KR830007624A - 헤테로 사이클릭 화합물의 제조방법 - Google Patents
헤테로 사이클릭 화합물의 제조방법 Download PDFInfo
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- KR830007624A KR830007624A KR1019810004398A KR810004398A KR830007624A KR 830007624 A KR830007624 A KR 830007624A KR 1019810004398 A KR1019810004398 A KR 1019810004398A KR 810004398 A KR810004398 A KR 810004398A KR 830007624 A KR830007624 A KR 830007624A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims 8
- 238000000034 method Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 239000011593 sulfur Chemical group 0.000 claims 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- -1 cyano, nitro, amino Chemical group 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 claims 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- CHPODLGGUNEVME-UHFFFAOYSA-N 3-(3-oxo-4,5-dihydro-2h-1,2,4-triazin-6-yl)benzonitrile Chemical compound N1C(=O)NCC(C=2C=C(C=CC=2)C#N)=N1 CHPODLGGUNEVME-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- DYZWXBMTHNHXML-UHFFFAOYSA-N N-propylbenzamide Chemical compound CCCNC(=O)C1=CC=CC=C1 DYZWXBMTHNHXML-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002371 cardiac agent Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000001351 cycling effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 claims 1
- SDIDYFBTIZOPLA-UHFFFAOYSA-N n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1 SDIDYFBTIZOPLA-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 claims 1
- 239000003071 vasodilator agent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 다음 구조식의 헤테로사이클릭 화합물 또는 이들의 염상기 구조식에서X는 -CR1R2- 이고 Y는 산소, 황 또는 -NR3-상기에서 R1, R2와 R3는 같거나 또는 다른 것이며 각기 수소 또는 탄소원자 4이상의 알킬;또는 X는 산소, 황 또는 -NH-이고 Y는 -CH2-;R4와 R5는 같거나 또는 다른 것이며, 각기 수소, 시아노, 니트로, 아미노 또는 하이드록시, 또는 탄소원자 4 이상의 알킬티오 또는 다음 구조식을 갖는 것이며,-Q-CZ-OR6-Q-SO2-NR7R8-Q-CZ-NR7R8-Q-SO2-R9-Q-CZ-R9-Q-SO-R9상기 식에서 Q는 직접 연결된 것이거나 또는 이미노(-NH-) 또는 탄소원자 4이상의 옥시알킬렌, 상기에서 Z는 산소 또는 황이고 R6,R7,R8과 R9은 같거나 또는 다른 것이며 각기 수소, 알킬, 알켄일, 사이클로알킬 또는 탄소원자 6 이상의 알콜시알킬 또는 아릴 또는 탄소원자 12 이상의 아릴알킬, 또는 R7과 R8은 함께 질소에 인접하여 5- 또는 6- 각 전체 포화된 헤테로사이클링, R4와 R5는 둘다 수소; 또는 R4와 R5는 함께 벤젠링 A와 연결되어 벤즈헤테로 사이클릭링을 형성하며 상기에서 헤테로 사이클릭 부분은 산소황 또는 질소원자를 포함하는 5 또는 6- 각 링이고 헤테로 사이클릭 부분은 각기 탄소원자 6 이상의 옥소치환체 또는 알킬 또는 알카노일치환체를 임의로 포함할 수 있으며;벤젠링 A는 임의로 하나 또는 다수 치환체를 갖는다.
- X가 -CH2-이고 Y는 -NH- 또는 X는 -CH2, -CHCH3- 또는 -C(CH3)2이고 Y는 황; 또는 X는 산소 또는 황이고 Y는 -CH2-;R4는 구조식 -COOR6또는 -CONR7R8을 갖고 상기에서 R6, R7과 R8은 청구범위 1에서 언급한 것이며 R5는 수소이고 링 A는 다른 치환체를 갖지 않는 것인 청구범위 1에서 청구된 헤테로사이클릭 화합물 또는 R6가 수소일때 이들의 염기부가염.
- X가 -CH2-이고 Y는 -NH-, 또는 X가 황이고 Y는 -CH2- 인 청구범위 2에서 청구된 헤테로 사이클릭 화합물.
- X가 -CH2-, -CHCH3또는 -C(CH3)2이고 Y는 황, 또는 X가 -CH2이고 Y가 산소, -NH 또는 -NCH3-, 또는 X가 산소, 황 또는 -NH-이고 Y는 -CH2-, R4는 수소, R5는 시아노이고 링 A는 다른 치환체를 갖지 않는 것인 청구범위 1에서 청구된 헤테로사이클릭 화합물.
- 화합물 P-(5,6-디하이드로-5-옥소-4H-1,3,4-티아디아진-2-일) 벤조익산 또는 메틸 또는 이들의 이소프로필에스테르;P-(5,6-디하이드로-5-옥소-4H-1,3,4-티아디아진-2-일) 벤즈아마이드 또는 N-메틸벤즈아마이드;P-(5,6-디하이드로-5-옥소-4H-1,3,4-옥사디아진-2-일) 벤즈아마이드;6-m-시아노페닐-4,5-디하이드로-1,2,4-트리아진-3(2H)-온;P-(2,3,4,5-테트라하이드로-3-옥소-1,2,4-트리아진-6-일)벤즈아마이드, N-메틸벤즈아마이드, N-에틸벤즈아마이드, 또는 N-프로필벤즈아마이드;3-P-시아노페닐-3,4,5-디하이드로-1,2,4-트리아진-6(1H)-온;P-(2,3-디하이드로-2-옥소-6H-1,3,4-티아디아진-5-일)벤즈아마이드 또는 N, N-디메틸벤즈아마이드;또는 이소프로필 P-(2,3-디하이드로-2-옥소-6H-1,3,4-티아디아진-5-일)벤즈에이트
- 화합물 N,N-디메틸-P-(5,6,-디하이드로-5-옥소-4H-1,3,4-티아디아진-2-일)벤즈아마이드
- (a) 다음 구조식의 하이드라지드 또는 티오하이드라지드를 구조식 Hal-CH2-COOH의 산 또는 이들의 반응성 유도체와 반응시켜 X는 산소 또는 황이고 Y가 -CH2-인 화합물 제조와상기식에서R4, R5와 A는 청구범위 1내지 4의 어느 하나에서 언급된 것이고,X는 황 또는 산소(b) 다음 구조식의 펜아실 할라이드를 구조식 H2N, NH, CS-O-R10또는 H2N-NH-CSO-M+의 티오카르바제이트와 반응시켜 X가 -CR1R2-이고 Y가 황인 화합물 제조와상기 구조식에서R1, R2, R4, R5와 A는 청구범위 1내지 4에서 언급한 것이고Hal은 상기 언급한 것이며R10은 탄소원자 4 이상의 알킬이고M+는 알카리금속 또는 암모늄이온; 또는(c) 다음 구조식의 화합물을 환화시켜 X가 -CR1R2-이고 Y가 산소인 화합물의 제조와상기 구조식에서A, R1, R2, R4와 R5는 청구범위 1 내지 4의 어느 하나에서 언급한 것이고R10은 상기 언급한 것이거나 또는(d) 다음 구조식의 화합물을 하이드라진과 반응시켜 X가 -NH-이고 Y가 -CH2-인 본 발명 화합물 제조와상기 식에서A, R4와 R5는 청구범위 1 내지 4의 어느 하나에서 언급한 것이고R10은 상기 언급한 것이다(두 R10치환체는 탄소원자 4이상의 같거나 또는 다른 알킬기)(e) 다음 구조식 화합물을 하이드라진과 반응시켜 X가 -CR1R2-이고 Y가 -NH-인 화합물 제조와상기 구조식에서A는 A, R1, R2, R4와 R5는 청구범위 1 내지 4에서 언급한 것이고, R10은 상기 언급한 바와 같다.그후 R4또는 R5가 니트로치환체인 상응하는 화합물을 환언시키거나 또는 Q가 아미노인 상응하는 화합물을 가수분해시켜 얻을 수 있는 R4또는 R5가 아미노치환인 화합물; 또는R4또는 R5가 알콕시카르보닐 또는 아미노카르보닐 치환체인 상응하는 화합물을 가수분해시켜 얻어질 수 있는 R4또는 R5가 카르복시 치환체인 화합물; 또는가수분해, 또는 R4또는 R5가 시아노치환체인 상응하는 화합물을 황화수소와 반응시키거나 또는 가수분해에 의해 얻어질 수 있는 R4또는 R5가 카르복시, 카르바모일 또는 티오카보닐 치환체인 화합물; 또는상응하는 아미노-치환된 화합물을 이소시안에이트와 반응시키거나 또는 아실화에 의해 얻어질 수 있는 R4또는 R5가 Q-포함치환체(여기서 Q는 아미노)인 화합물; 또는R4또는 R5가 카르복시인 상응하는 화합물 또는 이들의 활성화된 유도체를 구조식 R6OH의 알콜 또는 구조식 NHR7R8의 아민과 반응시켜 얻어질 수 있는 R4또는 R5가 구조식 -Q-CZ-OR6또는 -Q-CZ-NR7R8(여기서 Q는 직접 연결된 것이고 Z는 산소)인 화합물; 또는R4또는 R5가 하이드록시인 상응하는 화합물을 구조식 Hal-alk-CZ-OR6(여기서 Hal은 할로겐 원자이고 -alk-는 탄소원자 4이상의 알킬렌그룹)와 반응시키며 임의로 구조식 NHR7R8의 아민과 반응시켜 -CZ-OR6그룹을 -CZ-NR7R8의 전환에 의해 얻어질 수 있는 R4또는 R5가 구조식 -Q-CZ-OR6또는 Q-CZ-NR7R8(여기서 Q는 옥시알킬렌)을 갖는 화합물; 또는R3가 수소인 상응하는 화합물의 알킬화에 의해 얻어질 수 있는 R3가 알킬인 화합물로 구성되는 청구범위 1내지 6의 어느 하나에서 청구된 헤테로 사이클릭 화합물의 제조방법.
- 활성성분으로 청구범위 1 내지 6의 어느 하나에서 청구된 적어도 하나 헤테로 사이클릭 화합물을 약학적으로 받아들여질 수 있는 희석제 또는 담체와 혼합하여 구성되는 약학적 조성물.
- 헤테로사이클릭 화합물에 진성제, 혈관확장제, 이뇨제, 심장막안정제, 파키슨질병과 다른 진전의 치료에 사용된 제제와 강심제로부터 선택된 하나 또는 다수 약품을 첨가하여 만들어진 청구범위 8에서 청구된 조성물.
- 청구범위 1 내지 6의 어느 하나에서 청구된 헤테로사이클릭 화합물의 효과적인 양을 온형동물에 투여하여 온혈동물의 만성 또는 급성 심장질환을 치료하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8036680 | 1980-11-14 | ||
| GB8036680 | 1980-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007624A true KR830007624A (ko) | 1983-11-04 |
Family
ID=10517317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004398A KR830007624A (ko) | 1980-11-14 | 1981-11-14 | 헤테로 사이클릭 화합물의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US4423045A (ko) |
| EP (1) | EP0052442B1 (ko) |
| JP (3) | JPS57109771A (ko) |
| KR (1) | KR830007624A (ko) |
| AU (1) | AU7709181A (ko) |
| CA (1) | CA1176250A (ko) |
| DD (1) | DD202020A5 (ko) |
| DE (1) | DE3172252D1 (ko) |
| DK (1) | DK498881A (ko) |
| ES (2) | ES507126A0 (ko) |
| FI (1) | FI813566L (ko) |
| GR (1) | GR79554B (ko) |
| HU (1) | HU185979B (ko) |
| MW (1) | MW4881A1 (ko) |
| NO (1) | NO813850L (ko) |
| NZ (1) | NZ198967A (ko) |
| PL (2) | PL233809A1 (ko) |
| PT (1) | PT73995B (ko) |
| ZA (1) | ZA817597B (ko) |
| ZW (1) | ZW26381A1 (ko) |
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| US4616014A (en) * | 1981-10-22 | 1986-10-07 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
| CA1199027A (en) * | 1981-11-12 | 1986-01-07 | Stuart D. Mills | Heterocyclic derivatives of pyridazinone, thiadiazinone, oxadiazinone and triazinone |
| US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
| US4657906A (en) * | 1982-06-05 | 1987-04-14 | Smith Kline & French Laboratories Ltd. | Heterocyclic compounds having inotropic activity |
| JPS5962578A (ja) * | 1982-10-04 | 1984-04-10 | Mitsui Toatsu Chem Inc | オキサジアジン誘導体およびそれを含有する医薬組成物 |
| US4581356A (en) * | 1983-03-22 | 1986-04-08 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| GB8310435D0 (en) * | 1983-04-18 | 1983-05-25 | Fujisawa Pharmaceutical Co | Triazine derivatives |
| JPS59196874A (ja) * | 1983-04-22 | 1984-11-08 | Fujisawa Pharmaceut Co Ltd | トリアジン誘導体 |
| GB8328907D0 (en) * | 1983-10-28 | 1983-11-30 | Smith Kline French Lab | Chemical compounds |
| GB8329784D0 (en) * | 1983-11-08 | 1983-12-14 | Smith Kline French Lab | Heterocyclic compounds |
| GB8332313D0 (en) * | 1983-12-02 | 1984-01-11 | Smith Kline French Lab | Chemical compounds |
| US4508718A (en) * | 1984-01-16 | 1985-04-02 | Warner-Lambert Company | Cardiotonic and antihypertensive oxadiazinone compounds |
| DE3581641D1 (de) | 1984-10-04 | 1991-03-07 | Zenyaku Kogyo Kk | 1,4-thiazinabkoemmlinge, deren herstellung und diese enthaltende kardiotonische mittel. |
| JPS61106574A (ja) * | 1984-10-29 | 1986-05-24 | Yoshitomi Pharmaceut Ind Ltd | オキサ（またはチア）ジアジン誘導体 |
| DE3531658A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
| FR2592878B1 (fr) * | 1986-01-16 | 1988-12-16 | Pf Medicament | Monoaryl-5 as triazinones-3 substituees en position 2, leur procede de preparation et leur application en tant que medicaments |
| US4898862A (en) * | 1986-03-20 | 1990-02-06 | Sankyo Company Limited | 1,2,4-triazinone derivatives, their preparation and use |
| US4861773A (en) * | 1986-04-28 | 1989-08-29 | Smith Kline & French Laboratories Limited | Heterocyclic compounds |
| GB8610369D0 (en) * | 1986-04-28 | 1986-06-04 | Smith Kline French Lab | Heterocyclic compounds |
| DE3706427A1 (de) * | 1987-02-27 | 1988-09-08 | Boehringer Mannheim Gmbh | Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel |
| AU614965B2 (en) * | 1987-06-06 | 1991-09-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Thiadiazinones |
| GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| US5185332A (en) * | 1989-02-11 | 1993-02-09 | Orion-Yhtyma Oy | Thiadiazines and pharmaceutical compositions thereof as well as method of use |
| DE3913597A1 (de) * | 1989-04-25 | 1990-11-08 | Heumann Pharma Gmbh & Co | Diazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4239540A1 (de) * | 1992-11-25 | 1994-05-26 | Asta Medica Ag | Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung |
| TW309520B (ko) * | 1994-04-26 | 1997-07-01 | Mitsubishi Chem Corp | |
| MX9605270A (es) * | 1994-05-04 | 1997-10-31 | Bayer Ag | Amidas de acidos tiocarboxilicos aromaticas substituidas. |
| USRE39263E1 (en) * | 1994-05-04 | 2006-09-05 | Bayer Aktiengesellschaft | Substituted aromatic thiocarboxylic acid amides and their use as herbicides |
| WO1998037068A1 (en) | 1997-02-21 | 1998-08-27 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| DE19929781A1 (de) * | 1999-06-29 | 2001-01-04 | Bayer Ag | N-[4-(6-Oxotetrahydrotriazinyl)phenyl]amide und ihre Verwendung |
| RU2008123384A (ru) | 2005-11-16 | 2009-12-27 | Новартис АГ (CH) | БИОМАРКЕРЫ ДЛЯ ЛЕЧЕНИЯ АНТИТЕЛОМ к Nogo-A ПРИ ПОВРЕЖДЕНИЯХ СПИННОГО МОЗГА |
| EP2530073A4 (en) | 2010-01-27 | 2014-10-08 | Mitsubishi Rayon Co | NEW CHAIN TRANSFER AND EMULSION POLYMERIZATION THEREWITH |
| JOP20200024A1 (ar) | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
| EP3661917B1 (en) | 2017-08-04 | 2022-05-11 | Bayer Aktiengesellschaft | 6-((3-trifluoromethyl)phenyl)-4,5-dihydropyridazin-3(2h)-one derivatives as pde3a and pde3b inhibitors for treating cancer |
| CA3128293A1 (en) | 2019-02-01 | 2020-08-06 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2h)-one compounds for the treatment of hyperproliferative diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314455A (en) * | 1964-07-24 | 1967-04-18 | Black Clawson Co | Band saw resawing machine |
| US3377345A (en) * | 1966-09-23 | 1968-04-09 | Dow Chemical Co | Substituted 3, 4, 5, 6-tetrahydro-2h-1, 3, 4-oxadiazin-2-one compounds and method ofpreparation thereof |
| FR8169M (ko) * | 1967-05-17 | 1970-08-31 | ||
| US3946010A (en) * | 1975-04-09 | 1976-03-23 | E. R. Squibb & Sons, Inc. | 3-Phenyl-2,5-dihydro-as-triazin-6 (1H)-ones |
| US4097425A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Thermoplastic formable blends, a foaming method and products made thereby |
| US4097671A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Dihydrooxadiazinones and method for making |
| US4105848A (en) * | 1976-12-27 | 1978-08-08 | General Electric Company | Process for the production of dihydrooxadiazinone compounds |
| ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
| US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
| JPH072947B2 (ja) * | 1985-06-27 | 1995-01-18 | 松下電子工業株式会社 | 螢光体 |
-
1981
- 1981-10-23 DE DE8181305020T patent/DE3172252D1/de not_active Expired
- 1981-10-23 EP EP81305020A patent/EP0052442B1/en not_active Expired
- 1981-11-02 ZW ZW263/81A patent/ZW26381A1/xx unknown
- 1981-11-03 ZA ZA817597A patent/ZA817597B/xx unknown
- 1981-11-04 MW MW48/81A patent/MW4881A1/xx unknown
- 1981-11-04 AU AU77091/81A patent/AU7709181A/en not_active Abandoned
- 1981-11-11 DK DK498881A patent/DK498881A/da not_active Application Discontinuation
- 1981-11-11 FI FI813566A patent/FI813566L/fi not_active Application Discontinuation
- 1981-11-11 GR GR66494A patent/GR79554B/el unknown
- 1981-11-11 HU HU813367A patent/HU185979B/hu unknown
- 1981-11-13 ES ES507126A patent/ES507126A0/es active Granted
- 1981-11-13 NZ NZ198967A patent/NZ198967A/en unknown
- 1981-11-13 JP JP56181250A patent/JPS57109771A/ja active Pending
- 1981-11-13 CA CA000390035A patent/CA1176250A/en not_active Expired
- 1981-11-13 NO NO813850A patent/NO813850L/no unknown
- 1981-11-13 PL PL23380981A patent/PL233809A1/xx unknown
- 1981-11-13 PL PL23880281A patent/PL238802A1/xx unknown
- 1981-11-13 PT PT73995A patent/PT73995B/pt unknown
- 1981-11-14 KR KR1019810004398A patent/KR830007624A/ko unknown
- 1981-11-16 DD DD81234877A patent/DD202020A5/de unknown
- 1981-11-16 US US06/321,899 patent/US4423045A/en not_active Expired - Lifetime
-
1982
- 1982-10-16 ES ES516588A patent/ES516588A0/es active Granted
-
1983
- 1983-08-31 US US06/528,103 patent/US4503054A/en not_active Expired - Fee Related
-
1984
- 1984-11-28 US US06/675,741 patent/US4587246A/en not_active Expired - Lifetime
-
1986
- 1986-04-24 JP JP61093476A patent/JPS6230771A/ja active Pending
- 1986-04-24 JP JP61093477A patent/JPS6236370A/ja active Granted
- 1986-05-01 US US06/858,126 patent/US4683232A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0572384B2 (ko) | 1993-10-12 |
| PL233809A1 (en) | 1983-09-12 |
| PT73995A (en) | 1981-12-01 |
| ZW26381A1 (en) | 1983-06-01 |
| ES8307231A1 (es) | 1983-07-01 |
| US4423045A (en) | 1983-12-27 |
| EP0052442A1 (en) | 1982-05-26 |
| GR79554B (ko) | 1984-10-30 |
| CA1176250A (en) | 1984-10-16 |
| PT73995B (en) | 1983-06-20 |
| HU185979B (en) | 1985-04-28 |
| ZA817597B (en) | 1982-10-27 |
| DD202020A5 (de) | 1983-08-24 |
| ES8401044A1 (es) | 1983-11-16 |
| ES507126A0 (es) | 1983-07-01 |
| EP0052442B1 (en) | 1985-09-11 |
| PL238802A1 (en) | 1983-09-12 |
| NZ198967A (en) | 1984-12-14 |
| US4587246A (en) | 1986-05-06 |
| JPS57109771A (en) | 1982-07-08 |
| FI813566L (fi) | 1982-05-15 |
| DK498881A (da) | 1982-05-15 |
| US4683232A (en) | 1987-07-28 |
| NO813850L (no) | 1982-05-18 |
| ES516588A0 (es) | 1983-11-16 |
| JPS6230771A (ja) | 1987-02-09 |
| DE3172252D1 (en) | 1985-10-17 |
| JPS6236370A (ja) | 1987-02-17 |
| MW4881A1 (en) | 1983-09-14 |
| US4503054A (en) | 1985-03-05 |
| AU7709181A (en) | 1982-05-20 |
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