DE2148838A1 - Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben - Google Patents
Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselbenInfo
- Publication number
- DE2148838A1 DE2148838A1 DE19712148838 DE2148838A DE2148838A1 DE 2148838 A1 DE2148838 A1 DE 2148838A1 DE 19712148838 DE19712148838 DE 19712148838 DE 2148838 A DE2148838 A DE 2148838A DE 2148838 A1 DE2148838 A1 DE 2148838A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- adenosine derivatives
- adenosine
- straight
- branched alkyl
- 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.)
- Withdrawn
Links
- 150000003835 adenosine derivatives Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 purine ribosides Chemical class 0.000 claims description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 claims description 2
- 230000003243 anti-lipolytic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 230000002058 anti-hyperglycaemic effect Effects 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000001000 lipidemic effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- YDQXFSUHMHEUDK-MIWZLHRFSA-N 1-[1,7-diacetyl-6-chloro-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,8-dihydro-2H-purin-3-yl]ethanone Chemical compound C(C)(=O)N1CN(C2N(CN(C(=C12)Cl)C(C)=O)C(C)=O)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO YDQXFSUHMHEUDK-MIWZLHRFSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 11
- 229960005305 adenosine Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000006835 Lamins Human genes 0.000 description 2
- 108010047294 Lamins Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000005053 lamin Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XHRJGHCQQPETRH-KQYNXXCUSA-N (2r,3r,4s,5r)-2-(6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(Cl)=C2N=C1 XHRJGHCQQPETRH-KQYNXXCUSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XLXBMMXDVLSNGN-UHFFFAOYSA-N 1-cyclopentyl-n-methylmethanamine Chemical compound CNCC1CCCC1 XLXBMMXDVLSNGN-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- YBPHGVBAJQGYDH-ZKCHVHJHSA-N CN[C@H]1CC[C@H](C)CC1 Chemical compound CN[C@H]1CC[C@H](C)CC1 YBPHGVBAJQGYDH-ZKCHVHJHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OZODQPLTZOYKLN-UHFFFAOYSA-N n-(2-methylpropyl)cycloheptanamine Chemical compound CC(C)CNC1CCCCCC1 OZODQPLTZOYKLN-UHFFFAOYSA-N 0.000 description 1
- ARHUUPGCYHESJV-UHFFFAOYSA-N n-(2-methylpropyl)cyclohexanamine Chemical compound CC(C)CNC1CCCCC1 ARHUUPGCYHESJV-UHFFFAOYSA-N 0.000 description 1
- QNHOLMFUDDNTDM-UHFFFAOYSA-N n-(2-methylpropyl)cyclooctanamine Chemical compound CC(C)CNC1CCCCCCC1 QNHOLMFUDDNTDM-UHFFFAOYSA-N 0.000 description 1
- KSWJKWKZMNCDJF-UHFFFAOYSA-N n-methylcyclooctanamine Chemical compound CNC1CCCCCCC1 KSWJKWKZMNCDJF-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 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
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712148838 DE2148838A1 (de) | 1971-09-30 | 1971-09-30 | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben |
| GB4381372A GB1342706A (en) | 1971-09-30 | 1972-09-21 | N-6-disubstituted adenosine derivatives and the preparation thereof |
| HUBO1394A HU163674B (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-21 | |
| ES406933A ES406933A1 (es) | 1971-09-30 | 1972-09-22 | Procedimiento para la preparacion de nuevos derivados de adenosina disustituidos en n (6). |
| DD165804A DD100717A5 (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-22 | |
| AR244242A AR193757A1 (es) | 1971-09-30 | 1972-09-22 | Un procedimiento para la obtencion de derivados de adenosina disubstituidos |
| NL7212929A NL7212929A (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-25 | |
| ZA726558A ZA726558B (en) | 1971-09-30 | 1972-09-26 | New n(6)-disubstituted adenosine derivatives and the preparation thereof |
| CH1416672A CH564562A5 (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-27 | |
| FR7234353A FR2154686B1 (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-28 | |
| AU47232/72A AU462347B2 (en) | 1971-09-30 | 1972-09-28 | New n(6)-disubstituted adenosine derivatives andthe preparation thereof |
| AT840772A AT316764B (de) | 1971-09-30 | 1972-09-29 | Verfahren zur Herstellung von neuen N(6)-disubstituierten Adenosin-Derivaten |
| CA152,966A CA965086A (en) | 1971-09-30 | 1972-09-29 | N(6)-disubstituted adenosine derivatives and process for their preparation |
| JP9854972A JPS5549593B2 (enrdf_load_stackoverflow) | 1971-09-30 | 1972-09-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712148838 DE2148838A1 (de) | 1971-09-30 | 1971-09-30 | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2148838A1 true DE2148838A1 (de) | 1973-04-05 |
Family
ID=5821069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712148838 Withdrawn DE2148838A1 (de) | 1971-09-30 | 1971-09-30 | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032583A (en) * | 1987-12-23 | 1991-07-16 | Glaxo Group Limited | 2,N-6-disubstituted adenosines and their antihypertensive methods of use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1219205A (fr) * | 1954-05-06 | 1960-05-16 | American Cyanamid Co | Procédé de préparation des ribofuranosylpurines |
-
1971
- 1971-09-30 DE DE19712148838 patent/DE2148838A1/de not_active Withdrawn
-
1972
- 1972-09-21 GB GB4381372A patent/GB1342706A/en not_active Expired
- 1972-09-21 HU HUBO1394A patent/HU163674B/hu unknown
- 1972-09-22 DD DD165804A patent/DD100717A5/xx unknown
- 1972-09-22 AR AR244242A patent/AR193757A1/es active
- 1972-09-22 ES ES406933A patent/ES406933A1/es not_active Expired
- 1972-09-25 NL NL7212929A patent/NL7212929A/xx not_active Application Discontinuation
- 1972-09-26 ZA ZA726558A patent/ZA726558B/xx unknown
- 1972-09-27 CH CH1416672A patent/CH564562A5/xx not_active IP Right Cessation
- 1972-09-28 FR FR7234353A patent/FR2154686B1/fr not_active Expired
- 1972-09-28 AU AU47232/72A patent/AU462347B2/en not_active Expired
- 1972-09-29 CA CA152,966A patent/CA965086A/en not_active Expired
- 1972-09-29 AT AT840772A patent/AT316764B/de not_active IP Right Cessation
- 1972-09-30 JP JP9854972A patent/JPS5549593B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032583A (en) * | 1987-12-23 | 1991-07-16 | Glaxo Group Limited | 2,N-6-disubstituted adenosines and their antihypertensive methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4723272A (en) | 1974-04-04 |
| JPS5549593B2 (enrdf_load_stackoverflow) | 1980-12-12 |
| ES406933A1 (es) | 1975-10-01 |
| HU163674B (enrdf_load_stackoverflow) | 1973-10-27 |
| DD100717A5 (enrdf_load_stackoverflow) | 1973-10-05 |
| AU462347B2 (en) | 1975-06-19 |
| FR2154686A1 (enrdf_load_stackoverflow) | 1973-05-11 |
| NL7212929A (enrdf_load_stackoverflow) | 1973-04-03 |
| AT316764B (de) | 1974-07-25 |
| GB1342706A (en) | 1974-01-03 |
| AR193757A1 (es) | 1973-05-22 |
| FR2154686B1 (enrdf_load_stackoverflow) | 1975-10-31 |
| CA965086A (en) | 1975-03-25 |
| ZA726558B (en) | 1973-07-25 |
| CH564562A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| JPS4861496A (enrdf_load_stackoverflow) | 1973-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2539963C2 (de) | Purinverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten | |
| DE2407115C3 (de) | 2,6-Dimethyl-l,4-dihydropyridin-3carbonsäureamino-alkylesterderivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE2918261C2 (enrdf_load_stackoverflow) | ||
| DE69216221T2 (de) | Verbindungen mit guanidin-struktur und diese enthaltende pharmazeutische zusammensetzungen | |
| DE2136624A1 (de) | N (6)-substituierte adenosin-derivate und verfahren zur herstellung derselben | |
| DE69104948T2 (de) | Spiro[4,5]decanderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen. | |
| DE2653257C2 (enrdf_load_stackoverflow) | ||
| DE69031989T2 (de) | Selektive Adenosinrezeptor-Liganden | |
| WO2002066429A1 (de) | Verfahren zur herstellung von nicht hydratisiertem fexofenadin-hydrochlorid und eine so erhaetliche neue kristalline form | |
| DE2253750C3 (de) | Apovincaminsaure-alkylester, Verfahren zu ihrer Herstellung und pharmazeutische | |
| DE2528609C3 (de) | Desoxyvincaminsäureamide, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2148838A1 (de) | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben | |
| EP0553385B1 (de) | Salicyloyl-carnitin und Verfahren zu seiner Herstellung | |
| DE2930608A1 (de) | Alkylthiophenoxyalkylamine, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| DE2157036A1 (de) | Neue heterocyclisch substituierte nebularin-derivate und verfahren zu deren herstellung | |
| EP0044927B1 (de) | Durch Purinbasen substituierte Alkylamino-desoxy-1.4;3.6-dianhydro-hexit-nitrate, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung | |
| DE2426682A1 (de) | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben | |
| DE2244328A1 (de) | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben | |
| DE2521104B2 (de) | 4-Aryl-aminoalkyl-4-thiazolin-2-one, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen | |
| CH629806A5 (en) | Process for the preparation of substituted purines | |
| DE2059922A1 (de) | Neue N(6)-Aralkyl-adenosin-Derivate und Verfahren zur Herstellung derselben | |
| DE2238923A1 (de) | Acylierte n(6)-aralkyl-adenosinderivate und verfahren zur herstellung derselben | |
| DE2338963A1 (de) | Neue n(6)-disubstituierte adenosinderivate und verfahren zur herstellung derselben | |
| DE2601755C2 (de) | Pseudoisocytidin und dessen Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2612506C2 (de) | 4-Hydroxy-α-[(3,4-methylendioxyphenyl)-isopropylaminomethyl]-3-(methylsulfonylmethyl)-benzylalkohole, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |