KR840002831A - 피리미딘 유도체의 제조방법 - Google Patents
피리미딘 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840002831A KR840002831A KR1019820005837A KR820005837A KR840002831A KR 840002831 A KR840002831 A KR 840002831A KR 1019820005837 A KR1019820005837 A KR 1019820005837A KR 820005837 A KR820005837 A KR 820005837A KR 840002831 A KR840002831 A KR 840002831A
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- KR
- South Korea
- Prior art keywords
- alkyl
- hydrogen
- methyl
- oxygen
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims 3
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- -1 acyl ester Chemical class 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- KUPUWTXWEZWGMT-UHFFFAOYSA-N 2-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethylamino]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound S1C(CN(C)C)=NC(CSCCNC=2NC(=O)C(CC=3C=NC=CC=3)=CN=2)=C1 KUPUWTXWEZWGMT-UHFFFAOYSA-N 0.000 claims 1
- SWMBFUKVHNGYHG-UHFFFAOYSA-N 2-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethylamino]-5-[(2-methoxypyridin-4-yl)methyl]-1h-pyrimidin-6-one Chemical compound C1=NC(OC)=CC(CC=2C(NC(NCCSCC=3N=C(CN(C)C)SC=3)=NC=2)=O)=C1 SWMBFUKVHNGYHG-UHFFFAOYSA-N 0.000 claims 1
- PMDDSKIROFFBJA-UHFFFAOYSA-N 2-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethylamino]-5-[(6-methoxypyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound C1=NC(OC)=CC=C1CC(C(N1)=O)=CN=C1NCCSCC1=CSC(CN(C)C)=N1 PMDDSKIROFFBJA-UHFFFAOYSA-N 0.000 claims 1
- NXDSUCCXOPIVMN-UHFFFAOYSA-N 2-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethylamino]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound S1C(CN(C)C)=NC(CSCCNC=2NC(=O)C(CC=3C=NC(C)=CC=3)=CN=2)=C1 NXDSUCCXOPIVMN-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 150000002357 guanidines Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 150000007979 thiazole derivatives Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Liquid Crystal Substances (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 일반식(Ⅴ)의 아민을 일반식(Ⅵ)의 피리미딘과 반응시키거나, 일반식(Ⅶ)의 티아졸 유도체를 일반식(Ⅷ)의 화합물과 반응시키거나, 또는 일반식(IX)의 구아니딘 유도체를 일반식(X)의 치환된 아실에스테르와 반응시키고 이어서 임의로 B-부위에 있는 어떤 알콕시 치환체를 가수분해하여 상응하는 하이드록시 치환체를 형성시킴을 특징으로 하여 다음 일반식(XX)의 화합물 또는 약학적으로 무독한 염을 제조하는 방법.상기 식에서, R 및 R3는 독립적으로 수소 또는 (C1내지 C3) 알킬을 나타내며; R1은 수소(C1내지 C3) 알킬, 벤질 또는 벤조일을 나타내고; R2는 수소 또는 (C1내지 C3) 알킬을 나타내며; 또는 R1및 R2는 인접한 질소 원자와 함께 5 내지 7환 원자를 함유하며, 임의로 산소 및 질소로부터 선택된 또다른 하나의 헤테로 원자를 함유하는 포화 헤테로사이클 환을 형성하며; Z는 산소, 황 또는 CH2이고, 단 일반식(Ⅷ)에서는 산소 또는 황이며; X는 황 또는 산소이고; n은 Z가 산소 또는 황이면 2 또는 3이며, Z가 CH2이면, 1,2 또는 3이고; R5는 수소 또는 CH3이며; m은 1,2 또는 3이고; A는 (C1내지 C5) 알킬렌 또는 (CH2)qX(CH2)p[여기에서, q 및 p는 각각 0,1,2 또는 3이며, q와 p의 합은 0 내지 4이다]이며; B는 수소; CH3;(C3내지 C6)-사이클로알킬; 1개 또는 2개의 (C1내지 C3)-알킬, (C1내지 C3)알콕시, 할로, 하이드록시 또는 아미노그룹으로 임의 치환된 헤테로아릴그룹; 나프틸; (1,3-벤조디옥솔릴); 2,3-디하이드로-1,4-벤조디옥시닐; 1개 또는 2개의(C1내지 C3)알킬, (C1내지 C3)알콕시, 할로, OH, 벤질옥시, CF3, (C1내지 C3)알킬-0-(C1내지 C3)알킬렌, 펜옥시 또는 디[(C1내지 C3)알킬]아미노-(C1내지 C3)-알킬렌 그룹으로 임의 치환된 페닐이고; Q는 1급 아민에 의해 친핵성 치환될 수 있는 그룹이며; R6는 (C1내지 C3)알콕시그룹이다.
- 제1항에 있어서, R이 수소 또는 (C1내지 C3)-알킬이며, R1및 R2는 (C1내지 C3)알킬이고, R3는 수소이며, R5는 수소이고, m은 1이며, X는 산소이고, Z는 황이며, n은 2이고, A는 CH2이며, B는 하이드록시, 메톡시 또는 메틸로 임의 치환될 피리딜인 일반식(XX)의 화합물 또는 그의 약학적으로 무독한 염을 제조하는 방법.
- 제1항에있어서, 2-[2-(2-디메틸아미노메틸-4-티아졸릴메틸티오)에틸]아미노-5-(3-피리딜)-메틸-4-피리미돈을 제조하는 방법.
- 제1항에 있어서, 2-[2-(2-디메틸아미노메틸-4-티아졸릴-메틸티오)에틸]아미노-5-(6-메틸-3-피리딜)-메틸-4-피리미돈을 제조하는 방법.
- 제1항에 있어서, 2-[2-(2-디메틸아미노메틸-4-티아졸릴메틸티오)-에틸]아미노-5-(2-메톡시-4-피리딜)-메틸-4-피리미돈을 제조하는 방법.
- 제1항에 있어서, 2-[2-(2-디메틸아미노메틸-4-티아졸릴메틸티오)-에틸]아미노-5-(6-메톡시-3-피리딜)-메틸-4-피리미돈을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33478481A | 1981-12-28 | 1981-12-28 | |
US334,784 | 1981-12-28 | ||
US334784 | 1981-12-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840002831A true KR840002831A (ko) | 1984-07-21 |
KR860000106B1 KR860000106B1 (ko) | 1986-02-19 |
Family
ID=23308823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8205837A KR860000106B1 (ko) | 1981-12-28 | 1982-12-28 | 피리미딘 유도체의 제조방법 |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP0083186B1 (ko) |
JP (1) | JPS58118585A (ko) |
KR (1) | KR860000106B1 (ko) |
AT (1) | ATE34173T1 (ko) |
AU (1) | AU558153B2 (ko) |
CA (1) | CA1206151A (ko) |
CS (1) | CS235976B2 (ko) |
DD (1) | DD203720A5 (ko) |
DE (1) | DE3278473D1 (ko) |
DK (1) | DK574782A (ko) |
ES (1) | ES8403895A1 (ko) |
FI (1) | FI824407L (ko) |
GB (1) | GB2111995B (ko) |
GR (1) | GR78415B (ko) |
HU (1) | HU192951B (ko) |
IE (1) | IE54313B1 (ko) |
IL (1) | IL67496A (ko) |
NZ (1) | NZ202797A (ko) |
PH (1) | PH19797A (ko) |
PL (1) | PL239796A1 (ko) |
PT (1) | PT76004B (ko) |
SU (1) | SU1195906A3 (ko) |
ZA (1) | ZA829247B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4468399A (en) * | 1981-12-28 | 1984-08-28 | Eli Lilly And Company | 2-[2-(2-Aminoalkyl-4-thiazolylmethylthio)alkyl]-amino-5-substituted-4-pyrimidones |
GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
CN102260254A (zh) * | 2010-05-31 | 2011-11-30 | 中国农业科学院植物保护研究所 | 新颖2-硝基亚氨基嘧啶衍生物的合成 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
IN146736B (ko) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
US4200578A (en) * | 1978-12-18 | 1980-04-29 | Bristol-Myers Company | Thiazole derivatives |
US4521418A (en) * | 1979-02-21 | 1985-06-04 | Smith Kline & French Laboratories Limited | Guanidinothiazolyl derivatives |
AU531142B2 (en) * | 1979-04-04 | 1983-08-11 | Smith Kline & French Laboratories Limited | 2 amino- pyimindones |
US4375547A (en) * | 1980-10-02 | 1983-03-01 | Eli Lilly And Company | N-Methyl-N'-2-([(2-dimethylaminomethyl)-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine |
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1982
- 1982-12-14 NZ NZ202797A patent/NZ202797A/en unknown
- 1982-12-14 CA CA000417662A patent/CA1206151A/en not_active Expired
- 1982-12-15 ZA ZA829247A patent/ZA829247B/xx unknown
- 1982-12-15 PH PH28281A patent/PH19797A/en unknown
- 1982-12-15 AU AU91539/82A patent/AU558153B2/en not_active Ceased
- 1982-12-16 IL IL67496A patent/IL67496A/xx unknown
- 1982-12-20 PT PT76004A patent/PT76004B/pt unknown
- 1982-12-20 GB GB08236116A patent/GB2111995B/en not_active Expired
- 1982-12-20 EP EP82306785A patent/EP0083186B1/en not_active Expired
- 1982-12-20 DE DE8282306785T patent/DE3278473D1/de not_active Expired
- 1982-12-20 AT AT82306785T patent/ATE34173T1/de active
- 1982-12-21 IE IE3031/82A patent/IE54313B1/en unknown
- 1982-12-21 FI FI824407A patent/FI824407L/fi not_active Application Discontinuation
- 1982-12-21 CS CS829474A patent/CS235976B2/cs unknown
- 1982-12-23 GR GR70164A patent/GR78415B/el unknown
- 1982-12-24 SU SU823526201A patent/SU1195906A3/ru active
- 1982-12-27 ES ES518592A patent/ES8403895A1/es not_active Expired
- 1982-12-27 HU HU824173A patent/HU192951B/hu not_active IP Right Cessation
- 1982-12-27 DK DK574782A patent/DK574782A/da not_active Application Discontinuation
- 1982-12-28 KR KR8205837A patent/KR860000106B1/ko active
- 1982-12-28 JP JP57234881A patent/JPS58118585A/ja active Pending
- 1982-12-28 DD DD82246677A patent/DD203720A5/de unknown
- 1982-12-28 PL PL23979682A patent/PL239796A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CA1206151A (en) | 1986-06-17 |
DK574782A (da) | 1983-06-29 |
PT76004B (en) | 1985-12-03 |
EP0083186A3 (en) | 1984-05-23 |
JPS58118585A (ja) | 1983-07-14 |
EP0083186B1 (en) | 1988-05-11 |
AU9153982A (en) | 1983-07-07 |
EP0083186A2 (en) | 1983-07-06 |
GB2111995A (en) | 1983-07-13 |
PL239796A1 (en) | 1984-05-21 |
IE54313B1 (en) | 1989-08-16 |
FI824407A0 (fi) | 1982-12-21 |
FI824407L (fi) | 1983-06-29 |
AU558153B2 (en) | 1987-01-22 |
ES518592A0 (es) | 1984-04-01 |
IE823031L (en) | 1983-06-28 |
GB2111995B (en) | 1985-07-24 |
ES8403895A1 (es) | 1984-04-01 |
KR860000106B1 (ko) | 1986-02-19 |
DE3278473D1 (en) | 1988-06-16 |
SU1195906A3 (ru) | 1985-11-30 |
CS235976B2 (en) | 1985-05-15 |
DD203720A5 (de) | 1983-11-02 |
PT76004A (en) | 1983-01-01 |
PH19797A (en) | 1986-07-02 |
ZA829247B (en) | 1984-07-25 |
GR78415B (ko) | 1984-09-27 |
IL67496A (en) | 1986-11-30 |
NZ202797A (en) | 1985-08-30 |
HU192951B (en) | 1987-08-28 |
ATE34173T1 (de) | 1988-05-15 |
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