GB1412017A - Pyrazolo 1,5a pyrimidines - Google Patents
Pyrazolo 1,5a pyrimidinesInfo
- Publication number
- GB1412017A GB1412017A GB5558772A GB5558772A GB1412017A GB 1412017 A GB1412017 A GB 1412017A GB 5558772 A GB5558772 A GB 5558772A GB 5558772 A GB5558772 A GB 5558772A GB 1412017 A GB1412017 A GB 1412017A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- effect
- pyrazolo
- compounds
- dec
- 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.)
- Expired
Links
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 206010021118 Hypotonia Diseases 0.000 abstract 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 abstract 1
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000003501 anti-edematous effect Effects 0.000 abstract 1
- 239000002579 antinauseant Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 230000005792 cardiovascular activity Effects 0.000 abstract 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 abstract 1
- -1 dicarbonyl compound Chemical class 0.000 abstract 1
- 230000010339 dilation Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000036640 muscle relaxation Effects 0.000 abstract 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 231100000397 ulcer Toxicity 0.000 abstract 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 |
---|---|
GB1412017A true GB1412017A (en) | 1975-10-29 |
Family
ID=27498614
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5558772A Expired GB1412017A (en) | 1971-12-09 | 1972-12-01 | Pyrazolo 1,5a pyrimidines |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS4864097A (de) |
BE (1) | BE792533A (de) |
BG (1) | BG22401A3 (de) |
CH (1) | CH603652A5 (de) |
DD (1) | DD104530A5 (de) |
DE (1) | DE2257547A1 (de) |
GB (1) | GB1412017A (de) |
HU (1) | HU168530B (de) |
IE (1) | IE37189B1 (de) |
IL (1) | IL40895A (de) |
LU (1) | LU66597A1 (de) |
NL (1) | NL7216539A (de) |
NO (1) | NO137012C (de) |
RO (1) | RO62762A (de) |
SE (1) | SE398751B (de) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2523582A1 (fr) * | 1982-03-16 | 1983-09-23 | Erba Farmitalia | Nouvelles 1h-pyrazolo(1,5-a)pyrimidines substituees, utiles notamment comme medicaments anti-inflammatoires et analgesiques, et procede pour leur preparation |
FR2523972A1 (fr) * | 1982-03-25 | 1983-09-30 | Erba Farmitalia | Derives vinyliques substitues de la 1h-pyrazolo-(1,5-a) pyrimidine utiles notamment comme medicaments antiulcerigenes et antisecretoires gastriques et procede de leur preparation |
EP0369145A2 (de) * | 1988-10-13 | 1990-05-23 | Pola Chemical Industries Inc., Japan | Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel |
WO2005014596A1 (en) * | 2003-07-24 | 2005-02-17 | Ferrer Internacional, S.A. | 7-substituted 3-nitro-pyrazolo `1,5-a! pyrimidines |
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 |
AU2003263071B2 (en) * | 2002-09-04 | 2007-03-15 | Merck Sharp & Dohme Llc | Pyrazolopyrimidines as cyclin-dependent kinase inhibitors |
CN100393721C (zh) * | 2003-07-24 | 2008-06-11 | 菲尔若国际公司 | N-[3-(3-取代的-吡唑并[1,5-a]嘧啶-7-基)苯基]-磺酰胺类及其组合物和相关方法 |
US10570139B2 (en) | 2013-04-25 | 2020-02-25 | Beigene Switzerland Gmbh | Substituted pyrazolo[1,5-a]pyrimidines as Bruton's tyrosine kinase modulators |
US10927117B2 (en) | 2016-08-16 | 2021-02-23 | Beigene Switzerland Gmbh | 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 |
US11186637B2 (en) | 2013-09-13 | 2021-11-30 | Beigene Switzerland Gmbh | Anti-PD1 antibodies and their use as therapeutics and diagnostics |
US11377449B2 (en) | 2017-08-12 | 2022-07-05 | Beigene, Ltd. | BTK inhibitors with improved dual selectivity |
US11512132B2 (en) | 2014-07-03 | 2022-11-29 | Beigene, Ltd. | Anti-PD-L1 antibodies and their use as therapeutics and diagnostics |
US11534431B2 (en) | 2016-07-05 | 2022-12-27 | Beigene Switzerland Gmbh | Combination of a PD-1 antagonist and a RAF inhibitor for 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 |
US11701357B2 (en) | 2016-08-19 | 2023-07-18 | Beigene Switzerland Gmbh | Treatment of B cell cancers using a combination comprising Btk inhibitors |
US11786531B1 (en) | 2022-06-08 | 2023-10-17 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
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 |
Families Citing this family (8)
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 |
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 (de) * | 1985-09-17 | 1987-03-26 | Basf Ag | 7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide, bzw. deren verwendung als fungizide |
DK0591528T3 (da) * | 1991-04-22 | 1999-08-23 | Otsuka Pharma Co Ltd | Pyrazolo[1,5-a]pyrimidinderivat og antiinflammatorisk middel, der indeholder dette |
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 |
ES2164153T3 (es) * | 1994-06-21 | 2002-02-16 | Otsuka Pharma Co Ltd | Derivado de pirazolo(1,5-a)pirimidina. |
WO1997011946A1 (fr) * | 1995-09-28 | 1997-04-03 | Otsuka Pharmaceutical Factory, Inc. | Analgesiques |
FR2771631B1 (fr) * | 1997-12-03 | 2001-02-02 | 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 |
-
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 SE SE7215829A patent/SE398751B/xx unknown
- 1972-12-05 LU LU66597A patent/LU66597A1/xx unknown
- 1972-12-06 NL NL7216539A patent/NL7216539A/xx not_active Application Discontinuation
- 1972-12-06 NO NO4476/72A patent/NO137012C/no unknown
- 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 BG BG022071A patent/BG22401A3/xx unknown
- 1972-12-09 RO RO7200073093A patent/RO62762A/ro unknown
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2523582A1 (fr) * | 1982-03-16 | 1983-09-23 | Erba Farmitalia | Nouvelles 1h-pyrazolo(1,5-a)pyrimidines substituees, utiles notamment comme medicaments anti-inflammatoires et analgesiques, et procede pour leur preparation |
FR2523972A1 (fr) * | 1982-03-25 | 1983-09-30 | Erba Farmitalia | Derives vinyliques substitues de la 1h-pyrazolo-(1,5-a) pyrimidine utiles notamment comme medicaments antiulcerigenes et antisecretoires gastriques et procede de leur preparation |
EP0369145A2 (de) * | 1988-10-13 | 1990-05-23 | Pola Chemical Industries Inc., Japan | Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel |
EP0369145A3 (de) * | 1988-10-13 | 1991-07-17 | Pola Chemical Industries Inc., Japan | Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel |
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 |
AU2003263071B2 (en) * | 2002-09-04 | 2007-03-15 | Merck Sharp & Dohme Llc | Pyrazolopyrimidines as cyclin-dependent kinase inhibitors |
US7807683B2 (en) | 2002-09-04 | 2010-10-05 | Schering Corporation | N-heteroaryl pyrazolopyrimidines as cyclin dependent kinase inhibitors |
WO2005014596A1 (en) * | 2003-07-24 | 2005-02-17 | Ferrer Internacional, S.A. | 7-substituted 3-nitro-pyrazolo `1,5-a! pyrimidines |
CN100393721C (zh) * | 2003-07-24 | 2008-06-11 | 菲尔若国际公司 | N-[3-(3-取代的-吡唑并[1,5-a]嘧啶-7-基)苯基]-磺酰胺类及其组合物和相关方法 |
AU2005212409B2 (en) * | 2004-02-11 | 2011-12-01 | Merck Sharp & Dohme Llc | Pyrazolopyrimidine-derivatives as cyclin dependent kinase inhibitors |
AU2005212409C1 (en) * | 2004-02-11 | 2012-07-19 | Merck Sharp & Dohme Llc | Pyrazolopyrimidine-derivatives as cyclin dependent kinase inhibitors |
US11142528B2 (en) | 2013-04-25 | 2021-10-12 | Beigene Switzerland Gmbh | Substituted pyrazolo[1,5-a]pyrimidines as Bruton's tyrosine kinase modulators |
US10570139B2 (en) | 2013-04-25 | 2020-02-25 | Beigene Switzerland Gmbh | Substituted pyrazolo[1,5-a]pyrimidines as Bruton's tyrosine kinase modulators |
US11673951B2 (en) | 2013-09-13 | 2023-06-13 | Beigene Switzerland Gmbh | Anti-PD1 antibodies and their use as therapeutics and diagnostics |
US11186637B2 (en) | 2013-09-13 | 2021-11-30 | Beigene Switzerland Gmbh | Anti-PD1 antibodies and their use as therapeutics and diagnostics |
US11512132B2 (en) | 2014-07-03 | 2022-11-29 | Beigene, Ltd. | Anti-PD-L1 antibodies and their use as therapeutics and diagnostics |
US11534431B2 (en) | 2016-07-05 | 2022-12-27 | Beigene Switzerland Gmbh | Combination of a PD-1 antagonist and a RAF inhibitor for treating cancer |
US11999743B2 (en) | 2016-08-16 | 2024-06-04 | Beigene Switzerland Gmbh | 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 |
US11591340B2 (en) | 2016-08-16 | 2023-02-28 | Beigene Switzerland Gmbh | 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 |
US11970500B1 (en) | 2016-08-16 | 2024-04-30 | Beigene Switzerland Gmbh | 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 |
US12103931B2 (en) | 2016-08-16 | 2024-10-01 | Beigene Switzerland Gmbh | 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 |
US10927117B2 (en) | 2016-08-16 | 2021-02-23 | Beigene Switzerland Gmbh | 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 |
US11814389B2 (en) | 2016-08-16 | 2023-11-14 | Beigene Switzerland Gmbh | 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 |
US11851437B2 (en) | 2016-08-16 | 2023-12-26 | Beigene Switzerland Gmbh | 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 |
US11884674B2 (en) | 2016-08-16 | 2024-01-30 | Beigene Switzerland Gmbh | 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 |
US11701357B2 (en) | 2016-08-19 | 2023-07-18 | Beigene Switzerland Gmbh | Treatment of B cell cancers using a combination 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 |
US11597768B2 (en) | 2017-06-26 | 2023-03-07 | Beigene, Ltd. | Immunotherapy for hepatocellular carcinoma |
US11377449B2 (en) | 2017-08-12 | 2022-07-05 | 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 |
US11911386B2 (en) | 2022-06-08 | 2024-02-27 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
US11896596B2 (en) | 2022-06-08 | 2024-02-13 | Beigene Switzerland Gmbh | Methods of treating B-cell proliferative disorder |
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 (sv) | 1978-01-16 |
LU66597A1 (de) | 1973-03-15 |
IE37189B1 (en) | 1977-05-25 |
CH603652A5 (de) | 1978-08-31 |
HU168530B (de) | 1976-05-28 |
IL40895A0 (en) | 1973-01-30 |
BG22401A3 (bg) | 1977-02-20 |
DE2257547A1 (de) | 1973-06-14 |
DD104530A5 (de) | 1974-03-12 |
BE792533A (fr) | 1973-06-08 |
NO137012C (no) | 1977-12-14 |
NL7216539A (de) | 1973-06-13 |
IE37189L (en) | 1973-06-09 |
RO62762A (fr) | 1978-05-15 |
NO137012B (no) | 1977-09-05 |
IL40895A (en) | 1976-12-31 |
JPS4864097A (de) | 1973-09-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |