IL114246A - Method for the purification of 23-E isomers of 23-Imino derivatives of LL-F28249 compounds - Google Patents

Method for the purification of 23-E isomers of 23-Imino derivatives of LL-F28249 compounds

Info

Publication number: IL114246A
Authority: IL; Israel
Prior art keywords: chloride; compound; carbamoyl; groups; methyl
Prior art date: 1994-06-22

Application number

IL11424695A

Other languages

English (en)

Other versions

IL114246A0 (en

Original Assignee

American Cyanamid Co

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.)

1994-06-22

Filing date

1995-06-21

Publication date

1998-10-30

1995-06-21 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1995-10-31 Publication of IL114246A0 publication Critical patent/IL114246A0/xx

1998-10-30 Publication of IL114246A publication Critical patent/IL114246A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 43
238000000034 method Methods 0.000 title claims abstract description 31
238000000746 purification Methods 0.000 title abstract description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
-1 C1-C4alkoxymethy„l Chemical group 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000003223 protective agent Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical group [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 5
125000006331 halo benzoyl group Chemical group 0.000 claims description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 claims description 2
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 claims description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
239000012346 acetyl chloride Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 2
PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000002585 base Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 3
239000004557 technical material Substances 0.000 description 3
SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 2
108010034145 Helminth Proteins Proteins 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
244000078703 ectoparasite Species 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
244000000013 helminth Species 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical group [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229940120124 dichloroacetate Drugs 0.000 description 1
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical group OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000463 material Substances 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical group COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
YNFMRVVYUVPIAN-AQUURSMBSA-N nemadectin Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C(C)C)O[C@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YNFMRVVYUVPIAN-AQUURSMBSA-N 0.000 description 1
YNFMRVVYUVPIAN-UHFFFAOYSA-N nemadectin alpha Natural products C1C(O)C(C)C(C(C)=CC(C)C)OC11OC(CC=C(C)CC(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 YNFMRVVYUVPIAN-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical group OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical group OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL11424695A 1994-06-22 1995-06-21 Method for the purification of 23-E isomers of 23-Imino derivatives of LL-F28249 compounds IL114246A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/263,967 US5478951A (en)	1994-06-22	1994-06-22	Method for the purification of 23-E isomers of 23-imino derivatives of LL-F28249 compounds

Publications (2)

Publication Number	Publication Date
IL114246A0 IL114246A0 (en)	1995-10-31
IL114246A true IL114246A (en)	1998-10-30

Family

ID=23004003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11424695A IL114246A (en)	1994-06-22	1995-06-21	Method for the purification of 23-E isomers of 23-Imino derivatives of LL-F28249 compounds

Country Status (20)

Country	Link
US (1)	US5478951A (de)
EP (1)	EP0688775B1 (de)
JP (1)	JP3817756B2 (de)
KR (1)	KR100367947B1 (de)
CN (1)	CN1063445C (de)
AT (1)	ATE214071T1 (de)
AU (1)	AU681785C (de)
BR (1)	BR9502869A (de)
CA (1)	CA2152249A1 (de)
CZ (1)	CZ288894B6 (de)
DE (1)	DE69525686T2 (de)
DK (1)	DK0688775T3 (de)
ES (1)	ES2172554T3 (de)
HU (1)	HU216278B (de)
IL (1)	IL114246A (de)
PT (1)	PT688775E (de)
SI (1)	SI0688775T1 (de)
SK (1)	SK283198B6 (de)
TW (1)	TW319770B (de)
ZA (1)	ZA955106B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7348417B2 (en) *	2003-08-07	2008-03-25	Wyeth	Method of purifying moxidectin through crystallization
CN104277050B (zh) *	2013-07-04	2016-05-04	北大方正集团有限公司	一种制备莫西克汀的方法
CN103601735B (zh) *	2013-11-08	2015-12-09	大连九信生物化工科技有限公司	一种提纯莫西克汀的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4916154A (en) *	1986-09-12	1990-04-10	American Cyanamid Company	23-Imino derivatives of LL-F28249 compounds
GB8721377D0 (en) *	1987-09-11	1987-10-21	Glaxo Group Ltd	Chemical compounds
NZ233680A (en) *	1989-05-17	1995-02-24	Beecham Group Plc	Avermectins and milbemycins and compositions thereof
US4988824A (en) *	1989-09-11	1991-01-29	Maulding Donald R	Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds

1994
- 1994-06-22 US US08/263,967 patent/US5478951A/en not_active Expired - Lifetime
1995
- 1995-06-14 CZ CZ19951538A patent/CZ288894B6/cs not_active IP Right Cessation
- 1995-06-16 JP JP17297395A patent/JP3817756B2/ja not_active Expired - Fee Related
- 1995-06-19 AT AT95304229T patent/ATE214071T1/de not_active IP Right Cessation
- 1995-06-19 SI SI9530546T patent/SI0688775T1/xx unknown
- 1995-06-19 PT PT95304229T patent/PT688775E/pt unknown
- 1995-06-19 EP EP95304229A patent/EP0688775B1/de not_active Expired - Lifetime
- 1995-06-19 DE DE69525686T patent/DE69525686T2/de not_active Expired - Lifetime
- 1995-06-19 ES ES95304229T patent/ES2172554T3/es not_active Expired - Lifetime
- 1995-06-19 DK DK95304229T patent/DK0688775T3/da active
- 1995-06-20 ZA ZA955106A patent/ZA955106B/xx unknown
- 1995-06-20 AU AU21766/95A patent/AU681785C/en not_active Ceased
- 1995-06-20 CA CA002152249A patent/CA2152249A1/en not_active Abandoned
- 1995-06-21 TW TW084106387A patent/TW319770B/zh not_active IP Right Cessation
- 1995-06-21 IL IL11424695A patent/IL114246A/en not_active IP Right Cessation
- 1995-06-21 HU HU9501834A patent/HU216278B/hu not_active IP Right Cessation
- 1995-06-21 KR KR1019950016676A patent/KR100367947B1/ko not_active Expired - Fee Related
- 1995-06-21 BR BR9502869A patent/BR9502869A/pt not_active IP Right Cessation
- 1995-06-21 CN CN95106465A patent/CN1063445C/zh not_active Expired - Fee Related
- 1995-06-22 SK SK824-95A patent/SK283198B6/sk not_active IP Right Cessation

Also Published As

Publication number	Publication date
BR9502869A (pt)	1996-11-05
AU681785B2 (en)	1997-09-04
PT688775E (pt)	2002-07-31
AU681785C (en)	2007-11-01
IL114246A0 (en)	1995-10-31
HUT72831A (en)	1996-05-28
TW319770B (de)	1997-11-11
JPH0853456A (ja)	1996-02-27
AU2176695A (en)	1996-01-04
SK283198B6 (sk)	2003-03-04
CN1117969A (zh)	1996-03-06
ZA955106B (en)	1996-12-20
KR100367947B1 (ko)	2003-03-26
CZ153895A3 (en)	1996-01-17
JP3817756B2 (ja)	2006-09-06
ES2172554T3 (es)	2002-10-01
KR960000890A (ko)	1996-01-25
HU216278B (hu)	1999-05-28
EP0688775A1 (de)	1995-12-27
SK82495A3 (en)	1996-01-10
CA2152249A1 (en)	1995-12-23
CZ288894B6 (cs)	2001-09-12
ATE214071T1 (de)	2002-03-15
DE69525686D1 (de)	2002-04-11
EP0688775B1 (de)	2002-03-06
CN1063445C (zh)	2001-03-21
DE69525686T2 (de)	2002-09-12
US5478951A (en)	1995-12-26
SI0688775T1 (en)	2002-06-30
DK0688775T3 (da)	2002-06-03
HU9501834D0 (en)	1995-08-28

Legal Events

Date	Code	Title
1999-03-12	FF	Patent granted
1999-08-17	KB	Patent renewed
2009-12-24	KB	Patent renewed
2014-01-30	MM9K	Patent not in force due to non-payment of renewal fees

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EP1067125B1 (de)	2006-07-26	VERFAHREN ZUR HERSTELLUNG VON threo-1,2-EPOXY-3-AMINO-4-PHENYLBUTAN-DERIVATEN
WO1996029072A1 (en)	1996-09-26	Anthelmintic use of nodulisporic acid and analogs thereof
KR20240056726A (ko)	2024-04-30	니로가세스타트의 합성
US6486195B1 (en)	2002-11-26	Thermodynamically stable crystal form of 4″-deoxy-4″-epi-methylamino avermectin B1a/B1b benzoic acid salt and processes for its preparation
EP0688775B1 (de)	2002-03-06	Verfahren zur Reinigung von 23-E Isomeren von 23-Imino LL-F28249 Derivate
US5677332A (en)	1997-10-14	Antiparasitic agents
SU648099A3 (ru)	1979-02-15	Способ получени галогенпроизводных антибиотика изо-лазалоцида а
US6835829B2 (en)	2004-12-28	Purification process
FR2474503A1 (fr)	1981-07-31	Composes intermediaires utiles pour l'obtention de la spectinomycine et de ses analogues ainsi que l'utilisation de ces produits
FR2523583A1 (fr)	1983-09-23	Procede de production de 6'-alkylspectinomycines et de leurs analogues et nouveaux composes intermediaires utilises dans ce procede
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