KR840001166A - 스피로티아졸리딘일 피페라진 유도체 제조방법 - Google Patents
스피로티아졸리딘일 피페라진 유도체 제조방법 Download PDFInfo
- Publication number
- KR840001166A KR840001166A KR1019820003481A KR820003481A KR840001166A KR 840001166 A KR840001166 A KR 840001166A KR 1019820003481 A KR1019820003481 A KR 1019820003481A KR 820003481 A KR820003481 A KR 820003481A KR 840001166 A KR840001166 A KR 840001166A
- Authority
- KR
- South Korea
- Prior art keywords
- azaspiro
- thia
- butyl
- nonan
- piperazinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- -1 1 -substituted phenyl Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- KYQWKVHYBNLXGX-UHFFFAOYSA-N 2-[4-[4-(2,4-dioxo-1-thia-3-azaspiro[4.4]nonan-3-yl)butyl]piperazin-1-yl]pyridine-3-carbonitrile;hydrochloride Chemical compound Cl.O=C1N(CCCCN2CCN(CC2)C=2C(=CC=CN=2)C#N)C(=O)SC21CCCC2 KYQWKVHYBNLXGX-UHFFFAOYSA-N 0.000 claims 1
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 claims 1
- IOOWZEYQYCHTDP-UHFFFAOYSA-N 3-oxononanal Chemical compound CCCCCCC(=O)CC=O IOOWZEYQYCHTDP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- MFVFFBLHOYEENF-UHFFFAOYSA-N FC(F)(F)[P] Chemical compound FC(F)(F)[P] MFVFFBLHOYEENF-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 충분한 시간동안 50℃-200℃의 온도의 염기의 존재 또는 비존재하에, 비활성반응 매개물질에서, 하기 구조식(Ⅱ)의 스피로-2,4-티아졸리딘디온과 하기 구조식(Ⅲ)의 피페리딘을 반응시켜 하기 구조식 Ⅰ화합물을 생성하고, 필요하다면, 하기 구조식 화합물을 염으로 전환시키거나 또는 유리화합물 또는 또다른 염으로 전환시키는 것을 특징으로 하는 하기 구조식 Ⅰ을 갖는 스피로티아졸리딘디온의 제조방법.
-
- 여기서, Z는 구조식인 R1-치환된 페닐이며, R1은 수소, 할로겐, 저급알킬, 저급알콕시 또는 트리플루오로메틸, 구조식인 R2-치환된 2-피리딘일라디칼이며; R2는 수소 또는 시아노 또는 그의 의약적 허용가능한 비-독성 부가염이고; A는 독립적으로, 수소, 알칼리 금속염, 또는 라디칼 X-(CH2)4-이고 : X는 반응에스테르 원자단의 산잔사이다.
- 제1항에 있어서, 2-클로로-3-시아노피리딘과 피페라진을 알코올에서 1-(3-시아노-2-피리딘일피페라진을 산출하기에 충분한 시간동안 반응시키는 것과 그후 2-[4-[4-(7,9-디옥소-6-티아-8-아자스피로[4,4]-노난-8-일)부틸]-1-피페라진일]피리딘-3-카르보니트릴의 유리염기를 얻기 위한 충분한 시간동안 환류비활성용매내에서 염기의 존재하에, 상기 1-(3-시아노-2-피리딘일)-피페리진과 3-(4-브로모부틸)-5-스피로시클로펜틸-2,4-티아졸리딘디온을 반응시키는 것과, 그런후 상기 유리 염기를 융점 207-208℃인 염화수소염(Ia)로 전환시키는 단계로 구성되는 것을 특징으로하는 구조식(Ia)의 화합물의 제조방법.
-
- 실시예 1,2,3,4,5 및 6에 설명된 방법.
- 구조식 Ⅰ의 스피로티아졸리딘디온과 8-[4-[4-클로로페닐]-1-피페라진일]부틸]-6-티아-8-아자스피로[4,4]노난-7,9-디온 또는 그의 의약적 허용가능한 염 및 2-[4-[4-(7,9-디옥소-6-티아-8-아자스피로[4,4]노난-8-일)부틸]-1-피페라진일]피리딘-3-카르보니트릴 또는 그의 의약적 허용가능한 염의 화합물중 한가지를 포함하는 것을 특징으로하는 의약적 조성물.
- 8-[4-[4-클로로-페닐-1-피페라진일]부틸]-6-티아-8-아자스피로[4.4]노난-7,9-디온디히드로클로라이드 및 2-[4-[4-(7,9-디옥소-6-티아-8-아자스피로[4.4]노난-8-일)부틸]-1-피페라진일]피리딘-3-카르보니트릴히드로클로라이드의 화합물을 포함하는 것을 특징으로 하는 의약적 조성물.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US289.351 | 1981-08-03 | ||
| US289,351 | 1981-08-03 | ||
| US06/289,351 US4456756A (en) | 1981-08-03 | 1981-08-03 | Spirothiazolidinyl piperazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840001166A true KR840001166A (ko) | 1984-03-28 |
| KR880001737B1 KR880001737B1 (ko) | 1988-09-10 |
Family
ID=23111156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8203481A KR880001737B1 (ko) | 1981-08-03 | 1982-08-03 | 스피로티아졸리디닐 피페라진 유도체 및 그의 제조방법 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4456756A (ko) |
| JP (1) | JPS5838277A (ko) |
| KR (1) | KR880001737B1 (ko) |
| AT (1) | AT380477B (ko) |
| AU (1) | AU555870B2 (ko) |
| BE (1) | BE894021A (ko) |
| CA (1) | CA1208642A (ko) |
| CH (1) | CH655503B (ko) |
| DE (1) | DE3228992A1 (ko) |
| DK (1) | DK156219C (ko) |
| ES (2) | ES8401763A1 (ko) |
| FI (1) | FI76794C (ko) |
| FR (1) | FR2510571B1 (ko) |
| GB (1) | GB2105714B (ko) |
| GR (1) | GR76171B (ko) |
| HU (1) | HU191505B (ko) |
| IE (1) | IE53613B1 (ko) |
| IL (1) | IL66433A (ko) |
| IT (1) | IT1149026B (ko) |
| LU (1) | LU84315A1 (ko) |
| NL (1) | NL8203035A (ko) |
| NZ (1) | NZ201158A (ko) |
| OA (1) | OA07171A (ko) |
| PH (1) | PH18688A (ko) |
| PT (1) | PT75365B (ko) |
| SE (1) | SE453503B (ko) |
| YU (1) | YU44073B (ko) |
| ZA (1) | ZA825481B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61162278A (ja) * | 1985-01-09 | 1986-07-22 | Nippon Yakin Kogyo Co Ltd | 冷却手段を具えたロ−ラ−電極を含む自走式シ−ム溶接機 |
| US4619930A (en) * | 1985-01-16 | 1986-10-28 | Bristol-Myers Company | Antipsychotic cyclic imide derivatives of 2-(4-butylpiperazin-1-yl)pyridines, compositions and use |
| US4677104A (en) * | 1985-05-06 | 1987-06-30 | Bristol-Myers Company | Antipsychotic fused-ring pyridinylpiperazine derivatives |
| US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
| EP0316723B1 (en) * | 1987-11-20 | 1992-09-30 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-[4(1-Substituted-4-piperazinyl)butyl]-4-thiazolidinones a process for their preparation and their use as medicaments |
| US5801186A (en) * | 1987-11-20 | 1998-09-01 | Hoechst Marion Roussel, Inc. | 3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds |
| JPH0270878U (ko) * | 1988-11-21 | 1990-05-30 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT649883A (ko) * | 1960-05-24 | |||
| US3106552A (en) * | 1960-07-19 | 1963-10-08 | Geschickter Fund Med Res | Nu-substituted azaspiranes and azaspirane-diones and processes for their preparation |
| US3200118A (en) * | 1961-10-31 | 1965-08-10 | Geschickter Fund Med Res | Spirocyclic hydrazine imides |
| US3432499A (en) * | 1965-04-02 | 1969-03-11 | Geschickter Fund Med Res | Trifluoromethylazaspiranes and azaspirane diones |
| US3398151A (en) * | 1966-02-01 | 1968-08-20 | Mead Johnson & Co | Azaspirodecanediones and azaspiroundecanediones |
| DE1695410A1 (de) * | 1967-04-20 | 1971-04-08 | Merck Patent Gmbh | Verfahren zur Herstellung von 1-(Thiazolyl-5-alkyl)-4-(pyridyl-2)-piperazinen |
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| US3976776A (en) * | 1972-12-06 | 1976-08-24 | Mead Johnson & Company | Tranquilizer process employing N-(heteroarcyclic)piperazinylalkylazaspiroalkanediones |
| DE2862059D1 (en) * | 1977-12-29 | 1982-11-11 | Synthelabo | Thiazolidinedione-2,4 derivatives, their preparation and pharmaceutical applications |
| IL57569A0 (en) * | 1978-06-20 | 1979-10-31 | Synthelabo | Phenylpiperazine derivative,their preparation and pharmaceutical compositions containing them |
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
-
1981
- 1981-08-03 US US06/289,351 patent/US4456756A/en not_active Expired - Fee Related
-
1982
- 1982-07-05 NZ NZ201158A patent/NZ201158A/en unknown
- 1982-07-13 GR GR68740A patent/GR76171B/el unknown
- 1982-07-13 AU AU85973/82A patent/AU555870B2/en not_active Ceased
- 1982-07-20 YU YU1585/82A patent/YU44073B/xx unknown
- 1982-07-23 ES ES514263A patent/ES8401763A1/es not_active Expired
- 1982-07-28 IT IT48901/82A patent/IT1149026B/it active
- 1982-07-28 FR FR8213176A patent/FR2510571B1/fr not_active Expired
- 1982-07-29 ZA ZA825481A patent/ZA825481B/xx unknown
- 1982-07-29 NL NL8203035A patent/NL8203035A/nl not_active Application Discontinuation
- 1982-07-30 FI FI822666A patent/FI76794C/fi not_active IP Right Cessation
- 1982-07-30 IE IE1851/82A patent/IE53613B1/en unknown
- 1982-07-30 CA CA000408451A patent/CA1208642A/en not_active Expired
- 1982-07-30 PH PH27655A patent/PH18688A/en unknown
- 1982-07-30 DK DK343782A patent/DK156219C/da not_active IP Right Cessation
- 1982-08-01 IL IL66433A patent/IL66433A/xx unknown
- 1982-08-02 HU HU822483A patent/HU191505B/hu not_active IP Right Cessation
- 1982-08-02 GB GB08222210A patent/GB2105714B/en not_active Expired
- 1982-08-02 PT PT75365A patent/PT75365B/pt not_active IP Right Cessation
- 1982-08-02 SE SE8204549A patent/SE453503B/sv not_active IP Right Cessation
- 1982-08-02 CH CH466082A patent/CH655503B/de unknown
- 1982-08-03 BE BE0/208747A patent/BE894021A/fr not_active IP Right Cessation
- 1982-08-03 JP JP57134807A patent/JPS5838277A/ja active Granted
- 1982-08-03 DE DE19823228992 patent/DE3228992A1/de not_active Withdrawn
- 1982-08-03 OA OA57764A patent/OA07171A/xx unknown
- 1982-08-03 KR KR8203481A patent/KR880001737B1/ko active
- 1982-08-03 LU LU84315A patent/LU84315A1/fr unknown
- 1982-08-03 AT AT0299382A patent/AT380477B/de active
-
1983
- 1983-09-30 ES ES526149A patent/ES8504185A1/es not_active Expired
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