KR940003922A - 9-아미노-6-데메틸-6-데옥시테트라시클린 광산 염의 제조방법 - Google Patents

9-아미노-6-데메틸-6-데옥시테트라시클린 광산 염의 제조방법 Download PDF

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KR940003922A
KR940003922A KR1019930015642A KR930015642A KR940003922A KR 940003922 A KR940003922 A KR 940003922A KR 1019930015642 A KR1019930015642 A KR 1019930015642A KR 930015642 A KR930015642 A KR 930015642A KR 940003922 A KR940003922 A KR 940003922A
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demethyl
deoxytetracycline
acid salt
mineral acid
halogen
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KR1019930015642A
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KR100280971B1 (ko
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숨 파이크-엥
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알퐁스 아아르 노예
아메리칸 사이아나밋드 캄파니
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Paper (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Peptides Or Proteins (AREA)

Abstract

본 발명은 테트라시클린 합성을 위해 가치있는 중간체인, 이후에 9-아미노-6-데메틸-6-데옥시테트라시클린으로 불리는 [4S-(4알파, 12a 알파)]-9-아미노-4-(디메틸아미노)-1,4,4a,5,5a,6,11,12a-옥타히드로-3,10,12,12a-테트라히드록시-1,11-디옥소-2-나프타센카르복사미드의 새로운 제조 방법에 관한 것이다.

Description

9-아미노-6-데메틸-6-데옥시테트라시클린 광산 염의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기식 (a)-(c)로 구성되는, 9-아미노-6-데메틸-6-데옥시테트라시클린 광산 염 제조방법: (a) 0℃내지 약 20℃온도에서, 차가운 농축 광산에서 6-데메틸-6-데옥시테트라시클린을 할로겐화제와 반응시키고 7-할로겐-6-데메틸-6-데옥시테트라시클린 광산염을 회수하고; (b)-15℃ 내지 +15℃의 온도 범위에서, 차가운 농축 광산에서 7-할로겐-6-데메틸-6-데옥시테트라시클린 광산염을 약간 몰 과량의 질화 시약과 반응시키고 7-할로겐-9-니트로-6-데메틸-6-데옥시테트라시클린 광산염을 회수하고; (c) 실온에서, 용매에서 7-할로겐-9-니트로-6-데메틸-6-데옥시트트라시클린 광산염을 1 내지 40psi에서 Ⅷ족 금속 촉매, 그들의 염 또는 귀금속 산화물로써 환원시키고, 알콜에서 희석하여 생성물을 분리하고 9-아미노-6-데메틸-6-데옥시테트라시클린 광산염을 회수한다.
  2. 하기 a)-b)로 구성되는 9-아미노-6-데메틸-6-데옥시테트라시클린 광산염의 제조방법: (a) 0℃ 내지 20℃온도에서, 차가운 농축 광산에서 6-데메틸-6-데옥시테트라시클린을 할로겐화제와 반응시키고 이어서 -15℃내지 +15℃의 온도에서 약간 몰 과량의 고체 금속 질산염 또는 "혼산"을 첨가하고, 용매로써 희석하고 7-할로겐-9-니트로-6-데메틸-6-데옥시트트라시클린 광산염을 회수하고, (b) 실온에서 용매에서 7-할로겐-9-니트로-6-데메틸-6-데옥시테트라시클린 광산염을 1 내지 40psi에서 Ⅷ족 금속 촉매, 그들의 염 또는 귀금속 산화물로써 환원시키고, 알콜로써 생성물을 분리하고 9-아미노-6-데메틸-6-데옥시테트라시클린 광산염을 회수한다.
  3. 제1 또는 2항에 있어서, 상기 할로겐화제가 브롬, N-클로로숙신이미드, N-브로모숙실이미드 일염화요오드 또는 벤질트리메틸암모늄 디클로로요오데이트를 포함하는 방법.
  4. 제1 또는 2항에 있어서, 상기 농축 광산이 농축 황산을 포함하는 방법.
  5. 제1 또는 2항에 있어서, 상기 7-할로겐-6-데메틸-6-데옥시테트라시클린 광산염, 7-할로겐-9-니트로-6-데메틸-6-데옥시테트라시클린 광산염 또는 9-아미노-6-데메틸-6-데옥시테트라시클린 광산염을 여과에 의해 회수하는 방법.
  6. 제1항에 있어서, 상기 질화 시약은 "혼산" 또는 금속 질산염을 포함하는 방법.
  7. 제6항에 있어서, 상기 "혼산"이 농축 황산내 10%질산 1.1 내지 1.2당량을 포함하는 방법.
  8. 제1 또는 2항에 있어서, 상기 Ⅷ족 금속 촉매, 그들의 염 또는 회토 산화물이 10-30중량%의 활성탄 상Pt, 활성탄상 Pd, 활성탄상 로듐, 활성탄 상 루테늄 또는 활성탕 상 이리듐을 포함하는 방법.
  9. 제2항에 있어서, 상기 금속 질산염은 10% 몰과량의 질산 칼륨을 포함하는 방법.
  10. 제2항에 있어서, 상기 "혼산"이 농축 황산내 10% 질산 1.1 내지 1.2당량을 포함하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930015642A 1992-08-13 1993-08-12 9-아미노-6-데메틸-6-데옥시테트라시클린 무기산염의 제조 방법 KR100280971B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7/928,587 1992-08-13
US07/928,587 US5248797A (en) 1992-08-13 1992-08-13 Method for the production of 9-amino-6-demethyl-6-deoxytetracycline

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KR940003922A true KR940003922A (ko) 1994-03-14
KR100280971B1 KR100280971B1 (ko) 2001-02-01

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US (1) US5248797A (ko)
EP (1) EP0582791B1 (ko)
JP (1) JP3686685B2 (ko)
KR (1) KR100280971B1 (ko)
CN (1) CN1037905C (ko)
AT (1) ATE152096T1 (ko)
AU (1) AU660834B2 (ko)
CA (1) CA2103839C (ko)
CZ (1) CZ286004B6 (ko)
DE (1) DE69310048T2 (ko)
DK (1) DK0582791T3 (ko)
ES (1) ES2101159T3 (ko)
FI (1) FI112939B (ko)
GR (1) GR3024076T3 (ko)
HU (1) HU212648B (ko)
IL (1) IL106675A (ko)
MX (1) MX9304648A (ko)
NO (1) NO301823B1 (ko)
NZ (1) NZ248355A (ko)
PH (1) PH30009A (ko)
PL (1) PL173730B1 (ko)
RU (1) RU2124000C1 (ko)
SK (1) SK279462B6 (ko)
TW (1) TW221412B (ko)
ZA (1) ZA935895B (ko)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5494903A (en) * 1991-10-04 1996-02-27 American Cyanamid Company 7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
US5442059A (en) * 1992-08-13 1995-08-15 American Cyanamid Company 9-[(substituted glycyl)amido)]-6-demethyl-6-deoxytetracyclines
EP1251550B1 (en) 1994-04-18 2005-03-30 Micron Technology, Inc. Method and apparatus for automatically positioning electronic die within component packages
US5675030A (en) * 1994-11-16 1997-10-07 American Cyanamid Company Method for selective extracting a 7-(hydrogen or substituted amino)-9- (substituted glycyl) amido!-6-demethyl-6-deoxytetracycline compound
US5843925A (en) * 1994-12-13 1998-12-01 American Cyanamid Company Methods for inhibiting angiogenesis, proliferation of endothelial or tumor cells and tumor growth
US5574026A (en) * 1994-12-13 1996-11-12 American Cyanamid Company Methods for inhibiting angiogenesis proliferation of endothelial or tumor cells and tumor growth
US5567693A (en) * 1994-12-13 1996-10-22 American Cyanamid Company Method for inhibiting angiogenesis, proliferation of endothelial or tumor cells and tumor growth
US5563130A (en) * 1994-12-13 1996-10-08 American Cyanamid Company Methods for inhibiting angiogenesis, proliferation of endothelial or tumor cells and tumor growth
US6072236A (en) * 1996-03-07 2000-06-06 Micron Technology, Inc. Micromachined chip scale package
CN1074460C (zh) * 1999-05-26 2001-11-07 贾晓峰 四环素发酵方法
US8106225B2 (en) * 1999-09-14 2012-01-31 Trustees Of Tufts College Methods of preparing substituted tetracyclines with transition metal-based chemistries
DE60027465T2 (de) * 1999-09-14 2007-02-01 The Trustees Of Tufts College, Medford Verfahren zur herstellung von substituierten tetracyclinen mit hilfe von auf übergangsmetalle basierten chemien
IL151971A0 (en) * 2000-03-31 2003-04-10 Tufts College 7-and 9-carbamate, urea, thiourea, thiocarbabamate, and heteroaryl-amino substituted tetracycline compounds
US20020132798A1 (en) 2000-06-16 2002-09-19 Nelson Mark L. 7-phenyl-substituted tetracycline compounds
US20020128238A1 (en) * 2000-06-16 2002-09-12 Nelson Mark L. 7-phenyl-substituted tetracycline compounds
US7094806B2 (en) 2000-07-07 2006-08-22 Trustees Of Tufts College 7, 8 and 9-substituted tetracycline compounds
CN1450989A (zh) * 2000-07-07 2003-10-22 塔夫茨大学信托人 7－取代的四环素化合物
SI1301467T1 (sl) 2000-07-07 2007-02-28 Tufts College 9-substituirane minociklinske spojine
US7553828B2 (en) * 2001-03-13 2009-06-30 Paratek Pharmaceuticals, Inc. 9-aminomethyl substituted minocycline compounds
EP1241160A1 (en) * 2001-03-13 2002-09-18 Glaxo Group Limited Tetracycline derivatives and their use as antibiotic agents
DE60135387D1 (de) 2001-03-13 2008-09-25 Paratek Pharm Innc 7,9 substituierte tetracyclinverbindungen
US20030181371A1 (en) * 2001-12-28 2003-09-25 Angiotech Pharmaceuticals, Inc. Compositions and methods of using collajolie
CN102531948A (zh) * 2002-03-08 2012-07-04 帕拉特克药品公司 氨基-甲基取代的四环素类化合物
AU2003218243B2 (en) 2002-03-21 2010-04-01 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
US20060287283A1 (en) * 2003-07-09 2006-12-21 Paratek Pharmaceuticals, Inc. Prodrugs of 9-aminomethyl tetracycline compounds
EP2298322A3 (en) 2003-07-09 2011-05-11 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
EP2284156A3 (en) 2004-10-25 2011-09-21 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
US8088755B2 (en) 2005-02-04 2012-01-03 Paratek Pharmaceuticals, Inc. 11a, 12-derivatives of tetracycline compounds
AR057034A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Metodos para purificar tigeciclina
AR057324A1 (es) * 2005-05-27 2007-11-28 Wyeth Corp Tigeciclina y metodos para preparar 9-aminominociclina
AR057033A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Tigeciclina y metodos para preparar 9-nitrominociclina
AR057032A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Tigeciclina y metodos de preparacion
US20070244335A1 (en) * 2006-04-17 2007-10-18 Teva Pharmaceutical Industries Ltd. Isolation of tetracycline derivatives
ES2528202T3 (es) * 2006-04-24 2015-02-05 Teva Pharmaceutical Industries Ltd. Una forma cristalina de tigeciclina y procesos para su preparación
WO2008066908A1 (en) * 2006-11-30 2008-06-05 Teva Pharmaceutical Industries Ltd. Processes for preparation of 9-haloacetamidominocyclines
WO2008106234A1 (en) * 2007-03-01 2008-09-04 Teva Pharmaceutical Industries Ltd. Processes for purification of tigecycline
JP2012520305A (ja) * 2009-03-12 2012-09-06 ワイス・エルエルシー テトラサイクリンのニトロ化

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE26271E (en) * 1967-09-26 Reductive alkylation process
US3036129A (en) * 1959-10-09 1962-05-22 American Cyanamid Co Preparation of 7-halo-6-deoxy-tetracyclines
US3043875A (en) * 1959-10-22 1962-07-10 Pfizer & Co C Halogenated tetracycline derivatives and processes for their preparation
US3338963A (en) * 1960-10-28 1967-08-29 American Cyanamid Co Tetracycline compounds
USRE26253E (en) * 1963-05-17 1967-08-15 And z-alkylamino-g-deoxytetracycline
US3423457A (en) * 1966-11-29 1969-01-21 American Cyanamid Co Substitution products of 7-chloro-6-demethyltetracycline
US5284963A (en) * 1992-08-13 1994-02-08 American Cyanamid Company Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines
SG47520A1 (en) * 1992-08-13 1998-04-17 American Cyanamid Co New method for the production of 9-amino-6-demethyl-6-deoxytetracycline

Also Published As

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MX9304648A (es) 1994-02-28
HU212648B (en) 1996-09-30
NO301823B1 (no) 1997-12-15
NO932868L (no) 1994-02-14
ATE152096T1 (de) 1997-05-15
KR100280971B1 (ko) 2001-02-01
CZ158393A3 (en) 1994-03-16
PL300065A1 (en) 1994-02-21
TW221412B (ko) 1994-03-01
NO932868D0 (no) 1993-08-12
SK279462B6 (sk) 1998-11-04
AU4460293A (en) 1994-02-17
CA2103839A1 (en) 1994-02-14
AU660834B2 (en) 1995-07-06
HUT65117A (en) 1994-04-28
FI112939B (fi) 2004-02-13
DE69310048D1 (de) 1997-05-28
JPH06199757A (ja) 1994-07-19
PH30009A (en) 1996-10-29
CZ286004B6 (cs) 1999-12-15
HU9302334D0 (en) 1993-11-29
ES2101159T3 (es) 1997-07-01
DE69310048T2 (de) 1997-07-31
FI933563A (fi) 1994-02-14
CA2103839C (en) 2004-10-05
EP0582791B1 (en) 1997-04-23
EP0582791A1 (en) 1994-02-16
IL106675A (en) 1998-09-24
JP3686685B2 (ja) 2005-08-24
CN1083046A (zh) 1994-03-02
SK85193A3 (en) 1994-05-11
DK0582791T3 (da) 1997-05-20
IL106675A0 (en) 1993-12-08
ZA935895B (en) 1994-03-09
PL173730B1 (pl) 1998-04-30
US5248797A (en) 1993-09-28
FI933563A0 (fi) 1993-08-12
NZ248355A (en) 1995-12-21
GR3024076T3 (en) 1997-10-31
RU2124000C1 (ru) 1998-12-27
CN1037905C (zh) 1998-04-01

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