GB1271018A - Novel derivatives of thiazine carboxylic acid and processes for their preparation - Google Patents
Novel derivatives of thiazine carboxylic acid and processes for their preparationInfo
- Publication number
- GB1271018A GB1271018A GB47790/71A GB4779071A GB1271018A GB 1271018 A GB1271018 A GB 1271018A GB 47790/71 A GB47790/71 A GB 47790/71A GB 4779071 A GB4779071 A GB 4779071A GB 1271018 A GB1271018 A GB 1271018A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiazine
- aminomethyl
- lactams
- dihydro
- carboxylic acids
- 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
- BNNNRTHFDVJELR-UHFFFAOYSA-N 2h-thiazine-3-carboxylic acid Chemical class OC(=O)C1=CC=CSN1 BNNNRTHFDVJELR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000003953 γ-lactams Chemical class 0.000 abstract 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- CUQQLFJBWDBZAF-UHFFFAOYSA-N pyrrolo[2,3-e]thiazine Chemical class S1N=CC=C2N=CC=C21 CUQQLFJBWDBZAF-UHFFFAOYSA-N 0.000 abstract 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002081 enamines Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 238000005866 tritylation reaction Methods 0.000 abstract 1
Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H9/00—Details of switching devices, not covered by groups H01H1/00 - H01H7/00
- H01H9/18—Distinguishing marks on switches, e.g. for indicating switch location in the dark; Adaptation of switches to receive distinguishing marks
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/08—Preparation by forming the ring or condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V17/00—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages
- F21V17/10—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening
- F21V17/16—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening by deformation of parts; Snap action mounting
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H13/00—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch
- H01H13/50—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member
- H01H13/52—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member the contact returning to its original state immediately upon removal of operating force, e.g. bell-push switch
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Theoretical Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,271,018. Pyrrolo - thiazine derivatives. ROUSSEL-UCLAF. 27 June, 1969 [27 June, 1968], No. 47790/71. Divided out of 1,271,013. Heading C2C. The invention comprises novel threo or erythro (or mixtures thereof) pyrrolo-thiazine derivatives of the formulµ in which R<SP>1</SP> is H or unsubstituted or substituted aryl, R is alkyl or aralkyl and Y is imido or acylamino, and the preparation thereof. The γ- lactams of 2-(α-R-oxycarbonyl-α-γ-methyl)-5- aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4- carboxylic acids (VIII) are obtained by reacting the corresponding 1-R<SP>1</SP>-2,3-dioxo-4-mercaptomethylpyrrolidines with enamines of the formula The γ-lactams of 2-(α-R-oxycarbonyl-α-aminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3- thiazine-4-carboxylic acids (VIIIa) are prepared by reacting compounds of Formula VIII above with hydrazine or subjecting said compounds to acid hydrolysis or hydrogenolysis. Hydrolysis of the resulting compounds gives the γ- lactams of 2 - (α - carboxy - α - aminomethyl)- 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine- 4-carboxylic acids (IX) which on reaction with a tritylation agent give the γ-lactams of 2-(α- carboxy - α - tritylaminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4 - carboxylic acids (IXa). The three isomers of the latter compound may be obtained by isomerization of the erythro isomers by treatment with alkaline reagents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR156898 | 1968-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1271018A true GB1271018A (en) | 1972-04-19 |
Family
ID=8651750
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47787/71A Expired GB1271015A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine carboxylic acids, esters thereof and processes for their preparation |
| GB47789/71A Expired GB1271017A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine derivatives, and processes for their preparation |
| GB47790/71A Expired GB1271018A (en) | 1968-06-27 | 1969-06-27 | Novel derivatives of thiazine carboxylic acid and processes for their preparation |
| GB32567/69A Expired GB1271013A (en) | 1968-06-27 | 1969-06-27 | Novel cephalosporin derivatives, and processes for their preparation |
| GB47788/71A Expired GB1271016A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine derivatives, and processes for their preparation |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47787/71A Expired GB1271015A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine carboxylic acids, esters thereof and processes for their preparation |
| GB47789/71A Expired GB1271017A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine derivatives, and processes for their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32567/69A Expired GB1271013A (en) | 1968-06-27 | 1969-06-27 | Novel cephalosporin derivatives, and processes for their preparation |
| GB47788/71A Expired GB1271016A (en) | 1968-06-27 | 1969-06-27 | Novel pyrrolidine derivatives, and processes for their preparation |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS5028440B1 (en) |
| AT (2) | AT293614B (en) |
| BE (1) | BE735127A (en) |
| BR (3) | BR6910251D0 (en) |
| CH (3) | CH522635A (en) |
| DE (4) | DE1932498A1 (en) |
| ES (2) | ES368820A1 (en) |
| FR (1) | FR1584569A (en) |
| GB (5) | GB1271015A (en) |
| HU (1) | HU162644B (en) |
| IL (1) | IL32379A (en) |
| NL (2) | NL142691B (en) |
| PL (1) | PL79142B1 (en) |
| SU (2) | SU495841A3 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0277215A1 (en) * | 1986-08-19 | 1988-08-10 | Horst Forschner | Do-it-yourself garments and set of components of do-it-yourself garments |
| EA013864B1 (en) * | 2008-08-29 | 2010-08-30 | Лимонова, Анастасия Викторовна | Method of enhancement antimicrobal activity of cephalosporin antibiotics |
-
1968
- 1968-06-27 FR FR156898A patent/FR1584569A/fr not_active Expired
-
1969
- 1969-06-11 IL IL32379A patent/IL32379A/en unknown
- 1969-06-13 PL PL1969134161A patent/PL79142B1/en unknown
- 1969-06-24 CH CH14171A patent/CH522635A/en not_active IP Right Cessation
- 1969-06-24 CH CH968169A patent/CH513206A/en not_active IP Right Cessation
- 1969-06-24 CH CH968069A patent/CH515276A/en not_active IP Right Cessation
- 1969-06-25 SU SU1343897A patent/SU495841A3/en active
- 1969-06-25 SU SU1340776A patent/SU384232A3/ru active
- 1969-06-25 HU HURO582A patent/HU162644B/hu unknown
- 1969-06-25 BE BE735127D patent/BE735127A/xx unknown
- 1969-06-26 NL NL696909849A patent/NL142691B/en not_active IP Right Cessation
- 1969-06-26 ES ES368820A patent/ES368820A1/en not_active Expired
- 1969-06-26 NL NL696909850A patent/NL142415B/en not_active IP Right Cessation
- 1969-06-26 DE DE19691932498 patent/DE1932498A1/en not_active Withdrawn
- 1969-06-26 DE DE19691966204 patent/DE1966204A1/en active Pending
- 1969-06-26 DE DE1966203A patent/DE1966203C3/en not_active Expired
- 1969-06-26 DE DE1967030A patent/DE1967030C3/en not_active Expired
- 1969-06-27 AT AT618469A patent/AT293614B/en not_active IP Right Cessation
- 1969-06-27 GB GB47787/71A patent/GB1271015A/en not_active Expired
- 1969-06-27 AT AT618569A patent/AT293615B/en not_active IP Right Cessation
- 1969-06-27 JP JP44050289A patent/JPS5028440B1/ja active Pending
- 1969-06-27 BR BR210251/69A patent/BR6910251D0/en unknown
- 1969-06-27 GB GB47789/71A patent/GB1271017A/en not_active Expired
- 1969-06-27 GB GB47790/71A patent/GB1271018A/en not_active Expired
- 1969-06-27 BR BR210250/69A patent/BR6910250D0/en unknown
- 1969-06-27 GB GB32567/69A patent/GB1271013A/en not_active Expired
- 1969-06-27 GB GB47788/71A patent/GB1271016A/en not_active Expired
- 1969-06-27 JP JP44050288A patent/JPS4934999B1/ja active Pending
- 1969-06-27 BR BR210252/69A patent/BR6910252D0/en unknown
-
1971
- 1971-09-17 ES ES395175A patent/ES395175A2/en not_active Expired
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