GB1116388A - Cycloaliphatic pyrimidines and process for their manufacture - Google Patents
Cycloaliphatic pyrimidines and process for their manufactureInfo
- Publication number
- GB1116388A GB1116388A GB44046/66A GB4404666A GB1116388A GB 1116388 A GB1116388 A GB 1116388A GB 44046/66 A GB44046/66 A GB 44046/66A GB 4404666 A GB4404666 A GB 4404666A GB 1116388 A GB1116388 A GB 1116388A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- amino
- hydroxymethyl
- pyrimidine
- prepared
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Novel quaternary 5-ammonium-methyl-4-amino-2-R-pyrimidine salts, in which R represents a cycloaliphatic group and the ammonium nitrogen atom is part of a monocyclic or bicyclic heterocyclic radical containing one or more double bonds, one of which extends from the ammonium nitrogen atom, are prepared by reacting a reactive ester or ether of a 4-amino-5-hydroxymethyl - 2 - R - pyrimidine with a monocyclic or bicyclic heterocyclic compound containing at least one ring nitrogen atom and one or more double bonds, one of which extends from the ring nitrogen atom. 4 - Amino - 5 - hydroxymethyl - 2 - R - pyrimidines are prepared by reacting an R-halide with sodium cyanide to form the corresponding R-cyanide, reacting this an alkanol to form the corresponding alkyl R-carboximidate, reacting this with ammonia to form the corresponding R-carboxylic acid amidine, reacting this with a C1- 7 alkoxymethylene-malonitrile to form a 4-amino - 5 - cyano - 2 - R - pyrimidine, hydrogenating this to the corresponding 5-aminomethyl compound and converting this into the corresponding 5-hydroxymethyl compound by treatment with nitrous acid. Alternatively, the 5-cyano compound may be hydrogenated in the presence of hydrochloric acid to form the 5-hydroxymethyl compound directly. Cyclobutylmethyl bromide is prepared by treating cyclobutane carboxylic acid with lithium aluminium hydride to form cyclobutylmethanol and treating this with phosphorus tribromide. Cyclopropylmethyl bromide is similarly prepared via cyclopropylmethanol. 4 - Amino - 5 - chloromethyl - 2 - cyclopropylmethyl-pyrimidine hydrochloride is prepared by reacting 4-amino-5-hydroxymethyl-2-cyclopropylmethyl-pyrimidine with thionyl chloride.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49323365A | 1965-10-05 | 1965-10-05 | |
| US53466666A | 1966-03-16 | 1966-03-16 | |
| US57267166A | 1966-08-16 | 1966-08-16 | |
| US592314A US3385857A (en) | 1965-10-05 | 1966-11-07 | Cycloaliphatic pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1116388A true GB1116388A (en) | 1968-06-06 |
Family
ID=27504357
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44047/66A Expired GB1116389A (en) | 1965-10-05 | 1966-10-03 | Compositions for treatment of coccidiosis |
| GB44046/66A Expired GB1116388A (en) | 1965-10-05 | 1966-10-03 | Cycloaliphatic pyrimidines and process for their manufacture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB44047/66A Expired GB1116389A (en) | 1965-10-05 | 1966-10-03 | Compositions for treatment of coccidiosis |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3385857A (en) |
| AT (2) | AT281040B (en) |
| BE (2) | BE687779A (en) |
| BR (2) | BR6683425D0 (en) |
| CH (1) | CH484168A (en) |
| DE (1) | DE1670389A1 (en) |
| DK (1) | DK122326B (en) |
| FI (1) | FI45115C (en) |
| FR (1) | FR1503663A (en) |
| GB (2) | GB1116389A (en) |
| IL (1) | IL26554A (en) |
| NL (2) | NL6613987A (en) |
| NO (1) | NO122650B (en) |
| SE (1) | SE331786B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454575A (en) * | 1967-03-06 | 1969-07-08 | Ciba Geigy Corp | Quaternary 5-ammonium-methyl-4-amino-2 cycloaliphatylpyrimidine salts |
| BE795071A (en) * | 1972-02-08 | 1973-08-07 | Merck & Co Inc | COCCIDIOSTATIC COMPOUNDS |
| US4006143A (en) * | 1974-04-09 | 1977-02-01 | Merck & Co., Inc. | Heterocyclic substituted pyrimidine compounds |
| US4044133A (en) * | 1974-04-18 | 1977-08-23 | Merck & Co., Inc. | Anticoccidial compositions |
| US6077981A (en) * | 1998-08-28 | 2000-06-20 | Eastman Chemical Company | Process for the production of cyclopropylmethyl halides |
| US6118032A (en) * | 1999-08-03 | 2000-09-12 | Eastman Chemical Company | Process for the production of cyclopropylmethyl halides |
| EP1234508A1 (en) * | 2001-02-21 | 2002-08-28 | Universiteit Gent | Antiprotozoal methods, compositions and feedstuffs |
| CN111760032B (en) * | 2020-07-22 | 2022-02-25 | 广州白云山宝神动物保健品有限公司 | Composition for preventing and treating drug-resistant coccidiosis of chicken and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042676A (en) * | 1960-02-02 | 1962-07-03 | Merck & Co Inc | Pyridinium quaternary salts and methods of preparing the same |
-
1966
- 1966-09-21 IL IL26554A patent/IL26554A/en unknown
- 1966-09-27 CH CH1392966A patent/CH484168A/en not_active IP Right Cessation
- 1966-10-01 DE DE19661670389 patent/DE1670389A1/en active Pending
- 1966-10-03 FI FI662586A patent/FI45115C/en active
- 1966-10-03 GB GB44047/66A patent/GB1116389A/en not_active Expired
- 1966-10-03 GB GB44046/66A patent/GB1116388A/en not_active Expired
- 1966-10-04 NL NL6613987A patent/NL6613987A/xx unknown
- 1966-10-04 AT AT994368A patent/AT281040B/en not_active IP Right Cessation
- 1966-10-04 NL NL6613986A patent/NL6613986A/xx unknown
- 1966-10-04 FR FR78651A patent/FR1503663A/en not_active Expired
- 1966-10-04 NO NO164999A patent/NO122650B/no unknown
- 1966-10-04 DK DK511466AA patent/DK122326B/en unknown
- 1966-10-04 BE BE687779A patent/BE687779A/xx unknown
- 1966-10-04 AT AT929366A patent/AT277653B/en not_active IP Right Cessation
- 1966-10-04 BE BE687778A patent/BE687778A/xx unknown
- 1966-10-04 SE SE13371/66A patent/SE331786B/xx unknown
- 1966-10-05 BR BR183425/66A patent/BR6683425D0/en unknown
- 1966-10-05 BR BR183424/66A patent/BR6683424D0/en unknown
- 1966-11-07 US US592314A patent/US3385857A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI45115B (en) | 1971-11-30 |
| US3385857A (en) | 1968-05-28 |
| FR1503663A (en) | 1967-12-01 |
| DK122326B (en) | 1972-02-21 |
| FI45115C (en) | 1972-03-10 |
| GB1116389A (en) | 1968-06-06 |
| CH484168A (en) | 1970-01-15 |
| BE687779A (en) | 1967-04-04 |
| AT277653B (en) | 1970-01-12 |
| BE687778A (en) | 1967-04-04 |
| BR6683425D0 (en) | 1973-12-04 |
| AT281040B (en) | 1970-05-11 |
| IL26554A (en) | 1971-04-28 |
| NL6613987A (en) | 1967-04-06 |
| DE1670389A1 (en) | 1970-11-05 |
| BR6683424D0 (en) | 1973-12-04 |
| NL6613986A (en) | 1967-04-06 |
| NO122650B (en) | 1971-07-26 |
| SE331786B (en) | 1971-01-11 |
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