PH26291A - Oxetanones - Google Patents
Oxetanones Download PDFInfo
- Publication number
- PH26291A PH26291A PH33205A PH33205A PH26291A PH 26291 A PH26291 A PH 26291A PH 33205 A PH33205 A PH 33205A PH 33205 A PH33205 A PH 33205A PH 26291 A PH26291 A PH 26291A
- Authority
- PH
- Philippines
- Prior art keywords
- pyran
- tetrahydro
- hexyl
- hydroxy
- formyl
- Prior art date
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- -1 carbamoylethyl Chemical group 0.000 claims abstract description 134
- 239000002253 acid Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 150000007513 acids Chemical class 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
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- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000004367 Lipase Substances 0.000 claims description 5
- 102000004882 Lipase Human genes 0.000 claims description 5
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- 210000000496 pancreas Anatomy 0.000 claims description 5
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
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- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 241000239290 Araneae Species 0.000 claims 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 22
- 229910052786 argon Inorganic materials 0.000 abstract description 7
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- 101100134927 Gallus gallus COR8 gene Proteins 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 78
- 229960000380 propiolactone Drugs 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 17
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- JMANFENOVOAFTJ-UHFFFAOYSA-N methyl 3-(oxan-2-yloxy)tetradecanoate Chemical compound CCCCCCCCCCCC(CC(=O)OC)OC1CCCCO1 JMANFENOVOAFTJ-UHFFFAOYSA-N 0.000 description 1
- UOZZAMWODZQSOA-UHFFFAOYSA-N methyl 3-hydroxytetradecanoate Chemical compound CCCCCCCCCCCC(O)CC(=O)OC UOZZAMWODZQSOA-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MERGMNQXULKBCH-UHFFFAOYSA-N pyran-2,4-dione Chemical compound O=C1CC(=O)C=CO1 MERGMNQXULKBCH-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- ATKQQTNXMNHRCW-QGZVFWFLSA-N tert-butyl 2-[(r)-(4-methylphenyl)sulfinyl]acetate Chemical compound CC1=CC=C([S@](=O)CC(=O)OC(C)(C)C)C=C1 ATKQQTNXMNHRCW-QGZVFWFLSA-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
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH610284 | 1984-12-21 | ||
| CH393485 | 1985-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26291A true PH26291A (en) | 1992-04-10 |
Family
ID=25694219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH33205A PH26291A (en) | 1984-12-21 | 1985-12-18 | Oxetanones |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4931463A (cs) |
| EP (1) | EP0185359B1 (cs) |
| CN (1) | CN1012643B (cs) |
| AT (1) | ATE70061T1 (cs) |
| AU (1) | AU583569B2 (cs) |
| CA (1) | CA1270837A (cs) |
| CS (1) | CS262425B2 (cs) |
| DE (1) | DE3584829D1 (cs) |
| DK (1) | DK166724B1 (cs) |
| DO (1) | DOP1985004386A (cs) |
| FI (1) | FI91403C (cs) |
| HU (1) | HU200172B (cs) |
| IE (1) | IE58926B1 (cs) |
| IL (1) | IL77338A (cs) |
| MC (1) | MC1728A1 (cs) |
| NO (1) | NO171160C (cs) |
| NZ (1) | NZ214565A (cs) |
| PH (1) | PH26291A (cs) |
| PT (1) | PT81748B (cs) |
| ZW (1) | ZW20385A1 (cs) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1328881C (en) * | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
| US5246960A (en) * | 1984-12-21 | 1993-09-21 | Hoffmann-La Roche Inc. | Oxetanones |
| US4895973A (en) * | 1986-08-14 | 1990-01-23 | G. D. Searle & Company | Substituted glutaric acid lactones in the treatment of hyperlipidemia |
| US4806564A (en) * | 1987-05-26 | 1989-02-21 | Merck & Co., Inc. | Antihypercholesterolemic beta-lactones |
| US4816477A (en) * | 1987-05-26 | 1989-03-28 | Merck & Co., Inc. | Antihypercholesterolemic β-lactones |
| CA2035972C (en) * | 1990-02-23 | 2006-07-11 | Martin Karpf | Process for the preparation of oxetanones |
| US5260310A (en) * | 1990-02-26 | 1993-11-09 | Hoffmann-La Roche Inc. | Oxetanone compounds and pharmaceutical compositions containing them |
| CA2098167C (en) * | 1992-06-24 | 2006-12-19 | Dorothea Isler | Foodstuffs and feedstuffs containing a lipase inhibitor |
| PT1017408E (pt) * | 1997-02-05 | 2005-07-29 | Hoffmann La Roche | Utilizacao de tetra-hidrolipstatina no tratamento de diabetes de tipo ii |
| GB2338235B (en) * | 1997-04-15 | 2001-11-14 | Csir | Appetite suppressing plant extracts |
| GB2355657B (en) * | 1999-10-27 | 2004-07-28 | Phytopharm Plc | Inhibitors Of Gastric Acid Secretion |
| CN1342169A (zh) * | 1999-10-29 | 2002-03-27 | 约翰·贾森·金特里·穆林斯 | 氧杂环丁烷酮衍生物 |
| EP1132389A1 (en) | 2000-03-06 | 2001-09-12 | Vernalis Research Limited | New aza-indolyl derivatives for the treatment of obesity |
| GB2363985B (en) * | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
| EP1307263B1 (en) * | 2000-07-28 | 2005-04-20 | F. Hoffmann-La Roche Ag | New use of lipase inhibitors |
| KR100494245B1 (ko) | 2000-08-09 | 2005-06-13 | 에프. 호프만-라 로슈 아게 | 리파제 억제제의 용도 |
| US6900226B2 (en) | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
| US6392061B1 (en) * | 2000-10-16 | 2002-05-21 | Zpro Chemical, Inc. | Process for making (2S, 3S, 5S) oxetanone derivatives |
| AU2167002A (en) | 2000-10-16 | 2002-06-11 | Hoffmann La Roche | Indoline derivatives and their use as 5-ht2 receptor ligands |
| GB0030710D0 (en) | 2000-12-15 | 2001-01-31 | Hoffmann La Roche | Piperazine derivatives |
| KR100539143B1 (ko) | 2000-12-27 | 2005-12-26 | 에프. 호프만-라 로슈 아게 | 인돌 유도체 및 그의 5-ｈｔ2ｂ 및 5-ｈｔ2ｃ 수용체리간드로서의 용도 |
| GB0106177D0 (en) | 2001-03-13 | 2001-05-02 | Hoffmann La Roche | Piperazine derivatives |
| JP3715280B2 (ja) | 2001-05-21 | 2005-11-09 | エフ．ホフマン−ラ ロシュ アーゲー | ニューロペプチドｙレセプターのリガンドとしてのキノリン誘導体 |
| US6730319B2 (en) | 2001-06-06 | 2004-05-04 | Hoffmann-La Roche Inc. | Pharmaceutical compositions having depressed melting points |
| US20030027786A1 (en) | 2001-06-06 | 2003-02-06 | Karsten Maeder | Lipase inhibiting composition |
| US6787558B2 (en) | 2001-09-28 | 2004-09-07 | Hoffmann-La Roche Inc. | Quinoline derivatives |
| GB0202015D0 (en) | 2002-01-29 | 2002-03-13 | Hoffmann La Roche | Piperazine Derivatives |
| WO2003066055A1 (en) | 2002-02-04 | 2003-08-14 | F. Hoffmann-La Roche Ag | Quinoline derivatives as npy antagonists |
| MXPA04008379A (es) | 2002-02-28 | 2004-11-26 | Hoffmann La Roche | Derivados de tiazol como antagonistas del receptor de neuropeptido y (npy). |
| US7728153B2 (en) | 2002-04-17 | 2010-06-01 | The Burnham Institute For Medical Research | Method for the asymmetric synthesis of beta-lactone compounds |
| AU2003226370A1 (en) * | 2002-04-17 | 2003-11-03 | The Burnham Institute | Inhibition of fatty acid synthase by beta-lactones and other compounds for inhibition of cellular proliferation |
| EP1560816A1 (en) | 2002-07-05 | 2005-08-10 | F. Hoffmann-La Roche Ag | Quinazoline derivatives |
| RU2324685C2 (ru) | 2002-08-07 | 2008-05-20 | Ф.Хоффманн-Ля Рош Аг | Производные тиазола, способ их получения и применение, фармацевтическая композиция, обладающая свойствами антагонистов рецепторов npy |
| RU2296759C2 (ru) | 2002-09-12 | 2007-04-10 | Ф.Хоффманн-Ля Рош Аг | N-замещенные 1н-индол-5-пропионовые кислоты, фармацевтическая композиция, содержащая эти соединения, и их применение (варианты) |
| US6727277B1 (en) | 2002-11-12 | 2004-04-27 | Kansas State University Research Foundation | Compounds affecting cholesterol absorption |
| RU2315767C2 (ru) | 2002-11-25 | 2008-01-27 | Ф.Хоффманн-Ля Рош Аг | Индолилпроизводные, способ их получения, фармацевтическая композиция, способ лечения и/или профилактики заболеваний |
| GB0314967D0 (en) | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| EP1651627A2 (en) * | 2003-07-15 | 2006-05-03 | Ranbaxy Laboratories Limited | Process for preparation of oxetan-2-ones |
| RU2006107444A (ru) | 2003-08-12 | 2007-09-20 | Ф.Хоффманн-Ля Рош Аг (Ch) | 2-амино-5-бензоилтиазолы в качестве антагонистов npy |
| RU2321586C2 (ru) | 2003-08-12 | 2008-04-10 | Ф.Хоффманн-Ля Рош Аг | Производные тиазола в качестве антагонистов npy |
| DE102004009076A1 (de) * | 2004-02-23 | 2005-10-27 | Solvay Pharmaceuticals Gmbh | Alkylcarbamat-substituierte β-Lactone, Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US7074822B2 (en) * | 2004-02-23 | 2006-07-11 | Solvay Pharmaceuticals Gmbh | Alkyl carbamate-substituted β-lactones, process for their preparation, and pharmaceutical compositions containing them |
| US7121355B2 (en) * | 2004-09-21 | 2006-10-17 | Cnh America Llc | Bulldozer autograding system |
| WO2006035296A1 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Process for the preparation of an orlistat derivative useful as reference standard in the determination of the purity of orlistat and process for the preparation of orlistat |
| CN101171252B (zh) | 2005-05-03 | 2011-06-01 | 霍夫曼-拉罗奇有限公司 | 作为5-ht2配体的四环氮杂吡嗪并二氢吲哚类化合物 |
| AU2006281435A1 (en) | 2005-08-18 | 2007-02-22 | F. Hoffmann-La Roche Ag | Thiazolyl piperidine derivatives useful as H3 receptor modulators |
| US20090171104A1 (en) * | 2005-10-05 | 2009-07-02 | Killol Patel | Process for the preparation of orlistat |
| ES2359739T3 (es) | 2005-11-30 | 2011-05-26 | F. Hoffmann-La Roche Ag | Derivados de indol-2-il-amida 1,5-sustituida. |
| CN101316838B (zh) | 2005-11-30 | 2013-01-30 | 霍夫曼-拉罗奇有限公司 | 用作h3调节剂的1,1-二氧代-硫代吗啉基吲哚基甲酮衍生物 |
| CN101316835A (zh) | 2005-11-30 | 2008-12-03 | 霍夫曼-拉罗奇有限公司 | 5-取代的吲哚-2-甲酰胺衍生物 |
| DE602006010433D1 (de) | 2005-12-09 | 2009-12-24 | Hoffmann La Roche | Für die behandlung von obesitas geeignete tricyclische amidderivate |
| KR20080068127A (ko) | 2005-12-15 | 2008-07-22 | 에프. 호프만-라 로슈 아게 | 피롤로[2,3-ｃ]피리딘 유도체 |
| ES2344077T3 (es) | 2005-12-16 | 2010-08-17 | F.Hoffmann-La Roche Ag | Derivados de pirrolo(2,3-b)piridina como moduladores del receptor h3. |
| RU2008132966A (ru) * | 2006-01-13 | 2010-02-20 | Ф.Хоффманн-Ля Рош Аг (Ch) | Производные циклогексилпиперазинилметанона и их применение в качестве модуляторов гистамин н3 рецептора |
| CA2637449A1 (en) * | 2006-01-23 | 2007-07-26 | F. Hoffmann-La Roche Ag | Cyclohexyl sulfonamide derivatives having h3 receptor activity |
| US7432255B2 (en) | 2006-05-16 | 2008-10-07 | Hoffmann-La Roche Inc. | 1H-indol-5-yl-piperazin-1-yl-methanone derivatives |
| EP2032554A1 (en) * | 2006-05-30 | 2009-03-11 | F. Hoffmann-Roche AG | Piperidinyl pyrimidine derivatives |
| US7514433B2 (en) | 2006-08-03 | 2009-04-07 | Hoffmann-La Roche Inc. | 1H-indole-6-yl-piperazin-1-yl-methanone derivatives |
| US20080146559A1 (en) | 2006-12-08 | 2008-06-19 | Li Chen | 4,5,6,7-Tetrahydro-Thieno [2,3-C] Pyridine Derivatives |
| SG182171A1 (en) * | 2007-06-06 | 2012-07-30 | Ranbaxy Lab Ltd | Process for the preparation of orlistat |
| BRPI0814532A2 (pt) | 2007-07-25 | 2015-01-27 | Hoffmann La Roche | Compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação dos receptores de h3, e uso desses compostos para a preparação de medicamentos. |
| WO2009059046A1 (en) * | 2007-10-31 | 2009-05-07 | Burnham Institute For Medical Research | Beta-lactone compounds |
| WO2010112569A1 (en) | 2009-03-31 | 2010-10-07 | Robert Zimmermann | Modulation of adipose triglyceride lipase for prevention and treatment of cachexia, loss of weight and muscle atrophy and methods of screening therefor |
| EP2414830A2 (en) | 2009-03-31 | 2012-02-08 | Robert Zimmermann | Modulation of adipose triglyceride lipase for prevention and treatment of cachexia, loss of weight and muscle atrophy and methods of screening therefor |
| US8450350B2 (en) | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
| CA2798330A1 (en) | 2010-05-05 | 2011-11-10 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
| PL4218753T3 (pl) | 2017-07-12 | 2026-04-20 | Mayo Foundation For Medical Education And Research | Nowe inhibitory lipazy i ich zastosowania |
| CN112079821A (zh) * | 2020-09-14 | 2020-12-15 | 中山万汉制药有限公司 | 奥利司他与苯氨基嘧啶类化合物形成的缀合物及其制备方法与用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2478388A (en) * | 1945-09-28 | 1949-08-09 | Eastman Kodak Co | beta-lactones from unsaturated aldehydes and unsaturated ketones |
| JPS608117B2 (ja) * | 1977-02-08 | 1985-02-28 | 財団法人微生物化学研究会 | 新生理活性物質エステラスチンおよびその製造法 |
| GB2023604B (en) * | 1978-05-25 | 1982-07-28 | Microbial Chem Res Found | Physiologically active derivatives of esterastin and production thereof |
| JPS56128774A (en) * | 1980-03-14 | 1981-10-08 | Microbial Chem Res Found | New physiologically active substance ebelactone and its preparation |
| CA1247547A (en) * | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
-
1985
- 1985-11-12 CA CA000495058A patent/CA1270837A/en not_active Expired - Lifetime
- 1985-11-15 ZW ZW203/85A patent/ZW20385A1/xx unknown
- 1985-12-04 FI FI854797A patent/FI91403C/fi not_active IP Right Cessation
- 1985-12-09 CS CS859016A patent/CS262425B2/cs not_active IP Right Cessation
- 1985-12-16 NZ NZ214565A patent/NZ214565A/xx unknown
- 1985-12-16 AU AU51259/85A patent/AU583569B2/en not_active Expired
- 1985-12-16 IL IL77338A patent/IL77338A/xx not_active IP Right Cessation
- 1985-12-17 DE DE8585116096T patent/DE3584829D1/de not_active Expired - Lifetime
- 1985-12-17 AT AT85116096T patent/ATE70061T1/de not_active IP Right Cessation
- 1985-12-17 EP EP85116096A patent/EP0185359B1/de not_active Expired - Lifetime
- 1985-12-18 MC MC851814A patent/MC1728A1/fr unknown
- 1985-12-18 HU HU854832A patent/HU200172B/hu unknown
- 1985-12-18 PH PH33205A patent/PH26291A/en unknown
- 1985-12-19 CN CN85108888A patent/CN1012643B/zh not_active Expired
- 1985-12-20 IE IE327785A patent/IE58926B1/en not_active IP Right Cessation
- 1985-12-20 DK DK600385A patent/DK166724B1/da not_active IP Right Cessation
- 1985-12-20 PT PT81748A patent/PT81748B/pt unknown
- 1985-12-20 NO NO855213A patent/NO171160C/no not_active IP Right Cessation
- 1985-12-30 DO DO1985004386A patent/DOP1985004386A/es unknown
-
1987
- 1987-12-17 US US07/134,322 patent/US4931463A/en not_active Expired - Lifetime
-
1990
- 1990-03-19 US US07/495,809 patent/US5175186A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO171160B (no) | 1992-10-26 |
| IE58926B1 (en) | 1993-12-01 |
| FI854797A0 (fi) | 1985-12-04 |
| DE3584829D1 (de) | 1992-01-16 |
| DK166724B1 (da) | 1993-07-05 |
| IL77338A (en) | 1991-04-15 |
| PT81748A (en) | 1986-01-02 |
| EP0185359A3 (en) | 1987-08-26 |
| DOP1985004386A (es) | 1991-04-20 |
| EP0185359B1 (de) | 1991-12-04 |
| PT81748B (pt) | 1988-07-29 |
| MC1728A1 (fr) | 1986-12-15 |
| DK600385A (da) | 1986-06-22 |
| AU5125985A (en) | 1986-06-26 |
| NZ214565A (en) | 1989-06-28 |
| CN85108888A (zh) | 1986-07-09 |
| IE853277L (en) | 1986-06-21 |
| CS262425B2 (en) | 1989-03-14 |
| HUT39440A (en) | 1986-09-29 |
| ZW20385A1 (en) | 1986-03-05 |
| FI91403C (fi) | 1994-06-27 |
| NO171160C (no) | 1993-02-03 |
| DK600385D0 (da) | 1985-12-20 |
| FI91403B (fi) | 1994-03-15 |
| CA1270837A (en) | 1990-06-26 |
| US5175186A (en) | 1992-12-29 |
| CN1012643B (zh) | 1991-05-22 |
| HU200172B (en) | 1990-04-28 |
| EP0185359A2 (de) | 1986-06-25 |
| NO855213L (no) | 1986-06-23 |
| ATE70061T1 (de) | 1991-12-15 |
| US4931463A (en) | 1990-06-05 |
| FI854797A7 (fi) | 1986-06-22 |
| AU583569B2 (en) | 1989-05-04 |
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