KR850002483A - 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일]피페라진 유도체의 제조방법 - Google Patents
1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일]피페라진 유도체의 제조방법 Download PDFInfo
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- KR850002483A KR850002483A KR1019840005558A KR840005558A KR850002483A KR 850002483 A KR850002483 A KR 850002483A KR 1019840005558 A KR1019840005558 A KR 1019840005558A KR 840005558 A KR840005558 A KR 840005558A KR 850002483 A KR850002483 A KR 850002483A
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- 238000000034 method Methods 0.000 title claims 6
- 150000004885 piperazines Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 13
- 239000002253 acid Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- -1 pyrrolidindione-1-yl Chemical group 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 1
- MWYWEZQRISXVNW-UHFFFAOYSA-N 1-[4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl]-3,3-diphenylpyrrolidine-2,5-dione Chemical compound O=C1N(CCCCN2CCN(CC2)C=2C3=CC=CC=C3SN=2)C(=O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWYWEZQRISXVNW-UHFFFAOYSA-N 0.000 claims 1
- IFVHVXAOZIGOLZ-UHFFFAOYSA-N 3,3-diphenyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrrolidine-2,5-dione Chemical compound O=C1CC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 IFVHVXAOZIGOLZ-UHFFFAOYSA-N 0.000 claims 1
- ZFSXTHDCRMCHDS-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-methyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrrolidine-2,5-dione Chemical compound O=C1C(C)(C=2C=CC(F)=CC=2)CC(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 ZFSXTHDCRMCHDS-UHFFFAOYSA-N 0.000 claims 1
- QWQKPQZUFPYAOJ-UHFFFAOYSA-N 3-methyl-3-phenyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]pyrrolidine-2,5-dione Chemical compound O=C1C(C)(C=2C=CC=CC=2)CC(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 QWQKPQZUFPYAOJ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000623 heterocyclic group Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000005490 tosylate group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
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- 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
- C07D401/14—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 three or more hetero rings
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- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
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Abstract
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본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- (a) 적절한 반응 조건하에 다음 구조식 (Ⅱ)의 화합물을 다음 구조식 (Ⅲ)의 화합물과 반응시켜 다음 구조식 (Ⅰ)의 화합물을 얻은 다음, 이어서 (b) 구조식 (Ⅰ) 화합물의 염이 필요한 경우에는 임의로 구조식 (Ⅰ)의 화합물을 제약상 허용되는 산과 혼합처리하여 구조식(Ⅰ)의 화합물의 염을 생성시키는 것을 특징으로 하는 구조식(Ⅰ)의 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일)알킬]피페라진 유도체 또는 제약상 허용되는 그의 산부가염의 제조방법.위 각 식에서, R1은 C1-C4알킬, 트리플루오로메틸, Z-치환 페닐(Z는 수소 또는 할로겐)이거나, 또는 R1은 R2와 결합하여 용융된 Z-치환 페닐계[Z는 수소 또는 할로겐(R1에 대하여)]가 결합된 C4-5브리지를 형성하거나, 또는 R1은 R3과 결합하여 용융된 시클로 헥세닐환 또는 X1-X4테트라-치환 페닐환(X1-X4는 각각 수소, 할로겐 또는 니트로 중에서 선정됨)을 형성하는 것이고, R2는 C1-4알킬, Z-치환 페닐(Z는 위에서 정의한 바와 같음)이거나, 또는 R1과 R4이 용융 페일환을 형성할 때에는 존재하지 않으며, 또는 R1과 결합하여 위에서 정의한 바와 같은 알킬렌 브리지를 형성하는 것이며, R4은 수소이거나 R1과 결합하여 위에서 정의한 바와 같이 용융 페닐환을 형성하는 것이고, B는 벤즈이소티아졸, 피리딘 및 피리미딘으로 구성된 군 중에서 선정된 R4,R5-디치환 헤테로환(R4및 R5는 각각 C1-4알킬, C1-5알콕시, C1-4알킬티오, 시아노, 할로겐 또는 수소중에서 선택됨)이며, n은 2-4이고, W는O,NH, 또는N-(CH2)n-Q인데, 여기서 n은 2,3 또는 4의 정수이고, Q는 염소기, 브롬기, 요오드기, 황산염기, 인산염기, 토실산염기, 메실산염기 등과 같은 적당한 치환기인데, (1) W가O인 경우, Y는 H2N-(CH2)n-이고, (2) W가NH인 경우, Y는 Q-(CH2)n-또는 이며, (3) W가N-(CH2)n-Q인 경우, Y는 H로 된다.
- 제1항에 있어서, W는O이고, 반응조건은 피리딘 또는 크실렌과 같은 건식 불활성 반응매질 내에서 반응물질을 환류시키는 것을 특징으로 하는 방법.
- 제1항에 있어서, W는NH 또는N-(CH2)n-Q이고, 반응 물질은 알킬화에 의하여 이급 아민으로 부터 삼금아민을 제조하는데 적합한 조건하에 반응되는 것이 특징인 방법.
- (a) 적절한 반응 조건하에 다음 구조식(Ⅵ)의 화합물을 다음 구조식(Ⅶ)의 화합물과 반응시켜 다음 구조식 (Ⅰ)의 화합물을 얻은 다음, 이어서 (b) 구조식 (Ⅰ)의 화합물의 염이 필요한 경우에는 임으로 구조식 (Ⅰ)의 화합물을 제약상 허용되는 산과 혼합 처리하여 구조식 (Ⅰ)의 화합물의 염을 생성시키는 것을 특징으로 하는 구조식 (Ⅰ)의 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일)알킬]피페라진 유도체 또는 제약상 허용되는 그의 산부가염의 제조 방법.위 각 구조식에서, R1,R2,R2,B 및 n은 제1항에서 정의한 바와 같고, Q는 염소기, 브롬기, 요오드기, 황산염기, 인산염기, 토실산염기, 메실산염기 등의 적당한 치환기이다.
- 제1항 또는 제4항에 있어서, R1은 C1-4알킬, 트리플루오로 메틸, Z- 치환 페닐(Z는 수소 또는 할로겐)이고, R2는 Z-치환페닐이며, R3은 H2인 것이 특징인 방법.
- 제1항 또는 제4항에 있어서, R1및 R2가 결합하여 용융된 Z-치환 페닐환계(Z는 수소 또는 할로겐)가 결합된 C4-5알킬렌 브리지를 형성하고, R3은 수소인 것이 특징인 방법.
- 제1항 또는 제4항에 있어서, R1및 R3은 용융된 시클로헥세닐환 또는 X1-X|4테트라-치환 페닐환(X1-X4는 각각 수소, 할로겐 또는 니트로 중에서 선정됨)을 형성하고, R2는 존재하지 않는 것이 특징인 방법.
- 제1항 또는 제4항에 있어서, B가 2-피리미디닐인 것이 특징인 방법.
- 제4항에 있어서, 그 목적 화합물이 3-메틸-3-페닐-1-[4-[4-(2-피리미디닐)-1-피페라지닐]부틸]-2,5-피롤리딘디온 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제5항에 있어서, 그 목적 화합물이 3-(4-플루오로페닐)-3-메틸-1-[4-[4-(2-피리미디닐)-1-피페라지닐]부틸]-2,5-피롤리딘디온 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제5항에 있어서, 그 목적 화합물이 3,3-디페닐-1-[4-[4-(2-피리미디닐)-1-피페라지닐]부틸]-2,5-피롤리딘디온 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제5항에 있어서, 그 목적 화합물이 3,3-디페닐-1-[4-[4-(1,2-벤즈이소티아졸-3-일)-1-피페라지닐]부틸]-2,5-피롤리딘디온 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제6항에 있어서, 그 목적 화합물이 1'-[4-[4-(2-피리미디닐)-1-피페라지닐[부틸[스피로[1,2,3,4-테트라히드로 나프탈렌-2,3'-피롤리딘-2',5'-디온] 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제6항에 있어서, 그 목적 화합물이 1'-[4-[4-(2-피리미디닐)-1-피페라지닐[부틸[스피로[2,3-디히드로-1H-인덴-1,3'-피롤리딘-2',5'-디온] 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.
- 제7항에 있어서, 그 목적 화합물이 2-[4-[4-2-피리미디닐)-1-피페라지닐]부틸]-1H-이소인돌-1,3(2H)-디온 또는 제약상 허용되는 그의 산부가염인 것이 특징인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/531,519 US4524206A (en) | 1983-09-12 | 1983-09-12 | 1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives |
| US531,519 | 1983-09-12 | ||
| US531519 | 1995-09-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850002483A true KR850002483A (ko) | 1985-05-13 |
| KR890000566B1 KR890000566B1 (ko) | 1989-03-21 |
Family
ID=24117966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840005558A KR890000566B1 (ko) | 1983-09-12 | 1984-09-12 | 1-헤테로아릴-4-[(2,5-피롤리딘디온-1-일)알킬]피페라진유도체 및 그 제조방법 |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4524206A (ko) |
| JP (1) | JPH0647586B2 (ko) |
| KR (1) | KR890000566B1 (ko) |
| AR (1) | AR241910A1 (ko) |
| AU (1) | AU581858B2 (ko) |
| BE (1) | BE900555A (ko) |
| CA (1) | CA1285564C (ko) |
| CH (1) | CH660484A5 (ko) |
| CS (1) | CS258119B2 (ko) |
| CY (1) | CY1538A (ko) |
| DD (1) | DD224593A5 (ko) |
| DE (1) | DE3433327C2 (ko) |
| DK (1) | DK171990B1 (ko) |
| ES (1) | ES8605797A1 (ko) |
| FI (1) | FI83515C (ko) |
| FR (1) | FR2555585B1 (ko) |
| GB (1) | GB2146333B (ko) |
| GR (1) | GR80320B (ko) |
| HK (1) | HK84590A (ko) |
| HU (1) | HU192439B (ko) |
| IE (1) | IE58020B1 (ko) |
| IL (1) | IL72854A (ko) |
| IT (1) | IT1196250B (ko) |
| LU (1) | LU85537A1 (ko) |
| NL (1) | NL8402769A (ko) |
| NO (1) | NO162384B (ko) |
| NZ (1) | NZ209480A (ko) |
| OA (1) | OA07809A (ko) |
| PT (1) | PT79187B (ko) |
| SE (1) | SE463368B (ko) |
| SU (1) | SU1384199A3 (ko) |
| YU (2) | YU45655B (ko) |
| ZA (1) | ZA847065B (ko) |
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-
1983
- 1983-09-12 US US06/531,519 patent/US4524206A/en not_active Expired - Lifetime
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1984
- 1984-09-04 IL IL72854A patent/IL72854A/xx unknown
- 1984-09-06 CS CS846721A patent/CS258119B2/cs unknown
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- 1984-09-07 FI FI843522A patent/FI83515C/fi not_active IP Right Cessation
- 1984-09-07 FR FR8413765A patent/FR2555585B1/fr not_active Expired
- 1984-09-07 NZ NZ209480A patent/NZ209480A/en unknown
- 1984-09-10 GR GR80320A patent/GR80320B/el unknown
- 1984-09-10 CA CA000462755A patent/CA1285564C/en not_active Expired - Lifetime
- 1984-09-10 ES ES535780A patent/ES8605797A1/es not_active Expired
- 1984-09-10 NO NO843579A patent/NO162384B/no not_active IP Right Cessation
- 1984-09-10 YU YU156384A patent/YU45655B/sh unknown
- 1984-09-10 AU AU32870/84A patent/AU581858B2/en not_active Expired
- 1984-09-11 BE BE0/213635A patent/BE900555A/fr not_active IP Right Cessation
- 1984-09-11 PT PT79187A patent/PT79187B/pt unknown
- 1984-09-11 CH CH4341/84A patent/CH660484A5/de not_active IP Right Cessation
- 1984-09-11 SE SE8404552A patent/SE463368B/sv not_active IP Right Cessation
- 1984-09-11 NL NL8402769A patent/NL8402769A/nl active Search and Examination
- 1984-09-11 IE IE231184A patent/IE58020B1/en not_active IP Right Cessation
- 1984-09-11 GB GB08422860A patent/GB2146333B/en not_active Expired
- 1984-09-11 LU LU85537A patent/LU85537A1/xx unknown
- 1984-09-11 HU HU843427A patent/HU192439B/hu unknown
- 1984-09-11 DE DE3433327A patent/DE3433327C2/de not_active Expired - Lifetime
- 1984-09-11 JP JP59188983A patent/JPH0647586B2/ja not_active Expired - Lifetime
- 1984-09-11 SU SU843796451A patent/SU1384199A3/ru active
- 1984-09-11 IT IT22621/84A patent/IT1196250B/it active
- 1984-09-12 DD DD84267233A patent/DD224593A5/de unknown
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- 1984-09-12 KR KR1019840005558A patent/KR890000566B1/ko not_active IP Right Cessation
- 1984-09-12 AR AR84297922A patent/AR241910A1/es active
- 1984-09-12 DK DK433884A patent/DK171990B1/da not_active IP Right Cessation
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