CA2276532C - Frangible compounds for pathogen inactivation - Google Patents
Frangible compounds for pathogen inactivation Download PDFInfo
- Publication number
- CA2276532C CA2276532C CA002276532A CA2276532A CA2276532C CA 2276532 C CA2276532 C CA 2276532C CA 002276532 A CA002276532 A CA 002276532A CA 2276532 A CA2276532 A CA 2276532A CA 2276532 C CA2276532 C CA 2276532C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- heteroalkyl
- aryl
- heteroaryl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 174
- 244000052769 pathogen Species 0.000 title claims abstract description 70
- 230000002779 inactivation Effects 0.000 title claims abstract description 18
- 230000001717 pathogenic effect Effects 0.000 title claims description 30
- 238000000034 method Methods 0.000 claims abstract description 58
- 239000012636 effector Substances 0.000 claims abstract description 53
- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 50
- 239000012620 biological material Substances 0.000 claims abstract description 48
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 48
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 48
- 230000000415 inactivating effect Effects 0.000 claims abstract description 35
- 210000003743 erythrocyte Anatomy 0.000 claims abstract description 30
- 230000007062 hydrolysis Effects 0.000 claims abstract description 27
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 27
- 230000027455 binding Effects 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000011534 incubation Methods 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 128
- -1 amino ester Chemical class 0.000 claims description 80
- 210000004369 blood Anatomy 0.000 claims description 45
- 239000008280 blood Substances 0.000 claims description 45
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 41
- 230000002441 reversible effect Effects 0.000 claims description 37
- 150000002009 diols Chemical class 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 17
- 150000007970 thio esters Chemical class 0.000 claims description 16
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical group ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 13
- 210000002381 plasma Anatomy 0.000 claims description 10
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
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- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
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- 150000007513 acids Chemical class 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 claims description 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
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- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 claims description 3
- ZHBWKWDAMIJZPW-UHFFFAOYSA-N 9-methoxyacridine Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=NC2=C1 ZHBWKWDAMIJZPW-UHFFFAOYSA-N 0.000 claims description 3
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- MLMVLVJMKDPYBM-UHFFFAOYSA-N pseudoisopsoralene Natural products C1=C2C=COC2=C2OC(=O)C=CC2=C1 MLMVLVJMKDPYBM-UHFFFAOYSA-N 0.000 claims description 3
- 210000003296 saliva Anatomy 0.000 claims description 3
- 210000000582 semen Anatomy 0.000 claims description 3
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 1
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- 125000000217 alkyl group Chemical group 0.000 description 95
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 241000282414 Homo sapiens Species 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000007832 Na2SO4 Substances 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- UKOBAUFLOGFCMV-UHFFFAOYSA-N quinacrine mustard Chemical compound C1=C(Cl)C=CC2=C(NC(C)CCCN(CCCl)CCCl)C3=CC(OC)=CC=C3N=C21 UKOBAUFLOGFCMV-UHFFFAOYSA-N 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/0005—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts
- A61L2/0082—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts using chemical substances
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M1/00—Suction or pumping devices for medical purposes; Devices for carrying-off, for treatment of, or for carrying-over, body-liquids; Drainage systems
- A61M1/02—Blood transfusion apparatus
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
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- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77988597A | 1997-01-06 | 1997-01-06 | |
| US08/779,885 | 1997-01-06 | ||
| US77983097A | 1997-01-07 | 1997-01-07 | |
| US08/779,830 | 1997-01-07 | ||
| US4369697P | 1997-04-15 | 1997-04-15 | |
| US60/043,696 | 1997-04-15 | ||
| PCT/US1998/000532 WO1998030545A1 (en) | 1997-01-06 | 1998-01-06 | Frangible compounds for pathogen inactivation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2276532A1 CA2276532A1 (en) | 1998-07-16 |
| CA2276532C true CA2276532C (en) | 2008-06-17 |
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| CN (2) | CN1248245B (enExample) |
| AT (1) | ATE243198T1 (enExample) |
| AU (1) | AU744089C (enExample) |
| CA (1) | CA2276532C (enExample) |
| DE (1) | DE69815703T2 (enExample) |
| ES (1) | ES2196530T3 (enExample) |
| WO (1) | WO1998030545A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2276532C (en) * | 1997-01-06 | 2008-06-17 | Cerus Corporation | Frangible compounds for pathogen inactivation |
| CN1203900C (zh) | 1998-01-06 | 2005-06-01 | 塞鲁斯公司 | 用于淬灭生物材料中病原体灭活剂的方法 |
| JP2002517435A (ja) | 1998-06-11 | 2002-06-18 | シーラス コーポレイション | 動脈平滑筋細胞の増殖阻害のためのアルキル化化合物の使用 |
| US7498156B2 (en) | 1998-07-21 | 2009-03-03 | Caridianbct Biotechnologies, Llc | Use of visible light at wavelengths of 500 to 550 nm to reduce the number of pathogens in blood and blood components |
| US7049110B2 (en) | 1998-07-21 | 2006-05-23 | Gambro, Inc. | Inactivation of West Nile virus and malaria using photosensitizers |
| US6403359B1 (en) | 1998-09-25 | 2002-06-11 | V. I. TECHNOLOGIES, Inc. | Solid phase quenching systems |
| US6150109A (en) | 1999-01-25 | 2000-11-21 | V. I. TECHNOLOGIES, Inc. | Lipophilic quenching of viral inactivating agents |
| US7220747B2 (en) | 1999-07-20 | 2007-05-22 | Gambro, Inc. | Method for preventing damage to or rejuvenating a cellular blood component using mitochondrial enhancer |
| US7094378B1 (en) | 2000-06-15 | 2006-08-22 | Gambro, Inc. | Method and apparatus for inactivation of biological contaminants using photosensitizers |
| US20020042043A1 (en) * | 2000-05-31 | 2002-04-11 | Adonis Stassinopoulos | Preparation of a pathogen inactivated solution of red blood cells having reduced immunogenicity |
| US9044523B2 (en) | 2000-06-15 | 2015-06-02 | Terumo Bct, Inc. | Reduction of contaminants in blood and blood products using photosensitizers and peak wavelengths of light |
| DE10051628B4 (de) * | 2000-10-18 | 2007-06-06 | Fresenius Hemocare Beteiligungs Gmbh | Einzelsträngiges Oligonukleotid und dessen Verwendung |
| CA2434256A1 (en) * | 2000-12-21 | 2003-07-31 | David Cook | Methods for inactivation of pathogens in biological materials |
| PT1592441E (pt) | 2003-02-06 | 2012-05-21 | Aduro Biotech | Listeria atenuada relativamente à entrada em células não patogénicas, vacinas compreendendo a listeria e métodos para sua utilização |
| WO2004084936A2 (en) * | 2003-02-06 | 2004-10-07 | Cerus Corporation | Modified free-living microbes, vaccine compositions and methods of use thereof |
| US7695725B2 (en) | 2003-02-06 | 2010-04-13 | Aduro Biotech | Modified free-living microbes, vaccine compositions and methods of use thereof |
| US7842289B2 (en) | 2003-12-24 | 2010-11-30 | Aduro Biotech | Recombinant nucleic acid molecules, expression cassettes, and bacteria, and methods of use thereof |
| CA2585621C (en) | 2004-10-29 | 2015-12-15 | Cerus Corporation | Improved quenching methods for red blood cell inactivation process |
| KR101896430B1 (ko) | 2008-04-09 | 2018-09-10 | 세루스 코포레이션 | 적혈구 병원체 불활성화를 위한 개선된 퀀칭 방법 |
| AU2014216178B2 (en) | 2013-02-15 | 2018-06-28 | KALA BIO, Inc. | Therapeutic compounds and uses thereof |
| US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
| EP2958895B1 (en) | 2013-02-20 | 2020-08-19 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| CA2928658A1 (en) | 2013-11-01 | 2015-05-07 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| CN104788373A (zh) * | 2015-05-06 | 2015-07-22 | 武汉大学 | 化合物s-303盐酸盐的合成方法 |
| EA201890149A1 (ru) | 2015-06-26 | 2018-07-31 | Сирус Корпорейшн | Композиции криопреципитатов и способы их получения |
| CN104991033A (zh) * | 2015-08-05 | 2015-10-21 | 上海海虹实业(集团)巢湖今辰药业有限公司 | 一种采用一测多评法测定川芎挥发油成分的方法 |
| US10799533B2 (en) | 2015-10-23 | 2020-10-13 | Cerus Corporation | Plasma compositions and methods of use thereof |
| CA3036340A1 (en) | 2016-09-08 | 2018-03-15 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| CA3036065A1 (en) | 2016-09-08 | 2018-03-15 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| AU2017382449B2 (en) | 2016-12-23 | 2024-10-24 | Cerus Corporation | Systems and methods for testing and screening using compound bound substrates |
| BR112019018273A2 (pt) | 2017-03-03 | 2020-07-14 | Cerus Corporation | kits e métodos para preparação de composições de plaquetas inativadas por patógenos |
| TWI821233B (zh) | 2017-12-29 | 2023-11-11 | 美商西勒斯股份有限公司 | 用於處理生物流體之方法、藉由該方法製備之病原體去活生物流體、及用於處理生物流體之系統 |
| CA3143213A1 (en) | 2019-06-22 | 2020-12-30 | Cerus Corporation | Biological fluid treatment systems |
| WO2020264421A1 (en) | 2019-06-28 | 2020-12-30 | Cerus Corporation | System and methods for implementing a biological fluid treatment device |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994020090A1 (en) * | 1993-03-17 | 1994-09-15 | Steritech, Inc. | Decontaminating clinical samples |
| US5691132A (en) * | 1994-11-14 | 1997-11-25 | Cerus Corporation | Method for inactivating pathogens in red cell compositions using quinacrine mustard |
| DE4444045C2 (de) * | 1994-12-10 | 1997-04-17 | Behringwerke Ag | Verfahren zur Inaktivierung von Viren mit Hilfe von Acridin oder Acridinderivaten |
| AU722811B2 (en) * | 1995-06-07 | 2000-08-10 | Cerus Corporation | Treating red blood cell solutions with anti-viral agents |
| CA2276532C (en) * | 1997-01-06 | 2008-06-17 | Cerus Corporation | Frangible compounds for pathogen inactivation |
-
1998
- 1998-01-06 CA CA002276532A patent/CA2276532C/en not_active Expired - Fee Related
- 1998-01-06 CN CN988027348A patent/CN1248245B/zh not_active Expired - Lifetime
- 1998-01-06 WO PCT/US1998/000532 patent/WO1998030545A1/en not_active Ceased
- 1998-01-06 DE DE69815703T patent/DE69815703T2/de not_active Expired - Lifetime
- 1998-01-06 ES ES98901776T patent/ES2196530T3/es not_active Expired - Lifetime
- 1998-01-06 AU AU58217/98A patent/AU744089C/en not_active Expired
- 1998-01-06 JP JP53119998A patent/JP4551502B2/ja not_active Expired - Lifetime
- 1998-01-06 CN CN2009101633119A patent/CN101676268B/zh not_active Expired - Lifetime
- 1998-01-06 EP EP98901776A patent/EP1021414B1/en not_active Expired - Lifetime
- 1998-01-06 AT AT98901776T patent/ATE243198T1/de not_active IP Right Cessation
-
2009
- 2009-12-17 JP JP2009286996A patent/JP5244083B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU744089B2 (en) | 2002-02-14 |
| JP2001508449A (ja) | 2001-06-26 |
| ATE243198T1 (de) | 2003-07-15 |
| CA2276532A1 (en) | 1998-07-16 |
| EP1021414B1 (en) | 2003-06-18 |
| ES2196530T3 (es) | 2003-12-16 |
| HK1026702A1 (en) | 2000-12-22 |
| JP5244083B2 (ja) | 2013-07-24 |
| CN101676268A (zh) | 2010-03-24 |
| WO1998030545A1 (en) | 1998-07-16 |
| JP2010095527A (ja) | 2010-04-30 |
| JP4551502B2 (ja) | 2010-09-29 |
| CN1248245B (zh) | 2012-07-04 |
| AU5821798A (en) | 1998-08-03 |
| DE69815703T2 (de) | 2004-06-03 |
| AU744089C (en) | 2003-07-31 |
| DE69815703D1 (de) | 2003-07-24 |
| HK1188441A1 (en) | 2014-05-02 |
| CN101676268B (zh) | 2013-09-25 |
| CN1248245A (zh) | 2000-03-22 |
| EP1021414A1 (en) | 2000-07-26 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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