IE43868B1 - Pyrazolo-pyridine derivatives - Google Patents
Pyrazolo-pyridine derivativesInfo
- Publication number
- IE43868B1 IE43868B1 IE825/76A IE82576A IE43868B1 IE 43868 B1 IE43868 B1 IE 43868B1 IE 825/76 A IE825/76 A IE 825/76A IE 82576 A IE82576 A IE 82576A IE 43868 B1 IE43868 B1 IE 43868B1
- Authority
- IE
- Ireland
- Prior art keywords
- pyrazolo
- pyridine
- lower alkyl
- phenyl
- acid
- Prior art date
Links
- 150000005229 pyrazolopyridines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- -1 sulphuric Chemical class 0.000 abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- MRDVEANIAFFFKJ-UHFFFAOYSA-N piperidine pyrrolidine Chemical compound N1CCCCC1.N1CCCC1.N1CCCC1 MRDVEANIAFFFKJ-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 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
- 239000002244 precipitate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical group C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000005289 uranyl group Chemical group 0.000 description 3
- 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 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 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 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
- 239000003874 central nervous system depressant Substances 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
- QDVQAQZLFBJZQL-UHFFFAOYSA-N ethyl 5-[[1-(furan-2-ylmethyl)pyrazol-3-yl]amino]-3-oxopent-4-enoate Chemical compound N1=C(NC=CC(=O)CC(=O)OCC)C=CN1CC1=CC=CO1 QDVQAQZLFBJZQL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WVRZULUTBJHAAO-UHFFFAOYSA-N (4-amino-3-methyl-2h-pyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone Chemical compound NC1=C2C(C)=NNC2=NC=C1C(=O)C1=CC=CC=C1 WVRZULUTBJHAAO-UHFFFAOYSA-N 0.000 description 1
- DARUYCQCOQATNX-UHFFFAOYSA-N (4-butoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone Chemical compound C1=NC=2NN=CC=2C(OCCCC)=C1C(=O)C1=CC=CC=C1 DARUYCQCOQATNX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RXLQDPDOTJGGKU-UHFFFAOYSA-N 1-(4-piperidin-1-yl-1h-pyrazolo[3,4-b]pyridin-5-yl)ethanone Chemical compound CC(=O)C1=CN=C2NN=CC2=C1N1CCCCC1 RXLQDPDOTJGGKU-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
- GFJCHEPVJSIWKV-UHFFFAOYSA-N 1-[4-(cyclopentylamino)-3-methyl-2h-pyrazolo[3,4-b]pyridin-5-yl]ethanone Chemical compound CC(=O)C1=CN=C2NN=C(C)C2=C1NC1CCCC1 GFJCHEPVJSIWKV-UHFFFAOYSA-N 0.000 description 1
- VEIAWUZMEDYVEL-UHFFFAOYSA-N 1-[4-ethoxy-1-(furan-2-ylmethyl)pyrazolo[3,4-b]pyridin-5-yl]ethanone Chemical compound N1=CC=2C(OCC)=C(C(C)=O)C=NC=2N1CC1=CC=CO1 VEIAWUZMEDYVEL-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
- CZTODPMGIIIPHN-UHFFFAOYSA-N 2-(furan-2-ylmethyl)pyrazol-3-amine Chemical compound NC1=CC=NN1CC1=CC=CO1 CZTODPMGIIIPHN-UHFFFAOYSA-N 0.000 description 1
- DYGFVFYPAAPVLB-UHFFFAOYSA-N 2-benzoyl-3-[[2-(furan-2-ylmethyl)pyrazol-3-yl]amino]prop-2-enoic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)O)=CNC1=CC=NN1CC1=CC=CO1 DYGFVFYPAAPVLB-UHFFFAOYSA-N 0.000 description 1
- VISYPTDDWLOSGX-UHFFFAOYSA-N 2-benzoyl-3-ethoxyprop-2-enoic acid Chemical compound CCOC=C(C(O)=O)C(=O)C1=CC=CC=C1 VISYPTDDWLOSGX-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
- ONPGUBBNUZXCKJ-UHFFFAOYSA-N 5-acetyl-1-(furan-2-ylmethyl)-7H-pyrazolo[3,4-b]pyridin-4-one Chemical compound N1=CC2=C(O)C(C(=O)C)=CN=C2N1CC1=CC=CO1 ONPGUBBNUZXCKJ-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
- OARGKWQXYODZDG-UHFFFAOYSA-N 5-ethoxy-3-oxopent-4-enoic acid Chemical compound CCOC=CC(=O)CC(O)=O OARGKWQXYODZDG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-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
- 230000002411 adverse Effects 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
- 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
- 239000003153 chemical reaction reagent Substances 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
- 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
- MLFJUDLLBKGLPW-UHFFFAOYSA-N cyclohexyl-(4-ethoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)methanone Chemical compound C1=NC=2NN=CC=2C(OCC)=C1C(=O)C1CCCCC1 MLFJUDLLBKGLPW-UHFFFAOYSA-N 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
- 238000004821 distillation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 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
- 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
- 125000002098 pyridazinyl group Chemical group 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
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 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
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE43868L IE43868L (en) | 1976-10-16 |
| IE43868B1 true IE43868B1 (en) | 1981-06-17 |
Family
ID=24272601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE825/76A IE43868B1 (en) | 1975-04-16 | 1976-04-15 | Pyrazolo-pyridine derivatives |
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 |
| CA2314355A1 (en) * | 1997-12-13 | 1999-06-24 | Bristol-Myers Squibb Company | Use of pyrazolo ¢3,4-b! pyridine as cyclin dependent 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 |
|---|---|
| HU174844B (hu) | 1980-03-28 |
| US3987051A (en) | 1976-10-19 |
| JPS51128997A (en) | 1976-11-10 |
| CH609693A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-03-15 |
| DE2615586A1 (de) | 1976-10-28 |
| FR2307812B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-31 |
| IE43868L (en) | 1976-10-16 |
| GB1530027A (en) | 1978-10-25 |
| CA1057758A (en) | 1979-07-03 |
| FR2307812A1 (fr) | 1976-11-12 |
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