DD158400A5 - Verfahren zur herstellung von 3,8-dialkylxanthinen - Google Patents

Verfahren zur herstellung von 3,8-dialkylxanthinen Download PDF

Info

Publication number: DD158400A5
Authority: DD; German Democratic Republic
Prior art keywords: ethyl; propyl; butyl; methyl; general formula
Prior art date: 1980-04-18

Application number

DD81229229A

Other languages

German (de)

English (en)

Inventor

Per G Kjellin

Carl G A Persson

Original Assignee

Draco Ab

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.)

1980-04-18

Filing date

1981-04-14

Publication date

1983-01-12

1981-04-14 Application filed by Draco Ab filed Critical Draco Ab

1983-01-12 Publication of DD158400A5 publication Critical patent/DD158400A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 28
238000000034 method Methods 0.000 title claims abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 39
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
-1 n -propyl Chemical group 0.000 claims abstract description 17
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 15
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 11
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 9
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 35
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
238000007243 oxidative cyclization reaction Methods 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 6
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 4
230000001225 therapeutic effect Effects 0.000 abstract description 2
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 abstract 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000013078 crystal Substances 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
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229960000278 theophylline Drugs 0.000 description 11
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 7
SHKJXAPOAVPNKW-UHFFFAOYSA-N 6-amino-1-ethyl-5-nitrosopyrimidine-2,4-dione Chemical compound CCN1C(N)=C(N=O)C(=O)NC1=O SHKJXAPOAVPNKW-UHFFFAOYSA-N 0.000 description 6
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239000003795 chemical substances by application Substances 0.000 description 6
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230000000694 effects Effects 0.000 description 6
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239000002585 base Substances 0.000 description 4
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
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229920002261 Corn starch Polymers 0.000 description 3
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
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239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
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AHSKLSFFKJHWAI-RGMNGODLSA-N (2s)-2-amino-5-[[amino(dimethylamino)methylidene]amino]pentanoic acid;hydrochloride Chemical compound Cl.CN(C)C(N)=NCCC[C@H](N)C(O)=O AHSKLSFFKJHWAI-RGMNGODLSA-N 0.000 description 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
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CLRHVOHIFNLQBD-UHFFFAOYSA-N 3-ethyl-8-methyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CC)C2=C1NC(C)=N2 CLRHVOHIFNLQBD-UHFFFAOYSA-N 0.000 description 2
PJHVUYYGBOUXNX-UHFFFAOYSA-N 6-amino-5-nitroso-1-propylpyrimidine-2,4-dione Chemical compound CCCN1C(N)=C(N=O)C(=O)NC1=O PJHVUYYGBOUXNX-UHFFFAOYSA-N 0.000 description 2
CESVXSGKVYVAIY-UHFFFAOYSA-N 8-ethyl-3-propyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCC)C2=C1NC(CC)=N2 CESVXSGKVYVAIY-UHFFFAOYSA-N 0.000 description 2
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 2
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CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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208000024172 Cardiovascular disease Diseases 0.000 description 2
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DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-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
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231100000252 nontoxic Toxicity 0.000 description 2
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
229960004484 carbachol Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000007911 effervescent powder Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form 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
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (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)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
General Health & Medical Sciences (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD81229229A 1980-04-18 1981-04-14 Verfahren zur herstellung von 3,8-dialkylxanthinen DD158400A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8002910A SE8002910L (sv)	1980-04-18	1980-04-18	3,8-dialkylxantiner, forfarande for deras framstellning, beredning och metoder for behandling av kronisk obstruktiv luftvegssjukdom och kardiovaskulera sjukdomar

Publications (1)

Publication Number	Publication Date
DD158400A5 true DD158400A5 (de)	1983-01-12

Family

ID=20340763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81229229A DD158400A5 (de)	1980-04-18	1981-04-14	Verfahren zur herstellung von 3,8-dialkylxanthinen

Country Status (21)

Country	Link
US (1)	US4546182A (pl)
EP (1)	EP0038784B1 (pl)
JP (1)	JPS56166191A (pl)
AT (1)	ATE10099T1 (pl)
AU (1)	AU543122B2 (pl)
CA (1)	CA1156229A (pl)
DD (1)	DD158400A5 (pl)
DE (1)	DE3166893D1 (pl)
DK (1)	DK151631B (pl)
ES (1)	ES8203088A1 (pl)
FI (1)	FI69465C (pl)
GR (1)	GR82347B (pl)
HU (1)	HU185254B (pl)
IE (1)	IE51106B1 (pl)
NO (1)	NO811161L (pl)
NZ (1)	NZ196829A (pl)
PH (1)	PH16264A (pl)
PL (1)	PL134762B1 (pl)
PT (1)	PT72881B (pl)
SE (1)	SE8002910L (pl)
ZA (1)	ZA811729B (pl)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE7810947L (sv) *	1978-10-20	1980-04-21	Draco Ab	3-alkylxanthines
US4710503A (en) *	1985-02-07	1987-12-01	Euroceltique S.A.	6-thioxanthine derivatives
GB8618931D0 (en) *	1986-08-02	1986-09-10	Euro Celtique Sa	6-thioxanthines
US5298508A (en) *	1988-07-19	1994-03-29	The United States Of America As Represented By The Department Of Health And Human Services	Irreversible inhibitors of adenosine receptors
JP2843634B2 (ja) *	1989-03-06	1999-01-06	協和醗酵工業株式会社	キサンチン誘導体
IT1229195B (it) *	1989-03-10	1991-07-25	Poli Ind Chimica Spa	Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche.
AU5436790A (en) *	1989-04-19	1990-11-16	United States of America, as represented by the Secretary, U.S. Department of Commerce, The	Sulfer-containing xanthine derivatives as adenosin antagonists
CA2030112A1 (en) *	1989-11-24	1991-05-25	Yasuo Ito	Xanthine compound, method for preparing thereof, and a pharmaceutical composition comprising the same
US5366977A (en) *	1992-09-29	1994-11-22	The United States Of America, As Represented By The Department Of Health And Human Services	Method of treating cystic fibrosis using 8-cyclopentyl-1,3-dipropylxanthine or xanthine amino congeners
DE4311538C1 (de) *	1993-04-07	1994-10-06	Boehringer Ingelheim Kg	Verfahren zur Herstellung von 1,3-Dimethyl-4,5-diaminouracil
AU6781194A (en) *	1993-05-03	1994-11-21	United States Of America, Represented By The Secretary, Department Of Health And Human Services, The	8-substituted 1,3,7-trialkyl-xanthine derivatives as a2-selective adenosine receptor antagonists
AU2603197A (en)	1996-04-10	1997-10-29	United States Of America, Represented By The Secretary, Department Of Health And Human Services, The	Use of an a1 adenosine receptor agonist to treat cerebral ischaemia

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS53890B2 (pl) *	1972-04-22	1978-01-12
CA1077932A (en) *	1976-03-31	1980-05-20	Berlex Laboratories, Inc.	Xanthine compounds and method of treating bronchospastic and allergic diseases
US4089959A (en) *	1976-03-31	1978-05-16	Cooper Laboratories, Inc.	Long-acting xanthine bronchodilators and antiallergy agents
SE416810C (sv) *	1977-10-14	1982-07-19	Draco Ab	Forfarande for framstellning av xantinderivat med antiallergisk aktivitet
SE7810946L (sv) *	1978-10-20	1980-04-21	Draco Ab	Metod att behandla kronisk obstruktiv luftvegssjukdom
SE7810947L (sv) *	1978-10-20	1980-04-21	Draco Ab	3-alkylxanthines

1980
- 1980-04-18 SE SE8002910A patent/SE8002910L/xx not_active Application Discontinuation
1981
- 1981-03-09 DE DE8181850039T patent/DE3166893D1/de not_active Expired
- 1981-03-09 AT AT81850039T patent/ATE10099T1/de not_active IP Right Cessation
- 1981-03-09 EP EP81850039A patent/EP0038784B1/en not_active Expired
- 1981-03-16 ZA ZA00811729A patent/ZA811729B/xx unknown
- 1981-03-17 CA CA000373230A patent/CA1156229A/en not_active Expired
- 1981-04-01 PH PH25455A patent/PH16264A/en unknown
- 1981-04-03 NO NO811161A patent/NO811161L/no unknown
- 1981-04-08 IE IE769/81A patent/IE51106B1/en unknown
- 1981-04-14 DD DD81229229A patent/DD158400A5/de unknown
- 1981-04-14 DK DK168281AA patent/DK151631B/da active IP Right Grant
- 1981-04-15 ES ES501400A patent/ES8203088A1/es not_active Expired
- 1981-04-15 NZ NZ196829A patent/NZ196829A/en unknown
- 1981-04-15 AU AU69555/81A patent/AU543122B2/en not_active Ceased
- 1981-04-15 GR GR64702A patent/GR82347B/el unknown
- 1981-04-16 FI FI811212A patent/FI69465C/fi not_active IP Right Cessation
- 1981-04-16 PT PT72881A patent/PT72881B/pt unknown
- 1981-04-17 PL PL1981230737A patent/PL134762B1/pl unknown
- 1981-04-17 HU HU811020A patent/HU185254B/hu unknown
- 1981-04-17 JP JP5724181A patent/JPS56166191A/ja active Pending
1983
- 1983-08-16 US US06/523,731 patent/US4546182A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU6955581A (en)	1981-10-22
HU185254B (en)	1984-12-28
PL134762B1 (en)	1985-09-30
PT72881A (en)	1981-05-01
US4546182A (en)	1985-10-08
ZA811729B (en)	1982-04-28
SE8002910L (sv)	1981-10-19
CA1156229A (en)	1983-11-01
EP0038784A3 (en)	1982-01-20
PH16264A (en)	1983-08-23
AU543122B2 (en)	1985-04-04
EP0038784A2 (en)	1981-10-28
PT72881B (en)	1983-03-29
DK168281A (da)	1981-10-19
DE3166893D1 (en)	1984-12-06
DK151631B (da)	1987-12-21
FI69465C (fi)	1986-02-10
IE51106B1 (en)	1986-10-01
NO811161L (no)	1981-10-19
ES501400A0 (es)	1982-02-16
JPS56166191A (en)	1981-12-21
FI69465B (fi)	1985-10-31
NZ196829A (en)	1984-12-14
PL230737A1 (pl)	1982-03-29
FI811212L (fi)	1981-10-19
IE810796L (en)	1981-10-18
ES8203088A1 (es)	1982-02-16
GR82347B (pl)	1984-12-13
ATE10099T1 (de)	1984-11-15
EP0038784B1 (en)	1984-10-31

Publication	Publication Date	Title
EP0011609B1 (en)	1983-04-13	Xanthine derivatives and pharmaceutical preparations containing these derivatives for use in the treatment of chronic obstructive airway disease and cardiac disease
DD146708A5 (de)	1981-02-25	Verfahren zur herstellung von 3-alkylxanthinen
DD202001A5 (de)	1983-08-24	Verfahren zur herstellung von aminoaethanolen
DE2558501C2 (pl)	1987-07-16
DE1643262C3 (de)	1975-06-26	i-Phenoxy^-hydroxy-S-alklyaminopropane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD201139A5 (de)	1983-07-06	Verfahren zur herstellung von (-)-n-methyl-3-(2-methylphenoxy)-3-phenylpropylamin und seinen pharmazeutisch unbedenklichen salzen
DD139855A5 (de)	1980-01-23	Verfahren zur herstellung von xanthinderivaten
DE2734678C2 (de)	1982-07-15	Epininester,Verfahren zu ihrer Herstellung und Heilmittel
DE2713389A1 (de)	1977-10-13	Neuartige xanthinverbindungen und dieselben enthaltende pharmazeutische zubereitung
US4546182A (en)	1985-10-08	3,8-Dialkylxanthines
DE2640972A1 (de)	1977-04-14	Aminoaethanolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2720545C3 (de)	1980-09-11	Derivate des 2,4-Diamino-6,7-dimethoxychinazolins, ihre Herstellung und pharmazeutische Mittel
DE2403122C2 (pl)	1990-03-22
CH634574A5 (de)	1983-02-15	Verfahren zur herstellung von 7-(2,3-dihydroxypropyl)-1,3-di-n-propylxanthin.
DE69919478T2 (de)	2005-09-08	7-Aminopyrido(2,3-d)-pyrimidine Derivate zur Behandlung von Bronchialasthma
DE2460929C2 (pl)	1987-12-17
DE69007422T2 (de)	1994-07-14	1-(4-Aminophenyl)-2-piperidinopropanon-Derivate, Verfahren zu deren Herstellung und therapeutische Verwendung.
EP0081748A2 (de)	1983-06-22	Verfahren zur Herstellung von (-)-2-(1-(2,6-Dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE1965343A1 (de)	1970-07-23	Arzneimittel,insbesondere zur Herabsetzung der Schleimviskositaet und Anwendung als hustenstillendes Mittel,und Verfahren zu seiner Herstellung
DE1695298B2 (de)	1975-01-23	S-AcetamMo-e-methyl-e-n-propyl-striazolo eckige Klammer auf 4,3-a eckige Klammer zu pyrazin und Verfahren zu seiner Herstellung und Arzneimittel
DD202545A5 (de)	1983-09-21	Verfahren zur herstellung eines 1-benzyl-3,4-dihydroisochinolin-derivates
EP0035733B1 (de)	1983-09-14	Neue 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-aminopropane und Verfahren zu ihrer Herstellung
DE3017560A1 (de)	1980-11-13	9-amino-6,7-dihydro-4h-pyrido eckige klammer auf 1,2-a eckige klammer zu pyrimidin-4-on-derivate, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische kompositionen
DE2227846A1 (de)	1973-01-04	Phenoxyessigsaeure-derivate und verfahren zu ihrer herstellung