PH26291A - Oxetanones - Google Patents

Oxetanones Download PDF

Info

Publication number: PH26291A
Authority: PH; Philippines
Prior art keywords: pyran; tetrahydro; hexyl; hydroxy; formyl
Prior art date: 1984-12-21

Application number

PH33205A

Other languages

English (en)

Inventor

Pierre Dr Barbier

Fernand Dr Schneider

Ulrich Widmer

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1984-12-21

Filing date

1985-12-18

Publication date

1992-04-10

1985-12-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1992-04-10 Publication of PH26291A publication Critical patent/PH26291A/en

Links

-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
125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 claims description 72
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
150000002148 esters Chemical class 0.000 claims description 57
239000001257 hydrogen Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 9
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
150000002431 hydrogen Chemical class 0.000 claims description 6
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210000000496 pancreas Anatomy 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
229960003136 leucine Drugs 0.000 claims description 3
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
230000002401 inhibitory effect Effects 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
210000004916 vomit Anatomy 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
229910052717 sulfur Inorganic materials 0.000 abstract description 3
101100134927 Gallus gallus COR8 gene Proteins 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000001589 carboacyl group Chemical group 0.000 abstract 1
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
239000000741 silica gel Substances 0.000 description 43
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239000000243 solution Substances 0.000 description 41
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000002360 preparation method Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 17
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OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 12
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 8
235000011167 hydrochloric acid Nutrition 0.000 description 8
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WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
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HFBHOAHFRNLZGN-ZCFIWIBFSA-N (2r)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@H](C(O)=O)NC=O HFBHOAHFRNLZGN-ZCFIWIBFSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000001828 Gelatine Substances 0.000 description 6
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ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
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229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 6
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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)

PH33205A 1984-12-21 1985-12-18 Oxetanones PH26291A (en)

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 (fr)
EP (1)	EP0185359B1 (fr)
CN (1)	CN1012643B (fr)
AT (1)	ATE70061T1 (fr)
AU (1)	AU583569B2 (fr)
CA (1)	CA1270837A (fr)
CS (1)	CS262425B2 (fr)
DE (1)	DE3584829D1 (fr)
DK (1)	DK166724B1 (fr)
DO (1)	DOP1985004386A (fr)
FI (1)	FI91403C (fr)
HU (1)	HU200172B (fr)
IE (1)	IE58926B1 (fr)
IL (1)	IL77338A (fr)
MC (1)	MC1728A1 (fr)
NO (1)	NO171160C (fr)
NZ (1)	NZ214565A (fr)
PH (1)	PH26291A (fr)
PT (1)	PT81748B (fr)
ZW (1)	ZW20385A1 (fr)

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CA2098167C (fr) *	1992-06-24	2006-12-19	Dorothea Isler	Aliments pour humains et animaux contenant un inhibiteur de la lipase
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WO2001032670A1 (fr) *	1999-10-29	2001-05-10	John Jason Gentry Mullins	Dérivés d'oxétanone
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GB2363985B (en) *	2000-06-30	2004-09-29	Phytopharm Plc	Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use
ATE293477T1 (de)	2000-07-28	2005-05-15	Hoffmann La Roche	Neue verwendung von lipase-inhibitoren
CA2417607C (fr)	2000-08-09	2008-01-29	Christine Feinle	Utilisation d'inhibiteurs de lipase
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GB0030710D0 (en)	2000-12-15	2001-01-31	Hoffmann La Roche	Piperazine derivatives
BR0116605A (pt)	2000-12-27	2003-09-30	Hoffmann La Roche	Composto, processo para a preparação de um composto, composição farmacêutica que compreende o mesmo, sua utilização e processo para o tratamento e profilaxia de distúrbios do sistema nervoso central, distúrbios cardiovasculares, distúrbios gastrintestinais e apnéia do sono
GB0106177D0 (en)	2001-03-13	2001-05-02	Hoffmann La Roche	Piperazine derivatives
AU2002338896B2 (en)	2001-05-21	2006-04-27	F.Hoffman-La Roche Ag	Quinoline derivatives as ligands for the neuropeptide Y receptor
US20030027786A1 (en)	2001-06-06	2003-02-06	Karsten Maeder	Lipase inhibiting composition
US6730319B2 (en)	2001-06-06	2004-05-04	Hoffmann-La Roche Inc.	Pharmaceutical compositions having depressed melting points
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
PL372295A1 (en)	2002-02-04	2005-07-11	F.Hoffmann-La Roche Ag	Quinoline derivatives as npy antagonists
BR0308108A (pt)	2002-02-28	2004-12-07	Hoffmann La Roche	Compostos; processo para a preparação de composto; composição farmacêutica que compreende o mesmo, utilização dos compostos e método de tratamento e profilaxia de enfermidades e de obesidade
US7728153B2 (en)	2002-04-17	2010-06-01	The Burnham Institute For Medical Research	Method for the asymmetric synthesis of beta-lactone compounds
WO2003088975A1 (fr) *	2002-04-17	2003-10-30	The Burnham Institute	Inhibition de synthase d'acide gras par beta-lactones et par d'autres composes destines a inhiber la proliferation cellulaire
CA2489251A1 (fr)	2002-07-05	2004-01-15	F. Hoffmann-La Roche Ag	Derives de quinazoline
AU2003253364B2 (en)	2002-08-07	2007-06-07	F. Hoffmann-La Roche Ag	Thiazole derivatives
WO2004024726A1 (fr)	2002-09-12	2004-03-25	F. Hoffmann-La Roche Ag	Composes d'acide 1h-indol-5-propionique a substitution n en tant qu'agonistes de ppar utiles dans le traitement du diabete
US6727277B1 (en)	2002-11-12	2004-04-27	Kansas State University Research Foundation	Compounds affecting cholesterol absorption
DE60323130D1 (de)	2002-11-25	2008-10-02	Hoffmann La Roche	Indolderivaten
GB0314967D0 (en)	2003-06-26	2003-07-30	Hoffmann La Roche	Piperazine derivatives
WO2005005403A2 (fr) *	2003-07-15	2005-01-20	Ranbaxy Laboratories Limited	Procede de preparation d'oxetan-2-ones
CN100393718C (zh)	2003-08-12	2008-06-11	霍夫曼-拉罗奇有限公司	作为npy拮抗剂的噻唑衍生物
CA2533463A1 (fr)	2003-08-12	2005-02-17	F. Hoffmann-La Roche Ag	Antagonistes 2-amino-5-benzoylthiazole du 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 (fr) *	2004-09-27	2006-04-06	Ranbaxy Laboratories Limited	Procede de preparation d'un derive d'orlistat utile comme standard de reference dans la determination de la purete d'orlistat et procede de preparation d'orlistat
CA2609634C (fr)	2005-05-03	2011-02-01	F. Hoffmann-La Roche Ag	Azapyrazinoindolines tetracycliques constituant des ligands 5-ht2
DE602006006712D1 (de)	2005-08-18	2009-06-18	Hoffmann La Roche	Thiazolylpiperidin-derivate nützlich als h3 rezeptor modulatoren
US20090171104A1 (en) *	2005-10-05	2009-07-02	Killol Patel	Process for the preparation of orlistat
ATE507222T1 (de)	2005-11-30	2011-05-15	Hoffmann La Roche	1,1-dioxo-thiomorpholinyl-indolyl-methanon- derivate zur verwendung als h3-modulatoren
CA2630270A1 (fr)	2005-11-30	2007-06-07	F. Hoffmann-La Roche Ag	Derives de indole-2-carboxamide substitues en 5
DE602006020482D1 (de)	2005-11-30	2011-04-14	Hoffmann La Roche	1,5-substituierte indol-2-yl amidderivative
ES2333672T3 (es)	2005-12-09	2010-02-25	F. Hoffmann-La Roche Ag	Derivados de amida triciclica para tratamiento de obesidad.
CN101326187A (zh)	2005-12-15	2008-12-17	霍夫曼-拉罗奇有限公司	吡咯并[2,3-c]吡啶衍生物
BRPI0619985A2 (pt)	2005-12-16	2011-10-25	Hoffmann La Roche	compostos, processo para a sua manufatura, composições farmacêuticas, métodos para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação de receptores de h3, de obesidade e de diabetes do tipo ii em um ser humano ou animal e usos dos compostos
BRPI0707916A2 (pt) *	2006-01-13	2011-05-17	Hoffmann La Roche	compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem e uso destes compostos
KR101047274B1 (ko) *	2006-01-23	2011-07-06	에프. 호프만-라 로슈 아게	Ｈ3 수용체 활성을 갖는 사이클로헥실 설폰아마이드 유도체
US7432255B2 (en)	2006-05-16	2008-10-07	Hoffmann-La Roche Inc.	1H-indol-5-yl-piperazin-1-yl-methanone derivatives
EP2032554A1 (fr) *	2006-05-30	2009-03-11	F. Hoffmann-Roche AG	Dérivés de pipéridinylpyrimidine
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
WO2009013195A1 (fr)	2007-07-25	2009-01-29	F. Hoffmann-La Roche Ag	Dérivés d'amide d'acide benzofurane- et benzo[b]thiophène-2-carboxylique et leur utilisation comme modulateurs du récepteur h3 de l'histamine
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US8993509B2 (en)	2009-03-31	2015-03-31	Robert Zimmerman	Method for treatment of cachexia by administering inhibitors of adipose triglyceride lipase expression or activity
WO2010112569A1 (fr)	2009-03-31	2010-10-07	Robert Zimmermann	Modulation de lipase de triglycérides d'adipose pour la prévention et le traitement d'une cachexie, d'une perte de poids et d'une atrophie musculaire et procédés de criblage s'y rapportant
CA2798330A1 (fr)	2010-05-05	2011-11-10	Infinity Pharmaceuticals, Inc.	Tetrazolones utilises en tant qu'inhibiteurs d'acide gras synthase (fasn)
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EP3651784B1 (fr) *	2017-07-12	2022-09-28	Mayo Foundation for Medical Education and Research	Composés pour la réduction de lésions lipotoxiques
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

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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
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CA1247547A (fr) *	1983-06-22	1988-12-28	Paul Hadvary	Derives de leucine

1985
- 1985-11-12 CA CA000495058A patent/CA1270837A/fr 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 IL IL77338A patent/IL77338A/xx not_active IP Right Cessation
- 1985-12-16 AU AU51259/85A patent/AU583569B2/en not_active Expired
- 1985-12-17 EP EP85116096A patent/EP0185359B1/fr not_active Expired - Lifetime
- 1985-12-17 AT AT85116096T patent/ATE70061T1/de not_active IP Right Cessation
- 1985-12-17 DE DE8585116096T patent/DE3584829D1/de not_active Expired - Lifetime
- 1985-12-18 PH PH33205A patent/PH26291A/en unknown
- 1985-12-18 HU HU854832A patent/HU200172B/hu unknown
- 1985-12-18 MC MC851814A patent/MC1728A1/fr unknown
- 1985-12-19 CN CN85108888A patent/CN1012643B/zh not_active Expired
- 1985-12-20 PT PT81748A patent/PT81748B/pt unknown
- 1985-12-20 NO NO855213A patent/NO171160C/no not_active IP Right Cessation
- 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
- 1985-12-30 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
US5175186A (en)	1992-12-29
ZW20385A1 (en)	1986-03-05
DK600385D0 (da)	1985-12-20
CN1012643B (zh)	1991-05-22
AU583569B2 (en)	1989-05-04
HUT39440A (en)	1986-09-29
IE58926B1 (en)	1993-12-01
EP0185359A3 (en)	1987-08-26
DK166724B1 (da)	1993-07-05
US4931463A (en)	1990-06-05
DK600385A (da)	1986-06-22
HU200172B (en)	1990-04-28
CN85108888A (zh)	1986-07-09
IL77338A (en)	1991-04-15
NO171160C (no)	1993-02-03
MC1728A1 (fr)	1986-12-15
FI854797A7 (fi)	1986-06-22
EP0185359A2 (fr)	1986-06-25
IE853277L (en)	1986-06-21
NZ214565A (en)	1989-06-28
NO855213L (no)	1986-06-23
NO171160B (no)	1992-10-26
AU5125985A (en)	1986-06-26
PT81748A (en)	1986-01-02
FI854797A0 (fi)	1985-12-04
CA1270837A (fr)	1990-06-26
CS262425B2 (en)	1989-03-14
ATE70061T1 (de)	1991-12-15
FI91403B (fi)	1994-03-15
DOP1985004386A (es)	1991-04-20
DE3584829D1 (de)	1992-01-16
FI91403C (fi)	1994-06-27
PT81748B (pt)	1988-07-29
EP0185359B1 (fr)	1991-12-04

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Clive et al.	1990	Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special titanium reagent for dicarbonyl coupling
Rojo et al.	1993	Stereoselective synthesis of substituted γ-butyrolactones from γ-hydroxy-α, β-unsaturated phenyl sulfones
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DE2629644A1 (de)	1977-01-20	16,16-spirocycloalkylprostaglandine und verfahren zu ihrer herstellung
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KR950008310B1 (ko)	1995-07-27	옥세타논의 제조방법
Domínguez et al.	1994	Flexible and stereoselective construction of polypropionate chains from enantiomerically pure γ-hydroxy-α, β-unsaturated sulfones
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US5216177A (en)	1993-06-01	Method of preparing trans-3,4-disubstituted-γ-lactones
GB2270914A (en)	1994-03-30	HIV protease inhibitor compounds
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US4107441A (en)	1978-08-15	Novel 16 hydroxy 15-deoxy-5-cis-prostenoic acids and esters
US4005106A (en)	1977-01-25	3β-[(Methoxalyl)oxy]-2α-(3-oxo-1-octenyl)-5-oxo-1β-cyclopentaneheptanoic acid and process
HU192316B (en)	1987-05-28	Process for producing new carbacyclin derivatives and pharmaceutical compositions containing them
JPH03220158A (ja)	1991-09-27	光学活性カルバサイクリン誘導体の製造方法
US3992412A (en)	1976-11-16	2α-(2-Carboxy-2-oxoethyl)-3β-hydroxy-5-oxo-1β-cyclopentaneheptanoic acid and process
JPH0645575B2 (ja)	1994-06-15	３―メチレン―２，６，７―三置換ビシクロ［３．３．０オクタン類
EP0084408A1 (fr)	1983-07-27	Composés du bicyclooctane, leur préparation et utilisation