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( 12 ) United States Patent US010328157B2 (12 ) United States Patent ( 10 ) Patent No. : US 10 , 328 , 157 B2 Zhao ( 45 ) Date of Patent: Jun . 25, 2019 ( 54 ) ACETYLENEDICARBOXYL LINKERS AND 45/ 06 ( 2013. 01 ) ; A61K 47/ 6809 (2017 . 08 ) ; THEIR USES IN SPECIFIC CONJUGATION A61K 47/ 6849 ( 2017 .08 ) ; A61K 47/ 6851 OF A CELL - BINDING MOLECULE ( 2017 . 08 ) ; A61K 47 /6889 ( 2017 .08 ) ; C07C 59 / 76 (2013 . 01 ) ; C07C 233 / 20 ( 2013 .01 ) ; (71 ) Applicant: SUZHOU M -CONJ BIOTECH CO . , C07C 237 /52 (2013 .01 ) ; C070 207 /46 LTD ., Suzhou (CN ) ( 2013 .01 ) ; C07D 277 / 56 (2013 .01 ) ; C07D 309/ 14 ( 2013 . 01 ) ; CO7D 403/ 14 ( 2013 .01 ) ; ( 72 ) Inventor: Robert Yongxin Zhao , Lexington , MA C07D 407 / 12 ( 2013 . 01 ) ; C07D 407/ 14 (US ) ( 2013 .01 ) ; CO7D 413 / 04 (2013 . 01 ) ; C07D ( 73 ) Assignee : HANGZHOU DAC BIOTECH CO . , 413 / 14 ( 2013 .01 ) ; C07D 417 / 12 ( 2013 . 01 ) ; LTD . , Hangzhou ( CN ) C07D 417 / 14 ( 2013 .01 ) ; C07D 493 /04 ( 2013 . 01 ) ; C07D 498 / 14 ( 2013 . 01 ) ; C07D ( * ) Notice : Subject to any disclaimer , the term of this 519 / 00 ( 2013 .01 ) ; C07K 16 / 28 ( 2013 . 01 ) ; patent is extended or adjusted under 35 CO7K 16 / 2863 ( 2013 .01 ) ; COOK 16 / 32 U . S . C . 154 ( b ) by 0 days . ( 2013 . 01 ) ; GOIN 33 /5014 (2013 .01 ) ; A61K 2039/ 505 ( 2013 .01 ); C07K 2317 /24 (2013 . 01 ) ; (21 ) Appl. No. : 15 /423 ,695 YO2A 50 /416 ( 2018 .01 ); YO2A 50 / 466 ( 22 ) Filed : Feb . 3 , 2017 ( 2018 . 01) ; YO2A 50 /473 (2018 .01 ) (58 ) Field of Classification Search (65 ) Prior Publication Data CPC .. A61K 47 /6803 US 2017 /0143845 A1 May 25 , 2017 See application file for complete search history . Related U . S . Application Data (56 ) References Cited (62 ) Division of application No . 14 / 799, 666 , filed on Jul. 15, 2015 , now Pat . No . 9 ,839 , 687 . U . S . PATENT DOCUMENTS 4 ,000 , 304 A 12 / 1976 Wu et al. (51 ) Int. Cl. 4 , 169 , 888 A 10 / 1979 Hanka et al. A61K 47 /68 ( 2017 . 01 ) 4 ,256 , 746 A 3 / 1981 Miyashita et al. CO7K 16 / 28 ( 2006 .01 ) 4 , 294 , 757 A 10 / 1981 Asai 4 , 307 , 016 A 12 / 1981 Asai et al. C07C 59 / 76 ( 2006 . 01 ) 4 ,313 , 946 A 2 / 1982 Powell et al . CO7D 417 / 14 ( 2006 . 01 ) 4 ,315 , 929 A 2 / 1982 Freedman et al. C07C 237 /52 ( 2006 . 01 ) 4 , 322 , 348 A 3 / 1982 Asai et al. A61K 39 / 395 ( 2006 . 01 ) 4 ,331 , 598 A 5 /1982 Hasegawa et al . A61K 45 / 06 ( 2006 .01 ) C070 207 / 46 ( 2006 . 01 ) (Continued ) C07C 233 /20 ( 2006 . 01 ) FOREIGN PATENT DOCUMENTS COD 413 / 14 ( 2006 .01 ) C07D 309 / 14 ( 2006 . 01 ) CA 2 710 693 A11 /2011 C07D 403 / 14 ( 2006 .01 ) CNCA 10172396127723981 A1A 6 /2010 C07D 407 / 12 ( 2006 . 01 ) ( Continued ) C07D 407 / 14 ( 2006 .01 ) CO7D 413 /04 ( 2006 .01 ) OTHER PUBLICATIONS C07D 417 / 12 ( 2006 . 01 ) C07D 493 / 04 ( 2006 .01 ) " Chromophore” , http : // goldbook . iupac. org /plain / C01076 - plain . CO7D 498 / 14 ( 2006 .01 ) html, 1994 ( Year : 1994 ) . * CO7D 277 /56 ( 2006 .01 ) (Continued ) C07D 519 /00 ( 2006 . 01 ) A61K 31 /337 ( 2006 . 01 ) A61K 31 /404 (2006 .01 ) Primary Examiner — Noble E Jarrell A6IK 31/ 537 ( 2006 . 01 ) ( 74 ) Attorney , Agent, or Firm — Buchanan Ingersoll & A61K 31 / 5517 ( 2006 .01 ) Rooney PC GOIN 33/ 50 ( 2006 .01 ) A61K 38 /05 ( 2006 .01 ) CO7K 16 / 32 ( 2006 .01 ) (57 ) ABSTRACT A61K 39 /00 ( 2006 .01 ) (52 ) U . S . CI. Cell binding agent - drug conjugates comprising bridge link CPC . .. A61K 47 /6803 ( 2017 .08 ) ; A61K 31 /337 ers , and methods of using such linkers and conjugates are ( 2013 .01 ) ; A61K 31/ 404 ( 2013 .01 ) ; A61K provided . 31/ 537 (2013 .01 ) ; A61K 31/ 5517 ( 2013 . 01 ) ; A61K 38 /05 (2013 . 01 ) ; A61K 39 / 395 ( 2013 .01 ) ; A61K 39 /3955 ( 2013 . 01 ) ; A61K 27 Claims, 11 Drawing Sheets US 10 ,328 ,157 B2 Page 2 (56 ) References Cited 5 ,416 , 064 A 5 / 1995 Chari et al. 5 , 427 , 908 A 6 / 1995 Dower et al . U . S . PATENT DOCUMENTS 5 , 436 , 149 A 7 / 1995 Barnes 5 ,475 , 011 A 12 / 1995 Ojima et al. 4 ,341 , 761 A 7 / 1982 Ganfield et al. 5 , 475 , 092 A 12 / 1995 Chari et al . 4 , 361, 650 A 11/ 1982 Asai et al . 5 ,495 ,009 A 2 / 1996 Matteucci et al . 4 , 362 ,663 A 12 / 1982 Kida et al . 5 , 521, 284 A 5 / 1996 Pettit et al. 4 , 364 , 866 A 12 / 1982 Asai et al . 5 , 530 , 097 A 6 / 1996 Pettit et al . 4 ,371 ,533 A 2 / 1983 Akimoto et al . 5 ,530 , 101 A 6 / 1996 Queen et al. 4 ,391 , 904 A 7 / 1983 Litman et al . 5 , 545 , 806 A 8 / 1996 Lonberg et al . 4 , 399 , 121 A 8 / 1983 Albarella et al . 5 , 547 ,667 A 8 / 1996 Angelucci et al. 4 ,414 ,205 A 11/ 1983 Pettit 5 , 554 , 725 A 9 / 1996 Pettit 4 , 424 , 219 A 1 / 1984 Hashimoto et al. 5 , 569 ,825 A 10 / 1996 Lonberg et al. 4 , 427 , 587 A 1 / 1984 Kaneko et al . 5 , 571 ,698 A 11 / 1996 Ladner et al. 4 , 427 , 783 A 1 / 1984 Newman et al. 5 , 573 , 922 A 11/ 1996 Hoess et al. 4 ,444 , 887 A 4 / 1984 Hoffmann 5 ,580 ,717 A 12 / 1996 Dower et al . 4 , 450 ,254 A 5 / 1984 Isley et al. 5 , 585 , 089 A 12 / 1996 Queen et al . 4 , 451 , 570 A 5 / 1984 Royston et al. 5 , 585 , 499 A 12 / 1996 Chari et al . 4 ,464 ,467 A 8 / 1984 Hatori et al. 5 , 587 , 161 A 12 / 1996 Burke et al. 4 ,466 , 917 A 8 / 1984 Nussenzweig et al. 5 ,595 ,499 A 1 / 1997 Zander et al. 4 ,472 ,500 A 9 / 1984 Milstein et al. 5 ,599 ,902 A 2 / 1997 Pettit et al . 4 , 491, 632 A 1 / 1985 Wands et al . 5 ,606 , 017 A 2 / 1997 Willner et al . 4 ,493 , 795 A 1 / 1985 Nestor , Jr. et al. 5 ,606 , 040 A 2 / 1997 McGahren et al. 4 ,493 , 890 A 1 / 1985 Morris 5 , 622, 929 A 4 / 1997 Willner et al . 4 , 508 ,647 A 4 / 1985 Hatori et al . 5 ,625 , 126 A 4 / 1997 Lonberg et al. 4 ,663 , 453 A 5 / 1987 Glamkowski et al. 5 ,629 , 197 A 5 / 1997 Ring et al. 4 ,671 , 958 A 6 / 1987 Rodwell et al. 5 ,629 , 430 A 5 / 1997 Terashima et al. 4 ,683 , 230 A 7 / 1987 Tsunakawa et al . 5 ,633 ,425 A 5 / 1997 Lonberg et al . 4 ,723 ,003 A 2 / 1988 Glamkowski et al. 5 ,635 , 483 A 6 / 1997 Pettit et al. 4 ,723 ,007 A 2 / 1988 Glamkowski et al. 5 ,641 ,780 A 6 / 1997 Amishiro et al . 4 ,753 , 894 A 6 / 1988 Frankel et al . 5 ,660 , 829 A 8 / 1997 Burke et al . 4 ,761 , 412 A 8 / 1988 Glamkowski et al. 5 ,661 , 016 A 8 / 1997 Lonberg et al. 4 , 764 , 368 A 8 / 1988 Blattler et al . 5 ,663 , 149 A 9 / 1997 Pettit et al. 4 , 764 ,616 A 8 / 1988 Glamkowski et al. 5 ,665 , 860 A 9 / 1997 Pettit et al. 4 ,816 , 444 A 3 / 1989 Pettit et al . 5 ,686 ,237 A 11 / 1997 Al- Bayati 4 , 816 , 567 A 3 / 1989 Cabilly et al . 5 ,693 , 762 A 12 / 1997 Queen et al. 4 , 879 ,278 A 11 / 1989 Pettit et al . 5 , 703 , 080 A 12 / 1997 Nakakura et al. 4 , 912 , 227 A 3 / 1990 Kelly et al. 5 , 708 , 146 A 1 / 1998 Willner et al. 4 , 923 , 990 A 5 / 1990 Nakano et al . 5 ,712 , 374 A 1/ 1998 Kuntsmann et al. 4 , 935 , 362 A 6 / 1990 Tsunakawa et al. 5 ,714 ,586 A 2 / 1998 Kuntsmann et al. 4 , 943 ,628 A 7 / 1990 Rosen et al . 5 , 728 , 849 A 3 / 1998 Bouchard et al . 4 , 952 , 394 A 8 / 1990 Senter 5 ,739 , 116 A 4 / 1998 Hamann et al . 4 , 956 , 303 A 9 / 1990 Self 5 ,739 , 350 A 4 / 1998 Kelly et al. 4 ,970 , 198 A 11/ 1990 Lee et al . 5 , 741, 892 A 4 / 1998 Barlozzari et al. 4 ,975 ,278 A 12 / 1990 Senter et al . 5 , 767 ,236 A 6 / 1998 Kim et al. 4 , 978 ,744 A 12 / 1990 Pettit et al. 5 , 767 ,237 A 6 / 1998 Sakakibara et al . 4 , 978 , 757 A 12/ 1990 Kelly et al . 5 ,770 ,429 A 6 / 1998 Lonberg et al. 4 , 994 , 578 A 2 / 1991 Ohba et al. 5 , 770 ,701 A 6 / 1998 McGahren et al. 5 , 037 , 993 A 8 / 1991 Ohba et al. 5 , 770 ,710 A 6 /1998 McGahren et al . 5 , 053 , 394 A 10 / 1991 Ellestad et al. 5 , 773 , 001 A 6 / 1998 Hamann et al . 5 , 070 ,092 A 12/ 1991 Kanda et al . 5 , 773 , 435 A 6 / 1998 Kadow et al. 5 ,084 , 468 A 1 / 1992 Saito et al . 5 , 780 , 588 A 7 / 1998 Pettit et al . 5 , 101, 038 A 3 / 1992 Nakano et al. 5 , 786 , 377 A 7 / 1998 García et al . 5 , 106 , 951 A 4 / 1992 Morgan , Jr. et al. 5 , 786 ,486 A 7 / 1998 Fukuda et al . 5 , 108 , 912 A 4 / 1992 Lee et al. 5 , 789 ,650 A 8 / 1998 Lonberg et al . 5 , 117 ,006 A 5 / 1992 Saito et al.
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