LT3676B - Macrolide compounds - Google Patents
Macrolide compounds Download PDFInfo
- Publication number
- LT3676B LT3676B LTIP1076A LTIP1076A LT3676B LT 3676 B LT3676 B LT 3676B LT IP1076 A LTIP1076 A LT IP1076A LT IP1076 A LTIP1076 A LT IP1076A LT 3676 B LT3676 B LT 3676B
- Authority
- LT
- Lithuania
- Prior art keywords
- group
- formula
- compound
- compounds
- hydroxyl group
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 145
- 239000003120 macrolide antibiotic agent Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 70
- -1 methoxycarbonyloxy, acetoxy, methoxy Chemical group 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 239000000969 carrier Substances 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 241000244206 Nematoda Species 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 241000238876 Acari Species 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims 3
- 238000003898 horticulture Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000004480 active ingredient Substances 0.000 description 41
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- 239000000243 solution Substances 0.000 description 37
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- 238000010828 elution Methods 0.000 description 16
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- 238000000855 fermentation Methods 0.000 description 9
- 230000004151 fermentation Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 235000019445 benzyl alcohol Nutrition 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 235000017281 sodium acetate Nutrition 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
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- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000008108 microcrystalline cellulose Substances 0.000 description 6
- 229940016286 microcrystalline cellulose Drugs 0.000 description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 239000007800 oxidant agent Substances 0.000 description 5
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- 235000003911 Arachis Nutrition 0.000 description 4
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
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- 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 description 3
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- RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 3
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- CJOSOISHDAKZKA-UHFFFAOYSA-N n,n-diethylethanamine;1h-imidazole Chemical compound C1=CNC=N1.CCN(CC)CC CJOSOISHDAKZKA-UHFFFAOYSA-N 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- CEYGNZMCCVVXQW-UHFFFAOYSA-N phosphoric acid;propane-1,2-diol Chemical compound CC(O)CO.OP(O)(O)=O CEYGNZMCCVVXQW-UHFFFAOYSA-N 0.000 description 1
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- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
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- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
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- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
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- 230000002459 sustained effect Effects 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 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
- 238000012546 transfer Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Insects & Arthropods (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868613790A GB8613790D0 (en) | 1986-06-06 | 1986-06-06 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1076A LTIP1076A (en) | 1995-04-25 |
| LT3676B true LT3676B (en) | 1996-01-25 |
Family
ID=10599054
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1076A LT3676B (en) | 1986-06-06 | 1993-09-22 | Macrolide compounds |
| LTRP1260A LT2643B (lt) | 1986-06-06 | 1993-09-29 | Makrolidiniu junginiu gavimo budas |
| LTIP1649A LTIP1649A (en) | 1986-06-06 | 1993-12-21 | Macrolidic compounds |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTRP1260A LT2643B (lt) | 1986-06-06 | 1993-09-29 | Makrolidiniu junginiu gavimo budas |
| LTIP1649A LTIP1649A (en) | 1986-06-06 | 1993-12-21 | Macrolidic compounds |
Country Status (10)
| Country | Link |
|---|---|
| AP (1) | AP38A (ro) |
| GB (1) | GB8613790D0 (ro) |
| GE (1) | GEP19970660B (ro) |
| LT (3) | LT3676B (ro) |
| LV (1) | LV5678A3 (ro) |
| MD (3) | MD20B1 (ro) |
| RU (1) | RU1831483C (ro) |
| SU (1) | SU1731060A3 (ro) |
| UA (2) | UA18587A (ro) |
| ZA (1) | ZA874052B (ro) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB216646A (en) | 1923-04-17 | 1924-06-05 | Reginald Arthur Angier | Improvements in feeding troughs for pigs and other animals |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT81125B (pt) * | 1984-09-14 | 1987-10-20 | American Cyanamid Co | Processo para a preparacao de compostos macrolidos por fermentacao de organismos streptomyces |
| DE3446134A1 (de) * | 1984-12-18 | 1986-06-26 | G. Düsterloh GmbH, 4322 Sprockhövel | Reversierbare hydraulische maschine |
| IL78621A (en) * | 1985-04-30 | 1991-06-30 | American Cyanamid Co | Mylbemycin analogs,their preparation and pesticidal compositions containing them |
-
1986
- 1986-06-06 GB GB868613790A patent/GB8613790D0/en active Pending
-
1987
- 1987-06-05 AP APAP/P/1987/000065A patent/AP38A/en active
- 1987-06-05 ZA ZA874052A patent/ZA874052B/xx unknown
- 1987-06-05 RU SU874203050A patent/RU1831483C/ru active
- 1987-06-05 UA UA4613245A patent/UA18587A/uk unknown
- 1987-06-05 UA UA4203050A patent/UA12797A/uk unknown
-
1989
- 1989-01-13 SU SU894613245A patent/SU1731060A3/ru active
-
1993
- 1993-09-22 LT LTIP1076A patent/LT3676B/lt not_active IP Right Cessation
- 1993-09-29 LT LTRP1260A patent/LT2643B/xx not_active IP Right Cessation
- 1993-10-08 LV LV931144A patent/LV5678A3/xx unknown
- 1993-12-21 LT LTIP1649A patent/LTIP1649A/xx not_active Application Discontinuation
-
1994
- 1994-04-27 MD MD940087A patent/MD20B1/ro active IP Right Grant
- 1994-05-16 GE GEAP19941921A patent/GEP19970660B/en unknown
- 1994-05-31 MD MD94-0129A patent/MD123C2/ro active IP Right Grant
- 1994-07-14 MD MD94-0360A patent/MD1026G2/ro not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB216646A (en) | 1923-04-17 | 1924-06-05 | Reginald Arthur Angier | Improvements in feeding troughs for pigs and other animals |
Non-Patent Citations (3)
| Title |
|---|
| A. G. ANASTASSIOU ET AL.: "Generation and thermal reorganization of a linearly-fused N-methyldibenzoazocinyl anion", J. CHEM. SOC., CHEM. COMMUN.,, 1981, pages 647 - 648 |
| D. HANDS ET AL.: "The synthesis of 3-hydroxymethyldibenzo[b,f]thiepin 5,5-dioxide, a prostaglandin antagonist", JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, pages 1333 |
| T. W. GREENE: "Protective Groups in Organic Chemistry" |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA874052B (en) | 1988-02-24 |
| MD123C2 (ro) | 1995-06-30 |
| GEP19970660B (en) | 1997-01-04 |
| LV5678A3 (lv) | 1994-10-20 |
| LT2643B (lt) | 1994-04-25 |
| UA12797A (uk) | 1997-02-28 |
| UA18587A (uk) | 1997-12-25 |
| GB8613790D0 (en) | 1986-07-09 |
| MD123B1 (ro) | 1994-12-31 |
| SU1731060A3 (ru) | 1992-04-30 |
| LTIP1649A (en) | 1995-07-25 |
| LTIP1076A (en) | 1995-04-25 |
| AP38A (en) | 1989-04-13 |
| MD20C2 (ro) | 1994-05-31 |
| RU1831483C (ru) | 1993-07-30 |
| MD1026G2 (ro) | 1999-06-30 |
| MD20B1 (ro) | 1994-05-31 |
| AP8700065A0 (en) | 1987-05-01 |
| MD940360A (ro) | 1996-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD9A | Change of patent owner |
Owner name: WYETH HOLDINGS CORPORATION, US Effective date: 20031031 |
|
| PC9A | Transfer of patents |
Owner name: ZOETIS WHC 2 LLC, US Effective date: 20130613 |
|
| PD9A | Change of patent owner |
Owner name: ZOETIS WHC 2 LLC, US Effective date: 20130613 |
|
| MK9A | Expiry of a patent |
Effective date: 20130922 |