RU2001114830A - Натриевая соль 3-(4-циннамил-1-пиперазинил)иминометила рифамицина SV и способ ее получения - Google Patents
Натриевая соль 3-(4-циннамил-1-пиперазинил)иминометила рифамицина SV и способ ее получения Download PDFInfo
- Publication number
- RU2001114830A RU2001114830A RU2001114830/04A RU2001114830A RU2001114830A RU 2001114830 A RU2001114830 A RU 2001114830A RU 2001114830/04 A RU2001114830/04 A RU 2001114830/04A RU 2001114830 A RU2001114830 A RU 2001114830A RU 2001114830 A RU2001114830 A RU 2001114830A
- Authority
- RU
- Russia
- Prior art keywords
- sodium salt
- cinnamyl
- piperazinyl
- rifamycin
- sodium
- Prior art date
Links
- 159000000000 sodium salts Chemical class 0.000 title claims abstract 10
- 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 title claims abstract 7
- 229940109171 rifamycin sv Drugs 0.000 title claims abstract 7
- 238000000034 method Methods 0.000 title claims abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- 235000010378 sodium ascorbate Nutrition 0.000 claims abstract 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims abstract 2
- 229960005055 sodium ascorbate Drugs 0.000 claims abstract 2
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- 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 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 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 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012442 inert solvent 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
- 229960001225 rifampicin Drugs 0.000 abstract 1
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound 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 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
- C07D498/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (4)
1. Натриевая соль 3-(4-циннамил-1-пиперазинил)-иминометила рифамицина SV с общей формулой
2. Способ получения натриевой соли 3-(4-циннамил-1-пиперазинил)-иминометила рифамицина SV по п.1, отличающийся тем, что 3-(4-циннамил-1-пиперазинил)-иминометила рифамицин SV подвергают реакции с эквимолярными количествами органического или неорганического основания, содержащего натрий, в водной среде или в среде органического растворителя, и в присутствии небольшого количества аскорбата натрия в качестве антиокислителя.
3. Способ получения натриевой соли по п.1, отличающийся тем, что натриевую соль 3-формилрифамицина SV, полученную в соответствии со способом, описанным в п.2, подвергают реакции с N1-амино-N4иннамилпиперазином в среде нейтрального растворителя при комнатной температуре.
4. Применение натриевой соли по п.1 для лечения заболеваний, вызванных бактериальными инфекциями.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG102897 | 1998-11-04 | ||
| BG102897A BG64021B1 (bg) | 1998-11-04 | 1998-11-04 | Натриева сол на 3-(4-цинамил-1-пиперазинил)-иминометил рифамицин и метод за получаването й |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2001114830A true RU2001114830A (ru) | 2003-07-10 |
Family
ID=3927599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2001114830/04A RU2001114830A (ru) | 1998-11-04 | 1999-11-03 | Натриевая соль 3-(4-циннамил-1-пиперазинил)иминометила рифамицина SV и способ ее получения |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6476036B1 (ru) |
| EP (1) | EP1124831B1 (ru) |
| AT (1) | ATE248176T1 (ru) |
| AU (1) | AU1020400A (ru) |
| BG (1) | BG64021B1 (ru) |
| BR (1) | BR9915035A (ru) |
| DE (1) | DE69910810T2 (ru) |
| DK (1) | DK1124831T3 (ru) |
| ES (1) | ES2207296T3 (ru) |
| PT (1) | PT1124831E (ru) |
| RU (1) | RU2001114830A (ru) |
| WO (1) | WO2000025721A2 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100383143C (zh) * | 2004-04-29 | 2008-04-23 | 薛荔 | 一锅烩合成利福平的方法 |
| WO2009137380A1 (en) * | 2008-05-05 | 2009-11-12 | Janssen Pharmaceutica Nv | 3-hydrazone piperazinyl rifamycin derivatives useful as antimicrobial agents |
| CA2881958C (en) * | 2012-08-13 | 2019-08-27 | Adipharm Ead | Pharmaceutical formulations containing 3-(4-cinnamyl-1-piperazinyl) amino derivatives of 3-formylrifamycin sv and 3-formylrifamycin s and a process of their preparation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR64108B (en) * | 1977-04-15 | 1980-01-24 | Dso Pharmachim | Method for the preparation of azomethine-derivatives of rifamycin s.v |
| SE458505B (sv) * | 1979-07-10 | 1989-04-10 | Lepetit Spa | Anvaendningen av rifamycin sv och salter daerav foer framstaellning av en beredning foer behandling av reumatoid artrit samt vissa av salterna och deras framstaellning |
| ATE47857T1 (de) * | 1985-10-18 | 1989-11-15 | Ciba Geigy Ag | Substituierte 4-benzyl-piperazinyl-verbindungen. |
| IT1202424B (it) * | 1987-01-26 | 1989-02-09 | Prodotti Antibiotici Spa | Sali di un derivato rifamicinico |
| EP0284552A1 (de) * | 1987-03-06 | 1988-09-28 | Ciba-Geigy Ag | 4-Benzyl-piperazinyl-Hydrazone |
| US5095108A (en) * | 1990-08-28 | 1992-03-10 | Technologichen Kombinat Za Promishlena Microbiologia | Non-solvated crystalline form "A" of 3-(4-cynnamyl-1-piperazinyl)iminomethylrifamycine SV and a method of its production |
-
1998
- 1998-11-04 BG BG102897A patent/BG64021B1/bg unknown
-
1999
- 1999-11-03 DK DK99953444T patent/DK1124831T3/da active
- 1999-11-03 RU RU2001114830/04A patent/RU2001114830A/ru not_active Application Discontinuation
- 1999-11-03 AT AT99953444T patent/ATE248176T1/de not_active IP Right Cessation
- 1999-11-03 ES ES99953444T patent/ES2207296T3/es not_active Expired - Lifetime
- 1999-11-03 PT PT99953444T patent/PT1124831E/pt unknown
- 1999-11-03 AU AU10204/00A patent/AU1020400A/en not_active Abandoned
- 1999-11-03 US US09/831,012 patent/US6476036B1/en not_active Expired - Fee Related
- 1999-11-03 EP EP99953444A patent/EP1124831B1/en not_active Expired - Lifetime
- 1999-11-03 WO PCT/BG1999/000022 patent/WO2000025721A2/en active IP Right Grant
- 1999-11-03 BR BR9915035-2A patent/BR9915035A/pt not_active Application Discontinuation
- 1999-11-03 DE DE69910810T patent/DE69910810T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU1020400A (en) | 2000-05-22 |
| BG64021B1 (bg) | 2003-10-31 |
| BG102897A (en) | 2000-06-30 |
| EP1124831B1 (en) | 2003-08-27 |
| DE69910810D1 (de) | 2003-10-02 |
| EP1124831A2 (en) | 2001-08-22 |
| WO2000025721A3 (en) | 2000-11-16 |
| WO2000025721A2 (en) | 2000-05-11 |
| BR9915035A (pt) | 2001-10-16 |
| DK1124831T3 (da) | 2003-12-22 |
| US6476036B1 (en) | 2002-11-05 |
| PT1124831E (pt) | 2004-01-30 |
| ATE248176T1 (de) | 2003-09-15 |
| ES2207296T3 (es) | 2004-05-16 |
| DE69910810T2 (de) | 2004-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA94 | Acknowledgement of application withdrawn (non-payment of fees) |
Effective date: 20050317 |