CH615199A5 - Process for the preparation of N(6)-substituted adenosine nucleotides - Google Patents

Process for the preparation of N(6)-substituted adenosine nucleotides Download PDF

Info

Publication number: CH615199A5
Authority: CH; Switzerland
Prior art keywords: alkyl; hydrogen atom; hydroxyl groups; radical; general formula
Prior art date: 1974-08-28

Application number

CH1116875A

Other languages

German (de)

English (en)

Inventor

Helmut Dr Vorbrueggen

Original Assignee

Schering Ag

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.)

1974-08-28

Filing date

1975-08-28

Publication date

1980-01-15

1974-08-28 Priority claimed from DE2441484A external-priority patent/DE2441484A1/de

1975-08-28 Application filed by Schering Ag filed Critical Schering Ag

1980-01-15 Publication of CH615199A5 publication Critical patent/CH615199A5/de

Links

238000000034 method Methods 0.000 title claims description 10
150000003838 adenosines Chemical class 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title claims description 3
-1 hydroxy, amino Chemical group 0.000 claims description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000002841 Lewis acid Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
125000000217 alkyl group Chemical group 0.000 claims 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
125000003277 amino group Chemical group 0.000 claims 4
125000000623 heterocyclic group Chemical group 0.000 claims 4
125000003710 aryl alkyl group Chemical group 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
150000003014 phosphoric acid esters Chemical class 0.000 claims 2
150000003254 radicals Chemical class 0.000 claims 2
125000000547 substituted alkyl group Chemical group 0.000 claims 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
150000004682 monohydrates Chemical class 0.000 description 4
150000003141 primary amines Chemical class 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
239000005051 trimethylchlorosilane Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000003939 benzylamines Chemical class 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229960001149 dopamine hydrochloride Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000002773 nucleotide Substances 0.000 description 2
125000003729 nucleotide group Chemical group 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000004684 trihydrates Chemical class 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
229940097276 5-methoxytryptamine Drugs 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
AANLCWYVVNBGEE-IDIVVRGQSA-L Disodium inosinate Chemical compound [Na+].[Na+].O[C@@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 AANLCWYVVNBGEE-IDIVVRGQSA-L 0.000 description 1
GRSZFWQUAKGDAV-KQYNXXCUSA-N IMP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000005792 cardiovascular activity Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
PVBRXXAAPNGWGE-LGVAUZIVSA-L disodium 5'-guanylate Chemical compound [Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O PVBRXXAAPNGWGE-LGVAUZIVSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
239000002157 polynucleotide Substances 0.000 description 1
102000040430 polynucleotide Human genes 0.000 description 1
108091033319 polynucleotide Proteins 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 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
- C07H19/16—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)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1116875A 1974-08-28 1975-08-28 Process for the preparation of N(6)-substituted adenosine nucleotides CH615199A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2441484A DE2441484A1 (de)	1971-10-08	1974-08-28	Verfahren zur herstellung von n hoch 6-substituierten adenosin-nucleotiden

Publications (1)

Publication Number	Publication Date
CH615199A5 true CH615199A5 (en)	1980-01-15

Family

ID=5924435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1116875A CH615199A5 (en)	1974-08-28	1975-08-28	Process for the preparation of N(6)-substituted adenosine nucleotides

Country Status (6)

Country	Link
JP (1)	JPS5148699A (fr)
BE (1)	BE832855R (fr)
CH (1)	CH615199A5 (fr)
FR (1)	FR2320307A2 (fr)
GB (1)	GB1529721A (fr)
NL (1)	NL7510155A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54106056A (en) *	1978-02-08	1979-08-20	Nippon Kokan Kk <Nkk>	Equipment for blank out for steel plate
JPS6140421Y2 (fr) *	1981-01-21	1986-11-18
US4600707A (en) *	1985-01-25	1986-07-15	Warner-Lambert Company	Benzothien-3-yl adenosine; benzothien-3-yl adenosine, S-oxide; and benzothien-3-yl, S,S-dioxide adenosine compounds
US4636493A (en) *	1985-01-25	1987-01-13	Warner-Lambert Company	Benzothien-3-yl adenosine; benzothien-3-yl adenosine, S-oxide; and benzothien-3-yl, S,S-dioxide adenosine compounds

1975
- 1975-08-27 GB GB3478675A patent/GB1529721A/en not_active Expired
- 1975-08-28 BE BE159556A patent/BE832855R/fr active
- 1975-08-28 JP JP10449075A patent/JPS5148699A/ja active Pending
- 1975-08-28 CH CH1116875A patent/CH615199A5/de not_active IP Right Cessation
- 1975-08-28 FR FR7526485A patent/FR2320307A2/fr active Granted
- 1975-08-28 NL NL7510155A patent/NL7510155A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
JPS5148699A (en)	1976-04-26
FR2320307B2 (fr)	1979-01-05
FR2320307A2 (fr)	1977-03-04
NL7510155A (nl)	1976-03-02
GB1529721A (en)	1978-10-25
BE832855R (fr)	1976-03-01

Legal Events

Date	Code	Title	Description
1981-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2122991C2 (de)	1982-06-09	Verfahren zur Herstellung von Cytosin- und 6-Azacytosinnucleosiden
DE2824781C3 (de)	1980-09-18	l-Alkyl^-hydroxymethyl-SAStrihydroxy-piperidinderivate
DE202007018473U1 (de)	2008-08-07	9-Hydroxy-Risperidon (Paliperidon)
DE69925721T2 (de)	2006-03-23	Verfahren zur herstellung eines geschützten 4-aminomethyl-pyrrolidin-3-ons
US3983104A (en)	1976-09-28	N6 -substituted adenosines
CH616158A5 (fr)	1980-03-14
CH621772A5 (fr)	1981-02-27
CH615199A5 (en)	1980-01-15	Process for the preparation of N(6)-substituted adenosine nucleotides
DE68920648T2 (de)	1995-05-18	Verfahren zur Herstellung von O2,2'-anhydro-1-(beta-D-arabinofuranosyl)Thymin.
DE2151013C2 (de)	1983-04-28	Verfahren zur Herstellung von in N&uarr;6&uarr;-Stellung gegebenenfalls substituierten 6-Amino- und 2,6-Diaminopurinnucleosiden
DD246301A5 (de)	1987-06-03	Verfahren zur herstellung von 9-(2-hydroxyaethoxy-methyl)granin
EP0179408A2 (fr)	1986-04-30	Amidoalkylmélamines et aminoalkylmélamines et procédé pour leur préparation
CH696542A5 (de)	2007-07-31	Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen.
CH635340A5 (de)	1983-03-31	Verfahren zur herstellung von benzimidazolverbindungen und deren verwendung.
DE2163873A1 (de)	1973-06-20	Aminoderivate von n-heterocyclen
DE2621645C3 (de)	1981-08-06	Verfahren zur Herstellung von Aminoderivaten von N-Heterocyclen
EP0393499A1 (fr)	1990-10-24	Procédé pour la préparation de carbovir et produits intermédiaires à cet effet
EP1124805A1 (fr)	2001-08-22	Procede de production de 4-[(2',5'- diamino-6'- halopyrimidin- 4'-yl)amino]- cyclopent-2- enylmethanols
DE942149C (de)	1956-04-26	Verfahren zur Herstellung substituierter Glycinamide
DE69520554T2 (de)	2001-08-23	Verfahren zur herstellung von indolocarbazol-derivaten
DE69408128T2 (de)	1998-06-10	Wasserchathrate von piperazinylpyridin
DE1620737C3 (de)	1976-04-01	Verfahren zur Herstellung von substituierten Äthylphosphoniumsalzen
Hirota et al.	1981	Pyrimidine derivatives and related compounds. Part 37. Novel nucleophilic substitutions of 5-bromo-6-methyluracils or 5-bromo-6-bromomethyluracils with aromatic amines
DE3340773A1 (de)	1985-05-30	Verfahren zur herstellung von substituierten 2-imino-3,4,6,7-tetrahydro-4h-pyrimido(6,1-a)isochinolin-4-onen
AT254189B (de)	1967-05-10	Verfahren zur Herstellung von neuen substituierten 3-(3-Hydroxyphenyl)-1-phenacylpiperidinen