KR900016129A - 4-알콕시알킬-4-아미노페닐피페리딘 및 그들의 유도체의 제조 방법 - Google Patents
4-알콕시알킬-4-아미노페닐피페리딘 및 그들의 유도체의 제조 방법 Download PDFInfo
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- KR900016129A KR900016129A KR1019900003205A KR900003205A KR900016129A KR 900016129 A KR900016129 A KR 900016129A KR 1019900003205 A KR1019900003205 A KR 1019900003205A KR 900003205 A KR900003205 A KR 900003205A KR 900016129 A KR900016129 A KR 900016129A
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- South Korea
- Prior art keywords
- alkyl
- group
- compound
- phenyl
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 238000004519 manufacturing process Methods 0.000 title 1
- -1 N-substituted-4-piperidone compound Chemical class 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000000129 anionic group Chemical group 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 241000125205 Anethum Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 150000002641 lithium Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- BTFHPBATCQAUBH-UHFFFAOYSA-N methyl 2-methylbenzenesulfinate Chemical compound COS(=O)C1=CC=CC=C1C BTFHPBATCQAUBH-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- YDJXNYNKKXZBMP-UHFFFAOYSA-N n-phenethyl-4-piperidinone Chemical compound C1CC(=O)CCN1CCC1=CC=CC=C1 YDJXNYNKKXZBMP-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910001023 sodium amalgam Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- (a) N-치환-4-피페리돈 화합물을 아닐린 화합물과 반응시켜 시프 염기(shiff base) 화합물을 제조하는 단계, (b) 시프염기 화합물을 음이온 안정화기를 갖는 일반식 :x-CYM-Z(상기식에서, X는 음이온 안정화기들로 구성된 군중에서 선택된 원(員)이고, Y는 수소 및 저급-알킬로 구성된 군중에서 선택된 원이고, Z는 저급-알콕시 및 페닐 메톡시로 구성된 군중에서 선택된 원이고, M은 알카리 및 알카리 토금속으로 구성된 군중에서 선택된 금속 원자이고, C는 탄소 원자임)을 갖는 음이온제와 반응시켜 아민화합물을 제조하는 단계, 및 (c) 단계 (b) 내의 아민 화합물을 환원제로 환원시켜 음이온 안정화기를 치환시키는 단계로 구성된, 4-알콕시알킬-4-아미노페닐피페디딘 화합물의 제조 방법.
- 제1항에 있어서, X가 티오페닐, 술피닐페닐, 및 술포닐페닐로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, Y가 수소, 메틸 및 에틸로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, Z가 메톡시, 에톡시, n-프토판옥시, 및 페닐메톡시로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, M이 리튬, 나트륨 및 칼륨으로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, 음이온제가 메톡시메틸 페닐 술파이드 및 메톡시 메틸페닐술폭사이드의 알카리튬 유도체로 구성된 군중에서 선택된 방법.
- 제1항에 있어서, 환원제가 라네이 닉켈, 금속 수소화물, 및 나트륨아말감으로 구성된 군중에서 선택된 원인 방법.
- 제7항에 있어서, 환원제가 n-트리부틸주석 수소화물 및 트리페닐주석 수소화물로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, N-치환-4-피페리돈 화합물이 N-페닐메틸-4-피페리돈 및 N-(2-페닐에틸)-4-피페리돈으로 구성된 군중에서 선택된 원인 방법.
- 제1항에 있어서, 4-알콕시알킬-4-아미노페닐 피페리딘 화합물이 하기 일반식을 갖는 방법 :(상기식에서, R은 페닐 및 치환된 페닐로 구성된 군중에서 선택된 원이고, R1은 수소, 저급알킬 카르보닐, 저급-알케닐 카르보닐, 저급-알콕시 저급-알킬 카르보닐 및 시클로알킬 카르보닐로 구성된 군중에서 선택된 원이고, R2는 수소, 저급-알킬, 시클로알킬메틸, 페닐 저급/알킬, 및 헤테로 시클릭 고리 시스템 저급-알킬로 구성된 군중에서 선택된 원이고, R3는 저급-알콕시, 저급-알킬 및 페닐 메톡시 저급-알킬로 구성된 군중에서 선택된 원이다.
- 제10항에 있어서, R이 페닐, 2-플루오로페닐 및 2-메톡시페닐로 구성된 군중에서 선택된 원이고, R1은 에틸 카르보닐, 에테닐카르보닐, 메톡시 메틸 카르보닐 및 메톡시에틸카르보닐로 구성된 군중에서 선택된 원이고, R2가 수소, 저급-알킬, 시클로알킬메틸, 페닐 저급/알킬, 피롤릴 저급-알킬, 피라졸릴 저급-알킬, 이미다졸릴 저급-알킬, 이미다졸리닐 저급-알킬, 이미다졸릴 저급-티오알킬, 트리아졸릴 저급-알킬, 트리아졸릴 저급-티오알킬, 테트라졸릴 저급-알킬, 테트라졸리 저급-티오알킬, 티에닐 저급-알킬, 티에닐 저급-옥시알킬, 티에닐 저급-히드록시알킬, 푸라닐 저급-히드록시알킬, 티아졸릴 저급-알킬, 옥사졸릴 저급-알킬, 티아디아졸릴 저급-알킬, 옥사디아졸릴 저급-알킬, 피리딘-1-일 저급-알킬, 피리딘-3-일 저급-알킬, 피리딘-4-일 저급-알킬, 피페리디닐 저급-알킬, 피리미디닐 저급-알킬, 피리다지닐 저급-알킬, 트리아지닐저급-알킬, 인돌일 저급-알킬, 이소인돌릴 저급-알킬, 벤즈이미다졸릴 저급-알킬, 벤조피라졸릴 저급-알킬, 벤즈옥사졸릴 저급-알킬, 벤조피라닐 저급-알킬, 벤조디옥사닐 저급-알킬, 벤조티아지닐 저급-알킬, 퀴나졸리닐 저급-알킬, 푸리닐 저급-알킬, 프탈-이미딜 저급-알킬, 나프탈렌카르복스이미딜 저급-알킬, 및 나프탈렌 술파 미딜 저급-알킬으로 구성된 군중에서 선택된 원이고, R3가 메톡시 메틸, 에톡시메틸, 메톡시에틸 및 에톡시 에틸로 구성된 군중에서 선택된 원인 방법.
- 제11항에 있어서, R이 페닐이고, R1이 에틸카르보닐이고, R2가 2-(2-티에닐)에틸 및 2-(4-에틸-4,5-디히드로-5-옥소-1H-테트라졸-1-일)에틸로 구성된 군중에서 선택된 원이고, R3가 메톡시메틸인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34097689A | 1989-04-20 | 1989-04-20 | |
| US340,976 | 1994-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900016129A true KR900016129A (ko) | 1990-11-12 |
Family
ID=23335725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900003205A Ceased KR900016129A (ko) | 1989-04-20 | 1990-03-10 | 4-알콕시알킬-4-아미노페닐피페리딘 및 그들의 유도체의 제조 방법 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0394039A1 (ko) |
| JP (1) | JPH02292259A (ko) |
| KR (1) | KR900016129A (ko) |
| AU (1) | AU613555B2 (ko) |
| NO (1) | NO901732L (ko) |
| NZ (1) | NZ233337A (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6677332B1 (en) | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| US7361666B2 (en) | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL135583C (ko) * | 1961-10-10 | |||
| US4584303A (en) * | 1984-04-09 | 1986-04-22 | The Boc Group, Inc. | N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds |
| US4791121A (en) * | 1987-11-02 | 1988-12-13 | The Boc Group, Inc. | 4-phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
-
1990
- 1990-03-10 KR KR1019900003205A patent/KR900016129A/ko not_active Ceased
- 1990-04-17 AU AU53293/90A patent/AU613555B2/en not_active Ceased
- 1990-04-18 JP JP2102758A patent/JPH02292259A/ja active Pending
- 1990-04-18 NZ NZ233337A patent/NZ233337A/xx unknown
- 1990-04-19 EP EP90304209A patent/EP0394039A1/en not_active Withdrawn
- 1990-04-19 NO NO90901732A patent/NO901732L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0394039A1 (en) | 1990-10-24 |
| AU613555B2 (en) | 1991-08-01 |
| AU5329390A (en) | 1990-11-01 |
| NZ233337A (en) | 1991-08-27 |
| NO901732L (no) | 1990-10-22 |
| NO901732D0 (no) | 1990-04-19 |
| JPH02292259A (ja) | 1990-12-03 |
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