DE1795533A1 - Penicilline mit einer geschuetzten Aminogruppe,deren nichttoxische Salze und ihre Verwendung zur Herstellung weiterer Penicilline - Google Patents
Penicilline mit einer geschuetzten Aminogruppe,deren nichttoxische Salze und ihre Verwendung zur Herstellung weiterer PenicillineInfo
- Publication number
- DE1795533A1 DE1795533A1 DE19661795533 DE1795533A DE1795533A1 DE 1795533 A1 DE1795533 A1 DE 1795533A1 DE 19661795533 DE19661795533 DE 19661795533 DE 1795533 A DE1795533 A DE 1795533A DE 1795533 A1 DE1795533 A1 DE 1795533A1
- Authority
- DE
- Germany
- Prior art keywords
- penicillins
- production
- amino group
- protected amino
- toxic salts
- 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.)
- Pending
Links
- 229930182555 Penicillin Natural products 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 11
- 150000002960 penicillins Chemical class 0.000 title claims description 10
- 125000003277 amino group Chemical group 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 231100000252 nontoxic Toxicity 0.000 title description 7
- 230000003000 nontoxic effect Effects 0.000 title description 7
- 239000002253 acid Substances 0.000 claims description 5
- -1 heterocyclic radical Chemical class 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 description 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 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12138/65A GB1064893A (en) | 1965-03-23 | 1965-03-23 | Process for the preparation of penicillins |
| GB3047965 | 1965-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795533A1 true DE1795533A1 (de) | 1972-01-27 |
Family
ID=26248808
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661795533 Pending DE1795533A1 (de) | 1965-03-23 | 1966-03-21 | Penicilline mit einer geschuetzten Aminogruppe,deren nichttoxische Salze und ihre Verwendung zur Herstellung weiterer Penicilline |
| DE19661670063 Pending DE1670063A1 (de) | 1965-03-23 | 1966-03-21 | Verfahren zur Herstellung von Penicillinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670063 Pending DE1670063A1 (de) | 1965-03-23 | 1966-03-21 | Verfahren zur Herstellung von Penicillinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3553202A (enExample) |
| BE (1) | BE678304A (enExample) |
| BR (1) | BR6677772D0 (enExample) |
| CH (1) | CH473835A (enExample) |
| DE (2) | DE1795533A1 (enExample) |
| ES (1) | ES324454A1 (enExample) |
| FR (1) | FR1472473A (enExample) |
| GB (1) | GB1064893A (enExample) |
| NL (1) | NL6603463A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669978A (en) * | 1970-05-28 | 1972-06-13 | American Home Prod | Process for the production of semi-synthetic penicillin intermediate |
-
1965
- 1965-03-23 GB GB12138/65A patent/GB1064893A/en not_active Expired
-
1966
- 1966-03-11 BR BR177772/66A patent/BR6677772D0/pt unknown
- 1966-03-16 NL NL6603463A patent/NL6603463A/xx unknown
- 1966-03-21 CH CH405266A patent/CH473835A/de not_active IP Right Cessation
- 1966-03-21 ES ES0324454A patent/ES324454A1/es not_active Expired
- 1966-03-21 DE DE19661795533 patent/DE1795533A1/de active Pending
- 1966-03-21 DE DE19661670063 patent/DE1670063A1/de active Pending
- 1966-03-22 FR FR54405A patent/FR1472473A/fr not_active Expired
- 1966-03-23 BE BE678304D patent/BE678304A/xx unknown
-
1969
- 1969-05-22 US US828435A patent/US3553202A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6603463A (enExample) | 1966-09-26 |
| DE1670063A1 (de) | 1970-10-29 |
| FR1472473A (fr) | 1967-03-10 |
| GB1064893A (en) | 1967-04-12 |
| CH473835A (de) | 1969-06-15 |
| BE678304A (enExample) | 1966-09-23 |
| BR6677772D0 (pt) | 1973-09-11 |
| ES324454A1 (es) | 1967-02-01 |
| US3553202A (en) | 1971-01-05 |
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