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EP0154445A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Analogues of antibiotic cc-1065

Assignee: Pharmacia and Upjohn Co
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Filing: 1985-02-20
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Granted: —
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Expires: 2005-02-20
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Abstract

Abstract Compounds of the formulae wherein R 1 is CH 3 or substituted CH 2 ; R 2 , R' 2 and R 3 are each H, C 1-5 alkyl or phenyl; X is halogen or substituted sulfonyloxy; R 5 is acyl; and R 50 is H or acyl. The compounds can have light-absorbing, anti-bacterial and anti-tumour utility.

Inventors

  • 👤 Robert Charles C/Othe Upjohn Company Kelly
  • 👤 Martha Ann C/O The Upjohn Company Warpehoski
  • 👤 Wendell C/O The Upjohn Company Wierenga

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-02 21:13
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P35/00

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 566 words
A compound selected from the -group consisting of wherein R 1 is CH 3 -, -CH 2 Ph, CH 2 =CHCH 2 -, -CH 2 SCH 3 , -CH 2 0CH 3 , -CH20CH 2 CH 2 0CH 3 , - CH 2CC1 3 , -CH2CH2Si(R 2 ) 3 , or where Ph is phenyl; R 2 is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(Ci-C 5 ), phenyl, or H; R 3 is alkyl(C 1 -C 5 ), phenyl, or H; X is Cl, Br, or I; or OSO 2 R 40 where R 40 is alkyl(C 1 -C 5 ), phenyl, tolyl, bromophenyl, nitrophenyl, or trifluoromethyl; R 50 is hydrogen or the same as R 5 ; R5 is a carbonyl acyl group selected from the group consisting of (i) where R6 is H, -alkyl(C 1 -C 20 ), -CC13, CF3, or NH2; (ii) where X 1 and/or X 2 is H, CH3, OH, OCH 3 , N0 2 , NH2. NNHAc, NHBz, or halogen; (iii) acyl derivatives (-C-CH-R 7 ) of the 20 natural amino acids ONH 2 where R 7 is the amino acid residue of glycine, alanine, valine, isoleucine, leucine, serine, threonine, aspartic acid, glutamic acid, lysine, arginine, asparagine, glutamine, cysteine, methionine, tryptophan, phenylalanine, tryosine and histidine or proline; and their common salts selected from Na⊕, K⊕, NH 4 ⊕, Cl⊖, PO 4 ⊖, and OAc⊖; (iv) where M⊕ is Na, K, NH 4 , or N(CH3)4; (v) (dimer) wherein n 1 = 2-12; (vi) where X 3 and/or X4 - H, OH, OCH3; (vii) where n 2 - 0.3; and R8 is H,CH 3 or C2H5; (viii) where X 5 = H, OH, OCH 3 , N0 2 , NH 2 , NAc, NCNH 2 ; NBz; NH-CN; and R8 has H H" H 0 the meaning defined above; (ix) where n 3 - 1, 2, or 3; and R 8 and R 5 have the meanings defined above; (x) where X 6 - H, N0 2 , NH2, (xi) or where R 9 = CH 3 or NH2 (xii) where R 8 and R9 have the meanings defined above; (xiii) (xiv) where (xv) -n 4 H where R 10 = CH 2 CH2, or CH-CH and X 7 - O, N , and n 4 = 1-4, and the HC1 and MeI salts for X 7 - NH; H (xvi) (dimer) where X 7 and R 11 and n 4 have the meanings defined above; (xvii) where X 8 is -O-, - S -, NH; X 9 is -CH- or -N-; and X 5 has the meanin defined above; (xviii) where X 5 has the meaning defined above; (xix) where X 10 is -CH- or -N- and X 7 is SH, NH 2 , OH, H or NHAc; (xx) where X 5 has the meaning defined above; (xxi) where X 5 and X 10 have the meanings defined above; and (xxii) where X6 and R 8 have the meanings defined above; and when any of X 1 to X6 is OH or NH 2 , then each of the R 5 groups represented here by ii, vi, viii, ix, x, xvii, xviii, xix, xx, xxi or xxii may be coupled with each other forming the following dimer combinations wherein the respective R 5 groups are bound together via a carboxy or an amide linkage;
Claim 2
Dependent Claim 566 words
A compound selected from the -group consisting of wherein R 1 is CH 3 -, -CH 2 Ph, CH 2 =CHCH 2 -, -CH 2 SCH 3 , -CH 2 0CH 3 , -CH20CH 2 CH 2 0CH 3 , - CH 2CC1 3 , -CH2CH2Si(R 2 ) 3 , or where Ph is phenyl; R 2 is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(Ci-C 5 ), phenyl, or H; R 3 is alkyl(C 1 -C 5 ), phenyl, or H; X is Cl, Br, or I; or OSO 2 R 40 where R 40 is alkyl(C 1 -C 5 ), phenyl, tolyl, bromophenyl, nitrophenyl, or trifluoromethyl; R 50 is hydrogen or the same as R 5 ; R5 is a carbonyl acyl group selected from the group consisting of (i) where R6 is H, -alkyl(C 1 -C 20 ), -CC13, CF3, or NH2; (ii) where X 1 and/or X 2 is H, CH3, OH, OCH 3 , N0 2 , NH2. NNHAc, NHBz, or halogen; (iii) acyl derivatives (-C-CH-R 7 ) of the 20 natural amino acids ONH 2 where R 7 is the amino acid residue of glycine, alanine, valine, isoleucine, leucine, serine, threonine, aspartic acid, glutamic acid, lysine, arginine, asparagine, glutamine, cysteine, methionine, tryptophan, phenylalanine, tryosine and histidine or proline; and their common salts selected from Na⊕, K⊕, NH 4 ⊕, Cl⊖, PO 4 ⊖, and OAc⊖; (iv) where M⊕ is Na, K, NH 4 , or N(CH3)4; (v) (dimer) wherein n 1 = 2-12; (vi) where X 3 and/or X4 - H, OH, OCH3; (vii) where n 2 - 0.3; and R8 is H,CH 3 or C2H5; (viii) where X 5 = H, OH, OCH 3 , N0 2 , NH 2 , NAc, NCNH 2 ; NBz; NH-CN; and R8 has H H" H 0 the meaning defined above; (ix) where n 3 - 1, 2, or 3; and R 8 and R 5 have the meanings defined above; (x) where X 6 - H, N0 2 , NH2, (xi) or where R 9 = CH 3 or NH2 (xii) where R 8 and R9 have the meanings defined above; (xiii) (xiv) where (xv) -n 4 H where R 10 = CH 2 CH2, or CH-CH and X 7 - O, N , and n 4 = 1-4, and the HC1 and MeI salts for X 7 - NH; H (xvi) (dimer) where X 7 and R 11 and n 4 have the meanings defined above; (xvii) where X 8 is -O-, - S -, NH; X 9 is -CH- or -N-; and X 5 has the meanin defined above; (xviii) where X 5 has the meaning defined above; (xix) where X 10 is -CH- or -N- and X 7 is SH, NH 2 , OH, H or NHAc; (xx) where X 5 has the meaning defined above; (xxi) where X 5 and X 10 have the meanings defined above; and (xxii) where X6 and R 8 have the meanings defined above; and when any of X 1 to X6 is OH or NH 2 , then each of the R 5 groups represented here by ii, vi, viii, ix, x, xvii, xviii, xix, xx, xxi or xxii may be coupled with each other forming the following dimer combinations wherein the respective R 5 groups are bound together via a carboxy or an amide linkage;
Claim 3
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 4
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 5
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 6
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 7
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 8
Dependent Claim 4 words
according to Claim 1.
Claim 9
Dependent Claim 9 words
A compound of the formula according to Claim 1.
Claim 10
Dependent Claim 12 words
A compound according to Claim 1 selected from the group consisting of
Claim 11
Dependent Claim 17 words
A compound according to Claim 19, formula (h) which is (7bR,8aS)-N-[2-((4,5,8,8a-tetrahydro-7-methyl-4-oxacyclopropa[c]benzo[1,2-b:4,3-b']dipyrrol-2(1H)-yl)carbonyl-1H-indole-5-yl)-1H-indole-3-carboxamide, or a pharmacologically acceptable salt thereof.

References Cited (Backward Citations)

US4423229A Cited

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