NO116085B - - Google Patents

Info

Publication number: NO116085B
Authority: NO; Norway
Prior art keywords: penicillin; infrared spectrum; aminobenzylpenicillin; hydrated; temperature
Prior art date: 1963-06-22

Application number

NO15373664A

Other languages

English (en)

Norwegian (no)

Inventor

H Rapson

E Stove

Original Assignee

Beecham Group Ltd

Priority date (The priority date 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 date listed.)

1963-06-22

Filing date

1964-06-19

Publication date

1969-01-27

1964-06-19 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1969-01-27 Publication of NO116085B publication Critical patent/NO116085B/no

Links

AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 claims description 25
238000010438 heat treatment Methods 0.000 claims description 13
230000018044 dehydration Effects 0.000 claims description 10
238000006297 dehydration reaction Methods 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
239000007788 liquid Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
238000002329 infrared spectrum Methods 0.000 description 28
229930182555 Penicillin Natural products 0.000 description 24
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 23
229940049954 penicillin Drugs 0.000 description 23
239000000047 product Substances 0.000 description 19
238000001228 spectrum Methods 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
-1 aliphatic nitro compound Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO15373664A 1963-06-22 1964-06-19 NO116085B (da)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB2491963A GB1016875A (en)	1963-06-22	1963-06-22	ª‡-aminobenzyl penicillin
GB3505463		1963-09-05
GB3562663		1963-09-10

Publications (1)

Publication Number	Publication Date
NO116085B true NO116085B (da)	1969-01-27

Family

ID=27258379

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO15373664A NO116085B (da)	1963-06-22	1964-06-19

Country Status (13)

Country	Link
AT (1)	AT249867B (da)
BE (1)	BE649197A (da)
BR (1)	BR6459876D0 (da)
CH (1)	CH450430A (da)
DE (1)	DE1279021B (da)
DK (1)	DK106973C (da)
ES (1)	ES301096A1 (da)
FI (1)	FI44613C (da)
FR (1)	FR1406104A (da)
GB (1)	GB1016875A (da)
NL (2)	NL6406859A (da)
NO (1)	NO116085B (da)
SE (1)	SE313814B (da)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1207933B (de) *	1962-12-26	1965-12-30	American Home Prod	Verfahren zur Herstellung von kristallwasser-freiem D-alpha-Aminobenzylpenicillin

0
- NL NL123293D patent/NL123293C/xx active
1963
- 1963-06-22 GB GB2491963A patent/GB1016875A/en not_active Expired
1964
- 1964-06-10 BR BR15987664A patent/BR6459876D0/pt unknown
- 1964-06-12 BE BE649197D patent/BE649197A/xx unknown
- 1964-06-13 FI FI129164A patent/FI44613C/fi active
- 1964-06-15 DE DEB77261A patent/DE1279021B/de active Pending
- 1964-06-15 CH CH776964A patent/CH450430A/de unknown
- 1964-06-16 ES ES301096A patent/ES301096A1/es not_active Expired
- 1964-06-16 SE SE733764A patent/SE313814B/xx unknown
- 1964-06-17 NL NL6406859A patent/NL6406859A/xx unknown
- 1964-06-17 FR FR978598A patent/FR1406104A/fr not_active Expired
- 1964-06-18 DK DK306664A patent/DK106973C/da active
- 1964-06-19 AT AT526364A patent/AT249867B/de active
- 1964-06-19 NO NO15373664A patent/NO116085B/no unknown

Also Published As

Publication number	Publication date
ES301096A1 (es)	1964-12-01
SE313814B (da)	1969-08-25
DE1279021B (de)	1968-10-03
GB1016875A (en)	1966-01-12
NL6406859A (da)	1964-12-23
CH450430A (de)	1968-01-31
FI44613C (fi)	1974-05-13
FI44613B (da)	1971-08-31
FR1406104A (fr)	1965-07-16
AT249867B (de)	1966-10-10
BE649197A (da)	1964-10-01
DK106973C (da)	1967-04-10
BR6459876D0 (pt)	1973-08-14
NL123293C (da)

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