SK11572002A3 - Nukleozidové analógy s bicyklickou bázou modifikovanou karboxamidínom - Google Patents

Nukleozidové analógy s bicyklickou bázou modifikovanou karboxamidínom Download PDF

Info

Publication number: SK11572002A3
Authority: SK; Slovakia
Prior art keywords: cells; type; cytokine; icn; compounds
Prior art date: 2000-02-15

Application number

SK1157-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Robert Tam

Guangyi Wang

Zhi Hong

Johnson Lau

Original Assignee

Ribapharm Inc.

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.)

2000-02-15

Filing date

2001-02-15

Publication date

2003-02-04

2001-02-15 Application filed by Ribapharm Inc. filed Critical Ribapharm Inc.

2003-02-04 Publication of SK11572002A3 publication Critical patent/SK11572002A3/sk

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SK1157-2002A 2000-02-15 2001-02-15 Nukleozidové analógy s bicyklickou bázou modifikovanou karboxamidínom SK11572002A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US18267600P	2000-02-15	2000-02-15
US09/595,365 US6455508B1 (en)	2000-02-15	2000-10-05	Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides
PCT/US2001/005172 WO2001060381A1 (fr)	2000-02-15	2001-02-15	Analogues de nucleoside a base bicyclique modifiee par carboxamidine

Publications (1)

Publication Number	Publication Date
SK11572002A3 true SK11572002A3 (sk)	2003-02-04

Family

ID=26878297

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SK1149-2002A SK287765B6 (sk)	2000-02-15	2001-02-15	Použitie karboxamidínu na výrobu liečiva na liečenie vírusovej infekčnej hepatitídy C alebo B
SK1157-2002A SK11572002A3 (sk)	2000-02-15	2001-02-15	Nukleozidové analógy s bicyklickou bázou modifikovanou karboxamidínom

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
SK1149-2002A SK287765B6 (sk)	2000-02-15	2001-02-15	Použitie karboxamidínu na výrobu liečiva na liečenie vírusovej infekčnej hepatitídy C alebo B

Country Status (28)

Country	Link
US (1)	US6455508B1 (fr)
EP (3)	EP1813278B9 (fr)
JP (3)	JP4975930B2 (fr)
KR (2)	KR100811927B1 (fr)
CN (2)	CN1268335C (fr)
AT (1)	ATE377422T1 (fr)
AU (2)	AU783142B2 (fr)
BR (2)	BR0108401A (fr)
CA (2)	CA2395854A1 (fr)
CY (1)	CY1107103T1 (fr)
CZ (2)	CZ302327B6 (fr)
DE (1)	DE60131250T8 (fr)
DK (1)	DK1257281T3 (fr)
ES (2)	ES2295148T3 (fr)
HR (2)	HRP20020583A2 (fr)
HU (2)	HU229480B1 (fr)
IL (3)	IL150555A0 (fr)
MX (2)	MXPA02007932A (fr)
NO (2)	NO329927B1 (fr)
NZ (2)	NZ521390A (fr)
PL (2)	PL365239A1 (fr)
PT (1)	PT1257281E (fr)
RS (1)	RS20090086A (fr)
RU (2)	RU2259831C2 (fr)
SI (2)	SI21077A (fr)
SK (2)	SK287765B6 (fr)
WO (2)	WO2001060379A1 (fr)
YU (1)	YU61502A (fr)

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6831069B2 (en) *	1999-08-27	2004-12-14	Ribapharm Inc.	Pyrrolo[2,3-d]pyrimidine nucleoside analogs
US7638496B2 (en) *	2000-02-15	2009-12-29	Valeant Pharmaceuticals North America	Nucleoside analogs with carboxamidine modified monocyclic base
US7056895B2 (en) *	2000-02-15	2006-06-06	Valeant Pharmaceuticals International	Tirazole nucleoside analogs and methods for using same
MY164523A (en)	2000-05-23	2017-12-29	Univ Degli Studi Cagliari	Methods and compositions for treating hepatitis c virus
KR20080021797A (ko)	2000-05-26	2008-03-07	이데닉스(케이만)리미티드	플라비바이러스 및 페스티바이러스의 치료방법 및 조성물
WO2002057425A2 (fr)	2001-01-22	2002-07-25	Merck & Co., Inc.	Derives de nucleoside comme inhibiteurs de l'arn polymerase virale arn-dependante
WO2003037908A1 (fr) *	2001-10-31	2003-05-08	Ribapharm Inc.	Therapie de combinaison antivirale et compositions
NZ537662A (en)	2002-06-28	2007-10-26	Idenix Cayman Ltd	2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
PL374781A1 (en)	2002-06-28	2005-10-31	Idenix (Cayman) Limited	2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7608600B2 (en)	2002-06-28	2009-10-27	Idenix Pharmaceuticals, Inc.	Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
HUE033832T2 (en)	2002-11-15	2018-01-29	Idenix Pharmaceuticals Llc	2'-methyl nucleosides in combination with interferon and Flaviviridae mutation
RU2005121904A (ru)	2002-12-12	2006-01-20	Айденикс (Кайман) Лимитед (Ky)	Способ получения 2`-разветвленных нуклеозидов
RU2005133093A (ru) *	2003-03-28	2006-07-27	Фармассет, Инк. (Us)	Соединения для лечения флавивирусных инфекций
US20040197292A1 (en) *	2003-04-04	2004-10-07	The Procter & Gamble Company	Personal care composition containing an antidandruff component and a nonionic surfactant
US20040202636A1 (en) *	2003-04-11	2004-10-14	Kaczvinsky Joseph Robert	Personal care composition containing an antidandruff component and a nonionic surfactant
US20040197287A1 (en) *	2003-04-04	2004-10-07	The Procter & Gamble Company	Personal care composition containing an antidandruff component and a nonionic surfactant
US6930093B2 (en) *	2003-07-10	2005-08-16	Valeant Research & Development	Use of ribofuranose derivatives against inflammatory bowel diseases
US20050009848A1 (en) *	2003-07-10	2005-01-13	Icn Pharmaceuticals Switzerland Ltd.	Use of antivirals against inflammatory bowel diseases
WO2005018330A1 (fr) *	2003-08-18	2005-03-03	Pharmasset, Inc.	Regime de dosage pour therapie contre flaviviridae
US20050095218A1 (en) *	2003-10-29	2005-05-05	The Procter & Gamble Company	Personal care composition containing a detersive surfactant, an antidandruff component, and ketoamide surfactants
US20050182252A1 (en)	2004-02-13	2005-08-18	Reddy K. R.	Novel 2'-C-methyl nucleoside derivatives
AU2005254057B2 (en)	2004-06-15	2011-02-17	Isis Pharmaceuticals, Inc.	C-purine nucleoside analogs as inhibitors of RNA-dependent RNA viral polymerase
JP4516863B2 (ja) *	2005-03-11	2010-08-04	株式会社ケンウッド	音声合成装置、音声合成方法及びプログラム
CA2606195C (fr)	2005-05-02	2015-03-31	Merck And Co., Inc.	Inhibiteurs de la protease ns3 du vhc
AR057456A1 (es)	2005-07-20	2007-12-05	Merck & Co Inc	Inhibidores de la proteasa ns3 del vhc
NZ565269A (en)	2005-08-01	2010-03-26	Merck & Co Inc	Macrocyclic peptides as HCV NS3 protease inhibitors
EP1976382B1 (fr)	2005-12-23	2013-04-24	IDENIX Pharmaceuticals, Inc.	Procede pour la preparation d'un intermediaire synthetique pour la preparation de nucleosides ramifies
US8497292B2 (en)	2005-12-28	2013-07-30	Translational Therapeutics, Inc.	Translational dysfunction based therapeutics
WO2007123579A2 (fr) *	2005-12-28	2007-11-01	Translational Therapeutics	Thérapeutique reposant sur une perturbation de traduction
GB0609492D0 (en)	2006-05-15	2006-06-21	Angeletti P Ist Richerche Bio	Therapeutic agents
GB0612423D0 (en)	2006-06-23	2006-08-02	Angeletti P Ist Richerche Bio	Therapeutic agents
WO2008005542A2 (fr) *	2006-07-07	2008-01-10	Gilead Sciences, Inc.,	Composés antiviraux à base de phosphinate
AU2007309488B2 (en)	2006-10-24	2012-10-11	Merck Sharp & Dohme Corp.	HCV NS3 protease inhibitors
CA2667146C (fr)	2006-10-24	2016-01-19	Merck & Co., Inc.	Inhibiteurs de la protease ns3 du vhc
AU2007309546A1 (en)	2006-10-24	2008-05-02	Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A.	HCV NS3 protease inhibitors
BRPI0718161A2 (pt)	2006-10-27	2013-11-26	Merck & Co Inc	Composto, composição farmacêutica, e, uso do composto.
US8377874B2 (en)	2006-10-27	2013-02-19	Merck Sharp & Dohme Corp.	HCV NS3 protease inhibitors
GB0625345D0 (en)	2006-12-20	2007-01-31	Angeletti P Ist Richerche Bio	Therapeutic compounds
CA2672250C (fr)	2006-12-20	2013-04-30	Ian Stansfield	Indoles antiviraux
GB0625349D0 (en)	2006-12-20	2007-01-31	Angeletti P Ist Richerche Bio	Therapeutic compounds
JP2010533699A (ja)	2007-07-17	2010-10-28	イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー	Ｃ型肝炎感染症の治療のための大環状インドール誘導体
AU2008277377B2 (en)	2007-07-19	2013-08-01	Msd Italia S.R.L.	Macrocyclic compounds as antiviral agents
WO2009134624A1 (fr)	2008-04-28	2009-11-05	Merck & Co., Inc.	Inhibiteurs de la protéase hcv ns3
EA019327B1 (ru)	2008-07-22	2014-02-28	Мерк Шарп Энд Домэ Корп.	Макроциклическое хиноксалиновое соединение в качестве ингибитора протеазы вгс ns3
WO2010082050A1 (fr)	2009-01-16	2010-07-22	Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A.	Composés benzoxazocines substitués 7-aminoalkyle macrocycycliques destinés au traitement des infections par hépatite c
GB0900914D0 (en)	2009-01-20	2009-03-04	Angeletti P Ist Richerche Bio	Antiviral agents
US8828930B2 (en)	2009-07-30	2014-09-09	Merck Sharp & Dohme Corp.	Hepatitis C virus NS3 protease inhibitors
EP2780026B1 (fr)	2011-11-15	2019-10-23	Merck Sharp & Dohme Corp.	Inhibiteurs de la protéase ns3 du vhc
WO2013106344A1 (fr)	2012-01-12	2013-07-18	Ligand Pharmaceuticals, Inc.	Nucléosides 2'-c-méthyl comprenant un diester de phosphate cyclique de 1,3-propanediol (2-oxo-[1,3,2]-dioxaphosphorinane à la position 5'
CN102978264B (zh) *	2012-11-14	2014-12-10	广东肇庆星湖生物科技股份有限公司	一种他立韦林的制备方法
WO2014121418A1 (fr)	2013-02-07	2014-08-14	Merck Sharp & Dohme Corp.	Composés hétérocycliques tétracycliques et leurs méthodes d'utilisation pour le traitement de l'hépatite c
WO2014121417A1 (fr)	2013-02-07	2014-08-14	Merck Sharp & Dohme Corp.	Composés hétérocycliques tétracycliques et leurs procédés d'utilisation pour le traitement de l'hépatite c
JP2017512183A (ja)	2014-02-13	2017-05-18	リガンド・ファーマシューティカルズ・インコーポレイテッド	プロドラッグ化合物およびそれらの使用
CN106687118A (zh)	2014-07-02	2017-05-17	配体药物公司	前药化合物及其用途
EA201890454A1 (ru) *	2015-08-06	2018-07-31	Чимерикс, Инк.	Пирролопиримидиновые нуклеозиды и их аналоги, которые можно использовать в качестве противовирусных средств
WO2019060692A1 (fr)	2017-09-21	2019-03-28	Chimerix, Inc.	Formes morphiques de 4-amino-7-(3,4-dihydroxy-5-(hydroxyméthyle)tétrahydrofurane-2-yl)-2-méthyle-7 h-pyrrolo[2,3-d]pyrimidine-5-carboxamide et leurs utilisations
RU2020126177A (ru)	2018-01-09	2022-02-10	Лиганд Фармасьютикалз, Инк.	Ацетальные соединения и их терапевтическое применение

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3984396A (en)	1971-06-01	1976-10-05	Icn Pharmaceuticals, Inc.	1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters
US3798209A (en)	1971-06-01	1974-03-19	Icn Pharmaceuticals	1,2,4-triazole nucleosides
US3991078A (en)	1971-06-01	1976-11-09	Icn Pharmaceuticals, Inc.	N-substituted 1,2,4-triazoles
USRE29835E (en)	1971-06-01	1978-11-14	Icn Pharmaceuticals	1,2,4-Triazole nucleosides
US3962211A (en) *	1975-01-13	1976-06-08	The University Of Utah	7-substituted nucleoside compounds
US4093624A (en)	1977-01-31	1978-06-06	Icn Pharmaceuticals, Inc.	1,2,4-Thiadiazolidine-3,5-dione
SU1124559A1 (ru) *	1983-06-08	1986-07-07	Институт молекулярной биологии АН СССР	1-(2-Оксиэтоксиметил)-1,2,4-триазол-5-карбоксамид,обладающий активностью противвируса герпеса
JPS6426593A (en)	1987-07-21	1989-01-27	Asahi Glass Co Ltd	Nucleoside derivative
US4892865A (en) *	1987-12-01	1990-01-09	The Regents Of The University Of Michigan	Pyrrolo[2,3-d]pyrimidine nucleosides as antiviral agents
US5405837A (en) *	1993-05-18	1995-04-11	Indiana University Foundation	Method for the treatment of neoplastic disease utilizing tiazofurin and ribavirin
RU2186569C2 (ru) *	1996-01-23	2002-08-10	Ай-Си-Эн ФАРМАСЬЮТИКАЛЗ	Модуляция экспрессии тн1/тн2 цитокинов рибавирином и аналогами рибавирина в активированных т-лимфоцитах
US5767097A (en) *	1996-01-23	1998-06-16	Icn Pharmaceuticals, Inc.	Specific modulation of Th1/Th2 cytokine expression by ribavirin in activated T-lymphocytes
IL129126A0 (en) *	1996-10-16	2000-02-17	Icn Pharmaceuticals	Monocyclic l-nucleosides analogs and uses thereof
WO2001027114A1 (fr) *	1999-08-27	2001-04-19	Icn Pharmaceuticals, Inc.	ANALOGUES NUCLEOSIDIQUES DE PYRROLO[2,3-d]PYRIMIDINE

2000
- 2000-10-05 US US09/595,365 patent/US6455508B1/en not_active Expired - Lifetime
2001
- 2001-02-15 JP JP2001559475A patent/JP4975930B2/ja not_active Expired - Fee Related
- 2001-02-15 WO PCT/US2001/040148 patent/WO2001060379A1/fr not_active Ceased
- 2001-02-15 IL IL15055501A patent/IL150555A0/xx unknown
- 2001-02-15 JP JP2001559477A patent/JP2004510691A/ja active Pending
- 2001-02-15 NZ NZ521390A patent/NZ521390A/en unknown
- 2001-02-15 YU YU61502A patent/YU61502A/sh unknown
- 2001-02-15 AU AU47988/01A patent/AU783142B2/en not_active Ceased
- 2001-02-15 RS RSP-2009/0086A patent/RS20090086A/sr unknown
- 2001-02-15 HU HU0300027A patent/HU229480B1/hu unknown
- 2001-02-15 IL IL15099001A patent/IL150990A0/xx unknown
- 2001-02-15 BR BR0108401-1A patent/BR0108401A/pt not_active IP Right Cessation
- 2001-02-15 SI SI200120011A patent/SI21077A/sl not_active IP Right Cessation
- 2001-02-15 MX MXPA02007932A patent/MXPA02007932A/es unknown
- 2001-02-15 SK SK1149-2002A patent/SK287765B6/sk not_active IP Right Cessation
- 2001-02-15 AU AU38450/01A patent/AU3845001A/en not_active Abandoned
- 2001-02-15 EP EP07107588.1A patent/EP1813278B9/fr not_active Expired - Lifetime
- 2001-02-15 RU RU2002120922/15A patent/RU2259831C2/ru active
- 2001-02-15 PT PT01920996T patent/PT1257281E/pt unknown
- 2001-02-15 HR HR20020583A patent/HRP20020583A2/xx not_active Application Discontinuation
- 2001-02-15 ES ES01920996T patent/ES2295148T3/es not_active Expired - Lifetime
- 2001-02-15 BR BR0108402-0A patent/BR0108402A/pt not_active Application Discontinuation
- 2001-02-15 CZ CZ20022798A patent/CZ302327B6/cs not_active IP Right Cessation
- 2001-02-15 DK DK01920996T patent/DK1257281T3/da active
- 2001-02-15 MX MXPA02007931A patent/MXPA02007931A/es active IP Right Grant
- 2001-02-15 EP EP01920996A patent/EP1257281B8/fr not_active Expired - Lifetime
- 2001-02-15 HU HU0300912A patent/HUP0300912A2/hu unknown
- 2001-02-15 CZ CZ20022799A patent/CZ20022799A3/cs unknown
- 2001-02-15 KR KR1020027010417A patent/KR100811927B1/ko not_active Expired - Fee Related
- 2001-02-15 AT AT01920996T patent/ATE377422T1/de active
- 2001-02-15 EP EP01910892A patent/EP1278528A4/fr not_active Withdrawn
- 2001-02-15 KR KR1020027010593A patent/KR20030005190A/ko not_active Withdrawn
- 2001-02-15 SI SI200120010A patent/SI21076A/sl not_active IP Right Cessation
- 2001-02-15 HR HR20020657A patent/HRP20020657A2/hr not_active Application Discontinuation
- 2001-02-15 WO PCT/US2001/005172 patent/WO2001060381A1/fr not_active Ceased
- 2001-02-15 CA CA002395854A patent/CA2395854A1/fr not_active Abandoned
- 2001-02-15 RU RU2002120483/14A patent/RU2002120483A/ru not_active Application Discontinuation
- 2001-02-15 DE DE60131250T patent/DE60131250T8/de active Active
- 2001-02-15 ES ES07107588.1T patent/ES2528429T3/es not_active Expired - Lifetime
- 2001-02-15 SK SK1157-2002A patent/SK11572002A3/sk unknown
- 2001-02-15 CA CA2399208A patent/CA2399208C/fr not_active Expired - Fee Related
- 2001-02-15 NZ NZ52087701A patent/NZ520877A/xx not_active IP Right Cessation
- 2001-02-15 CN CNB018077455A patent/CN1268335C/zh not_active Expired - Fee Related
- 2001-02-15 CN CN01805036A patent/CN1420779A/zh active Pending
- 2001-02-15 PL PL01365239A patent/PL365239A1/xx unknown
- 2001-02-15 PL PL357945A patent/PL200140B1/pl unknown
2002
- 2002-07-30 IL IL150990A patent/IL150990A/en not_active IP Right Cessation
- 2002-08-14 NO NO20023855A patent/NO329927B1/no not_active IP Right Cessation
- 2002-08-14 NO NO20023852A patent/NO20023852L/no not_active Application Discontinuation
2007
- 2007-12-19 CY CY20071101614T patent/CY1107103T1/el unknown
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Also Published As

Publication number	Publication date
MXPA02007932A (es)	2004-10-15
CN1438891A (zh)	2003-08-27
IL150555A0 (en)	2003-02-12
CN1268335C (zh)	2006-08-09
ES2528429T9 (es)	2015-05-07
CA2399208A1 (fr)	2001-08-23
NO329927B1 (no)	2011-01-24
DE60131250T8 (de)	2009-01-15
KR100811927B1 (ko)	2008-03-10
SI21076A (sl)	2003-06-30
HUP0300912A2 (hu)	2003-08-28
KR20030005190A (ko)	2003-01-17
PL365239A1 (en)	2004-12-27
RU2259831C2 (ru)	2005-09-10
BR0108402A (pt)	2003-03-11
BR0108401A (pt)	2004-01-06
WO2001060381B1 (fr)	2001-11-01
NZ520877A (en)	2004-12-24
RU2002120922A (ru)	2004-01-27
HRP20020583A2 (en)	2005-10-31
HRP20020657A2 (en)	2005-10-31
IL150990A0 (en)	2003-02-12
PT1257281E (pt)	2007-12-11
KR20030032917A (ko)	2003-04-26
CZ302327B6 (cs)	2011-03-16
DE60131250D1 (de)	2007-12-20
HK1051149A1 (en)	2003-07-25
AU783142B2 (en)	2005-09-29
WO2001060379A1 (fr)	2001-08-23
NO20023852L (no)	2002-10-09
CY1107103T1 (el)	2012-10-24
RS20090086A (sr)	2010-06-30
ATE377422T1 (de)	2007-11-15
WO2001060381A1 (fr)	2001-08-23
NO20023852D0 (no)	2002-08-14
CZ20022799A3 (cs)	2003-09-17
JP2009102406A (ja)	2009-05-14
HU229480B1 (en)	2014-01-28
DE60131250T2 (de)	2008-08-28
DK1257281T3 (da)	2008-01-14
CZ20022798A3 (cs)	2003-03-12
NO20023855L (no)	2002-10-08
EP1278528A1 (fr)	2003-01-29
SI21077A (sl)	2003-06-30
AU3845001A (en)	2001-08-27
CA2399208C (fr)	2010-04-13
EP1257281A1 (fr)	2002-11-20
YU61502A (sh)	2006-03-03
HUP0300027A3 (en)	2003-09-29
SK11492002A3 (sk)	2003-02-04
AU4798801A (en)	2001-08-27
ES2528429T3 (es)	2015-02-09
EP1257281B8 (fr)	2008-01-23
CN1420779A (zh)	2003-05-28
EP1257281A4 (fr)	2003-03-19
CA2395854A1 (fr)	2001-08-23
NZ521390A (en)	2004-05-28
RU2002120483A (ru)	2004-01-27
ES2295148T3 (es)	2008-04-16
EP1278528A4 (fr)	2003-03-19
JP5253204B2 (ja)	2013-07-31
EP1813278B9 (fr)	2015-04-01
PL200140B1 (pl)	2008-12-31
NO20023855D0 (no)	2002-08-14
EP1813278A1 (fr)	2007-08-01
JP2004510691A (ja)	2004-04-08
MXPA02007931A (es)	2004-10-15
EP1813278B1 (fr)	2014-10-29
PL357945A1 (en)	2004-08-09
IL150990A (en)	2009-05-04
US6455508B1 (en)	2002-09-24
EP1257281B1 (fr)	2007-11-07
JP2004509061A (ja)	2004-03-25
SK287765B6 (sk)	2011-09-05
HUP0300027A2 (en)	2003-05-28
JP4975930B2 (ja)	2012-07-11

Publication	Publication Date	Title
SK11572002A3 (sk)	2003-02-04	Nukleozidové analógy s bicyklickou bázou modifikovanou karboxamidínom
US6831069B2 (en)	2004-12-14	Pyrrolo[2,3-d]pyrimidine nucleoside analogs
US20090176721A1 (en)	2009-07-09	Nucleoside analogs with carboxamidine modified monocyclic base
HK1051149B (en)	2008-05-02	Nucleoside analogs with carboxamidine modified monocyclic base