AR064650A1 - AGONIST AND ANTAGONIST COMPOUNDS OF THE SPHINGOSINE-1-PHOSPHATE RECEPTOR - Google Patents

AGONIST AND ANTAGONIST COMPOUNDS OF THE SPHINGOSINE-1-PHOSPHATE RECEPTOR

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Publication number
AR064650A1
AR064650A1 ARP070105818A ARP070105818A AR064650A1 AR 064650 A1 AR064650 A1 AR 064650A1 AR P070105818 A ARP070105818 A AR P070105818A AR P070105818 A ARP070105818 A AR P070105818A AR 064650 A1 AR064650 A1 AR 064650A1
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AR
Argentina
Prior art keywords
substituted
alkyl
optionally substituted
independently
branched
Prior art date
Application number
ARP070105818A
Other languages
Spanish (es)
Inventor
Kevin P Cusack
Shannon R Fix-Stenzel
Grier A Wallace
Eric C Breinlinger
Graham K Ansell
Thomas D Gordon
Adrian D Hobson
Martin E Hayes
Original Assignee
Abbott Lab
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39562856&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR064650(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Abbott Lab filed Critical Abbott Lab
Publication of AR064650A1 publication Critical patent/AR064650A1/en

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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
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    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
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    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
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    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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    • 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
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    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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    • C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • 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, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
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    • 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
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    • 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
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    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Abstract

Agentes potentes y selectivos, que son agonistas o antagonistas de los uno o más de los receptores individuales de la familia de receptores de SIP. Los compuestos de la invencion son utiles como terapéuticos para tratar condiciones médicas asociadas con el agonismo o antagonismo de los receptores individuales de la familia de receptores de SIP. Reivindicacion 1: Un compuesto de la formula (1) caracterizado porque D es H, N(R5)2 o OR6; X es CH, C(CH3) o N; Y es CH2, O, S o NR3; donde R3 es hidrogeno, o alquilo (C1-10) lineal o ramificado; A es H, hidroxi, -CH2OH, -CH(OH)CH3, -C(O)-OCH3, -C(OH)(CH3)2, -O(CH2)t-COOH, -C(O)-NR6, -(CH2)n-P(=O)(OR7)(OR7) opcionalmente sustituido, -(CH2)n-O-P(=O)(OR7)(OR7) opcionalmente sustituido, -(CH2)n- O-P(=O)(OR7)(R7) opcionalmente sustituido, -CH=CH-P(=O)(OR7)(OR1), C(O)NHCH3, CN, COOR6 o -R4-COOH, donde R4 es alquileno (C1-20) lineal o ramificado, alquenileno (C1-20) lineal o ramificado, alquinileno (C1-20) lineal o ramificado, cicloalquilo (C3- 20), o azetidinilo opcionalmente sustituido; R1 y R2 se seleccionan independientemente entre el grupo que consiste en hidrogeno, CF3, halogeno, alquilo (C1-20), alcoxi (C1-20), cicloalquil-aIquilo (C3-20) sustituido, cicloalquilalcoxi (C3-20) sustituido, alquenilo (C2-20), arilalquenilo (C2-20) sustituido, alquinilo (C2-20), aril-alquinilo (C2-20) sustituido, arilo, aril-alquilo (C1-20) sustituido, heteroaril-alquilo (C2-20) sustituido, aril alcoxi sustituido, heteroaril alcoxi sustituido, alquil arilo sustituido, arilalquilo, aril arilalquilo sustituido, arilalquil arilalquilo sustituido, CN y -O-indolizinilo; donde dichos grupos y R2 pueden estar sustituidos opcionalmente con uno o más sustituyentes que se seleccionan independientemente entre alquilo (C1-20), CF3, halogeno, hidroxi, alcoxi (C1-20), OCF3, y CN; donde uno o más de los átomos de carbono en los grupos R1o R2 se pueden reemplazar independientemente por oxigeno no perteneciente a un peroxido, azufre o NR8; donde R8 es hidrogeno o un grupo alquilo (C1-20); donde uno de R1 y R2 es diferente de hidrogeno; y donde los grupos alquilo, alquenilo, y alquinilo en R1 y R2 están sustituidos opcionalmente con los grupos oxo o halo; cada R5 es independientemente H, alquilo (C1-3) opcionalmente sustituido, o -C(O)-O-alquilo (C1-3)fenilo opcionalmente sustituido; cada R6 es independientemente H o alquilo (C1-2) opcionalmente sustituido; cada R7 es independientemente H, alquilo (C1-2) opcionalmente sustituido o fenilo opcionalmente sustituido; m es 1 o 2; n es 1, 2 o 3; t es 1, 2 o 3; y u es 0, 1 o 2; con la condicion de que A y D no deben ser ambos H al mismo tiempo; y con la condicion de que el compuesto no debe ser (2) donde X es CH o N; Y es CH2, NH, N(CH3), S u O.Powerful and selective agents, which are agonists or antagonists of the one or more of the individual receptors of the SIP receptor family. The compounds of the invention are useful as therapeutic to treat medical conditions associated with agonism or antagonism of the individual receptors of the SIP receptor family. Claim 1: A compound of the formula (1) characterized in that D is H, N (R5) 2 or OR6; X is CH, C (CH3) or N; Y is CH2, O, S or NR3; where R3 is hydrogen, or linear or branched (C1-10) alkyl; A is H, hydroxy, -CH2OH, -CH (OH) CH3, -C (O) -OCH3, -C (OH) (CH3) 2, -O (CH2) t-COOH, -C (O) -NR6 , - (CH2) nP (= O) (OR7) (OR7) optionally substituted, - (CH2) nOP (= O) (OR7) (OR7) optionally substituted, - (CH2) n- OP (= O) (OR7 ) (R7) optionally substituted, -CH = CH-P (= O) (OR7) (OR1), C (O) NHCH3, CN, COOR6 or -R4-COOH, where R4 is linear (C1-20) alkylene or branched, linear or branched (C1-20) alkenylene, linear or branched (C1-20) alkynylene, (C3-20) cycloalkyl, or optionally substituted azetidinyl; R1 and R2 are independently selected from the group consisting of hydrogen, CF3, halogen, (C1-20) alkyl, (C1-20) alkoxy, substituted (C3-20) cycloalkyl-alkyl, substituted (C3-20) cycloalkylalkoxy, (C2-20) alkenyl, substituted (C2-20) arylalkenyl, (C2-20) alkynyl, substituted (C2-20) alkynyl, aryl, substituted (C1-20) substituted alkyl, heteroaryl (C2-) alkyl 20) substituted, substituted aryl alkoxy, substituted heteroaryl alkoxy, substituted alkyl aryl, arylalkyl, substituted aryl arylalkyl, substituted arylalkyl arylalkyl, CN and -O-indolizinyl; wherein said groups and R2 may optionally be substituted with one or more substituents that are independently selected from (C1-20) alkyl, CF3, halogen, hydroxy, (C1-20) alkoxy, OCF3, and CN; where one or more of the carbon atoms in the R1 or R2 groups can be independently replaced by oxygen not belonging to a peroxide, sulfur or NR8; where R8 is hydrogen or a (C1-20) alkyl group; where one of R1 and R2 is different from hydrogen; and where the alkyl, alkenyl, and alkynyl groups in R1 and R2 are optionally substituted with the oxo or halo groups; each R5 is independently H, optionally substituted (C1-3) alkyl, or -C (O) -O-C1-3) optionally substituted phenyl; each R6 is independently H or optionally substituted (C1-2) alkyl; each R7 is independently H, optionally substituted (C1-2) alkyl or optionally substituted phenyl; m is 1 or 2; n is 1, 2 or 3; t is 1, 2 or 3; and u is 0, 1 or 2; with the proviso that A and D must not be both H at the same time; and with the proviso that the compound should not be (2) where X is CH or N; Y is CH2, NH, N (CH3), S or O.

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