ES382809A1 - Procedure for the preparation of new antibiotics. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the preparation of new antibiotics. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES382809A1 ES382809A1 ES382809A ES382809A ES382809A1 ES 382809 A1 ES382809 A1 ES 382809A1 ES 382809 A ES382809 A ES 382809A ES 382809 A ES382809 A ES 382809A ES 382809 A1 ES382809 A1 ES 382809A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- formula
- lower alkyl
- nitro
- treatment
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 229910052736 halogen Inorganic materials 0.000 abstract 8
- 150000002367 halogens Chemical class 0.000 abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 8
- -1 nitro, amino Chemical group 0.000 abstract 8
- 239000003795 chemical substances by application Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 2
- 238000006297 dehydration reaction Methods 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catching Or Destruction (AREA)
- Fodder In General (AREA)
Abstract
Procedure for the preparation of new antibiotics of the formula **(See formula)** in which X is taken from the groups made up of **(See formula)** where R1 is taken from the group consisting of hydrogen, lower alkyl, phenyl, and phenyl substituted by a member of the group consisting of halogen, nitro, and lower alkyl; R2 is taken from the group consisting of hydrogen lower alkyl, lower alkanoyl, (see formula), benzoyl and benzoyl substituted by a member of the group consisting of halogen, nitro and lower alkyl; R3 is taken from the group consisting of hydrogen, halogen, nitro, amino, lower alkanoylamino, lower alkylamino, phenylazo and phenylazo substituted by a member of the group consisting of halogen, nitro, lower alkyl and lower alkoxy; and R4 is taken from the group consisting of -OH, = O and = N-OH, provided that at least one of the symbols R1, R2 and R3 is other than hydrogen or R4 is other than = O; dehydration products of the compounds of formula V, in which X represents group (a) and R4 is = O; and of pharmaceutically acceptable salts of those of said compounds which are acidic, procedure comprising subjecting a compound of the formula **(See formula)** or a respective pharmaceutically acceptable salt, in the order of succession desired, to one or more of the following procedural steps; (l) treatment with an esterifying agent to obtain an ester group R1; (2) treatment with a lower alkylating agent, to form a compound of formula V in which R1 and/or R2 are lower alkyl; (3) treatment with an agent giving a member of the lower alkanoyl groups (see formula), benzoyl and benzoyl substituted by a member of the group consisting of halogen, nitro and lower alkyl, to form a compound of formula V in which R2 has the respective meaning; (4) treatment with a halogenating agent, to form a compound of formula V, wherein R3 is halogen; (5) treatment with a nitrating agent, to form a compound of formula V, in which it is nitro; (6) treatment with a diazonic salt of a compound chosen from aniline and aniline substituted by a member of the group consisting of halogen, nitro, lower alkyl and lower alkoxy, to form a compound of formula Y, in which R3 is taking the group consisting of phenylazo and phenylazo substituted by a member taken from the group consisting of halogen, nitro, lower alkyl and lower alkoxy; and (7) treatment with an acid addition salt of the hydroxylamine, to form a compound of formula V, where R4 is hydroxyimino, or reduction to form a compound of formula V where R4 is hydroxy, or treatment with a dehitrating agent to form a respective dehydration product; after which, if desired, a nitro group present is reduced to an amine group or, in the presence of a lower alkyl aldehyde, to a lower alkylamine group; if desired, the thus formed amine group is subjected to lower alkylation or lower alkanzylation or is converted to a diazo group by treatment with nitrous acid or a lower alkyl nitrite; and, if desired, an acid of the formula Y obtained is converted into a respective pharmaceutically acceptable salt. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85104469A | 1969-08-18 | 1969-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES382809A1 true ES382809A1 (en) | 1972-12-16 |
Family
ID=25309816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES382809A Expired ES382809A1 (en) | 1969-08-18 | 1970-08-17 | Procedure for the preparation of new antibiotics. (Machine-translation by Google Translate, not legally binding) |
Country Status (17)
| Country | Link |
|---|---|
| JP (4) | JPS4815942B1 (en) |
| BR (1) | BR7021444D0 (en) |
| CA (1) | CA941822A (en) |
| CS (1) | CS161114B2 (en) |
| DK (1) | DK127782B (en) |
| ES (1) | ES382809A1 (en) |
| FI (1) | FI52582C (en) |
| IE (1) | IE34611B1 (en) |
| IL (1) | IL35000A (en) |
| MY (1) | MY7300484A (en) |
| NO (1) | NO128767B (en) |
| PL (1) | PL80959B1 (en) |
| RO (1) | RO56804A (en) |
| SE (1) | SE375999B (en) |
| SU (1) | SU406349A3 (en) |
| YU (1) | YU34893B (en) |
| ZA (1) | ZA704939B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5340248U (en) * | 1976-09-10 | 1978-04-07 |
-
1970
- 1970-07-17 ZA ZA704939A patent/ZA704939B/en unknown
- 1970-07-27 IL IL35000A patent/IL35000A/en unknown
- 1970-07-31 CA CA89689A patent/CA941822A/en not_active Expired
- 1970-08-10 IE IE1037/70A patent/IE34611B1/en unknown
- 1970-08-14 YU YU2071/70A patent/YU34893B/en unknown
- 1970-08-14 SE SE7011155A patent/SE375999B/xx unknown
- 1970-08-17 DK DK420870AA patent/DK127782B/en unknown
- 1970-08-17 ES ES382809A patent/ES382809A1/en not_active Expired
- 1970-08-17 NO NO03125/70A patent/NO128767B/no unknown
- 1970-08-17 BR BR221444/70A patent/BR7021444D0/en unknown
- 1970-08-17 SU SU1476723A patent/SU406349A3/ru active
- 1970-08-17 CS CS5681A patent/CS161114B2/cs unknown
- 1970-08-18 FI FI702263A patent/FI52582C/en not_active IP Right Cessation
- 1970-08-18 JP JP45072305A patent/JPS4815942B1/ja active Pending
- 1970-08-18 PL PL1970142758A patent/PL80959B1/pl unknown
- 1970-08-18 RO RO64257A patent/RO56804A/ro unknown
-
1971
- 1971-12-28 JP JP47004105A patent/JPS515444B1/ja active Pending
- 1971-12-28 JP JP47004104A patent/JPS4816507B1/ja active Pending
- 1971-12-28 JP JP47004103A patent/JPS4816506B1/ja active Pending
-
1973
- 1973-12-30 MY MY484/73A patent/MY7300484A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU207170A (en) | 1979-10-31 |
| JPS4815942B1 (en) | 1973-05-18 |
| MY7300484A (en) | 1973-12-31 |
| SU406349A3 (en) | 1973-11-05 |
| PL80959B1 (en) | 1975-08-30 |
| FI52582C (en) | 1977-10-10 |
| IL35000A (en) | 1974-01-14 |
| JPS4816506B1 (en) | 1973-05-22 |
| IL35000A0 (en) | 1970-09-17 |
| DK127782B (en) | 1974-01-07 |
| CS161114B2 (en) | 1975-05-04 |
| CA941822A (en) | 1974-02-12 |
| SE375999B (en) | 1975-05-05 |
| YU34893B (en) | 1980-04-30 |
| IE34611L (en) | 1971-02-18 |
| ZA704939B (en) | 1971-04-28 |
| JPS515444B1 (en) | 1976-02-20 |
| IE34611B1 (en) | 1975-06-25 |
| JPS4816507B1 (en) | 1973-05-22 |
| RO56804A (en) | 1974-07-01 |
| FI52582B (en) | 1977-06-30 |
| BR7021444D0 (en) | 1973-03-07 |
| NO128767B (en) | 1974-01-07 |
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