FR2480286A1 - Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique - Google Patents
Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2480286A1 FR2480286A1 FR8107075A FR8107075A FR2480286A1 FR 2480286 A1 FR2480286 A1 FR 2480286A1 FR 8107075 A FR8107075 A FR 8107075A FR 8107075 A FR8107075 A FR 8107075A FR 2480286 A1 FR2480286 A1 FR 2480286A1
- Authority
- FR
- France
- Prior art keywords
- radical
- formula
- oxygen atom
- dioxolane
- compound
- Prior art date
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- -1 RADICAL HYDROXY, BROMO, ACETOXY, PYRROLIDINO, MORPHOLINO, PIPERAZINO Chemical group 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 206010011224 Cough Diseases 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229960000278 theophylline Drugs 0.000 claims description 3
- AQHBMGQVRLBFLJ-UHFFFAOYSA-N 7-[[2-(bromomethyl)-1,3-dioxolan-4-yl]methyl]-1,3-dimethylpurine-2,6-dione Chemical group C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CC1COC(CBr)O1 AQHBMGQVRLBFLJ-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- HJHXEERFDKPWSL-UHFFFAOYSA-N [4-[(1,3-dimethyl-2,6-dioxopurin-7-yl)methyl]-1,3-dioxolan-2-yl]methyl acetate Chemical group O1C(COC(=O)C)OCC1CN1C(C(=O)N(C)C(=O)N2C)=C2N=C1 HJHXEERFDKPWSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- PASPNMNFZXXSGT-UHFFFAOYSA-N 1,3-dimethyl-7-[[4-(morpholin-4-ylmethyl)-1,3-dioxolan-2-yl]methyl]purine-2,6-dione Chemical group C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CC(O1)OCC1CN1CCOCC1 PASPNMNFZXXSGT-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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 7
- 238000011282 treatment Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 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 5
- 229960003556 aminophylline Drugs 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000037396 body weight Effects 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
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004862 dioxolanes Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- XHTFYQMWWPXKSO-UHFFFAOYSA-N 1,3-dioxolan-2-ylmethyl acetate Chemical class CC(=O)OCC1OCCO1 XHTFYQMWWPXKSO-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000004479 aerosol dispenser Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002562 anti-bronchospastic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21370/80A IT1195267B (it) | 1980-04-15 | 1980-04-15 | Derivati teofillinmetildiossolanici,procedimento per la loro preparazione e relative composizioni farmaceutiche |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2480286A1 true FR2480286A1 (fr) | 1981-10-16 |
| FR2480286B1 FR2480286B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-03-30 |
Family
ID=11180793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8107075A Granted FR2480286A1 (fr) | 1980-04-15 | 1981-04-08 | Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique |
Country Status (7)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075850A3 (en) * | 1981-09-26 | 1983-07-27 | Hoechst Aktiengesellschaft | Pharmaceutical preparations containing vicinal dihydroxyalkyl xanthines, process for the preparation of the xanthines and the appropriate intermediates |
| EP0089028A1 (de) * | 1982-03-12 | 1983-09-21 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung |
| EP0171005A3 (en) * | 1984-07-27 | 1987-04-15 | Boehringer Biochemia Robin S.P.A. | Xanthinylmethylthiazolidines, process for their preparation and pharmaceutical compositions containing them |
| EP0272596A3 (en) * | 1986-12-24 | 1990-03-28 | Istituto Biologico Chemioterapico "Abc" S.P.A. | Theophyllinemethyldithiolan and theophyllinemethyldithianyl derivates, a method for their preparation and pharmaceutical compositions in which they are included |
| EP0315401A3 (en) * | 1987-11-02 | 1991-01-16 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Xanthine derivatives and their preparation and pharmaceutical formulation |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2500277B2 (ja) * | 1990-11-27 | 1996-05-29 | 三井東圧化学株式会社 | フェノ―ル系樹脂パイプの押出成型方法および装置 |
| US5786360A (en) | 1996-11-19 | 1998-07-28 | Link Technology Incorporated | A1 adenosine receptor antagonists |
| CA2516250A1 (en) * | 2003-02-19 | 2004-09-02 | Endacea, Inc. | A1 adenosine receptor antagonists |
| EP1636229A4 (en) * | 2003-06-06 | 2008-07-30 | Endacea Inc | ADENOSINE A1 RECEPTOR ANTAGONISTS |
| CA2528367A1 (en) * | 2003-06-09 | 2004-12-23 | Endacea, Inc. | A1 adenosine receptor antagonists |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421614A1 (fr) * | 1978-04-06 | 1979-11-02 | Abc Ist Biolog Chem Spa | Composition pharmaceutique a base de 2-(7'-theophyllinomethyl)-1,3-dioxolane |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2761861A (en) * | 1953-09-11 | 1956-09-04 | Hoffmann La Roche | Process for the manufacture of novel xanthine bases and salts thereof |
| US2840559A (en) * | 1954-06-22 | 1958-06-24 | Krantz Jr | Nuclearly substituted 8-theophyllines and method of making the same |
| FR1523273A (fr) * | 1967-03-13 | 1968-05-03 | Soc Ind Fab Antibiotiques Sifa | Nouveaux dérivés de théophylline et procédé de préparation |
| ES377662A1 (es) * | 1969-03-28 | 1973-01-01 | Walter Bestian | Procedimiento para la preparacion de nuevos compuestos de derivados de dialcohil-xantina. |
-
1980
- 1980-04-15 IT IT21370/80A patent/IT1195267B/it active
-
1981
- 1981-04-06 US US06/251,485 patent/US4378359A/en not_active Expired - Fee Related
- 1981-04-08 DE DE19813114130 patent/DE3114130A1/de not_active Withdrawn
- 1981-04-08 FR FR8107075A patent/FR2480286A1/fr active Granted
- 1981-04-13 GB GB8111536A patent/GB2078717B/en not_active Expired
- 1981-04-14 JP JP56056896A patent/JPS5827796B2/ja not_active Expired
- 1981-04-14 BE BE0/204481A patent/BE888417A/fr not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421614A1 (fr) * | 1978-04-06 | 1979-11-02 | Abc Ist Biolog Chem Spa | Composition pharmaceutique a base de 2-(7'-theophyllinomethyl)-1,3-dioxolane |
Non-Patent Citations (1)
| Title |
|---|
| CA1964 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075850A3 (en) * | 1981-09-26 | 1983-07-27 | Hoechst Aktiengesellschaft | Pharmaceutical preparations containing vicinal dihydroxyalkyl xanthines, process for the preparation of the xanthines and the appropriate intermediates |
| US4616020A (en) * | 1981-09-26 | 1986-10-07 | Hoechst Aktiengesellschaft | Medicaments, vicinal dihydroxyalkylxanthines contained therein, processes for the preparation of these xanthine compounds and intermediate products suitable for these |
| EP0089028A1 (de) * | 1982-03-12 | 1983-09-21 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung |
| EP0171005A3 (en) * | 1984-07-27 | 1987-04-15 | Boehringer Biochemia Robin S.P.A. | Xanthinylmethylthiazolidines, process for their preparation and pharmaceutical compositions containing them |
| EP0272596A3 (en) * | 1986-12-24 | 1990-03-28 | Istituto Biologico Chemioterapico "Abc" S.P.A. | Theophyllinemethyldithiolan and theophyllinemethyldithianyl derivates, a method for their preparation and pharmaceutical compositions in which they are included |
| EP0315401A3 (en) * | 1987-11-02 | 1991-01-16 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Xanthine derivatives and their preparation and pharmaceutical formulation |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8021370A0 (it) | 1980-04-15 |
| JPS56164191A (en) | 1981-12-17 |
| BE888417A (fr) | 1981-07-31 |
| IT1195267B (it) | 1988-10-12 |
| GB2078717A (en) | 1982-01-13 |
| GB2078717B (en) | 1984-02-15 |
| JPS5827796B2 (ja) | 1983-06-11 |
| FR2480286B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-03-30 |
| DE3114130A1 (de) | 1982-01-28 |
| US4378359A (en) | 1983-03-29 |
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