Aroylthiourea And Arylthiocarbonylurea Derivatives

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(19) World Intellectual Property Organization International Bureau

(43) International Publication Date

(10) International Publication Number

16 December 2010 (16.12.2010)
(51) International Patent Classification: A61P 25/16 C07C 335/26 (2006.01) C07C 327/54 (2006.01) A61P 31/18 A61K 31/17 (2006.01) A61P 33/06 A61P 3/04 (2006.01) A61P 35/00 A61P 3/10 (2006.01)

W O 2010/142956 A 3
(74) Agents: NAISMITH, Robert, Stewart et al; Marks & Clerk LLP, Aurora, 120, Bothwell Street, Glasgow G2 7JS (GB).
(81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). Published:

(2006.01) (2006.01) (2006.01) (2006.01)

(21) International Application Number: PCT/GB20 10/00 1136 (22) International Filing Date:

9 June 2010 (09.06.2010)
(25) Filing Language: (26) Publication Language: (30) Priority Data: 0909912.8

English English

9 June 2009 (09.06.2009)

(71) Applicants (for all designated States except US): UNI¬ VERSITY COURT OF THE UNIVERSITY OF DUNDEE [GB/GB]; Nethergate, Perth Road, Dundee DDl 4HN (GB). UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS [GB/GB]; College Gate, North Street, St Andrews KYl 6 9AJ (GB). (72) Inventors; and (75) Inventors/ Applicants (for US only): LAIN, Sonia [GB/GB]; Erik Dahlbergsgaten 37, S-1 15 32 Stockholm (GB). WESTWOOD, Nicholas, James [GB/GB]; 4 Clayhills Grove, Dundee DD2 INF (GB). LANE, David, Philip [GB/GB]; Magicwell House, Quarry Road, BaImullo, St Andrews, Fife KYl 6 OAN (GB).

— —

with international search report (Art. 21(3)) before the expiration o the time limit for amending the f claims and to be republished in the event of receipt of amendments (Rule 48.2(h))

(88) Date of publication of the international search report: 2 7 January 20 11




(57) Abstract: The invention provides compounds according to formula (I): (wherein X , Y , Z l Rl, R2, R3, Ar and Ar' are a s dedfined herein), and physiologically acceptable salts, solvates, esters or amides thereof, pharmaceutical compositions comprising these compounds and the compounds for use in medicine, for example for the treatment or prophylaxis of diseases involving cell proliferation, such a s cancer, and for the treatment or prophylaxis of other diseases.




International application No



C07C335/26 A61P25/16

C07C327/54 A61P31 Λ 8 1

A61K31/17 A61P33/06

A61P3/04 A61P35/00


According to International Patent Classification (IPC) o r to both national classification and IPC

Minimum documentation searched (classification system followed by classification symbols)





Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched

Electronic data base consulted d u πng the international search (name of data base and where practical, search terms used)

EPO-Internal , BEILSTEIN Data, WPI Data, CHEM ABS Data

C . DOCUMENTS CONSIDERED T O BE RELEVANT Category * Citation o f document, with indication, where appropnate of the relevant passages Relevant to claim No

W O 2008/029096 A 2 (UNIVERSITY O F DUNDEE, ET AL.) 1 3 March 2008 (2008-03-13) cited in the application claims 1-9; table 1
LAIN, ET AL.: "Discovery, in vivo activity, and mechanism o f action of a small -molecule p53 activator" CANCER CELL, vol. 13, no. 5 , 6 May 2008 (2008-05-06), pages 454-463, XP002597399 CELL PRESS ISSN: 1535-6108 DOI: 10.1016/j.ccr.2008.03.004 cited in the application figure 1 ; table 1


1-4,7-9, 13-22, 24-38


Further documents are listed in the continuation of Box C

See patent family annex

Special categones o f cited documents

'A" document defining the general state o f the art which is not considered to b e of particular relevance "E" earlier document but published o n o r after the international filing date
"L" document which may throw doubts o n p πo πry cla ιm(s) o r which is cited t o establish the publication date of another citation o r other special reason (as specified)

"T" later document published after the international filing date o r priority date and not in conflict with the application but cited to understand the principle o r theory underlying the invention

"X" document o f particular relevance, the claimed invention cannot be considered novel o r cannot b e considered t o involve a n inventive step when the document is taken alone "Y" document o f particular relevance, the claimed invention cannot be considered to involve a n inventive step when the document is combined with one o r more other such docu¬ ments, such combination being obvious t o a person skilled in the art "&" document member o f the same patent family Date of mailing of the international search report

O " document refernng to a n oral disclosure, use, exhibition o r other means "P" document published prior to the international filing date but later than the priority date claimed Date o f the actual completion of the international search

1 5 November


Autho πzed officer

Name and mailing address of the ISA/ European Patent Office P B 581 8 Patentlaan 2 N L - 2280 HV Ri|Swi|k TeI (+31-70) 340-2040, Fax (+31-70) 340-3016
Form PCT/ISA/210 (second sheet) (April 2005)

Engl ish,

Russel l

International application No

C(Conti π uation).

Relevant to claim No.


Citation of document, with indication, where appropriate, of the relevant passages

ETAL.: "Isothiocyanate transpostion through a retro-ene reation: pyrolysis o f acy " thioureas" I JOURNAL O F THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1 , no. 8 , August 1979 (1979-08), pages 2001-2004, XP002597400 Royal Society of Chemistry, Cambridge, G B ISSN: 0300-922X page 2004; compounds (6b), (6c)


1-4,7-9, 13-15, 18,20,21

"p-Chlorobenzoyl isothiocyanat als Reagens zur Charakterisierung von primaren und sekundaren Aminen" FRESENIUS ZEITSCHRIFT FUR ANALYTISCHE CHEMIE, vol 165, 1959, pages 272-275, XP002597412 SPRINGER-VERLAG BERLIN, D E ISSN: 0016-1152 DOI: 10.1007/bf00459135 page 274, table, second, third and fourth compounds
ET AL.: "Synthesis in the series o f aromatic derivatives of thiourea" JOURNAL O F GENERAL CHEMISTRY O F THE USSR, vol. 26, 1956, pages 1021-1025, XP008125827 CONSULTANTS BUREAU, NEW YORK, NY, U S ISSN: 0022-1279 page 1024, lines 4-12

1-4,8,9, 13-15 , 18

1-4,7-9, 13 , 14 , 18

DATABASE CAPLUS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1958, YAO-TSO CHEN, ET AL.: "Acyl isothiocyanates. IV. p-Bromobenzoyl isothiocyanate a s a reagent for the identification of amines" XP002597446 Database accession no. 1958:113331 abstract, compound with CAS R N 101167-38-8 & HUAXUE XUEBAO, vol. 23, 1957, pages 280-285,


ISSN: 0567-7351

Form PCT/ISA/210 (continuation of second sheet) (April 2005)

International application No

Information on patent family members

Patent document cited in search report
Publication date

Patent family member(s)

Publication date

W O 2008029096




2099445 A 2 2010502582 T

16-09-2009 28-01-2010

Form PCT/ISA/210 (patent family annex) (April 2005)


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