IE37189B1 - Pyrazolo (1,5a) pyrimidines - Google Patents

Pyrazolo (1,5a) pyrimidines

Info

Publication number
IE37189B1
IE37189B1 IE1612/72A IE161272A IE37189B1 IE 37189 B1 IE37189 B1 IE 37189B1 IE 1612/72 A IE1612/72 A IE 1612/72A IE 161272 A IE161272 A IE 161272A IE 37189 B1 IE37189 B1 IE 37189B1
Authority
IE
Ireland
Prior art keywords
alkyl
effect
pyrazolo
compounds
dec
Prior art date
Application number
IE1612/72A
Other versions
IE37189L (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 IE37189L publication Critical patent/IE37189L/en
Publication of IE37189B1 publication Critical patent/IE37189B1/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)

Abstract

1412017 Pyrazolo[1,5-a]pyrimidines ICN PHARMACEUTICALS Inc 1 Dec 1972 [9 Dec 1971 20 April 1972 20 July 1972 24 Oct 1972] 55587/72 Heading C2C The invention comprises compounds of formula wherein R 1 is H, alkoxycarbonyl, alkyl, CN, halogen, carbamoyl, acyl, aminomethyl, dialkylaminomethyl, N0 2 , NH 2 or AcNH; R 2 is alkyl, alkoxy (C 1-8 ), alkylthio (C 1-6 ), SH, cyclic amino or NH 2 (mono- or di-alkyl or otherwise substituted); R 3 is H; and R 4 is H, alkyl or Ph, provided that if (i) R 2 =R 4 =Me, then R 1 is not H or CO 2 Et; (ii) R 4 =Me and R 2 =MeO or EtO, then R 1 is not H; (iii) R 2 = Me, then R 4 and R 1 are not both H, and (iv) R 2 = N 2 H 3 and R 4 = Ph, then R 1 is not H. In examples, these compounds are prepared by reacting a 3-amino-4- R 1 -pyrazole with the dicarbonyl compound R 4 COCH 2 COR 2 , or using standard procedures to introduce into, or to modify or change a substituent element or group in, a preformed pyrazolo-pyrimidine (e.g. one containing a 7-Cl or 7-HO substituent). Also prepared is the starting material EtCH(CN)CHO. Therapeutic compositions having phosphodiesterase enzyme-inhibiting activity, and which in certain cases produce ADP-induced platelet aggregation inhibition and antinauseant or antipregnancy effect, or anti-oedema effect, muscle relaxation, inhibition of ulcer formation, a positive isotropic effect on the heart, an anticonvulsant effect, lowered blood pressure, coronary dilation and/or other cardiovascular activity, comprise compounds of the above formula. The oral and parenteral routes of administration are mentioned. [GB1412017A]
IE1612/72A 1971-12-09 1972-11-21 Pyrazolo (1,5a) pyrimidines IE37189B1 (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
IE37189L IE37189L (en) 1973-06-09
IE37189B1 true IE37189B1 (en) 1977-05-25

Family

ID=27498614

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1612/72A IE37189B1 (en) 1971-12-09 1972-11-21 Pyrazolo (1,5a) pyrimidines

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
EP0591528B1 (en) * 1991-04-22 1998-12-23 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
EP0714898B1 (en) * 1994-06-21 2001-11-14 Otsuka Pharmaceutical Factory, Inc. PYRAZOLO [1,5-a]PYRIMIDINE DERIVATIVE
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
AU2003263071B2 (en) * 2002-09-04 2007-03-15 Merck Sharp & Dohme Llc 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
NZ711540A (en) 2013-04-25 2018-08-31 Beigene Ltd Fused heterocyclic compounds as protein kinase inhibitors
BR112016005408B1 (en) 2013-09-13 2023-03-21 Beigene Switzerland Gmbh ANTI-PD1, F(AB) OR F(AB)2 ANTIBODIES AND REFERRED USE ANTIBODY FOR TREATMENT OF CANCER OR VIRAL INFECTION
EP3160505A4 (en) 2014-07-03 2018-01-24 BeiGene, Ltd. Anti-pd-l1 antibodies and their use as therapeutics and diagnostics
CN109475536B (en) 2016-07-05 2022-05-27 百济神州有限公司 Combination of a PD-l antagonist and a RAF inhibitor for the treatment of cancer
WO2018033853A2 (en) 2016-08-16 2018-02-22 Beigene, Ltd. Crystalline form of (s)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetra-hydropyrazolo[1,5-a]pyrimidine-3-carboxamide, preparation, and uses thereof
CN110087680B (en) 2016-08-19 2024-03-19 百济神州有限公司 Treatment of cancer using combination products comprising BTK inhibitors
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
WO2019001417A1 (en) 2017-06-26 2019-01-03 Beigene, Ltd. Immunotherapy for hepatocellular carcinoma
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
JPS4864097A (en) 1973-09-05
DD104530A5 (en) 1974-03-12
GB1412017A (en) 1975-10-29
BE792533A (en) 1973-06-08
NO137012C (en) 1977-12-14
RO62762A (en) 1978-05-15
CH603652A5 (en) 1978-08-31
IL40895A (en) 1976-12-31
IL40895A0 (en) 1973-01-30
NL7216539A (en) 1973-06-13
BG22401A3 (en) 1977-02-20
IE37189L (en) 1973-06-09
NO137012B (en) 1977-09-05
HU168530B (en) 1976-05-28
DE2257547A1 (en) 1973-06-14
SE398751B (en) 1978-01-16
LU66597A1 (en) 1973-03-15

Similar Documents

Publication Publication Date Title
IE37189B1 (en) Pyrazolo (1,5a) pyrimidines
IE36947B1 (en) New esters their production and their medicinal use
IE36383L (en) Aryl guanidines
GB1528807A (en) Pyrazolo(1,5-a)pyridines
GB1417104A (en) Imidazo 1,2-a- azacycloalkanes
GB1181146A (en) Bis-Thiosemicarbazones and a process for their manufacture
GB1276968A (en) Improvements in or relating to phenylacetamides and the preparation thereof
IE36623B1 (en) Benzodiazepine dervatives
GB1354431A (en) Thiophene and furan derivatives
GB1361863A (en) Piperazine derivatives their preparation and pharmaceutical compositions containing them
GB1394184A (en) 4,5-dihydropyridazine-3 2h- ones
GB1184826A (en) Substituted Aryloxy Hydroxy Amines
GB1332766A (en) Triazolo-benzodiazepines
IE39926B1 (en) Compositions containing indanyloxyalkanoic acid compounds
GB1362144A (en) Thiophene flavouring agents
GB1437149A (en) Spiro-compounds and a process for their preparation
GB1384523A (en) Oxime derivatives and their preparation
IE33446B1 (en) New isothiocyano-diphenylamines their production and compositions containing same
GB1315287A (en) Thieno-2,3-e 1,4 diazepine compounds methods for their production and pharmaceutical compositions containing them
GB1444558A (en) Pyridylthioureas
GB1329493A (en) N-alkyl-pyridyl-furamides
ES370067A1 (en) 2,6-bis-(dialkanolamino)-pyrimido[5,4-d] pyrimidines
AU585418B2 (en) 6H-isoxazolo`` 3,4-d`` pyrazolo`` 3,4-b`` pyridines,a process for their preparation and their use as medicaments
GB1390602A (en) Benzodiazepine derivatives
IE33192L (en) Quinoxaline-1, 4-dioxides