CA1123435A - Compose pharmaceutique , alkenyl xanthines contenues dans celui-ci et procede de preparation - Google Patents

Compose pharmaceutique , alkenyl xanthines contenues dans celui-ci et procede de preparation

Info

Publication number: CA1123435A
Authority: CA; Canada
Prior art keywords: methyl; carbon atoms; xanthine; alkenyl; enyl
Prior art date: 1977-04-02
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

CA300,333A

Other languages

English (en)

Inventor

Harald Furrer

Alfons Soder

Jaromir Komarek

Heinz-Joachim Hinze

Gerhard Munch

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.)

1977-04-02

Filing date

1978-04-03

Publication date

1982-05-11

1978-04-03 Application filed by Hoechst AG filed Critical Hoechst AG

1980-10-23 Priority to CA363,133A priority Critical patent/CA1127083A/fr

1982-05-11 Application granted granted Critical

1982-05-11 Publication of CA1123435A publication Critical patent/CA1123435A/fr

Status Expired legal-status Critical Current

Links

125000003342 alkenyl group Chemical group 0.000 title claims abstract description 32
238000004519 manufacturing process Methods 0.000 title claims 2
239000008194 pharmaceutical composition Substances 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 29
-1 1-propyl- Chemical group 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229940075420 xanthine Drugs 0.000 claims description 46
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
125000005188 oxoalkyl group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
239000003513 alkali Substances 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims 1
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 5
230000008081 blood perfusion Effects 0.000 abstract description 2
230000001737 promoting effect Effects 0.000 abstract description 2
230000002792 vascular Effects 0.000 abstract description 2
BFCDFTHTSVTWOG-PXNSSMCTSA-N (1r,2s)-2-(octylamino)-1-(4-propan-2-ylsulfanylphenyl)propan-1-ol Chemical compound CCCCCCCCN[C@@H](C)[C@H](O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-PXNSSMCTSA-N 0.000 abstract 1
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 22
239000000203 mixture Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 8
239000003480 eluent Substances 0.000 description 7
DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
210000004556 brain Anatomy 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000003756 stirring Methods 0.000 description 5
JVFMBDSSMVYTQR-UHFFFAOYSA-N 3-ethyl-7-hex-5-enylpurine-2,6-dione Chemical compound O=C1NC(=O)N(CC)C2=C1N(CCCCC=C)C=N2 JVFMBDSSMVYTQR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000282326 Felis catus Species 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
238000004821 distillation Methods 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
JRUPQQAQYJPGJU-UHFFFAOYSA-N 7-hex-5-enyl-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCCCC=C)C=N2 JRUPQQAQYJPGJU-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000012730 sustained-release form Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 3
QUNWUDVFRNGTCO-UHFFFAOYSA-N 1,7-dimethylxanthine Chemical compound N1C(=O)N(C)C(=O)C2=C1N=CN2C QUNWUDVFRNGTCO-UHFFFAOYSA-N 0.000 description 2
ACNSYFWYLIPJSQ-UHFFFAOYSA-N 3-methyl-7-pent-4-enylpurine-2,6-dione Chemical compound O=C1NC(=O)N(C)C2=C1N(CCCC=C)C=N2 ACNSYFWYLIPJSQ-UHFFFAOYSA-N 0.000 description 2
GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 description 2
ZEXSXUJZXJUWSH-UHFFFAOYSA-N 7-but-3-enyl-3-ethylpurine-2,6-dione Chemical compound O=C1NC(=O)N(CC)C2=C1N(CCC=C)C=N2 ZEXSXUJZXJUWSH-UHFFFAOYSA-N 0.000 description 2
CTNCRPGIDZSAAK-UHFFFAOYSA-N 7-hex-4-enyl-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCC=CC CTNCRPGIDZSAAK-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
229960003556 aminophylline Drugs 0.000 description 2
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 2
230000037396 body weight Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
229960004559 theobromine Drugs 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
239000012991 xanthate Substances 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
PHJMZLGGUBFXTN-UHFFFAOYSA-N 1,3,7-tris(pent-4-enyl)purine-2,6-dione Chemical compound C=CCCCN1C(=O)N(CCCC=C)C(=O)C2=C1N=CN2CCCC=C PHJMZLGGUBFXTN-UHFFFAOYSA-N 0.000 description 1
HNAAXFRSTDWNIL-UHFFFAOYSA-N 1,3-dibutyl-7-hex-5-enylpurine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCCC)C2=C1N(CCCCC=C)C=N2 HNAAXFRSTDWNIL-UHFFFAOYSA-N 0.000 description 1
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 1
OQCGMUMXSFXGGL-UHFFFAOYSA-N 1,3-diethyl-7-hex-5-enylpurine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CC)C2=C1N(CCCCC=C)C=N2 OQCGMUMXSFXGGL-UHFFFAOYSA-N 0.000 description 1
DZEATAQARAADMI-UHFFFAOYSA-N 1,3-diethyl-7-pent-4-enylpurine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CC)C2=C1N(CCCC=C)C=N2 DZEATAQARAADMI-UHFFFAOYSA-N 0.000 description 1
GIMNFISWKTZFKJ-UHFFFAOYSA-N 1,3-diethyl-7h-purine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CC)C2=C1NC=N2 GIMNFISWKTZFKJ-UHFFFAOYSA-N 0.000 description 1
OALSRZVYEKEERN-UHFFFAOYSA-N 1,3-dimethyl-7-(2-methylpent-2-enyl)purine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(C)=CCC OALSRZVYEKEERN-UHFFFAOYSA-N 0.000 description 1
TXAQBTNRJUDDRY-UHFFFAOYSA-N 1,3-dimethyl-7-(5-methylhex-5-enyl)purine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCC(=C)C TXAQBTNRJUDDRY-UHFFFAOYSA-N 0.000 description 1
XBEDAMVJWVPVDS-UHFFFAOYSA-N 1,3-dimethyl-7-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCC(=O)C XBEDAMVJWVPVDS-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UZDQEBXXZLNWHQ-UHFFFAOYSA-N 1,7-bis(but-3-enyl)-3-ethylpurine-2,6-dione Chemical compound O=C1N(CCC=C)C(=O)N(CC)C2=C1N(CCC=C)C=N2 UZDQEBXXZLNWHQ-UHFFFAOYSA-N 0.000 description 1
LHUFTXJVEKAXTJ-UHFFFAOYSA-N 1,7-bis(hex-5-enyl)-3-methylpurine-2,6-dione Chemical compound O=C1N(CCCCC=C)C(=O)N(C)C2=C1N(CCCCC=C)C=N2 LHUFTXJVEKAXTJ-UHFFFAOYSA-N 0.000 description 1
ZFDCJXKKCGCUQF-UHFFFAOYSA-N 1,7-dimethyl-3-pent-4-enylpurine-2,6-dione Chemical compound C=CCCCN1C(=O)N(C)C(=O)C2=C1N=CN2C ZFDCJXKKCGCUQF-UHFFFAOYSA-N 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
OJSUFFNCXVQQPG-UHFFFAOYSA-N 1-but-3-enyl-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCC=C)C(=O)C2=C1N=CN2C OJSUFFNCXVQQPG-UHFFFAOYSA-N 0.000 description 1
ZAUXOSKREHJERD-UHFFFAOYSA-N 1-but-3-enyl-3-ethyl-7-hex-5-enylpurine-2,6-dione Chemical compound O=C1N(CCC=C)C(=O)N(CC)C2=C1N(CCCCC=C)C=N2 ZAUXOSKREHJERD-UHFFFAOYSA-N 0.000 description 1
YWVAKZHZDSXEEL-UHFFFAOYSA-N 1-but-3-enyl-3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCC=C)C(=O)C2=C1N=CN2CCC YWVAKZHZDSXEEL-UHFFFAOYSA-N 0.000 description 1
LGHBUOGSOHTHTO-UHFFFAOYSA-N 1-ethyl-7-hex-5-enyl-3-methylpurine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(C)C2=C1N(CCCCC=C)C=N2 LGHBUOGSOHTHTO-UHFFFAOYSA-N 0.000 description 1
LZRTZRBKFZHHQT-UHFFFAOYSA-N 1-hex-5-enyl-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC=C)C(=O)C2=C1N=CN2C LZRTZRBKFZHHQT-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
YOBYAKWFGPDGHG-UHFFFAOYSA-N 3,7-dimethyl-1-pent-4-enylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCC=C)C(=O)C2=C1N=CN2C YOBYAKWFGPDGHG-UHFFFAOYSA-N 0.000 description 1
PYJNGUQCDFMIMS-UHFFFAOYSA-N 3-ethyl-1-hex-5-enyl-7-methylpurine-2,6-dione Chemical compound O=C1N(CCCCC=C)C(=O)N(CC)C2=C1N(C)C=N2 PYJNGUQCDFMIMS-UHFFFAOYSA-N 0.000 description 1
OTUCSVCIIQRSNG-UHFFFAOYSA-N 3-ethyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CC)C2=C1NC=N2 OTUCSVCIIQRSNG-UHFFFAOYSA-N 0.000 description 1
UZRCRCBKXULVTM-UHFFFAOYSA-N 3-hex-5-enyl-1,7-dimethylpurine-2,6-dione Chemical compound C=CCCCCN1C(=O)N(C)C(=O)C2=C1N=CN2C UZRCRCBKXULVTM-UHFFFAOYSA-N 0.000 description 1
MHNVSFOURBQRPK-UHFFFAOYSA-N 3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCC MHNVSFOURBQRPK-UHFFFAOYSA-N 0.000 description 1
LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
MMISUADGBISLRF-UHFFFAOYSA-N 7-(2-methylpropyl)-3h-purine-2,6-dione Chemical compound N1C(=O)NC(=O)C2=C1N=CN2CC(C)C MMISUADGBISLRF-UHFFFAOYSA-N 0.000 description 1
HSUAWWZANQUYQS-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCC(O)C HSUAWWZANQUYQS-UHFFFAOYSA-N 0.000 description 1
AFFGLYSEFLHGSL-UHFFFAOYSA-N 7-but-3-enyl-3-methylpurine-2,6-dione Chemical compound O=C1NC(=O)N(C)C2=C1N(CCC=C)C=N2 AFFGLYSEFLHGSL-UHFFFAOYSA-N 0.000 description 1
COCPIYBVBNOICS-UHFFFAOYSA-N 7-hex-5-enyl-3-methylpurine-2,6-dione Chemical compound O=C1NC(=O)N(C)C2=C1N(CCCCC=C)C=N2 COCPIYBVBNOICS-UHFFFAOYSA-N 0.000 description 1
TVZXSTTUKANBFF-UHFFFAOYSA-N 8-butyl-3,7-dihydropurine-2,6-dione Chemical compound N1C(=O)NC(=O)C2=C1N=C(CCCC)N2 TVZXSTTUKANBFF-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
IVTVLQLHJNHNKC-UHFFFAOYSA-N C=CCCCCC1=NC2=C(N1)C(=O)NC(=O)N2 Chemical compound C=CCCCCC1=NC2=C(N1)C(=O)NC(=O)N2 IVTVLQLHJNHNKC-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
102000014171 Milk Proteins Human genes 0.000 description 1
108010011756 Milk Proteins Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012154 double-distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
235000021239 milk protein Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 1
125000002270 phosphoric acid ester group Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical compound [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000009492 tablet coating Methods 0.000 description 1
239000002700 tablet coating Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 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
- 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
- A61P9/08—Vasodilators for multiple indications

Landscapes

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

CA300,333A 1977-04-02 1978-04-03 Compose pharmaceutique , alkenyl xanthines contenues dans celui-ci et procede de preparation Expired CA1123435A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA363,133A CA1127083A (fr)	1977-04-02	1980-10-23	Compose pharmaceutique contenant de l'alkenyl xanthine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2714953.7		1977-04-02
DE2714953A DE2714953C2 (de)	1977-04-02	1977-04-02	Arzneimittel

Publications (1)

Publication Number	Publication Date
CA1123435A true CA1123435A (fr)	1982-05-11

Family

ID=6005579

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA300,333A Expired CA1123435A (fr)	1977-04-02	1978-04-03	Compose pharmaceutique , alkenyl xanthines contenues dans celui-ci et procede de preparation

Country Status (11)

Country	Link
JP (1)	JPS53149998A (fr)
AU (1)	AU523125B2 (fr)
BE (1)	BE865601A (fr)
CA (1)	CA1123435A (fr)
CH (1)	CH639849A5 (fr)
DE (1)	DE2714953C2 (fr)
FR (1)	FR2420346A1 (fr)
GB (1)	GB1580782A (fr)
IT (1)	IT1094052B (fr)
NL (1)	NL188620C (fr)
ZA (1)	ZA781876B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH654008A5 (fr) *	1979-05-22	1986-01-31	Nestle Sa	Procede de preparation de 1,3,7-trialkylxanthines.
DE2929596A1 (de) *	1979-07-21	1981-02-05	Hoechst Ag	Verfahren zur herstellung von oxoalkyl-xanthinen
GB8826595D0 (en) *	1988-11-14	1988-12-21	Beecham Wuelfing Gmbh & Co Kg	Active compounds
GB9312853D0 (en)	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5922751A (en)	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
US5591776A (en)	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
EP0799040B1 (fr)	1994-12-13	2003-08-20	Euroceltique S.A.	Thioxanthines trisubstituees
JPH10508032A (ja) *	1994-12-13	1998-08-04	ユーロ−セルティーク，エス．エイ．	アリールチオキサンチン類
US6166041A (en)	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6075016A (en)	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US5864037A (en)	1996-06-06	1999-01-26	Euro-Celtique, S.A.	Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH88833A (de) *	1920-06-22	1921-08-01	Hoffmann La Roche	Verfahren zur Darstellung von 1-Allyl-3-7-dimethylxanthin.
CH97978A (de) *	1921-10-07	1923-02-16	Chem Ind Basel	Verfahren zur Darstellung von Diallylxanthin.
CH97979A (de) *	1921-10-07	1923-02-16	Chem Ind Basel	Verfahren zur Darstellung von Triallylxanthin.
US2673848A (en) *	1951-12-29	1954-03-30	Searle & Co	3-alkenylxanthines and their lower 1-alkyl derivatives
DE2432702C2 (de) *	1974-07-08	1983-01-20	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Hydroxyalkylxanthinen

1977
- 1977-04-02 DE DE2714953A patent/DE2714953C2/de not_active Expired
1978
- 1978-03-31 CH CH344878A patent/CH639849A5/de not_active IP Right Cessation
- 1978-03-31 GB GB12728/78A patent/GB1580782A/en not_active Expired
- 1978-03-31 FR FR7809399A patent/FR2420346A1/fr active Granted
- 1978-03-31 JP JP3692178A patent/JPS53149998A/ja active Granted
- 1978-03-31 NL NLAANVRAGE7803504,A patent/NL188620C/xx not_active IP Right Cessation
- 1978-03-31 BE BE186498A patent/BE865601A/fr not_active IP Right Cessation
- 1978-03-31 IT IT21900/78A patent/IT1094052B/it active
- 1978-04-03 ZA ZA00781876A patent/ZA781876B/xx unknown
- 1978-04-03 CA CA300,333A patent/CA1123435A/fr not_active Expired
- 1978-04-03 AU AU34672/78A patent/AU523125B2/en not_active Expired

Also Published As

Publication number	Publication date
CH639849A5 (en)	1983-12-15
IT7821900A0 (it)	1978-03-31
NL188620B (nl)	1992-03-16
JPS53149998A (en)	1978-12-27
DE2714953A1 (de)	1979-02-01
BE865601A (fr)	1978-10-02
JPS5649886B2 (fr)	1981-11-25
DE2714953C2 (de)	1986-09-25
AU3467278A (en)	1979-10-11
GB1580782A (en)	1980-12-03
FR2420346A1 (fr)	1979-10-19
ZA781876B (en)	1979-06-27
NL188620C (nl)	1992-08-17
NL7803504A (nl)	1978-10-04
AU523125B2 (en)	1982-07-15
IT1094052B (it)	1985-07-26
FR2420346B1 (fr)	1983-05-27

Legal Events

Date	Code	Title	Description
1999-05-11	MKEX	Expiry

Publication	Publication Date	Title
US6180791B1 (en)	2001-01-30	Synthesis of 8-substituted xanthines
US4289776A (en)	1981-09-15	Xanthine derivatives
US4515795A (en)	1985-05-07	Pharmaceutical compositions
DE69130869T2 (de)	1999-06-10	Xanthinderivate
US4299834A (en)	1981-11-10	8-Phenyl-purines and pharmaceutical compositions containing same
HU180219B (en)	1983-02-28	Process for producing substituted xantine derivatives and salts
EP0198456B1 (fr)	1992-06-10	Dérivés de la 1,7-naphtyridine et préparations médicales les contenant
JPH0780882B2 (ja)	1995-08-30	６‐チオキサンチン誘導体
KR930001835B1 (ko)	1993-03-15	신규 히단토인(Hydantoin) 유도체의 제조방법
DE68925270T2 (de)	1996-06-13	Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel
EP0008802B1 (fr)	1982-07-21	Dérivés d'ergoline, leur préparation et composition thérapeutique les contenant
JPH05310731A (ja)	1993-11-22	イミダゾール−５−カルボン酸誘導体の新規なアシラール、それらの製造方法及び利用方法
GB1580782A (en)	1980-12-03	Pharmaceutical compositions alkenyl xanthines contained therein and processes for their preparation
US4960773A (en)	1990-10-02	Xanthine derivatives
DE2931418C2 (fr)	1989-06-29
JPH0222075B2 (fr)	1990-05-17
IE48073B1 (en)	1984-09-19	Substituted 2-phenylimino-imidazolidines
EP0038784A2 (fr)	1981-10-28	3,8-Dialkylxanthines, procédés pour leur préparation et compositions les contenant
Miller et al.	1939	Substituted sulfanilamides. I. N4-acyl derivatives
IE43711B1 (en)	1981-05-06	N-propargyl-2-phenylamino-2-imidazolines
EP0012925B1 (fr)	1982-11-10	Dérivés d'acide quinoléinonecarboxylique, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4085214A (en)	1978-04-18	Stable pro-drug forms of theophylline
US4207321A (en)	1980-06-10	Pharmaceutical compositions containing xanthines
IL44056A (en)	1977-01-31	Theophylline-acetate salts of isoquinoline derivatives,their preparation and pharmaceutical compositions containing them
US3975524A (en)	1976-08-17	3-Piperazino-isoquinolines and salts thereof