KR850002270A - 항우울증 작용을 가진 1,2,4-트리아졸론 화합물의 제조 방법 - Google Patents
항우울증 작용을 가진 1,2,4-트리아졸론 화합물의 제조 방법 Download PDFInfo
- Publication number
- KR850002270A KR850002270A KR1019840006041A KR840006041A KR850002270A KR 850002270 A KR850002270 A KR 850002270A KR 1019840006041 A KR1019840006041 A KR 1019840006041A KR 840006041 A KR840006041 A KR 840006041A KR 850002270 A KR850002270 A KR 850002270A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- hydrogen
- pharmaceutically acceptable
- chlorophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- -1 1,2,4-triazolone compound Chemical class 0.000 title claims 4
- 230000001430 anti-depressive effect Effects 0.000 title 1
- 239000000935 antidepressant agent Substances 0.000 title 1
- 229940005513 antidepressants Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NDQKGEFMUGSRNS-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC(Cl)=C1 NDQKGEFMUGSRNS-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- WLVZLZINXQKTMZ-UHFFFAOYSA-N 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4-ethyl-5-(1-hydroxyethyl)-1,2,4-triazol-3-one Chemical compound O=C1N(CC)C(C(C)O)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 WLVZLZINXQKTMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 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
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000003903 lactic acid esters Chemical class 0.000 claims 1
- 125000004184 methoxymethyl group Chemical class [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 (8)
- (a) 히드라진을 적합한 반응 조건 하에 다음 구조식(Ⅵ)의 적절히 보호된 젖산 에스테르와 반응시켜 다음 구조식 (Ⅴ)의 히드라지드 중간체를 얻고,(b) 이 히드라지드 중간체(Ⅴ)를 적합한 반응 조건하에 다음 구조식(Ⅶ)의 화합물과 반응시켜서 다음구조식(Ⅳ)의 화합물을 얻고,(c) 이 화합물(Ⅳ)를 환화 조건하에 환류시켜 다음 구조식(Ⅲ)의 화합물을 얻고,(d) 이 화합물(Ⅲ)을 1-(3-클로로프로필)-4-(3-클로로페닐) 피페라진으로 알킬화시킨 다음 묽은산을 사용하여 보호기 P를 분리시켜서 다음 구조식(Ⅰ)에서 R가 수소인 화합물을 얻고,(e) 이 구조식(Ⅰ)에서 R가 수소가 아닌 화합물을 얻고자 하는 경우에는 R가 수소인 구조식(Ⅰ)의 화합물을 알킬화 조건하에 화합물 RX(여기서, R는 수소가 아님)와 반응시켜 구조식(Ⅰ)의 화합물(여기서, R은 수소가 아님)을 얻은 다음.(f) 구조식(Ⅰ)화합물의 제약상 허용되는 염을 얻고자 하는 경우에는 구조식(Ⅰ)이 화합물 [R가 수소인 것은 (d)에서 얻은 것, 또는 R가 수소가 아닌 것은 (e)에서 얻은 것]을 적당한 유기산 또는 무기산과 용액 중에서 접촉 반응시켜 구조식(Ⅰ)화합물의 제약상 허용되는 염을 얻는 것이 특징인 다음 구조식(Ⅰ)의 1,2,4-트리아졸론 화합물 또는 이것의 제약상 허용되는 염의 제조 방법.위 각 구조식에서, R는 수소, 저급(C1-C4)알킬, 저급 아실, 페닐-저급 알킬 또는 페닐-저급 아실이고, n은 2-4이며, Y는 할로겐 또는 트리플루오로메틸이고, Z는 수소 또는(여기서, R1은 수소, 할로겐, 저급 알콕시 또는 트리플루오로메틸이다.)이며, P는 산에 불안정한 보호기(바람직하게는 메톡시메틸모핵), 저급(C1-C4)알킬 또는 알킬페닐이다.
- 제1항에 있어서, R가 수소인 방법.
- 제1항에 있어서, Y가 3-클로로인 방법.
- 제1항에 있어서, R가 벤질인 방법.
- 제1항에 있어서, Z가 페닐옥시인 방법.
- 제2항에 있어서, Y가 3-클로로인 방법.
- 제1항에 있어서, 구조식(Ⅰ)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-5-(1-히드록시에틸)-2,4-디히드로-4-(2-펜옥시에틸)-3H-1,2,4-트리아졸-3은 또는 이것의 제약상 허용되는 산부가염인 방법.
- 제1항에 있어서, 구조식(Ⅰ)의 화합물이 2-[3-[4-(3-클로로페닐)-1-피페라지닐]프로필]-4-에틸-5-(1-히드록시에틸)-2H-1,2,4-트리아졸-3(4H)-온 또는 이것의 제약상 허용되는 산부가염인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US538,027 | 1983-09-30 | ||
US06/538,027 US4613600A (en) | 1983-09-30 | 1983-09-30 | Antidepressant 1,2,4-triazolone compounds |
US538027 | 1983-09-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850002270A true KR850002270A (ko) | 1985-05-10 |
KR880002624B1 KR880002624B1 (ko) | 1988-12-07 |
Family
ID=24145128
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840006041A KR880002624B1 (ko) | 1983-09-30 | 1984-09-29 | 항우울증 작용을 가진 1,2,4-트리아졸론 화합물 및 그 제조방법 |
Country Status (25)
Country | Link |
---|---|
US (1) | US4613600A (ko) |
JP (1) | JPS60100560A (ko) |
KR (1) | KR880002624B1 (ko) |
AT (1) | AT387963B (ko) |
AU (1) | AU561460B2 (ko) |
BE (1) | BE900714A (ko) |
CA (1) | CA1237723A (ko) |
CH (1) | CH661924A5 (ko) |
CY (1) | CY1541A (ko) |
DE (1) | DE3435745C2 (ko) |
DK (1) | DK169546B1 (ko) |
ES (1) | ES536286A0 (ko) |
FI (1) | FI83310C (ko) |
FR (1) | FR2552759B1 (ko) |
GB (1) | GB2147297B (ko) |
GR (1) | GR80475B (ko) |
HK (1) | HK37391A (ko) |
IE (1) | IE58084B1 (ko) |
IT (1) | IT1178522B (ko) |
LU (1) | LU85561A1 (ko) |
MY (1) | MY102123A (ko) |
NL (1) | NL8402946A (ko) |
SE (1) | SE465928B (ko) |
YU (1) | YU45667B (ko) |
ZA (1) | ZA847589B (ko) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4487773A (en) * | 1981-03-16 | 1984-12-11 | Mead Johnson & Company | 1,2,4-Triazol-3-one antidepressants |
YU44721B (en) * | 1983-11-30 | 1990-12-31 | Bristol Myers Co | Process for obtaining 4-(2-phenoxyethyl)-1,2,4-triazolone |
CA1331757C (en) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
US5504086A (en) * | 1989-10-17 | 1996-04-02 | Ellinwood, Jr.; Everett H. | Intraoral dosing method of administering trifluorobenzodiazepines, propoxyphene, and nefazodone |
US5256664A (en) * | 1992-04-28 | 1993-10-26 | Bristol-Myers Squibb Company | Antidepressant 3-halophenylpiperazinylpropyl derivatives of substituted triazolones and triazoldiones |
DE4425144A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
US6403593B1 (en) | 1995-07-14 | 2002-06-11 | Abbott Laboratories | Triazole compounds and the use thereof |
DE19728996A1 (de) | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
US6586437B2 (en) | 1999-04-09 | 2003-07-01 | Sepracor Inc. | (S)-hydroxynefazodone antipsychotic therapy |
US6469008B2 (en) | 1999-04-09 | 2002-10-22 | Sepracor Inc. | (R)-hydroxynefazodone antipsychotic therapy |
AU4215400A (en) * | 1999-04-09 | 2000-11-14 | Sepracor, Inc. | S-hydroxynefazodone |
CA2369732A1 (en) | 1999-04-09 | 2000-10-19 | Sepracor Inc. | R-hydroxynefazodone |
EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
EP1737473A4 (en) * | 2004-04-19 | 2009-08-26 | Noven Therapeutics Llc | COMBINATIONS OF LITHIUM AND USES THEREOF |
CN101287411B (zh) | 2005-04-28 | 2013-03-06 | 普罗秋斯生物医学公司 | 药物信息系统及其用途 |
CA2663377A1 (en) | 2006-09-18 | 2008-03-27 | Raptor Pharmaceutical Inc. | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
WO2009111031A2 (en) * | 2008-03-04 | 2009-09-11 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
NZ594310A (en) | 2009-02-20 | 2014-02-28 | To Bbb Holding B V | Glutathione-based drug delivery system |
MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
WO2012072665A1 (en) | 2010-11-30 | 2012-06-07 | Pharmaneuroboost N.V. | Compositions comprising pipamperone and serotonin antagonist reuptake inhibitors |
AU2012304407A1 (en) * | 2011-09-09 | 2014-04-24 | Children's Hospital & Research Center Oakland | Topical itraconazole formulations and uses thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1066857B (it) * | 1965-12-15 | 1985-03-12 | Acraf | Derivati della s ipiazolo 4.3 a piridina e processi per la loro preparazione |
IT1052119B (it) * | 1972-10-16 | 1981-06-20 | Sigma Tau Ind Farmaceuti | Derivati del triazolinone e procedimento per la loro preparazione |
US4338317A (en) * | 1981-03-16 | 1982-07-06 | Mead Johnson & Company | Phenoxyethyl-1,2,4,-triazol-3-one antidepressants |
-
1983
- 1983-09-30 US US06/538,027 patent/US4613600A/en not_active Expired - Lifetime
-
1984
- 1984-09-26 FI FI843779A patent/FI83310C/fi not_active IP Right Cessation
- 1984-09-26 ZA ZA847589A patent/ZA847589B/xx unknown
- 1984-09-26 GR GR80475A patent/GR80475B/el unknown
- 1984-09-27 NL NL8402946A patent/NL8402946A/xx active Search and Examination
- 1984-09-27 ES ES536286A patent/ES536286A0/es active Granted
- 1984-09-28 IE IE247684A patent/IE58084B1/en not_active IP Right Cessation
- 1984-09-28 GB GB08424535A patent/GB2147297B/en not_active Expired
- 1984-09-28 DE DE3435745A patent/DE3435745C2/de not_active Expired - Lifetime
- 1984-09-28 CH CH4675/84A patent/CH661924A5/de not_active IP Right Cessation
- 1984-09-28 JP JP59202142A patent/JPS60100560A/ja active Granted
- 1984-09-28 DK DK468284A patent/DK169546B1/da not_active IP Right Cessation
- 1984-09-28 IT IT22922/84A patent/IT1178522B/it active
- 1984-09-28 AU AU33648/84A patent/AU561460B2/en not_active Expired
- 1984-09-28 BE BE0/213750A patent/BE900714A/fr not_active IP Right Cessation
- 1984-09-28 LU LU85561A patent/LU85561A1/fr unknown
- 1984-09-28 CA CA000464230A patent/CA1237723A/en not_active Expired
- 1984-09-28 FR FR8414932A patent/FR2552759B1/fr not_active Expired
- 1984-09-28 SE SE8404869A patent/SE465928B/sv not_active IP Right Cessation
- 1984-09-29 KR KR1019840006041A patent/KR880002624B1/ko not_active IP Right Cessation
- 1984-10-01 AT AT0310884A patent/AT387963B/de not_active IP Right Cessation
- 1984-10-05 YU YU172184A patent/YU45667B/sh unknown
-
1987
- 1987-10-01 MY MYPI87002743A patent/MY102123A/en unknown
-
1991
- 1991-03-22 CY CY1541A patent/CY1541A/xx unknown
- 1991-05-16 HK HK373/91A patent/HK37391A/xx not_active IP Right Cessation
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