DE2615586A1 - Neues verfahren zur herstellung bestimmter pyrazolo(3,4-b)pyridinketone - Google Patents
Neues verfahren zur herstellung bestimmter pyrazolo(3,4-b)pyridinketoneInfo
- Publication number
- DE2615586A1 DE2615586A1 DE19762615586 DE2615586A DE2615586A1 DE 2615586 A1 DE2615586 A1 DE 2615586A1 DE 19762615586 DE19762615586 DE 19762615586 DE 2615586 A DE2615586 A DE 2615586A DE 2615586 A1 DE2615586 A1 DE 2615586A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrazolo
- pyridine
- lower alkyl
- phenyl
- methyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 5-acetyl-4-ethoxy-1- (2-furanyl) methyl-iH-pyrazolo (3,4-b) pyridine Chemical compound 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- FTIWPDXHZYSCDP-UHFFFAOYSA-N [4-ethoxy-1-(furan-2-yl)-3-methylpyrazolo[3,4-b]pyridin-5-yl]-phenylmethanone Chemical compound N1=C(C)C=2C(OCC)=C(C(=O)C=3C=CC=CC=3)C=NC=2N1C1=CC=CO1 FTIWPDXHZYSCDP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- UUFCJXBBFXOXKY-UHFFFAOYSA-N (4-ethoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone Chemical compound C1=NC=2NN=CC=2C(OCC)=C1C(=O)C1=CC=CC=C1 UUFCJXBBFXOXKY-UHFFFAOYSA-N 0.000 claims description 2
- QHGGOPIVFKNRMF-UHFFFAOYSA-N 1-(4-ethoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)ethanone Chemical compound CCOC1=C(C(C)=O)C=NC2=C1C=NN2 QHGGOPIVFKNRMF-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000126 substance Substances 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
- YTNUSJXGLVWZIP-UHFFFAOYSA-N O1C(=CC=C1)N1N=C(C=C1N)C Chemical compound O1C(=CC=C1)N1N=C(C=C1N)C YTNUSJXGLVWZIP-UHFFFAOYSA-N 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- CBEBUPCULLWDJM-UHFFFAOYSA-N (1-amino-4-ethyl-6-phenylpyrazolo[3,4-b]pyridin-5-yl)-(4-methoxyphenyl)methanone Chemical compound C(C)C1=C2C(=NC(=C1C(C1=CC=C(C=C1)OC)=O)C1=CC=CC=C1)N(N=C2)N CBEBUPCULLWDJM-UHFFFAOYSA-N 0.000 description 1
- KTKZUPUIOWBNRU-UHFFFAOYSA-N (3-chlorophenyl)-(4-methoxy-6-methyl-1h-pyrazolo[3,4-b]pyridin-5-yl)methanone Chemical compound CC1=NC=2NN=CC=2C(OC)=C1C(=O)C1=CC=CC(Cl)=C1 KTKZUPUIOWBNRU-UHFFFAOYSA-N 0.000 description 1
- YTDALEMUXJEGIN-UHFFFAOYSA-N (4-anilino-6-methyl-1h-pyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C=1C(C)=NC=2NN=CC=2C=1NC1=CC=CC=C1 YTDALEMUXJEGIN-UHFFFAOYSA-N 0.000 description 1
- JZNIHAGABNQTKO-UHFFFAOYSA-N 1-(4-ethoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)butan-1-one Chemical compound CCCC(=O)C1=CN=C2NN=CC2=C1OCC JZNIHAGABNQTKO-UHFFFAOYSA-N 0.000 description 1
- GEKHTMXVKXGLNV-UHFFFAOYSA-N 1-(4-pyrrolidin-1-yl-1h-pyrazolo[3,4-b]pyridin-5-yl)propan-1-one Chemical compound CCC(=O)C1=CN=C2NN=CC2=C1N1CCCC1 GEKHTMXVKXGLNV-UHFFFAOYSA-N 0.000 description 1
- LKJUDUBQCKILIF-UHFFFAOYSA-N 1-[4-(2-phenylethylamino)-1h-pyrazolo[3,4-b]pyridin-5-yl]ethanone Chemical compound CC(=O)C1=CN=C2NN=CC2=C1NCCC1=CC=CC=C1 LKJUDUBQCKILIF-UHFFFAOYSA-N 0.000 description 1
- AZWPZEGGNCFEKN-UHFFFAOYSA-N 1-methylpyrazolo[3,4-b]pyridine Chemical compound C1=CN=C2N(C)N=CC2=C1 AZWPZEGGNCFEKN-UHFFFAOYSA-N 0.000 description 1
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- MLVPOBOYTLCKSS-UHFFFAOYSA-N 5-benzoyl-1-(furan-2-yl)-3-methyl-7H-pyrazolo[3,4-b]pyridin-4-one Chemical compound C(C1=CC=CC=C1)(=O)C=1C(=C2C(=NC=1)N(N=C2C)C=1OC=CC=1)O MLVPOBOYTLCKSS-UHFFFAOYSA-N 0.000 description 1
- FXOZRYSWODOMND-UHFFFAOYSA-N 5-benzoyl-1-(furan-2-ylmethyl)-7H-pyrazolo[3,4-b]pyridin-4-one Chemical compound N1=CC=2C(O)=C(C(=O)C=3C=CC=CC=3)C=NC=2N1CC1=CC=CO1 FXOZRYSWODOMND-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CMLUNJUEYYRQCZ-UHFFFAOYSA-N [4-(butylamino)-6-phenyl-1h-pyrazolo[3,4-b]pyridin-5-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C1=NC=2NN=CC=2C(NCCCC)=C1C(=O)C1=CC=CC=C1 CMLUNJUEYYRQCZ-UHFFFAOYSA-N 0.000 description 1
- YCVAPTUUQILEBH-UHFFFAOYSA-N [4-amino-1-(furan-2-ylmethyl)-3-methylpyrazolo[3,4-b]pyridin-5-yl]-phenylmethanone Chemical compound C12=NC=C(C(=O)C=3C=CC=CC=3)C(N)=C2C(C)=NN1CC1=CC=CO1 YCVAPTUUQILEBH-UHFFFAOYSA-N 0.000 description 1
- WUOSWTRPIUSYQL-UHFFFAOYSA-N [4-ethoxy-1-(furan-2-ylmethyl)pyrazolo[3,4-b]pyridin-5-yl]-phenylmethanone Chemical compound N1=CC=2C(OCC)=C(C(=O)C=3C=CC=CC=3)C=NC=2N1CC1=CC=CO1 WUOSWTRPIUSYQL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- YAHUDNWHZFLCBN-UHFFFAOYSA-N ethyl 2-benzoyl-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=CC=C1 YAHUDNWHZFLCBN-UHFFFAOYSA-N 0.000 description 1
- XDHWYQRLMSOZOP-UHFFFAOYSA-N ethyl 5-ethoxy-3-oxopent-4-enoate Chemical compound CCOC=CC(=O)CC(=O)OCC XDHWYQRLMSOZOP-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Classifications
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/568,755 US3987051A (en) | 1975-04-16 | 1975-04-16 | Method for producing 1-unsubstituted pyrazolo[3,4-b]pyridine ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2615586A1 true DE2615586A1 (de) | 1976-10-28 |
Family
ID=24272601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762615586 Withdrawn DE2615586A1 (de) | 1975-04-16 | 1976-04-09 | Neues verfahren zur herstellung bestimmter pyrazolo(3,4-b)pyridinketone |
Country Status (9)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062858A (en) * | 1976-12-22 | 1977-12-13 | E. R. Squibb & Sons, Inc. | Derivatives of 5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-ones and 11(1H)-imines |
| EP1043998B1 (en) * | 1997-12-13 | 2007-03-07 | Bristol-Myers Squibb Company | USE OF PYRAZOLO [3,4-b] PYRIDINE AS CYCLIN DEPENDANT KINASE INHIBITORS |
| US6326379B1 (en) | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
-
1975
- 1975-04-16 US US05/568,755 patent/US3987051A/en not_active Expired - Lifetime
-
1976
- 1976-03-23 CA CA248,560A patent/CA1057758A/en not_active Expired
- 1976-04-02 GB GB13524/76A patent/GB1530027A/en not_active Expired
- 1976-04-09 DE DE19762615586 patent/DE2615586A1/de not_active Withdrawn
- 1976-04-13 HU HU76SU912A patent/HU174844B/hu unknown
- 1976-04-15 CH CH486576A patent/CH609693A5/xx not_active IP Right Cessation
- 1976-04-15 IE IE825/76A patent/IE43868B1/en unknown
- 1976-04-16 FR FR7611301A patent/FR2307812A1/fr active Granted
- 1976-04-16 JP JP51044160A patent/JPS51128997A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2307812A1 (fr) | 1976-11-12 |
| IE43868B1 (en) | 1981-06-17 |
| JPS51128997A (en) | 1976-11-10 |
| US3987051A (en) | 1976-10-19 |
| CA1057758A (en) | 1979-07-03 |
| HU174844B (hu) | 1980-03-28 |
| GB1530027A (en) | 1978-10-25 |
| CH609693A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-03-15 |
| FR2307812B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-31 |
| IE43868L (en) | 1976-10-16 |
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