IE34765B1 - Nitrofuryl-thienopyrimidines - Google Patents
Nitrofuryl-thienopyrimidinesInfo
- Publication number
- IE34765B1 IE34765B1 IE1519/70A IE151970A IE34765B1 IE 34765 B1 IE34765 B1 IE 34765B1 IE 1519/70 A IE1519/70 A IE 1519/70A IE 151970 A IE151970 A IE 151970A IE 34765 B1 IE34765 B1 IE 34765B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- carbon atoms
- formula
- reacting
- substituted
- Prior art date
Links
- -1 Nitrofuryl-thienopyrimidines Chemical class 0.000 title abstract 18
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 125000004442 acylamino group Chemical group 0.000 abstract 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 230000002140 halogenating effect Effects 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- HCOQHIZRZAXYTK-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-3H-thieno[3,2-d]pyrimidin-4-one Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=1N=C(C2=C(N1)C=CS2)O HCOQHIZRZAXYTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 abstract 1
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 230000001572 anti-trichomonad Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- WNBJXNGNGVOCKO-UHFFFAOYSA-N methyl 5-cyanofuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(C#N)O1 WNBJXNGNGVOCKO-UHFFFAOYSA-N 0.000 abstract 1
- XBYZJUMTKHUJIY-UHFFFAOYSA-N methyl 5-methylfuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(C)O1 XBYZJUMTKHUJIY-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691959403 DE1959403A1 (de) | 1969-11-26 | 1969-11-26 | Neue 2-(5-Nitro-2-furyl)-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| DE19702050814 DE2050814A1 (de) | 1970-10-16 | 1970-10-16 | Neue Verfahren zur Herstellung von 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidinen |
| DE19702050815 DE2050815A1 (de) | 1970-10-16 | 1970-10-16 | Neue 2-(5-Nitro-2-furyl)-thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidine |
| DE19702050816 DE2050816A1 (de) | 1970-10-16 | 1970-10-16 | Neue 2-(Nitro-2-furyl>thieno eckige Klammer auf 3,2-d eckige Klammer zu pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34765L IE34765L (en) | 1971-05-26 |
| IE34765B1 true IE34765B1 (en) | 1975-08-06 |
Family
ID=27430978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1519/70A IE34765B1 (en) | 1969-11-26 | 1970-11-26 | Nitrofuryl-thienopyrimidines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3661908A (enExample) |
| BE (1) | BE759493A (enExample) |
| BG (2) | BG17800A3 (enExample) |
| CA (1) | CA926865A (enExample) |
| CH (3) | CH568324A5 (enExample) |
| DK (1) | DK128781B (enExample) |
| FR (1) | FR2073416B1 (enExample) |
| GB (1) | GB1321316A (enExample) |
| IE (1) | IE34765B1 (enExample) |
| IL (1) | IL35729A (enExample) |
| NL (1) | NL7017210A (enExample) |
| NO (1) | NO129954B (enExample) |
| SE (1) | SE377938B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932642A (en) * | 1971-04-10 | 1976-01-13 | Boehringer Ingelheim Gmbh | Biocidal compositions containing a 2- (5'-nitro-2'-furyl)-thieno(2,3-d) pyrimidine and methods of use |
| US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US20040138238A1 (en) * | 2002-08-08 | 2004-07-15 | Dhanoa Dale S. | Substituted aminopyrimidine compounds as neurokinin antagonists |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| AU2007243466B2 (en) * | 2006-04-26 | 2012-01-19 | F. Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| KR101533461B1 (ko) | 2006-04-26 | 2015-07-02 | 에프. 호프만-라 로슈 아게 | Ｐｉ３ｋ저해제로 유용한 티에노［3,2-ｄ］피리미딘 유도체 |
| PL2041139T3 (pl) | 2006-04-26 | 2012-05-31 | Hoffmann La Roche | Związki farmaceutyczne |
| CA2671845C (en) * | 2006-12-07 | 2015-03-24 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| PE20081679A1 (es) * | 2006-12-07 | 2008-12-18 | Hoffmann La Roche | Compuestos del inhibidor de fosfoinositida 3-cinasa y metodos de uso |
| ATE510841T1 (de) * | 2007-06-12 | 2011-06-15 | Hoffmann La Roche | Thiazoliopyrimidine und ihre verwendung als hemmer der phosphatidylinositol-3 kinase |
| CN101932587A (zh) * | 2007-09-24 | 2010-12-29 | 吉宁特有限公司 | 噻唑并嘧啶pi3k抑制剂化合物及使用方法 |
| WO2009055730A1 (en) | 2007-10-25 | 2009-04-30 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| JP5709766B2 (ja) | 2009-03-12 | 2015-04-30 | ジェネンテック， インコーポレイテッド | 造血器腫瘍の治療のためのホスホイノシチド３キナーゼ阻害剤化合物と化学療法剤の併用 |
| SG182247A1 (en) * | 2009-05-27 | 2012-08-30 | Hoffmann La Roche | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| MX2011012520A (es) | 2009-05-27 | 2011-12-12 | Hoffmann La Roche | Compuestos inhibidores de pi3k de pirimidina biciclicos selectivos para p110 delta y metodos de uso de los mismos. |
| AU2010314287A1 (en) * | 2009-10-12 | 2012-05-03 | F. Hoffmann-La Roche Ag | Combinations of a PI3K inhibitor and a MEK inhibitor |
| KR20130058672A (ko) | 2010-04-16 | 2013-06-04 | 제넨테크, 인크. | ＰＩ3Ｋ/ＡＫＴ 키나제 경로 억제제 효능에 대한 예측 바이오마커로서의 ＦＯＸＯ３ａ |
| US20140004209A1 (en) | 2010-12-22 | 2014-01-02 | Genentech, Inc. | Autophagy inducer and inhibitor combination therapy for the treatment of neoplasms |
| RU2015140573A (ru) | 2013-02-25 | 2017-03-30 | Дженентек, Инк. | Способы и композиции для обнаружения и лечения устойчивого к лекарственным средствам мутанта акт |
-
0
- BE BE759493D patent/BE759493A/xx unknown
-
1970
- 1970-11-17 BG BG017732A patent/BG17800A3/xx unknown
- 1970-11-17 BG BG016080A patent/BG17799A3/xx unknown
- 1970-11-18 US US90841A patent/US3661908A/en not_active Expired - Lifetime
- 1970-11-23 CH CH1514974A patent/CH568324A5/xx not_active IP Right Cessation
- 1970-11-23 CH CH1731270A patent/CH559210A5/xx not_active IP Right Cessation
- 1970-11-23 CH CH1514674A patent/CH567029A5/xx not_active IP Right Cessation
- 1970-11-25 GB GB5614670A patent/GB1321316A/en not_active Expired
- 1970-11-25 DK DK601570AA patent/DK128781B/da unknown
- 1970-11-25 NL NL7017210A patent/NL7017210A/xx unknown
- 1970-11-25 NO NO04524/70A patent/NO129954B/no unknown
- 1970-11-26 CA CA099166A patent/CA926865A/en not_active Expired
- 1970-11-26 SE SE7016054A patent/SE377938B/xx unknown
- 1970-11-26 FR FR7042531A patent/FR2073416B1/fr not_active Expired
- 1970-11-26 IE IE1519/70A patent/IE34765B1/xx unknown
- 1970-11-26 IL IL35729A patent/IL35729A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE759493A (fr) | 1971-05-25 |
| IL35729A0 (en) | 1971-01-28 |
| SE377938B (enExample) | 1975-08-04 |
| BG17800A3 (bg) | 1973-12-25 |
| NO129954B (enExample) | 1974-06-17 |
| CH559210A5 (enExample) | 1975-02-28 |
| US3661908A (en) | 1972-05-09 |
| NL7017210A (enExample) | 1971-05-28 |
| FR2073416B1 (enExample) | 1975-04-18 |
| FR2073416A1 (enExample) | 1971-10-01 |
| DK128781B (da) | 1974-07-01 |
| CH567029A5 (enExample) | 1975-09-30 |
| IE34765L (en) | 1971-05-26 |
| IL35729A (en) | 1974-01-14 |
| GB1321316A (en) | 1973-06-27 |
| CA926865A (en) | 1973-05-22 |
| BG17799A3 (bg) | 1973-12-25 |
| CH568324A5 (enExample) | 1975-10-31 |
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