NO751781L - - Google Patents
Info
- Publication number
- NO751781L NO751781L NO751781A NO751781A NO751781L NO 751781 L NO751781 L NO 751781L NO 751781 A NO751781 A NO 751781A NO 751781 A NO751781 A NO 751781A NO 751781 L NO751781 L NO 751781L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- compound
- groups
- inorganic
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 12
- 229930186147 Cephalosporin Natural products 0.000 claims abstract description 7
- 229940124587 cephalosporin Drugs 0.000 claims abstract description 7
- 150000001780 cephalosporins Chemical class 0.000 claims abstract description 7
- -1 cyano-methyl- Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000013067 intermediate product Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 150000002484 inorganic compounds Chemical class 0.000 claims 1
- 229910010272 inorganic material Inorganic materials 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- 238000012217 deletion Methods 0.000 abstract 1
- 230000037430 deletion Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 8
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 7
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- CIPQGGYPCPIDBB-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 CIPQGGYPCPIDBB-WPZCJLIBSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- BWVJONPOFKRJPP-FQNRMIAFSA-N methyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2SCC(C)=C(N2C1=O)C(=O)OC)NC(=O)COC1=CC=CC=C1 BWVJONPOFKRJPP-FQNRMIAFSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- RKPYPVYWRWYHKC-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)COC1=CC=CC=C1 RKPYPVYWRWYHKC-WPZCJLIBSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 125000005604 azodicarboxylate group Chemical group 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 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 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AIOBKJSZCKJHOA-UHFFFAOYSA-N azane;4-methylbenzenesulfonic acid;hydrate Chemical compound N.O.CC1=CC=C(S(O)(=O)=O)C=C1 AIOBKJSZCKJHOA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 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)
- Document Processing Apparatus (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23070/74A IT1043958B (it) | 1974-05-22 | 1974-05-22 | Procedimento per la preparazione di cefalosporine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751781L true NO751781L (nl) | 1975-11-25 |
Family
ID=11203454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751781A NO751781L (nl) | 1974-05-22 | 1975-05-20 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS50160291A (nl) |
| AT (1) | AT340047B (nl) |
| BE (1) | BE829304A (nl) |
| CA (1) | CA1055485A (nl) |
| DE (1) | DE2522142A1 (nl) |
| DK (1) | DK220375A (nl) |
| ES (1) | ES437842A1 (nl) |
| FR (1) | FR2279753A1 (nl) |
| GB (2) | GB1472865A (nl) |
| HU (1) | HU171357B (nl) |
| IT (1) | IT1043958B (nl) |
| NL (1) | NL170286C (nl) |
| NO (1) | NO751781L (nl) |
| SE (1) | SE7505751L (nl) |
| SU (1) | SU727147A3 (nl) |
| ZA (1) | ZA753244B (nl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1472866A (en) | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
| NL7806860A (nl) * | 1977-07-05 | 1979-01-09 | Farmaceutici Italia | Werkwijze voor het bereiden van met nocardicine verwan- te azetidinonen. |
| US4482491A (en) * | 1981-05-01 | 1984-11-13 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Thiazolinoazetidinone derivatives and process for the preparation of the same |
| EP0088488B1 (en) * | 1982-01-22 | 1986-10-01 | Beecham Group Plc | Antibacterial agents, their preparation and use |
-
1974
- 1974-05-22 IT IT23070/74A patent/IT1043958B/it active
-
1975
- 1975-05-16 AT AT376875A patent/AT340047B/de not_active IP Right Cessation
- 1975-05-16 NL NLAANVRAGE7505800,A patent/NL170286C/nl not_active IP Right Cessation
- 1975-05-17 DE DE19752522142 patent/DE2522142A1/de not_active Withdrawn
- 1975-05-20 GB GB2141975A patent/GB1472865A/en not_active Expired
- 1975-05-20 CA CA227,388A patent/CA1055485A/en not_active Expired
- 1975-05-20 DK DK220375A patent/DK220375A/da unknown
- 1975-05-20 ZA ZA00753244A patent/ZA753244B/xx unknown
- 1975-05-20 HU HU75SO00001145A patent/HU171357B/hu unknown
- 1975-05-20 JP JP50059355A patent/JPS50160291A/ja active Pending
- 1975-05-20 GB GB2841076A patent/GB1472870A/en not_active Expired
- 1975-05-20 FR FR7515596A patent/FR2279753A1/fr active Granted
- 1975-05-20 NO NO751781A patent/NO751781L/no unknown
- 1975-05-20 SE SE7505751A patent/SE7505751L/xx unknown
- 1975-05-21 ES ES437842A patent/ES437842A1/es not_active Expired
- 1975-05-21 SU SU752133714A patent/SU727147A3/ru active
- 1975-05-21 BE BE156546A patent/BE829304A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1472870A (en) | 1977-05-11 |
| AU8131975A (en) | 1976-11-25 |
| ES437842A1 (es) | 1977-01-01 |
| NL170286B (nl) | 1982-05-17 |
| FR2279753A1 (fr) | 1976-02-20 |
| NL7505800A (nl) | 1975-11-25 |
| IT1043958B (it) | 1980-02-29 |
| ATA376875A (de) | 1977-03-15 |
| SE7505751L (sv) | 1975-11-24 |
| HU171357B (hu) | 1977-12-28 |
| NL170286C (nl) | 1982-10-18 |
| GB1472865A (en) | 1977-05-11 |
| AT340047B (de) | 1977-11-25 |
| SU727147A3 (ru) | 1980-04-05 |
| DE2522142A1 (de) | 1975-12-11 |
| CA1055485A (en) | 1979-05-29 |
| ZA753244B (en) | 1976-05-26 |
| BE829304A (fr) | 1975-11-21 |
| DK220375A (da) | 1975-11-23 |
| JPS50160291A (nl) | 1975-12-25 |
| FR2279753B1 (nl) | 1979-03-16 |
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