GB1314104A - Syntheses of tetracyclines - Google Patents

Syntheses of tetracyclines

Info

Publication number
GB1314104A
GB1314104A GB2785370A GB2785370A GB1314104A GB 1314104 A GB1314104 A GB 1314104A GB 2785370 A GB2785370 A GB 2785370A GB 2785370 A GB2785370 A GB 2785370A GB 1314104 A GB1314104 A GB 1314104A
Authority
GB
United Kingdom
Prior art keywords
trimethyl
dioxin
tetrahydro
naphtho
oxo
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.)
Expired
Application number
GB2785370A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Research Corp
Original Assignee
Research Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Research Corp filed Critical Research Corp
Publication of GB1314104A publication Critical patent/GB1314104A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1314104 Tetracyclines; antibiotics RESEARCH CORP 9 June 1970 [12 June 1969] 27853/70 Headings C2A and C2C The invention comprises the stereospecific 12(a) hydrosylation of 12(a) deoxytetracyclines by contacting 12(a) deoxytetracycline precursors having a nucleus selected from with molecular oxygen while the said precursors are dissolved in solvents which are inert to the tetracycline structure in the presence of strong bases which are capable of ionizing the hydroxy groups of the tetracycline structure without destroying said structure. The following intermediates are prepared:- 7 - acetoxy - 4 - formyl - 4a,5,6,10b - tetrahydro - 2,2,10b - trimethyl - 6 - oxo - 4H - naphtho - [1,2 - d] - m - dioxin - 5 - acetaldehyde, 7 - acetoxy - 5 - formyl - 3a,4,10b,10c - tetrahydro - 2,2,10b - trimethyl - 6 - oxo - 6H - benz- [5,6]indeno[1,7 - de] - m - dioxin and its ozonide, 7 - acetoxy - 4 - formyl - 4a,5,610b - tetrahydro - 2,2,10b - trimethyl - 6 - ozo - 4H - naphtho[1,2 - d] - m - dioxin (2 - isomers), 7 - hydroxy - 4a,5,6,10b - tetrahydro - 2,2,10b - trimethyl - 6 - oxo - 4 - piperidinomethylene - 4H- naphtho[1,2-d]-m-dioxin and the methoxymethyl ether thereof, the methoxymethyl ether of 4 - formyl - 7 - hydroxy - 4a,5,6,10b - tetrahydro - 2,2,10b -trimethyl - 6 - oxo - 4H - naphtho[1,2-d]-m-dioxin, 4-(4a,5,6,10b -tetrahydro- 6 - methoxymethoxy - 2,2,10b - trimethyl - 6- oxo - 4H - naphtho[1,2-d] - m - dioxin - 4 - yl)- methylene - 2 - phenyl - 2 - thiazolin - 5 - one, 3a,3b,4,7,8a,9,13b,13c - octahydro - 5,8,10 - trihydroxy - 2,2,13b - trimethyl - 7,9 - dioxo - 4- thiobenzoylamino - naphthaceno[5,6 - de] - mdioxin-6-carboxamide and its methoxymethyl ether, methy 3-oxoglutaramate, and an enamine having the formula The following tetracyclines are prepared by the above process:- 1,4,4a,5,5a,6,11,12a - Octahydro - 5,6,10,11,- 12a - hexahydroxy - 6 - methyl - 1,11 - dioxo - 4- thiobenzylamino- 2 - naphthacenecarboxamide, (which may be converted via 4-dedimethylamino-5-oxytetracycline to 4-dimethylamino- 1,4,4a,5,5a,6,11,12a - octahydro - 3 - 5,6,10,12,- 12a - hexahydroxy -6 - methyl - 1,11- dioxo - 2- naphthacenecarboxamide), 4-benzamido-N-tert.- butyl - 7 - chloro - 1,4,4a,5,5a,6,11,11a,12,12adecahydro - 3,12a - dihydroxy - 10 - methoxy- 1,11,12 - trioxo - 2 - naphthacenecarboxamide, (2-isomeric forms), and 4-benzamido-N-tert.- butyl - 7 - chloro - 1,4,4a,5,5a,6,11,12a - octahydro - 3,12 - dihydroxy - 10 - methoxy - 1,11- dioxo-2-naphthacenecarboxamide.
GB2785370A 1969-06-12 1970-06-09 Syntheses of tetracyclines Expired GB1314104A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US83268069A 1969-06-12 1969-06-12

Publications (1)

Publication Number Publication Date
GB1314104A true GB1314104A (en) 1973-04-18

Family

ID=25262341

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2785370A Expired GB1314104A (en) 1969-06-12 1970-06-09 Syntheses of tetracyclines

Country Status (9)

Country Link
BE (1) BE751829A (en)
CA (1) CA922312A (en)
DE (1) DE2028717A1 (en)
ES (1) ES380658A1 (en)
FR (1) FR2052958A1 (en)
GB (1) GB1314104A (en)
LU (1) LU61117A1 (en)
NL (1) NL7008574A (en)
ZA (1) ZA704005B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2301916A3 (en) * 2004-10-25 2011-09-28 Paratek Pharmaceuticals, Inc. 4-aminotetracyclines and methods of use thereof

Also Published As

Publication number Publication date
NL7008574A (en) 1970-12-15
CA922312A (en) 1973-03-06
FR2052958A1 (en) 1971-04-16
LU61117A1 (en) 1970-08-20
BE751829A (en) 1970-11-16
ZA704005B (en) 1971-03-31
DE2028717A1 (en) 1971-01-28
ES380658A1 (en) 1972-10-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees