BG64050B1 - Метод за получаване на аминопроизводни на алкилоксифуранон, съединения, получени по този метод, и тяхното използване - Google Patents

Метод за получаване на аминопроизводни на алкилоксифуранон, съединения, получени по този метод, и тяхното използване Download PDF

Info

Publication number: BG64050B1
Authority: BG; Bulgaria
Prior art keywords: formula; acid; compounds; compound; salt
Prior art date: 1997-07-15

Application number

BG104073A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG104073A (en

Inventor

Raphael Bouchet

Francis Brion

Colette Colladant

Jacques Lagouardat

Original Assignee

Hoechst Marion Roussel

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.)

1997-07-15

Filing date

2000-01-12

Publication date

2003-11-28

2000-01-12 Application filed by Hoechst Marion Roussel filed Critical Hoechst Marion Roussel

2001-05-31 Publication of BG104073A publication Critical patent/BG104073A/xx

2003-11-28 Publication of BG64050B1 publication Critical patent/BG64050B1/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 100
238000000034 method Methods 0.000 title claims abstract description 48
-1 aminoderivatives of alkyloxy furanone derivatives Chemical class 0.000 title 1
230000015572 biosynthetic process Effects 0.000 claims abstract description 6
238000003786 synthesis reaction Methods 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 26
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 24
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 17
238000002425 crystallisation Methods 0.000 claims description 17
230000008025 crystallization Effects 0.000 claims description 17
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
238000006345 epimerization reaction Methods 0.000 claims description 14
238000000926 separation method Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
238000007327 hydrogenolysis reaction Methods 0.000 claims description 11
229940098779 methanesulfonic acid Drugs 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229960005215 dichloroacetic acid Drugs 0.000 claims description 8
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 claims description 8
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 7
108090000790 Enzymes Proteins 0.000 claims description 7
102000004190 Enzymes Human genes 0.000 claims description 7
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000003884 phenylalkyl group Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
102000015696 Interleukins Human genes 0.000 claims description 3
108010063738 Interleukins Proteins 0.000 claims description 3
150000004982 aromatic amines Chemical class 0.000 claims description 3
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000007112 amidation reaction Methods 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000000543 intermediate Substances 0.000 claims description 2
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 3
108090000426 Caspase-1 Proteins 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000012298 atmosphere Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000005406 washing Methods 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
TVWOUZGPAISBIW-UHFFFAOYSA-N 3-(1-phenylethylamino)-3H-furan-2-one Chemical compound C1(=CC=CC=C1)C(C)NC1C(OC=C1)=O TVWOUZGPAISBIW-UHFFFAOYSA-N 0.000 description 3
MCYUQYQRIJUWMW-UHFFFAOYSA-N 3-ethoxy-3h-furan-2-one Chemical compound CCOC1C=COC1=O MCYUQYQRIJUWMW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 3
229940089960 chloroacetate Drugs 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 2
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 2
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
102000003777 Interleukin-1 beta Human genes 0.000 description 2
108090000193 Interleukin-1 beta Proteins 0.000 description 2
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229960005261 aspartic acid Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
102100029368 Cytochrome P450 2C18 Human genes 0.000 description 1
241001649081 Dina Species 0.000 description 1
101000919360 Homo sapiens Cytochrome P450 2C18 Proteins 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
238000006957 Michael reaction Methods 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012069 chiral reagent Substances 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940120124 dichloroacetate Drugs 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-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
- C07D307/30—Heterocyclic compounds containing five-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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-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
- C07D307/30—Heterocyclic compounds containing five-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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-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
- C07D307/30—Heterocyclic compounds containing five-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
- C07D307/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

BG104073A 1997-07-15 2000-01-12 Метод за получаване на аминопроизводни на алкилоксифуранон, съединения, получени по този метод, и тяхното използване BG64050B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9708932A FR2766188B1 (fr)	1997-07-15	1997-07-15	Nouveau procede de preparation de derives amines d'alkyloxy furanone, composes issus de ce procede et utilisation de ces composes
PCT/FR1998/001480 WO1999003852A1 (fr)	1997-07-15	1998-07-09	Procede de preparation de derives amines d'alkyloxyfuranone, composes issus de ce procede et utilisation de ces composes

Publications (2)

Publication Number	Publication Date
BG104073A BG104073A (en)	2001-05-31
BG64050B1 true BG64050B1 (bg)	2003-11-28

Family

ID=9509210

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104073A BG64050B1 (bg)	1997-07-15	2000-01-12	Метод за получаване на аминопроизводни на алкилоксифуранон, съединения, получени по този метод, и тяхното използване

Country Status (34)

Country	Link
US (1)	US6235899B1 (sr)
EP (1)	EP0998470B1 (sr)
JP (1)	JP4450987B2 (sr)
KR (1)	KR100519691B1 (sr)
CN (1)	CN100363355C (sr)
AP (1)	AP1071A (sr)
AR (1)	AR015924A1 (sr)
AT (1)	ATE239713T1 (sr)
AU (1)	AU744272B2 (sr)
BG (1)	BG64050B1 (sr)
BR (1)	BR9810896A (sr)
CA (1)	CA2296742C (sr)
CZ (1)	CZ295312B6 (sr)
DE (1)	DE69814395T2 (sr)
DK (1)	DK0998470T3 (sr)
EA (1)	EA002883B1 (sr)
EE (1)	EE03873B1 (sr)
ES (1)	ES2197489T3 (sr)
FR (1)	FR2766188B1 (sr)
HR (1)	HRP20000027B1 (sr)
HU (1)	HU230148B1 (sr)
ID (1)	ID23784A (sr)
IL (1)	IL134031A (sr)
ME (1)	ME01708B (sr)
NO (1)	NO324508B1 (sr)
NZ (1)	NZ502338A (sr)
PL (1)	PL200820B1 (sr)
PT (1)	PT998470E (sr)
RS (1)	RS49832B (sr)
SK (1)	SK284168B6 (sr)
TR (1)	TR200000117T2 (sr)
UA (1)	UA66364C2 (sr)
WO (1)	WO1999003852A1 (sr)
ZA (1)	ZA986203B (sr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7053056B2 (en) *	1998-07-02	2006-05-30	Idun Pharmaceuticals, Inc.	C-terminal modified oxamyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases
ES2347133T3 (es) *	2000-04-24	2010-10-26	Vertex Pharmaceuticals Incorporated	Procedimiento e intermedios para preparar acetales de acido aspartico sustituidos.
PE20011350A1 (es)	2000-05-19	2002-01-15	Vertex Pharma	PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE)
JP2003327568A (ja) *	2000-09-20	2003-11-19	Kanegafuchi Chem Ind Co Ltd	光学活性β−アミノ酸誘導体の製造方法
WO2002055478A1 (fr) *	2001-01-16	2002-07-18	Kaneka Corporation	Procede de preparation de derives d'aminolactone optiquement actifs et intermediaires de ces derives
CN102161656B (zh)	2004-02-27	2013-02-20	沃泰克斯药物股份有限公司	天冬氨酸特异性半胱氨酸蛋白酶抑制剂及其用途
DK1725548T3 (en) *	2004-03-12	2015-03-23	Vertex Pharma	Process and intermediates for the preparation of asparagine acetal caspase inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6204261B1 (en) *	1995-12-20	2001-03-20	Vertex Pharmaceuticals Incorporated	Inhibitors of interleukin-1β Converting enzyme inhibitors
US5716929A (en) *	1994-06-17	1998-02-10	Vertex Pharmaceuticals, Inc.	Inhibitors of interleukin-1β converting enzyme

1997
- 1997-07-15 FR FR9708932A patent/FR2766188B1/fr not_active Expired - Lifetime
1998
- 1998-07-09 PL PL338035A patent/PL200820B1/pl unknown
- 1998-07-09 CZ CZ200065A patent/CZ295312B6/cs not_active IP Right Cessation
- 1998-07-09 US US09/463,014 patent/US6235899B1/en not_active Expired - Lifetime
- 1998-07-09 BR BR9810896-4A patent/BR9810896A/pt not_active Application Discontinuation
- 1998-07-09 KR KR10-2000-7000398A patent/KR100519691B1/ko not_active Expired - Lifetime
- 1998-07-09 AU AU86333/98A patent/AU744272B2/en not_active Expired
- 1998-07-09 EP EP98937591A patent/EP0998470B1/fr not_active Expired - Lifetime
- 1998-07-09 DK DK98937591T patent/DK0998470T3/da active
- 1998-07-09 AT AT98937591T patent/ATE239713T1/de active
- 1998-07-09 EE EEP200000024A patent/EE03873B1/xx unknown
- 1998-07-09 NZ NZ502338A patent/NZ502338A/en not_active IP Right Cessation
- 1998-07-09 TR TR2000/00117T patent/TR200000117T2/xx unknown
- 1998-07-09 JP JP2000503076A patent/JP4450987B2/ja not_active Expired - Lifetime
- 1998-07-09 HU HU0003857A patent/HU230148B1/hu unknown
- 1998-07-09 EA EA200000127A patent/EA002883B1/ru not_active IP Right Cessation
- 1998-07-09 PT PT98937591T patent/PT998470E/pt unknown
- 1998-07-09 WO PCT/FR1998/001480 patent/WO1999003852A1/fr active IP Right Grant
- 1998-07-09 SK SK30-2000A patent/SK284168B6/sk not_active IP Right Cessation
- 1998-07-09 HR HR20000027A patent/HRP20000027B1/xx not_active IP Right Cessation
- 1998-07-09 ES ES98937591T patent/ES2197489T3/es not_active Expired - Lifetime
- 1998-07-09 AP APAP/P/2000/001732A patent/AP1071A/en active
- 1998-07-09 CA CA002296742A patent/CA2296742C/fr not_active Expired - Lifetime
- 1998-07-09 CN CNB98808967XA patent/CN100363355C/zh not_active Expired - Lifetime
- 1998-07-09 ID IDW20000067A patent/ID23784A/id unknown
- 1998-07-09 RS YUP-15/00A patent/RS49832B/sr unknown
- 1998-07-09 ME MEP-2000-15A patent/ME01708B/me unknown
- 1998-07-09 IL IL13403198A patent/IL134031A/en not_active IP Right Cessation
- 1998-07-09 DE DE69814395T patent/DE69814395T2/de not_active Expired - Lifetime
- 1998-07-13 ZA ZA9806203A patent/ZA986203B/xx unknown
- 1998-07-15 AR ARP980103455A patent/AR015924A1/es not_active Application Discontinuation
- 1998-09-07 UA UA2000020800A patent/UA66364C2/uk unknown
2000
- 2000-01-12 BG BG104073A patent/BG64050B1/bg unknown
- 2000-01-14 NO NO20000182A patent/NO324508B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2766188A1 (fr)	1999-01-22
RS49832B (sr)	2008-08-07
SK302000A3 (en)	2000-11-07
IL134031A0 (en)	2001-04-30
AR015924A1 (es)	2001-05-30
ID23784A (id)	2000-05-11
ES2197489T3 (es)	2004-01-01
EA002883B1 (ru)	2002-10-31
SK284168B6 (sk)	2004-10-05
AP2000001732A0 (en)	2000-03-31
PL338035A1 (en)	2000-09-25
HUP0003857A2 (hu)	2001-04-28
DE69814395D1 (de)	2003-06-12
CZ200065A3 (cs)	2000-07-12
UA66364C2 (uk)	2004-05-17
ZA986203B (en)	1999-08-18
HRP20000027A2 (en)	2000-10-31
AU8633398A (en)	1999-02-10
TR200000117T2 (tr)	2000-07-21
ATE239713T1 (de)	2003-05-15
CN1269795A (zh)	2000-10-11
CA2296742C (fr)	2009-12-08
JP2001510191A (ja)	2001-07-31
AP1071A (en)	2002-05-20
AU744272B2 (en)	2002-02-21
KR20010021834A (ko)	2001-03-15
NZ502338A (en)	2001-09-28
FR2766188B1 (fr)	2000-02-11
IL134031A (en)	2004-06-01
EP0998470A1 (fr)	2000-05-10
BG104073A (en)	2001-05-31
HU230148B1 (hu)	2015-09-28
EA200000127A1 (ru)	2000-08-28
HRP20000027B1 (en)	2006-07-31
NO20000182L (no)	2000-03-07
ME01708B (me)	2008-08-07
CA2296742A1 (fr)	1999-01-28
KR100519691B1 (ko)	2005-10-13
BR9810896A (pt)	2000-09-26
JP4450987B2 (ja)	2010-04-14
YU1500A (sh)	2002-10-18
US6235899B1 (en)	2001-05-22
CN100363355C (zh)	2008-01-23
HUP0003857A3 (en)	2002-08-28
NO20000182D0 (no)	2000-01-14
NO324508B1 (no)	2007-11-05
DE69814395T2 (de)	2003-12-11
WO1999003852A1 (fr)	1999-01-28
PT998470E (pt)	2003-09-30
EP0998470B1 (fr)	2003-05-07
EE200000024A (et)	2000-10-16
CZ295312B6 (cs)	2005-07-13
PL200820B1 (pl)	2009-02-27
DK0998470T3 (da)	2003-09-01
EE03873B1 (et)	2002-10-15

Publication	Publication Date	Title
CN102209707B (zh)	2014-07-09	制备氨基酸衍生物的新方法
JP2818958B2 (ja)	1998-10-30	４―（４―アルコキシフェニル）―２―ブチルアミン誘導体およびその製造法
EP0340064A1 (fr)	1989-11-02	Benzodiazépines, leur procédé et intermédiaires de préparation et leurs applications en thérapeutique
US5847169A (en)	1998-12-08	Process for preparing oxiranemethanamine derivatives
HU186776B (en)	1985-09-30	Process for preparing new, optically active imidazolidin-2-one derivatives
BG64050B1 (bg)	2003-11-28	Метод за получаване на аминопроизводни на алкилоксифуранон, съединения, получени по този метод, и тяхното използване
JP2004508375A (ja)	2004-03-18	４−（Ｎ−アルキルアミノ）−５，６−ジヒドロ−４Ｈ−チエン−（２，３−ｂ）−チオピラン−２−スルホンアミド−７，７−ジオキシドおよび中間体を得る方法
GB1598667A (en)	1981-09-23	1,3-dioxolane derivatives and their use in the preparation of 1-amino-3-aryloxy-2-propanols
JPH03271269A (ja)	1991-12-03	カルシウム管遮断剤の製造に用いるキラル中間体の分割法
JP3965450B2 (ja)	2007-08-29	α−置換されたアクリル酸誘導体からＮ−（メルカプトアシル）アミノ酸を合成する方法
Pyne et al.	1998	Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones
CN112272665B (zh)	2024-07-12	制备立他司特的方法
EP1163223A1 (en)	2001-12-19	Synthesis of 3-amino-3-aryl propanoates
KR100434915B1 (ko)	2004-10-20	광학활성시아노히드린의제조방법
US5959141A (en)	1999-09-28	1-amino-2-hydroxycycloalkanecarboxylic acid derivatives
KR100523321B1 (ko)	2005-10-24	4-히드록시-2-피롤리디논의 제조방법
JPH10237013A (ja)	1998-09-08	光学活性２−ベンジルコハク酸の製造法
JP3832919B2 (ja)	2006-10-11	光学活性シアンヒドリンの製造法
JPH0822855B2 (ja)	1996-03-06	光学活性なヒスチジン誘導体
KR19990014746A (ko)	1999-02-25	광학 활성 아미노인단올의 합성
MXPA00000506A (en)	2001-05-07	Method for preparing alkyloxy furanone derivatives, compounds obtained by said method and use of said compounds
FR2629453A1 (fr)	1989-10-06	Procede pour la preparation de phenylethanolaminotetralines
JPH07206793A (ja)	1995-08-08	光学活性２−メチルスレオニン及び２−メチルアロスレオニン及びその製造法