DE386683T1 - Xanthinderivate mit bronchodilatorischer aktivitaet, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. - Google Patents
Xanthinderivate mit bronchodilatorischer aktivitaet, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.Info
- Publication number
- DE386683T1 DE386683T1 DE199090104229T DE90104229T DE386683T1 DE 386683 T1 DE386683 T1 DE 386683T1 DE 199090104229 T DE199090104229 T DE 199090104229T DE 90104229 T DE90104229 T DE 90104229T DE 386683 T1 DE386683 T1 DE 386683T1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- compound according
- alkyl
- pharmaceutical compositions
- compounds
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title 1
- 230000003182 bronchodilatating effect Effects 0.000 title 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- DKPCSXFEWFSECE-UHFFFAOYSA-N 6-amino-5-nitrosopyrimidine-2,4-diol Chemical compound NC=1NC(=O)NC(=O)C=1N=O DKPCSXFEWFSECE-UHFFFAOYSA-N 0.000 claims 2
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- BBTNLADSUVOPPN-UHFFFAOYSA-N 5,6-diaminouracil Chemical compound NC=1NC(=O)NC(=O)C=1N BBTNLADSUVOPPN-UHFFFAOYSA-N 0.000 claims 1
- 208000009079 Bronchial Spasm Diseases 0.000 claims 1
- 208000014181 Bronchial disease Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 229940124630 bronchodilator Drugs 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000006196 drop Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- -1 methoxyethyl Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 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 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 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
-
- 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
-
- 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
-
- 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)
- 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)
Claims (12)
1. Verbindungen der allgemeinen Formel (I)
O &eegr;
(D
worin R1 H oder C1-C6-AIkYl, R2 C1-C6-AIkYl, C2-C6-Alkoxyalkyl,
C3-C6-Zykloakyl, C4-C7-Zykloakylmethyl,
R3 H, C1-C6-AIkYl, ein C4~C6 aliphatischer Zykloaminorest
mit einem oder mehreren Stickstoffatomen ist.
2. Verbindung nach Anspruch 1,
worin R1 = R3 = Wasserstoff und R2 = Zyklopropylmethyl
ist.
3. Verbindung nach Anspruch 1,
worin R1 = R3 = Wasserstoff und R2 = Methoxyethyl ist.
4. Verbindung nach Anspruch 1,
worin R1 = Wässerstoff, R2 = n-Propyl und R3 = 4-Methyl-piperazin-1-yl
ist.
5. Verbindung nach Anspruch 1,
worin R1 = R2 = n-Hexyl und R3 = Wasserstoff ist.
6. Verbindung nach Anspruch 1,
worin R1 = n-Pentyl, R2 = n-Propyl und R3 = Wasserstoff
ist.
7. Verbindung nach Anspruch 1,
worin R1 = R3 = Wasserstoff und R2 = Zyklopropyl ist.
8. Verfahren zur Herstellung der Verbindungen nach einem der Ansprüche 1-7,
dadurch gekennzeichnet, da/3
6-Aminourazil (II) durch organisches oder Natriumnitrit nitrosiert und das erhaltene 5-Nitroso-6-Aminourazil (III) mit Natriumdithionit reduziert wird um 5,6-Diaminourazil (IV) zu ergeben, welches schließlich mit Ameisensäure formyliert und mit Natriumhydroxid behandelt wird, um die Verbindung (I) zu ergeben.
6-Aminourazil (II) durch organisches oder Natriumnitrit nitrosiert und das erhaltene 5-Nitroso-6-Aminourazil (III) mit Natriumdithionit reduziert wird um 5,6-Diaminourazil (IV) zu ergeben, welches schließlich mit Ameisensäure formyliert und mit Natriumhydroxid behandelt wird, um die Verbindung (I) zu ergeben.
9. Pharmazeutische Zusammensetzungen mit bronchialerweiternder Wirksamkeit, die als Wirkstoff eine der
Verbindungen nach den Ansprüchen 1-7 enthalten in Vermischung mit einem pharmazeutisch zulässigen Träger.
10. Pharmazeutische Zusammensetzungen nach Anspruch 9 in Form von Tabletten, Gelatinekapseln, Puder, Sirup
und Tropfen zum innerlichen Gebrauch; lyophilisierte Ampullen und Lösungen für die parenterale Anwendung
und Zäpfchen für die rektale Anwendung.
11. Zusammensetzungen nach den Ansprüchen 1-7 zur Anwendung als therapeutische Wirkstoffe.
12. Verbindungen nach den Ansprüchen 1-7 zur Herstellung
von pharmazeutischen Zusammensetzungen für
die therapeutische Behandlung von Bronchialasthma und Bronchospasmus verbunden mit chronischer Bronchitis
und Emphysem.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8919730A IT1229195B (it) | 1989-03-10 | 1989-03-10 | Derivati xantinici ad attivita' broncodilatatrice e loro applicazioni terapeutiche. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE386683T1 true DE386683T1 (de) | 1991-02-07 |
Family
ID=11160729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE199090104229T Pending DE386683T1 (de) | 1989-03-10 | 1990-03-05 | Xanthinderivate mit bronchodilatorischer aktivitaet, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0386683A3 (de) |
| JP (1) | JPH03200787A (de) |
| DE (1) | DE386683T1 (de) |
| ES (1) | ES2017899A4 (de) |
| GR (1) | GR900300160T1 (de) |
| IT (1) | IT1229195B (de) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9020921D0 (en) * | 1990-09-26 | 1990-11-07 | Beecham Group Plc | Novel compounds |
| GB9210839D0 (en) * | 1992-05-21 | 1992-07-08 | Smithkline Beecham Plc | Novel compounds |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US5591776A (en) | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| WO1996018399A1 (en) | 1994-12-13 | 1996-06-20 | Euro-Celtique, S.A. | Aryl thioxanthines |
| AU4527996A (en) | 1994-12-13 | 1996-07-03 | Euro-Celtique S.A. | Trisubstituted 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 |
| US6403567B1 (en) | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| US6815446B1 (en) | 1999-08-31 | 2004-11-09 | Vanderbilt University | Selective antagonists of A2B adenosine receptors |
| WO2001047931A1 (fr) | 1999-12-24 | 2001-07-05 | Kyowa Hakko Kogyo Co., Ltd. | Derives de purine fondue |
| CA2671940A1 (en) | 2000-02-23 | 2001-08-30 | Cv Therapeutics, Inc. | Identification of partial agonists of the a2a adenosine receptor |
| GB0005199D0 (en) * | 2000-03-04 | 2000-04-26 | Imp College Innovations Ltd | Modulation of histone deacetylase |
| HU229504B1 (hu) | 2001-11-09 | 2014-01-28 | Gilead Sciences | A2B-adenozinreceptor-antagonisták |
| US6977300B2 (en) | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7317017B2 (en) | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| AU2002340405A1 (en) * | 2001-11-20 | 2003-06-10 | Bristol-Myers Squibb Pharma Company | 3,7-dihydro-purine-2,6-dione derivatives as crf receptor ligands |
| US8470801B2 (en) | 2002-07-29 | 2013-06-25 | Gilead Sciences, Inc. | Myocardial perfusion imaging methods and compositions |
| US20050020915A1 (en) | 2002-07-29 | 2005-01-27 | Cv Therapeutics, Inc. | Myocardial perfusion imaging methods and compositions |
| JP2005538190A (ja) | 2002-07-29 | 2005-12-15 | シーブイ・セラピューティクス・インコーポレイテッド | 心筋潅流イメージング |
| CA2583185A1 (en) | 2004-10-20 | 2006-04-27 | Cv Therapeutics, Inc. | Use of a2a adenosine receptor agonists |
| KR101494125B1 (ko) | 2006-02-03 | 2015-02-16 | 길리애드 사이언시즈, 인코포레이티드 | Ａ2ａ-아데노신 수용체 효능제 및 이의 다형체의 제조 방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245969B (de) * | 1967-08-03 | VEB Arzneimittelwerk Dresden, Radebeul | Verfahren zur Herstellung von Xanthinderivaten | |
| CA1077932A (en) * | 1976-03-31 | 1980-05-20 | Berlex Laboratories, Inc. | Xanthine compounds and method of treating bronchospastic and allergic diseases |
| 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 |
| US4338319A (en) * | 1979-11-27 | 1982-07-06 | Aktiebolaget Draco | Method for the treatment of chronic obstructive airway or cardiac diseases |
| 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 |
| SE8602887D0 (sv) * | 1986-06-27 | 1986-06-27 | Draco Ab | New chemical method |
-
1989
- 1989-03-10 IT IT8919730A patent/IT1229195B/it active
-
1990
- 1990-03-05 EP EP19900104229 patent/EP0386683A3/de not_active Withdrawn
- 1990-03-05 ES ES90104229T patent/ES2017899A4/es active Pending
- 1990-03-05 DE DE199090104229T patent/DE386683T1/de active Pending
- 1990-03-08 JP JP2057835A patent/JPH03200787A/ja active Pending
-
1991
- 1991-09-27 GR GR90300160T patent/GR900300160T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0386683A3 (de) | 1992-01-15 |
| IT8919730A0 (it) | 1989-03-10 |
| IT1229195B (it) | 1991-07-25 |
| ES2017899A4 (es) | 1991-03-16 |
| GR900300160T1 (en) | 1991-09-27 |
| JPH03200787A (ja) | 1991-09-02 |
| EP0386683A2 (de) | 1990-09-12 |
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