GB1361199A - Mercaptoalcohols and process for their manufacture - Google Patents
Mercaptoalcohols and process for their manufactureInfo
- Publication number
- GB1361199A GB1361199A GB4996471A GB4996471A GB1361199A GB 1361199 A GB1361199 A GB 1361199A GB 4996471 A GB4996471 A GB 4996471A GB 4996471 A GB4996471 A GB 4996471A GB 1361199 A GB1361199 A GB 1361199A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- compounds
- penam
- penicillin
- oct
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical class SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 title 1
- 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 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229940056360 penicillin g Drugs 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- -1 penicillin-G triethylammonium salt Chemical class 0.000 abstract 2
- KIWFDBBSSAVQGP-UHFFFAOYSA-N 3-propan-2-yl-4-thia-2,6-diazabicyclo[3.2.0]heptan-7-one Chemical compound S1C(C(C)C)NC2C(=O)NC21 KIWFDBBSSAVQGP-UHFFFAOYSA-N 0.000 abstract 1
- CMBKKEMURPWJHO-UHFFFAOYSA-N 4,4-dimethyl-5-thia-2,7-diazabicyclo[4.2.0]oct-2-ene Chemical compound CC1(C=NC2CNC2S1)C CMBKKEMURPWJHO-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000004651 carbonic acid esters Chemical group 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 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
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1361199 Azetidinone derivatives CIBA-GEIGY AG 27 Oct 1971 [27 Oct 1970 10 Nov 1970 4 March 1971 25 May 1971] 49964/71 Headings C2A C2C and C2P Novel compounds (I) (including salts and isomers thereof) where R<SP>a</SP> 1 is H or a protecting group, R<SP>b</SP> 1 is H or acyl or R<SP>a</SP> 1 and R<SP>b</SP> 1 taken together signify a bivalent protecting group, R 2 is H or acyl and R 3 and R 4 are H or an organic radical bonded via a carbon atom are made by reacting compounds (II) with compounds (III) while simultaneously effecting treatment with a reducing agent (R<SP>A</SP> 1 is a protecting group). Compounds VIII, IX, XI, XII, XIII, XIV and XIVa are also prepared (XIVa is not isolated) as well as 3-isopropyl-4-thia-2,6-diazabicyclo[3,2,0]heptane- 7 - one and 4,4 - dimethyl- 5 - thia - 2,7-diazabicyclo[4,2,0]oct- 2 - en (and 2 - an - ) - 8-ones. (R<SP>A</SP> 5 and R 5 are organic radicals, Z is, e.g. halogen, R a , Rb and R c are, e.g. Ph and X 1 , in particular, is such that O-CO-X 1 is a carbonic acid ester group). The following synthesis is described and exemplified: penicillin-G # penicillin-G triethylammonium salt # penicillin-G azide # 2,2-dimethyl-6#-phenylacetylamino - 3 - (2,2,2 - trichloroethoxy - carbonyl-amino)-penam (XV) (optionally via 3 -isocyanato - 2,2 - dimethyl - 6# - phenyl - acetylamino - penam); (XV) # 6# - amino - 2,2 - dimethyl - 3 - (2,2,2 - trichloroethoxycarbonylamino)-penam. Pharmaceutical preparations especially active against micro-organisms contain (XIV) as active ingredient.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1584570A CH542841A (en) | 1970-10-27 | 1970-10-27 | 3-amino-4-(2-hydroxyethylthio)-2-oxo-azetidine derivs-pref contng ant - n-acyl derivs -intermediates for cpds with antibacterial activity |
| CH1663370 | 1970-11-10 | ||
| CH319771 | 1971-03-04 | ||
| CH760871 | 1971-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1361199A true GB1361199A (en) | 1974-07-24 |
Family
ID=27428585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4996471A Expired GB1361199A (en) | 1970-10-27 | 1971-10-27 | Mercaptoalcohols and process for their manufacture |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE774481A (en) |
| DE (1) | DE2151560A1 (en) |
| FR (1) | FR2113239A5 (en) |
| GB (1) | GB1361199A (en) |
| NL (1) | NL7114737A (en) |
-
1971
- 1971-10-16 DE DE19712151560 patent/DE2151560A1/en active Pending
- 1971-10-26 BE BE774481A patent/BE774481A/en unknown
- 1971-10-26 FR FR7138372A patent/FR2113239A5/fr not_active Expired
- 1971-10-26 NL NL7114737A patent/NL7114737A/xx unknown
- 1971-10-27 GB GB4996471A patent/GB1361199A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2151560A1 (en) | 1972-05-04 |
| BE774481A (en) | 1972-04-26 |
| FR2113239A5 (en) | 1972-06-23 |
| NL7114737A (en) | 1972-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |