JPH0114238B2 - - Google Patents
Info
- Publication number
- JPH0114238B2 JPH0114238B2 JP53077063A JP7706378A JPH0114238B2 JP H0114238 B2 JPH0114238 B2 JP H0114238B2 JP 53077063 A JP53077063 A JP 53077063A JP 7706378 A JP7706378 A JP 7706378A JP H0114238 B2 JPH0114238 B2 JP H0114238B2
- Authority
- JP
- Japan
- Prior art keywords
- compounds
- compound
- rifamycin
- formula
- group
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 rifamycin compound Chemical class 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000001663 electronic absorption spectrum Methods 0.000 description 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 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 229930189077 Rifamycin Natural products 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229960003292 rifamycin Drugs 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 201000008827 tuberculosis Diseases 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QBRFPWPICDILII-WVKYYCEASA-N 3-amino-4-iminorifamycin-s Chemical compound O=C1C(C(O)=C2C)=C3C(N)=C(N)C1=NC(=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 QBRFPWPICDILII-WVKYYCEASA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- OCNWYKFGWLGNHZ-UHFFFAOYSA-N 1-butylpiperidin-4-one Chemical compound CCCCN1CCC(=O)CC1 OCNWYKFGWLGNHZ-UHFFFAOYSA-N 0.000 description 1
- NUPCXPOFGHXLIZ-UHFFFAOYSA-N 1-hexylpiperidin-4-one Chemical compound CCCCCCN1CCC(=O)CC1 NUPCXPOFGHXLIZ-UHFFFAOYSA-N 0.000 description 1
- GTEUDVZENMLOPB-UHFFFAOYSA-N 1-pentylpiperidin-4-one Chemical compound CCCCCN1CCC(=O)CC1 GTEUDVZENMLOPB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D498/22—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
-
- 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
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Pulmonology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2825445A DE2825445C2 (de) | 1975-06-13 | 1978-06-09 | Rifamycin-S-Verbindungen und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS557203A JPS557203A (en) | 1980-01-19 |
| JPH0114238B2 true JPH0114238B2 (ru) | 1989-03-10 |
Family
ID=6041475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7706378A Granted JPS557203A (en) | 1978-06-09 | 1978-06-27 | Rifamycin compound and its manufacture |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS557203A (ru) |
| BE (1) | BE870570R (ru) |
| CA (1) | CA1089453A (ru) |
| CH (1) | CH633014A5 (ru) |
| FR (1) | FR2426690A2 (ru) |
| GB (1) | GB1603127A (ru) |
| NL (2) | NL182564C (ru) |
| SE (1) | SE441751B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1154655B (it) * | 1980-05-22 | 1987-01-21 | Alfa Farmaceutici Spa | Derivati imidazo-rifamicinici metodi per la loro preparazione e loro uso come sostanza ad azione antibatterica |
| US7678791B2 (en) | 2006-07-12 | 2010-03-16 | Cumbre Ip Ventures, L.P. | Nitroheteroaryl-containing rifamycin derivatives |
| WO2009064792A1 (en) * | 2007-11-16 | 2009-05-22 | Cumbre Pharmaceuticals Inc. | Quinolone carboxylic acid-substituted rifamycin derivatives |
| RU2496475C2 (ru) | 2011-10-26 | 2013-10-27 | Александр Васильевич Иващенко | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| CN103408571B (zh) * | 2013-08-23 | 2015-11-18 | 成都樵枫科技发展有限公司 | 利福布丁的晶型i及其制备方法和用途 |
| CN106279205B (zh) * | 2015-05-12 | 2020-07-21 | 重庆华邦胜凯制药有限公司 | 制备利福霉素s衍生物的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1056271B (it) * | 1975-05-20 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
-
1978
- 1978-05-22 CH CH554478A patent/CH633014A5/it not_active IP Right Cessation
- 1978-05-23 SE SE7805863A patent/SE441751B/sv not_active IP Right Cessation
- 1978-05-24 GB GB22170/78A patent/GB1603127A/en not_active Expired
- 1978-05-24 FR FR7815450A patent/FR2426690A2/fr active Granted
- 1978-05-30 CA CA304,380A patent/CA1089453A/en not_active Expired
- 1978-06-20 NL NLAANVRAGE7806659,A patent/NL182564C/xx not_active IP Right Cessation
- 1978-06-27 JP JP7706378A patent/JPS557203A/ja active Granted
- 1978-09-18 BE BE190561A patent/BE870570R/xx active
-
1995
- 1995-11-22 NL NL950028C patent/NL950028I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE441751B (sv) | 1985-11-04 |
| GB1603127A (en) | 1981-11-18 |
| FR2426690A2 (fr) | 1979-12-21 |
| SE7805863L (sv) | 1979-11-24 |
| FR2426690B2 (ru) | 1982-05-28 |
| NL950028I1 (nl) | 1996-03-01 |
| JPS557203A (en) | 1980-01-19 |
| NL7806659A (nl) | 1979-12-27 |
| CA1089453A (en) | 1980-11-11 |
| NL182564B (nl) | 1987-11-02 |
| NL950028I2 (nl) | 1997-04-01 |
| BE870570R (fr) | 1979-01-15 |
| NL182564C (nl) | 1988-04-05 |
| CH633014A5 (en) | 1982-11-15 |
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