CA2417064A1 - Composes de polyamine cyclique pour la cancerotherapie - Google Patents

Composes de polyamine cyclique pour la cancerotherapie Download PDF

Info

Publication number: CA2417064A1
Authority: CA; Canada
Prior art keywords: alkyl; compound; group; independently selected; formula
Prior art date: 2000-08-02
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.): Abandoned

Application number

CA002417064A

Other languages

English (en)

Inventor

Benjamin Frydman

Manfred Hesse

Armin Guggisberg

Kasim Popaj

Konstantin Drandarov

Hirak Basu

Subhra Bhattacharya

Yu Wang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zurich Universitaet Institut fuer Medizinische Virologie

CellGate Inc

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2000-08-02

Filing date

2001-08-02

Publication date

2002-02-07

2001-08-02 Application filed by Individual filed Critical Individual

2002-02-07 Publication of CA2417064A1 publication Critical patent/CA2417064A1/fr

Status Abandoned legal-status Critical Current

Links

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230000017074 necrotic cell death Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
108091008820 oncogenic transcription factors Proteins 0.000 description 1
ASCIWXOCZAWSON-RNJDCESWSA-N orantine Chemical compound C1=CC(O)=CC=C1[C@H]1[C@H](C(=O)N2CCCNC(=O)C[C@@H]3NCCCNCCCC2)C2=CC3=CC=C2O1 ASCIWXOCZAWSON-RNJDCESWSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000004783 oxidative metabolism Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000036284 oxygen consumption Effects 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000004108 pentose phosphate pathway Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229930015704 phenylpropanoid Natural products 0.000 description 1
150000002995 phenylpropanoid derivatives Chemical class 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
238000000053 physical method Methods 0.000 description 1
235000017807 phytochemicals Nutrition 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000000419 plant extract Substances 0.000 description 1
229930000223 plant secondary metabolite Natural products 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229930001122 polyamine alkaloid Natural products 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010188 recombinant method Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
231100000916 relative toxicity Toxicity 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000004400 serine Nutrition 0.000 description 1
JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000004426 substituted alkynyl group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000002278 tabletting lubricant Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
DODDBCGMRAFLEB-UHFFFAOYSA-N thermospermine Chemical compound NCCCCNCCCNCCCN DODDBCGMRAFLEB-UHFFFAOYSA-N 0.000 description 1
ZAXCZCOUDLENMH-UHFFFAOYSA-N thermospermine Natural products NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
235000008521 threonine Nutrition 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000032258 transport Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JGOJQVLHSPGMOC-UHFFFAOYSA-N triethyl stiborite Chemical compound [Sb+3].CC[O-].CC[O-].CC[O-] JGOJQVLHSPGMOC-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
230000005751 tumor progression Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
- C07D255/02—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002417064A 2000-08-02 2001-08-02 Composes de polyamine cyclique pour la cancerotherapie Abandoned CA2417064A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US22252200P	2000-08-02	2000-08-02
US60/222,522		2000-08-02
PCT/US2001/024282 WO2002010142A1 (fr)	2000-08-02	2001-08-02	Composes de polyamine cyclique pour la cancerotherapie

Publications (1)

Publication Number	Publication Date
CA2417064A1 true CA2417064A1 (fr)	2002-02-07

Family

ID=22832553

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002417064A Abandoned CA2417064A1 (fr)	2000-08-02	2001-08-02	Composes de polyamine cyclique pour la cancerotherapie

Country Status (7)

Country	Link
EP (1)	EP1305299A1 (fr)
JP (1)	JP2004505112A (fr)
AU (2)	AU2001278143B2 (fr)
CA (1)	CA2417064A1 (fr)
IL (1)	IL153864A0 (fr)
MX (1)	MXPA03000905A (fr)
WO (1)	WO2002010142A1 (fr)

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US10626147B2 (en)	2014-05-21	2020-04-21	Entrada Therapeutics, Inc.	Cell penetrating peptides and methods of making and using thereof
US10815276B2 (en)	2014-05-21	2020-10-27	Entrada Therapeutics, Inc.	Cell penetrating peptides and methods of making and using thereof
US11168310B2 (en)	2018-02-22	2021-11-09	Entrada Therapeutics, Inc.	Compositions and methods for treating mitochondrial neurogastrointestinal encephalopathy
US11576946B2 (en)	2018-01-29	2023-02-14	Ohio State Innovation Foundation	Peptidyl inhibitors of calcineurin-NFAT interaction
US11987647B2 (en)	2018-05-09	2024-05-21	Ohio State Innovation Foundation	Cyclic cell-penetrating peptides with one or more hydrophobic residues

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JP2005533820A (ja) *	2002-06-26	2005-11-10	セルゲイト，インコーポレイテッド	癌治療のためのポルフィリン−ポリアミン結合体
BRPI0614805A2 (pt)	2005-08-10	2011-04-12	Univ Johns Hopkins	poliaminas úteis como produtos terapêuticos antiparasìticos e anticáncer e como inibidores de demetilase lisina-especìficos
US9822364B2 (en)	2008-03-11	2017-11-21	Yale University	Compositions and methods for controlled delivery of inhibitory ribonucleic acids
WO2009114614A2 (fr)	2008-03-11	2009-09-17	Yale University	Compositions et procédés pour une administration contrôlée d'acides ribonucléiques inhibiteurs
US10465042B2 (en)	2011-12-02	2019-11-05	Yale University	Poly(amine-co-ester) nanoparticles and methods of use thereof
WO2013082529A1 (fr)	2011-12-02	2013-06-06	Yale University	Synthèse enzymatique de poly(amine-co-esters) et ses méthodes d'utilisation pour une libération de gènes
US9895451B2 (en)	2011-12-02	2018-02-20	Yale University	Formulations for targeted release of agents to low pH tissue environments or cellular compartments and methods of use thereof
ES2899730T3 (es)	2012-03-07	2022-03-14	Mclean Hospital Corp	Derivados de la aminoquinolina y sus usos
GB2517375A (en) *	2012-05-15	2015-02-18	Thermo Electron Scient Instr	Ultra broadband multilayer dielectric beamsplitter coating
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US11918695B2 (en)	2014-05-09	2024-03-05	Yale University	Topical formulation of hyperbranched polymer-coated particles
WO2016081621A1 (fr)	2014-11-18	2016-05-26	Yale University	Formulations à libération ciblée d'agents sous des conditions de ph bas, et procédés d'utilisation de celles-ci
US10682422B2 (en)	2014-11-18	2020-06-16	Yale University	Formulations for targeted release of agents under low pH conditions and methods of use thereof
EP3416976A2 (fr)	2016-02-16	2018-12-26	Yale University	Compositions permettant d'améliorer l'édition ciblée de gènes et leurs procédés d'utilisation
WO2017143061A1 (fr)	2016-02-16	2017-08-24	Yale University	Compositions et procédés pour le traitement de la mucoviscidose
WO2017197128A1 (fr)	2016-05-11	2017-11-16	Yale University	Nanoparticules de poly(amine-co-ester) et leurs procédés d'utilisation
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US20210189431A1 (en)	2018-08-10	2021-06-24	Yale University	Compositions and methods for embryonic gene editing in vitro
US11814464B2 (en)	2019-04-29	2023-11-14	Yale University	Poly(amine-co-ester) polymers and polyplexes with modified end groups and methods of use thereof
US20220243211A1 (en)	2019-06-21	2022-08-04	Yale University	Peptide nucleic acid compositions with modified hoogsteen binding segments and methods of use thereof
WO2020257779A1 (fr)	2019-06-21	2020-12-24	Yale University	Compositions pna à gamma-hydroxyméthyle modifiée et leurs procédés d'utilisation
US20220280656A1 (en)	2019-07-31	2022-09-08	Yale University	Compositions and methods for treating sickle cell disease
EP4168471A1 (fr)	2020-06-19	2023-04-26	Yale University	Polymères de poly(amine-co-ester) présentant des groupes terminaux modifiés et administration pulmonaire améliorée
US20220031633A1 (en)	2020-07-28	2022-02-03	Yale University	Poly(amine-co-ester) polymeric particles for selective pulmonary delivery
US20230172870A1 (en)	2021-12-08	2023-06-08	Yale University	Surface conjugation to poly(amine-co-ester) nanoparticles for targeting to cells and tissues
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2001
- 2001-08-02 CA CA002417064A patent/CA2417064A1/fr not_active Abandoned
- 2001-08-02 WO PCT/US2001/024282 patent/WO2002010142A1/fr active IP Right Grant
- 2001-08-02 AU AU2001278143A patent/AU2001278143B2/en not_active Ceased
- 2001-08-02 JP JP2002516274A patent/JP2004505112A/ja not_active Withdrawn
- 2001-08-02 IL IL15386401A patent/IL153864A0/xx unknown
- 2001-08-02 MX MXPA03000905A patent/MXPA03000905A/es not_active Application Discontinuation
- 2001-08-02 EP EP01956110A patent/EP1305299A1/fr not_active Withdrawn
- 2001-08-02 AU AU7814301A patent/AU7814301A/xx active Pending

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Also Published As

Publication number	Publication date
IL153864A0 (en)	2003-07-31
EP1305299A1 (fr)	2003-05-02
AU2001278143B2 (en)	2007-08-09
JP2004505112A (ja)	2004-02-19
MXPA03000905A (es)	2003-06-24
AU7814301A (en)	2002-02-13
WO2002010142A1 (fr)	2002-02-07

Publication	Publication Date	Title
AU2001278143B2 (en)	2007-08-09	Cyclic polyamine compounds for cancer therapy
AU2001278143A1 (en)	2002-05-09	Cyclic polyamine compounds for cancer therapy
US7453011B2 (en)	2008-11-18	Cycloalkyl substituted polyamines for cancer therapy and methods of synthesis therefor
CN111253336B (zh)	2023-11-21	治疗癌症的化合物
US9238654B2 (en)	2016-01-19	Singleton inhibitors of sumoylation enzymes and methods for their use
US20030072715A1 (en)	2003-04-17	Cyclic polyamine compounds for cancer therapy
CN105358531B (zh)	2017-11-14	线粒体醛脱氢酶‑2调节剂和其使用方法
US20040133013A1 (en)	2004-07-08	Novel polyamine analog-amino acid conjugates useful as anticancer agents
JP7368637B2 (ja)	2023-10-24	線維芽細胞活性化タンパク質を阻害するための化合物
US5344846A (en)	1994-09-06	Compositions and methods for inhibiting deoxyhypusine synthase and the growth of cells
CN100582084C (zh)	2010-01-20	疏水性多胺类似物及其使用方法
Peng et al.	2006	Synthesis and evaluation of potent, highly-selective, 3-aryl-piperazinone inhibitors of protein geranylgeranyltransferase-I
AU3482900A (en)	2000-08-25	Antizyme modulators and their use
CA2490298A1 (fr)	2004-01-08	Conjugue de porphyrine-polyamine pour la cancerotherapie
WO2022177002A1 (fr)	2022-08-25	Sonde pour thérapie de capture de neutrons par le bore (bnct)
CN115894439B (zh)	2024-12-17	一种靶向降解gpx4的protac嵌合体及其制备方法和应用
US8404863B2 (en)	2013-03-26	Tetrahydroindoles having sphingosine-1-phosphate receptor activity
EP0072762B1 (fr)	1985-09-11	Dérivés fluorés de diaminoalkène
WO2008112251A1 (fr)	2008-09-18	Analogues de polyamine contenant des groupes cyclopropyle comme thérapies de la maladie
US9969858B2 (en)	2018-05-15	Metalloinsertor conjugates
WO2014160034A1 (fr)	2014-10-02	Modulateurs d'aldéhyde déshydrogénase-1 et leurs procédés d'utilisation
KR0154346B1 (ko)	1998-12-01	슈퍼옥사이드의 불균환 촉매로서 효과적인 질소를 포함하는 마크로사이클릭 리간드의 망간 착물
CN116813620A (zh)	2023-09-29	一种基于hsp90蛋白靶向降解gpx4的嵌合体及制备方法和应用
Cao et al.	2003	Preparation of labeled bis‐amino acid Hydroxyethylamino sulfonamide hiv protease inhibitors
GB2104060A (en)	1983-03-02	Fluorinated hexene diamine derivatives

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Date	Code	Title	Description
2006-06-27	EEER	Examination request
2009-08-03	FZDE	Discontinued