi C1-6, arilo, heteroarilo, halogeno, -C(=O)NR23R24, -OC(=O)NR25R26, -C(=O)alcoxi C1-4, y -C(=O)Cy, donde cada instancia de dicho alquenilo C2-6 está opcionalmente sustituido sobre un carbono terminal con arilo o -C(=O)NR27R28, y donde dicho arilo y cicloalquilo están opcionalmente sustituidos con uno a tres sustituyentes independientemente seleccionados de R14; R14 es independientemente hidrogeno, alquilo C1-6, alcoxi C1-6, alquenilo C2-6, alquiltio C1-6, -NH2, -NH-alquilo C1-6, -N-dialquilo C1-6, arilo, heteroarilo, ariloxi, heteroariloxi, halogeno, hidroxi, o nitro, y cualquiera de los anteriores sustituyentes que contienen alquilo C1-6 o alcoxi C1-6 de R14 está opcionalmente sustituido sobre un átomo de carbono terminal con un sustituyente seleccionado de -NR29R30, arilo, heteroarilo, uno a tres átomos de halogeno, o hidroxi; R17, R18, R19, R20, R21, R22, R23, R24, R25 y R26 son sustituyentes seleccionados independientemente del grupo integrado por hidrogeno, alquilo C1-6 y arilo, donde alquilo C1-6 y arilo están cada uno de ellos opcionalmente sustituidos con hidroxi, arilo, ariloxi, -C(=O)-arilo, -C(=O)alcoxi C1-4, NH2, -NH(alquilo C1-6), o -N-dialquilo C1-6; y dicho R17 y R18, R19 y R20, R21 y R22, R23 y R24 o R25 y R26 se toman opcionalmente juntos con los átomos a los cuales están unidos para formar un anillo de cinco a siete miembros; R27 y R28 son independientemente hidrogeno; alquilo C1-6 opcionalmente sustituido con hidroxi, arilo, -C(=O)alcoxi C1-4, NH2, -NH(alquilo C1-6) o -N-dialquilo C1-6; o arilo; y dicho R27 y R28 se toman opcionalmente juntos con los átomos a los cuales están unidos para formar un anillo de cinco a siete miembros; R29 y R30 son independientemente hidrogeno; alquilo C1-6 opcionalmente sustituido con hidroxi, arilo, -C(=O) alcoxi C1-4, NH2, -NH-alquilo C1-6, o -N-dialquilo C1-6; o arilo; y R29 y R30 se toman opcionalmente juntos con los átomos a los cuales están unidos para formar un anillo de cinco a siete miembros; Cy es un heterociclilo opcionalmente sustituido con un sustituyente seleccionado del grupo integrado por oxo, alquilo C1-6, -alquilo C1-6C(=O)-alquilo C1-6, -alquilo C1-6C(=O)-alcoxi C1-6, -alquil C1-6-arilo, -alquilo C1-6C(=O)arilo, -C(=O)-alquilo C1-6, -C(=O)alcoxi C1-6, -C(=O)arilo, -SO2-arilo, arilo, heteroarilo y heterociclilo, donde arilo y la porcion arilo de -alquilo C1-6C(=O)arilo, -C(=O)arilo y -SO2-arilo están opcionalmente sustituidos con uno a tres sustituyentes seleccionados independientemente del grupo integrado por alquilo C1-6, alcoxi C1-6, halogeno, hidroxi, NH2, -NH(alquilo C1-6), y -N-dialquilo C1-6; y donde heterociclilo es opcionalmente sustituido con arilo, uno a tres átomos de halogeno, o uno a tres oxo sustituyentes; y, donde heterociclilo está opcionalmente espirofusionado a dicho Cy; R5 se selecciona del grupo integrado por hidrogeno o alquilo C1-3 opcionalmente sustituido con NH2, -NH-alquilo C1-6, -N-dialquilo C1-6, alquil C1-6carboniloxi-, alcoxi C1-6carboniloxi-, alquil C1-6carboniltio-, alquilamino C1-6carbonilo-, dialquilamino C1-6carbonilo-, uno a tres halogenos, o hidroxi; y dicho arilo es opcionalmente sustituido con alquilo C1-6, alcoxi C1-6, alquiltio C1-6-, alquenilo C2-6, NH2, -NH-alquilo C1-6, -N-dialquilo C1-6, arilo, heteroarilo, ariloxi, heteroariloxi, halogeno, hidroxi, o nitro; en forma alternativa, cuando R6 es alcoxi C1-8, dicho R5 y R6 se toman juntos con los átomos a los cuales están unidos para formar un anillo monocíclico de 5 a 8 miembros, siempre que R5 es diferente de alquilo C1-3 sustituido con dialquilamino C1-6carbonilo- cuando el sistema anular A es 3,4-difluoro-fenilo, n es 1, R6 es OH, y Z-R4 es 5-cloro-benzotiofen-3-ilo; y siempre que R5 es diferente de alquilo C1-3 sustituido con alquil C1-6carboniltio- cuando el sistema anular A es 3,4-difluoro-fenilo, n es 1, R6 es CH3, y Z-R4 es 5-cloro-benzotiofen-3-ilo; R6 se selecciona del grupo integrado por alquilo C1-6, alcoxi C1-8, heteroarilo, arilo, e hidroxi; donde alquilo C1-6 está opcionalmente sustituido sobre un átomo de carbono terminal con un sustituyente seleccionado de alcoxi C1-3, arilo, o hidroxi; y alcoxi C1-8 está opcionalmente sustituido sobre un átomo de carbono terminal con un sustituyente seleccionado independientemente del grupo integrado por alquil C1-6carboniloxi- y dialquilamino C1-6carbonilo-; y donde heteroarilo y arilo están opcionalmente sustituidos con uno a tres sustituyentes seleccionados independientemente del grupo integrado por arilo, hidroxi, alcoxi C1-6, y halogeno; Z es un arilo bicíclico o heteroarilo bicíclico; donde arilo y heteroarilo están opcionalmente sustituidos con el grupo R4; R4 es uno a tres sustituyentes seleccionados del grupo integrado por alquilo C1-6, alquenilo C2-6, alcoxi C1-6, arilalquenilo C2-6, halogeno, -C(=O)Cy, -C(=O)NR31R32, arilo, -CO2H, oxo y ciano, donde dicho alquilo C1-6, alquenilo C2-6 y alcoxi C1-6 están opcionalmente sustituidos con un sustituyente seleccionado independientemente del grupo integrado por -NR33R34, arilo, uno a tres átomos de halogeno e hidroxi, y donde dicho arilo es opcionalmente sustituido con un sustituyente seleccionado independientemente del grupo integrado por hidrogeno, alquilo C1-6, alcoxi C1-6, arilo, halogeno, hidroxi, y nitro; y R31, R32, R33 y R34 son sustituyentes seleccionados independientemente del grupo integrado por hidrogeno, alquilo C1-6, y arilo, donde alquilo es opcionalmente sustituido con hidroxi, arilo, -C(=O)alcoxi C1-4, NH2, NH(alquilo C1-6), o -N-dialquilo C1-6; y dicho R31 y R32 o R33 y R34 se toman opcionalmente juntos con os átomos a los cuales están unidos para formar un anillo de cinco a siete miembros; que comprende los pasos de: Paso 1) hacer reaccionar un compuesto A1 (donde R5 es alquilo C1-3) con un compuesto A2, donde el compuesto A1 y el compuesto A2 están presentes en una primera relacion en tolueno para dar un compuesto A3 (donde R5 es alquilo C1-3), representativo de un compuesto de formula (1), Reaccion (2); Paso 2) hacer reaccionar el compuesto A3 (donde R5 es alquilo C1-3) en presencia de TMSBr en acetonitrilo y opcionalmente presente piridina, donde TMSBr y el compuesto A3 están en una segunda relacion, y donde TMSBr y piridina, cuando piridina está presente, están en una tercera relacion para dar un compuesto A4 (donde R5 es hidrogeno), representativo de un compuesto de la reivindicacion 1, Reaccion (3); donde en la segunda relacion, TMSBr y el compuesto A3 están en un rango de aproximadamente 2,5:1 TMSBr:compuesto A3 hasta aproximadamente 2:1 TMSBr:compuesto A3 y donde en la tercera relacion, TMSBr y piridina, cuando piridina está presente, están en un rango desde aproximadamente 1:1 TMSBr:piridina hasta aproximadamente 1:2 TMSBr:piridina. Reivindicacion 10: El proceso de la reivindicacion 9, donde el compuesto se selecciona del grupo integrado por: 2) ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(34-difluoro-fenil)-vinilcarbamoil]-metil}-fosfonico, 17) ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(3,4-difluoro-fenil)-vinilcarbamoil]-metil}-metil-fosfínico; 164) ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(3,5-dicloro-fenil)-vinilcarbamoil]-metil}-metil-fosfínico; 181) (ter-butilcarboniloximetil) éster del ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(3,4-difluoro-fenil)-vinilcarbamoil]-metil}-fosfonico; 185) [(isopropoxicarboniIoxi)-metil] éster del ácido (E)-{(5-cloro-benzo[b]tiofen-3-iI)[2(3,4-difluoro-fenil)-vinilcarbamoil]-metil}-fosfonico; 201) ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(3,5-dicloro-fenil)-vinilcarbamoil]-metil}-fosfonico; 255) (ter-butilcarboniloximetil) éster del ácido (E)-{(5-cloro-benzo[b]tiofen-3-il)-[2-(3,5-dicloro-fenil)-vinilcarbamoil]-metil}-fosfonico y 291) (isopropiloxicarboniloximetil) éster del ácido (E)-{(5-cloro-benzo[b)tiofen-3-il)-[2-(3,5-dicloro-fenil)-vinilcarbamoil]-metil}-fosfonico. Un proceso p
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