DE2147488A1 - Adenosinderivate und Verfahren zu ihrer Herstellung - Google Patents
Adenosinderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2147488A1 DE2147488A1 DE19712147488 DE2147488A DE2147488A1 DE 2147488 A1 DE2147488 A1 DE 2147488A1 DE 19712147488 DE19712147488 DE 19712147488 DE 2147488 A DE2147488 A DE 2147488A DE 2147488 A1 DE2147488 A1 DE 2147488A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- adenosine derivatives
- substituted
- adenosine
- 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.)
- Pending
Links
- 150000003835 adenosine derivatives Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- -1 nitrile compound Chemical class 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- RHYBPJRGJJLRQM-UBEDBUPSSA-N (2r,3r,4s,5r)-2-(6-amino-2-phenylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(C=3C=CC=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O RHYBPJRGJJLRQM-UBEDBUPSSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- VKSRAKNPXOTFAX-CNEMSGBDSA-N (2r,3r,4s,5r)-2-[6-amino-2-(4-methoxyphenyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=CC(OC)=CC=C1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 VKSRAKNPXOTFAX-CNEMSGBDSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000008223 ribosides Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- HQUFDEULYSDZNH-JXOAFFINSA-N 5-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carbonitrile Chemical compound NC1=C(C#N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HQUFDEULYSDZNH-JXOAFFINSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- DDIABTCGJITEGP-HLFSEMCJSA-N (2R,3R,4S,5R)-2-[6-amino-2-(3,4,5-trimethoxyphenyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC=1C=C(C=C(C1OC)OC)C=1N=C(C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C2N1)N DDIABTCGJITEGP-HLFSEMCJSA-N 0.000 description 1
- COQHOBWLVLQVTK-FRJWGUMJSA-N (2r,3r,4s,5r)-2-(6-amino-2-butylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(CCCC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O COQHOBWLVLQVTK-FRJWGUMJSA-N 0.000 description 1
- VFZXAVDWAOZOPF-JJNLEZRASA-N (2r,3r,4s,5r)-2-(6-amino-2-ethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(CC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O VFZXAVDWAOZOPF-JJNLEZRASA-N 0.000 description 1
- OSBQUSPVORCDCU-UHFFFAOYSA-N 3,4,5-trimethoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(OC)=C1OC OSBQUSPVORCDCU-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45084369A JPS4826038B1 (en:Method) | 1970-09-25 | 1970-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2147488A1 true DE2147488A1 (de) | 1972-03-30 |
Family
ID=13828598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712147488 Pending DE2147488A1 (de) | 1970-09-25 | 1971-09-23 | Adenosinderivate und Verfahren zu ihrer Herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3819612A (en:Method) |
| JP (1) | JPS4826038B1 (en:Method) |
| BE (1) | BE773080A (en:Method) |
| CA (1) | CA963897A (en:Method) |
| CH (1) | CH546789A (en:Method) |
| DE (1) | DE2147488A1 (en:Method) |
| DK (1) | DK126043B (en:Method) |
| FR (1) | FR2107977B1 (en:Method) |
| GB (1) | GB1367785A (en:Method) |
| HU (1) | HU163358B (en:Method) |
| NL (1) | NL7113215A (en:Method) |
| SE (1) | SE384867B (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968102A (en) * | 1974-04-18 | 1976-07-06 | Kohjin Co., Ltd. | S-substituted-2-thioadenosines |
| US4501735A (en) * | 1983-12-05 | 1985-02-26 | Warner-Lambert Company | N6-(1- and 2-benzocycloalkyl) adenosines |
| JPH0723394B2 (ja) * | 1986-11-27 | 1995-03-15 | 日本臓器製薬株式会社 | 新規アデノシン誘導体及び該化合物を有効成分として含有する医薬組成物 |
| US5459255A (en) * | 1990-01-11 | 1995-10-17 | Isis Pharmaceuticals, Inc. | N-2 substituted purines |
| US5140015A (en) * | 1990-02-20 | 1992-08-18 | Whitby Research, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| USRE36494E (en) * | 1990-02-20 | 2000-01-11 | Discovery Therapeutics, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| EP1021195A1 (en) | 1997-10-07 | 2000-07-26 | The Regents Of The University Of California | Treating occlusive peripheral vascular disease and coronary disease with combinations of heparin and an adenoside a2 agonist, or with adenosine |
| US5972903A (en) * | 1997-10-07 | 1999-10-26 | Regents Of The University Of California Corporation | Method for promoting angiogenesis using heparin and adenosine |
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| US8470801B2 (en) | 2002-07-29 | 2013-06-25 | Gilead Sciences, Inc. | Myocardial perfusion imaging methods and compositions |
| FR3125477B1 (fr) | 2021-07-23 | 2025-04-18 | Psa Automobiles Sa | Support de groupe motopropulseur à zone de déformation programmée |
-
1970
- 1970-09-25 JP JP45084369A patent/JPS4826038B1/ja active Pending
-
1971
- 1971-09-22 DK DK461771AA patent/DK126043B/da unknown
- 1971-09-23 FR FR7134278A patent/FR2107977B1/fr not_active Expired
- 1971-09-23 DE DE19712147488 patent/DE2147488A1/de active Pending
- 1971-09-23 GB GB4434171A patent/GB1367785A/en not_active Expired
- 1971-09-23 US US00183270A patent/US3819612A/en not_active Expired - Lifetime
- 1971-09-23 HU HUTA1146A patent/HU163358B/hu unknown
- 1971-09-24 SE SE7112150A patent/SE384867B/xx unknown
- 1971-09-24 BE BE773080A patent/BE773080A/xx unknown
- 1971-09-24 NL NL7113215A patent/NL7113215A/xx unknown
- 1971-09-24 CA CA123,620A patent/CA963897A/en not_active Expired
- 1971-09-24 CH CH1396071A patent/CH546789A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE773080A (fr) | 1972-01-17 |
| US3819612A (en) | 1974-06-25 |
| HU163358B (en:Method) | 1973-07-28 |
| JPS4826038B1 (en:Method) | 1973-08-03 |
| CA963897A (en) | 1975-03-04 |
| CH546789A (de) | 1974-03-15 |
| FR2107977B1 (en:Method) | 1975-03-14 |
| FR2107977A1 (en:Method) | 1972-05-12 |
| GB1367785A (en) | 1974-09-25 |
| DK126043B (da) | 1973-06-04 |
| SE384867B (sv) | 1976-05-24 |
| NL7113215A (en:Method) | 1972-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |