KR910006279A - 3-(1-치환된-4-피페라지닐)-1h-인다졸, 이의 제조방법 및 이의 약제로서의 용도 - Google Patents
3-(1-치환된-4-피페라지닐)-1h-인다졸, 이의 제조방법 및 이의 약제로서의 용도 Download PDFInfo
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- KR910006279A KR910006279A KR1019900014613A KR900014613A KR910006279A KR 910006279 A KR910006279 A KR 910006279A KR 1019900014613 A KR1019900014613 A KR 1019900014613A KR 900014613 A KR900014613 A KR 900014613A KR 910006279 A KR910006279 A KR 910006279A
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- 239000003814 drug Substances 0.000 title claims 2
- -1 3- (1-substituted-4-piperazinyl) -1H-indazole Chemical class 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- BGZHQWWHHIRZNP-UHFFFAOYSA-N 1-ethyl-3-(4-methylpiperazin-1-yl)indazole Chemical compound C12=CC=CC=C2N(CC)N=C1N1CCN(C)CC1 BGZHQWWHHIRZNP-UHFFFAOYSA-N 0.000 claims 1
- QEGQWEDKMMRTLW-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-1h-indazole Chemical compound C1CN(C)CCN1C1=NNC2=CC=CC=C12 QEGQWEDKMMRTLW-UHFFFAOYSA-N 0.000 claims 1
- WLQSMLQXWNWIMU-UHFFFAOYSA-N 3-[3-[4-(6-fluoro-1h-indazol-3-yl)piperazin-1-yl]propyl]-1h-benzimidazol-2-one Chemical compound C12=CC=CC=C2NC(=O)N1CCCN(CC1)CCN1C1=NNC2=CC(F)=CC=C21 WLQSMLQXWNWIMU-UHFFFAOYSA-N 0.000 claims 1
- CZDPWCSDFMYTRB-UHFFFAOYSA-N 3-[4-[3-(2-methyl-1h-indol-3-yl)propyl]piperazin-1-yl]-1h-indazole Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC=3C4=CC=CC=C4NC=3C)=NNC2=C1 CZDPWCSDFMYTRB-UHFFFAOYSA-N 0.000 claims 1
- TZLAQZDPHGVCQU-UHFFFAOYSA-N 3-[4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCN(C=2C3=CC=CC=C3NN=2)CC1 TZLAQZDPHGVCQU-UHFFFAOYSA-N 0.000 claims 1
- HCNSJWYUKDBQNO-UHFFFAOYSA-N 3-piperazin-1-yl-1h-indazole Chemical compound C1CNCCN1C1=NNC2=CC=CC=C12 HCNSJWYUKDBQNO-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000000561 anti-psychotic effect Effects 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides 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
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 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
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
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- 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
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (13)
- 일반식(Ⅰ)의 화합물 및 이의 약학적으로 허용되는 산 부가염, 적용되는 경우 이들의 기하 이성체 및 광학 이성체 및 이들의 라세미체 혼합물.상기식에서, R1은 수소, 저급 알킬, 아릴 저급 알킬, 아실, 사이클로알킬 저급 알킬렌 또는 페닐설포닐이고, R2는 수소, 저급 알킬, 구조식-(저급 알킬렌)-OH의 하이드록시 저급 알킬, 아릴 저급 알킬, 아실 사이클로알킬 저급 알킬렌.(여기에서, Z는 수소, 할로겐 저급 알콕시, CF3, NO2및 NH2중에서 선택된다);(여기에서, Z는 전술한 바와 같다);(여기에서, Z는 전술한 바와 같다);(여기에서, R3및 R4는 각각 독립적으로 수소 및 저급 알킬이다);(여기에서, Z는 전술한 바와 같다);(여기에서 R' 및 R″는 각각 독립적으로 수소 및 저급 알킬이다)이며, X는 수소, 저급 알킬, 하이드록실, 할로겐, 저급 알콕시, CF3, NO2및 NH2이며, n은 1 내지 4의 정수이며, 단, R1이 수소 또는 아실이고 X는 클로로인 경우 R2는 저급 알킬이 아니다.
- 제1항에 있어서, R1이 수소, 저급 알킬, 아실 또는 사이클로알킬-저급 알킬렌이고 R2가 수소, 저급 알킬 하이드록시 저급 알킬 또는 일반식의 화합물이고 X가 수소, 저급 알콕시 또는 할로겐이며 n이 1인 화합물.
- 제2항에 있어서, R1이 수소, 메틸, 에틸, 아세틸, 벤조일 또는 사이클로프로필메틸인 화합물.
- 제1항에 있어서, 3-(4-메틸-1-피페라지닐)-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 제1항에 있어서, 1-에틸-3-(4-메틸-1-피페라지닐)-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 제1항에 있어서, 3-(1-피페라지닐)-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 제1항에 있어서, 8-〔4-〔1-(1H-인다졸-3-일)-4-피페라지닐〕부틸-8-아자스피로〔4,5〕데칸-7,9-디온인 화합물.
- 제1항에 있어서, 3-〔4-〔4,4-비스(4-플루오로페닐)부틸〕-1-피페라지닐〕-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 제1항에 있어서, 3-〔4-〔3-(2-메틸인돌-3-일)프로필〕-1-피페라지닐〕-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 제1항에 있어서, 6-플루오로-3-〔4-〔3-(1,3-디하이드로-2-옥소-2H-벤즈이미다졸-1일)프로필〕-1-피페라지닐〕-1H-인다졸인 화합물 또는 이의 약학적으로 허용되는 산부가염.
- 활성성분으로서 제1항에 따른 화합물 및 이에 대한 적합한 담체를 포함하는 약학 조성물.
- 진통 활성 및/또는 정신병 억제 활성이 있는 약제를 제조하기 위한 화합물의 용도.
- a) 일반식(Ⅷ)의 화합물을 축합하여 R1이 페닐 설포닐이고 R2가 저급 알킬인 일반식(Ⅰ)의 화합물을 형성시키고, b) 단계 a)에서 수득한 일반식(Ⅰ)의 화합물을 할로시아나이드와 임의로 반응시켜 R2가 CN인 일반식(Ⅰ)의 화합물을 형성시키고 수득한 화합물을 금속 하이드라이드로 환원시켜 x 및 n이 전술한 바와 같고 R1및 R2모두가 수소인 일반식(Ⅰ)의 화합물을 형성시키거나, c) 단계a)에서 수득한 일반식(Ⅰ)의 화합물을 강염기와 임의로 반응시켜 X및 n이 전술한 바와 같고, R1이 수소이며 R2가 저급 알킬인 일반식( I )의 화합물을 형성시키고, d) 단계 e)에서 수득되는 일반식( I )의 화합물을 할로시아나이드와 임의로 반응시켜 x 및 n이 전술한 바와 같고 R1이 수소이고 R2가 CN인 일반식(Ⅰ)의 화합물을 형성시키고 수득된 화합물을 금속 하이드라이드로 환원시켜 X 및 n이 전술한 바와 같고 R1및 R2가 모두가 수소인 일반식(Ⅰ)의 화합물을 형성시키며, e) X 및 n이 전술한 바와 같고 R1및 R2모두가 수소인 일반식(Ⅰ)의 화합물을 일반식 R2Y(여기에서, Y는 클로로 또는 브로모이고 R2는 하이드록시 저급 알킬, 저급 알킬, 아릴 저급 알킬, 사이클로알킬 저급 알킬렌 또는 구조식라디칼이다)의 화합물과 임의로 반응시켜 x', n 및 R2가 전술한 바와 같고 R1이 수소인 일반식(Ⅰ)의 화합물을 형성시키며, f) X 및 n이 전술한 바와 같고 R1이 수소이고 R2가 저급 알킬인 일반식(Ⅰ)의 화합물을 일반식(여기에서, Haℓ은 클로로 또는 브로모이고 R8은 저급 알킬 또는 아릴이다)의 화합물과 임의로 반응시켜 X 및 n이 전술한 바와 같고 R1이 그룹 R8CO이고 R2가 저급 알킬인 일반식(Ⅰ)의 화합물을 형성시키며, g) X 및 n이 전술한 바와 같고 R1은 수소이며 R2가 저급 알킬인 일반식(Ⅰ)의 화합물을 일반식 R1Haℓ(여기에서, Haℓ은 클로로 또는 브로모이고 R1은 저급 알킬, 아릴 저급 알킬 또는 사이클로알킬 저급 알킬이다)의 화합물과 임의로 반응시켜 X, n 및 R1이 전술한 바와 같고 R2가 저급 알킬인 일반식(Ⅰ)의 화합물을 형성시킴을 특징으로 하여 제1항에 따른 화합물을 제조하는 방법.상기식에서, R2는 저급 알킬이고, X 및 n은 전술한 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US405161 | 1989-09-11 | ||
US07/405,161 US4954503A (en) | 1989-09-11 | 1989-09-11 | 3-(1-substituted-4-piperazinyl)-1H-indazoles |
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KR910006279A true KR910006279A (ko) | 1991-04-29 |
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KR1019900014613A KR910006279A (ko) | 1989-09-11 | 1990-09-11 | 3-(1-치환된-4-피페라지닐)-1h-인다졸, 이의 제조방법 및 이의 약제로서의 용도 |
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US (1) | US4954503A (ko) |
EP (1) | EP0417653A1 (ko) |
JP (1) | JPH03167175A (ko) |
KR (1) | KR910006279A (ko) |
AU (1) | AU6229890A (ko) |
CA (1) | CA2024996A1 (ko) |
FI (1) | FI904419A0 (ko) |
IE (1) | IE903286A1 (ko) |
IL (1) | IL95633A0 (ko) |
NO (1) | NO903925L (ko) |
PT (1) | PT95260A (ko) |
ZA (1) | ZA907174B (ko) |
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US5134236A (en) * | 1987-08-07 | 1992-07-28 | Hoechst-Roussel Pharmaceuticals Incorporated | Phenylhydrazones as intermediates 1-phenyl-3-(1-piperazenyl)-1H-indazoles |
US5017573A (en) * | 1988-07-29 | 1991-05-21 | Dainippon Pharmaceutical Co., Ltd. | Indazole-3-carboxylic acid derivatives |
US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
US5776963A (en) | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
US5328920A (en) * | 1991-04-17 | 1994-07-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted (pyridinylamino)-indoles |
US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
US5225412A (en) * | 1991-04-29 | 1993-07-06 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzoisothiazole-and benzisoxazole-3-carboxamides |
IT1251144B (it) * | 1991-07-30 | 1995-05-04 | Boehringer Ingelheim Italia | Derivati del benzimidazolone |
US5380944A (en) * | 1992-03-04 | 1995-01-10 | Kumiai Chemical Industry Co., Ltd. | Benzhydrazone derivatives as an intermediate for the production of triazole derivatives |
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NZ230045A (en) * | 1988-08-05 | 1990-11-27 | Janssen Pharmaceutica Nv | 3-piperazinylbenzazole derivatives and pharmaceutical compositions |
-
1989
- 1989-09-11 US US07/405,161 patent/US4954503A/en not_active Expired - Lifetime
-
1990
- 1990-09-07 FI FI904419A patent/FI904419A0/fi not_active IP Right Cessation
- 1990-09-07 EP EP90117251A patent/EP0417653A1/en not_active Withdrawn
- 1990-09-10 AU AU62298/90A patent/AU6229890A/en not_active Abandoned
- 1990-09-10 NO NO90903925A patent/NO903925L/no unknown
- 1990-09-10 JP JP2237300A patent/JPH03167175A/ja active Pending
- 1990-09-10 ZA ZA907174A patent/ZA907174B/xx unknown
- 1990-09-10 PT PT95260A patent/PT95260A/pt not_active Application Discontinuation
- 1990-09-10 IE IE328690A patent/IE903286A1/en unknown
- 1990-09-10 IL IL95633A patent/IL95633A0/xx unknown
- 1990-09-10 CA CA002024996A patent/CA2024996A1/en not_active Abandoned
- 1990-09-11 KR KR1019900014613A patent/KR910006279A/ko not_active Application Discontinuation
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IE903286A1 (en) | 1991-04-10 |
ZA907174B (en) | 1991-06-26 |
NO903925L (no) | 1991-03-12 |
AU6229890A (en) | 1991-03-14 |
JPH03167175A (ja) | 1991-07-19 |
PT95260A (pt) | 1991-05-22 |
CA2024996A1 (en) | 1991-03-12 |
EP0417653A1 (en) | 1991-03-20 |
IL95633A0 (en) | 1991-06-30 |
NO903925D0 (no) | 1990-09-10 |
FI904419A0 (fi) | 1990-09-07 |
US4954503A (en) | 1990-09-04 |
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