NO120734B - - Google Patents

Download PDF

Info

Publication number: NO120734B
Authority: NO; Norway
Prior art keywords: rifamycin; lower alkyl; methanol; hours; derivatives
Prior art date: 1967-03-01

Application number

NO0696/68A

Other languages

English (en)

Norwegian (no)

Inventor

N Maggi

Original Assignee

Lepetit Spa

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.)

1967-03-01

Filing date

1968-02-26

Publication date

1970-11-30

1968-02-26 Application filed by Lepetit Spa filed Critical Lepetit Spa

1970-11-30 Publication of NO120734B publication Critical patent/NO120734B/no

Links

150000001875 compounds Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims description 7
BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 claims description 6
BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 5
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
-1 3-methylaminocrotonic acid dimethylamide Chemical compound 0.000 description 1
206010007882 Cellulitis Diseases 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010017553 Furuncle Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010031252 Osteomyelitis Diseases 0.000 description 1
208000005141 Otitis Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
229930189077 Rifamycin Natural products 0.000 description 1
HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
206010000269 abscess Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
201000001352 cholecystitis Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
QAKYFFYZPIPLDN-PLNGDYQASA-N methyl (z)-3-(methylamino)but-2-enoate Chemical compound CN\C(C)=C/C(=O)OC QAKYFFYZPIPLDN-PLNGDYQASA-N 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 1
229940109171 rifamycin sv Drugs 0.000 description 1
229940081192 rifamycins Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

NO0696/68A 1967-03-01 1968-02-26 NO120734B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB9755/67A GB1172155A (en)	1967-03-01	1967-03-01	New Rifamycins

Publications (1)

Publication Number	Publication Date
NO120734B true NO120734B (da)	1970-11-30

Family

ID=9878162

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO0696/68A NO120734B (da)	1967-03-01	1968-02-26

Country Status (14)

Country	Link
US (1)	US3625961A (da)
BE (1)	BE711546A (da)
CH (1)	CH482716A (da)
DE (1)	DE1695384A1 (da)
DK (1)	DK129198B (da)
ES (1)	ES351070A1 (da)
FI (1)	FI48275C (da)
FR (2)	FR1562297A (da)
GB (1)	GB1172155A (da)
IL (1)	IL29441A (da)
NL (1)	NL6802429A (da)
NO (1)	NO120734B (da)
SE (1)	SE337829B (da)
YU (1)	YU31945B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1523199A (en) *	1976-05-28	1978-08-31	Lepetit Spa	Rifamycin sv derivatives
GB1523198A (en) *	1976-05-28	1978-08-31	Lepetit Spa	Thiazolo-rifamycin derivatives
DD204925A5 (de) *	1980-09-25	1983-12-14	Ciba Geigy Ag	Verfahren zur herstellung eines 4-aminoimidazolo (4,5-c)rifamycins sv oder s

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1090115A (en) *	1964-04-02	1967-11-08	Lepetit Spa	Mannich bases of rifamycin sv

1967
- 1967-03-01 GB GB9755/67A patent/GB1172155A/en not_active Expired
1968
- 1968-02-05 US US702796A patent/US3625961A/en not_active Expired - Lifetime
- 1968-02-08 IL IL29441A patent/IL29441A/en unknown
- 1968-02-17 DE DE19681695384 patent/DE1695384A1/de not_active Withdrawn
- 1968-02-20 NL NL6802429A patent/NL6802429A/xx unknown
- 1968-02-23 FI FI680478A patent/FI48275C/fi active
- 1968-02-23 CH CH265968A patent/CH482716A/fr not_active IP Right Cessation
- 1968-02-26 NO NO0696/68A patent/NO120734B/no unknown
- 1968-02-28 SE SE02567/68A patent/SE337829B/xx unknown
- 1968-02-28 DK DK78568AA patent/DK129198B/da not_active IP Right Cessation
- 1968-02-29 ES ES351070A patent/ES351070A1/es not_active Expired
- 1968-03-01 YU YU0486/68A patent/YU31945B/xx unknown
- 1968-03-01 BE BE711546D patent/BE711546A/xx not_active IP Right Cessation
- 1968-03-01 FR FR1562297D patent/FR1562297A/fr not_active Expired
- 1968-05-28 FR FR153157A patent/FR7891M/fr not_active Expired

Also Published As

Publication number	Publication date
YU31945B (en)	1974-02-28
US3625961A (en)	1971-12-07
BE711546A (da)	1968-07-15
FI48275C (fi)	1974-08-12
DE1695384A1 (de)	1972-04-13
IL29441A (en)	1971-05-26
NL6802429A (da)	1968-09-02
FR1562297A (da)	1969-04-04
FR7891M (da)	1970-05-04
CH482716A (fr)	1969-12-15
DK129198B (da)	1974-09-09
DK129198C (da)	1975-03-03
FI48275B (da)	1974-04-30
YU48668A (en)	1973-08-31
SE337829B (da)	1971-08-23
ES351070A1 (es)	1969-06-01
GB1172155A (en)	1969-11-26

Publication	Publication Date	Title
EP0009425B1 (en)	1982-01-27	Novel naphtyridine derivatives and pharmaceutical compositions containing them
US3165531A (en)	1965-01-12	13-substituted-6-deoxytetracyclines and process utilizing the same
IE51204B1 (en)	1986-10-29	Imidazo-rifamycin derivatives
Agui et al.	1977	Studies on quinoline derivatives and related compounds. 5. Synthesis and antimicrobial activity of novel 1-alkoxy-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acids
MXPA06001645A (es)	2006-05-12	Isotiazoloquinolonas y compuestos relacionados como agentes anti-infecciosos.
US4105778A (en)	1978-08-08	Fused γ-pyrone-2-carboxylic acid derivatives and process therefor
Chen et al.	1987	Structure-activity relationships of 6-(heterocyclyl) methylene penam sulfones; a new class of β-lactamase inhibitors
Gan-Jun et al.	2014	Anti-methicillin-resistant Staphylococcus aureus assay of azalomycin F5a and its derivatives
Tatsuta et al.	1997	The Total Synthesis of a Glycosidase Inhibitor, Nagstatin.
CN112500381B (zh)	2023-04-28	去氢中美菊素c衍生物及其制备方法和用途
CA1293503C (en)	1991-12-24	Substituted benzoxazinorifamycin derivative, process for preparing the same and antibacterial agent containing the same
NO120734B (da)	1970-11-30
US4108998A (en)	1978-08-22	Furo[3,4-b]quinoline derivatives and pharmaceutical compositions and methods employing them
US2585436A (en)	1952-02-12	Penicillin salts of amines derived from rosin
UHR et al.	1985	The Structure of Acetomycin Spectroscopic Characterization and X-Ray Analysis of a Bromo Derivative
US3678051A (en)	1972-07-18	Derivatives of 1,6-phenazinediol 5,10-dioxide
EP0203795B1 (en)	1992-07-29	Benzo [i,j] quinolizine-2-carboxylic acid derivatives, the salts and their hydrates, pharmaceutical compositions thereof, and process for preparing the same
US3681331A (en)	1972-08-01	1-hydroxy-6-amino alkoxy-phenazine 5,10-dioxides
ZA200400208B (en)	2005-06-29	Lactone formulations and method of use
US3700679A (en)	1972-10-24	Nuclear substituted derivatives of 1-hydroxy-6-methoxyphenazine 5,10-dioxide
US4372961A (en)	1983-02-08	Derivatives of rifamycins, their preparation and pharmaceutical compositions thereof
US4880825A (en)	1989-11-14	Mitomycin derivatives
CA1250846A (en)	1989-03-07	6-fluoro-1,4-dihydro-4-oxo-7-(4-pyridyl)-1,8- naphthyridine-3 carboxylic acid compounds
US3937707A (en)	1976-02-10	6-substituted 1-phenazinol 5,10-dioxide derivatives
EP1124831B1 (en)	2003-08-27	Sodium salt of 3-(4-cinnamyl-1-piperazinyl)imino-methyl rifamycin sv and process of preparation