KR850001215A - 5-치환된 [1,2,4]트리아졸로-[1,5-c]피리미딘-2-아민의 제조방법 - Google Patents
5-치환된 [1,2,4]트리아졸로-[1,5-c]피리미딘-2-아민의 제조방법 Download PDFInfo
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- KR850001215A KR850001215A KR1019840004482A KR840004482A KR850001215A KR 850001215 A KR850001215 A KR 850001215A KR 1019840004482 A KR1019840004482 A KR 1019840004482A KR 840004482 A KR840004482 A KR 840004482A KR 850001215 A KR850001215 A KR 850001215A
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- -1 5-substituted [1,2,4] triazolo- [1,5-c] pyrimidin-2-amine Chemical class 0.000 title claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 210000003708 urethra Anatomy 0.000 claims 2
- 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 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- ITQFPVUDTFABDH-UHFFFAOYSA-N ethyl 3-ethoxyprop-2-enoate Chemical compound CCOC=CC(=O)OCC ITQFPVUDTFABDH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy 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
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- 구조식(1)의 치환된 니트릴(A는 -CH=) 또는 피리디닐니트릴(A는 -N=이고 2,3 또는 4 위치에 존재할 수 있다)을 0℃에서 메탄올 및 에테르 혼합용매에 녹이고 염화수소로 포화시키고 12-48시간 동안 0℃에서 보관하여 구조식(2)의 화합물을 얻고; (2)를 0℃에서 무수에탄올에 용해하고 암모니아가스로 포화시키고 0℃에서 48시간동안 보관하여 구조식(3)의 화합물을 얻고; (3)을 알칼리를 포함하는 클로로포름에 용해시킴으로써 유리염기로 전환시키고, 농축시키고, 무수에탄올에 녹여 에틸 3-에톡시-2-프로페노에이트, 에틸포르밀프로피오네이트 나트륨염, 에틸프로피올레이트, 에틸포르밀아세레이트나트륨염 또는 에틸알카노일아세테이트와 수일동안 환류하에 반응시켜 구조식(4)의 화합물을 얻고; (4)를 1-24시간 동안 가온하면서 포스포러스옥시클로라이드와 반응시켜, 얼음위로 쏟고, 분리하여 재결정시켜 구조식(5)의 화합물을 얻고; (5)를 메탄올에 용해시켜서 1-4시간동안 가열하면서 하이드라진하이드레이트와 반응시키고나서, 식혀서 구조식(6)의 중간체를 얻고; (6)을 메탄올에 용해시키고 수시간동안 환류하에 브롬화시아노겐과 반응시켜 본 발명의 생성물을 얻는 것으로 구성된 구조식(I)의 화합물을 제조하는 방법.상기 식에서, R2는 모노- 혹은 디-치환된 페닐[여기서 치환체는 트리플루오로메틸, 니트로, 클로로, 브로모, 요도, 알킬(C1-C6), 포르밀, 1-알키닐, 디플루오로메톡시, 카복스아미도, -CON[알킬(C1-C6)]2, -CON(CH2)n(n은 2-5) 또는 -COO 알킬(C1-C6)],p-메틸페닐설포닐아미노, 2-, 3- 또는 -4-피리디닐, 3-알킬(C1-C6)-4-피리디닐 혹은 4-피리딘-1-옥사이드; R3및 R4는 각기 수소 및 알킬(C1-C6)로 부터 선택된다.상기 식에서, R7은 트리플루오로메틸, 니트로, 클로로, 브로모, 요도, 알킬(C1-C6), -CON[알킬(C1-C6)]2, -CON(CH2)n(n은 2-5), -COO알킬(C1-C6), 포르밀 또는 디플루오로메톡시이다.상기 식에서 R3및 R4는 수소 또는 저급알킬(C1-C6), X는 =0 또는 그의 호변이체; R7은 상술한 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51825083A | 1983-07-28 | 1983-07-28 | |
| US518,250 | 1983-07-28 | ||
| US518250 | 1983-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850001215A true KR850001215A (ko) | 1985-03-16 |
| KR900004000B1 KR900004000B1 (ko) | 1990-06-07 |
Family
ID=24063190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004482A KR900004000B1 (ko) | 1983-07-28 | 1984-07-27 | 5-치환된[1,2,4]트리아졸로-[1,5-c]피리미딘-2-아민 및 그의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0132851B1 (ko) |
| JP (1) | JPS6056983A (ko) |
| KR (1) | KR900004000B1 (ko) |
| AT (1) | ATE46907T1 (ko) |
| AU (1) | AU570989B2 (ko) |
| CA (1) | CA1224785A (ko) |
| DD (1) | DD220780A5 (ko) |
| DE (1) | DE3427823A1 (ko) |
| DK (1) | DK365284A (ko) |
| ES (1) | ES534681A0 (ko) |
| GR (1) | GR82440B (ko) |
| HK (1) | HK4391A (ko) |
| HU (1) | HU190936B (ko) |
| IE (1) | IE57939B1 (ko) |
| IL (1) | IL72529A (ko) |
| NZ (1) | NZ208996A (ko) |
| PL (1) | PL248968A1 (ko) |
| ZA (1) | ZA845842B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102629882B1 (ko) * | 2023-05-10 | 2024-01-29 | 김황래 | 조적수평장치 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0244948A3 (en) * | 1986-04-30 | 1989-03-15 | Schering Agrochemicals Limited | Triazolopyrimidine herbicides |
| CA2284737C (en) | 1997-03-24 | 2007-03-13 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]triazolo[1,5-c]pyrimidine derivatives |
| KR20010087361A (ko) | 1998-09-22 | 2001-09-15 | 히라타 다다시 | [1,2,4]트리아졸로[1,5-ｃ]피리미딘 유도체 |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| TWI462920B (zh) | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| EP2851367B1 (en) * | 2010-05-25 | 2016-10-26 | Dow AgroSciences LLC | Process for the preparation of a 2-amino-5,8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidine by reaction of a 5-halo-8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine with an alkali metal alkoxide in an alcoholic solvent |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3045015A (en) * | 1958-10-03 | 1962-07-17 | Ici Ltd | Triazolo-[2, 3-c]-pyrimidines |
| US3053844A (en) * | 1959-04-13 | 1962-09-11 | Ici Ltd | Mono-acyl derivatives of s-triazolo [2, 3-c] pyrimidines |
| US3046276A (en) * | 1959-06-15 | 1962-07-24 | Ici Ltd | S-triazolo-[2, 3-c] pyrimidine derivatives |
| US4269980A (en) * | 1979-12-17 | 1981-05-26 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-c]pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-c]pyrimidines |
-
1984
- 1984-07-24 NZ NZ208996A patent/NZ208996A/xx unknown
- 1984-07-26 DK DK365284A patent/DK365284A/da not_active Application Discontinuation
- 1984-07-27 DD DD84265730A patent/DD220780A5/de unknown
- 1984-07-27 ZA ZA845842A patent/ZA845842B/xx unknown
- 1984-07-27 AU AU31240/84A patent/AU570989B2/en not_active Ceased
- 1984-07-27 EP EP84108922A patent/EP0132851B1/en not_active Expired
- 1984-07-27 IE IE1943/84A patent/IE57939B1/en not_active IP Right Cessation
- 1984-07-27 KR KR1019840004482A patent/KR900004000B1/ko not_active IP Right Cessation
- 1984-07-27 JP JP59157117A patent/JPS6056983A/ja active Granted
- 1984-07-27 CA CA000459938A patent/CA1224785A/en not_active Expired
- 1984-07-27 ES ES534681A patent/ES534681A0/es active Granted
- 1984-07-27 DE DE19843427823 patent/DE3427823A1/de not_active Ceased
- 1984-07-27 PL PL24896884A patent/PL248968A1/xx unknown
- 1984-07-27 IL IL72529A patent/IL72529A/xx unknown
- 1984-07-27 HU HU842896A patent/HU190936B/hu not_active IP Right Cessation
- 1984-07-27 AT AT84108922T patent/ATE46907T1/de not_active IP Right Cessation
- 1984-07-30 GR GR75446A patent/GR82440B/el unknown
-
1991
- 1991-01-10 HK HK43/91A patent/HK4391A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102629882B1 (ko) * | 2023-05-10 | 2024-01-29 | 김황래 | 조적수평장치 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3427823A1 (de) | 1985-02-07 |
| CA1224785A (en) | 1987-07-28 |
| AU570989B2 (en) | 1988-03-31 |
| IE57939B1 (en) | 1993-05-19 |
| IL72529A (en) | 1988-05-31 |
| HUT34752A (en) | 1985-04-28 |
| ES8505684A1 (es) | 1985-06-16 |
| EP0132851B1 (en) | 1989-10-04 |
| GR82440B (ko) | 1984-12-13 |
| JPS6056983A (ja) | 1985-04-02 |
| AU3124084A (en) | 1985-01-31 |
| DK365284D0 (da) | 1984-07-26 |
| HK4391A (en) | 1991-01-18 |
| EP0132851A1 (en) | 1985-02-13 |
| KR900004000B1 (ko) | 1990-06-07 |
| HU190936B (en) | 1986-12-28 |
| NZ208996A (en) | 1989-08-29 |
| ATE46907T1 (de) | 1989-10-15 |
| ZA845842B (en) | 1985-03-27 |
| PL248968A1 (en) | 1985-10-22 |
| IL72529A0 (en) | 1984-11-30 |
| DD220780A5 (de) | 1985-04-10 |
| ES534681A0 (es) | 1985-06-16 |
| IE841943L (en) | 1985-01-25 |
| JPH0447671B2 (ko) | 1992-08-04 |
| DK365284A (da) | 1985-01-29 |
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