IL37522A - Thioesters containing an azacyclobutanone ring derived from penicillins and a method for preparing the same - Google Patents
Thioesters containing an azacyclobutanone ring derived from penicillins and a method for preparing the sameInfo
- Publication number
- IL37522A IL37522A IL37522A IL3752271A IL37522A IL 37522 A IL37522 A IL 37522A IL 37522 A IL37522 A IL 37522A IL 3752271 A IL3752271 A IL 3752271A IL 37522 A IL37522 A IL 37522A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- alkylthio
- alkoxy
- benzyl
- methyl
- Prior art date
Links
- 150000007970 thio esters Chemical class 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 3
- 229930182555 Penicillin Natural products 0.000 title 1
- 150000002960 penicillins Chemical class 0.000 title 1
- -1 methoxybenzyl Chemical group 0.000 claims abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract 4
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims abstract 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-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
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 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
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000006000 trichloroethyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1320256 Azetidinones and cephalosporins ELI LILLY & CO 9 Sept 1971 [10 Sept 1970] 42179/71 Headings C2A and C2C Novel, therapeutic compounds (I) and (II) where A is phthalimido or RCONH-, R is H, ethoxycarbonyl, or C 1-8 alkyl, C 3-8 cycloalkyl or C 2-8 alkenyl optionally substituted with OH, SH, C 1-3 -alkoxy or -alkylthio or CN, or is a group of Formula (III), (IV) or (V) where Q is H, OH, SH, Cl, Br, C 1-3 -alkyl, -alkoxy or -alkylthio, NO 2 or CN, X is O, S or a direct bond, Y is OH, SH or NH 2 , m is 0, 1 or 2, n is 1 or 2, R<SP>1</SP> is -CH 2 OZ, -CH 2 O.CO.Z, -CONHZ or -CO 2 R<SP>11</SP> where R<SP>11</SP> is C 1-4 alkyl, C 4-6 tert-alkyl, C 5-8 tertalkenyl or -alkynyl, benzyl, methoxybenzyl, nitrobenzyl, benzhydryl, phthalimidomethyl, succinimidomethyl, phenacyl or trichloroethyl, Z is H, C 1-8 alkyl, C 3-8 cycloalkyl, or C 2-8 alkanyl, optionally substituted with OH, SH, C 1-3 -alkoxy or -alkylthio or CN or Z is phenyl or phenyl-C 1-3 -alkyl optionally substituted with OH, SH, Cl, Br, C 1-3 -alkyl, -alkoxy or -alkylthio, NO 2 or CN and W is Me, Et, Pr or Ph, are made by treating (VI) with triphenyl phosphine or trialkyl phosphite in the presence of acetic, propionic, butyric or benzoic anhydride (I is obtained; it is converted to the isomer II by treatment with base). Cephalosporins (VII) are obtained by oxidizing (I) or (II); (VII) can be dehydrated to give the corresponding unsaturated compound.
[GB1320256A]
Claims (4)
1. A thioester useful as an intermediate for the preparation of cephalosphorin antibiotics having the formula: 0 A-CH-CH-S-C-W 0=C -N -CH-OCH9 I I R« CH3 0 wherein A is -NH ; R is benzyl or phenoxymethyl R» is trichloroethoxycarbbnyl or p-nitrobenzyloxycarbonyl; and W is methyl, ethyl, propyl, or isopropyl. :-■ ■ '■ '■· ■ ■ o '1 '' ' ' , 1 ' ' ' · · ,:u
2. A thioester as in claim 1 wherein A is -R-C-NH, R is phenoxymethyl, and W is methyl. P
3. A thioester, as in claim 1 wherein A is -R-C-NH, R is benzyl,and W is methyl.
4. A method for the preparation of a thioester having the formula 0 A-CH'-CH-S-C-W I t 0*C -N-CH-CH=CH« » ' R' CH3 which comprises treating a penicillin sulfoxide having the formula A*CHHCH ¾)=C- N CH-R' 37522/2 with at least one equivalent of triphenyl phosphine or a trialkyl phosphite wherein the alkyl groups contain from 1 to 4 carbon atoms at a temperature within the range.of 40* to 125°C. in the presence of or at least one equivalent of acetic anhydride, peopionic anhydride,/butyric anhydride or boncoio onhydrido, wherein in the formulas 11 0 R is benzyl , or phenoxyraeth l R' is trichloroethoxycarbonyl or p-nitrobenzyloxycarbonyl ; and is methyl, ethyl , propyl , or isopropyl . . ■ ' ■' 0 ■ II Si A method as in claim 4 wherein A is -R-C-NH, R is benzyl and W is methyl i -22-
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7121870A | 1970-09-10 | 1970-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37522A0 IL37522A0 (en) | 1971-12-29 |
| IL37522A true IL37522A (en) | 1976-01-30 |
Family
ID=22099989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37522A IL37522A (en) | 1970-09-10 | 1971-08-18 | Thioesters containing an azacyclobutanone ring derived from penicillins and a method for preparing the same |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | AT316741B (en) |
| AU (1) | AU456466B2 (en) |
| BE (1) | BE772326A (en) |
| CA (1) | CA964663A (en) |
| CH (1) | CH564010A5 (en) |
| CS (1) | CS172930B2 (en) |
| DD (1) | DD99370A5 (en) |
| DE (1) | DE2145354C3 (en) |
| ES (1) | ES394984A1 (en) |
| FR (1) | FR2106435B1 (en) |
| GB (1) | GB1320256A (en) |
| HU (1) | HU165334B (en) |
| IE (1) | IE35582B1 (en) |
| IL (1) | IL37522A (en) |
| NL (1) | NL172652C (en) |
| PL (1) | PL87264B1 (en) |
| SE (1) | SE394428B (en) |
| SU (1) | SU515449A3 (en) |
| ZA (1) | ZA715418B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2045236A (en) * | 1979-03-26 | 1980-10-29 | Hoechst Uk Ltd | Oxapenem derivatives |
| GB2099817B (en) * | 1981-04-10 | 1985-05-15 | Otsuka Kagaku Yakuhin | Azetidinone derivatives and process for the preparation of the same |
| CN116332881B (en) * | 2023-05-30 | 2023-08-08 | 大连理工常熟研究院有限公司 | Preparation method of thioester derivative |
-
1971
- 1971-08-13 ZA ZA715418A patent/ZA715418B/en unknown
- 1971-08-18 IL IL37522A patent/IL37522A/en unknown
- 1971-08-23 AU AU32629/71A patent/AU456466B2/en not_active Expired
- 1971-08-24 SE SE7110697A patent/SE394428B/en unknown
- 1971-08-27 CA CA121,567A patent/CA964663A/en not_active Expired
- 1971-08-31 IE IE1105/71A patent/IE35582B1/en unknown
- 1971-09-07 PL PL1971150386A patent/PL87264B1/pl unknown
- 1971-09-07 NL NLAANVRAGE7112319,A patent/NL172652C/en not_active IP Right Cessation
- 1971-09-08 CS CS6407A patent/CS172930B2/cs unknown
- 1971-09-08 SU SU1698455A patent/SU515449A3/en active
- 1971-09-08 BE BE772326A patent/BE772326A/en unknown
- 1971-09-09 HU HUEI391A patent/HU165334B/hu unknown
- 1971-09-09 CH CH1321771A patent/CH564010A5/xx not_active IP Right Cessation
- 1971-09-09 AT AT783871A patent/AT316741B/en not_active IP Right Cessation
- 1971-09-09 GB GB4217971A patent/GB1320256A/en not_active Expired
- 1971-09-10 DE DE2145354A patent/DE2145354C3/en not_active Expired
- 1971-09-10 ES ES394984A patent/ES394984A1/en not_active Expired
- 1971-09-10 DD DD157671A patent/DD99370A5/xx unknown
- 1971-09-10 FR FR7132756A patent/FR2106435B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PL87264B1 (en) | 1976-06-30 |
| DD99370A5 (en) | 1973-08-05 |
| AT316741B (en) | 1974-07-25 |
| NL172652C (en) | 1983-10-03 |
| FR2106435B1 (en) | 1975-02-07 |
| FR2106435A1 (en) | 1972-05-05 |
| AU456466B2 (en) | 1974-12-19 |
| DE2145354A1 (en) | 1972-03-16 |
| DE2145354B2 (en) | 1979-06-21 |
| DE2145354C3 (en) | 1980-02-21 |
| CH564010A5 (en) | 1975-07-15 |
| GB1320256A (en) | 1973-06-13 |
| HU165334B (en) | 1974-08-28 |
| NL172652B (en) | 1983-05-02 |
| ZA715418B (en) | 1973-03-28 |
| SU515449A3 (en) | 1976-05-25 |
| IL37522A0 (en) | 1971-12-29 |
| AU3262971A (en) | 1973-03-01 |
| NL7112319A (en) | 1972-03-14 |
| CA964663A (en) | 1975-03-18 |
| ES394984A1 (en) | 1974-12-16 |
| IE35582L (en) | 1972-03-10 |
| IE35582B1 (en) | 1976-03-31 |
| SE394428B (en) | 1977-06-27 |
| CS172930B2 (en) | 1977-01-28 |
| BE772326A (en) | 1972-03-08 |
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