IL41027A - The preparation of semi-synthetic penicillins and cephalosporins and novel mixed phosphonic anhydrides used as intermediates therein - Google Patents
The preparation of semi-synthetic penicillins and cephalosporins and novel mixed phosphonic anhydrides used as intermediates thereinInfo
- Publication number
- IL41027A IL41027A IL41027A IL4102772A IL41027A IL 41027 A IL41027 A IL 41027A IL 41027 A IL41027 A IL 41027A IL 4102772 A IL4102772 A IL 4102772A IL 41027 A IL41027 A IL 41027A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- alkyl
- hydrogen
- same meaning
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims 8
- 229930186147 Cephalosporin Natural products 0.000 title claims 4
- 229940124587 cephalosporin Drugs 0.000 title claims 4
- 150000001780 cephalosporins Chemical class 0.000 title claims 4
- 150000002960 penicillins Chemical class 0.000 title claims 2
- 150000008064 anhydrides Chemical class 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- -1 phenoxy, naphthoxy Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 238000000034 method Methods 0.000 claims 6
- 229940049954 penicillin Drugs 0.000 claims 6
- 230000000865 phosphorylative effect Effects 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000004437 phosphorous atom Chemical group 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical compound C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 claims 1
- KGQCLZJFUIPDGS-UHFFFAOYSA-N dioxaphospholane Chemical compound C1CPOO1 KGQCLZJFUIPDGS-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. A process for preparing a semi-synthetic penicillin or semi-synthetic cephalosporin which comprises: (a) reacting a compound of the formula: or wherein R is hydrogen, (lower) alkanoyloxy containing 2 to 8 carbon atoms, phenoxy, naphthoxy or a quaternary ammonium radical; M is hydrogen, an alkali metal or a tertiary amine; ^ is a substituent selected from those contained in natural and semi-synthetic penicillins; and R^ is a substituent selected from those contained in natural and semi-synthetic cephalosporin; with a phosphorylating agent of the formula: R1 halogen - P * - R2 (R3) n wherein R is - 0; n is 0 or 1; R and R are selected from (lower) alkoxy, (lower) alkylthio , phenyl, naphthyl, phenoxy, naphthoxy, phenylthio, naphthylthio, phenyl (lower alkyl), naphthyl (lower alkyl), phenyl (lower) alkoxy, naphthyl (lower) alkoxy phenyl (lower) alkylthio, naphthyl (lower) alkylthio, halogen and •32- 41027/4 lower alkyl; or R and R may be joined together to form with the phosphorus atom the ring: wnerein .4 X is oxygen, siilfur or methylene and R is hydrogen or (lower) alkyl; m is an integer from 1 to 6 and when m is greater than 1 the group -(CH2)m~ can be either straight or branched chain; in the presence of an acid acceptor and an inert organic solvent at a temperature between about -40° and about +10 °C to obtain a compound of the formula: or wherein R, R^ , ^, ^ and n have the same meaning as above, 1 · 2 ' 1 2 R and R have the same meaning as R and R above but -33- 41027/2 may also represent a radical of the formula III when said starting compound is a compound of formula la or a radical of formula IV when said starting compound compound of formula lb (b) reacting an acid halide with a compound obtained in step (a) in the presence of an acid acceptor at a temperature below 0°C to produce the corresponding imino halide; (c) reacting said imino halide compound with an alcohol at a temperature below about -10°C to convert said imino halide compound to the hydrohalide salt of the corresponding imino ether compound; (d) converting said imino ether compound by hydrolysis at a temperature below about -20°C to the hydrohalide salt of a compound of the formula: -34- 41027/2 or 1 ' 2 ' 3 wherein R, R , R , R and n have the same meaning as above; (e) reacting a compound formed in step (d) with an acylating agent selected from an organic carboxylic acid and a functional reactive derivative of such acid in the presence of an acid acceptor to obtain acylation of the amino group; and (f) treating said acylated compound with sufficient water to obtain a member selected from the class consisting of a free base of the following formula: Villa or 0- Vlllb -35- 41027/^, wherein R has the same meaning as above, or the corresponding •acid addition salt where a free amino group is present on the acyl radical. 15 16
2. A process according to Claim 1 wherein R and R are a substituent selected from those contained in a natural penicillin and natural cephalosporin.
3. A process according to Claim 1 or 2, wherein said phosphorylating agent is a compound selected from those of the formula: in which R is hydrogen or alkyl and m has the same meaning as in Claim 1.
4. A process according to Claim 1, 2 or 3, wherein said acyl radical is selected from the class consisting of those having the following formulae: -37- 41027/3,-, wherein: 6 7 R and R are hydrogen or lower) alkoxy ; R is hydrogen, (lower) alkyl or phenyl; 9 10 R and R are hydrogen or halogen; 11 12 R and R are hydrogen, halogen, ( lower) alkyl , (lower) alkoxy , phenyL or phenoxy; 13 R is hydrogen, (lower) alkyl or aryl; a is 0 or 1; b is an integer from 0 through 5; c is 0, 1 or 2; d is 1, 2 or 3, with the proviso that when a is 0, d is greater than 1, and when a is 1, d is less than 3.
5. A process for preparing a semi-synthetic penicillin according to Claim 1, which comprises: (a) reacting a penicillin compound of the formula: wherein M is hydrogen, an alkali metal or a tertiary amine; and. 15 ' R is phenoxymethyl or benzyl; with a phosphorylating agent of the formula: wherein m is an integer from 1 to 6, and when m is greater than 1 the group ~(Cii2^m~ can e^-t^ier -38- 41027/4 *4 wherein R and m have the same meaning as above; said reaction being carried out under anhydrous conditions in the presence of an organic solvent and an acid acceptor at a temperature in the range of about -40°C to about +10°C, the molar xatio of said penicillin compound to said phosphorylating agent being about 0.5:1 to about 3:1; (b) reacting said compound obtained in step (a) with an acid chloride in the presence of an acid acceptor at a temperature between about -10°C and -65°C to produce an imino chloride compound of the formula: wherein R and m have the same meaning as above; (c) reacting said imino chloride with an alcohol at a temperature below about -10 °C to produce an imino ether of the formula: 0Ra R15'- i-H Γ- Ί -39- 41027/3 wherein R and m have the same meaning as above; and R is lower alkyl , hydroxy ( lower) alkyl , phenyl (lower) alkyl , cycloalkyl, aryloxy (lower) alkyl or (lower) alkoxy (lower) alkyl ; (d) reacting said imino ether with water at a temperature below about -20°C and treating the resulting compound with a reactive derivative of an organic carboxylic acid in the presence of an acid acceptor at a temperature between about 0°C and -60°C to produce a compound of the formula: wherein R and m have the same meaning as above; (e) and hydmLyzing the resulting acylated product to remo the carboxyl protective group and obtain a semi-synthetic penicillin of the formula Villa in Claim 1, or the corresponding acid addition salt where a free amino group is present on the acyl radical.
6. A process according to Claim 5, wherein the phosphorylating agent is selected from the class consisting of 2-chloro-l , 3 , 2-dioxaphospholane and 2-chloro-l , 3 , 2-dioxa-phosphorinane .
7. A process according to Claim 6, wherein the acylating agent is D (-) phenylglycyl chloride hydrochloride.
8. A process according to Claim 2, wherein the phosphorylating agent is phosphorus trichloride.
9. A hydrohalide salt of a compound of the formula: -40- 41027/4 1" 2" wherein R" is hydrogen or acetoxy; and R and R are each 1 " 2 " chlorine, or R and R are joined together to form with the phosphorus atom the ring wherein m is an integer from 1 to 6, and when m is greater than 1 the group -(CH2)m~ can either be straight or branched chain.
10. The hydrohalide salt of a compound of the formula: -41- 41027/2 wherein m is an integer from 1 to 6, and when m is greater than 1 the group ~^c^2^m~ can e:*-tner be straight or branched chain.
11. A compound according to Claim 10, which is the hydrochloride salt of 6-aminopenicillanic acid, 1,3,2-dioxaphospholan-2-yl ester. ND:ed
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/217,942 US3962215A (en) | 1971-10-04 | 1972-01-14 | Intermediates for preparing semi-synthetic penicillins and processes relating thereto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41027A0 IL41027A0 (en) | 1973-02-28 |
| IL41027A true IL41027A (en) | 1976-08-31 |
Family
ID=22813112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41027A IL41027A (en) | 1972-01-14 | 1972-12-07 | The preparation of semi-synthetic penicillins and cephalosporins and novel mixed phosphonic anhydrides used as intermediates therein |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4880590A (en) |
| AR (2) | AR194868A1 (en) |
| AU (1) | AU477307B2 (en) |
| BE (1) | BE793975A (en) |
| BR (1) | BR7300269D0 (en) |
| CA (1) | CA1024981A (en) |
| CH (1) | CH592684A5 (en) |
| DE (1) | DE2301014A1 (en) |
| FR (2) | FR2168068B1 (en) |
| GB (3) | GB1405073A (en) |
| IE (3) | IE37111B1 (en) |
| IL (1) | IL41027A (en) |
| NL (1) | NL7300505A (en) |
| PH (2) | PH13289A (en) |
| ZA (1) | ZA73250B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2548565B1 (en) * | 1983-07-05 | 1986-05-16 | Gallay Sa | METHOD FOR REINFORCING CRIMP AND CRIMPED JOINTS, ESPECIALLY FOR PACKAGING |
| GB2524326B (en) | 2014-03-21 | 2017-12-20 | Tim Wong Leung | Novel freight container |
-
1972
- 1972-12-07 IL IL41027A patent/IL41027A/en unknown
-
1973
- 1973-01-04 PH PH14232A patent/PH13289A/en unknown
- 1973-01-10 DE DE2301014A patent/DE2301014A1/en not_active Ceased
- 1973-01-12 AR AR246093A patent/AR194868A1/en active
- 1973-01-12 FR FR7301158A patent/FR2168068B1/fr not_active Expired
- 1973-01-12 NL NL7300505A patent/NL7300505A/xx not_active Application Discontinuation
- 1973-01-12 BE BE793975D patent/BE793975A/en unknown
- 1973-01-12 ZA ZA730250A patent/ZA73250B/en unknown
- 1973-01-12 CH CH48373A patent/CH592684A5/xx not_active IP Right Cessation
- 1973-01-12 BR BR73269A patent/BR7300269D0/en unknown
- 1973-01-12 CA CA161,199A patent/CA1024981A/en not_active Expired
- 1973-01-12 JP JP48006081A patent/JPS4880590A/ja active Pending
- 1973-01-15 IE IE2755/75A patent/IE37111B1/en unknown
- 1973-01-15 GB GB1141274A patent/GB1405073A/en not_active Expired
- 1973-01-15 GB GB1141174A patent/GB1405072A/en not_active Expired
- 1973-01-15 IE IE60/73A patent/IE37109B1/en unknown
- 1973-01-15 AU AU51122/73A patent/AU477307B2/en not_active Expired
- 1973-01-15 GB GB199373A patent/GB1405071A/en not_active Expired
- 1973-01-15 IE IE2754/75A patent/IE37110B1/en unknown
- 1973-08-01 AR AR249401A patent/AR195441A1/en active
- 1973-08-06 FR FR7328678A patent/FR2187795B1/fr not_active Expired
-
1977
- 1977-02-21 PH PH19477A patent/PH13692A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR195441A1 (en) | 1973-10-08 |
| IE37111B1 (en) | 1977-05-11 |
| GB1405072A (en) | 1975-09-03 |
| ZA73250B (en) | 1974-08-28 |
| IE37109L (en) | 1973-07-14 |
| IE37109B1 (en) | 1977-05-11 |
| BE793975A (en) | 1973-07-12 |
| FR2187795B1 (en) | 1977-05-13 |
| CH592684A5 (en) | 1977-11-15 |
| FR2187795A1 (en) | 1974-01-18 |
| NL7300505A (en) | 1973-07-17 |
| GB1405073A (en) | 1975-09-03 |
| IE37110B1 (en) | 1977-05-11 |
| AR194868A1 (en) | 1973-08-24 |
| DE2301014A1 (en) | 1973-07-19 |
| CA1024981A (en) | 1978-01-24 |
| JPS4880590A (en) | 1973-10-29 |
| FR2168068A1 (en) | 1973-08-24 |
| PH13289A (en) | 1980-03-04 |
| PH13692A (en) | 1980-09-01 |
| IL41027A0 (en) | 1973-02-28 |
| FR2168068B1 (en) | 1977-02-11 |
| BR7300269D0 (en) | 1973-10-25 |
| GB1405071A (en) | 1975-09-03 |
| AU477307B2 (en) | 1976-10-21 |
| AU5112273A (en) | 1974-07-18 |
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