CA1317291C - Pyrines a proprietes antitumorales de type 6-sulfenamide, 6-sulfinamide et 6-sulfonamide, nucleosides et nucleotides de type purine, et composes connexes - Google Patents

Pyrines a proprietes antitumorales de type 6-sulfenamide, 6-sulfinamide et 6-sulfonamide, nucleosides et nucleotides de type purine, et composes connexes

Info

Publication number: CA1317291C
Authority: CA; Canada
Prior art keywords: compound; purine; beta; amino; ribofuranosyl
Prior art date: 1987-12-14
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

Application number

CA000585590A

Other languages

English (en)

Inventor

Naeem Botros Hanna

Ganapathi Ramakrishma Revanker

Roland Kenith Robins

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.)

Nucleic Acid Research Institute

Original Assignee

Nucleic Acid Research Institute

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.)

1987-12-14

Filing date

1988-12-12

Publication date

1993-05-04

1988-12-12 Application filed by Nucleic Acid Research Institute filed Critical Nucleic Acid Research Institute

1993-05-04 Application granted granted Critical

1993-05-04 Publication of CA1317291C publication Critical patent/CA1317291C/fr

2010-05-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 177
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150000003212 purines Chemical class 0.000 title description 10
239000002212 purine nucleoside Substances 0.000 title description 9
239000002213 purine nucleotide Substances 0.000 title description 5
150000003839 salts Chemical class 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
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NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 19
241001465754 Metazoa Species 0.000 claims description 17
229910019142 PO4 Inorganic materials 0.000 claims description 13
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
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230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000029922 reticulum cell sarcoma Diseases 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
DDYSALPDURKTBL-UHFFFAOYSA-N s-(2-amino-7h-purin-6-yl)thiohydroxylamine Chemical compound NSC1=NC(N)=NC2=C1N=CN2 DDYSALPDURKTBL-UHFFFAOYSA-N 0.000 description 1
RSHGJQIYWRWTKH-UHFFFAOYSA-N s-(7h-purin-6-yl)thiohydroxylamine Chemical compound NSC1=NC=NC2=C1NC=N2 RSHGJQIYWRWTKH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
201000000498 stomach carcinoma Diseases 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA000585590A 1987-12-14 1988-12-12 Pyrines a proprietes antitumorales de type 6-sulfenamide, 6-sulfinamide et 6-sulfonamide, nucleosides et nucleotides de type purine, et composes connexes Expired - Fee Related CA1317291C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13314387A	1987-12-14	1987-12-14
US133,143		1987-12-14

Publications (1)

Publication Number	Publication Date
CA1317291C true CA1317291C (fr)	1993-05-04

Family

ID=22457208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000585590A Expired - Fee Related CA1317291C (fr)	1987-12-14	1988-12-12	Pyrines a proprietes antitumorales de type 6-sulfenamide, 6-sulfinamide et 6-sulfonamide, nucleosides et nucleotides de type purine, et composes connexes

Country Status (3)

Country	Link
CA (1)	CA1317291C (fr)
ES (1)	ES2013379A6 (fr)
WO (1)	WO1989005817A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4908441A (en) *	1988-07-19	1990-03-13	Warner-Lambert Company	Deoxyadenosine compounds and methods of making and using the same
DE3924424A1 (de) *	1989-07-24	1991-01-31	Boehringer Mannheim Gmbh	Nucleosid-derivate, verfahren zu deren herstellung, deren verwendung als arzneimittel sowie deren verwendung bei der nucleinsaeure-sequenzierung
GB9015914D0 (en) *	1990-07-19	1990-09-05	Wellcome Found	Heterocyclic compounds
US6509320B1 (en) *	1996-10-16	2003-01-21	Icn Pharmaceuticals, Inc.	Purine L-nucleosides, analogs and uses thereof
AU9016998A (en)	1997-08-08	1999-03-01	Newbiotics, Inc.	Methods and compositions for overcoming resistance to biologic and chemotherapy
US7462605B2 (en)	1998-01-23	2008-12-09	Celmed Oncology (Usa), Inc.	Phosphoramidate compounds and methods of use
AU753155B2 (en)	1998-01-23	2002-10-10	Kiadis Pharma Intellectual Property B.V.	Enzyme catalyzed therapeutic agents
US6683061B1 (en)	1999-07-22	2004-01-27	Newbiotics, Inc.	Enzyme catalyzed therapeutic activation
BR0012676A (pt)	1999-07-22	2003-07-01	Newbiotics Inc	Métodos para tratamento de tumores resistentes a terapia
AU2019360210B2 (en) *	2018-10-17	2025-07-10	Xibin Liao	6-Mercaptopurine nucleoside analogues

1988
- 1988-12-12 CA CA000585590A patent/CA1317291C/fr not_active Expired - Fee Related
- 1988-12-13 WO PCT/US1988/004393 patent/WO1989005817A1/fr not_active Ceased
- 1988-12-13 ES ES8803792A patent/ES2013379A6/es not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES2013379A6 (es)	1990-05-01
WO1989005817A1 (fr)	1989-06-29

Legal Events

Date	Code	Title	Description
2005-05-04	MKLA	Lapsed

Publication	Publication Date	Title
US6025335A (en)	2000-02-15	L-Nucleoside Dimer Compounds and therapeutic uses
AU2012223012B2 (en)	2015-06-18	Phosphoramidate derivatives of 5 - fluoro - 2 ' - deoxyuridine for use in the treatment of cancer
EP1104436B1 (fr)	2005-12-21	Beta-l-2'-desoxy-nucleosides pour le traitement de l'hepatite b
AU2012290089B2 (en)	2016-09-29	Vitamin B6 derivatives of nucleotides, acyclonucleotides and acyclonucleoside phosphonates
CA1322748C (fr)	1993-10-05	Nucleosides anti-retrovirus d'adenosine deaminase-stable
JP2621123B2 (ja)	1997-06-18	２’‐ジデオキシ‐イソグアノシン類，イソステリック類似体およびイソグアノシン誘導体並びにそれらの使用
HU199871B (en)	1990-03-28	Process for producing deazapurine nucleoside derivatives and antiviral compositions comprising said compounds
PT94788A (pt)	1991-03-20	Processo para a preparacao de nucleosidos e necleotidos e de composicoes farma ceuticas que os contem
WO2003062255A2 (fr)	2003-07-31	Nucleosides a sucre modifie utilises en tant qu'inhibiteurs de la replication virale
SK284207B6 (en)	2004-11-03	New lipid ester of nucleoside monophosphates and their use as immunosupressive drugs
US5661136A (en)	1997-08-26	2-halo-2'-fluoro ARA adenosines as antinoplastic agents
WO2001083501A1 (fr)	2001-11-08	Analogues de nucleosides de pyrimidine antiviraux
AU5494501A (en)	2001-11-20	Anti-viral pyrimidine nucleoside analogues
EP0057548A2 (fr)	1982-08-11	Dérivés de la 7-bêta-d-arabinofuranosyl-7H-pyrrolo (2,3-d)pyrimidine 4-amine 5'-phosphate utilisables comme agents antiviraux, compositions pharmaceutiques contenant les dérivés, et procédés de préparation des composés
EP1100512A4 (fr)	2001-10-10	Elaboration de composes de thioarabinofuranosyl et leurs applications
Murakami et al.	1991	Escherichia coli mediated biosynthesis and in vitro anti-HIV activity of lipophilic 6-halo-2', 3'-dideoxypurine nucleosides
WO1989005817A1 (fr)	1989-06-29	Purines antitumorales de 6-sulfenamide, 6-sulfinamide et 6-sulfonamide, nucleosides de purine, nucleotides de purine et composes apparentes
US5041542A (en)	1991-08-20	Substituted pyrimido[5,4-d]pyrimidine nucleosides
JPH07502740A (ja)	1995-03-23	治療用ヌクレオシド
US5026836A (en)	1991-06-25	6-sulfenamide, 6-sulfinamide and 6-sulfonamide purines, purine nucleosides, purine nucleotides, pharmaceutical compositions, and processes of making
EP0788507B1 (fr)	2004-12-15	Nucleosides de l-pyranosyle
Koomen	1993	Synthesis and biological properties of selected nucleoside analogues
CN116751241A (zh)	2023-09-15	2’-去氧-2’,2’-二氟胞苷ProTide的制备及其应用
Sagi et al.	1992	Synthesis and enzymic activity of some new purine ring system analogs of adenosine 3'5'-cyclic monophosphate
EP0499291A1 (fr)	1992-08-19	Traitement de tumeurs malignes avec 8-chloroadenosine 3',5'-phosphate, cyclique 8-aminoadenosine 3',5'-phosphate cyclique et leur préparation