NO128028B - - Google Patents
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- Publication number
- NO128028B NO128028B NO02104/68A NO210468A NO128028B NO 128028 B NO128028 B NO 128028B NO 02104/68 A NO02104/68 A NO 02104/68A NO 210468 A NO210468 A NO 210468A NO 128028 B NO128028 B NO 128028B
- Authority
- NO
- Norway
- Prior art keywords
- rifamycin
- substituted
- solvent
- formaldehyde
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 claims description 6
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=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 BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 claims description 6
- -1 SV compound Chemical class 0.000 claims description 6
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical class 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 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 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 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 125000005638 hydrazono group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940109171 rifamycin sv Drugs 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 2
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO16372A NO136196C (no) | 1967-06-07 | 1972-01-24 | Fremgangsm}te til fremstilling av 3-iminometyl-rifamycin sv-derivater. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1692567 | 1967-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128028B true NO128028B (xx) | 1973-09-17 |
Family
ID=11149560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02104/68A NO128028B (xx) | 1967-06-07 | 1968-05-29 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3542762A (xx) |
| AT (1) | AT284338B (xx) |
| BE (1) | BE716123A (xx) |
| BR (1) | BR6899560D0 (xx) |
| CH (2) | CH488731A (xx) |
| DE (2) | DE1770579C3 (xx) |
| DK (1) | DK134911B (xx) |
| ES (1) | ES354780A1 (xx) |
| FI (1) | FI58922C (xx) |
| FR (1) | FR1585041A (xx) |
| GB (1) | GB1219360A (xx) |
| IL (1) | IL30053A (xx) |
| NL (1) | NL145554B (xx) |
| NO (1) | NO128028B (xx) |
| SE (2) | SE362432B (xx) |
| YU (1) | YU33662B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR207762A1 (es) * | 1973-07-25 | 1976-10-29 | Archifar Ind Chim Trentino | Procedimiento para la preparacion de 3-((4-metil-1-piperazin-1-il)-imino)-metil-rifamicina sv o rifampicina |
| DE2728869A1 (de) * | 1976-06-25 | 1977-12-29 | Antibiotice Iasi Intreprindere | Rifamycinen und verfahren zu deren herstellung |
| JPS5473799A (en) * | 1977-11-16 | 1979-06-13 | Kanebo Ltd | Preparation of 1,3-oxazino (5,6-c) rifamycin derivative |
| GB1594134A (en) * | 1977-11-25 | 1981-07-30 | Holco Investment Inc | Rifamycins |
| JPS5776597A (en) * | 1980-10-30 | 1982-05-13 | Kiyouritsu Kurieiteibu Asoshie | Electric musical instrument |
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| GB8318072D0 (en) * | 1983-07-04 | 1983-08-03 | Lepetit Spa | Water-soluble rifampicin derivatives |
| CN103755723B (zh) * | 2014-02-07 | 2016-04-20 | 天津大学 | 一种利福平i晶型的制备方法 |
| CN103819487B (zh) * | 2014-02-07 | 2016-08-24 | 天津大学 | 一种利福平晶体及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1090115A (en) * | 1964-04-02 | 1967-11-08 | Lepetit Spa | Mannich bases of rifamycin sv |
| FR208F (xx) * | 1964-07-31 | |||
| FR1457435A (fr) * | 1964-07-31 | 1966-01-24 | Lepetit Spa | Procédé pour préparer des composés dérivés de la rifamycine |
-
1968
- 1968-05-21 NL NL6807202A patent/NL145554B/xx not_active IP Right Cessation
- 1968-05-21 US US730902A patent/US3542762A/en not_active Expired - Lifetime
- 1968-05-23 IL IL30053A patent/IL30053A/xx unknown
- 1968-05-29 NO NO02104/68A patent/NO128028B/no unknown
- 1968-06-04 FR FR1585041D patent/FR1585041A/fr not_active Expired
- 1968-06-04 BR BR199560/68A patent/BR6899560D0/pt unknown
- 1968-06-05 FI FI1559/68A patent/FI58922C/fi active
- 1968-06-05 BE BE716123D patent/BE716123A/xx not_active IP Right Cessation
- 1968-06-05 GB GB26730/68A patent/GB1219360A/en not_active Expired
- 1968-06-06 AT AT542968A patent/AT284338B/de not_active IP Right Cessation
- 1968-06-06 DE DE1770579A patent/DE1770579C3/de not_active Expired
- 1968-06-06 DK DK263168AA patent/DK134911B/da not_active IP Right Cessation
- 1968-06-06 CH CH837368A patent/CH488731A/fr not_active IP Right Cessation
- 1968-06-06 CH CH297170A patent/CH502373A/fr not_active IP Right Cessation
- 1968-06-06 SE SE03909/71A patent/SE362432B/xx unknown
- 1968-06-06 DE DE1795741A patent/DE1795741C2/de not_active Expired
- 1968-06-06 SE SE6807604A patent/SE372270B/xx unknown
- 1968-06-07 YU YU1323/68A patent/YU33662B/xx unknown
- 1968-06-07 ES ES354780A patent/ES354780A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL145554B (nl) | 1975-04-15 |
| BR6899560D0 (pt) | 1973-05-10 |
| DE1795741C2 (de) | 1985-07-04 |
| CH488731A (fr) | 1970-04-15 |
| FI58922C (fi) | 1981-05-11 |
| SE372270B (xx) | 1974-12-16 |
| FR1585041A (xx) | 1970-01-09 |
| FI58922B (fi) | 1981-01-30 |
| ES354780A1 (es) | 1969-12-01 |
| SE362432B (xx) | 1973-12-10 |
| DE1795741A1 (de) | 1974-05-30 |
| DE1770579B2 (de) | 1980-03-20 |
| BE716123A (xx) | 1968-11-04 |
| CH502373A (fr) | 1971-01-31 |
| AT284338B (de) | 1970-09-10 |
| YU132368A (xx) | 1977-06-30 |
| NL6807202A (xx) | 1968-12-09 |
| DE1770579A1 (de) | 1972-03-09 |
| YU33662B (en) | 1977-12-31 |
| US3542762A (en) | 1970-11-24 |
| DK134911B (da) | 1977-02-07 |
| DK134911C (xx) | 1977-06-27 |
| DE1770579C3 (de) | 1980-11-20 |
| GB1219360A (en) | 1971-01-13 |
| IL30053A (en) | 1972-11-28 |
| IL30053A0 (en) | 1968-07-25 |
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