DD151168A5 - Verfahren zur herstellung neuer xanthin-derivate - Google Patents

Verfahren zur herstellung neuer xanthin-derivate Download PDF

Info

Publication number: DD151168A5
Authority: DD; German Democratic Republic
Prior art keywords: piperidino; propyl; general formula; theophylline; group
Prior art date: 1979-05-31

Application number

DD80221417A

Other languages

German (de)

English (en)

Inventor

Walter-Gunar Friebe

Max Thiel

Wolfgang Kampe

Otto-Henning Wilhelms

Androniki Roesch

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.)

1979-05-31

Filing date

1980-05-28

Publication date

1981-10-08

1980-05-28 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-10-08 Publication of DD151168A5 publication Critical patent/DD151168A5/de

Links

LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims abstract description 9
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
-1 acyl radical Chemical group 0.000 abstract description 28
150000003254 radicals Chemical class 0.000 abstract description 10
238000011282 treatment Methods 0.000 abstract description 3
239000008194 pharmaceutical composition Substances 0.000 abstract 2
206010020751 Hypersensitivity Diseases 0.000 abstract 1
230000007815 allergy Effects 0.000 abstract 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
229960000278 theophylline Drugs 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
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 2
239000000654 additive Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 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
125000002837 carbocyclic group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 2
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 2
239000002244 precipitate Substances 0.000 description 2
150000003212 purines Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
229960004559 theobromine Drugs 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
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
OQFMNXMRKPNXOY-UHFFFAOYSA-N 1,3-dimethyl-7h-purine-2,6-dione;hydrochloride Chemical compound Cl.O=C1N(C)C(=O)N(C)C2=C1NC=N2 OQFMNXMRKPNXOY-UHFFFAOYSA-N 0.000 description 1
HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 1
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-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
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
SULSOFMXBDQJSR-UHFFFAOYSA-N 4-tert-butyl-n-[1-(3-chloropropyl)piperidin-4-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1CCN(CCCCl)CC1 SULSOFMXBDQJSR-UHFFFAOYSA-N 0.000 description 1
VGJAPABGXWFOSQ-UHFFFAOYSA-N 8-[3-(4-aminopiperidin-1-yl)propyl]-3,7-dihydropurine-2,6-dione Chemical class C1CC(N)CCN1CCCC(N1)=NC2=C1C(=O)NC(=O)N2 VGJAPABGXWFOSQ-UHFFFAOYSA-N 0.000 description 1
229930024421 Adenine Natural products 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
206010006440 Bronchial obstruction Diseases 0.000 description 1
AJPRLOSBAOSVNR-UHFFFAOYSA-N CN1C=NC2=C1C(=O)N(C(=O)N2C)CCCN3CCC(CC3)NC(=O)C4=CC=C(C=C4)F Chemical compound CN1C=NC2=C1C(=O)N(C(=O)N2C)CCCN3CCC(CC3)NC(=O)C4=CC=C(C=C4)F AJPRLOSBAOSVNR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920002261 Corn starch 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
206010012434 Dermatitis allergic Diseases 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
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
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-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
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229960000643 adenine Drugs 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 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
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
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
235000014113 dietary fatty acids Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 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
239000000706 filtrate Substances 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
239000008187 granular material Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 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
125000002887 hydroxy group Chemical group [H]O* 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
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
OEQODQMTSYQAAC-UHFFFAOYSA-N n-[1-(3-chloropropyl)piperidin-4-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1CCN(CCCCl)CC1 OEQODQMTSYQAAC-UHFFFAOYSA-N 0.000 description 1
IPEVTPCXBPOYDN-UHFFFAOYSA-N n-[1-(3-chloropropyl)piperidin-4-yl]-2-phenylacetamide Chemical compound C1CN(CCCCl)CCC1NC(=O)CC1=CC=CC=C1 IPEVTPCXBPOYDN-UHFFFAOYSA-N 0.000 description 1
FHLJEGCCUIVEJA-UHFFFAOYSA-N n-[1-(3-chloropropyl)piperidin-4-yl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1CCN(CCCCl)CC1 FHLJEGCCUIVEJA-UHFFFAOYSA-N 0.000 description 1
WWRZUCAXACNFSZ-UHFFFAOYSA-N n-[1-(3-chloropropyl)piperidin-4-yl]benzamide Chemical compound C1CN(CCCCl)CCC1NC(=O)C1=CC=CC=C1 WWRZUCAXACNFSZ-UHFFFAOYSA-N 0.000 description 1
KWNKWFNFEMCSIG-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine;hydrochloride Chemical compound Cl.ON=C1CCNCC1 KWNKWFNFEMCSIG-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 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
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 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
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 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
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 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
239000000725 suspension Substances 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
229940065721 systemic for obstructive airway disease xanthines Drugs 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
229940095064 tartrate Drugs 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 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
238000001665 trituration Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine

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

DD80221417A 1979-05-31 1980-05-28 Verfahren zur herstellung neuer xanthin-derivate DD151168A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792922159 DE2922159A1 (de)	1979-05-31	1979-05-31	Neue xanthin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD151168A5 true DD151168A5 (de)	1981-10-08

Family

ID=6072153

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221417A DD151168A5 (de)	1979-05-31	1980-05-28	Verfahren zur herstellung neuer xanthin-derivate

Country Status (13)

Country	Link
US (1)	US4284633A (fr)
EP (1)	EP0021103B1 (fr)
JP (1)	JPS55162785A (fr)
AT (1)	ATE3549T1 (fr)
AU (1)	AU529812B2 (fr)
CA (1)	CA1128040A (fr)
DD (1)	DD151168A5 (fr)
DE (2)	DE2922159A1 (fr)
ES (1)	ES8101074A1 (fr)
HU (1)	HU184291B (fr)
IL (1)	IL60176A (fr)
SU (1)	SU1079176A3 (fr)
ZA (1)	ZA803245B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4426383A (en)	1980-09-04	1984-01-17	Eisai Co., Ltd.	Theophylline and theobromine derivatives
CH648559A5 (de) *	1981-07-20	1985-03-29	Siegfried Ag	Theophyllinderivate und verfahren zu deren herstellung.
FR2558162B1 (fr) *	1984-01-17	1986-04-25	Adir	Nouveaux derives de la xanthine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant
US4548939A (en) *	1984-10-01	1985-10-22	Janssen Pharmaceutica N. V.	1H-Indol-3-yl containing 1,3-dimethyl-1H-purine-2,6-diones
US7550468B2 (en) *	2000-07-28	2009-06-23	Ing-Jun Chen	Theophylline and 3-isobutyl-1 methylxanthine based N-7 substituted derivatives displaying inhibitory activities on PDE-5 phospodiesterase

Family Cites Families (6)

* 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
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
US4061753A (en) *	1976-02-06	1977-12-06	Interx Research Corporation	Treating psoriasis with transient pro-drug forms of xanthine derivatives
DE2804416A1 (de) *	1978-02-02	1979-08-09	Boehringer Mannheim Gmbh	Neue purin-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
EP0011399A1 (fr) *	1978-11-11	1980-05-28	FISONS plc	Théophyllines-N-substituées, procédés pour leur préparation et compositions pharmaceutiques les contenant

1979
- 1979-05-31 DE DE19792922159 patent/DE2922159A1/de not_active Withdrawn
1980
- 1980-05-12 US US06/148,870 patent/US4284633A/en not_active Expired - Lifetime
- 1980-05-16 CA CA352,091A patent/CA1128040A/fr not_active Expired
- 1980-05-26 SU SU802925604A patent/SU1079176A3/ru active
- 1980-05-27 AU AU58787/80A patent/AU529812B2/en not_active Ceased
- 1980-05-28 IL IL60176A patent/IL60176A/xx unknown
- 1980-05-28 DD DD80221417A patent/DD151168A5/de unknown
- 1980-05-28 ES ES491915A patent/ES8101074A1/es not_active Expired
- 1980-05-29 AT AT80103002T patent/ATE3549T1/de not_active IP Right Cessation
- 1980-05-29 EP EP80103002A patent/EP0021103B1/fr not_active Expired
- 1980-05-29 DE DE8080103002T patent/DE3063450D1/de not_active Expired
- 1980-05-30 JP JP7164780A patent/JPS55162785A/ja active Pending
- 1980-05-30 HU HU801374A patent/HU184291B/hu unknown
- 1980-05-30 ZA ZA00803245A patent/ZA803245B/xx unknown

Also Published As

Publication number	Publication date
ES491915A0 (es)	1980-12-16
ES8101074A1 (es)	1980-12-16
DE2922159A1 (de)	1980-12-04
SU1079176A3 (ru)	1984-03-07
JPS55162785A (en)	1980-12-18
ATE3549T1 (de)	1983-06-15
AU529812B2 (en)	1983-06-23
ZA803245B (en)	1981-06-24
US4284633A (en)	1981-08-18
EP0021103B1 (fr)	1983-05-25
EP0021103A1 (fr)	1981-01-07
AU5878780A (en)	1980-12-04
IL60176A (en)	1983-06-15
HU184291B (en)	1984-07-30
IL60176A0 (en)	1980-07-31
DE3063450D1 (en)	1983-07-07
CA1128040A (fr)	1982-07-20

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EP0287907B1 (fr)	1992-08-19	Pyrazolo[3,4-d]pyrimidines, procédé pour leur préparation et leur utilisation comme médicaments
EP0212535B1 (fr)	1991-05-29	Dérivés de purine N6-disubstituée, procédé pour leur préparation ainsi que les médicaments les contenant
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EP0136658B1 (fr)	1989-04-26	-1-Benzyl-aminoalkyl-pyrrolidinones et leurs sels d'addition, procédé de préparation et médicaments les contenant
EP0013894B1 (fr)	1982-02-03	Aryléthers, procédé pour leur préparation et médicaments les contenant
DE3025385A1 (de)	1982-01-28	Neue tricyclische arylether, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
DE2939292A1 (de)	1981-04-09	N-phenoxyalkylpiperidin-derivate, verfahrenn zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
EP0163260B1 (fr)	1988-08-03	Nouvelles pyrrolidones substituées, procédé pour leur préparation et médicaments
DE2918261A1 (de)	1979-11-15	Neue purinderivate, verfahren zu deren herstellung, sie enthaltende arzneimittel und zwischenprodukte
DE3856501T2 (de)	2004-04-29	Schlafverbesserungsmittel
DE3125471A1 (de)	1982-03-18	"piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten"
EP0105210B1 (fr)	1987-03-04	Dérivés de l'isoquinoléine, leur procédé de préparation compositions pharmaceutiques les contenant et leur utilisation
EP0132811B1 (fr)	1988-09-28	Hydroxyméthyl-4 pyrrolidinones substituées en position 1, procédés pour leur préparation, compositions pharmaceutiques et produits intermédiaires
DD151168A5 (de)	1981-10-08	Verfahren zur herstellung neuer xanthin-derivate
EP0064255B1 (fr)	1984-12-12	Benzopyranyl éthers, leur procédé de préparation et médicament contenant ces composés et produits intermediaires
EP0621037A1 (fr)	1994-10-26	Composés pyrido-pyrimidinediones, leur préparation et leur utilisation pharmaceutique
EP0003558B1 (fr)	1981-10-21	9-(3-Pipéridinopropyl)-purines, procédés pour leur préparation, leur utilisation et compositions pharmaceutiques les contenant
CH624405A5 (fr)	1981-07-31
EP1444234A2 (fr)	2004-08-11	Pyrazolopyrimidinones deuterees et medicaments contenant ces composes
DD219642A5 (de)	1985-03-13	Verfahren zur herstellung von bis-(piperazinyl- bzw. homopiperazinyl)alkanen
DE69005904T2 (de)	1994-05-05	Phenylpyrimidonderivate.
DE2854341C2 (fr)	1990-05-23
EP0088986A2 (fr)	1983-09-21	Ethers phénoliques bicycliques, procédé pour leur préparation ainsi que médicaments contenant ces composés
EP0137993B1 (fr)	1990-01-17	11-Pipérazinyl-5H-imidazo[2,1-c][1,4]benzodiazépines, procédé pour leur préparation et intermédiaires et médicaments les contenant
DE69012407T2 (de)	1995-02-09	Imidazobenzodiazepine und ihre Salze, Verfahren zur Herstellung, Verwendung als Arzneimittel und diese Substanzen enthaltende Zusammensetzungen.