LU86770A1 - Nouveaux derives de la purine,leur preparation et leur utilisation comme medicaments - Google Patents

Nouveaux derives de la purine,leur preparation et leur utilisation comme medicaments Download PDF

Info

Publication number: LU86770A1
Authority: LU; Luxembourg
Prior art keywords: compounds; formula; group; compound; hydroxy
Prior art date: 1986-02-14

Application number

LU86770A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1986-02-14

Filing date

1987-02-12

Publication date

1987-09-15

1987-02-12 Application filed by Sandoz Sa filed Critical Sandoz Sa

1987-09-15 Publication of LU86770A1 publication Critical patent/LU86770A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 7
239000003814 drug Substances 0.000 title claims description 5
150000003212 purines Chemical class 0.000 title description 2
229940083251 peripheral vasodilators purine derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 19
238000000034 method Methods 0.000 claims description 15
-1 1-piperidino Chemical group 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
235000010290 biphenyl Nutrition 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
125000006267 biphenyl group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000007858 starting material Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
230000003177 cardiotonic effect Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
230000003288 anthiarrhythmic effect Effects 0.000 description 4
238000001802 infusion Methods 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229930024421 Adenine Natural products 0.000 description 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
206010007556 Cardiac failure acute Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000643 adenine Drugs 0.000 description 3
239000000496 cardiotonic agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 3
210000005240 left ventricle Anatomy 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 2
229960002105 amrinone Drugs 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000004927 fusion Effects 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
MPNBXFXEMHPGTK-UHFFFAOYSA-N pyrimidine-4,5,6-triamine Chemical compound NC1=NC=NC(N)=C1N MPNBXFXEMHPGTK-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CBZGXAXPEPQPLY-IBGZPJMESA-N (2s)-3-(4-benzhydrylpiperazin-1-yl)propane-1,2-diol Chemical compound C1CN(C[C@H](O)CO)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CBZGXAXPEPQPLY-IBGZPJMESA-N 0.000 description 1
CTKINSOISVBQLD-GSVOUGTGSA-N (R)-Glycidol Chemical compound OC[C@@H]1CO1 CTKINSOISVBQLD-GSVOUGTGSA-N 0.000 description 1
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
GOILPRCCOREWQE-UHFFFAOYSA-N 6-methoxy-7h-purine Chemical compound COC1=NC=NC2=C1NC=N2 GOILPRCCOREWQE-UHFFFAOYSA-N 0.000 description 1
CKOMXBHMKXXTNW-UHFFFAOYSA-N 6-methyladenine Chemical compound CNC1=NC=NC2=C1N=CN2 CKOMXBHMKXXTNW-UHFFFAOYSA-N 0.000 description 1
LMWFSHBVFKCMHW-UHFFFAOYSA-N 8-(Trifluoromethyl)-9H-purin-6-amine Chemical compound NC1=NC=NC2=C1NC(C(F)(F)F)=N2 LMWFSHBVFKCMHW-UHFFFAOYSA-N 0.000 description 1
ORUIZIXJCCIGAI-UHFFFAOYSA-N 8-methyl-7h-purin-6-amine Chemical compound C1=NC(N)=C2NC(C)=NC2=N1 ORUIZIXJCCIGAI-UHFFFAOYSA-N 0.000 description 1
MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 1
RYFOOGGDZXMOBP-CYBMUJFWSA-N CC1=CC=C(C=C1)S(=O)(=O)O[C@@]2(COC(O2)(C)C)C Chemical compound CC1=CC=C(C=C1)S(=O)(=O)O[C@@]2(COC(O2)(C)C)C RYFOOGGDZXMOBP-CYBMUJFWSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
208000003734 Supraventricular Tachycardia Diseases 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
230000015572 biosynthetic process Effects 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
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
206010061592 cardiac fibrillation Diseases 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000013265 extended release Methods 0.000 description 1
230000002600 fibrillogenic effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000036747 functional refractory period Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
210000005246 left atrium Anatomy 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
STYFLCAHEVROJU-UHFFFAOYSA-N n,n-diethyl-7h-purin-6-amine Chemical compound CCN(CC)C1=NC=NC2=C1NC=N2 STYFLCAHEVROJU-UHFFFAOYSA-N 0.000 description 1
UITDLMKGFBJWPJ-UHFFFAOYSA-N n-(2-acetamido-7h-purin-6-yl)acetamide Chemical compound CC(=O)NC1=NC(NC(C)=O)=C2NC=NC2=N1 UITDLMKGFBJWPJ-UHFFFAOYSA-N 0.000 description 1
GSVFENCKYURWTI-UHFFFAOYSA-N n-ethyl-7h-purin-6-amine Chemical compound CCNC1=NC=NC2=C1NC=N2 GSVFENCKYURWTI-UHFFFAOYSA-N 0.000 description 1
PEBFHJTVTOEWIX-UHFFFAOYSA-N n-propan-2-yl-7h-purin-6-amine Chemical compound CC(C)NC1=NC=NC2=C1NC=N2 PEBFHJTVTOEWIX-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
238000005303 weighing Methods 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
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
- 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
- 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
- C07D473/36—Sulfur atom
- C07D473/38—Sulfur atom attached in position 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU86770A 1986-02-14 1987-02-12 Nouveaux derives de la purine,leur preparation et leur utilisation comme medicaments LU86770A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE3604743		1986-02-14
DE3604743		1986-02-14
DE3612953		1986-04-17
DE3612953		1986-04-17

Publications (1)

Publication Number	Publication Date
LU86770A1 true LU86770A1 (fr)	1987-09-15

Family

ID=25840975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86770A LU86770A1 (fr)	1986-02-14	1987-02-12	Nouveaux derives de la purine,leur preparation et leur utilisation comme medicaments

Country Status (20)

Country	Link
US (1)	US4849423A (de)
AT (1)	AT389514B (de)
AU (1)	AU590047B2 (de)
BE (1)	BE1000245A3 (de)
CA (1)	CA1285559C (de)
CH (1)	CH668973A5 (de)
DK (1)	DK71187A (de)
ES (1)	ES2004218A6 (de)
FI (1)	FI86728C (de)
FR (1)	FR2596051B1 (de)
GB (1)	GB2186573B (de)
GR (1)	GR870233B (de)
HU (1)	HU198052B (de)
IL (1)	IL81546A (de)
IT (1)	IT1216791B (de)
LU (1)	LU86770A1 (de)
NL (1)	NL8700245A (de)
NZ (1)	NZ219250A (de)
PH (1)	PH23367A (de)
SE (1)	SE468643B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5238537A (en) *	1981-09-15	1993-08-24	Dutt William H	Extended nip press belt having an interwoven base fabric and an impervious impregnant
US5234551A (en) *	1981-09-24	1993-08-10	Dutt William H	Extended nip press belt having an interwoven base fabric and an impervious impregnant
US5057517A (en) *	1987-07-20	1991-10-15	Merck & Co., Inc.	Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents
US5164390A (en) *	1988-03-03	1992-11-17	Ortho Pharmaceutical Corporation	6-substituted purinyl piperazine derivatives
US4885300A (en) *	1988-03-03	1989-12-05	Ortho Pharmaceutical Corporation	4-Substituted pyrazolo[3,4-D]pyrimidine derivatives
US5021574A (en) *	1988-03-03	1991-06-04	Ortho Pharmaceutical Corporation	6-substituted purinyl piperazine derivatives
US5215987A (en) *	1990-04-23	1993-06-01	Ortho Pharmaceutical Corporation	Substituted benzhydryl 2-hydroxypropyl piperazine derivatives
JP2651043B2 (ja) *	1990-07-10	1997-09-10	麒麟麦酒株式会社	ジフェニルメチルピペラジン誘導体
US5336769A (en) *	1992-02-17	1994-08-09	Kyowa Hakko Kogyo Co., Ltd.	Xanthine derivatives
JP5318938B2 (ja) *	2011-06-09	2013-10-16	株式会社アエタスファルマ	ジフェニルメチルピペラジン誘導体、及びそれを用いた医薬組成物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1133989A (en) *	1964-12-08	1968-11-20	Chugai Pharmaceutical Co Ltd	Theophylline derivatives, their salts and process for preparing the same
DE1620576A1 (de) *	1966-11-25	1970-02-26	Troponwerke Dinklage & Co	Verfahren zur Herstellung von Theophyllin- und Theobrominverbindungen
GB1165283A (en) *	1967-01-17	1969-09-24	Science Union & Cie	New Purine Derivatives and processes for prepararing them
DE2334009A1 (de) *	1973-07-04	1975-01-23	Boehringer Mannheim Gmbh	Purin-derivate sowie verfahren zu ihrer herstellung
DE2401254A1 (de) *	1974-01-11	1975-11-27	Boehringer Mannheim Gmbh	Neue derivate von n hoch 6-substituierten adeninen
YU96177A (en) *	1976-04-24	1982-08-31	Wuelfing Johann A	Process for obtaining adenine derivatives
US4426383A (en) *	1980-09-04	1984-01-17	Eisai Co., Ltd.	Theophylline and theobromine derivatives
EP0052964A1 (de) *	1980-11-20	1982-06-02	Beecham Group Plc	Adeninderivate mit pharmakologischer Aktivität
DE3307395A1 (de) *	1982-03-02	1983-09-08	Eisai Co., Ltd., Tokyo	Arzneimittel zur behandlung von schmerzen, fieber, gewebe- und/oder knochen- und gelenkentzuendungen mit einem gehalt an theobromin- oder theophyllinderivaten als aktivem bestandteil

1987
- 1987-02-02 HU HU87353A patent/HU198052B/hu not_active IP Right Cessation
- 1987-02-02 NL NL8700245A patent/NL8700245A/nl not_active Application Discontinuation
- 1987-02-09 FR FR878701670A patent/FR2596051B1/fr not_active Expired
- 1987-02-09 CH CH460/87A patent/CH668973A5/de not_active IP Right Cessation
- 1987-02-10 GB GB8702937A patent/GB2186573B/en not_active Expired
- 1987-02-11 US US07/013,516 patent/US4849423A/en not_active Expired - Fee Related
- 1987-02-11 GR GR870233A patent/GR870233B/el unknown
- 1987-02-12 FI FI870585A patent/FI86728C/fi not_active IP Right Cessation
- 1987-02-12 ES ES8700353A patent/ES2004218A6/es not_active Expired
- 1987-02-12 IL IL81546A patent/IL81546A/xx unknown
- 1987-02-12 DK DK071187A patent/DK71187A/da not_active Application Discontinuation
- 1987-02-12 IT IT8747635A patent/IT1216791B/it active
- 1987-02-12 CA CA000529556A patent/CA1285559C/en not_active Expired - Lifetime
- 1987-02-12 AT AT0029787A patent/AT389514B/de not_active IP Right Cessation
- 1987-02-12 SE SE8700555A patent/SE468643B/sv not_active Application Discontinuation
- 1987-02-12 NZ NZ219250A patent/NZ219250A/xx unknown
- 1987-02-12 AU AU68709/87A patent/AU590047B2/en not_active Ceased
- 1987-02-12 LU LU86770A patent/LU86770A1/fr unknown
- 1987-02-12 BE BE8700113A patent/BE1000245A3/fr not_active IP Right Cessation
- 1987-02-13 PH PH34856A patent/PH23367A/en unknown

Also Published As

Publication number	Publication date
AT389514B (de)	1989-12-27
HU198052B (en)	1989-07-28
FI86728B (fi)	1992-06-30
FR2596051B1 (fr)	1989-05-26
SE8700555D0 (sv)	1987-02-12
IL81546A (en)	1990-04-29
SE468643B (sv)	1993-02-22
GB2186573B (en)	1989-11-22
BE1000245A3 (fr)	1988-09-20
FI870585L (fi)	1987-08-15
HUT45528A (en)	1988-07-28
AU6870987A (en)	1987-08-20
PH23367A (en)	1989-07-14
GR870233B (en)	1987-06-12
GB2186573A (en)	1987-08-19
FR2596051A1 (fr)	1987-09-25
IT8747635A0 (it)	1987-02-12
DK71187A (da)	1987-08-15
AU590047B2 (en)	1989-10-26
FI86728C (fi)	1992-10-12
IL81546A0 (en)	1987-09-16
CH668973A5 (de)	1989-02-15
ATA29787A (de)	1989-05-15
GB8702937D0 (en)	1987-03-18
US4849423A (en)	1989-07-18
IT1216791B (it)	1990-03-14
DK71187D0 (da)	1987-02-12
NL8700245A (nl)	1987-09-01
NZ219250A (en)	1989-10-27
ES2004218A6 (es)	1988-12-16
CA1285559C (en)	1991-07-02
FI870585A0 (fi)	1987-02-12
SE8700555L (sv)	1987-08-15

Publication	Publication Date	Title
EP0202164B1 (de)	1989-02-08	(Benzoyl-4-piperidino)-2-phenyl-1-alkanolderivate, ihre Herstellung und ihre Verwendung als Heilmittel
CH651042A5 (fr)	1985-08-30	Derives de la theophylline et de la theobromine, procede pour leur preparation et compositions pharmaceutiques contenant ces derives.
EP0110781B1 (de)	1987-04-01	Substituierte (Amino-2-ethyl)-6-Benzoxazolinone, ihre Herstellung und pharmazeutische Zusammenstellung die sie enthält
LU86770A1 (fr)	1987-09-15	Nouveaux derives de la purine,leur preparation et leur utilisation comme medicaments
EP0037778A1 (de)	1981-10-14	2-(1,4-Benzodioxanyl)-methoxy-propanolamine, Verfahren zu deren Herstellung und Verwendung als Arzneimittel
EP0022118A1 (de)	1981-01-07	Sulfonyl-anilin-Derivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0556872A1 (de)	1993-08-25	Verwendung von 2,2-Dimethyl-chromen Derivate für die Behandlung von Asthma
FR2879598A1 (fr)	2006-06-23	Inhibiteurs de phosphatases cdc25
FR2612517A1 (fr)	1988-09-23	Derives de benzoxazine, procedes de preparation de ces derives et compositions pharmaceutiques les contenant
FR2625678A1 (fr)	1989-07-13	Agents anorexigenes a base de n-(quinuclidin-3-yl)-benzamides ou thiobenzamides
MC1357A1 (fr)	1981-08-10	Derives de 2,3-indoledione
FR2682953A1 (fr)	1993-04-30	Nouveaux derives de naphtamides, leur procede de preparation et leur application dans le domaine therapeutique.
EP0221958A1 (de)	1987-05-20	3-aminopropyloxyphenylabkömmlinge, herstellung und arzneitmittel die sie enthalten.
EP0005091B1 (de)	1981-11-25	Monosubstituierte Piperazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
EP0008259A1 (de)	1980-02-20	Piperidylbenzimidazolinon-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP0037344A1 (de)	1981-10-07	Amino-alkoxy-pyrazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
JPH02258749A (ja)	1990-10-19	ポリヒドロキシベンジルオキシプロパノールアミン
EP0275221B1 (de)	1991-04-17	N-(1H-indol-4-yl)-Benzamidderivate, ihre Salze und deren Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CA2629738A1 (fr)	2007-05-31	Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant
US3294638A (en)	1966-12-27	Method and compositions employing 2-alkyl-3-piperidinopyrazines
FR2508032A1 (fr)	1982-12-24	Nouveaux derives amino-3 aryloxymethyl-2 propanol-1, leur procede de preparation et leurs applications en therapeutique
HU186488B (en)	1985-08-28	Process for producing pyridine derivatives and pharmaceutival compositions containing them as active agents
EP1097145B1 (de)	2003-05-28	Polyhydroxyalkylpyrazine derivate und deren herstellung und diese enthaltende arzneimittel
EP0188169B1 (de)	1988-01-27	Bis-2-(4-hydroxy-2-isopropyl-5-methyl-phenoxy)-ethylamine, Verfahren zu deren Synthese und diese enthaltende pharmazeutische Zusammensetzungen
JP4204794B2 (ja)	2009-01-07	逆転写酵素阻害剤