NO743490L - - Google Patents
Info
- Publication number
- NO743490L NO743490L NO743490A NO743490A NO743490L NO 743490 L NO743490 L NO 743490L NO 743490 A NO743490 A NO 743490A NO 743490 A NO743490 A NO 743490A NO 743490 L NO743490 L NO 743490L
- Authority
- NO
- Norway
- Prior art keywords
- deoxy
- demethyl
- tetracycline
- catalyst
- tetracyclines
- Prior art date
Links
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 239000004098 Tetracycline Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 229940040944 tetracyclines Drugs 0.000 description 8
- 239000003446 ligand Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000005695 dehalogenation reaction Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229960002180 tetracycline Drugs 0.000 description 6
- 235000019364 tetracycline Nutrition 0.000 description 6
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical group [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 5
- 229910000510 noble metal Inorganic materials 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229960003722 doxycycline Drugs 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 150000003003 phosphines Chemical group 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical group [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 3
- 229930101283 tetracycline Natural products 0.000 description 3
- 150000003522 tetracyclines Chemical group 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000074 antimony hydride Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JYUXDXWXTPSAEL-UHFFFAOYSA-N 1,4-dioxane;oxolane Chemical compound C1CCOC1.C1COCCO1 JYUXDXWXTPSAEL-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 tetracycline compound Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2948773 | 1973-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO743490L true NO743490L (xx) | 1975-04-28 |
Family
ID=11227076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743490A NO743490L (xx) | 1973-09-28 | 1974-09-26 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3962331A (xx) |
| JP (1) | JPS5062968A (xx) |
| AT (1) | AT340043B (xx) |
| BE (1) | BE820476A (xx) |
| CA (1) | CA1026326A (xx) |
| CH (1) | CH605659A5 (xx) |
| DE (1) | DE2446587A1 (xx) |
| DK (1) | DK501574A (xx) |
| ES (1) | ES430511A1 (xx) |
| FR (1) | FR2257570B1 (xx) |
| GB (1) | GB1487929A (xx) |
| IL (1) | IL45739A (xx) |
| NL (1) | NL7412762A (xx) |
| NO (1) | NO743490L (xx) |
| SE (1) | SE7412216L (xx) |
| ZA (1) | ZA746122B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK386784A (da) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | Fremgangsmaade til fremstilling af alfa-6-desoxy-tetracykliner |
| US4973719A (en) * | 1988-10-28 | 1990-11-27 | Ranbaxy Laboratories Limited | Process for the production of alpha-6-deoxytetracyclines |
| US4987242A (en) * | 1988-10-28 | 1991-01-22 | Jagmohan Khanna | Hydrogenation catalyst useful in the production of alpha-6-deoxytetracyclines |
| US5049683A (en) * | 1989-01-04 | 1991-09-17 | Houba, Inc. | Process for the production of alpha-6-deoxytetracyclines |
| US5015780A (en) * | 1989-02-02 | 1991-05-14 | Ciba-Geigy Corporation | Process for the preparation of dihalobutyraldehydes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250809A (en) * | 1962-09-06 | 1966-05-10 | Pfizer & Co C | 6-deoxy-6-demethyl-6-halomethylene tetracyclines and their 11a-chloro and fluoro derivatives |
| US3649700A (en) * | 1966-12-20 | 1972-03-14 | Knapsack Ag | Process for the dehydrochlorination of chlorinated hydrocarbons |
| US3659006A (en) * | 1969-06-17 | 1972-04-25 | Borg Warner | Synthesis of alpha-haloacrylonitrile |
-
1974
- 1974-09-24 DK DK501574A patent/DK501574A/da not_active Application Discontinuation
- 1974-09-25 US US05/509,055 patent/US3962331A/en not_active Expired - Lifetime
- 1974-09-25 CA CA210,079A patent/CA1026326A/en not_active Expired
- 1974-09-25 IL IL45739A patent/IL45739A/xx unknown
- 1974-09-26 NO NO743490A patent/NO743490L/no unknown
- 1974-09-26 AT AT776374A patent/AT340043B/de not_active IP Right Cessation
- 1974-09-26 GB GB41962/74A patent/GB1487929A/en not_active Expired
- 1974-09-26 ZA ZA00746122A patent/ZA746122B/xx unknown
- 1974-09-27 CH CH1305674A patent/CH605659A5/xx not_active IP Right Cessation
- 1974-09-27 SE SE7412216A patent/SE7412216L/xx unknown
- 1974-09-27 NL NL7412762A patent/NL7412762A/xx not_active Application Discontinuation
- 1974-09-27 BE BE149015A patent/BE820476A/xx unknown
- 1974-09-28 JP JP49112210A patent/JPS5062968A/ja active Pending
- 1974-09-28 ES ES430511A patent/ES430511A1/es not_active Expired
- 1974-09-30 FR FR7432897A patent/FR2257570B1/fr not_active Expired
- 1974-09-30 DE DE19742446587 patent/DE2446587A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| SE7412216L (xx) | 1975-04-01 |
| NL7412762A (nl) | 1975-04-02 |
| GB1487929A (en) | 1977-10-05 |
| BE820476A (fr) | 1975-01-16 |
| IL45739A (en) | 1979-05-31 |
| US3962331A (en) | 1976-06-08 |
| DE2446587A1 (de) | 1975-04-03 |
| ATA776374A (de) | 1977-03-15 |
| ZA746122B (en) | 1975-11-26 |
| AT340043B (de) | 1977-11-25 |
| JPS5062968A (xx) | 1975-05-29 |
| AU7381374A (en) | 1976-04-01 |
| FR2257570B1 (xx) | 1978-08-11 |
| ES430511A1 (es) | 1976-10-16 |
| DK501574A (xx) | 1975-05-26 |
| CH605659A5 (xx) | 1978-10-13 |
| CA1026326A (en) | 1978-02-14 |
| FR2257570A1 (xx) | 1975-08-08 |
| IL45739A0 (en) | 1974-11-29 |
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