IL42528A - Preparation of 3-methyl-cephem,3-halo-3-methyl-cephem and 2-halomethyl-2-methyl-penam derivatives - Google Patents
Preparation of 3-methyl-cephem,3-halo-3-methyl-cephem and 2-halomethyl-2-methyl-penam derivativesInfo
- Publication number
- IL42528A IL42528A IL42528A IL4252873A IL42528A IL 42528 A IL42528 A IL 42528A IL 42528 A IL42528 A IL 42528A IL 4252873 A IL4252873 A IL 4252873A IL 42528 A IL42528 A IL 42528A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- compound
- mole
- tertiary amine
- cephem
- Prior art date
Links
- LFMBIMXJWIQULB-SSDOTTSWSA-N (6r)-3-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC(C)=CN2C(=O)C[C@H]21 LFMBIMXJWIQULB-SSDOTTSWSA-N 0.000 title 1
- -1 3-methyl-3-hydroxy-cepham compound Chemical class 0.000 claims 9
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000003512 tertiary amines Chemical class 0.000 claims 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005042 acyloxymethyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 159000000011 group IA salts Chemical class 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Claims (10)
1. Process for converting a 3-methyl-3-hydroxy-cepham compound, which comprises reacting a compound of the formula I 0 with a halogen reagent selected from the group consisting of PX^ and SOXg in the presence of at least about one mole of an alkaline reagent selected from the group consisting of a tertiary amine and an inorganic alkaline salt per each mole of the 3-methyl-3-hydroxycepham compound and at a temperature within the range of from about 60°C. to about 150°C„ to obtain a mixture comprising a compound of the formula II COOEL a compound of the formula III and a compound of the formula 0 in which, in the above formulae, R is the residue of an imide derived from a diearboxylic acid, Rj is a carboxy protecting group and X is chlorine or bromine,
2. Process of claim 1, in which R is C2-C^ alkylene," alkenylene, -CH2-Y-CH2- in which Y is oxygen or sulfur, i,2-cyelohexylene, 1, 2-phenylene, 1,2-cyclohexenylene , or a substituted derivative of an of the above having from 1 to substituents selected from the group consisting of C1~C3 alkvl» ci"C3 alkoxv» nitro, fluoro, chloro, bromo, or iodo.
3. Process of claim 2, in which R is Cg-C^ alkylene, C2-C^ alkenylene, -CH2-Y-CH2-in which Y is oxygen or sulfur, 1 ,2-cyclohexylene , 1, 2-phenylene, or 1 , 2-cyclohexenylene .
4. Process of claim 1, 2 or 3, in which R^ is C1-C^ alkyl, 2 , 2 , 2-trihaloethyl , 2-iodoethyl, benzyl, p_-Jiitrobenzyl, succinimidomethyl , phthalimidomethyl, £-methoxybenzyl, benzhydryl, C -C, alkanoyloxymethyl , phen- ϊ 2 o acyl, or £-halophenacyl.
5. Process of any one of claims 1-^, in which the halogen reagent is present in an amount of from about lol to about 2,0 moles per each mole of the 3-methyl-3- hydroxycepham compound.
6. Process of claim 5, n which the alkaline reagent is a tertiary amine and R is 1, 2-phenylene,
7. Process of claim 6, in which the tertiary amine is present in an amount of from about 1.0. to about 2.0 moles per each mole of the 3-methyl-3-hydroxycepham compound,,
8. Process of any one of claims 1-7, in which X is chlorine.
9. Process of any one of claims 1-8, in which the tertiary amine is triethylamine.
10. Process of any one of claims 1-9, in which R-j^ is p-nitrobenzyl or p-methoxybenzyl .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26779672A | 1972-06-30 | 1972-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42528A0 IL42528A0 (en) | 1973-08-29 |
| IL42528A true IL42528A (en) | 1976-08-31 |
Family
ID=23020150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42528A IL42528A (en) | 1972-06-30 | 1973-06-18 | Preparation of 3-methyl-cephem,3-halo-3-methyl-cephem and 2-halomethyl-2-methyl-penam derivatives |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4955685A (en) |
| BE (1) | BE801497A (en) |
| CH (1) | CH580635A5 (en) |
| DE (1) | DE2333291A1 (en) |
| FR (1) | FR2190829B1 (en) |
| GB (1) | GB1382756A (en) |
| IE (1) | IE37839B1 (en) |
| IL (1) | IL42528A (en) |
| NL (1) | NL7309168A (en) |
-
1973
- 1973-06-18 GB GB2879973A patent/GB1382756A/en not_active Expired
- 1973-06-18 IL IL42528A patent/IL42528A/en unknown
- 1973-06-22 IE IE1040/73A patent/IE37839B1/en unknown
- 1973-06-27 FR FR7323493A patent/FR2190829B1/fr not_active Expired
- 1973-06-27 CH CH937973A patent/CH580635A5/xx not_active IP Right Cessation
- 1973-06-27 BE BE1005193A patent/BE801497A/en unknown
- 1973-06-29 DE DE19732333291 patent/DE2333291A1/en active Pending
- 1973-06-29 NL NL7309168A patent/NL7309168A/xx unknown
- 1973-06-30 JP JP48074327A patent/JPS4955685A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH580635A5 (en) | 1976-10-15 |
| FR2190829A1 (en) | 1974-02-01 |
| FR2190829B1 (en) | 1977-02-18 |
| IE37839L (en) | 1973-12-30 |
| BE801497A (en) | 1973-12-27 |
| NL7309168A (en) | 1974-01-02 |
| IE37839B1 (en) | 1977-10-26 |
| DE2333291A1 (en) | 1974-01-03 |
| GB1382756A (en) | 1975-02-05 |
| IL42528A0 (en) | 1973-08-29 |
| JPS4955685A (en) | 1974-05-30 |
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