BG64021B1 - Натриева сол на 3-(4-цинамил-1-пиперазинил)-иминометил рифамицин и метод за получаването й - Google Patents
Натриева сол на 3-(4-цинамил-1-пиперазинил)-иминометил рифамицин и метод за получаването й Download PDFInfo
- Publication number
- BG64021B1 BG64021B1 BG102897A BG10289798A BG64021B1 BG 64021 B1 BG64021 B1 BG 64021B1 BG 102897 A BG102897 A BG 102897A BG 10289798 A BG10289798 A BG 10289798A BG 64021 B1 BG64021 B1 BG 64021B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- rifamycin
- sodium salt
- piperazinyl
- sodium
- cinnamyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 159000000000 sodium salts Chemical class 0.000 title claims abstract description 19
- 229930189077 Rifamycin Natural products 0.000 title claims abstract description 10
- 229960003292 rifamycin Drugs 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 235000010378 sodium ascorbate Nutrition 0.000 claims abstract description 8
- 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 description 8
- 229960005055 sodium ascorbate Drugs 0.000 claims abstract description 8
- 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 description 8
- 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 abstract description 5
- 229940109171 rifamycin sv Drugs 0.000 claims description 11
- 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 description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 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 description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 27
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 15
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 6
- 238000004821 distillation Methods 0.000 abstract description 3
- 239000012442 inert solvent Substances 0.000 abstract description 3
- 244000005700 microbiome Species 0.000 abstract description 3
- SBBBNYBCIOBABF-UHFFFAOYSA-N 4-(3-phenylprop-2-enyl)piperazin-1-amine Chemical compound C1CN(N)CCN1CC=CC1=CC=CC=C1 SBBBNYBCIOBABF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- YVOFSHPIJOYKSH-NLYBMVFSSA-M sodium rifomycin sv Chemical compound [Na+].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 YVOFSHPIJOYKSH-NLYBMVFSSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 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 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- -1 1-PIPERAZINYL-IMINOMETHYL Chemical class 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 201000006836 Miliary Tuberculosis Diseases 0.000 description 1
- 206010062207 Mycobacterial infection Diseases 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C07D498/02—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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG102897A BG64021B1 (bg) | 1998-11-04 | 1998-11-04 | Натриева сол на 3-(4-цинамил-1-пиперазинил)-иминометил рифамицин и метод за получаването й |
| BR9915035-2A BR9915035A (pt) | 1998-11-04 | 1999-11-03 | Sal de sódio de 3-(4-cinamil-1-piperazinil)iminometil rifamicina sv e processo de preparação |
| DK99953444T DK1124831T3 (da) | 1998-11-04 | 1999-11-03 | Natriumsalt af 3-(4-cinnamyl-1-piperazinyl)imino-methyl-rifamycin SV og fremgangsmåde til fremstilling heraf |
| ES99953444T ES2207296T3 (es) | 1998-11-04 | 1999-11-03 | Sal sodica de 3-(4-cinamil-1-piperazinil)imino-metil rifamicina sv y procedimiento de preparacion. |
| DE69910810T DE69910810T2 (de) | 1998-11-04 | 1999-11-03 | Natriumsalz von 3-(4-cinnamyl-1-piperazinyl)-iminomethyl-rifamycin sv und verfahren zu seiner herstellung |
| PCT/BG1999/000022 WO2000025721A2 (en) | 1998-11-04 | 1999-11-03 | Sodium salt of 3-(4-cinnamyl-1-piperazinyl)imino-methyl rifamycin sv and process of preparation |
| AU10204/00A AU1020400A (en) | 1998-11-04 | 1999-11-03 | Sodium salt of 3-(4-cinnamyl-1-piperazinyl)imino-methyl rifamycin sv and processof preparation |
| RU2001114830/04A RU2001114830A (ru) | 1998-11-04 | 1999-11-03 | Натриевая соль 3-(4-циннамил-1-пиперазинил)иминометила рифамицина SV и способ ее получения |
| AT99953444T ATE248176T1 (de) | 1998-11-04 | 1999-11-03 | Natriumsalz von 3-(4-cinnamyl-1-piperazinyl)- iminomethyl-rifamycin sv und verfahren zu seiner herstellung |
| US09/831,012 US6476036B1 (en) | 1998-11-04 | 1999-11-03 | Sodium salt of 3-(4-cinnamyl-1-piperazinyl)-imino-methyl rifamycin SV |
| EP99953444A EP1124831B1 (en) | 1998-11-04 | 1999-11-03 | Sodium salt of 3-(4-cinnamyl-1-piperazinyl)imino-methyl rifamycin sv and process of preparation |
| PT99953444T PT1124831E (pt) | 1998-11-04 | 1999-11-03 | Sal de sodio de 3-(4-cinamil-1-piperazinil)-iminometilrifamicina sv e processo de peparacao |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| BG102897A BG102897A (en) | 2000-06-30 |
| BG64021B1 true BG64021B1 (bg) | 2003-10-31 |
Family
ID=3927599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG102897A BG64021B1 (bg) | 1998-11-04 | 1998-11-04 | Натриева сол на 3-(4-цинамил-1-пиперазинил)-иминометил рифамицин и метод за получаването й |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6476036B1 (da) |
| EP (1) | EP1124831B1 (da) |
| AT (1) | ATE248176T1 (da) |
| AU (1) | AU1020400A (da) |
| BG (1) | BG64021B1 (da) |
| BR (1) | BR9915035A (da) |
| DE (1) | DE69910810T2 (da) |
| DK (1) | DK1124831T3 (da) |
| ES (1) | ES2207296T3 (da) |
| PT (1) | PT1124831E (da) |
| RU (1) | RU2001114830A (da) |
| WO (1) | WO2000025721A2 (da) |
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 |
| 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 |
| RU2001114830A (ru) | 2003-07-10 |
| DE69910810T2 (de) | 2004-08-19 |
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