FI69465B - Foerfarande foer framstaellning av farmakologiskt aktiva 3,8-dialkylxantiner - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva 3,8-dialkylxantiner Download PDFInfo
- Publication number
- FI69465B FI69465B FI811212A FI811212A FI69465B FI 69465 B FI69465 B FI 69465B FI 811212 A FI811212 A FI 811212A FI 811212 A FI811212 A FI 811212A FI 69465 B FI69465 B FI 69465B
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- dihydro
- purine
- dione
- propyl
- Prior art date
Links
- 230000000144 pharmacologic effect Effects 0.000 title description 4
- 235000013399 edible fruits Nutrition 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims abstract description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
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- -1 2.2 -dimethylpropyl Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
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- 229940075420 xanthine Drugs 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- WDLAKCAOEKLEIV-UHFFFAOYSA-N 3-cyclobutyl-8-ethyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)C=2NC(CC)=NC=2N1C1CCC1 WDLAKCAOEKLEIV-UHFFFAOYSA-N 0.000 description 1
- DZXAEJCKQAXDGM-UHFFFAOYSA-N 3-cyclopentyl-8-ethyl-7H-purine-2,6-dione Chemical compound C1(CCCC1)N1C(NC(C=2NC(=NC12)CC)=O)=O DZXAEJCKQAXDGM-UHFFFAOYSA-N 0.000 description 1
- SAHWVZACGUPTQJ-UHFFFAOYSA-N 3-cyclopropyl-8-ethyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)C=2NC(CC)=NC=2N1C1CC1 SAHWVZACGUPTQJ-UHFFFAOYSA-N 0.000 description 1
- QDHPVYJXCHOBBC-UHFFFAOYSA-N 6-amino-1-ethyl-5-nitropyrimidine-2,4-dione Chemical compound CCN1C(N)=C([N+]([O-])=O)C(=O)NC1=O QDHPVYJXCHOBBC-UHFFFAOYSA-N 0.000 description 1
- PDKNBSLTBPMRHQ-UHFFFAOYSA-N 8-(2-methylpropyl)-3-propyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCC)C2=C1NC(CC(C)C)=N2 PDKNBSLTBPMRHQ-UHFFFAOYSA-N 0.000 description 1
- GGOSLMWKWVWOCQ-UHFFFAOYSA-N 8-cyclopropyl-3-propyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)NC(=O)N(CCC)C=2N=C1C1CC1 GGOSLMWKWVWOCQ-UHFFFAOYSA-N 0.000 description 1
- MXNWQDSTCBTICY-UHFFFAOYSA-N 8-ethyl-3-pentyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCCC)C2=C1NC(CC)=N2 MXNWQDSTCBTICY-UHFFFAOYSA-N 0.000 description 1
- 244000208874 Althaea officinalis Species 0.000 description 1
- 235000006576 Althaea officinalis Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- PUYGPBSOFXYHMH-UHFFFAOYSA-N C(C)C1N=C2N(CNC=C2N1)CCC Chemical compound C(C)C1N=C2N(CNC=C2N1)CCC PUYGPBSOFXYHMH-UHFFFAOYSA-N 0.000 description 1
- SWGZKGJCCFYJSJ-UHFFFAOYSA-N C(C)C1N=C2N(CNC=C2N1)CCCCC Chemical compound C(C)C1N=C2N(CNC=C2N1)CCCCC SWGZKGJCCFYJSJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical class [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- RYXPMWYHEBGTRV-UHFFFAOYSA-N Omeprazole sodium Chemical compound [Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RYXPMWYHEBGTRV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000277284 Salvelinus fontinalis Species 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- 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 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000007211 cardiovascular event Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000007911 effervescent powder Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000001035 marshmallow Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (4)
1. Förfarande för framstä lining av en f arinako logiskt aktiv förening med formeln il H HN^C\C^ N\ I II C-R2 (I)
0 R1 eller ett fysiologiskt acceptabelt sait därav, i vilken formel 1 R är en etyl-, n-propyl-, n-butyl-, isobutyl-, n-pentyl-, 2-metylbutyl-, 3-metylbutyl-, 2,2-dimetylpropyl-, cyklopropyl-, 2 cyklobutyl-, cyklopentyl- eller cyklohexylmetylgrupp och R är en metyl-, etyl-, n-propyl-, isopropyl-, cyklopropyl-, n-butyl-, isobutyl-, tert.butyl- eller cyklobutylgrupp förutsatt 1 2 att R är en etylgrupp dl R är en metylgrupp, k ä n n e -tecknat av att en förening med formeln /C X HN C-NH, I II 2 0^C'-N-C-NH2 R1 omsättes med en förening med formeln R2-X 1 2 van R och R har ovan angiven betydelse och X är -C00H, -C0NH„ 2. eller -OC-O-CO-R , och vid behov dehydratiseras den erhallna produkten, varefter, om sl önskas, den erhlllna föreningen om- vandlas ti]1 ett fysiologiskt acceptabelt sait.
2. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln P h il n ^CX N HN c \ I li C-CH3 ^c^n^c.xN^·
0 I C2H5
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8002910 | 1980-04-18 | ||
| SE8002910A SE8002910L (sv) | 1980-04-18 | 1980-04-18 | 3,8-dialkylxantiner, forfarande for deras framstellning, beredning och metoder for behandling av kronisk obstruktiv luftvegssjukdom och kardiovaskulera sjukdomar |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI811212L FI811212L (fi) | 1981-10-19 |
| FI69465B true FI69465B (fi) | 1985-10-31 |
| FI69465C FI69465C (fi) | 1986-02-10 |
Family
ID=20340763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI811212A FI69465C (fi) | 1980-04-18 | 1981-04-16 | Foerfarande foer framstaellning av farmakologiskt aktiva 3,8-dialkylxantiner |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4546182A (sv) |
| EP (1) | EP0038784B1 (sv) |
| JP (1) | JPS56166191A (sv) |
| AT (1) | ATE10099T1 (sv) |
| AU (1) | AU543122B2 (sv) |
| CA (1) | CA1156229A (sv) |
| DD (1) | DD158400A5 (sv) |
| DE (1) | DE3166893D1 (sv) |
| DK (1) | DK151631B (sv) |
| ES (1) | ES8203088A1 (sv) |
| FI (1) | FI69465C (sv) |
| GR (1) | GR82347B (sv) |
| HU (1) | HU185254B (sv) |
| IE (1) | IE51106B1 (sv) |
| NO (1) | NO811161L (sv) |
| NZ (1) | NZ196829A (sv) |
| PH (1) | PH16264A (sv) |
| PL (1) | PL134762B1 (sv) |
| PT (1) | PT72881B (sv) |
| SE (1) | SE8002910L (sv) |
| ZA (1) | ZA811729B (sv) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7810947L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | 3-alkylxanthines |
| US4710503A (en) * | 1985-02-07 | 1987-12-01 | Euroceltique S.A. | 6-thioxanthine derivatives |
| GB8618931D0 (en) * | 1986-08-02 | 1986-09-10 | Euro Celtique Sa | 6-thioxanthines |
| US5298508A (en) * | 1988-07-19 | 1994-03-29 | The United States Of America As Represented By The Department Of Health And Human Services | Irreversible inhibitors of adenosine receptors |
| JP2843634B2 (ja) * | 1989-03-06 | 1999-01-06 | 協和醗酵工業株式会社 | キサンチン誘導体 |
| IT1229195B (it) * | 1989-03-10 | 1991-07-25 | Poli Ind Chimica Spa | Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche. |
| WO1990012797A1 (en) * | 1989-04-19 | 1990-11-01 | The United States Of America, As Represented By The Secretary, U.S. Department Of Commerce | Sulfer-containing xanthine derivatives as adenosin antagonists |
| CA2030112A1 (en) * | 1989-11-24 | 1991-05-25 | Yasuo Ito | Xanthine compound, method for preparing thereof, and a pharmaceutical composition comprising the same |
| US5366977A (en) * | 1992-09-29 | 1994-11-22 | The United States Of America, As Represented By The Department Of Health And Human Services | Method of treating cystic fibrosis using 8-cyclopentyl-1,3-dipropylxanthine or xanthine amino congeners |
| DE4311538C1 (de) * | 1993-04-07 | 1994-10-06 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von 1,3-Dimethyl-4,5-diaminouracil |
| WO1994025462A1 (en) * | 1993-05-03 | 1994-11-10 | The United States Of America, Represented By The | 8-substituted 1,3,7-trialkyl-xanthine derivatives as a2-selective adenosine receptor antagonists |
| US6316423B1 (en) | 1996-04-10 | 2001-11-13 | The United States Of America As Represented By The Departmant Of Health And Human Services | Method of treating ischemic, hypoxic and anoxic brain damage |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53890B2 (sv) * | 1972-04-22 | 1978-01-12 | ||
| CA1077932A (en) * | 1976-03-31 | 1980-05-20 | Berlex Laboratories, Inc. | Xanthine compounds and method of treating bronchospastic and allergic diseases |
| US4089959A (en) * | 1976-03-31 | 1978-05-16 | Cooper Laboratories, Inc. | Long-acting xanthine bronchodilators and antiallergy agents |
| SE416810C (sv) * | 1977-10-14 | 1982-07-19 | Draco Ab | Forfarande for framstellning av xantinderivat med antiallergisk aktivitet |
| SE7810947L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | 3-alkylxanthines |
| SE7810946L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | Metod att behandla kronisk obstruktiv luftvegssjukdom |
-
1980
- 1980-04-18 SE SE8002910A patent/SE8002910L/sv not_active Application Discontinuation
-
1981
- 1981-03-09 EP EP81850039A patent/EP0038784B1/en not_active Expired
- 1981-03-09 AT AT81850039T patent/ATE10099T1/de not_active IP Right Cessation
- 1981-03-09 DE DE8181850039T patent/DE3166893D1/de not_active Expired
- 1981-03-16 ZA ZA00811729A patent/ZA811729B/xx unknown
- 1981-03-17 CA CA000373230A patent/CA1156229A/en not_active Expired
- 1981-04-01 PH PH25455A patent/PH16264A/en unknown
- 1981-04-03 NO NO811161A patent/NO811161L/no unknown
- 1981-04-08 IE IE769/81A patent/IE51106B1/en unknown
- 1981-04-14 DD DD81229229A patent/DD158400A5/de unknown
- 1981-04-14 DK DK168281AA patent/DK151631B/da active IP Right Grant
- 1981-04-15 ES ES501400A patent/ES8203088A1/es not_active Expired
- 1981-04-15 NZ NZ196829A patent/NZ196829A/en unknown
- 1981-04-15 AU AU69555/81A patent/AU543122B2/en not_active Ceased
- 1981-04-15 GR GR64702A patent/GR82347B/el unknown
- 1981-04-16 PT PT72881A patent/PT72881B/pt unknown
- 1981-04-16 FI FI811212A patent/FI69465C/fi not_active IP Right Cessation
- 1981-04-17 JP JP5724181A patent/JPS56166191A/ja active Pending
- 1981-04-17 PL PL1981230737A patent/PL134762B1/pl unknown
- 1981-04-17 HU HU811020A patent/HU185254B/hu unknown
-
1983
- 1983-08-16 US US06/523,731 patent/US4546182A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO811161L (no) | 1981-10-19 |
| AU6955581A (en) | 1981-10-22 |
| PL134762B1 (en) | 1985-09-30 |
| PL230737A1 (sv) | 1982-03-29 |
| JPS56166191A (en) | 1981-12-21 |
| ES501400A0 (es) | 1982-02-16 |
| NZ196829A (en) | 1984-12-14 |
| DE3166893D1 (en) | 1984-12-06 |
| DK151631B (da) | 1987-12-21 |
| PT72881A (en) | 1981-05-01 |
| HU185254B (en) | 1984-12-28 |
| IE51106B1 (en) | 1986-10-01 |
| EP0038784B1 (en) | 1984-10-31 |
| DD158400A5 (de) | 1983-01-12 |
| PT72881B (en) | 1983-03-29 |
| EP0038784A2 (en) | 1981-10-28 |
| ES8203088A1 (es) | 1982-02-16 |
| GR82347B (sv) | 1984-12-13 |
| AU543122B2 (en) | 1985-04-04 |
| PH16264A (en) | 1983-08-23 |
| SE8002910L (sv) | 1981-10-19 |
| FI811212L (fi) | 1981-10-19 |
| EP0038784A3 (en) | 1982-01-20 |
| FI69465C (fi) | 1986-02-10 |
| DK168281A (da) | 1981-10-19 |
| CA1156229A (en) | 1983-11-01 |
| ZA811729B (en) | 1982-04-28 |
| US4546182A (en) | 1985-10-08 |
| IE810796L (en) | 1981-10-18 |
| ATE10099T1 (de) | 1984-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AKTIEBOLAGET DRACO |