IL41926A - 3-formylrifamycin azines - Google Patents
3-formylrifamycin azinesInfo
- Publication number
- IL41926A IL41926A IL41926A IL4192673A IL41926A IL 41926 A IL41926 A IL 41926A IL 41926 A IL41926 A IL 41926A IL 4192673 A IL4192673 A IL 4192673A IL 41926 A IL41926 A IL 41926A
- Authority
- IL
- Israel
- Prior art keywords
- rifamycin
- derivatives
- hexahydro
- divalent
- formylrifamycin
- Prior art date
Links
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(C=O)=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 BBNQHOMJRFAQBN-UPZFVJMDSA-N 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 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 abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract 4
- -1 cycloaliphatic Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 229930189077 Rifamycin Natural products 0.000 claims abstract 2
- 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 claims abstract 2
- 238000009835 boiling Methods 0.000 claims abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract 2
- 229960003292 rifamycin Drugs 0.000 claims abstract 2
- 229940109171 rifamycin sv Drugs 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims 1
- 229930195573 Amycin Natural products 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 abstract 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
- C07D498/22—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 four or more hetero rings
-
- 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
- C07D498/02—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 two hetero rings
- C07D498/08—Bridged systems
-
- 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)
Abstract
1392272 Rifamycin derivatives GRUPPO LEPETIT SpA 29 March 1973 [31 May 1972] 15l91/ Heading C2C Derivatives of rifamycin SV having the general formula and 16, 17, 18, 19, 28 and 29 hexahydro and 25-desacetyl derivatives thereof wherein the symbol Rifa represents the rifamycin radical of formula and A represents (1) a direct bond connecting the two nitrogen atoms ; (2) a group wherein y is -CO-, -CNH-, -CS-, -SO 2 -, a divalent, aliphatic, cycloaliphatic, aromatic, araliphatic, or heterocyclic radical; R 2 and R 3 indedendently represent hydrogen, alkyl or taken together represent an aliphatic divalent chain of 1-4 carbon atoms connecting the two terminal nitrogen atoms, or (3) a divalent group wherein X represents a direct bond between the two carbon atoms, a divalent aliphatic, cycloaliphatic, aromatic, or heterocyclic radical, R and R 1 may be independently hydrogen, alkyl, cycloalkyl, aryl, heterocyclic or taken together represent an aliphatic chain of 1 to 8 C atoms connecting the two terminal carbon atoms, may be prepared by reacting 3-formylrifamycin SV or its 25-desacetyl or 16, 17, 18, 19, 28 and 29 hexahydro derivative with a hydrazine compound of the formula H 2 N-A-NH 2 in an inert organic solvent at a temperature ranging from room temperature to the boiling temperature of the solvent. Compounds prepared include 3-formylrifamycin SV azine, 16, 17, 18, 19, 28, 29 - hexahydro - 3 - formylrifamycin SV azine and 1,4-piperazinylidene-bis-(3,3<SP>1</SP>-iminomethyl rifamycin SV). Pharmaceutical compositions having antibacterial and anti-tumour activity comprise the above derivatives of rifamycin SV and a pharmaceutically acceptable carrier.
[GB1392272A]
Claims (1)
1. C L A S 1 Derivatives of the of the general I 28 snd their and 29 hexahydro derivatives a direct bond connecting the two nitrogen a wherein y is a divalent alkyl rad of 1 to 4 carbon atoms and taken together and stand for a divalent alkyl radical of 1 to 4 carbon i a divalent group wherein x is a direct bond connecting the tvo carbon atoms and R and are A process for preparing derivatives of the rifamycin of the general formula I and their and and 29 hexahydro as defined and claimed in Claim vhich comprises reacting rifamycin SV and its or and 28 hexahydro derivative with a hydrazine compound of the formula wherein A has the same meaning as before solvent in an inert a temperature ranging the room temperature and the boiling temperature of the A compound as claimed claim 1 which is SV A compound as in Claim 1 which is amycin SV A compound as in claim 1 which is cin April 1973 insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2507572 | 1972-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41926A0 IL41926A0 (en) | 1973-06-29 |
| IL41926A true IL41926A (en) | 1976-04-30 |
Family
ID=11215624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41926A IL41926A (en) | 1972-05-31 | 1973-04-02 | 3-formylrifamycin azines |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS516679B2 (en) |
| AR (2) | AR198663A1 (en) |
| AT (1) | AT323885B (en) |
| BE (1) | BE800276A (en) |
| CA (1) | CA992961A (en) |
| CH (1) | CH573433A5 (en) |
| DD (1) | DD107285A5 (en) |
| DE (1) | DE2326698A1 (en) |
| ES (1) | ES414894A1 (en) |
| FR (1) | FR2186231B1 (en) |
| GB (1) | GB1392272A (en) |
| HU (1) | HU167317B (en) |
| IE (1) | IE37481B1 (en) |
| IL (1) | IL41926A (en) |
| LU (1) | LU67695A1 (en) |
| NL (1) | NL154510B (en) |
| PL (1) | PL87112B1 (en) |
| RO (1) | RO65182A (en) |
| SE (1) | SE386444B (en) |
| SU (1) | SU514572A3 (en) |
| ZA (1) | ZA732293B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1478563A (en) * | 1975-03-05 | 1977-07-06 | Lepetit Spa | Rifamycin derivatives |
-
1973
- 1973-03-29 GB GB1519173A patent/GB1392272A/en not_active Expired
- 1973-03-30 IE IE508/73A patent/IE37481B1/en unknown
- 1973-04-02 IL IL41926A patent/IL41926A/en unknown
- 1973-04-03 ZA ZA732293A patent/ZA732293B/en unknown
- 1973-05-08 AR AR247892A patent/AR198663A1/en active
- 1973-05-11 CA CA171,060A patent/CA992961A/en not_active Expired
- 1973-05-18 ES ES414894A patent/ES414894A1/en not_active Expired
- 1973-05-25 DE DE2326698A patent/DE2326698A1/en active Pending
- 1973-05-25 NL NL737307319A patent/NL154510B/en not_active IP Right Cessation
- 1973-05-29 FR FR7319518A patent/FR2186231B1/fr not_active Expired
- 1973-05-29 SE SE7307611*A patent/SE386444B/en unknown
- 1973-05-29 LU LU67695A patent/LU67695A1/xx unknown
- 1973-05-29 RO RO7374946A patent/RO65182A/en unknown
- 1973-05-29 SU SU1920394A patent/SU514572A3/en active
- 1973-05-29 JP JP48059434A patent/JPS516679B2/ja not_active Expired
- 1973-05-29 AT AT468173A patent/AT323885B/en not_active IP Right Cessation
- 1973-05-29 DD DD171159A patent/DD107285A5/xx unknown
- 1973-05-30 BE BE131720A patent/BE800276A/en unknown
- 1973-05-30 HU HULE706A patent/HU167317B/hu unknown
- 1973-05-30 PL PL1973162950A patent/PL87112B1/pl unknown
- 1973-05-30 CH CH783173A patent/CH573433A5/xx not_active IP Right Cessation
- 1973-12-19 AR AR251497A patent/AR198715A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IE37481B1 (en) | 1977-08-03 |
| NL154510B (en) | 1977-09-15 |
| PL87112B1 (en) | 1976-06-30 |
| DD107285A5 (en) | 1974-07-20 |
| IL41926A0 (en) | 1973-06-29 |
| CA992961A (en) | 1976-07-13 |
| RO65182A (en) | 1981-05-30 |
| NL7307319A (en) | 1973-12-04 |
| SU514572A3 (en) | 1976-05-15 |
| JPS516679B2 (en) | 1976-03-01 |
| ZA732293B (en) | 1974-02-27 |
| AR198715A1 (en) | 1974-07-15 |
| SE386444B (en) | 1976-08-09 |
| LU67695A1 (en) | 1973-08-02 |
| GB1392272A (en) | 1975-04-30 |
| ES414894A1 (en) | 1976-02-01 |
| FR2186231B1 (en) | 1976-03-05 |
| IE37481L (en) | 1973-11-30 |
| JPS4942698A (en) | 1974-04-22 |
| BE800276A (en) | 1973-09-17 |
| AT323885B (en) | 1975-08-11 |
| DE2326698A1 (en) | 1973-12-13 |
| FR2186231A1 (en) | 1974-01-11 |
| AR198663A1 (en) | 1974-07-15 |
| HU167317B (en) | 1975-09-27 |
| AU5616173A (en) | 1974-11-28 |
| CH573433A5 (en) | 1976-03-15 |
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