GB884151A - New pyrazolo-pyrimidines substituted in the pyrazole nucleus, and process for their manufacture - Google Patents
New pyrazolo-pyrimidines substituted in the pyrazole nucleus, and process for their manufactureInfo
- Publication number
- GB884151A GB884151A GB39321/58A GB3932158A GB884151A GB 884151 A GB884151 A GB 884151A GB 39321/58 A GB39321/58 A GB 39321/58A GB 3932158 A GB3932158 A GB 3932158A GB 884151 A GB884151 A GB 884151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidine
- cyano
- alkyl
- carbon atoms
- amino group
- 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
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical group N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000003217 pyrazoles Chemical class 0.000 title 1
- -1 methylmercapto Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000003277 amino group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical class OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 abstract 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical class NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 abstract 1
- WKWJLPHVJAUOLS-UHFFFAOYSA-N 4-chloro-2-(dimethylamino)pyrimidine-5-carbonitrile Chemical compound CN(C)C1=NC=C(C#N)C(Cl)=N1 WKWJLPHVJAUOLS-UHFFFAOYSA-N 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004475 Arginine Substances 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 abstract 1
- 150000000994 L-ascorbates Chemical class 0.000 abstract 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 abstract 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004472 Lysine Substances 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- BKZPYUYMGJRKFT-UHFFFAOYSA-N O1CCN(CC1)C1=NC=C(C(=N1)Cl)C#N Chemical compound O1CCN(CC1)C1=NC=C(C(=N1)Cl)C#N BKZPYUYMGJRKFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000006035 Tryptophane Substances 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical class 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
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000003893 lactate salts Chemical class 0.000 abstract 1
- 150000004701 malic acid derivatives Chemical class 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 229930182817 methionine Natural products 0.000 abstract 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 150000003891 oxalate salts Chemical class 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 abstract 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 abstract 1
- 150000003873 salicylate salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003890 succinate salts Chemical class 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 150000003892 tartrate salts Chemical class 0.000 abstract 1
- 229960004799 tryptophan Drugs 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0884151/IV (b)/1> or <FORM:0884151/IV (b)/2> and acid addition salts thereof, wherein R2 is a saturated hydrocarbon radical of up to 6 carbon atoms, e.g. alkyl and R3 is an amino group optionally substituted by one or two aliphatic radicals of 1-6 carbon atoms or a heterocyclic amino group. The compounds are prepared by reacting a 2-R3-4-halo-5-cyano-pyrimidine with a hydrazine R2NH.NH2. The products are used pharmaceutically, suitably in the form of acid addition salts (see Group VI). Examples describe the preparation of 1- or 2-isopropyl-6-dimethylamino-;1-methyl-6-morpholino- and 1- and 2-pentyl-(21)-6-dimethylamino-, pyrazolo-[3 : 4-d]-pyrimidine. 2 - substituted - 4 - halo - 5 - cyano - pyrimidines used as starting materials, e.g. 2-dimethylamino-4-chloro-5-cyano-pyrimidine and 2-morpholino-4-chloro-5-cyanopyrimidine are made by reacting an a -ethoxymethylene-a -cyanacetic ester with an S-alkyl-isothiourea to give 2-alkyl-mercapto (e.g. methylmercapto) - 4 - hydroxy - 5 - cyano - pyrimidine which is reacted with an amine such as dimethylamine or morpholine to give a 2-substituted-4-hydroxy-5-cyano-pyrimidine which is treated with phosphorus oxychloride. S-methylisothioureido-methylene cyanoacetic ester is obtained as the initial product of the condensation of a -ethoxymethylene-a -cyanoacetic ester and S-methylisothiourea.ALSO:Pharmaceutical preparations having tumour inhibiting, diuretic, coronary-dilating, central nervous system inhibiting and anti-rheumatic effects and acting as anti-metabolites of purine comprise pyrazolo-pyrimidine compounds of the formula <FORM:0884151/VI/1> or <FORM:0884151/VI/2> or acid addition salts thereof, wherein R2 is a saturated hydrocarbon radical of up to 6 carbon atoms, e.g. alkyl and R3 is an amino group optionally substituted by one or two aliphatic radicals of 1-6 carbon atoms or a heterocyclic amino group (see Group IV (b) in admixture or association with a pharmaceutical carrier. The preparations suitably take the form of solutions, suspensions, emulsions, tablets or dragees and may contain auxiliary substances such as stabilizing, wetting or emulsifying agents. Specified salts are hydrohalides, sulphates, phosphates, nitrates, perchlorates, formates, acetates, propionates, oxalates, succinates, glycollates, lactates, malates, tartrates, citrates, ascorbates, mono- and di-hydroxymaleates, pyruvates, phenylacetates, benzoates, p-aminobenzoates, anthranilates, p-hydroxybenzoates, salicylates, p - aminosalicylates, methane-, ethane -, ethylene -, hydroxyethane -, toluene-and naphthalene-sulphonates, sulphanilates and salts with methionine, lysine, tryptophane and arginine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH884151X | 1957-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB884151A true GB884151A (en) | 1961-12-06 |
Family
ID=4545117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39321/58A Expired GB884151A (en) | 1957-12-06 | 1958-12-05 | New pyrazolo-pyrimidines substituted in the pyrazole nucleus, and process for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB884151A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2145888A1 (en) | 2003-09-18 | 2010-01-20 | Conforma Therapeutics Corporation | Deazapurine derivatives as HSP90-Inhibitors |
| JP2021516231A (en) * | 2018-02-28 | 2021-07-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド，ア ボディー コーポレイトＴＨＥ ＲＥＧＥＮＴＳ ＯＦ ＴＨＥ ＵＮＩＶＥＲＳＩＴＹ ＯＦ ＣＯＬＯＲＡＤＯ，ａ ｂｏｄｙ ｃｏｒｐｏｒａｔｅ | WEE1 kinase inhibitor and how to treat cancer with it |
-
1958
- 1958-12-05 GB GB39321/58A patent/GB884151A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2145888A1 (en) | 2003-09-18 | 2010-01-20 | Conforma Therapeutics Corporation | Deazapurine derivatives as HSP90-Inhibitors |
| JP2021516231A (en) * | 2018-02-28 | 2021-07-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド，ア ボディー コーポレイトＴＨＥ ＲＥＧＥＮＴＳ ＯＦ ＴＨＥ ＵＮＩＶＥＲＳＩＴＹ ＯＦ ＣＯＬＯＲＡＤＯ，ａ ｂｏｄｙ ｃｏｒｐｏｒａｔｅ | WEE1 kinase inhibitor and how to treat cancer with it |
| US12220415B2 (en) | 2018-02-28 | 2025-02-11 | The Regents Of The University Of Colorado, A Body Corporate | WEE1 kinase inhibitors and methods of treating cancer using the same |
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