How to say finally, their friendship ended and their close relationship disappeared. in Japanese

1)ついについに(tsuini) (adv) finally/at last/in the end彼ら彼ら(karera) (n,adj-no) those/theyの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question友情友情(yuujou) (n) friendship/fellowship/camaraderieが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and壊れno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb、(、) Japanese comma二人二人(futari) (n) two persons/two people/pair/coupleの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question親密親密(shinmitsu) (adj-na,n) intimacy/friendshipな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibition関係関係(kankei) (n,vs,adj-no) relation/relationship/connection/participation/involvement/concern/influence/effect/sexual relations/sexual relationship/related to .../connected to ...は(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbえ(e) (int) eh?/eh/ strengthens a question, assertion, etc./used when calling out to someone失せno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbた(ta) (aux-v) indicate past completed or action/indicates light imperative。(。) Japanese period "."    
tsuini karera no yuujou ga koware 、 futari no shinmitsu na kankei ha kie use ta 。
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