NO314265B1 - Fremgangsmåte for fremstilling av organiske azider - Google Patents

Fremgangsmåte for fremstilling av organiske azider Download PDF

Info

Publication number: NO314265B1
Authority: NO; Norway
Prior art keywords: azide; reaction; derivative; organic compound; phenylmethyl
Prior art date: 1999-02-19

Application number

NO20000805A

Other languages

English (en)

Norwegian (no)

Other versions

NO20000805L (no

NO20000805D0 (no

Inventor

Henricus Cornelis Joz Claassen

Original Assignee

Sanofi Synthelabo

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.)

1999-02-19

Filing date

2000-02-18

Publication date

2003-02-24

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8239903&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO314265(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-02-18 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

2000-02-18 Publication of NO20000805D0 publication Critical patent/NO20000805D0/no

2000-08-21 Publication of NO20000805L publication Critical patent/NO20000805L/no

2003-02-24 Publication of NO314265B1 publication Critical patent/NO314265B1/no

Links

238000000034 method Methods 0.000 title claims description 25
150000001540 azides Chemical class 0.000 title claims description 16
238000006243 chemical reaction Methods 0.000 claims description 25
-1 alkali metal azide salt Chemical class 0.000 claims description 13
150000002894 organic compounds Chemical class 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
150000001720 carbohydrates Chemical class 0.000 claims description 5
UKGCFMYYDATGNN-UHFFFAOYSA-N 6,6a-dihydro-1ah-indeno[1,2-b]oxirene Chemical class C12=CC=CC=C2CC2C1O2 UKGCFMYYDATGNN-UHFFFAOYSA-N 0.000 claims description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical class C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
239000004593 Epoxy Chemical class 0.000 claims description 3
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical class CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
150000002924 oxiranes Chemical class 0.000 claims 5
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical group CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
150000002118 epoxides Chemical class 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000000203 mixture Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
239000002360 explosive Substances 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000007259 addition reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000011521 glass Substances 0.000 description 3
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 3
NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
150000000179 1,2-aminoalcohols Chemical class 0.000 description 1
GGUSIXKVMSRGIH-UHFFFAOYSA-N 1-azido-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2C(N=[N+]=[N-])C(O)CC2=C1 GGUSIXKVMSRGIH-UHFFFAOYSA-N 0.000 description 1
ZGESFQWNGRLQLH-UHFFFAOYSA-N 1-azido-3-propan-2-yloxypropan-2-ol Chemical compound CC(C)OCC(O)CN=[N+]=[N-] ZGESFQWNGRLQLH-UHFFFAOYSA-N 0.000 description 1
RBBIKFDLPCEOTF-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C(C(C)C)=C1C(C)C RBBIKFDLPCEOTF-UHFFFAOYSA-N 0.000 description 1
MALKRPRQNKEVSK-UHFFFAOYSA-N 2-azido-1-phenylethanol Chemical compound [N-]=[N+]=NCC(O)C1=CC=CC=C1 MALKRPRQNKEVSK-UHFFFAOYSA-N 0.000 description 1
GXARJZSMOVQDPH-UHFFFAOYSA-N 2-azido-2,3-dihydro-1h-inden-1-ol Chemical compound C1=CC=C2C(O)C(N=[N+]=[N-])CC2=C1 GXARJZSMOVQDPH-UHFFFAOYSA-N 0.000 description 1
IAMPGUPDKQOGBT-UHFFFAOYSA-N 2-azido-2-phenylethanol Chemical compound [N-]=[N+]=NC(CO)C1=CC=CC=C1 IAMPGUPDKQOGBT-UHFFFAOYSA-N 0.000 description 1
ZZRATGGUCCHLQZ-UHFFFAOYSA-N 2-azido-3-propan-2-yloxypropan-1-ol Chemical compound CC(C)OCC(CO)N=[N+]=[N-] ZZRATGGUCCHLQZ-UHFFFAOYSA-N 0.000 description 1
QECSGTHYJAPXMH-UHFFFAOYSA-N 2-azidocyclohexan-1-ol Chemical compound OC1CCCCC1N=[N+]=[N-] QECSGTHYJAPXMH-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229920002683 Glycosaminoglycan Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 1
229940006460 bromide ion Drugs 0.000 description 1
239000000872 buffer Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
150000001719 carbohydrate derivatives Chemical class 0.000 description 1
229940077731 carbohydrate nutrients Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000003712 glycosamine group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
JRUBGUVYQMKOMK-UHFFFAOYSA-N nickel(2+) diazide Chemical class [Ni+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] JRUBGUVYQMKOMK-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 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
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO20000805A 1999-02-19 2000-02-18 Fremgangsmåte for fremstilling av organiske azider NO314265B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP99200484		1999-02-19

Publications (3)

Publication Number	Publication Date
NO20000805D0 NO20000805D0 (no)	2000-02-18
NO20000805L NO20000805L (no)	2000-08-21
NO314265B1 true NO314265B1 (no)	2003-02-24

Family

ID=8239903

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20000805A NO314265B1 (no)	1999-02-19	2000-02-18	Fremgangsmåte for fremstilling av organiske azider

Country Status (23)

Country	Link
US (1)	US6232451B1 (tr)
EP (1)	EP1029867B1 (tr)
JP (1)	JP4347488B2 (tr)
KR (1)	KR100649058B1 (tr)
CN (1)	CN1156483C (tr)
AR (1)	AR022615A1 (tr)
AT (1)	ATE265463T1 (tr)
AU (1)	AU769027B2 (tr)
BR (1)	BRPI0000481B8 (tr)
CA (1)	CA2296902C (tr)
CZ (1)	CZ298569B6 (tr)
DE (1)	DE60010147T2 (tr)
DK (1)	DK1029867T3 (tr)
ES (1)	ES2216810T3 (tr)
HU (1)	HUP0000740A3 (tr)
IL (1)	IL134144A (tr)
NO (1)	NO314265B1 (tr)
NZ (1)	NZ502829A (tr)
PL (1)	PL198390B1 (tr)
PT (1)	PT1029867E (tr)
RU (1)	RU2241714C2 (tr)
TR (1)	TR200000441A2 (tr)
ZA (1)	ZA200000578B (tr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8242344B2 (en) *	2002-06-26	2012-08-14	Fingersteps, Inc.	Method and apparatus for composing and performing music
FR2935976B1 (fr) *	2008-09-16	2010-12-17	Sanofi Aventis	Voie courte de synthese du 1,6:2,3-dianhydro-b-d- mannopyranose.
FR2935975B1 (fr) *	2008-09-16	2010-12-17	Sanofi Aventis	Procede de preparation du 1,6:2,3-dianhydro-b-d- mannopyranose.
CN103819357B (zh) *	2014-01-28	2016-03-16	浙江大学	(-)-有效霉醇叠氮四乙酸酯的制备方法
US11708320B2 (en)	2018-06-29	2023-07-25	Georgia State University Research Foundation, Inc.	Environmentally-friendly hydroazidation of olefins

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3893997A (en)	1974-07-01	1975-07-08	Smithkline Corp	Pseudodisaccharide intermediates
CS191047B1 (en) *	1977-09-05	1979-06-29	Alzbeta Krutosikova	Ethylesters of 3-/5-aryl-2-furyl/-2-azidoacrylic acids and method for their preparing
US4582918A (en) *	1984-09-19	1986-04-15	Schering Corporation	Preparation of intermediates for (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols
CS276874B6 (cs) *	1990-09-11	1992-08-12	Ustav Organicke Chemie A Bioch	l-(3-azido-2,3-dideoxy-Beta-D-allokofuranosylJthymin, způsob jeho přípravy a použití
US5206251A (en) *	1992-04-01	1993-04-27	G. D. Searle & Co.	2- and 3- amino and azido derivatives of 1,5-iminosugars
JPH08332095A (ja) *	1995-06-06	1996-12-17	Chisso Corp	インデノールの製造法

2000
- 2000-01-20 IL IL13414400A patent/IL134144A/en not_active IP Right Cessation
- 2000-01-21 CA CA002296902A patent/CA2296902C/en not_active Expired - Lifetime
- 2000-02-08 ZA ZA200000578A patent/ZA200000578B/xx unknown
- 2000-02-08 AU AU14965/00A patent/AU769027B2/en not_active Expired
- 2000-02-08 US US09/499,685 patent/US6232451B1/en not_active Expired - Lifetime
- 2000-02-14 DK DK00200466T patent/DK1029867T3/da active
- 2000-02-14 EP EP00200466A patent/EP1029867B1/en not_active Expired - Lifetime
- 2000-02-14 ES ES00200466T patent/ES2216810T3/es not_active Expired - Lifetime
- 2000-02-14 NZ NZ502829A patent/NZ502829A/en not_active IP Right Cessation
- 2000-02-14 DE DE60010147T patent/DE60010147T2/de not_active Expired - Lifetime
- 2000-02-14 AT AT00200466T patent/ATE265463T1/de active
- 2000-02-14 PT PT00200466T patent/PT1029867E/pt unknown
- 2000-02-16 JP JP2000037510A patent/JP4347488B2/ja not_active Expired - Lifetime
- 2000-02-17 TR TR2000/00441A patent/TR200000441A2/tr unknown
- 2000-02-17 BR BRPI0000481A patent/BRPI0000481B8/pt not_active IP Right Cessation
- 2000-02-17 AR ARP000100667A patent/AR022615A1/es active IP Right Grant
- 2000-02-18 PL PL338501A patent/PL198390B1/pl unknown
- 2000-02-18 CZ CZ20000588A patent/CZ298569B6/cs not_active IP Right Cessation
- 2000-02-18 HU HU0000740A patent/HUP0000740A3/hu unknown
- 2000-02-18 RU RU2000104086/04A patent/RU2241714C2/ru active
- 2000-02-18 CN CNB001022385A patent/CN1156483C/zh not_active Expired - Lifetime
- 2000-02-18 NO NO20000805A patent/NO314265B1/no not_active IP Right Cessation
- 2000-02-18 KR KR1020000007790A patent/KR100649058B1/ko active IP Right Grant

Also Published As

Publication number	Publication date
KR100649058B1 (ko)	2006-11-24
AU1496500A (en)	2000-08-24
NO20000805L (no)	2000-08-21
BRPI0000481B8 (pt)	2021-05-25
IL134144A (en)	2004-02-08
TR200000441A3 (tr)	2000-09-21
KR20010029568A (ko)	2001-04-06
JP4347488B2 (ja)	2009-10-21
EP1029867A3 (en)	2001-03-14
DE60010147T2 (de)	2005-06-09
CN1156483C (zh)	2004-07-07
PT1029867E (pt)	2004-08-31
ATE265463T1 (de)	2004-05-15
HUP0000740A3 (en)	2002-03-28
CA2296902A1 (en)	2000-08-19
CZ298569B6 (cs)	2007-11-07
IL134144A0 (en)	2001-04-30
AR022615A1 (es)	2002-09-04
CA2296902C (en)	2009-02-24
NO20000805D0 (no)	2000-02-18
EP1029867A2 (en)	2000-08-23
DE60010147D1 (de)	2004-06-03
CN1263892A (zh)	2000-08-23
PL198390B1 (pl)	2008-06-30
BR0000481B1 (pt)	2013-11-26
PL338501A1 (en)	2000-08-28
TR200000441A2 (tr)	2000-09-21
ES2216810T3 (es)	2004-11-01
EP1029867B1 (en)	2004-04-28
HU0000740D0 (en)	2000-04-28
AU769027B2 (en)	2004-01-15
CZ2000588A3 (cs)	2000-10-11
RU2241714C2 (ru)	2004-12-10
US6232451B1 (en)	2001-05-15
DK1029867T3 (da)	2004-08-16
ZA200000578B (en)	2000-09-07
BR0000481A (pt)	2000-09-12
NZ502829A (en)	2001-06-29
JP2000302740A (ja)	2000-10-31
HUP0000740A2 (en)	2001-03-28

Legal Events

Date	Code	Title	Description
2020-03-09	MK1K	Patent expired

Publication	Publication Date	Title
DK166827B1 (da)	1993-07-19	Saccharosealkyl-4,6-orthoestere og en fremgangsmaade til fremstilling af saccharose-6-estere
Baker et al.	1955	Puromycin. Synthetic Studies. XV. 3'-Amino-3'-deoxyadenosine
FI83783C (fi)	1991-08-26	Foerfarande foer framstaellning av 1,6-diklor-1,6-dideoxi- -d-fruktofuranosyl-4-klor-4-deoxi- -galaktopyranosider.
EP1246831B1 (en)	2008-03-05	Preparation method of azithromycin dihydrate
GB2047247A (en)	1980-11-26	11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyloxacyclopentadecane-2-one and derivatives thereof as well as processes for their preparation
NO180010B (no)	1996-10-21	Fremgangsmåte for fremstilling av sukrose-6-ester
JPH07501317A (ja)	1995-02-09	モルフィン−６−グルクロナイドあるいは置換モルフィン−６−グルクロナイドの製法
EP3819302B1 (en)	2022-10-19	Fucosylated chondroitin sulfate oligosaccharide, preparation method therefor, composition thereof and use thereof
Hu et al.	2017	A flexible 1, 2-cis α-glycosylation strategy based on in situ adduct transformation
NO314265B1 (no)	2003-02-24	Fremgangsmåte for fremstilling av organiske azider
WO2009007988A1 (en)	2009-01-15	Process for the preparation of 6-o-methylerythromycin a 9-oxime
CZ96799A3 (cs)	1999-11-17	Sloučenina 6-O-methylerytromycin A 9-hydrazon, způsob přípravy 6-O-methylerytromycin A 9-hydrazonu a způsob přípravy 6-O-methylerytromycin A 9-oximu
FI72523B (fi)	1987-02-27	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara aminocyklitderivat.
JPH10502093A (ja)	1998-02-24	レジオ選択的硫酸化
MXPA00001753A (en)	2002-06-05	Process for the preparation of organic azides
Cmoch et al.	2008	Comparative investigations on the regioselective mannosylation of 2, 3, 4-triols of mannose
US5910579A (en)	1999-06-08	Processes for the preparation of αGal(1->4)βGal (1->4) Glc-OR
Hough et al.	1967	4, 6-Anhydro derivatives of L-xylo-hexulofuranose
Kaylor et al.	1995	A new model compound for studying alkaline cellulose chain cleavage reactions
US7919599B2 (en)	2011-04-05	Production of L-iduronate containing polysaccharides
White	1942	The Constitution of Arabo-galactan. III. The Location of the Arabinose Component
Ac	0	anomeric configuration and conformation of iV-acetyl bis (2, 3í4-tri-0-acetyl-/3-L-rhamnopyranosyl) amine un-derivative IV was found to be identical with that of der the same reaction conditions as described with compound II [1, 3]. compound II (Scheme 2). The 13C NMR spectrum of iV-Acetyl-bis (2, 3, 4-tri-0-acetyl-iS-L-rhamnopyrano-compound V7 (CDC13, 25 C) disclosed only one a little syl) amine (VI) was synthesized by 7V-acetylation of broadened signal of the anomeric carbon at 6= 80.5
HUT75517A (en)	1997-05-28	New synthesis of 17beta-cyano-3-ethoxy-17alfa-hydroxy-6-methylandrosta-3,5,9(11)-triene and its -17-one intermediate
PL166395B1 (pl)	1995-05-31	Sposób wytwarzania nowych oksymów oleandomycyny PL PL PL PL PL