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KR830006217A - 9-아미노-1-하이드록시옥타하이드로벤조[c] 퀴놀린의 제조방법 - Google Patents

9-아미노-1-하이드록시옥타하이드로벤조[c] 퀴놀린의 제조방법 Download PDF

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KR830006217A
KR830006217A KR1019810002717A KR810002717A KR830006217A KR 830006217 A KR830006217 A KR 830006217A KR 1019810002717 A KR1019810002717 A KR 1019810002717A KR 810002717 A KR810002717 A KR 810002717A KR 830006217 A KR830006217 A KR 830006217A
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carbon atoms
hydrogen
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KR850000273B1 (ko
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로스 죤슨 미카엘
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윌리암 지. 멕크리리
화이자 인코포레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C07D221/12—Phenanthridines

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
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Abstract

내용 없음

Description

9-아미노-1-하이드록시옥타하이드로벤조[C] 퀴놀린의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (1)

  1. (a) 구조식(Ⅱ)의 화합물을 암모니아 또는 암모니아의 산부가염 및 환원제와 반응 불활성용매 존재하에 반응시켜 R이 수소인 구조식(Ⅰ)의 화합물을 제조하고, R이 COR7또는 SO2R8인 구조식(Ⅰ) 화합물을 목적으로 하는 경우에는 이를 구조식 R7CORa(Ra는 OH, 탄소원자 1 내지 4개의 알콕시, C1 또는 Br) 또는 (R7CO)2O의 화합물로 아실화하거나 구조식 R8CO2Rb(Rb는 OH, C1 또는 Br)의 화합물로 설폰화시키며, (b) 구조식(Ⅱ)의 화합물을 포름산과 암모늄 포르메이트 또는 그의 산부가염과 반응시킨후 옥심을 반응 불활성 용매 존재하에 촉매적 수소화시킴으로써 R이 수소인 구조식(Ⅰ)의 화합물을 제조하고 경우에 따라 상기와 같이 아실화 또는 설포닐화시키며 (d) Z가 후에 정의되는 알킬렌 또는 -(alk1)m-O-(alk2)n-이며, R4가 베타-치환제인 구조식(Ⅱ)의 에논을 하이드록실아민 또는 그의 산부가염과 용매, 바람직하게는 피리딘 존재하에 반응시켜 구조식(Ⅳ)의 옥심 중간물질을 제조하고 이 옥심 중간물질을 팔라륨, 바람직하게는 팔라륨/탄소 촉매 존재하에 수소화시키며, 경우에 따라 상기와 같이 아실화 또는 설포닐화시켜 구조식(IA)의 6a, 10a,-트랜스-9-베타-아미노 화합물을 제조함을 특징으로하는 구조식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
    상기 구조식중 R은 수소, CO2R8이며 이때 R7은 수소, 탄소원자 1 내지 5개의 알킬, 각기 탄소원자 2 내지 6개의 알케닐 및 알키닐, 트리플루오로메틸, 벤질, 푸릴, 티에닐, 피리딜 또는 R9C6H4이며 이중 R9은 H, NH2, F, CI, Br, CH3또는 OCH3이고 R8는 탄소원자 1 내지 5개의 알킬 또는 R9C6H4이며 특히 바람직한 R7은 탄소원자 1 내지 5개의 알킬 및 트리플루오로메틸이다.
    R1은 수소, 벤질, 벤조일, 탄소원자 1 내지 5개의 알킬노일 또는 -CO-(CH2)P-NR2R3이고 이때 P는 0 또는 1 내지 4의 정수이고, R2및 R3는 각기 독립적으로 수소 또는 탄소원자 1 내지 4의 알킬이고, R2및 R3가 이들이 부탁되어 있는 질소와 함께 피페리디노, 피롤로, 피롤리디노, 모르폴리노 또는 알킬그룹이 탄소원자 1 내지 4인 N-알킬피페라지노중에서 선택되는 5- 또는 6-원 헤레로사이클환을 형성한다. 바람직한 R1은 수소 및 탄소원자 1 내지 6개의 알킬이다.
    R5는 수소, 메틸 또는 에틸이고 특히 바람직한 R5는 수소 및 메틸이다.
    R6는 수소, 알콕시그룹이 탄소원자 1 내지 4인 -(CH2)y- 카르알콕시이며, 이때 Y는 0 또는 1 내지 4의 정수, 카보벤질옥시, 포르밀, 탄소원자 2 내지 5개의 알카노일, 탄소원자 1 내지 6개의 알킬, -(CH2)Z-C6H5, 이때 X는 1 내지 4의 정수, 또는 COCCH2)X-1-C6H5이고, 특히 바람직한 R6는 수소 및 탄소원자 1 내지 6개의 알킬이다.
    Z는 (a) 탄소원자 1 내지 9의 알킬렌, (b) -(alk1)m-X-(al2)n-이때 (alk1)과 (alk2)는 각기 탄소원자 1 내지 9의 알릴켄이고 단, (alk1)과 (alk2) 중의 탄소원자의 합계가 9 이상은 아니며, m과 n은 각기 0 또는 1이고, X는 O, S, SO 및 SO2이며 특히 바람직한 X는 0이다.
    W는 수소, 메틸, 피리딜, 피페리딜,이때 W1은 수소, 플루오로 및 클로로로 구성되는 그룹중에서 선택됨 및이때 W2는 수소 또는이고 a는 1 내지 5의 정수이며 b는 0 또는 1 내지 5의 정수이고, 단, a와 b의 합은 5를 넘지 않으며 특히 바람직한 w는 수소 및 페닐이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019810002717A 1980-07-28 1981-07-27 9-아미노-1-하이드록 시옥타하이드로 벤조[c] 퀴놀린의 제조 방법 Expired KR850000273B1 (ko)

Applications Claiming Priority (2)

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US06/173,207 US4309545A (en) 1980-07-28 1980-07-28 Oximino-1-hydroxyoctahydrobenzo[c]quinolines and derivatives thereof
US173,207 1980-07-28

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KR830006217A true KR830006217A (ko) 1983-09-20
KR850000273B1 KR850000273B1 (ko) 1985-03-15

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US (1) US4309545A (ko)
EP (1) EP0045171B1 (ko)
JP (1) JPS57112372A (ko)
KR (1) KR850000273B1 (ko)
AR (1) AR230988A1 (ko)
AT (1) ATE11775T1 (ko)
AU (1) AU525944B2 (ko)
CA (1) CA1178274A (ko)
CS (1) CS228515B2 (ko)
DD (1) DD202012A5 (ko)
DE (1) DE3168891D1 (ko)
DK (1) DK334581A (ko)
EG (1) EG15535A (ko)
ES (1) ES504323A0 (ko)
FI (1) FI812338A7 (ko)
GR (1) GR75283B (ko)
GT (1) GT198170557A (ko)
HU (1) HU185133B (ko)
IE (1) IE51426B1 (ko)
IL (1) IL63423A0 (ko)
IN (1) IN158867B (ko)
NO (2) NO812557L (ko)
NZ (1) NZ197856A (ko)
PH (1) PH17281A (ko)
PL (1) PL133928B1 (ko)
PT (1) PT73440B (ko)
SU (1) SU1217254A3 (ko)
YU (1) YU185181A (ko)
ZA (1) ZA815128B (ko)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4920221A (en) * 1982-03-16 1990-04-24 Pfizer Inc. Substituted decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines
US4473704A (en) * 1982-03-16 1984-09-25 Pfizer Inc. Substituted dodecahydrotriphenylenes, decahydro-1H-cyclopenta[1]phenanthrenes, decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines as CNS agents
US4642373A (en) * 1982-03-16 1987-02-10 Pfizer Inc. Substituted dodecahydrotripheylenes, and decahydropyrrolo[1,2-f]phenanthridines as CNS agents
US5605906A (en) * 1995-03-24 1997-02-25 Merck Frosst Canada, Inc. Cannabinoid receptor agonists
EE03523B1 (et) * 1996-01-31 2001-10-15 Byk Gulden Lomberg Chemische Fabrik Gmbh Fenantridiinid, neid sisaldavad ravimid ja nende kasutamine
US6127378A (en) * 1996-03-26 2000-10-03 Byk Gulden Lomberg Chemische Fabrik Gmbh Phenanthridines substituted in the 6 position
ES2184077T3 (es) * 1996-03-26 2003-04-01 Altana Pharma Ag Nuevas fenantridinas sustituidas en la posicion 6.
US5776482A (en) * 1996-03-29 1998-07-07 University Of Iowa Research Foundation Tetrahydroquinoline analogues for use in glaucoma treatment
IL133825A (en) * 1997-07-25 2005-12-18 Altana Pharma Ag Substituted 6-phenylphenanthridines, medicaments containing same and use thereof in the production of medicaments
JP2001510826A (ja) * 1997-07-25 2001-08-07 ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング 置換６−アルキルフェナントリジン
US6566560B2 (en) 1999-03-22 2003-05-20 Immugen Pharmaceuticals, Inc. Resorcinolic compounds
JP2002539246A (ja) 1999-03-22 2002-11-19 イミュジェン ファーマシューティカルズ インコーポレイティッド 免疫疾患の治療
US20060084021A1 (en) * 2004-09-10 2006-04-20 Kubicek Chris A Wick holder
AU2002213429A1 (en) * 2000-09-28 2002-04-08 Immugen Pharmaceuticals, Inc. Antiviral methods and compounds
WO2002026224A2 (en) * 2000-09-28 2002-04-04 Immugen Pharmaceuticals, Inc. Methods and compounds for inhibiting eicosanoid metabolism and platelet aggregation
AU2003214226A1 (en) * 2002-03-18 2003-10-08 Immugen Pharmaceuticals, Inc. Topical formulations of resorcinols and cannibinoids and methods of use
NZ551379A (en) * 2004-05-25 2010-11-26 Othera Holding Inc Oculoselective drugs and prodrugs

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839441A (en) * 1969-10-27 1974-10-01 Hoffmann La Roche Intermediates for partially hydrogenated phenanthridines
US3878219A (en) * 1973-07-13 1975-04-15 Abbott Lab 5H-{8 1{9 benzopyrano{8 3,4-d{9 pyridines
US3928598A (en) * 1973-11-05 1975-12-23 Lilly Co Eli Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug
US4087545A (en) * 1976-02-17 1978-05-02 Eli Lilly And Company Hexahydro-dibenzo[b,d]pyran-9-ones as antiemetic drugs
SE7704749L (sv) * 1976-05-17 1977-12-05 Pfizer Kinoliner och forfarande och mellanprodukter for framstellning derav
BE854655A (fr) 1976-05-17 1977-11-16 Pfizer 9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
US4152450A (en) * 1978-02-17 1979-05-01 Eli Lilly And Company 9-Amino-dibenzopyrans

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AU7343481A (en) 1982-05-06
YU185181A (en) 1983-12-31
IE51426B1 (en) 1986-12-24
SU1217254A3 (ru) 1986-03-07
IN158867B (ko) 1987-02-07
PL232331A1 (en) 1983-09-26
PT73440A (en) 1981-08-01
IE811686L (en) 1982-01-28
IL63423A0 (en) 1981-10-30
DE3168891D1 (en) 1985-03-28
GR75283B (ko) 1984-07-13
ATE11775T1 (de) 1985-02-15
AR230988A1 (es) 1984-08-31
EP0045171A2 (en) 1982-02-03
FI812338L (fi) 1982-01-29
EG15535A (en) 1986-09-30
DD202012A5 (de) 1983-08-24
AU525944B2 (en) 1982-12-09
NO812557L (no) 1982-01-29
KR850000273B1 (ko) 1985-03-15
PH17281A (en) 1984-07-06
CA1178274A (en) 1984-11-20
FI812338A7 (fi) 1982-01-29
US4309545A (en) 1982-01-05
HU185133B (en) 1984-12-28
EP0045171B1 (en) 1985-02-13
CS228515B2 (en) 1984-05-14
DK334581A (da) 1982-01-29
GT198170557A (es) 1983-01-12
NO854454L (no) 1985-01-29
ES8301926A1 (es) 1982-12-16
ES504323A0 (es) 1982-12-16
NZ197856A (en) 1984-10-19
EP0045171A3 (en) 1982-04-28
ZA815128B (en) 1982-07-28
PL133928B1 (en) 1985-07-31
PT73440B (en) 1983-06-20
JPS57112372A (en) 1982-07-13

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