GB1561005A - Xanthine compounds and method of treating bronchospastic and allergic diseases - Google Patents
Xanthine compounds and method of treating bronchospastic and allergic diseases Download PDFInfo
- Publication number
- GB1561005A GB1561005A GB12923/77A GB1292377A GB1561005A GB 1561005 A GB1561005 A GB 1561005A GB 12923/77 A GB12923/77 A GB 12923/77A GB 1292377 A GB1292377 A GB 1292377A GB 1561005 A GB1561005 A GB 1561005A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- butyl
- compound according
- dimethyl
- alkyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 22
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title description 85
- 239000004044 bronchoconstricting agent Substances 0.000 title description 12
- 230000002741 bronchospastic effect Effects 0.000 title description 12
- 208000026935 allergic disease Diseases 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 96
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
- -1 alkyl chloroformate Chemical compound 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000003826 tablet Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 230000007883 bronchodilation Effects 0.000 claims description 10
- MTBUJUHRXVGLEF-UHFFFAOYSA-N 1,8-dimethyl-3-(2-methylbutyl)-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1NC(C)=N2 MTBUJUHRXVGLEF-UHFFFAOYSA-N 0.000 claims description 9
- 239000000443 aerosol Substances 0.000 claims description 9
- IVSIEJNJCOMQOI-UHFFFAOYSA-N methyl 1,8-dimethyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1N(C(=O)OC)C(C)=N2 IVSIEJNJCOMQOI-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 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 description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 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
- 239000003380 propellant Substances 0.000 claims description 5
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- JGULMIZILIGJNC-UHFFFAOYSA-N 1,8-dimethyl-3-(2-methylpropyl)-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1NC(C)=N2 JGULMIZILIGJNC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000006190 sub-lingual tablet Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- UYHDLISIVNPBSN-UHFFFAOYSA-N methyl 1-methyl-3-(2-methylbutyl)-2,6-dioxopurine-7-carboxylate Chemical compound O=C1N(C)C(=O)N(CC(C)CC)C2=C1N(C(=O)OC)C=N2 UYHDLISIVNPBSN-UHFFFAOYSA-N 0.000 claims 1
- 229940098466 sublingual tablet Drugs 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 41
- 230000000694 effects Effects 0.000 description 37
- 229940075420 xanthine Drugs 0.000 description 31
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
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- 230000001665 lethal effect Effects 0.000 description 20
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- 229940124630 bronchodilator Drugs 0.000 description 19
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- 231100000518 lethal Toxicity 0.000 description 18
- 150000004702 methyl esters Chemical class 0.000 description 18
- 229960000278 theophylline Drugs 0.000 description 15
- 239000000168 bronchodilator agent Substances 0.000 description 14
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 11
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- 230000003266 anti-allergic effect Effects 0.000 description 6
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 5
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 5
- 229930182837 (R)-adrenaline Natural products 0.000 description 5
- GEZKBQOIOUAYLL-UHFFFAOYSA-N 1-methyl-3-(2-methylbutyl)urea Chemical compound CCC(C)CNC(=O)NC GEZKBQOIOUAYLL-UHFFFAOYSA-N 0.000 description 5
- 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 5
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- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
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- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
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- GILKHXWWPFDEDK-UHFFFAOYSA-N N1C(=O)NC=2N=CNC2C1=O.N1C(=O)NC=2N=CN(C2C1=O)C(=O)O Chemical compound N1C(=O)NC=2N=CNC2C1=O.N1C(=O)NC=2N=CN(C2C1=O)C(=O)O GILKHXWWPFDEDK-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 101000889463 Rattus norvegicus Trefoil factor 2 Proteins 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 229920001615 Tragacanth Polymers 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000420 anogeissus latifolia wall. gum Substances 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000019314 gum ghatti Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003453 histamine agonist Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- HVIXICZZLUIYOZ-UHFFFAOYSA-N methyl 1,8-dimethyl-3-(2-methylpropyl)-2,6-dioxopurine-7-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2C(=O)OC HVIXICZZLUIYOZ-UHFFFAOYSA-N 0.000 description 1
- DDLDPZOPKXVLGD-UHFFFAOYSA-N methyl 2,6-dioxo-3,7-dihydropurine-8-carboxylate Chemical compound N1C(=O)NC(=O)C2=C1N=C(C(=O)OC)N2 DDLDPZOPKXVLGD-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N n-pentylamine Natural products CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000001533 respiratory mucosa Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- VRZJGNXBSRQZGM-UHFFFAOYSA-N xanthine-8-carboxylic acid Chemical compound N1C(=O)NC(=O)C2=C1N=C(C(=O)O)N2 VRZJGNXBSRQZGM-UHFFFAOYSA-N 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/672,388 US4120947A (en) | 1976-03-31 | 1976-03-31 | Xanthine compounds and method of treating bronchospastic and allergic diseases |
| US05/672,437 US4089959A (en) | 1976-03-31 | 1976-03-31 | Long-acting xanthine bronchodilators and antiallergy agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561005A true GB1561005A (en) | 1980-02-13 |
Family
ID=27100746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12923/77A Expired GB1561005A (en) | 1976-03-31 | 1977-03-28 | Xanthine compounds and method of treating bronchospastic and allergic diseases |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS52122396A (cs) |
| CA (1) | CA1077932A (cs) |
| DE (1) | DE2713389A1 (cs) |
| FR (1) | FR2346353A1 (cs) |
| GB (1) | GB1561005A (cs) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469698A (en) * | 1980-05-02 | 1984-09-04 | Societe D'assistance Technique Pour Produits Nestle S.A. | Di- or trisubstituted xanthines with neuroleptic properties and composition |
| US5864037A (en) | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| US5889014A (en) | 1994-10-12 | 1999-03-30 | Euro-Celtique, S.A. | Heterocyclic compounds for inhibiting phosphodiesterase IV |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US5939422A (en) | 1993-06-22 | 1999-08-17 | Euro-Celtique, S.A. | Chemical compounds having PDE-IV inhibition activity |
| US5977119A (en) | 1994-12-13 | 1999-11-02 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| US6066641A (en) | 1994-12-13 | 2000-05-23 | Euro-Celtique S.A. | Aryl thioxanthines |
| US6075016A (en) | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
| 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 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416810C (sv) * | 1977-10-14 | 1982-07-19 | Draco Ab | Forfarande for framstellning av xantinderivat med antiallergisk aktivitet |
| SE7810946L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | Metod att behandla kronisk obstruktiv luftvegssjukdom |
| SE7810947L (sv) * | 1978-10-20 | 1980-04-21 | Draco Ab | 3-alkylxanthines |
| SE8002910L (sv) * | 1980-04-18 | 1981-10-19 | Draco Ab | 3,8-dialkylxantiner, forfarande for deras framstellning, beredning och metoder for behandling av kronisk obstruktiv luftvegssjukdom och kardiovaskulera sjukdomar |
| FR2611716A1 (fr) * | 1987-03-06 | 1988-09-09 | Uriach Cia Sa J | Derives de diisobutylxanthine substituee en position 7 utiles comme bronchodilatateurs, procede pour leur preparation et composition pharmaceutique les contenant |
| US5321029A (en) * | 1988-11-14 | 1994-06-14 | Beecham-Wuelfing Gmbh & Co.K.G. | Xanthines |
| GB8826595D0 (en) * | 1988-11-14 | 1988-12-21 | Beecham Wuelfing Gmbh & Co Kg | Active compounds |
| IT1229195B (it) * | 1989-03-10 | 1991-07-25 | Poli Ind Chimica Spa | Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2729643A (en) * | 1956-01-03 | J-disubstmjied and i |
-
1977
- 1977-03-22 CA CA274,520A patent/CA1077932A/en not_active Expired
- 1977-03-23 DE DE19772713389 patent/DE2713389A1/de active Granted
- 1977-03-28 GB GB12923/77A patent/GB1561005A/en not_active Expired
- 1977-03-31 JP JP3555977A patent/JPS52122396A/ja active Granted
- 1977-03-31 FR FR7709680A patent/FR2346353A1/fr active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469698A (en) * | 1980-05-02 | 1984-09-04 | Societe D'assistance Technique Pour Produits Nestle S.A. | Di- or trisubstituted xanthines with neuroleptic properties and composition |
| US4581451A (en) * | 1980-05-02 | 1986-04-08 | Nestec S.A. | Preparation of di- and tri-substituted xanthine compounds |
| US5939422A (en) | 1993-06-22 | 1999-08-17 | Euro-Celtique, S.A. | Chemical compounds having PDE-IV inhibition activity |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US5889014A (en) | 1994-10-12 | 1999-03-30 | Euro-Celtique, S.A. | Heterocyclic compounds for inhibiting phosphodiesterase IV |
| US5977119A (en) | 1994-12-13 | 1999-11-02 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| US6066641A (en) | 1994-12-13 | 2000-05-23 | Euro-Celtique S.A. | Aryl thioxanthines |
| US6090816A (en) * | 1994-12-13 | 2000-07-18 | Euro-Celtique S.A. | Aryl thioxanthines |
| 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 |
| US6310205B1 (en) | 1996-06-06 | 2001-10-30 | Euro-Celtique, S.A. | Hypoxathine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2713389A1 (de) | 1977-10-13 |
| FR2346353B1 (cs) | 1980-03-07 |
| DE2713389C2 (cs) | 1992-03-19 |
| JPS52122396A (en) | 1977-10-14 |
| FR2346353A1 (fr) | 1977-10-28 |
| CA1077932A (en) | 1980-05-20 |
| JPS5720313B2 (cs) | 1982-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960328 |