CA1075692A - Derives de la xanthine - Google Patents

Derives de la xanthine

Info

Publication number: CA1075692A
Authority: CA; Canada
Prior art keywords: methyl; xanthine; propylxanthine; carbon atoms; propyl
Prior art date: 1977-12-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA320,437A

Other languages

English (en)

Inventor

Werner Mohler

Jaromir Komarek

Manfred Jayme

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1977-12-07

Filing date

1977-12-07

Publication date

1980-04-15

1977-12-07 Application filed by Hoechst AG filed Critical Hoechst AG

1977-12-07 Priority to CA320,437A priority Critical patent/CA1075692A/fr

1980-04-15 Application granted granted Critical

1980-04-15 Publication of CA1075692A publication Critical patent/CA1075692A/fr

Status Expired legal-status Critical Current

Links

LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims abstract description 26
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 46
229940075420 xanthine Drugs 0.000 claims abstract description 43
239000000126 substance Substances 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 35
239000000047 product Substances 0.000 claims abstract description 33
-1 alkali metal salt Chemical class 0.000 claims abstract description 27
239000002253 acid Substances 0.000 claims abstract description 24
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 17
239000002904 solvent Substances 0.000 claims abstract description 17
125000002947 alkylene group Chemical group 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 10
150000002576 ketones Chemical class 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 7
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 5
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 5
230000003647 oxidation Effects 0.000 claims abstract description 5
238000007254 oxidation reaction Methods 0.000 claims abstract description 5
TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
MHNVSFOURBQRPK-UHFFFAOYSA-N 3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCC MHNVSFOURBQRPK-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
WQRASISGTROKJS-UHFFFAOYSA-N 3-methyl-1-(6-oxoheptyl)-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCCC(C)=O)C(=O)C2=C1N=CN2CCC WQRASISGTROKJS-UHFFFAOYSA-N 0.000 claims description 8
RBQOQRRFDPXAGN-UHFFFAOYSA-N Propentofylline Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCC RBQOQRRFDPXAGN-UHFFFAOYSA-N 0.000 claims description 8
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
125000005188 oxoalkyl group Chemical group 0.000 claims description 5
239000005977 Ethylene Substances 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
HTIAHMISHDFTJR-UHFFFAOYSA-N 1-(2-bromoethyl)-3-methyl-7-propylpurine-2,6-dione Chemical compound BrCCN1C(=O)N(C=2N=CN(C2C1=O)CCC)C HTIAHMISHDFTJR-UHFFFAOYSA-N 0.000 claims description 2
XVCPSEYOPVLWFC-UHFFFAOYSA-N 3-methyl-1-(4-oxopentyl)-7h-purine-2,6-dione Chemical compound O=C1N(CCCC(=O)C)C(=O)N(C)C2=C1NC=N2 XVCPSEYOPVLWFC-UHFFFAOYSA-N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
ARZOGANVDPBFCO-UHFFFAOYSA-N 3-methyl-1-(4-oxopentyl)-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCC(C)=O)C(=O)C2=C1N=CN2CCC ARZOGANVDPBFCO-UHFFFAOYSA-N 0.000 claims 6
KOONCSGIOHWCEN-UHFFFAOYSA-N 1-(3-bromopropyl)-3-methyl-7-propylpurine-2,6-dione Chemical compound BrCCCN1C(=O)N(C=2N=CN(C2C1=O)CCC)C KOONCSGIOHWCEN-UHFFFAOYSA-N 0.000 claims 1
MLCBKATYKBTVKQ-UHFFFAOYSA-N 1-(4-hydroxypentyl)-3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCC(C)O)C(=O)C2=C1N=CN2CCC MLCBKATYKBTVKQ-UHFFFAOYSA-N 0.000 claims 1
FVSINRDBOGWXHN-UHFFFAOYSA-N 1-(6-hydroxyheptyl)-3-methyl-7-propylpurine-2,6-dione Chemical compound OC(CCCCCN1C(=O)N(C=2N=CN(C2C1=O)CCC)C)C FVSINRDBOGWXHN-UHFFFAOYSA-N 0.000 claims 1
YROJDXSVHMRWNN-UHFFFAOYSA-N 3-methyl-1-(6-oxoheptyl)-7h-purine-2,6-dione Chemical compound O=C1N(CCCCCC(=O)C)C(=O)N(C)C2=C1NC=N2 YROJDXSVHMRWNN-UHFFFAOYSA-N 0.000 claims 1
LUKOJLYOCYSYND-UHFFFAOYSA-N 8-methyl-1-(5-oxohexyl)-3,7-dihydropurine-2,6-dione Chemical compound CC(=O)CCCCn1c(=O)[nH]c2nc(C)[nH]c2c1=O LUKOJLYOCYSYND-UHFFFAOYSA-N 0.000 claims 1
230000002792 vascular Effects 0.000 abstract description 5
239000008280 blood Substances 0.000 abstract description 3
210000004369 blood Anatomy 0.000 abstract description 3
230000007812 deficiency Effects 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 94
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 32
229940083608 sodium hydroxide Drugs 0.000 description 32
239000000243 solution Substances 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
238000001953 recrystallisation Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 16
230000008084 cerebral blood perfusion Effects 0.000 description 16
238000003756 stirring Methods 0.000 description 16
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
229940073584 methylene chloride Drugs 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
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 10
241000699666 Mus <mouse, genus> Species 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000001117 sulphuric acid Substances 0.000 description 10
235000011149 sulphuric acid Nutrition 0.000 description 10
RDIDOICNEQWODO-UHFFFAOYSA-N 3-butyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCC)C2=C1NC=N2 RDIDOICNEQWODO-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
229940093956 potassium carbonate Drugs 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
241000282326 Felis catus Species 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000013078 crystal Substances 0.000 description 8
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
241000700199 Cavia porcellus Species 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 7
230000001813 broncholytic effect Effects 0.000 description 7
238000001816 cooling Methods 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
229960001340 histamine Drugs 0.000 description 7
230000000144 pharmacologic effect Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 6
229960004373 acetylcholine Drugs 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 6
230000003480 fibrinolytic effect Effects 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
229960000278 theophylline Drugs 0.000 description 6
YMIISQFLRUQIIW-UHFFFAOYSA-N 1-bromohexan-2-one Chemical compound CCCCC(=O)CBr YMIISQFLRUQIIW-UHFFFAOYSA-N 0.000 description 5
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
230000008081 blood perfusion Effects 0.000 description 5
238000004821 distillation Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229960001866 silicon dioxide Drugs 0.000 description 5
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 5
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
OXTJFLMERRCYFJ-UHFFFAOYSA-N 3-methyl-7-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCCCC(=O)C OXTJFLMERRCYFJ-UHFFFAOYSA-N 0.000 description 3
GISWGHGEIIOKGX-UHFFFAOYSA-N 7-ethyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CC GISWGHGEIIOKGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229960003556 aminophylline Drugs 0.000 description 3
PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
230000002490 cerebral effect Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
230000000916 dilatatory effect Effects 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000005923 long-lasting effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
229960001407 sodium bicarbonate Drugs 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
HDAPVDGMACVEKL-UHFFFAOYSA-N 1,3-dibutyl-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCCC)C2=C1NC=N2 HDAPVDGMACVEKL-UHFFFAOYSA-N 0.000 description 2
GDCZHIPNTVBMPT-UHFFFAOYSA-N 3-ethyl-7-propylpurine-2,6-dione Chemical compound CCN1C(=O)NC(=O)C2=C1N=CN2CCC GDCZHIPNTVBMPT-UHFFFAOYSA-N 0.000 description 2
XHZWTLQBNHVZDX-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-7-(5-oxohexyl)purine-2,6-dione Chemical compound O=C1N(CC(C)C)C(=O)N(C)C2=C1N(CCCCC(C)=O)C=N2 XHZWTLQBNHVZDX-UHFFFAOYSA-N 0.000 description 2
QMUGICMOASIURD-UHFFFAOYSA-N 7-butyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCCC QMUGICMOASIURD-UHFFFAOYSA-N 0.000 description 2
MROQSUMVRJJJLI-UHFFFAOYSA-N 7-ethyl-3-methyl-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CC MROQSUMVRJJJLI-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
208000036366 Sensation of pressure Diseases 0.000 description 2
208000010513 Stupor Diseases 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000012752 auxiliary agent Substances 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
UDIGDODUJVQRPE-UHFFFAOYSA-N 1,3-dibutyl-7-(4-oxopentyl)purine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCCC)C2=C1N(CCCC(C)=O)C=N2 UDIGDODUJVQRPE-UHFFFAOYSA-N 0.000 description 1
CSQDGGFMWHMVLK-UHFFFAOYSA-N 1-(3-bromopropyl)-3-ethyl-7-propylpurine-2,6-dione Chemical compound BrCCCN1C(=O)N(C=2N=CN(C=2C1=O)CCC)CC CSQDGGFMWHMVLK-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
SNVVZCPNLVAKLC-UHFFFAOYSA-N 1-chloroheptan-2-one Chemical compound CCCCCC(=O)CCl SNVVZCPNLVAKLC-UHFFFAOYSA-N 0.000 description 1
OFERIRWCHSOJJT-UHFFFAOYSA-N 2-(3-chloropropyl)-2-methyl-1,3-dioxolane Chemical compound ClCCCC1(C)OCCO1 OFERIRWCHSOJJT-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ADTNFGURCPCFPZ-UHFFFAOYSA-N 3-butyl-1-methyl-7-(4-oxopentyl)purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CCCC)C2=C1N(CCCC(C)=O)C=N2 ADTNFGURCPCFPZ-UHFFFAOYSA-N 0.000 description 1
AMPAUDSKWOYFGA-UHFFFAOYSA-N 3-butyl-1-methyl-7-(6-oxoheptyl)purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CCCC)C2=C1N(CCCCCC(C)=O)C=N2 AMPAUDSKWOYFGA-UHFFFAOYSA-N 0.000 description 1
YBGZKURKPTVHNR-UHFFFAOYSA-N 3-butyl-1-methyl-7-(7-oxooctyl)purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CCCC)C2=C1N(CCCCCCC(C)=O)C=N2 YBGZKURKPTVHNR-UHFFFAOYSA-N 0.000 description 1
UHOAEOYZGZGDTP-UHFFFAOYSA-N 3-butyl-7-(4-oxopentyl)purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCC)C2=C1N(CCCC(C)=O)C=N2 UHOAEOYZGZGDTP-UHFFFAOYSA-N 0.000 description 1
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
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YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical class CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 1
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239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA320,437A 1977-12-07 1977-12-07 Derives de la xanthine Expired CA1075692A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA320,437A CA1075692A (fr)	1977-12-07	1977-12-07	Derives de la xanthine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA320,437A CA1075692A (fr)	1977-12-07	1977-12-07	Derives de la xanthine

Publications (1)

Publication Number	Publication Date
CA1075692A true CA1075692A (fr)	1980-04-15

Family

ID=4113408

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA320,437A Expired CA1075692A (fr)	1977-12-07	1977-12-07	Derives de la xanthine

Country Status (1)

Country	Link
CA (1)	CA1075692A (fr)

1977
- 1977-12-07 CA CA320,437A patent/CA1075692A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-04-15	MKEX	Expiry

Publication	Publication Date	Title
US4289776A (en)	1981-09-15	Xanthine derivatives
JP2988711B2 (ja)	1999-12-13	縮合プリン誘導体
KR0160768B1 (ko)	1998-12-01	제약학적 용도를 갖는 8-치환 크산틴 화합물
EP0001735B1 (fr)	1982-09-01	Dérivés de xanthine à activité antiallergique et compositions pharmaceutiques les contenant
JP2613355B2 (ja)	1997-05-28	パーキンソン氏病治療剤
JP2843634B2 (ja)	1999-01-06	キサンチン誘導体
US4146715A (en)	1979-03-27	2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines
US4325956A (en)	1982-04-20	Method and pharmaceutical preparation for treating chronic obstructive airway disease and cardiac disease, and intermediates for the preparation of therapeutically active xanthine derivatives
EP0559893B1 (fr)	1999-02-03	Derive de xanthine
EP0369744B1 (fr)	1994-09-21	Dérivés de Xanthine, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4544556A (en)	1985-10-01	Xanthine derivatives, pharmaceutical compositions containing same and their therapeutic use
KR970002232B1 (ko)	1997-02-26	N-치환 아미드 유도체
EP0038784A2 (fr)	1981-10-28	3,8-Dialkylxanthines, procédés pour leur préparation et compositions les contenant
US4060616A (en)	1977-11-29	Purine derivatives with repeating unit
US4372959A (en)	1983-02-08	1-(5-Oxohexyl)-3-alkyl-7-(2-oxopropyl)xanthines
US4232155A (en)	1980-11-04	Purine compounds
CA1125750A (fr)	1982-06-15	Cetals de xanthines
US4942143A (en)	1990-07-17	Imidazothiadiazine derivatives, and their use as medicaments
CA1075693A (fr)	1980-04-15	Derives de la xanthine
CA1075690A (fr)	1980-04-15	Derives de la xanthine
CA1075691A (fr)	1980-04-15	Derives de la xanthine
EP0560354A1 (fr)	1993-09-15	Dérivés de la xanthine
US3989833A (en)	1976-11-02	Pharmaceutical compositions containing adenine derivatives
CA2030112A1 (fr)	1991-05-25	Compose de xanthine, methode de preparation et composition pharmaceutique contenant ledit compose
JPS6141915B2 (fr)	1986-09-18