IE37189L - PYRAZOLO [1,5-a] PYRIMIDINES - Google Patents
PYRAZOLO [1,5-a] PYRIMIDINESInfo
- Publication number
- IE37189L IE37189L IE721612A IE161272A IE37189L IE 37189 L IE37189 L IE 37189L IE 721612 A IE721612 A IE 721612A IE 161272 A IE161272 A IE 161272A IE 37189 L IE37189 L IE 37189L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- effect
- pyrazolo
- compounds
- dec
- 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)
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]
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 true IE37189L (en) | 1973-06-09 |
IE37189B1 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)
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 |
AU651986B2 (en) * | 1991-04-22 | 1994-08-11 | 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 |
CN1046730C (en) * | 1994-06-21 | 1999-11-24 | 株式会社大塚制药工场 | Pyrazolo [1,5-a] pyrimidine derivative |
KR100260292B1 (en) * | 1995-09-28 | 2000-07-01 | 오쓰카 요시미쓰 | 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 |
US7161003B1 (en) | 2002-09-04 | 2007-01-09 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
DK1537116T3 (en) * | 2002-09-04 | 2010-09-27 | Schering Corp | Pyrazolopyrimidines suitable for the treatment of cancer diseases |
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 |
LT2989106T (en) | 2013-04-25 | 2017-04-10 | Beigene, Ltd. | Fused heterocyclic compounds as protein kinase inhibitors |
RS63571B9 (en) | 2013-09-13 | 2023-02-28 | Beigene Switzerland Gmbh | Anti-pd1 antibodies and their use as therapeutics and diagnostics |
KR102130600B1 (en) | 2014-07-03 | 2020-07-08 | 베이진 엘티디 | 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 |
TWI760356B (en) | 2016-08-16 | 2022-04-11 | 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 |
EP3500299B1 (en) | 2016-08-19 | 2023-12-13 | BeiGene Switzerland GmbH | Combination of zanubrutinib with an anti-cd20 or an anti-pd-1 antibody for use in treating cancer |
TWI774726B (en) | 2017-01-25 | 2022-08-21 | 英屬開曼群島商百濟神州有限公司 | 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 |
TW201906866A (en) | 2017-06-26 | 2019-02-16 | 英屬開曼群島商百濟神州有限公司 | Treatment of abnormal bone condition in patients with acid sphingomyelinase deficiency |
WO2019034009A1 (en) | 2017-08-12 | 2019-02-21 | Beigene, Ltd. | Btk INHIBITORS WITH IMPROVED DUAL SELECTIVITY |
WO2019108795A1 (en) | 2017-11-29 | 2019-06-06 | 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 LU LU66597A patent/LU66597A1/xx unknown
- 1972-12-05 SE SE7215829A patent/SE398751B/en 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 BG BG22071A patent/BG22401A3/xx unknown
- 1972-12-09 RO RO7200073093A patent/RO62762A/en unknown
- 1972-12-09 JP JP47123877A patent/JPS4864097A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
RO62762A (en) | 1978-05-15 |
DD104530A5 (en) | 1974-03-12 |
IE37189B1 (en) | 1977-05-25 |
JPS4864097A (en) | 1973-09-05 |
IL40895A0 (en) | 1973-01-30 |
NL7216539A (en) | 1973-06-13 |
NO137012C (en) | 1977-12-14 |
IL40895A (en) | 1976-12-31 |
HU168530B (en) | 1976-05-28 |
BE792533A (en) | 1973-06-08 |
LU66597A1 (en) | 1973-03-15 |
CH603652A5 (en) | 1978-08-31 |
BG22401A3 (en) | 1977-02-20 |
NO137012B (en) | 1977-09-05 |
GB1412017A (en) | 1975-10-29 |
DE2257547A1 (en) | 1973-06-14 |
SE398751B (en) | 1978-01-16 |
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