DD141310A5 - Verfahren zur herstellung von neuen purin-derivaten - Google Patents

Verfahren zur herstellung von neuen purin-derivaten Download PDF

Info

Publication number: DD141310A5
Authority: DD; German Democratic Republic
Prior art keywords: adenine; group; piperidino; propyl; general formula
Prior art date: 1978-02-02

Application number

DD79210689A

Other languages

German (de)

English (en)

Inventor

Walter-Gunar Friebe

Max Thiel

Androniki Roesch

Otto-Henning Wilhelms

Wolfgang Schaumann

Original Assignee

Boehringer Mannheim Gmbh

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.)

1978-02-02

Filing date

1979-01-29

Publication date

1980-04-23

1979-01-29 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1980-04-23 Publication of DD141310A5 publication Critical patent/DD141310A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 12
229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims abstract description 10
150000003212 purines Chemical class 0.000 title description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 13
230000003110 anti-inflammatory effect Effects 0.000 abstract description 6
230000003266 anti-allergic effect Effects 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical class NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
150000005018 aminopurines Chemical class 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
229960000643 adenine Drugs 0.000 description 52
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
229930024421 Adenine Natural products 0.000 description 40
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 39
-1 piperidine radical Chemical group 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000002904 solvent Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000003501 anti-edematous effect Effects 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection 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
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000000825 pharmaceutical preparation Substances 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
YURARJBSMYKJSW-UHFFFAOYSA-N 2-(6-amino-7h-purin-2-yl)ethanol Chemical compound NC1=NC(CCO)=NC2=C1NC=N2 YURARJBSMYKJSW-UHFFFAOYSA-N 0.000 description 1
DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical compound OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 description 1
USCCECGPGBGFOM-UHFFFAOYSA-N 2-propyl-7h-purin-6-amine Chemical compound CCCC1=NC(N)=C2NC=NC2=N1 USCCECGPGBGFOM-UHFFFAOYSA-N 0.000 description 1
SDAWCCIAGJBZBM-UHFFFAOYSA-N 3-ethylpurin-6-amine Chemical compound CCN1C=NC(N)=C2N=CN=C12 SDAWCCIAGJBZBM-UHFFFAOYSA-N 0.000 description 1
KFINRIKJBULSTD-UHFFFAOYSA-N 4-butylbenzamide Chemical compound CCCCC1=CC=C(C(N)=O)C=C1 KFINRIKJBULSTD-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
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 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
PIJXRNNCIJAUOX-UHFFFAOYSA-N butanoic acid;hydrochloride Chemical compound Cl.CCCC(O)=O PIJXRNNCIJAUOX-UHFFFAOYSA-N 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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
UNWBBBCIZYEGIZ-UHFFFAOYSA-N denin Natural products C1CC2(C)C3C(O)C(O)C4(C)C(C(O)C)CCC4(O)C3CCC2CC1OC(C(C1O)O)OC(C)C1OC1OC(CO)C(O)C(O)C1O UNWBBBCIZYEGIZ-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener 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
230000003760 hair shine Effects 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ITNXJLXLFAFOHO-UHFFFAOYSA-N n-piperidin-1-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NN1CCCCC1 ITNXJLXLFAFOHO-UHFFFAOYSA-N 0.000 description 1
JMQDNLCNCDSHNC-UHFFFAOYSA-N n-piperidin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CCNCC1 JMQDNLCNCDSHNC-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003870 salicylic acids Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
229940095064 tartrate Drugs 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD79210689A 1978-02-02 1979-01-29 Verfahren zur herstellung von neuen purin-derivaten DD141310A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782804416 DE2804416A1 (de)	1978-02-02	1978-02-02	Neue purin-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD141310A5 true DD141310A5 (de)	1980-04-23

Family

ID=6030974

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79210689A DD141310A5 (de)	1978-02-02	1979-01-29	Verfahren zur herstellung von neuen purin-derivaten

Country Status (16)

Country	Link
US (1)	US4212866A (da)
EP (1)	EP0003558B1 (da)
JP (1)	JPS54109999A (da)
AT (1)	AT361009B (da)
CA (1)	CA1108612A (da)
DD (1)	DD141310A5 (da)
DE (2)	DE2804416A1 (da)
DK (1)	DK143108C (da)
ES (1)	ES477420A1 (da)
FI (1)	FI790285A7 (da)
HU (1)	HU179934B (da)
IE (1)	IE47807B1 (da)
IL (1)	IL56531A (da)
PT (1)	PT69156A (da)
SU (1)	SU858568A3 (da)
ZA (1)	ZA79408B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2922159A1 (de) *	1979-05-31	1980-12-04	Boehringer Mannheim Gmbh	Neue xanthin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3529497A1 (de) *	1985-08-17	1987-02-26	Boehringer Mannheim Gmbh	N(pfeil hoch)6(pfeil hoch)-disubstituierte purinderivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
FR2699176B1 (fr) *	1992-12-11	1995-03-03	Adir	Nouveaux composés bicycliques de pyrimidine, leur procédé de préparation et les compositions pharmaceutiques les renfermant.
FR2741881B1 (fr) *	1995-12-01	1999-07-30	Centre Nat Rech Scient	Nouveaux derives de purine possedant notamment des prorietes anti-proliferatives et leurs applications biologiques
TR199902752T2 (xx)	1997-05-08	2000-06-21	Smithkline Beecham Corporation	Proteaz inhibit�rleri.
MY150958A (en) *	2005-06-16	2014-03-31	Astrazeneca Ab	Compounds for the treatment of multi-drug resistant bacterial infections

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2245061A1 (de) *	1972-09-14	1974-03-28	Boehringer Mannheim Gmbh	Derivate des adenins
DE2401254A1 (de) *	1974-01-11	1975-11-27	Boehringer Mannheim Gmbh	Neue derivate von n hoch 6-substituierten adeninen
DE2550000A1 (de) *	1975-11-07	1977-05-12	Boehringer Mannheim Gmbh	Neue purin-derivate und verfahren zu ihrer herstellung

1978
- 1978-02-02 DE DE19782804416 patent/DE2804416A1/de not_active Withdrawn
1979
- 1979-01-18 CA CA319,884A patent/CA1108612A/en not_active Expired
- 1979-01-24 US US06/006,050 patent/US4212866A/en not_active Expired - Lifetime
- 1979-01-26 SU SU792713599A patent/SU858568A3/ru active
- 1979-01-29 FI FI790285A patent/FI790285A7/fi unknown
- 1979-01-29 IL IL56531A patent/IL56531A/xx unknown
- 1979-01-29 DD DD79210689A patent/DD141310A5/de unknown
- 1979-01-29 HU HU79BO1761A patent/HU179934B/hu unknown
- 1979-01-30 PT PT7969156A patent/PT69156A/pt unknown
- 1979-01-30 JP JP881479A patent/JPS54109999A/ja active Pending
- 1979-01-31 DE DE7979100284T patent/DE2961037D1/de not_active Expired
- 1979-01-31 AT AT71379A patent/AT361009B/de not_active IP Right Cessation
- 1979-01-31 EP EP79100284A patent/EP0003558B1/de not_active Expired
- 1979-01-31 ZA ZA79408A patent/ZA79408B/xx unknown
- 1979-02-01 IE IE190/79A patent/IE47807B1/en unknown
- 1979-02-02 DK DK44379A patent/DK143108C/da not_active IP Right Cessation
- 1979-02-02 ES ES477420A patent/ES477420A1/es not_active Expired

Also Published As

Publication number	Publication date
DE2804416A1 (de)	1979-08-09
JPS54109999A (en)	1979-08-29
US4212866A (en)	1980-07-15
DK44379A (da)	1979-08-03
DE2961037D1 (en)	1981-12-24
DK143108B (da)	1981-03-30
EP0003558B1 (de)	1981-10-21
PT69156A (de)	1979-02-01
ES477420A1 (es)	1979-07-01
EP0003558A1 (de)	1979-08-22
IE47807B1 (en)	1984-06-27
IE790190L (en)	1979-08-02
IL56531A (en)	1982-05-31
FI790285A7 (fi)	1979-08-03
DK143108C (da)	1981-11-02
CA1108612A (en)	1981-09-08
HU179934B (en)	1983-01-28
ATA71379A (de)	1980-07-15
AT361009B (de)	1981-02-10
IL56531A0 (en)	1979-03-12
SU858568A3 (ru)	1981-08-23
ZA79408B (en)	1980-02-27

Publication	Publication Date	Title
EP0287907B1 (de)	1992-08-19	Pyrazolo[3,4-d]pyrimidine, Verfahren zu ihrer Herstellung und Verwendung als Arzneimittel
EP0212535B1 (de)	1991-05-29	N6-Disubstituierte Purinderivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE1445151A1 (de)	1969-01-09	Verfahren zur Herstellung chemischer Verbindungen
DE2065636A1 (de)	1974-12-19	Neue tricyclische verbindungen
DE2918261C2 (da)	1988-08-04
DE3883140T2 (de)	1994-01-13	Imidazo(2,1-b)benzothiazole und ihre Säureadditionssalze, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen.
CH665419A5 (de)	1988-05-13	1-(hydroxymethyl)-1,6,7,11b-tetrahydro-2h,4h-(1,3)-oxazino- bzw. -thiazino(4,3-a)isochinolinderivate, verfahren zu ihrer herstellung und ein arzneimittelpraeparat.
DE3125471A1 (de)	1982-03-18	"piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten"
AT334393B (de)	1977-01-10	Verfahren zur herstellung von neuen 9- (3- (4-phenylpiperazino) -propyl) -adeninen und ihren saureadditionssalzen
DD141310A5 (de)	1980-04-23	Verfahren zur herstellung von neuen purin-derivaten
EP0126296B1 (de)	1988-06-01	Substituierte Phenyl-2-(1H)-pyrimidinone, Verfahren zu ihrer Herstellung und ihre Verwendung sowie diese Verbindungen enthaltende Zubereitungen
DE2523103A1 (de)	1976-12-09	Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
CH624405A5 (da)	1981-07-31
DE2334009A1 (de)	1975-01-23	Purin-derivate sowie verfahren zu ihrer herstellung
DE2617955A1 (de)	1976-11-18	Neue l-substituierte -aroyl-4-hydroxypiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0621037A1 (de)	1994-10-26	Pyrido-pyrimidindione, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0064255A1 (de)	1982-11-10	Benzopyranylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel und Zwischenprodukte
DD219642A5 (de)	1985-03-13	Verfahren zur herstellung von bis-(piperazinyl- bzw. homopiperazinyl)alkanen
EP0021103B1 (de)	1983-05-25	Theophyllin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2342880A1 (de)	1975-01-30	Piperazin-pyrimidine, verfahren zu ihrer herstellung und ihre verwendung
DE3209271A1 (de)	1983-09-15	Bicyclische phenolether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
DE2048589A1 (de)	1971-05-06	1 Carbamoyl 4 phenylpipendme und tetrahydropyridine und Verfahren zu de ren Herstellung
DE1933599A1 (de)	1970-02-26	Chinolinderivate
DE2423725A1 (de)	1975-11-27	5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester
EP0325263B1 (de)	1992-09-23	Tetrahydropyridin-Derivate