IE37209L - 3-oxyiminomethyl cephalosporin compounds - Google Patents
3-oxyiminomethyl cephalosporin compoundsInfo
- Publication number
- IE37209L IE37209L IE721732A IE173272A IE37209L IE 37209 L IE37209 L IE 37209L IE 721732 A IE721732 A IE 721732A IE 173272 A IE173272 A IE 173272A IE 37209 L IE37209 L IE 37209L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- protected
- opt
- alkanoyl
- tert
- Prior art date
Links
- -1 cephalosporin compounds Chemical class 0.000 title abstract 12
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001240 enamine group Chemical group 0.000 abstract 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cpds. of formula (I): where n = 0 or 1 R=H, alkanoyl, (1-8C) chloro- or bromo-alkanoyl (2-8C) azidoacetyl cyanoacetyl, a gp (II): where Q = H, or methyl; Ar = 2- or 3-thienyl, 2- or 3-furyl, 2- or 3- pyrrolyl or phenyl opt. substd. with >=1 Cl, Br, I, F, CF3, hydroxy, alkyl, or alkoxy (1-3C) cyano or nitro, whereby >=1 of these substituents must be in m- or p-posn at the phenyl ring; Ar-X-CH2-C(O)-, where X = -O or -S; Ar = as signified or 4-pyridyl and X = -S; a gp. (III): Ar-C(X1)H-C(O)- where X1 = -NH2, -NH3 circled positive, amino protected by benzyloxycarbonyl, alkoxycarbonyl (1-4C) cyclopentoxycarbonyl, cyclohexoxy-carbonyl, benzhydryloxycarbonyl, triphenylmethyl, 2,2,2-trichloroethoxycarbonyl, a gp. (IV):- C(O)NH-C (=NH)-NH2 -SO3H, or phthalimido, the enamine form of methylacetylacetate or acetylacetone; or X1 = hydroxyl opt. protected by esterification with an alkanecarboxylic acid (1-6C) carboxyl, opt. protected by esterification with an alkanol (1-6C) or a gp, -N3, -CN or -C(O)NH2; or R = 2-sydnone-3-(C1-C3) alknoyl or a gp. (V): where m = 0,1 or 2; 5-aminodipoyl opt. amino-protected with alkanoyl (1-3C) or chloroalkanoyl (1-3C) or carboxyl-protected with benzyhydryl, 2,2,2-trichloroethyl, alkyl (4-6C) or nitrobenzyl; R1 = H, or R+R1+N = H3N- circled positive a salt gp. with an acid with a pK a-value of 4, or a cyclic imide derived from a dicarboxylic acid or a hydrocarbon (3-12C), a gp (VI); where Z = (-CH2-)y y = 1 or 2; or -O; or R+R1+N = (alkyl)2-N-CH=N- (alkyl 1-2C); R2 = tert. alkyl (4-6C) tert. alkenyl- or tert. alkynyl (5-7C) benzyl, methoxybenzyl, nitrobenzyl, 2,2,2-trichloroethyl, 3,5-di(t. butyl)4-hydroxybenzyl, acetoxymethyl, pivaloyloxymethyl, 2-iodoethyl, benzhydryl, phenacyl, trimethylsilyl, succinimidomethyl, phthalimidomethyl or H; Y = H, alkyl (1-6C), haloalkyl (2-6C) where halo = Cl or Br; aromatic hydrocarbon (6-12C) cycloalkyl (4-7C), alkylene-X-alkyl, where alkylene = 1-3C and X -O or -S; -CH2COOR3 where R3 = H or alkyl (1-6C), or -CH2CH2N(CH3)2. Pharmaceutically acceptable salts of (I) are included.
[FR2164793A1]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21178471A | 1971-12-23 | 1971-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37209L true IE37209L (en) | 1973-06-23 |
| IE37209B1 IE37209B1 (en) | 1977-05-25 |
Family
ID=22788358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1732/72A IE37209B1 (en) | 1971-12-23 | 1972-12-12 | 3-oxyiminomethyl cephalosporin compounds |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4868594A (en) |
| AR (1) | AR206767A1 (en) |
| AT (1) | AT323325B (en) |
| AU (1) | AU464412B2 (en) |
| BE (1) | BE793178A (en) |
| BG (1) | BG22838A3 (en) |
| CH (1) | CH565187A5 (en) |
| DD (1) | DD103901A5 (en) |
| ES (1) | ES409979A1 (en) |
| FR (1) | FR2164793A1 (en) |
| HU (1) | HU166210B (en) |
| IE (1) | IE37209B1 (en) |
| IL (1) | IL41020A (en) |
| NL (1) | NL7217421A (en) |
| PL (1) | PL88471B1 (en) |
| RO (1) | RO61182A (en) |
| SU (1) | SU525429A3 (en) |
| ZA (1) | ZA728675B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5652907B2 (en) * | 1972-12-25 | 1981-12-15 | ||
| JPS49109391A (en) * | 1973-02-28 | 1974-10-17 | ||
| JPS5715597B2 (en) * | 1973-12-20 | 1982-03-31 | ||
| AT402072B (en) * | 1994-04-25 | 1997-01-27 | Biochemie Gmbh | Cephem derivatives and process for their preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3351596A (en) * | 1966-09-21 | 1967-11-07 | Lilly Co Eli | 3-formyl cephalosporins |
-
0
- BE BE793178D patent/BE793178A/en unknown
-
1972
- 1972-01-01 AR AR245801A patent/AR206767A1/en active
- 1972-12-06 IL IL41020A patent/IL41020A/en unknown
- 1972-12-07 ZA ZA728675A patent/ZA728675B/en unknown
- 1972-12-07 AU AU49753/72A patent/AU464412B2/en not_active Expired
- 1972-12-12 IE IE1732/72A patent/IE37209B1/en unknown
- 1972-12-16 BG BG022143A patent/BG22838A3/en unknown
- 1972-12-20 PL PL1972159706A patent/PL88471B1/pl unknown
- 1972-12-20 NL NL7217421A patent/NL7217421A/xx not_active Application Discontinuation
- 1972-12-21 AT AT1094972A patent/AT323325B/en not_active IP Right Cessation
- 1972-12-21 RO RO73251A patent/RO61182A/ro unknown
- 1972-12-21 FR FR7245635A patent/FR2164793A1/en active Granted
- 1972-12-22 SU SU1864316A patent/SU525429A3/en active
- 1972-12-22 HU HUEI451A patent/HU166210B/hu unknown
- 1972-12-22 CH CH1880672A patent/CH565187A5/xx not_active IP Right Cessation
- 1972-12-22 DD DD167848A patent/DD103901A5/xx unknown
- 1972-12-22 ES ES409979A patent/ES409979A1/en not_active Expired
- 1972-12-23 JP JP48004452A patent/JPS4868594A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU4975372A (en) | 1974-06-13 |
| IL41020A0 (en) | 1973-02-28 |
| PL88471B1 (en) | 1976-09-30 |
| NL7217421A (en) | 1973-06-26 |
| FR2164793A1 (en) | 1973-08-03 |
| AR206767A1 (en) | 1976-08-23 |
| AT323325B (en) | 1975-07-10 |
| FR2164793B1 (en) | 1976-03-05 |
| CH565187A5 (en) | 1975-08-15 |
| AU464412B2 (en) | 1975-08-28 |
| ES409979A1 (en) | 1976-05-16 |
| IE37209B1 (en) | 1977-05-25 |
| IL41020A (en) | 1976-08-31 |
| SU525429A3 (en) | 1976-08-15 |
| JPS4868594A (en) | 1973-09-18 |
| BG22838A3 (en) | 1977-04-20 |
| DD103901A5 (en) | 1974-02-12 |
| ZA728675B (en) | 1974-07-31 |
| BE793178A (en) | 1973-06-22 |
| HU166210B (en) | 1975-02-28 |
| RO61182A (en) | 1976-11-15 |
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