DE2446593A1 - Neue furo(2,3d)pyrimidine, ein verfahren zu ihrer herstellung und diese enthaltende arzneimittel - Google Patents
Neue furo(2,3d)pyrimidine, ein verfahren zu ihrer herstellung und diese enthaltende arzneimittelInfo
- Publication number
- DE2446593A1 DE2446593A1 DE19742446593 DE2446593A DE2446593A1 DE 2446593 A1 DE2446593 A1 DE 2446593A1 DE 19742446593 DE19742446593 DE 19742446593 DE 2446593 A DE2446593 A DE 2446593A DE 2446593 A1 DE2446593 A1 DE 2446593A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- radical
- furo
- anilino
- 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
- 150000001875 compounds Chemical class 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 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 4
- -1 morpholino, pyrrolidino Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002269 analeptic agent Substances 0.000 description 2
- 230000003555 analeptic effect Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000003361 anti-bronchoconstrictory effect Effects 0.000 description 2
- 230000001078 anti-cholinergic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960003910 promethazine Drugs 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 206010017999 Gastrointestinal pain Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- KQGXYVJZOMKLSA-UHFFFAOYSA-N furo[2,3-d]pyrimidine Chemical compound N1=CN=C2OC=CC2=C1 KQGXYVJZOMKLSA-UHFFFAOYSA-N 0.000 description 1
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7335190A FR2245349A1 (en) | 1973-10-02 | 1973-10-02 | Therapeutic furo (2,3-d)-pyrimidine derivs - have anti-ulcer, analgesic, anti-inflammatory, hypertensive etc. activity |
| FR7417484A FR2271823A2 (en) | 1974-05-20 | 1974-05-20 | Therapeutic furo (2,3-d)-pyrimidine derivs - have anti-ulcer, analgesic, anti-inflammatory, hypertensive etc. activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2446593A1 true DE2446593A1 (de) | 1975-04-03 |
Family
ID=26217960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742446593 Pending DE2446593A1 (de) | 1973-10-02 | 1974-09-30 | Neue furo(2,3d)pyrimidine, ein verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Country Status (11)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199584A (en) * | 1977-05-27 | 1980-04-22 | Imperial Chemical Industries Limited | Pesticidal active furo[2,3-d] pyrimidine derivatives, compositions containing the same and use thereof |
| US5137879A (en) * | 1990-03-30 | 1992-08-11 | Dowelanco | Furopyrimidin-4-imine derivatives |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| DE10148883A1 (de) * | 2001-10-04 | 2003-04-10 | Merck Patent Gmbh | Pyrimidinderivate |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| DK2024372T3 (da) | 2006-04-26 | 2010-09-20 | Hoffmann La Roche | Thieno[3,2-d]pyrimidin-derivat, der er egnet som P13K inhibitor |
| JP5546240B2 (ja) | 2006-04-26 | 2014-07-09 | ジェネンテック， インコーポレイテッド | 医薬化合物 |
| JP5291616B2 (ja) * | 2006-04-26 | 2013-09-18 | ジェネンテック， インコーポレイテッド | ホスホイノシチド３−キナーゼ抑制剤化合物およびその使用方法 |
| AR064155A1 (es) * | 2006-12-07 | 2009-03-18 | Piramed Ltd | Compuestos de inhibidores de fosfoinositido-3 quinasa y metodos de uso |
| CL2007003523A1 (es) * | 2006-12-07 | 2008-08-22 | Piramed Ltd Genentech Inc | Compuestos derivados de heterociclos sustituidos con morfolina, inhibidores de la actividad de pi3 quinasa; composicion farmaceutica que comprende a dichos compuestos; kit farmaceutico; y su uso en el tratamiento profilactico o terapeutico del cancer |
| JP5348725B2 (ja) * | 2007-10-25 | 2013-11-20 | ジェネンテック， インコーポレイテッド | チエノピリミジン化合物の製造方法 |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| BRPI1009022A2 (pt) * | 2009-05-27 | 2016-03-08 | Hoffmann La Roche | "composto, composição farmacêutica, processo para produzir uma composição farmacêutica, uso de um composto, método para tratamento de uma doença ou transtorno e kit" |
| EP2451811A1 (en) * | 2009-05-27 | 2012-05-16 | F. Hoffmann-La Roche AG | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| NZ599939A (en) * | 2009-10-12 | 2014-02-28 | Hoffmann La Roche | Combinations of a pi3k inhibitor and a mek inhibitor |
| CN102260270A (zh) * | 2010-05-28 | 2011-11-30 | 中国科学院上海药物研究所 | N-(2-甲基呋喃[2，3-d]嘧啶-4-基)丙烯酰胺、其制备方法及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA705417A (en) * | 1965-03-09 | H. Hitchings George | Pyrrolopyrimidine vasodilators and method of making them | |
| US3037980A (en) * | 1955-08-18 | 1962-06-05 | Burroughs Wellcome Co | Pyrrolopyrimidine vasodilators and method of making them |
| GB915304A (en) * | 1958-03-13 | 1963-01-09 | Wellcome Found | Pyrrolo[2,3-d]pyrimidine derivatives |
-
1974
- 1974-08-29 CH CH1177974A patent/CH592668A5/xx not_active IP Right Cessation
- 1974-09-13 GB GB3995074A patent/GB1430720A/en not_active Expired
- 1974-09-14 ES ES430051A patent/ES430051A1/es not_active Expired
- 1974-09-17 US US05/506,826 patent/US4007187A/en not_active Expired - Lifetime
- 1974-09-26 LU LU71010A patent/LU71010A1/xx unknown
- 1974-09-30 DE DE19742446593 patent/DE2446593A1/de active Pending
- 1974-10-01 SU SU7402063645A patent/SU581868A3/ru active
- 1974-10-01 CA CA210,451A patent/CA1015754A/en not_active Expired
- 1974-10-01 JP JP49113222A patent/JPS5076091A/ja active Pending
- 1974-10-01 SE SE7412346A patent/SE7412346L/xx unknown
- 1974-10-02 NL NL7413033A patent/NL7413033A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1430720A (en) | 1976-04-07 |
| LU71010A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-16 |
| US4007187A (en) | 1977-02-08 |
| SU581868A3 (ru) | 1977-11-25 |
| JPS5076091A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-21 |
| ES430051A1 (es) | 1976-10-01 |
| SE7412346L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-03 |
| AU7364874A (en) | 1976-04-01 |
| NL7413033A (nl) | 1975-04-04 |
| CH592668A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-10-31 |
| CA1015754A (en) | 1977-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |