GB1328679A - Pyridopyrimidines - Google Patents
PyridopyrimidinesInfo
- Publication number
- GB1328679A GB1328679A GB4828970A GB4828970A GB1328679A GB 1328679 A GB1328679 A GB 1328679A GB 4828970 A GB4828970 A GB 4828970A GB 4828970 A GB4828970 A GB 4828970A GB 1328679 A GB1328679 A GB 1328679A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- reaction
- group
- phenyl
- atom
- 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
- 150000008518 pyridopyrimidines Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 16
- -1 ketone imine Chemical class 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 239000000460 chlorine Substances 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000002576 ketones Chemical class 0.000 abstract 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- XISPDDYROWQPHI-UHFFFAOYSA-N 3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-2-one Chemical class C1=CN=C2NC(=O)NCC2=C1 XISPDDYROWQPHI-UHFFFAOYSA-N 0.000 abstract 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- MHHOMHMNIRXARC-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-2-one Chemical compound C1=CN=C2NC(=O)N=CC2=C1 MHHOMHMNIRXARC-UHFFFAOYSA-N 0.000 abstract 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 abstract 1
- LZLIPWXJWNAMQJ-UHFFFAOYSA-N 2-chloro-5-(4-chlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=CN=C(Cl)C(C#N)=C1 LZLIPWXJWNAMQJ-UHFFFAOYSA-N 0.000 abstract 1
- PPAIIRSMKNKVOH-UHFFFAOYSA-N 2-oxo-5-phenyl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CC=C1 PPAIIRSMKNKVOH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 150000002641 lithium Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87044569A | 1969-10-20 | 1969-10-20 | |
| CA067069A CA932731A (en) | 1968-12-10 | 1969-11-10 | 1,2-dihydro-pyrido(2,3-d)pyrimidin-2-ones |
| US4253970A | 1970-06-01 | 1970-06-01 | |
| US4253870A | 1970-06-01 | 1970-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1328679A true GB1328679A (en) | 1973-08-30 |
Family
ID=27425365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4828970A Expired GB1328679A (en) | 1969-10-20 | 1970-10-12 | Pyridopyrimidines |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4843920B1 (enrdf_load_stackoverflow) |
| AU (1) | AU2124270A (enrdf_load_stackoverflow) |
| BE (1) | BE757702A (enrdf_load_stackoverflow) |
| CH (2) | CH538498A (enrdf_load_stackoverflow) |
| DE (1) | DE2051013A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2070146A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1328679A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007275696B2 (en) * | 2006-07-17 | 2011-11-10 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ322197A (en) * | 1995-11-21 | 1999-02-25 | Yamanouchi Pharma Co Ltd | Pyrido[2,3-d] pyrimidine derivatives and pharmaceutical compositions thereof |
| KR100932093B1 (ko) * | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
| US8263585B2 (en) | 2007-05-04 | 2012-09-11 | Novartis Ag | Organic compounds |
| US8268834B2 (en) * | 2008-03-19 | 2012-09-18 | Novartis Ag | Pyrazine derivatives that inhibit phosphatidylinositol 3-kinase enzyme |
-
0
- BE BE757702D patent/BE757702A/xx unknown
-
1970
- 1970-10-08 CH CH533373A patent/CH538498A/de not_active IP Right Cessation
- 1970-10-08 CH CH1490070A patent/CH537401A/de not_active IP Right Cessation
- 1970-10-12 GB GB4828970A patent/GB1328679A/en not_active Expired
- 1970-10-17 DE DE19702051013 patent/DE2051013A1/de active Pending
- 1970-10-19 AU AU21242/70A patent/AU2124270A/en not_active Expired
- 1970-10-19 FR FR7037611A patent/FR2070146A1/fr not_active Withdrawn
- 1970-10-19 JP JP45091230A patent/JPS4843920B1/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007275696B2 (en) * | 2006-07-17 | 2011-11-10 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4843920B1 (enrdf_load_stackoverflow) | 1973-12-21 |
| AU2124270A (en) | 1972-04-20 |
| CH537401A (de) | 1973-05-31 |
| DE2051013A1 (de) | 1971-12-02 |
| CH538498A (de) | 1973-08-15 |
| FR2070146A1 (enrdf_load_stackoverflow) | 1971-09-10 |
| BE757702A (fr) | 1971-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |