DE2257547A1 - Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine - Google Patents
Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidineInfo
- Publication number
- DE2257547A1 DE2257547A1 DE2257547A DE2257547A DE2257547A1 DE 2257547 A1 DE2257547 A1 DE 2257547A1 DE 2257547 A DE2257547 A DE 2257547A DE 2257547 A DE2257547 A DE 2257547A DE 2257547 A1 DE2257547 A1 DE 2257547A1
- Authority
- DE
- Germany
- Prior art keywords
- compound according
- methyl
- pyrimidine
- carbethoxy
- alkyl
- 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 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 27
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 26
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 24
- 150000003230 pyrimidines Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- RDCODVKTTJWFAR-UHFFFAOYSA-N 4-ethyl-1h-pyrazol-5-amine Chemical compound CCC=1C=NNC=1N RDCODVKTTJWFAR-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 alkoyl Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229940000635 beta-alanine Drugs 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000012434 nucleophilic reagent Substances 0.000 claims description 2
- 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 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000243 solution Substances 0.000 description 99
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 86
- 239000000047 product Substances 0.000 description 70
- 238000004458 analytical method Methods 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 229910052757 nitrogen Inorganic materials 0.000 description 48
- 239000000203 mixture Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000001953 recrystallisation Methods 0.000 description 26
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 239000003208 petroleum Substances 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 20
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- LBWVNVFQCVTMMH-UHFFFAOYSA-N 5,7-dimethylpyrazolo[1,5-a]pyrimidine Chemical compound N1=C(C)C=C(C)N2N=CC=C21 LBWVNVFQCVTMMH-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- YPXGHKWOJXQLQU-UHFFFAOYSA-N ethyl 5-amino-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1N YPXGHKWOJXQLQU-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 14
- 229960000278 theophylline Drugs 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000012259 ether extract Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 9
- SIWACKGVBCDSRI-UHFFFAOYSA-N 7-chloro-6-ethoxy-3-ethylpyrazolo[1,5-a]pyrimidine Chemical compound ClC1=C(OCC)C=NC2=C(CC)C=NN21 SIWACKGVBCDSRI-UHFFFAOYSA-N 0.000 description 9
- 229940095074 cyclic amp Drugs 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
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- 239000012362 glacial acetic acid Substances 0.000 description 9
- 230000000144 pharmacologic effect Effects 0.000 description 9
- LAIQFRPXRDLDQG-UHFFFAOYSA-N 7-chloro-3-ethyl-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound ClC1=CC(C)=NC2=C(CC)C=NN21 LAIQFRPXRDLDQG-UHFFFAOYSA-N 0.000 description 8
- BJXJEUOXFCAJLA-UHFFFAOYSA-N 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound N1=C(C)C=C(Cl)N2N=CC=C21 BJXJEUOXFCAJLA-UHFFFAOYSA-N 0.000 description 8
- 239000004471 Glycine Substances 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 241000283973 Oryctolagus cuniculus Species 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 210000004072 lung Anatomy 0.000 description 8
- 241000700199 Cavia porcellus Species 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 7
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 7
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- WUPBXHOKESCXBJ-UHFFFAOYSA-N 3-bromo-5,7-dimethylpyrazolo[1,5-a]pyrimidine Chemical compound N1=C(C)C=C(C)N2N=CC(Br)=C21 WUPBXHOKESCXBJ-UHFFFAOYSA-N 0.000 description 6
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- 238000001228 spectrum Methods 0.000 description 6
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 210000003462 vein Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20653871A | 1971-12-09 | 1971-12-09 | |
| US245870A US3925385A (en) | 1972-04-20 | 1972-04-20 | 6-Carbethoxy-3,7-disubstitutedpyrazolo{8 1,5a{9 pyrimidines |
| US27346572A | 1972-07-20 | 1972-07-20 | |
| US29984072A | 1972-10-24 | 1972-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2257547A1 true DE2257547A1 (de) | 1973-06-14 |
Family
ID=27498614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257547A Pending DE2257547A1 (de) | 1971-12-09 | 1972-11-23 | Pyrazolo eckige klammer auf 1,5a eckige klammer zu -pyrimidine |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4864097A (cg-RX-API-DMAC10.html) |
| BE (1) | BE792533A (cg-RX-API-DMAC10.html) |
| BG (1) | BG22401A3 (cg-RX-API-DMAC10.html) |
| CH (1) | CH603652A5 (cg-RX-API-DMAC10.html) |
| DD (1) | DD104530A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2257547A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1412017A (cg-RX-API-DMAC10.html) |
| HU (1) | HU168530B (cg-RX-API-DMAC10.html) |
| IE (1) | IE37189B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL40895A (cg-RX-API-DMAC10.html) |
| LU (1) | LU66597A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7216539A (cg-RX-API-DMAC10.html) |
| NO (1) | NO137012C (cg-RX-API-DMAC10.html) |
| RO (1) | RO62762A (cg-RX-API-DMAC10.html) |
| SE (1) | SE398751B (cg-RX-API-DMAC10.html) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025819A1 (en) * | 1979-07-09 | 1981-04-01 | American Cyanamid Company | Substituted pyrazolo (1,5-a) pyrimidines, and their preparation |
| EP0215382A1 (de) * | 1985-09-17 | 1987-03-25 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]pyrimidine und diese enthaltende Fungizide |
| EP0129847A3 (en) * | 1983-06-23 | 1987-05-20 | American Cyanamid Company | Aryl and heteroarylû7-(aryl and heteroaryl)-pyrazolo-û1,5-a¨-pyrimidin-3-yl¨methanones |
| US5688949A (en) * | 1991-04-22 | 1997-11-18 | Otsuka Pharmaceutical Factory, Inc. | Pyrazolo 1,5-A!pyrimidine derivatives and anti-inflammatory agent containing the same |
| EP0795555A4 (en) * | 1995-09-28 | 1998-01-07 | Otsuka Pharma Co Ltd | ANALGESICS |
| FR2771631A1 (fr) * | 1997-12-03 | 1999-06-04 | Oreal | Compositions de teinture des fibres keratiniques contenant des 3-amino pyrazolo-[1,5-a]-pyrimidines, procede de teinture, nouvelles 3-amino pyrazolo- [1,5-a]-pyrimidines et leur procede de preparation |
| DE4333705C2 (de) * | 1993-10-02 | 2003-10-30 | Guenter Ege | Arylmethylsubstituierte Pyrazolo-azine, insbesondere 3-Arylmethylpyrazolo[1,5-a]pyrimidine und Verfahren zur Herstellung von 8-Arylmethyl-pyrazolo[5,1-c][1,2,4]triazinen |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU557300B2 (en) * | 1982-03-16 | 1986-12-18 | Farmitalia Carlo Erba S.P.A. | Substituted 1h-pyrazolo(1,5-alpha)pyrimidines and processes for their preparation |
| ZA831407B (en) * | 1982-03-25 | 1983-11-30 | Erba Farmitalia | Substituted ethenyl derivatives of 1h-pyrazolo(1,5-a)pyrimidine and process for their preparation |
| CA1330079C (en) * | 1988-10-13 | 1994-06-07 | Michihiko Tsujitani | Pyrrolo (3,2-e)pyrazolo(1,5-a)pyrimidine derivative and medicine comprising the same |
| EP0714898B1 (en) * | 1994-06-21 | 2001-11-14 | Otsuka Pharmaceutical Factory, Inc. | PYRAZOLO [1,5-a]PYRIMIDINE DERIVATIVE |
| JP4881558B2 (ja) * | 2002-09-04 | 2012-02-22 | シェーリング コーポレイション | サイクリン依存性キナーゼインヒビターとしてのピラゾロピリミジン |
| US7119200B2 (en) * | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7161003B1 (en) | 2002-09-04 | 2007-01-09 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| ES2222813B1 (es) * | 2003-07-24 | 2005-12-16 | Ferrer Internacional, S.A. | N-(3-(3-sustituidas-pirazolo(1,5-a)pirimidin-7-il)-fenil)-sulfonamidas y composiciones y metodos relacionados. |
| TWI252851B (en) * | 2003-07-24 | 2006-04-11 | Ferrer Int | 7-substituted 3-nitro-pyrazolo[1,5-a]pyrimidines and compositions and methods related thereto |
| PL2989106T3 (pl) | 2013-04-25 | 2017-08-31 | Beigene, Ltd. | Połączone związki heterocykliczne jako inhibitory kinazy białkowej |
| SMT202300039T1 (it) | 2013-09-13 | 2023-03-17 | Beigene Switzerland Gmbh | Anticorpi anti-pd1 e loro uso come terapia e per diagnostica |
| TWI726608B (zh) | 2014-07-03 | 2021-05-01 | 英屬開曼群島商百濟神州有限公司 | 抗pd-l1抗體及其作為治療及診斷之用途 |
| WO2018007885A1 (en) | 2016-07-05 | 2018-01-11 | Beigene, Ltd. | COMBINATION OF A PD-l ANTAGONIST AND A RAF INHIBITOR FOR TREATING CANCER |
| IL293319B1 (en) | 2016-08-16 | 2026-01-01 | Beone Medicines Ltd | Crystal structure of s)–7–(1–acryloylpiperidin–4–yl)–2–(4–)phenoxyphenyl)–4,5,6,7–tetra–hydropyrazolo(1,5–a)pyrimidine–3–carboxamide, methods of preparation and uses thereof |
| CN110087680B (zh) | 2016-08-19 | 2024-03-19 | 百济神州有限公司 | 使用包含btk抑制剂的组合产品治疗癌症 |
| EP3573989A4 (en) | 2017-01-25 | 2020-11-18 | Beigene, Ltd. | CRYSTALLINE FORMS OF (S) -7- (1- (BUT-2-YNOYL) PIPERIDIN-4-YL) -2- (4-PHENOXYPHENYL) -4, 5, 6, 7-TETRAHY DROPYRAZOLO [1, 5-A ] PYRIMIDINE-3-CARBOXAMIDE, PREPARATION AND ASSOCIATED USES |
| EP3645569A4 (en) | 2017-06-26 | 2021-03-24 | BeiGene, Ltd. | IMMUNOTHERAPY FOR LIVER CELL CARCINOMA |
| WO2019034009A1 (en) | 2017-08-12 | 2019-02-21 | Beigene, Ltd. | BTK INHIBITOR WITH ENHANCED DOUBLE SELECTIVITY |
| US11786529B2 (en) | 2017-11-29 | 2023-10-17 | Beigene Switzerland Gmbh | Treatment of indolent or aggressive B-cell lymphomas using a combination comprising BTK inhibitors |
| EP3981399A4 (en) | 2019-06-10 | 2023-05-31 | BeiGene Switzerland GmbH | ORAL SOLID TABLET WITH A TYROSINE KINAS INHIBITOR AND METHOD OF MANUFACTURE THEREOF |
| US11786531B1 (en) | 2022-06-08 | 2023-10-17 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
-
0
- BE BE792533D patent/BE792533A/xx unknown
-
1972
- 1972-11-21 IE IE1612/72A patent/IE37189B1/xx unknown
- 1972-11-22 IL IL40895A patent/IL40895A/en unknown
- 1972-11-23 DE DE2257547A patent/DE2257547A1/de active Pending
- 1972-12-01 GB GB5558772A patent/GB1412017A/en not_active Expired
- 1972-12-05 LU LU66597A patent/LU66597A1/xx unknown
- 1972-12-05 SE SE7215829A patent/SE398751B/xx unknown
- 1972-12-06 NO NO4476/72A patent/NO137012C/no unknown
- 1972-12-06 NL NL7216539A patent/NL7216539A/xx not_active Application Discontinuation
- 1972-12-06 CH CH1775172A patent/CH603652A5/xx not_active IP Right Cessation
- 1972-12-07 DD DD167370A patent/DD104530A5/xx unknown
- 1972-12-08 HU HUIE548A patent/HU168530B/hu unknown
- 1972-12-09 JP JP47123877A patent/JPS4864097A/ja active Pending
- 1972-12-09 RO RO7200073093A patent/RO62762A/ro unknown
- 1972-12-09 BG BG022071A patent/BG22401A3/xx unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025819A1 (en) * | 1979-07-09 | 1981-04-01 | American Cyanamid Company | Substituted pyrazolo (1,5-a) pyrimidines, and their preparation |
| EP0129847A3 (en) * | 1983-06-23 | 1987-05-20 | American Cyanamid Company | Aryl and heteroarylû7-(aryl and heteroaryl)-pyrazolo-û1,5-a¨-pyrimidin-3-yl¨methanones |
| EP0215382A1 (de) * | 1985-09-17 | 1987-03-25 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]pyrimidine und diese enthaltende Fungizide |
| US5688949A (en) * | 1991-04-22 | 1997-11-18 | Otsuka Pharmaceutical Factory, Inc. | Pyrazolo 1,5-A!pyrimidine derivatives and anti-inflammatory agent containing the same |
| DE4333705C2 (de) * | 1993-10-02 | 2003-10-30 | Guenter Ege | Arylmethylsubstituierte Pyrazolo-azine, insbesondere 3-Arylmethylpyrazolo[1,5-a]pyrimidine und Verfahren zur Herstellung von 8-Arylmethyl-pyrazolo[5,1-c][1,2,4]triazinen |
| EP0795555A4 (en) * | 1995-09-28 | 1998-01-07 | Otsuka Pharma Co Ltd | ANALGESICS |
| US5843951A (en) * | 1995-09-28 | 1998-12-01 | Otsuka Pharmaceutical Factory Inc. | Analgesic composition of pyrazolo(1,5-A) pyrimidines |
| FR2771631A1 (fr) * | 1997-12-03 | 1999-06-04 | Oreal | Compositions de teinture des fibres keratiniques contenant des 3-amino pyrazolo-[1,5-a]-pyrimidines, procede de teinture, nouvelles 3-amino pyrazolo- [1,5-a]-pyrimidines et leur procede de preparation |
| EP0926149A1 (fr) * | 1997-12-03 | 1999-06-30 | L'oreal | Compositions de teinture des fibres kératinques contenant des 3-aminopyrazolo-[1,5-a]-pyrimidines, procédé de teinture, nouvelles 3-aminopyrazolo-[1,5-a]-pyrimidines et leur procédé de préparation |
| US6248137B1 (en) | 1997-12-03 | 2001-06-19 | L'oreal S.A. | Compositions for dyeing keratinous fibres, containing 3-aminopyrazolo [1,5-a]pyrimidines, method of dyeing and novel 3-aminopyrazolo [1,5-a]pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| NO137012B (no) | 1977-09-05 |
| IL40895A (en) | 1976-12-31 |
| IE37189B1 (en) | 1977-05-25 |
| LU66597A1 (cg-RX-API-DMAC10.html) | 1973-03-15 |
| SE398751B (sv) | 1978-01-16 |
| IL40895A0 (en) | 1973-01-30 |
| BE792533A (fr) | 1973-06-08 |
| HU168530B (cg-RX-API-DMAC10.html) | 1976-05-28 |
| CH603652A5 (cg-RX-API-DMAC10.html) | 1978-08-31 |
| IE37189L (en) | 1973-06-09 |
| BG22401A3 (bg) | 1977-02-20 |
| JPS4864097A (cg-RX-API-DMAC10.html) | 1973-09-05 |
| NO137012C (no) | 1977-12-14 |
| GB1412017A (en) | 1975-10-29 |
| RO62762A (fr) | 1978-05-15 |
| DD104530A5 (cg-RX-API-DMAC10.html) | 1974-03-12 |
| NL7216539A (cg-RX-API-DMAC10.html) | 1973-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |