IL40895A - Pyrazolo(1,5a)pyrimidines and their preparation - Google Patents

Pyrazolo(1,5a)pyrimidines and their preparation

Info

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
Application number
IL40895A
Other versions
IL40895A0 (en
Original Assignee
Icn Pharmaceuticals
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US245870A external-priority patent/US3925385A/en
Application filed by Icn Pharmaceuticals filed Critical Icn Pharmaceuticals
Publication of IL40895A0 publication Critical patent/IL40895A0/en
Publication of IL40895A publication Critical patent/IL40895A/en

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
IL40895A 1971-12-09 1972-11-22 Pyrazolo(1,5a)pyrimidines and their preparation IL40895A (en)

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)

* Cited by examiner, † Cited by third party
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
DK0591528T3 (en) * 1991-04-22 1999-08-23 Otsuka Pharma Co Ltd Pyrazolo [1,5-a] pyrimidine derivative and anti-inflammatory agent containing this
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
ES2164153T3 (en) * 1994-06-21 2002-02-16 Otsuka Pharma Co Ltd DERIVATIVE OF PIRAZOLO (1,5-A) PYRIMIDINE.
WO1997011946A1 (en) * 1995-09-28 1997-04-03 Otsuka Pharmaceutical Factory, Inc. 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
US7119200B2 (en) * 2002-09-04 2006-10-10 Schering Corporation Pyrazolopyrimidines as cyclin dependent kinase inhibitors
KR101088922B1 (en) * 2002-09-04 2011-12-01 파마코페이아, 엘엘씨. Pyrazolopyrimidines as cyclin-dependent kinase inhibitors
US7161003B1 (en) * 2002-09-04 2007-01-09 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
MX367918B (en) 2013-04-25 2019-09-11 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
CN110156892B (en) 2014-07-03 2023-05-16 百济神州有限公司 anti-PD-L1 antibodies and their use as therapeutic and diagnostic agents
WO2018007885A1 (en) 2016-07-05 2018-01-11 Beigene, Ltd. COMBINATION OF A PD-l ANTAGONIST AND A RAF INHIBITOR FOR TREATING CANCER
CN116478166A (en) 2016-08-16 2023-07-25 百济神州(苏州)生物科技有限公司 Crystal form of compound, preparation and application thereof
WO2018033135A1 (en) 2016-08-19 2018-02-22 Beigene, Ltd. Use of a combination comprising a btk inhibitor for treating cancers
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
KR20200020902A (en) 2017-06-26 2020-02-26 베이진 엘티디 Immune treatment for hepatocellular carcinoma (HCC)
WO2019034009A1 (en) 2017-08-12 2019-02-21 Beigene, Ltd. Btk INHIBITORS WITH IMPROVED DUAL SELECTIVITY
CN111801334B (en) 2017-11-29 2023-06-09 百济神州瑞士有限责任公司 Treatment of indolent or invasive B-cell lymphomas using combinations comprising BTK inhibitors
US11786531B1 (en) 2022-06-08 2023-10-17 Beigene Switzerland Gmbh Methods of treating B-cell proliferative disorder

Also Published As

Publication number Publication date
SE398751B (en) 1978-01-16
LU66597A1 (en) 1973-03-15
IE37189B1 (en) 1977-05-25
CH603652A5 (en) 1978-08-31
HU168530B (en) 1976-05-28
IL40895A0 (en) 1973-01-30
BG22401A3 (en) 1977-02-20
DE2257547A1 (en) 1973-06-14
GB1412017A (en) 1975-10-29
DD104530A5 (en) 1974-03-12
BE792533A (en) 1973-06-08
NO137012C (en) 1977-12-14
NL7216539A (en) 1973-06-13
IE37189L (en) 1973-06-09
RO62762A (en) 1978-05-15
NO137012B (en) 1977-09-05
JPS4864097A (en) 1973-09-05

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