US2006173172A1PendingUtilityA1
Method for producing novel spinosyn derivatives
Est. expiryJul 20, 2021(expired)· nominal 20-yr term from priority
C07D 313/00C07H 17/08C12P 19/62C12P 17/181
54
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Claims
Abstract
The present invention relates to methods for producing novel spinosyn derivatives which are substituted with a 1-hydroxy-ethyl radical in the C-21 position and to novel spinosyn derivatives of this type per se and to their use for producing novel spinosyns.
Claims
exact text as granted — not AI-modified1 . A method for producing compounds of the general formula (I),
in which
A-B is any of the following groups: —HC═CH—, —HC═C(CH 3 )—, —H 2 C—CH 2 — or —H 2 C—CH(CH 3 )—,
D is the group
R 1 is hydrogen or an amino sugar and
R 2 is hydrogen or a su gar,
characterized in that compounds of the general formula (II),
in which
A-B, D and R 1 are as defined above,
are contacted with a microorganism in an aqueous nutrient medium under aerobic conditions or with an enzyme extract prepared therefrom or with one or more enzymes isolated therefrom.
2 . The method as claimed in claim 1 , characterized in that compounds of the general formula (II) are used,
in which formula, in the case (1) that
A-B is any of the following groups: —HC═CH—, —HC═C(CH 3 )—, —H 2 C—CH 2 — or —H 2 C—CH(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a
and
R 2 is a sugar of the formula 2a
or in which, in the case (2) that
A-B is the group —HC═CH— or —H 2 C—CH 2 — and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is hydrogen or a sugar of the formula 2b, 2c, 2d, 2e or 2f
or in which, in the case (3) that
A-B is any of the following groups: —HC═CH—, —HC═C(CH 3 )— or —H 2 C—CH 2 — and
D is as defined above,
R 1 is hydrogen or an amino sugar of the formula 1b
and
R 2 is hydrogen or a sugar of the abovementioned formula 2a
or in which, in the case (4) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2g, 2h, 2i, 2j or 2k
or in which, in the case (5) that
A-B is the group —HC═CH— or —H 2 C—CH 2 — and
D is as defined above;
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2l or 2m.
or in which, in the case (6) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is as defined above,
R 1 is hydrogen or an amino sugar of the abovementioned formula 1b or an amino sugar of the formula 1c
and
R 2 is a sugar of the abovementioned formula 2b, 2c, 2g or 2h or a sugar of the formula 2n
or in which, in the case (7) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2o
or in which, in the case (8) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the abovementioned 1b and
R 2 is a sugar of the abovementioned formula 2d, 2i or 2j or a sugar of the formula 2p
in which, in the case (9) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is hydrogen or an amino sugar of the abovementioned formula 1c and
R 2 is a sugar of the abovementioned formula 2i or 2p
or in which, in the case (10) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the formula 1d, 1e or 1f
and
R 2 is a sugar of the abovementioned formula 2a
or in which, in the case (11) that
A-B is the group —HC═CH— and
D is the group
R 1 is hydrogen or an amino sugar of the abovementioned formula 1a.
3 . The method as claimed in claim 1 or 2 , characterized in that compounds of the general formula (II) are used,
in which formula, in the case (12) that A-B is the group —HC═CH— or —HC═C(CH 3 )— and D is the group R 1 is an amino sugar of the formula 1a and R 2 is a sugar of the formula 2a, 2g or 2h or in which, in the case (13) that A-B is the group —HC═CH— and D is as defined above, R 1 is an amino sugar of the formula 1a and R 2 is hydrogen or a sugar of the formula 2d, 2e, 2l, 2m or 2o or in which, in the case (14) that A-B is the group —HC═CH— or —HC═C(CH 3 )— and D is as defined above, R 1 is hydrogen or an amino sugar of the formula 1b and R 2 is hydrogen or a sugar of the formula 2a or in which A-B, D and R 1 are as defined as in the case (11).
4 . The method as claimed in any of claims 1 to 3 , characterized in that compounds of the general formula (II) are used,
in which formula, in the case (15) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a and
R 2 is a sugar of the formula 2a
or in which, in the case (16) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the formula 1a and
R 2 is hydrogen or a sugar of the formula 2d, 2l or 2m
or in which A-B, D and R 1 are as defined in the case (11).
5 . The method as claimed in any of claims 1 to 4 , characterized in that compounds of the general formula (II) are used,
in which formula in the case (17) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a and
R 2 is a sugar of the formula 2a
or in which, in the case (18) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is hydrogen and
R 2 is hydrogen.
6 . The method as claimed in any of claims 1 to 5 characterized in that the microorganism used is a microorganisms from the group of actinomycetes.
7 . The method as claimed in claim 6 , characterized in that the microorganism used from the group of actinomycetes is a microorganism of the genus Streptomyces.
8 . The method as claimed in claim 7 , characterized in that the microorganism used of the genus Streptomyces is a strain of the species Streptomyces djakartensis, Streptomyces griseofuscus, Streptomyces caelestis, Streptomyces antibioticus, Streptomyces griseus or Streptomyces aureofaciens.
9 . The method as claimed in claim 8 , characterized in that the strain has the characteristic features of the strains Streptomyces djakartensis DSM 14327, Streptomyces griseofuscus DSM 14330, Streptomyces caelestis DSM 14328, Streptomyces antibioticus DSM 14329, Streptomyces griseus DSM 14331 or Streptomyces aureofaciens DSM 14332.
10 . The method as claimed in any of claims 1 to 9 , characterized in that the compounds of the general formula (I) are isolated.
11 . A compound of the general formula (I),
in which
A-B is any of the following groups: —HC═CH—, —HC═C(CH 3 )—, —H 2 C—CH 2 — or —H 2 C—CH(CH 3 )—,
D is the group
R 1 is an amino sugar and
R 2 is a sugar.
12 . The compound as claimed in claim 11 , characterized in that,
in the case (1) that
A-B is any of the following groups: —HC═CH—, —HC═C(CH 3 )—, —H 2 C—CH 2 — or —H 2 C—CH(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a
and
R 2 is a sugar of the formula 2a
or, in the case (2) that
A-B is the group —HC═CH— or —H 2 C—CH 2 — and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is hydrogen or a sugar of the formula 2b, 2c, 2d, 2e or 2f
or, in the case (3) that
A-B is one of the following groups: —HC═CH—, —HC═C(CH 3 )— or —H 2 C—CH 2 — and
D is as defined above,
R 1 is hydrogen or an amino sugar of the formula 1b
and
R 2 is hydrogen or a sugar of the abovementioned formula 2a
or, in the case (4) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2g, 2h, 2i, 2j or 2k
or, in the case (5) that
A-B is the group —HC═C—H— or —H 2 C—CH 2 — and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2l or 2m
or, in the case (6) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is as defined above,
R 1 is hydrogen or an amino sugar of the abovementioned formula 1b or an amino sugar of the formula 1c
and
R 2 is a sugar of the abovementioned formula 2b, 2c, 2g or 2h or a sugar of the formula 2n
or, in the case (7) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1a and
R 2 is a sugar of the formula 2o
or, in the case (8) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the abovementioned formula 1b and
R 2 is a sugar of the abovementioned formula 2d, 2i or 2j
or a sugar of the formula 2p
or, in the case (9) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is hydrogen or an amino sugar of the abovementioned formula 1c and
R 2 is a sugar of the abovementioned formula 2i or 2p
or, in the case (10) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is amino sugar of the abovementioned formula 1d, 1e or an amino sugar of the formula 1f
and
R 2 is a sugar of the abovementioned formula 2a
or, in the case (11) that
A-B is the group —HC═CH— and
D is the group
R 1 is hydrogen or an amino sugar of the abovementioned formula 1a.
13 . The compound as claimed in claim 12 , characterized in that,
in the case (12) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a and
R 2 is a sugar of the formula 2a, 2g or 2h
or, in the case (13) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the formula 1a and
R 2 is hydrogen or a sugar of the formula 2d, 2e, 2 1 , 2m or 2o
or, in the case (14) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is as defined above,
R 1 is hydrogen or an amino sugar of the formula 1b and
R 2 is hydrogen or a sugar of the formula 2a
or A-B, D and R 1 are as defined as in the case (11).
14 . The compound as claimed in claim 12 , characterized in that,
in the case (15) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a and
R 2 is a sugar of the formula 2a
or, in the case (16) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is an amino sugar of the formula 1a and
R 2 is hydrogen or a sugar of the formula 2d, 2l or 2m
or A-B, D and R 1 are as defined as in the case (11).
15 . The compound as claimed in claim 12 , characterized in that,
in the case (17) that
A-B is the group —HC═CH— or —HC═C(CH 3 )— and
D is the group
R 1 is an amino sugar of the formula 1a and
R 2 is a sugar of the formula 2a
or, in the case (18) that
A-B is the group —HC═CH— and
D is as defined above,
R 1 is hydrogen and
R 2 is hydrogen.
16 . The compound as claimed in claim 12 , characterized in that
A-B is the group —HC═CH—, D is the group R 1 is an amino sugar of the formula 1a and R 2 is a sugar of the formula 2a, or in which A-B is the group —HC═CH— or —HC═C(CH 3 )—, D is as defined above, R 1 is hydrogen and R 2 is a sugar of the formula 2a, or in which A-B is a group —HC═CH—, D is as defined above, R 1 is hydrogen and R 2 is hydrogen.
17 . The use of compounds as claimed in any of claims 11 to 16 for producing novel spinosyn derivatives.Cited by (0)
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