IL28248A - Production of pyrazoles and pyrazolopyrimidines - Google Patents

Production of pyrazoles and pyrazolopyrimidines

Info

Publication number: IL28248A
Authority: IL; Israel
Prior art keywords: amino; pyrazole; reaction; carboxamide; preparation
Prior art date: 1966-07-14

Application number

IL28248A

Other languages

English (en)

Hebrew (he)

Original Assignee

Wellcome Found

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.)

1966-07-14

Filing date

1967-07-04

Publication date

1972-04-27

1967-07-04 Application filed by Wellcome Found filed Critical Wellcome Found

1972-04-27 Publication of IL28248A publication Critical patent/IL28248A/en

Links

238000002360 preparation method Methods 0.000 title description 7
150000003217 pyrazoles Chemical class 0.000 title description 3
APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
238000000034 method Methods 0.000 claims description 16
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
LEFSNWUSTYESGC-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carboxamide Chemical compound NC(=O)C1=CNN=C1N LEFSNWUSTYESGC-UHFFFAOYSA-N 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
229960003459 allopurinol Drugs 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 4
FRBZBJHKHSVFNK-UHFFFAOYSA-N 3-amino-2-cyanoprop-2-enamide Chemical compound NC=C(C#N)C(N)=O FRBZBJHKHSVFNK-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229910021653 sulphate ion Inorganic materials 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
201000005569 Gout Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
108010093894 Xanthine oxidase Proteins 0.000 description 2
102100033220 Xanthine oxidase Human genes 0.000 description 2
NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
AQAVZQQASBCQSH-UHFFFAOYSA-N 1H-pyrazole-4-carboxamide sulfuric acid Chemical compound S(=O)(=O)(O)O.N1N=CC(=C1)C(=O)N AQAVZQQASBCQSH-UHFFFAOYSA-N 0.000 description 1
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 1
HGBFVOSZYVRIHY-UHFFFAOYSA-N 2-cyanoprop-2-enamide Chemical compound NC(=O)C(=C)C#N HGBFVOSZYVRIHY-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical compound NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 description 1
-1 Allopurinol Chemical class 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 1
YPXGHKWOJXQLQU-UHFFFAOYSA-N ethyl 5-amino-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1N YPXGHKWOJXQLQU-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL28248A 1966-07-14 1967-07-04 Production of pyrazoles and pyrazolopyrimidines IL28248A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB31690/66A GB1200444A (en)	1966-07-14	1966-07-14	The preparation of pyrazoles and pyrazolopyrimidines

Publications (1)

Publication Number	Publication Date
IL28248A true IL28248A (en)	1972-04-27

Family

ID=10326963

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL28248A IL28248A (en)	1966-07-14	1967-07-04	Production of pyrazoles and pyrazolopyrimidines
IL37439A IL37439A (en)	1966-07-14	1967-07-04	Preparation of 3-amino-2-cyanoacrylamide

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL37439A IL37439A (en)	1966-07-14	1967-07-04	Preparation of 3-amino-2-cyanoacrylamide

Country Status (12)

Country	Link
US (1)	US3487083A (da)
BE (1)	BE701328A (da)
CH (1)	CH485731A (da)
CY (1)	CY693A (da)
DE (2)	DE1720024C3 (da)
DK (2)	DK118666B (da)
FR (1)	FR1559613A (da)
GB (1)	GB1200444A (da)
IL (2)	IL28248A (da)
IT (1)	IT8048941A0 (da)
NL (1)	NL141512B (da)
SE (2)	SE354857B (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1252435A (da) *	1968-02-02	1971-11-03
US3682956A (en) *	1970-06-04	1972-08-08	Graham Arton Howarth	Substituted 3-(5-nitro-2-furyl)-pyrazoles
US3901888A (en) *	1972-02-04	1975-08-26	Hoffmann La Roche	Process for the preparation of 4-amino-2-methylpyrimidine 5-carboxamide
US3864359A (en) *	1972-05-01	1975-02-04	American Cyanamid Co	5-amino-3-ethyl-1-phenyl-4-pyrazolecarboxamides and method of preparation thereof
US4267324A (en) *	1979-06-20	1981-05-12	Polaroid Corporation	Process for preparing 4-aminopyrazolo-(3,4-d)pyrimidine
CN102438994B (zh)	2009-04-08	2015-04-29	帝斯曼知识产权资产管理有限公司	制备嘧啶衍生物的方法
CN102153560A (zh) *	2011-03-07	2011-08-17	江苏红豆杉药业有限公司	一种别嘌醇的精制方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB854632A (en) *	1956-02-10	1960-11-23	Ciba Ltd	Manufacture of pyrazoles
US2868803A (en) *	1956-02-10	1959-01-13	Ciba Pharm Prod Inc	New pyrazoles and method of preparing same
AT200575B (de) *	1957-01-02	1958-11-10	Ciba Geigy	Verfahren zur Herstellung von neuen 3-Amino-pyrazol-derivaten

1966
- 1966-07-14 GB GB31690/66A patent/GB1200444A/en not_active Expired
1967
- 1967-07-04 IL IL28248A patent/IL28248A/en unknown
- 1967-07-04 IL IL37439A patent/IL37439A/en unknown
- 1967-07-06 US US651393A patent/US3487083A/en not_active Expired - Lifetime
- 1967-07-10 CH CH976767A patent/CH485731A/de not_active IP Right Cessation
- 1967-07-12 DE DE1720024A patent/DE1720024C3/de not_active Expired
- 1967-07-12 DE DE19671795720 patent/DE1795720A1/de not_active Withdrawn
- 1967-07-13 DK DK362667AA patent/DK118666B/da not_active IP Right Cessation
- 1967-07-13 BE BE701328D patent/BE701328A/xx not_active IP Right Cessation
- 1967-07-13 FR FR1559613D patent/FR1559613A/fr not_active Expired
- 1967-07-14 SE SE15294/69A patent/SE354857B/xx unknown
- 1967-07-14 SE SE10550/67A patent/SE322784B/xx unknown
- 1967-07-14 NL NL676709809A patent/NL141512B/xx not_active IP Right Cessation
1968
- 1968-10-15 DK DK496268AA patent/DK117954B/da not_active IP Right Cessation
1973
- 1973-08-10 CY CY69373A patent/CY693A/xx unknown
1980
- 1980-06-11 IT IT8048941A patent/IT8048941A0/it unknown

Also Published As

Publication number	Publication date
NL141512B (nl)	1974-03-15
US3487083A (en)	1969-12-30
DE1720024C3 (de)	1979-12-06
CY693A (en)	1973-08-10
FR1559613A (da)	1969-03-14
NL6709809A (da)	1968-01-15
IL37439A (en)	1972-04-27
SE354857B (da)	1973-03-26
DE1720024B2 (de)	1979-04-19
IT8048941A0 (it)	1980-06-11
BE701328A (da)	1968-01-15
CH485731A (de)	1970-02-15
DE1720024A1 (de)	1972-03-09
SE322784B (da)	1970-04-20
DE1795720A1 (de)	1974-08-29
DK118666B (da)	1970-09-21
GB1200444A (en)	1970-07-29
DK117954B (da)	1970-06-22

Publication	Publication Date	Title
US5124452A (en)	1992-06-23	Process for producing d,1-5-methyltetrahydrofolic acid and its salts
SK281807B6 (sk)	2001-08-06	Spôsob výroby n-[3-(3-kyanopyrazolo[1,5-a]pyrimidin-7-yl)fenyl]- n-etyl-acetamidu
US4767859A (en)	1988-08-30	Process for the preparation of pteridine derivatives
CA3085660A1 (en)	2019-07-18	Method for preparing parp inhibitor and intermediate thereof
CN108997355B (zh)	2020-05-26	一种枸橼酸托法替尼化合物的精制方法
CA1093554A (en)	1981-01-13	Process for producing d,1-5-methyltetrahy-drofolic acid and its salts
CA1103670A (en)	1981-06-23	1,2,4-triazin-5-ones
CN107698592A (zh)	2018-02-16	一种甲氨蝶呤盐的纯化工艺
CN104557938B (zh)	2017-08-29	一类N‑取代吡唑并[3,4‑d]嘧啶酮类化合物及其应用
Richter et al.	1960	Studies in Purine Chemistry. VIII. A Convenient Synthesis of Hypoxanthines and Adenines1, 2
Temple Jr et al.	1965	Cyclization of 6-Hydrazinopurines to s-Triazolo [3, 4-i] purines and Their Rearrangement to the Isomeric s-Triazolo [5, 1-i] purines1
US3487083A (en)	1969-12-30	Preparation of 4-hydroxypyrazolo(3,4-d)pyrimidine
US2407204A (en)	1946-09-03	Triazolo (d) pyrimidines and methods of preparing the same
US3694484A (en)	1972-09-26	Process of preparing 3-amino-2-cyano acrylamide
CN105061428B (zh)	2019-12-27	一种精制他达拉非的方法
MAUTNER	1961	Potential Deoxyribonucleic Acid Cross-linking Agents. 8, 8'-Bispurines1, 2
US2523496A (en)	1950-09-26	Method of preparing xanthine and methylated xanthines
EP1172365B1 (en)	2004-03-17	Process for preparing 2,6-dichloropurine
EP0343597B1 (en)	1993-03-03	Preparation of tris (2-cyanoethyl) amine
US4959475A (en)	1990-09-25	Process for the production of 2,4-diamino-6-piperidinyl-pyrimidine-3-N-oxide
US4985563A (en)	1991-01-15	Process for the preparation of 6-piperidino-2,4-diamino pyrimidine-3-oxide
US2724711A (en)	1955-11-22	Method for the manufacture of 6-mercaptopurine
US4670561A (en)	1987-06-02	Process for obtaining hydrochloric salts of 2, 5, 6-triamino-4 (1h)-pyrimidinone
EP0052959B1 (en)	1986-01-29	Production of purine derivatives and intermediates therefor
US2934535A (en)	1960-04-26	Z-amino-x-trifluoromethylanilino-s