GB1271180A - Novel thiazoline azetidinone rearrangement products and their preparations, and synthesis of desacetoxycephalosporin and hydroxymethylpenicillin sulfoxides - Google Patents
Novel thiazoline azetidinone rearrangement products and their preparations, and synthesis of desacetoxycephalosporin and hydroxymethylpenicillin sulfoxidesInfo
- Publication number
- GB1271180A GB1271180A GB2780170A GB2780170A GB1271180A GB 1271180 A GB1271180 A GB 1271180A GB 2780170 A GB2780170 A GB 2780170A GB 2780170 A GB2780170 A GB 2780170A GB 1271180 A GB1271180 A GB 1271180A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- alkoxy
- alkenyl
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 title abstract 3
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title abstract 2
- 230000008707 rearrangement Effects 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 150000003462 sulfoxides Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- -1 methoxybenzyl Chemical group 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 238000010494 dissociation reaction Methods 0.000 abstract 2
- 230000005593 dissociations Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Chemical class 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class 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 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
- 239000002253 acid Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 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
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 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
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000006000 trichloroethyl group Chemical group 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83283669A | 1969-06-12 | 1969-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1271180A true GB1271180A (en) | 1972-04-19 |
Family
ID=25262743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2780170A Expired GB1271180A (en) | 1969-06-12 | 1970-06-09 | Novel thiazoline azetidinone rearrangement products and their preparations, and synthesis of desacetoxycephalosporin and hydroxymethylpenicillin sulfoxides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4939277B1 (enrdf_load_stackoverflow) |
| BR (1) | BR6915080D0 (enrdf_load_stackoverflow) |
| CH (2) | CH572940A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2029099C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2052961B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1271180A (enrdf_load_stackoverflow) |
| NL (1) | NL166944C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4067866A (en) | 1974-05-22 | 1978-01-10 | Societa' Farmaceutici Italia | Process for preparing cephalosporins and certain novel 2β-thiohydrazo-azetidinones as intermediates |
| US7507812B2 (en) | 2003-09-09 | 2009-03-24 | Nippon Chemical Industrial Co., Ltd. | Process for producing 3-chloromethyl-3-cephem derivatives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862164A (en) * | 1971-02-03 | 1975-01-21 | Lilly Co Eli | Thiazolidine azetidinones |
| GB1472866A (en) * | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
| GB1472863A (en) * | 1974-08-15 | 1977-05-11 | Farmaceutici Italia | Intermediates for cephalosporin synthesis |
| GB1472864A (en) * | 1975-04-05 | 1977-05-11 | Farmaceutici Italia | Method of preparing cephalosporins |
| US4439434A (en) * | 1981-09-18 | 1984-03-27 | Kureha Kagaku Kogyo Kabushiki Kaisha | Cephalosporin derivative and pharmaceutical composition containing the derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS157620B2 (en) * | 1965-09-10 | 1974-09-16 | Robert B Woodward | Method of 2-oxoazetidino (3,2-d)-thiazolidinmethanecarboxyl acid's esters making |
-
1969
- 1969-12-12 BR BR21508069A patent/BR6915080D0/pt unknown
-
1970
- 1970-06-05 NL NL7008271A patent/NL166944C/xx not_active IP Right Cessation
- 1970-06-08 CH CH215474A patent/CH572940A5/xx not_active IP Right Cessation
- 1970-06-08 CH CH857770A patent/CH565190A5/xx not_active IP Right Cessation
- 1970-06-09 GB GB2780170A patent/GB1271180A/en not_active Expired
- 1970-06-12 DE DE19702029099 patent/DE2029099C3/de not_active Expired
- 1970-06-12 JP JP45051481A patent/JPS4939277B1/ja active Pending
- 1970-06-12 FR FR7021775A patent/FR2052961B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4067866A (en) | 1974-05-22 | 1978-01-10 | Societa' Farmaceutici Italia | Process for preparing cephalosporins and certain novel 2β-thiohydrazo-azetidinones as intermediates |
| US7507812B2 (en) | 2003-09-09 | 2009-03-24 | Nippon Chemical Industrial Co., Ltd. | Process for producing 3-chloromethyl-3-cephem derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH565190A5 (enrdf_load_stackoverflow) | 1975-08-15 |
| DE2029099C3 (de) | 1979-02-08 |
| FR2052961A1 (enrdf_load_stackoverflow) | 1971-04-16 |
| DE2029099A1 (de) | 1971-01-28 |
| JPS4939277B1 (enrdf_load_stackoverflow) | 1974-10-24 |
| DE2029099B2 (de) | 1978-05-11 |
| NL7008271A (enrdf_load_stackoverflow) | 1970-12-15 |
| NL166944C (nl) | 1981-10-15 |
| NL166944B (nl) | 1981-05-15 |
| FR2052961B1 (enrdf_load_stackoverflow) | 1974-08-09 |
| CH572940A5 (enrdf_load_stackoverflow) | 1976-02-27 |
| BR6915080D0 (pt) | 1973-03-08 |
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