IL40895A - Pyrazolo(1,5a)pyrimidines and their preparation - Google Patents
Pyrazolo(1,5a)pyrimidines and their preparationInfo
- Publication number
- IL40895A IL40895A IL40895A IL4089572A IL40895A IL 40895 A IL40895 A IL 40895A IL 40895 A IL40895 A IL 40895A IL 4089572 A IL4089572 A IL 4089572A IL 40895 A IL40895 A IL 40895A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- methyl
- bromine
- alkyl
- halogen
- Prior art date
Links
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)
Claims (7)
1. CLAIMS: A compound of the structure wherein is H, loweralkoxycarbonyl, alkyl, cyano, halogen, carbamoyl, loweralkanoyl, aminomethyl, diloweralkylamino-methyl, nitro, amino, or acetamido; R2 is loweralkyl, OH, CI, NH2, C1 to linear or branched alkoxy, to Cg alkylthio, SH or loweralkyl or diloweralkylamino, piperidino, hydrazino , N,N' -loweralkylidenehydrazino,hydroxyloweralky1-amino, di(loweralkoxy)loweralkylamino, N,N-diloweralkyl-hydrazino or carboxylloweralkylamino; R^ is H, alkoxycarbonyl, or to ^ linear or branched alkoxy; and.R^.is _H,. alkyl .o.rw_ phenyl; provided that when one of ^ or R^ is not H, the other is H; when R2 and R^ are methyl, R^ is not H or carbethoxy when R^ is carbethoxy and R2 is OH or amino, is not H; when R4 is CE ^ or phenyl and R2 is OH, CI hydrazino, methoxy or ethoxy, is not H; and when R2 is amino R. is not methyl or ethyl.
2. The compound of claim 1 in which R2 and R^ . are alkyl and ^ is halogen.
3. The compound of claim 2 in which 2 and R^ are methyl and R-^ is bromine.
4. The compound of claim 2 in which 2 arid R^ are methyl and R^ is chlorine. .
5. The compound of claim 2 in which 2 and R^ are methyl and ^ is. iodine.
6. The compound of claim 2 in which ^ is methyl, R2 is propyl, and -^ is halogen.
7. The com ound of claim 6 in which is bromine. are ethyl. 10. The compound of claim 2 in which R2 and R4 are ethyl and R-j_ is bromine. 11. The compound of claim 2 in which R2 and R4 are propyl and is bromine. 12. The compound of claim 2 in which ^ is methyl, R2 is ethyl, and R-^ is bromine. 13. The compound of claim 1 in which R2 and R4 are alkyl and R-^ is nitro. 14. The compound of claim 13 in which R^ is methyl and R2 is ethyl. 15. The compound of claim 1 in which R^ is phenyl, R2 is alkyl and R^ is H. 16. The compound of claim 15 in which R2 is methyl. 17. The compound of claim 1 in which R^ is alkyl, R2 is alkylamino and R^ is halogen. 18. The compound of claim 17 in which R^ is methyl, R2 is butylamino and R^ is bromine. 19. The compound of claim 1 in which R^ is alkyl, R2 is dialkylamino , and R-^ is H. 20. The compound of claim 19 in which R^ is methyl and R2 is diethylamino . 21. The compound of claim 1 in which R^ is alkyl, R2 is alkylamino and R-^ is H. 22. The compound of claim 21 in which R^ is methyl and R2 is octylamino. 23. The compound of claim 1 in which R^ is alkyl,' R2 is substituted amino and R-^ is halogen. 24. The compound of claim 23 in which ^ is methyl, R2 is dialkoxyalkylamino , and R^ is bromine. 40895/2 25. The compound of claim 24 in which R2 is dimethoxyethylamino . 26. The compound of claim 1 in which is alkyl, R2 is piperidino > and R^ is H. 27. The compound of, claim 26 in which' 4 is methyl and R is piperidino. 28. The compound of claim 1 in which R^ is alkyl, R2 is substituted amino -a d_. ^ _is H. 29. The compound of claim 28 in which R4 is methyl and 2 is hydroxyalkylamino. 20. The compound of claim 29 in which 2 is hydro-xyeth lamino. 31. The compound of claim 1 in which R-^ is ethyl. 32. The compound of claim 31 in which R2 and R4 are methyl. 33. The compound of claim 31 in which ^ is methyl and 2 is alkylamino. 34. The compound of claim 33 in which R2 is propylamino. 35. The compound of -claim 31 in which 4 is methyl and R2 is propoxy. 36. The compound of claim 31 in which R4 is methyl and R2 is ethylthio. 37. The compound of claim 31 in which R^ is car-bethoxy and 2 is dialkylhydrazino. 38. The compound of claim 31 in which ^ is carbe-thoxy and R2 is propylamino. 39. The compound of claim 31 in which R3 is car-bethoxy and R2 is propoxy . 40. The compound of claim 31 in which R3 is 40895/2 '4· carbethoxy and R_ is -eihylthio. The compound of claim 31 in which 3 is ethoxy. The compound of claim 41 in which R» is propoxy , 43. The compound of claim 41 in which R is ethylthio. 44. The compound of claim 41 in which R9 is.N-glycine.. The compound of claim 41 in which R N—β-alanixie . The compound of claim 51 in which R is hydroxy and R. is methyl. 47. The- compound of claim 51 in which R? is chloro and R, is methyl. Die compound of claim 51 in which R2 is chloro and R, is carbethoxy. 5 - 49. The compound of claim 51 in which R≥ is chloro and R, is ethoxy. 5 50. The compound of claim 1 in which R^ is carbethoxy. 51. The compound of claim 50 in which is hydrogen and R2 is MO^. 52. The compound of claim 50 in which R^ is bromine and R2 is N(C^)2» 55. The compound of claim 0 in which R. is 40895/2 halogen and Eg Is alkylthlo. „^ 54. The compound of claim 3 in which R^ is bro¬ is hydro¬ is halogen and R2 is alkylamino. 57. The compound of claim 56 in which R^ is bromine and Rg is HHC^. 53. She compound of claim 56 in which is bromine and R2 is SHC^El^. 59. The compound of claim 50 in which ^ is hydr-gen and R2 is alkylthlo. 60. The compound of claim 59 in which g is 61. The compound of claim 50 in which is haloge and 2 Is BH(CH2)n0H. 62. She compound of claim 61 in which ^ is bromine and n is 2. 63· She process of preparing 3»5>7 or 3»6,7-trlsubstitutedpyrazolo[lr5^pyrimidines as claimed in Claim 1 from 3-aminopyrazole derivatives by reaction with symmetrical β-diketones, unsymmetrical 0-diketones, β-ketoesters, ethyl ethoxymethylene cyanoacetate, diethyl ethoxymethylenemalonate and a-formyl carboxyllc esters. 64. fho process of claim 63 in which the 3-unsubstituted compounds are treated wit electrophilic reagents to obtain additional 3»5»7 and 3#5,7-trisubstituted-pyrazolo[l,5a]pyrimidines as claimed in Claim 1. 65. S e process of claim 63 in which 7-0H sub-stituted compounds are treated with phosphorus oxchloride 40895/2 to obtain 7-chloro-3,5 or 3»6-disubatitutedpyrazolo[lf5a] pyrimidines. 66. 5he process of claim 65 in which the 7-chloro compounds are further treated with nucleophilic reagents to obtain additional 3»5»7 or 3f6#7 trisubstitutedpyra¾olo [l,5a]pyrimidines, as claimed in Claim 1. For the Applicants BD/rz
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 (2)
Publication Number | Publication Date |
---|---|
IL40895A0 IL40895A0 (en) | 1973-01-30 |
IL40895A true IL40895A (en) | 1976-12-31 |
Family
ID=27498614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL40895A IL40895A (en) | 1971-12-09 | 1972-11-22 | Pyrazolo(1,5a)pyrimidines and their preparation |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS4864097A (en) |
BE (1) | BE792533A (en) |
BG (1) | BG22401A3 (en) |
CH (1) | CH603652A5 (en) |
DD (1) | DD104530A5 (en) |
DE (1) | DE2257547A1 (en) |
GB (1) | GB1412017A (en) |
HU (1) | HU168530B (en) |
IE (1) | IE37189B1 (en) |
IL (1) | IL40895A (en) |
LU (1) | LU66597A1 (en) |
NL (1) | NL7216539A (en) |
NO (1) | NO137012C (en) |
RO (1) | RO62762A (en) |
SE (1) | SE398751B (en) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4281000A (en) * | 1979-07-09 | 1981-07-28 | American Cyanamid Company | Substituted pyrazolo (1,5-a)pyrimidines and their use as anxiolytic agents |
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 |
NZ208554A (en) * | 1983-06-23 | 1987-06-30 | American Cyanamid Co | (aryl and heteroaryl)-(7-(aryl and heteroaryl)-pyrazolo (1,5-a) pyrimidin-3-yl)-methanone derivatives and pharmaceutical compositions |
DE3533050A1 (en) * | 1985-09-17 | 1987-03-26 | Basf Ag | 7-AMINO-AZOLO (1,5-A) PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM, OR THEIR USE AS FUNGICIDES |
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 |
WO1992018504A1 (en) * | 1991-04-22 | 1992-10-29 | Otsuka Pharmaceutical Factory, Inc. | PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND ANTI-INFLAMMATORY CONTAINING THE SAME |
DE4333705C2 (en) * | 1993-10-02 | 2003-10-30 | Guenter Ege | Arylmethyl-substituted pyrazolo-azines, in particular 3-arylmethylpyrazolo [1,5-a] pyrimidines and process for the preparation of 8-arylmethylpyrazolo [5,1-c] [1,2,4] triazines |
PT714898E (en) * | 1994-06-21 | 2002-04-29 | Otsuka Pharma Co Ltd | PYRAZOLONE-1,5-A | PYRIMIDINE DERIVATIVES |
EP0795555A4 (en) * | 1995-09-28 | 1998-01-07 | Otsuka Pharma Co Ltd | Analgesics |
FR2771631B1 (en) * | 1997-12-03 | 2001-02-02 | Oreal | KERATINIC FIBER DYE COMPOSITIONS CONTAINING 3-AMINO PYRAZOLO- [1,5-A] -PYRIMIDINES, DYEING PROCESS, NEW 3-AMINO PYRAZOLO- [1,5-A] -PYRIMIDINES AND THE PROCESS FOR THE PREPARATION |
US7161003B1 (en) | 2002-09-04 | 2007-01-09 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
WO2004022561A1 (en) * | 2002-09-04 | 2004-03-18 | Schering Corporation | Pyrazolopyrimidines as cyclin-dependent kinase inhibitors |
US7119200B2 (en) * | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
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 |
ES2222813B1 (en) * | 2003-07-24 | 2005-12-16 | Ferrer Internacional, S.A. | N- (3- (3-SUBSTITUTES-PIRAZOLO (1,5-A) PIRIMIDIN-7-IL) -PENYL) -SULPHONAMIDS AND RELATED COMPOSITIONS AND METHODS |
HUE031980T2 (en) | 2013-04-25 | 2017-08-28 | Beigene Ltd | Fused heterocyclic compounds as protein kinase inhibitors |
HUE049281T2 (en) | 2013-09-13 | 2020-09-28 | Beigene Switzerland Gmbh | Anti-pd1 antibodies and their use as therapeutics and diagnostics |
WO2016000619A1 (en) | 2014-07-03 | 2016-01-07 | Beigene, Ltd. | Anti-pd-l1 antibodies and their use as therapeutics and diagnostics |
EP3481393B1 (en) | 2016-07-05 | 2021-04-14 | Beigene, Ltd. | Combination of a pd-1 antagonist and a raf inhibitor for treating cancer |
TW202233628A (en) | 2016-08-16 | 2022-09-01 | 英屬開曼群島商百濟神州有限公司 | Crystalline form of (s)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide, preparation, and uses thereof |
FI3500299T3 (en) | 2016-08-19 | 2024-02-14 | Beigene Switzerland Gmbh | Combination of zanubrutinib with an anti-cd20 or an anti-pd-1 antibody for use in treating cancer |
US11555038B2 (en) | 2017-01-25 | 2023-01-17 | Beigene, Ltd. | Crystalline forms of (S)-7-(1-(but-2-ynoyl)piperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide, preparation, and uses thereof |
US11597768B2 (en) | 2017-06-26 | 2023-03-07 | Beigene, Ltd. | Immunotherapy for hepatocellular carcinoma |
WO2019034009A1 (en) | 2017-08-12 | 2019-02-21 | Beigene, Ltd. | Btk INHIBITORS WITH IMPROVED DUAL 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 |
US11786531B1 (en) | 2022-06-08 | 2023-10-17 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
-
0
- BE BE792533D patent/BE792533A/en unknown
-
1972
- 1972-11-21 IE IE1612/72A patent/IE37189B1/en unknown
- 1972-11-22 IL IL40895A patent/IL40895A/en unknown
- 1972-11-23 DE DE2257547A patent/DE2257547A1/en active Pending
- 1972-12-01 GB GB5558772A patent/GB1412017A/en not_active Expired
- 1972-12-05 SE SE7215829A patent/SE398751B/en unknown
- 1972-12-05 LU LU66597A patent/LU66597A1/xx unknown
- 1972-12-06 CH CH1775172A patent/CH603652A5/xx not_active IP Right Cessation
- 1972-12-06 NO NO4476/72A patent/NO137012C/en unknown
- 1972-12-06 NL NL7216539A patent/NL7216539A/xx not_active Application Discontinuation
- 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 BG BG22071A patent/BG22401A3/xx unknown
- 1972-12-09 RO RO7200073093A patent/RO62762A/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE792533A (en) | 1973-06-08 |
CH603652A5 (en) | 1978-08-31 |
SE398751B (en) | 1978-01-16 |
JPS4864097A (en) | 1973-09-05 |
DD104530A5 (en) | 1974-03-12 |
RO62762A (en) | 1978-05-15 |
LU66597A1 (en) | 1973-03-15 |
GB1412017A (en) | 1975-10-29 |
IL40895A0 (en) | 1973-01-30 |
BG22401A3 (en) | 1977-02-20 |
DE2257547A1 (en) | 1973-06-14 |
IE37189L (en) | 1973-06-09 |
IE37189B1 (en) | 1977-05-25 |
NO137012C (en) | 1977-12-14 |
HU168530B (en) | 1976-05-28 |
NO137012B (en) | 1977-09-05 |
NL7216539A (en) | 1973-06-13 |
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