CA2100820C - Amino-cyclodextrine et structures apparentees - Google Patents

Amino-cyclodextrine et structures apparentees

Info

Publication number: CA2100820C
Authority: CA; Canada
Prior art keywords: cyclodextrin; alpha; carbon atoms; allyl; nmr
Prior art date: 1993-07-19
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA002100820A

Other languages

English (en)

Other versions

CA2100820A1 (fr

Inventor

Stephen Hanessian

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

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.)

1993-07-19

Filing date

1993-07-19

Publication date

1999-11-02

1993-07-19 Application filed by Individual filed Critical Individual

1993-07-19 Priority to CA002100820A priority Critical patent/CA2100820C/fr

1994-07-19 Priority to PCT/US1994/008103 priority patent/WO1995003336A1/fr

1994-07-19 Priority to US08/583,097 priority patent/US5959089A/en

1994-07-19 Priority to AU74730/94A priority patent/AU7473094A/en

1995-01-20 Publication of CA2100820A1 publication Critical patent/CA2100820A1/fr

1999-11-02 Application granted granted Critical

1999-11-02 Publication of CA2100820C publication Critical patent/CA2100820C/fr

2013-07-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 43
150000001875 compounds Chemical class 0.000 claims abstract description 15
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 14
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 21
229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 19
229940043377 alpha-cyclodextrin Drugs 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 9
125000005335 azido alkyl group Chemical group 0.000 claims description 9
239000001116 FEMA 4028 Substances 0.000 claims description 8
229960004853 betadex Drugs 0.000 claims description 8
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical group [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical group [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 4
229910000103 lithium hydride Inorganic materials 0.000 claims description 4
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
GTBCENNLSAZFSM-UHFFFAOYSA-N 1-azido-3-iodopropane Chemical group ICCCN=[N+]=[N-] GTBCENNLSAZFSM-UHFFFAOYSA-N 0.000 claims description 2
QVZUACRCBPIEKQ-UHFFFAOYSA-N 1-azido-4-iodobutane Chemical group ICCCCN=[N+]=[N-] QVZUACRCBPIEKQ-UHFFFAOYSA-N 0.000 claims description 2
DBDTTWIVANTBPM-UHFFFAOYSA-N 1-azido-5-iodopentane Chemical group ICCCCCN=[N+]=[N-] DBDTTWIVANTBPM-UHFFFAOYSA-N 0.000 claims description 2
-1 alkali metal azide Chemical class 0.000 claims 2
150000001340 alkali metals Chemical class 0.000 claims 1
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 1
235000011175 beta-cyclodextrine Nutrition 0.000 claims 1
ZIYQWRXCJNFCPE-UHFFFAOYSA-N triphenylphosphane;azide Chemical compound [N-]=[N+]=[N-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZIYQWRXCJNFCPE-UHFFFAOYSA-N 0.000 claims 1
229940097362 cyclodextrins Drugs 0.000 abstract description 17
238000004519 manufacturing process Methods 0.000 abstract description 2
150000003003 phosphines Chemical class 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000005481 NMR spectroscopy Methods 0.000 description 29
239000000243 solution Substances 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 12
239000000047 product Substances 0.000 description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 7
101150041968 CDC13 gene Proteins 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000010828 elution Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
238000002390 rotary evaporation Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000004007 reversed phase HPLC Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
YMORVLBMLSBFQJ-UHFFFAOYSA-N 1-azido-3-chloropropane Chemical compound ClCCCN=[N+]=[N-] YMORVLBMLSBFQJ-UHFFFAOYSA-N 0.000 description 1
WIKLZASKGKBLQT-UHFFFAOYSA-N 1-azido-4-chlorobutane Chemical compound ClCCCCN=[N+]=[N-] WIKLZASKGKBLQT-UHFFFAOYSA-N 0.000 description 1
XWVZQJBZFOVNCW-UHFFFAOYSA-N 1-azido-5-chloropentane Chemical compound ClCCCCCN=[N+]=[N-] XWVZQJBZFOVNCW-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
102100022749 Aminopeptidase N Human genes 0.000 description 1
125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
101000757160 Homo sapiens Aminopeptidase N Proteins 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000004821 distillation Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000010354 integration Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

CA002100820A 1993-07-19 1993-07-19 Amino-cyclodextrine et structures apparentees Expired - Lifetime CA2100820C (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CA002100820A CA2100820C (fr)	1993-07-19	1993-07-19	Amino-cyclodextrine et structures apparentees
PCT/US1994/008103 WO1995003336A1 (fr)	1993-07-19	1994-07-19	Syntheses d'amino-cyclodextrines
US08/583,097 US5959089A (en)	1993-07-19	1994-07-19	Amino-cyclodextrin syntheses
AU74730/94A AU7473094A (en)	1993-07-19	1994-07-19	Amino-cyclodextrin syntheses

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002100820A CA2100820C (fr)	1993-07-19	1993-07-19	Amino-cyclodextrine et structures apparentees

Publications (2)

Publication Number	Publication Date
CA2100820A1 CA2100820A1 (fr)	1995-01-20
CA2100820C true CA2100820C (fr)	1999-11-02

Family

ID=4151944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002100820A Expired - Lifetime CA2100820C (fr)	1993-07-19	1993-07-19	Amino-cyclodextrine et structures apparentees

Country Status (3)

Country	Link
AU (1)	AU7473094A (fr)
CA (1)	CA2100820C (fr)
WO (1)	WO1995003336A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2860082B2 (ja) *	1995-07-08	1999-02-24	株式会社分子バイオホトニクス研究所	イソチオシアナート化新規シクロデキストリン誘導体

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3810737A1 (de) *	1988-03-30	1989-10-12	Macherey Nagel Gmbh & Co Kg	Substituierte cyclodextrine

1993
- 1993-07-19 CA CA002100820A patent/CA2100820C/fr not_active Expired - Lifetime
1994
- 1994-07-19 AU AU74730/94A patent/AU7473094A/en not_active Abandoned
- 1994-07-19 WO PCT/US1994/008103 patent/WO1995003336A1/fr not_active Ceased

Also Published As

Publication number	Publication date
AU7473094A (en)	1995-02-20
CA2100820A1 (fr)	1995-01-20
WO1995003336A1 (fr)	1995-02-02

Legal Events

Date	Code	Title	Description
1996-04-22	EEER	Examination request
2023-05-26	MKEX	Expiry	Effective date: 20130719

Publication	Publication Date	Title
Choi et al.	1991	In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of thialanyl and dioxolanyl nucleoside analogs
US5959089A (en)	1999-09-28	Amino-cyclodextrin syntheses
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KR950004899B1 (ko)	1995-05-15	모라노린 유도체의 제조법
CA1107720A (fr)	1981-08-25	Procede pour la preparation d'ethers de bufadienolide et de bufatrienolide
Thiem et al.	1985	Synthesis and Perkow reaction of uridine derivatives
Aslam et al.	2024	Chromatography Free Synthesis of Reversed N-Triazole Nucleosides Starting from α-D-Galactopyranose using 1, 3-Dipolar Cycloaddition Reactions.
Shing et al.	1984	Synthesis of benzyl 2-azido-2-deoxy-4-O-β-D-glucopyranosyl-α-D-glucopyranoside and 1, 6-anhydro-2-azido-2-deoxy-4-O-β-D-glucopyranosyl-β-D-glucopyranose
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JPS6121561B2 (fr)	1986-05-28
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