KR840007727A - (2-옥소-1,2,3,5-테트라히드로이미다조-[2,1-b] 퀴나졸린일) 옥시알킬아미드 제조방법 - Google Patents
(2-옥소-1,2,3,5-테트라히드로이미다조-[2,1-b] 퀴나졸린일) 옥시알킬아미드 제조방법 Download PDFInfo
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- KR840007727A KR840007727A KR1019840000702A KR840000702A KR840007727A KR 840007727 A KR840007727 A KR 840007727A KR 1019840000702 A KR1019840000702 A KR 1019840000702A KR 840000702 A KR840000702 A KR 840000702A KR 840007727 A KR840007727 A KR 840007727A
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- -1 2-oxo-1,2,3,5-tetrahydroimidazo- [2,1-b] quinazolinyl Chemical group 0.000 title claims 7
- 238000002360 preparation method Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 239000012458 free base Substances 0.000 claims 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000013505 freshwater Substances 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- 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
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
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Abstract
내용 없음.
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Claims (3)
- 일반식(A)의 화합물 또는 그 광학 이성체를 할로시아노겐 및 염기와 순차적으로 반응시켜서 R4가 수소인 다음 일반식(I)의 화합물을 생성하고, R4가 수소인 일반식(I)의 화합물을 알킬화시서 R4가 C1-6의 알킬기인 일반식(I)의 대응하는 화합물을 제조하고, A가 아미드(여기서 질소 원자는 C1-6의 히드록시알킬기로 치환시킨다)인 일반식(I)의 화합물을 에스테트화시켜서 A가 히드록시알킬기의 지방족 아실화물 또는 아릴아실화물인 일반식(I)의 대응하는 일반식(I)의 화합물을 제조하고, 일반식(I)의 화합물을 분할시켜 그 광학 이성체를 제조하고, 일반식(I)의 화합물의 유리 염기를 약리학적으로 허용 가능한 그의 산부가염으로 전환시키고, 일반식(I)의 화합물의 약리학적으로 허용가능한 산부가염을 그 유리염기로 전환시키고, 일반식(I)의 화합물의 약리학적으로 허용가능한 산부가염을 다른 염으로 전환시키는 것을 특징으로하는 일반식(1)의 화합물, 그 광학 이성체 및 약리학적으로 허용 가능한 그 산 부가염의 제조방법.위의 일반식(I)의 화합물에서, n는 1-6의 청수이고, R1은 수소 또는 C1-4의 알킬기이고, R2는 수소이거나 R1과 R2가 결합하여 카르보닐기를 생성하고, R3은 수소, C1-6의 알킬기, 페닐기, 벤질기, 히드록시, 저급알킬기 및 그 아실화물, 카르바모일알킬기, 카드복시알킬기, 알콕시카르보닐알킬기 또는 아미노산 측쇄이고, R4는 수소, 벤질기, 히드록시 저급 알킬기 또는 C1-6의 알킬기이고, Y는 수소, C1-4의 알킬기, 할로겐 또는 저급 알콕시기이고, A는 아미드 생성기로서, 이 아미드에서 질소 치환체는 수소 ; C1-6의 알킬기; C1-6의 히드록시알킬기 및 그의 C1-6의 지방족 아실화물 또는 C7-12의 아릴 아실화물 ; C3-8의 시클로알킬기 또는 C4-12의 시클로알킬 저급알킬기(여기서 시클로알킬 링은 치환시크지 않거나 저급알킬기, 저급알콕시기, -OH,OCOR5, 할로겐, -NH2,-N(R5)2, 또는 -COO(R5)기로 치환시킨다)이고, 이 괄호속의 구조식에서 R5는 저급알킬기 ; 페닐기 또는 페닐 저급알킬기이며 이들 페닐기는 치환시키거나 한가지 이상의 저급 알킬기, 할로겐 또는 저급알콕시기 또는-NH2,-N(R5,-COOH 또는-COOR5기로 치환시키되, 이 구조식들에서 R5는 저급알킬기, 모르폴린기, 피페리딘일기, 퍼헥실렌일기, N-저급알킬페라진일기, 피롤리딘일기, 테트라히트로퀴놀린일기, 테트라히드로이소퀴놀린일기, (±)-데카히드로퀴놀린일기 또는 인돌린일기임. 위의 일반식(A)의 화합물에서, Y,R1R2,R3및 A는 위에서 정의한 바와 같고, R6은 C1-6의 알킬기임.
- 다음식(B)의 화합물을 2-메틸티오히탄토인과 반응시키고, 일반식(I)의 화합물의 유리 염기를 그의 약리학적으로 허용가능한 산부가염으로 전환시키고, 일반식(I)의 화합물의 약리학적으로 허용가능한 산부가염을 그의 유리염기로 전환시키고, 일반식(I)의 화합물의 약리학적으로 허용가능한 산부가염을 다른 염으로 전환시키는 것을 특징으로하는 일반식(I)의 화합물 및 약리학적으로 허용가능한 그 산부가염 제조 방법.위의 일반식(I)의 화합물에서, n는 1-6의 정수이고, R1과 R2는 결합하여 카르보닐기를 생성하고 R3은 수소이고, R4는 수소이고, Y는 수소, C1-4의 알킬기, 할로겐 또는 저급 알콕시기이고, A는 아미드 생성기로서, 이 아미드에서 질소치환체는 수소 ; C1-6의 알킬기 ; C1-6의 히드록시알킬기 및 그의 C1-6의 지방족 아실화물 또는 C7-13의 아릴아실화물 ; C3-8의 시클로알킬기 또는 C4-12의 시클로알킬 저급알킬기(여기서 시클로알킬 링은 치환시키지 않거나 저급알킬기, 저급알콕시기, -OH,OCOR5, 할로겐, -NH2,-(R5)2,-NHCOR5,-NHCOR5,-COOH 또는 -COO(R5)기로 치환시킨다)이고, 이 괄호 속의 구조식에서 R5는 저급 알킬기, 페닐기 또는 페닐 저급 알킬기이며 이들 페닐기는 치환시키거나 한가지 이상의 저급알킬기, 할로겐 또는 저급알콕시기 또는-NH2,N(R5)2,-NHCOR5,-COOH 또는-COOR5기로 치환시키되, 이 구조식들에서 R5는 저급알킬기, 모르폴린일기, 피페리딘일기, 퍼헥실렌일기, N-저급알킬피페라진일기, 피롤리딘일기, 테트라히드로퀴놀린일기, 테트라히드로이소퀴놀린일기, (±)-데카히드로퀴놀린일기 또는 인돌린일기임. 위의 일반식(B)의 화합물에서 A,n 및 Y는 앞서 정의한 바와 같음.
- 일반식(C)의 화합물을 아미드 형성제와 반응시키고, 일반식(I)의 화합물의 유리 염기를 그의 약리학 적으로 허용가능한 산부가염으로 전환시키고, 일반식(I)의 화합물의 약리학적으로 허용가능한 산부가염을 그의 유리 염기로 전환시키고 일반식(I)의 화합물의 약리학적으로 허용 가능한 산부가염을 다른 염으로 전환시키는 것을 특징으로하는 일반식(I)의 화합물 및 약리학적으로 허용 가능한 그 산부가염 제조방법.위의 일반식(I)의 화합물에서, 위의 일반식(I)의 화합물에서, n는 1-6의 정수이고, R1은 수소 또는 C1-4의 알킬기이고, R2는 수소이거나 R1과 R2가 결합하여 카르보닐기를 생성하고. R3은 수소, C1-1의 알킬기, 페닐기, 벤질기, 히드록시 저급 알킬 및 그 아실화물, 카르바모일알킬기, 카르복시알킬기, 알콕시카르보닐 알킬기 또는 아미노산 측쇄이고, R4는 수소, 벤질기, 히드록시 저급 알킬기 또는 C1-6의 알킬기이고, Y는 수소, C14의 알킬기, 할로겐 또는 저급 알콕시기이고, A는 아미드 생성기로서, 이 아미드에서 질소치환체는 수소 ; C1-6의 알킬기 ; C1-6의 히드록시알킬기 및 그의 C1-6의 지방족 아실화물 또는 C7-12의 아릴 아실화물 ; C3-8의 시클로알킬기 또는 C4-12의 시클로알킬 저급알킬기(여기서 시클로알킬링은 치환시키지 않거나 저급알킬기, 저급콕시기, -OH,-OCOR5, 할로겐, -NH,N(R5),-COOH 또는-COO(R5) 가로치환시킨다)이고, 이 괄호 속의 구조식에서 R5는 저급알킬기 ; 페닐기 또는 페닐저급 알킬기이며 이들 페닐기는 치환시키거나 한가지 이상의 저급알킬기, 할로겐 또는 저급 알콕시기 또는-NH2,-N(R5)2,-NHCOR5,-COOH 또는-COOR5기로 치환시키되, 이 구조식들에서 이 구조식들에서 R5는 저급알킬기, 모르폴린일기, 피페리딘일기, 퍼헥실렌일기, N-저급 알킬 피페라진일기, 피롤리딘일기, 베트라히드로놀린일기, 베트라히드로이소퀴놀린일기, (±)-데카히드로퀴놀린일기 또는 인돌린일기임. 위의 일반식(C)의 화합물에서, n,R1,R2,R3,R4및 Y는 앞서 정의한 바와 같고 R′는 수소 또는 알킬기임.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| US467125 | 1983-02-16 | ||
| US06/467,125 US4490371A (en) | 1983-02-16 | 1983-02-16 | N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides |
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| US4313947A (en) * | 1974-06-24 | 1982-02-02 | Otsuka Pharmaceutical Co., Ltd. | Platelet aggregation inhibiting 2-oxyindoles, their compositions and method of use |
| NZ187452A (en) * | 1977-06-10 | 1980-05-27 | Otsuka Pharma Co Ltd | N- substituted-aminocarbonylpropoxy-carbostyrils and their preparation |
| NL7807507A (nl) * | 1977-07-25 | 1979-01-29 | Hoffmann La Roche | Tricyclische verbindingen. |
| FR2512674B1 (fr) * | 1981-09-16 | 1986-01-10 | Sandoz Sa | Nouveaux derives tricycliques de la quinazolinone, leur preparation et medicaments contenant ces derives |
| IL74349A (en) * | 1984-02-15 | 1988-07-31 | Syntex Inc | (2-oxo-1,2,3,5-tetrahydroimidazo(2,1-b)quinazolinyl)-oxyalkylamides,their preparation and pharmaceutical compositions containing them |
-
1983
- 1983-02-16 US US06/467,125 patent/US4490371A/en not_active Expired - Fee Related
-
1984
- 1984-02-15 FI FI840603A patent/FI78097C/fi not_active IP Right Cessation
- 1984-02-15 SU SU843706049A patent/SU1349700A3/ru active
- 1984-02-15 CA CA000447497A patent/CA1253862A/en not_active Expired
- 1984-02-15 DE DE8484101551T patent/DE3480925D1/de not_active Expired - Fee Related
- 1984-02-15 NZ NZ207156A patent/NZ207156A/en unknown
- 1984-02-15 AU AU24605/84A patent/AU572118B2/en not_active Ceased
- 1984-02-15 IL IL70964A patent/IL70964A/xx unknown
- 1984-02-15 JP JP59027991A patent/JPS59155383A/ja active Pending
- 1984-02-15 HU HU84593A patent/HU189886B/hu not_active IP Right Cessation
- 1984-02-15 PT PT78106A patent/PT78106B/pt not_active IP Right Cessation
- 1984-02-15 PL PL1984246224A patent/PL143010B1/pl unknown
- 1984-02-15 KR KR1019840000702A patent/KR840007727A/ko not_active Application Discontinuation
- 1984-02-15 EP EP84101551A patent/EP0116948B1/en not_active Expired - Lifetime
- 1984-02-15 PL PL1984253009A patent/PL142959B1/pl unknown
- 1984-02-15 AT AT84101551T patent/ATE49210T1/de not_active IP Right Cessation
- 1984-02-15 PL PL1984253010A patent/PL142960B1/pl unknown
- 1984-02-15 ZA ZA841122A patent/ZA841122B/xx unknown
- 1984-02-15 GR GR73806A patent/GR79543B/el unknown
- 1984-02-15 ES ES529749A patent/ES8604226A1/es not_active Expired
- 1984-02-15 NO NO840551A patent/NO164476C/no unknown
- 1984-02-15 DK DK70784A patent/DK70784A/da not_active Application Discontinuation
-
1985
- 1985-06-14 ES ES544203A patent/ES8603879A1/es not_active Expired
- 1985-06-14 ES ES544202A patent/ES8603878A1/es not_active Expired
-
1986
- 1986-10-08 SU SU864028265A patent/SU1493109A3/ru active
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