GB1290787A - - Google Patents
Info
- Publication number
- GB1290787A GB1290787A GB1199570A GB1290787DA GB1290787A GB 1290787 A GB1290787 A GB 1290787A GB 1199570 A GB1199570 A GB 1199570A GB 1290787D A GB1290787D A GB 1290787DA GB 1290787 A GB1290787 A GB 1290787A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- tert
- penicillin
- acid
- 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
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000003277 amino group Chemical group 0.000 abstract 6
- -1 N-protected amino Chemical group 0.000 abstract 5
- 150000002960 penicillins Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 229940024606 amino acid Drugs 0.000 abstract 3
- 235000001014 amino acid Nutrition 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- XUXRXWLKUYPGMZ-UHFFFAOYSA-N 2-(tritylamino)acetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCC(=O)O)C1=CC=CC=C1 XUXRXWLKUYPGMZ-UHFFFAOYSA-N 0.000 abstract 1
- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 abstract 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 abstract 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- 229930182844 L-isoleucine Natural products 0.000 abstract 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- 229930195722 L-methionine Natural products 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- NFVNYBJCJGKVQK-ZDUSSCGKSA-N N-[(Tert-butoxy)carbonyl]-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)OC(C)(C)C)C(O)=O)=CNC2=C1 NFVNYBJCJGKVQK-ZDUSSCGKSA-N 0.000 abstract 1
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 abstract 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 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical compound CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 150000003862 amino acid derivatives Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229960005261 aspartic acid Drugs 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical group 0.000 abstract 1
- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 abstract 1
- VVNARYNBUJBXBK-UHFFFAOYSA-N chloromethyl 2-(tritylamino)acetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCC(=O)OCCl)C1=CC=CC=C1 VVNARYNBUJBXBK-UHFFFAOYSA-N 0.000 abstract 1
- VMNOUUZNLWEFQZ-UHFFFAOYSA-N chloromethyl 2-aminoacetate;4-methylbenzenesulfonic acid Chemical compound NCC(=O)OCCl.CC1=CC=C(S(O)(=O)=O)C=C1 VMNOUUZNLWEFQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- 229960004452 methionine Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- 235000008729 phenylalanine Nutrition 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1199570 | 1970-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1290787A true GB1290787A (enrdf_load_stackoverflow) | 1972-09-27 |
Family
ID=9996505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1199570A Expired GB1290787A (enrdf_load_stackoverflow) | 1970-03-12 | 1970-03-12 |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1290787A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5481011A (en) * | 1994-12-13 | 1996-01-02 | Bristol-Myers Squibb Company | Process for preparing N-protected amino acid α-halomethyl ketones and alcohols from N-protected amino acid esters |
-
1970
- 1970-03-12 GB GB1199570A patent/GB1290787A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5481011A (en) * | 1994-12-13 | 1996-01-02 | Bristol-Myers Squibb Company | Process for preparing N-protected amino acid α-halomethyl ketones and alcohols from N-protected amino acid esters |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |