[go: up one dir, main page]

IL49104A - Antibiotic substances derived from antibiotic 67-694 and processes for their preparation - Google Patents

Antibiotic substances derived from antibiotic 67-694 and processes for their preparation

Info

Publication number
IL49104A
IL49104A IL49104A IL4910476A IL49104A IL 49104 A IL49104 A IL 49104A IL 49104 A IL49104 A IL 49104A IL 4910476 A IL4910476 A IL 4910476A IL 49104 A IL49104 A IL 49104A
Authority
IL
Israel
Prior art keywords
hydrogen
positions
carbon atoms
compound
compounds
Prior art date
Application number
IL49104A
Other languages
Hebrew (he)
Other versions
IL49104A0 (en
Original Assignee
Scherico Ltd
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
Priority claimed from US05/554,266 external-priority patent/US3975372A/en
Application filed by Scherico Ltd filed Critical Scherico Ltd
Publication of IL49104A0 publication Critical patent/IL49104A0/en
Publication of IL49104A publication Critical patent/IL49104A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08Hetero rings containing eight or more ring members, e.g. erythromycins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)

Claims (1)

1. July 2, 1979 2087X-Israel IK/cb^- 49104^ 1. Novel compounds of the general formula I and the non-toxic pharmaceutically acceptable acid addi¬ hydrogen, alkyl carbonyl having 2 to l8 carbon atoms or ben zoyl; R" is hydrogen or alkyl having 1 to 5 carbon atoms; B together with the carbon atoms of positions 12 end 13 to which i is attached represents a single bond or a double bond, or, when Q or Z is other than O, or when th macrolide ring is saturated between positions lO and 11 or unsaturated between positions 2 and 3, B may also be an oxirane ring; W is OR' or hydrogen, R ' being as pre viously defined, with the proviso that when positions 2 and 3 are connected by a double bond is hydrogen; and both Ds are either hydrogen or, when positions lo and 11 are connected by a single bond, both Ds can also be OR' R* - July 2, 19¾Q 2087X-Israel IK/cb 49104 with the further proviso that when in a compound B is a double bond, the carbon atoms of positions 10 and 11 are connected by a double bond, the carbon atoms of positions 2 and 3 are connected by a single bond, both Ds are hydrogen, Q is O, W is OR1, R and R' are as defined ^OR' above then Z is not ^ H . July 2, 19¾ „ 2087X-Israel IK/cb49.104-2 2. Compounds according to claim 1 wherein the dotted lines, Q, Z, R# R', R" and W are defined as in claim 1; B together with the carbon atoms of positions 12 and 13 to which it is attached represents a single bond or a double bond or, when Q or Z is other than O and the macrolide ring is saturated between positions lO and 11 and unsaturated between positions 2 and 3, B may also be an oxirane ring; and both Ds are either hydrogen or, when positions 10 and 11 are connected by a single bond and W is OR' both Ds can also be OH. 3. Compounds according to claim 1 or 2 wherein R* is hydrogen, or when in position 3 also acetyl or propionyl and when in positions 9 or 20 also acetyl. 4. Compounds according to anyone of claims 1 to 3 wherein ✓OH ^OR" R and R* are H and Z is O, \ H, \0R" , R" being alkyl, or NOH . 5. Compounds according to anyone of claims 1 to 4 wherein R" is hydrogen or methyl. 6. Compounds according to anyone of claims 1 to 5 wherein the dotted lines represent single bonds, Qf Z, R# R' and R" are as defined above, B together with the carbon atoms of positions 12 and 13 represents a single bond, W is OR' R' being as previously defined and both Ds are hydrogen. July 2^1979 2087X"Israel * IK/cb 4 9 1 04 - • OR" 7. Compounds according to claim 6 wherein Z is 0 or^Q^,, R" being alkyl having 1 to 5 carbon atoms. 8. Compounds according to claims 6 or 7 wherein R and R' are hydrogen. 9. Compounds according to anyone of claims 6 to 8 wherein R" is methyl. 10. Compound of claim 8 wherein Q is O and Z is O, the compound being 12 , 13-desepoxy-l0, 11- dihydrorosaramicin. 11. Compounds according to anyone of claims 1 to 5 wherein in formula I B together with the carbon atoms of positions 12 and 13 represents a double bond. 12. Compounds according to claim 11 wherein both Ds represent hydrogen and the positions 10 and 11 are connected by a double bond. 13. Compounds according to claim 12 wherein W is hydrogen and positions "2 and 3 are connected by a double bond. 14. Compounds according to claim 13 wherein Q and Z are Ό, especially 2,3; 12, 13-bisdehydro-3-deoxy-12 , 13-desepoxy-rosaramicin. 15. Compounds according to claim 11 or 12 wherein W is OR', R* being as defined above and positions 2 and 3 are connec¬ ted by a single bond. 16. Compounds according to claim 15 wherein Q is \OR', R* being as defined above. 17. Compound according to claim 16 being 9,9-dihydro-12,13-desepoxy-12 , 13- dehydrorosaramicift. 18. Compounds according to claim 15 wherein Q is O. ocH3 19. Compounds according to claim 18 wherein Z is \OCH3 or NOH. 20. Compounds according to claim 19 being 12, 13-desepoxy-12 13-dehydrorosaramicin20-dimethylacetal and 12, 13-desepoxy-12 13-dehydroi?osaramicin20-oxime. 21. Compounds according to claim 18 wherein Z is 0. 22. Compound according to claim 21 being 12 , 13-desepoxy-12, 13-dehydrorosaramicin . 23. Compound of claim 22 being in the trans-form. • IK/Cb 49164-2 24. Compounds according to anyone of claims 1 to 5 "wherei in formula I B together with the carbon atoms of position 12 and 13 represents an oxirane ring. 25. Compound according to claim 24 wherein W is hydrogen. 26. Compounds according to claim 25 wherein positions 2 and 3 as well as positions 10 and 11 are connected by a double bond. 27· Compounds according to claim 26 wherein Q and Z are 0. 28. Compound according to claim 27 being 2, 3-dehydro-3-deoxyrosaramicin. 29. Compounds according to claim 24 wherein W is OR'. 30. Compounds according to claim 29 wherein positions 10 and 11 are connected by a single bond and both Ds are hydrox . 31. Compounds according to claim 30 wherein Q and Z are O. 32. Compound according to claim 31 being 10, 11-dihydrcxy-10, 11-dihydrorosaramicin. July 2, 1979 2087X-Israel IK/ctu^_ 33· Compounds according to claim 29 wherein both Ds are hydrogen and positions 10 and 11 are connected by a single bond. 4. Compounds according to claim 33 wherein Q is 0. 35. Compound according to claim 31* being 10,11-dihydro-rosaramicin. 36. Compounds according to claim 33 wherein Q is 37. Compounds according to claim 29 wherein both Ds are hydrogen and positions 10 and 11 are connected by a double bond and Q is as defined in claim 1. ^OR' 38. Compounds according to claim 37 wherein Q is^ H. 39· Compound according to claim 38 being 9,9~dihydrorosa-ramicin 20-dimethylacetal. 40. Compounds according to claim 37 wherein Q is 0, Ml. Compound according to claim 40 being 20,20-dihydroros&'-ramicin. - 72 - July 2, 1979 2087X-Israel * IK/e 49104-2 42. Compound according to claim being rosaramicin 20- oxime. 43. Compound according to claim 40 being rosaramicin 20- dimethylacetal. 44. Compounds according to anyone of claim 4 to 43 wherein R' is alkylcarbonyl having 2 to 18 carbon atoms or benzoyl. 45. Compounds according to anyone of claims 4 to 43, where in R is alkylcarbonyl having 2 to 18 carbon atoms or benzoy 6. Compounds according to claim 44 or 4 , wherein R and/ or R' are alkylcarbonyl containing 2 to 5 carbon atoms or benzoyl. 47. Compounds according to claim or 46, wherein R is acetyl, propionyl, pi aloyl, stearoyl or benzoyl, 48. Compounds according to anyone of claims 1 to 7. in the form of their pharmaceutically acceptable acid addition salts. 49. Compounds according to claim 48 in the form of thejr stearate, lauryl sulfate or potassium dihydrogen phosphate salt. - 73 - July 2, 2087X-Israel IK/cb 4910 -2 50".- Process for the preparation of novel compounds of the general formula I as defined in anyone of claims 1 to £$, characterised in that the compounds are prepared by an appropriate process selected from the following processes (a) to (q): a: (for the preparation of compounds of. the. general formu , NOR ' or NOR"; R and R* - are hydrogen; R" is hydrogen or alkyl having 1 to 5 carbon atoms; W is OR' or hydro gen, R' being as previously defined, with the proviso that when positions 2 and 3 are connected by a double bond W is hydrogen) with the further proviso that when in a compound the carbon atoms of positions 2 and 3 are connected by a single bond, Q is O, W is OR', R and R' are as de-fined above, then Z is not <^ H > reduction of an appropriately substituted com- July 2, 197^. 2087X-Israel IK/Cb 49104 or a non-toxic" pharmaceutically acceptable acid addition represents a fa- is 0, or the grou R' are hydrogen , alkylcarbonyl having 2 to 18 carbon atoms orbenzoyl »R" is hydrogen or alkyl having 1 to 5 carbon atoms; W is OR1 or hydrogen, R1 being as previously defined, with the proviso that when positions 2 and 3 ar*e connected by a double bond W is hydrogen and with the further proviso that when in a compound the carbon atoms of positions 2 and > are connected by a single bond, Q is 0, W is OR', R and Rf are as /OR' defined above, then Z is not \ H ; b: (for the preparation of compounds of the general formula I wherein the dotted lines represent, facultative double /OR1 bonds; Q is 0, or\ H: Z is NOR' or NOR"; R and R1 are hydrogen alkylcarbonyl having 2 to 18 carbon atoms or benzoyl; R" is hydrogen or alkyl having 1 to 5 carbon atoms; B together with the carbon atoms of positions 32 and 15 40 J 0 -2 July 1979 2087X~Israel IK/cb R1 being as previously defined, with the proviso that whe positions 2 and J are connected by a double bond is hyd gen; and both 49104-2 July 2, 197^- 2087X-Israel IK/cb Ds are either hydrogen or, when positions 10 and 11 are connected by a single bond, both Ds can also be OR1, R1 being as previously defined) reacting a compound of the general formula I or an acid addition salt thereof, where the dotted lines, Q, B, W, R, R1 and D are as defined in this claim and Z is 0, with hydroxylamine or an appropria derivative thereof; c: (for the preparation of compounds of the general formula I double B together with the carbon atoms of positions 12 and 13 t which it is attached represents a single bond or a double bond or an oxirane ring; W is OR* or hydrogen, with the proviso that when positions 2 and are connected by a double bond W is hydrogen; and both Ds are either hydrogen or, when positions 10 and 11 are connected by a single bond, both Ds can also be OR1 , R' being hydrogen; with the exception of the compounds wherein B is a double bond, the carbon atoms of positions 10 and 11 are connected by a double bond; the carbon atoms of positions 2 and j5 are connected by a single bond, both Ds are hydrogen, Q is 0, W is OR1, R and R1 are as defined above) reduction of a compound of the general formula I, wherein the dotted lines, Q, B, W and D are as defined in this claim, R and R are hydrogen, alkylcarbonyl having 2 to 18 carbon, atoms or benzoyl and Z is 0; 04-D ' July 2, 1979 2087X-Israel IK/cb wherein the dotted line represents a facultative double /OR' SOR* SORU bond; Q is O, or \ H; Z is O, or the group H, \ORw# NOR' or NOR"; R and R' are hydrogen, alkylcarbonyl having 2 to 18 carbon atoms or benzoyl; R" is hydrogen or allyl having 1 to 5 carbon atoms; B together with the carbon atoms of positions 12 and 13 to which it is attached represents a single bond, a double bond or an oxirane ring; and both Ds are either hydrogen or, when positions 10 and 11 are connected by a single bond, both Ds can also be OR') elimination of the eliminable group T and a hydrogen in position 2 fro "a compound of the general formula VIII, 4 104 July 2, 1979 2087X-Israel IK/cb e: (for the preparation of compounds of the general formula IX, NOR* or NOR"; R and R' are hydrogen, alkylcarbonyl having 2 to 18 carbon atoms or benzoyl; R" is hydrogen or alk l havin 1 to 5 carbon atoms B together with the V July 2, 1979 2087X-Israel IK/cb represents a single bond or an oxirane ring; W is OR* or hydrogen, R* being as previously defined; and both Ds ar hydrogen) catalytic hydrogenation of an appropriately substituted compound of the general formula I, wherein Q, Z, R, R' , R" and D are as defined above in this claim; t dotted lines represent facultative double bonds; B togeth with the carbon atoms of positions 12 and 13 to which it attached represents a single bond, a double bond or an ox rane ring; is OR* or hydrogen, R* being as previously defined, with the proviso that when positions 2 and 3 are connected by a double bond W is hydrogen^ f: (for the preparation of compounds of the general formu I wherein the dotted lines represent facultative double /OR' /OR" bonds; Q is O, or \ H; Z is \OR"; R and ' are hydroge alkyl carbonyl having 2 to 18 carbon atoms or benzoyl; R" is alkyl having 1 to 5 carbon atoms; B together with the ca bon atoms of positions 12 and 13 to which it is attached represents a single bond, a double bond or an oxirane rin W is OR' or hydrogen, R' being as previously defined, wit the proviso that when positions 2 and 3 are connected by double bond is hydrogen; and both Ds are either hydroge or, when positions lO and 11 are connected by a single bond, both Ds can also be OR') treating a corresponding 2 aldehyde compound (i.e. a compound of formula I wherein t dotted lines, B, D, Q, R, R' axdW are defined as above in this paragraph and Z is O) with an alcohol containing 1 t July 1979 2087X-lsrael IK/cb donor g: (for the preparation of compounds of the general formula I, wherein the dotted lines represent facultative double ✓ OR* xOR' /OR" bonds; Q is ' \ H; Z is \ H, or \ OR" ; R aid R' are R" is alkyl having 1 to 5 carbon atoms; B together with the carbon atoms of positions 12 and 13 to which it is attached represents a single bond, a double bond or an oxirane ring; W is OR* or hydrogen, with the proviso that when positi ons 2 and 3 are connected by a double bond W is hydrogen; and both Ds are either hydrogen or, when positions 10 and 11 are connected by a single bond, both Ds can also be OR', R' being as previously defined) reduction of a compound of the general formula I, wherein the dotted lines, B D, R" and W are as defined above in this paragraph and S OR" Q is 0, Z is 0 or \ OR" , R and R' are hydrogen; alkyl- carbonyl having 2 to 18 carbon atoms or benzoyl, in position 9 and, provided Z is 0, in position 20; gen, alkylcarbonyl having 2 to 18 carbon atoms or benzoyl; B together with the carbon atoms of positions 12 and 13 to which it is attached represents a single bond or a double bond or, when Q is other than 0, or when the macrolide ring is saturated between positions 10 and 11 or unsaturated July ?, 1979 . 20&7X-Isroel IK/cb W XB, OR' or hydrogen, R' being as previously defined, with the proviso that when positions 2 and 3 are connected by a double bond is hydrogen; and both Ds are either hydrogen or, when positions lO and 11 are connected by a single bond, both Ds can also be OR', R' being as previously defined) hydrolysis of a compound of the general formula I, wherein the dotted lines, B, Q, R', W and D are as defined above in this claim, R is defined as R', Z is , R" being alkyl having 1 to 5 carbon atoms; i: (for the preparation of compounds of the general formula wherein the dotted line represents a facultative double /OR' /OR' /OR" bond; Q is 0, or H; Z is 0, or the group \ H, \0R" , NOR' or NOR"; R ' is hydrogen, alkylcarbonyl having 2 to 18 carbon atoms or benzoyl; R" is hydrogen or alkyl having 1 to 5 cairbcn atoms; is OR' or hydrogen, R' being July , lyyy 208yx- Israel IK/cb wherein the dotted line, Q^WjZ.R' and R" are as defined above in this claim and R is defined as R'; j: (for the preparation of compounds of general formula I differing from the definition in claim 1 in that therein Q is only defined as oxo group) oxidation of the group of position 9 of the corresponding compound of the said for- ^OR' mula I, wherein Q is^ H. k: (for the preparation of compounds of the general formula I differing from the definition in claim 1 in that therein Z is defined as oxo group only: W is OR' and R and R1 are not H) oxidation of the corresponding compound ^OH of the said formula I, wherein Z is^ H. 1: (for the preparation of compounds of the general formula I defined as in claim 1, wherein positions 10 and 11 are connected by a double bond) demesyloxylation of a July 2, 1979 20o7X-lsrael IK/cb corresponding compound, wherein positions 10 and 11 are connected by a single bond and a mesyloxy group is contained in positions 10 and 11; m: (for the preparation of compounds of the general formula I, defined in claim 1, wherein Z is an oxo group), deoxami--nation of the corresponding compound wherein Z is NOR' or NOR" ; n: (for the preparation of compounds of the general formula I defined in claim 1 wherein Z is 0) treatment of the corresponding compounds wherein Z is with a mercuric salt ; o: esteri ication of a compound of general formula I defined above containing at least one free OH^-group; p: solvol sis of a compound of the general formula I co ^ taining at least one estergroup; q: trans ormation of a compound of the general formula I in its free form or in the form of its ester into its acid addition salt. July ]y'V9 Λ : '; $ 2087X-lsrae3 IK/cb 51. Process according to claim 50(a), characterised in that the reduction is performed by means of alkali metal bromide or alkali metal iodide in an organic acid or in aromatic hydrocarbons containing concentrated hydroiodic acid. 52. Process according to claim 51, characterised in that potassium iodide in refluxing acetic acid is used. 53· Process according to claim 50 (a), characterised in that the reduction is performed by means of chromous ions in a preferably dilute mineral acid solution under an inert atmosphere. 51». Process according to claim 53, characterised in that the chromous ions are present in the range of from 2.0 to 2.2 moles per mole of starting compound. 55. Process according to claim 53 or 5^ characterised in that the pH of the reaction mixture is between 0,8 and 2, 56. Process according to anyone of claims 53 to 55 characterised in that rosaramicin is reduced at 25°C in 1 N sulfuric acid under argon with chromous ions derived from chromous chloride, the mole ratio of chromous chloride to rosaramicin being 2.2 to 1. 57· Process according to claim 50 (b) characterised in that IK/cb the reaction is performed by means of hydroxylamine or its hydrohalogenide , especially hydrochloride. 58. Process according to claim 50 (c) characterised in that the reaction is performed by means of lithium aluminium tri-t-butoxyhydride or tetrabutyl ammonium cyanoborohydride. 59. Process according to claim 50 (e) characterised in that the reaction is performed by means of palladium on charcoal as catalyst. 60. Process according to claim 50 (f) characterised in that the reaction is performed by means of difluoroacetic acid as catalyst. 61. Process according to claim 50 (g) characterised in that the reaction is performed by means of sodium borohydride, 62. A therapeutic composition haying antibiotic activity, comprising the compounds of the general formula I as defined in anyone of claims 1 to Ί9· · 63. A therapeutic composition having antibiotic activity comprising a compound as defined by anyone of claims 1 to ^9 as an active ingredient, in admixture with a suitable pharmaceutically · acceptable carrier or excipient. composition according to claim 62 or 63 in the form July 2, 197 4 9 1 0 -ft 2087X-Israel * IK/cb of a solid shaped dosage unit. 65 . The composition of claim 6¾ , wherein the dosage unit is a tablet, capsule or a container comprising an injection liquid. 66 . Process for preparing a therapeutical composition having antibiotic activity, characterised in that a compound of the general formula (I) defined as in anyone of claims 1 to JJ 9 is brought into a form suitable for therapeutical administration . 67 . A therapeutical composition having antibiotic activity, when prepared by the process of claim 66 . 68. Process for the preparation of compounds having the general formula (I), substantially as hereinbefore described, with particular reference to the examples. 69. Compounds having the general formula (I), when prepared by a process according to anyone of claims 50 to 61. 70. A method for eliciting an antibacterial effect which comprises administering to an animal a therapeutically effective quantity of a compound defined in anyone of claims 1 to and 68 .
IL49104A 1975-02-28 1976-02-25 Antibiotic substances derived from antibiotic 67-694 and processes for their preparation IL49104A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55425075A 1975-02-28 1975-02-28
US05/554,266 US3975372A (en) 1975-02-28 1975-02-28 Preparation of 12,13-desepoxy-12,13-dehydrorosamicin

Publications (2)

Publication Number Publication Date
IL49104A0 IL49104A0 (en) 1976-04-30
IL49104A true IL49104A (en) 1979-12-30

Family

ID=27070531

Family Applications (1)

Application Number Title Priority Date Filing Date
IL49104A IL49104A (en) 1975-02-28 1976-02-25 Antibiotic substances derived from antibiotic 67-694 and processes for their preparation

Country Status (20)

Country Link
JP (1) JPS51110585A (en)
AR (1) AR215851A1 (en)
AT (1) AT344321B (en)
AU (1) AU499566B2 (en)
CA (1) CA1075234A (en)
CH (1) CH630391A5 (en)
DD (1) DD125959A5 (en)
DE (1) DE2607459A1 (en)
DK (1) DK79876A (en)
ES (1) ES445489A1 (en)
FI (1) FI63421C (en)
FR (1) FR2302102A1 (en)
GB (1) GB1544819A (en)
HU (1) HU176333B (en)
IE (1) IE42957B1 (en)
IL (1) IL49104A (en)
LU (1) LU74420A1 (en)
NL (1) NL7601863A (en)
NO (1) NO141718C (en)
PT (1) PT64836B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4279896A (en) * 1980-06-23 1981-07-21 Schering Corporation Novel 20-imino macrolide antibacterial agents
JPS58219197A (en) * 1982-06-15 1983-12-20 Sanraku Inc Derivative of macrolide antibiotic
US4436729A (en) * 1982-06-30 1984-03-13 Schering Corporation 23-Demycinosyltylosin compounds, pharmaceutical compositions and method of use
US4454314A (en) * 1982-08-02 1984-06-12 Pfizer Inc. Antibacterial mycaminosyl tylonolide and related macrolide derivatives
SI8710674B (en) * 1987-04-14 1998-06-30 Pliva Process for preparation of 10,11,12,13-tetrahydro derivatives of tylosin
FR2626576B1 (en) * 1987-05-06 1991-07-12 Adir NOVEL CARBOMYCIN B DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
PT87417B (en) * 1987-05-06 1992-08-31 Adir PROCESS FOR THE PREPARATION OF NEW MACROLIDATE COMPOUNDS
US5195268A (en) * 1991-11-21 1993-03-23 Ellis Gregory T Weedless hook for lures
US5218778A (en) * 1992-05-28 1993-06-15 Szantor Alfons J Fishing lure

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR205976A1 (en) * 1972-11-15 1976-06-23 Scherico Ltd PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 3-MONOESTERS OF ROSAMYCIN THAT HAVE ANTIBACTERIAL ACTIVITY

Also Published As

Publication number Publication date
FR2302102B1 (en) 1978-12-01
ATA133376A (en) 1977-11-15
IE42957B1 (en) 1980-11-19
JPS51110585A (en) 1976-09-30
NL7601863A (en) 1976-08-31
LU74420A1 (en) 1977-01-07
NO760606L (en) 1976-08-31
HU176333B (en) 1981-01-28
FI63421C (en) 1983-06-10
IE42957L (en) 1976-08-28
FI63421B (en) 1983-02-28
DK79876A (en) 1976-08-29
NO141718C (en) 1980-04-30
NO141718B (en) 1980-01-21
DE2607459A1 (en) 1976-09-09
AU499566B2 (en) 1979-04-26
AU1141976A (en) 1977-09-01
AR215851A1 (en) 1979-11-15
DD125959A5 (en) 1977-06-08
FI760473A (en) 1976-08-29
FR2302102A1 (en) 1976-09-24
GB1544819A (en) 1979-04-25
AT344321B (en) 1978-07-10
CA1075234A (en) 1980-04-08
ES445489A1 (en) 1977-11-16
PT64836B (en) 1977-06-07
CH630391A5 (en) 1982-06-15
IL49104A0 (en) 1976-04-30
PT64836A (en) 1976-03-01

Similar Documents

Publication Publication Date Title
Casey et al. (Diphenylcarbene) pentacarbonyltungsten (0)
US4180567A (en) Iron preparations and methods of making and administering the same
Reiff et al. Stereospecific synthesis and reactions of optically active isopropyl methylphosphinate
CN111819182B (en) Synthesis of cantharidin
IL49104A (en) Antibiotic substances derived from antibiotic 67-694 and processes for their preparation
GB1199871A (en) Improvements in or relating to Sulfur-Containing Bisphenols
Hauck et al. The enantiomers of the valproic acid analogue 2-n-propyl-4-pentynoic acid (4-yn-VPA): asymmetric synthesis and highly stereoselective teratogenicity in mice
US3883580A (en) Asymmetric reduction of ketones to form optically active alcohols
Corey et al. Synthetic entry into the prostaglandin C series
AU649130B2 (en) Pharmaceutical compositions for transcutaneous administration
US3341593A (en) 1-p-hydroxyphenyl-2-(beta-3&#39;, 5&#39;-dihydroxyphenyl-beta-hydroxy)-ethylamino-propanes
GB1458744A (en) Process for producing a 6-deoxytetracylines
GB1373239A (en) N-substituted-2-carboxy-1-azacyclic compounds
US2830087A (en) beta-hydroxybutyric acid para-phenetidide and a process for preparing it
US3153042A (en) Morphinone and codeinone derivatives
Klein et al. The stereochemistry and rate of reduction of substituted cylohexanones with diborane
US3681323A (en) 6,9-oxygen bridged erythromycin derivatives
EP0060523B1 (en) Process for removing hydroperoxides and aldehydes from allyl-alkyl ether
IL43008A (en) Dibenzazecines and processes for the production thereof
GB1433472A (en) Biphenylyl ethers and their preparation
GB901209A (en) 6-deoxytetracyclines and compositions containing same
US3406237A (en) Composition and a method for relieving broncho-spasms which use 1-p-hydroxyphenyl - 2 - (beta - 3&#39;,5&#39; - dihydroxyphenyl - beta-hydroxy)-ethylaminopropane
US3194821A (en) 17alpha-substituted 17beta-hydroxyestrenes
US3076826A (en) 17 alpha-(lower-alkyl)-19-nor-5(10)-androstene-3, 17beta-diols
US4518805A (en) Process for removing hydroperoxides and aldehydes from allyl-alkyl ether