FI62089C - Foerfarande foer framstaellning av pao det perifera blodomloppet verkande 7-(n-(3-fenoxi-2-hydroxipropyl)-n-amino)-1,3-dialkyl-xantinderivat - Google Patents
Foerfarande foer framstaellning av pao det perifera blodomloppet verkande 7-(n-(3-fenoxi-2-hydroxipropyl)-n-amino)-1,3-dialkyl-xantinderivat Download PDFInfo
- Publication number
- FI62089C FI62089C FI753543A FI753543A FI62089C FI 62089 C FI62089 C FI 62089C FI 753543 A FI753543 A FI 753543A FI 753543 A FI753543 A FI 753543A FI 62089 C FI62089 C FI 62089C
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- hydroxy
- formula
- propyl
- benzyloxyphenoxy
- Prior art date
Links
- 230000002093 peripheral effect Effects 0.000 title claims 2
- -1 3-phenoxy-2-hydroxypropyl Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 238000007342 radical addition reaction Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 230000006378 damage Effects 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 208000014674 injury Diseases 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229960000278 theophylline Drugs 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 238000010171 animal model Methods 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
- 239000013078 crystal Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003836 peripheral circulation Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 208000037974 severe injury Diseases 0.000 description 3
- 230000009528 severe injury Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229960003279 thiopental Drugs 0.000 description 3
- ZCADXUUSKDASMN-UHFFFAOYSA-N 1,3-diethyl-7-[2-[[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]-methylamino]ethyl]purine-2,6-dione;hydrochloride Chemical compound Cl.C1=2C(=O)N(CC)C(=O)N(CC)C=2N=CN1CCN(C)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 ZCADXUUSKDASMN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229940075420 xanthine Drugs 0.000 description 2
- BSVSQZYFGBKAFJ-UHFFFAOYSA-N 1,3-diethyl-7-[2-(methylamino)ethyl]purine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CC)C2=C1N(CCNC)C=N2 BSVSQZYFGBKAFJ-UHFFFAOYSA-N 0.000 description 1
- ZFDICOQGZFUKNO-UHFFFAOYSA-N 1-(methylamino)-3-(2-phenylmethoxyphenoxy)propan-2-ol Chemical compound C(C1=CC=CC=C1)OC1=C(OCC(CNC)O)C=CC=C1 ZFDICOQGZFUKNO-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- ZZWGXGHWFOTKNP-UHFFFAOYSA-N 7-(2-bromoethyl)-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCBr)C=N2 ZZWGXGHWFOTKNP-UHFFFAOYSA-N 0.000 description 1
- ZALZLOKXTMWBPN-UHFFFAOYSA-N 7-[2-(N-[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]anilino)ethyl]-1,3-dimethylpurine-2,6-dione hydrochloride Chemical compound Cl.C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCN(C=1C=CC=CC=1)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 ZALZLOKXTMWBPN-UHFFFAOYSA-N 0.000 description 1
- ZSAKSOSOYSLMDH-UHFFFAOYSA-N 7-[2-[butyl-[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]amino]ethyl]-1,3-dimethylpurine-2,6-dione;hydrochloride Chemical compound Cl.C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(CCCC)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 ZSAKSOSOYSLMDH-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- PDVPLLNUWRQQMB-UHFFFAOYSA-N [Na].C(C)C1(C(NC(N(C1=O)CCCC)=S)=O)C Chemical compound [Na].C(C)C1(C(NC(N(C1=O)CCCC)=S)=O)C PDVPLLNUWRQQMB-UHFFFAOYSA-N 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure 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
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742460929 DE2460929A1 (de) | 1974-12-21 | 1974-12-21 | Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung |
| DE2460929 | 1974-12-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI753543A7 FI753543A7 (is") | 1976-06-22 |
| FI62089B FI62089B (fi) | 1982-07-30 |
| FI62089C true FI62089C (fi) | 1982-11-10 |
Family
ID=5934312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753543A FI62089C (fi) | 1974-12-21 | 1975-12-16 | Foerfarande foer framstaellning av pao det perifera blodomloppet verkande 7-(n-(3-fenoxi-2-hydroxipropyl)-n-amino)-1,3-dialkyl-xantinderivat |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3998953A (is") |
| JP (1) | JPS5188995A (is") |
| AT (1) | AT341540B (is") |
| AU (1) | AU501889B2 (is") |
| BE (1) | BE836898A (is") |
| BG (1) | BG25518A3 (is") |
| CA (1) | CA1036159A (is") |
| CH (1) | CH628346A5 (is") |
| CS (1) | CS191289B2 (is") |
| DD (1) | DD124984A5 (is") |
| DE (1) | DE2460929A1 (is") |
| DK (1) | DK137677C (is") |
| ES (2) | ES443738A1 (is") |
| FI (1) | FI62089C (is") |
| FR (1) | FR2294706A1 (is") |
| GB (1) | GB1517710A (is") |
| GR (1) | GR59204B (is") |
| HU (1) | HU174673B (is") |
| IE (1) | IE43208B1 (is") |
| IL (1) | IL48697A (is") |
| LU (1) | LU73972A1 (is") |
| NL (1) | NL7514837A (is") |
| NO (1) | NO144928C (is") |
| NZ (1) | NZ179599A (is") |
| PH (1) | PH11810A (is") |
| PL (1) | PL99165B1 (is") |
| RO (1) | RO68381A (is") |
| SE (1) | SE420493B (is") |
| SU (1) | SU603340A3 (is") |
| YU (1) | YU39004B (is") |
| ZA (1) | ZA757865B (is") |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337254A (en) * | 1977-08-23 | 1982-06-29 | Burroughs Wellcome Co. | Pharmaceutical compositions |
| DE3113880A1 (de) * | 1981-04-07 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von coffein |
| IT1174773B (it) * | 1983-07-29 | 1987-07-01 | Medosan Ind Biochimi | Attivita' antiaggregante piastrinica e broncolitica della 7-(1-metil-5-p-metilbenzoilpirrol-2-acetamidoetil)teofillina |
| US5736528A (en) * | 1993-10-28 | 1998-04-07 | University Of Florida Research Foundation, Inc. | N6 -(epoxynorborn-2-yl) adenosines as A1 adenosine receptor agonists |
| US5446046A (en) * | 1993-10-28 | 1995-08-29 | University Of Florida Research Foundation | A1 adenosine receptor agonists and antagonists as diuretics |
| US5620676A (en) * | 1994-03-08 | 1997-04-15 | The United States Of America As Represented By The Department Of Health And Human Services | Biologically active ATP analogs |
| US5789416B1 (en) * | 1996-08-27 | 1999-10-05 | Cv Therapeutics Inc | N6 mono heterocyclic substituted adenosine derivatives |
| WO1999031101A1 (en) * | 1997-12-17 | 1999-06-24 | University Of South Florida | Adenosine receptor antagonists with improved bioactivity |
| US6576619B2 (en) | 1999-05-24 | 2003-06-10 | Cv Therapeutics, Inc. | Orally active A1 adenosine receptor agonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1230663A (is") * | 1968-12-10 | 1971-05-05 | ||
| US3728346A (en) * | 1971-07-16 | 1973-04-17 | Degussa | Hydroxyphenylhydroxyalkylaminoalkyltheophyllines |
| JPS5132638B2 (is") * | 1972-07-13 | 1976-09-14 |
-
1974
- 1974-12-21 DE DE19742460929 patent/DE2460929A1/de active Granted
-
1975
- 1975-11-28 AT AT904575A patent/AT341540B/de not_active IP Right Cessation
- 1975-12-09 LU LU73972A patent/LU73972A1/xx unknown
- 1975-12-11 SU SU752197999A patent/SU603340A3/ru active
- 1975-12-12 DD DD190116A patent/DD124984A5/xx unknown
- 1975-12-15 AU AU87547/75A patent/AU501889B2/en not_active Expired
- 1975-12-16 DK DK571875A patent/DK137677C/da active
- 1975-12-16 FI FI753543A patent/FI62089C/fi not_active IP Right Cessation
- 1975-12-17 US US05/641,550 patent/US3998953A/en not_active Expired - Lifetime
- 1975-12-17 GR GR49628A patent/GR59204B/el unknown
- 1975-12-18 CH CH1643275A patent/CH628346A5/de not_active IP Right Cessation
- 1975-12-18 YU YU03234/75A patent/YU39004B/xx unknown
- 1975-12-18 CS CS758669A patent/CS191289B2/cs unknown
- 1975-12-18 RO RO7584245A patent/RO68381A/ro unknown
- 1975-12-19 FR FR7539174A patent/FR2294706A1/fr active Granted
- 1975-12-19 IL IL48697A patent/IL48697A/xx unknown
- 1975-12-19 GB GB52168/75A patent/GB1517710A/en not_active Expired
- 1975-12-19 SE SE7514477A patent/SE420493B/xx not_active IP Right Cessation
- 1975-12-19 PH PH17894A patent/PH11810A/en unknown
- 1975-12-19 NL NL7514837A patent/NL7514837A/xx not_active Application Discontinuation
- 1975-12-19 BE BE162965A patent/BE836898A/xx not_active IP Right Cessation
- 1975-12-19 HU HU75BO1590A patent/HU174673B/hu unknown
- 1975-12-19 IE IE2787/75A patent/IE43208B1/en unknown
- 1975-12-19 NZ NZ179599A patent/NZ179599A/xx unknown
- 1975-12-19 CA CA242,131A patent/CA1036159A/en not_active Expired
- 1975-12-19 ZA ZA757865A patent/ZA757865B/xx unknown
- 1975-12-19 NO NO754317A patent/NO144928C/no unknown
- 1975-12-19 JP JP50151721A patent/JPS5188995A/ja active Pending
- 1975-12-19 BG BG032887A patent/BG25518A3/xx unknown
- 1975-12-20 ES ES443738A patent/ES443738A1/es not_active Expired
- 1975-12-20 PL PL1975185740A patent/PL99165B1/pl unknown
-
1976
- 1976-09-11 ES ES451457A patent/ES451457A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |