FI105478B - Menetelmä valmistaa terapeuttisesti vaikuttavaa 2-deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja - Google Patents

Menetelmä valmistaa terapeuttisesti vaikuttavaa 2-deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja Download PDF

Info

Publication number: FI105478B
Authority: FI; Finland
Prior art keywords: compound; tetradeoxy; acetamido; glycero; formula
Prior art date: 1990-04-24

Application number

FI924790A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI924790A0 (fi

FI924790L (fi

Inventor

Betty Jin

Wen Yang Wu

Basil Danylec

Itzstein Laurence Mark Von

Phan Tho Van

Original Assignee

Biota Scient Management

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.)

1990-04-24

Filing date

1992-10-22

Publication date

2000-08-31

1992-10-22 Application filed by Biota Scient Management filed Critical Biota Scient Management

1992-10-22 Publication of FI924790A0 publication Critical patent/FI924790A0/fi

1992-10-22 Publication of FI924790L publication Critical patent/FI924790L/fi

2000-08-31 Application granted granted Critical

2000-08-31 Publication of FI105478B publication Critical patent/FI105478B/fi

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 17
150000001875 compounds Chemical class 0.000 claims description 117
239000011734 sodium Substances 0.000 claims description 28
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229910052708 sodium Inorganic materials 0.000 claims description 26
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
-1 aralkyl amidine Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
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125000003710 aryl alkyl group Chemical group 0.000 description 4
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230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011160 research Methods 0.000 description 1
229960000888 rimantadine Drugs 0.000 description 1
SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
BSEGPXORVPHION-VPHPIMPESA-M sodium (2R,3S)-3-hydroxy-2-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]-3,6-dihydro-2H-pyran-6-carboxylate Chemical compound C1(C=C[C@H](O)[C@@H](O1)[C@@H](O)[C@H](O)[C@H](O)CO)C(=O)[O-].[Na+] BSEGPXORVPHION-VPHPIMPESA-M 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
CIJQGPVMMRXSQW-UHFFFAOYSA-M sodium;2-aminoacetic acid;hydroxide Chemical compound O.[Na+].NCC([O-])=O CIJQGPVMMRXSQW-UHFFFAOYSA-M 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000007704 transition Effects 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Hydrogenated Pyridines (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI924790A 1990-04-24 1992-10-22 Menetelmä valmistaa terapeuttisesti vaikuttavaa 2-deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja FI105478B (fi)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
AUPJ980090		1990-04-24
AUPJ980090		1990-04-24
AUPK289690		1990-10-19
AUPK289690		1990-10-19
AUPK453791		1991-02-11
AUPK453791		1991-02-11
AU9100161		1991-04-24
PCT/AU1991/000161 WO1991016320A1 (en)	1990-04-24	1991-04-24	Derivatives and analogues of 2-deoxy-2,3-didehydro-n-acetyl neuraminic acid and their use as antiviral agents

Publications (3)

Publication Number	Publication Date
FI924790A0 FI924790A0 (fi)	1992-10-22
FI924790L FI924790L (fi)	1992-10-22
FI105478B true FI105478B (fi)	2000-08-31

Family

ID=27157556

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
FI924790A FI105478B (fi)	1990-04-24	1992-10-22	Menetelmä valmistaa terapeuttisesti vaikuttavaa 2-deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja
FI20001231A FI20001231L (fi)	1990-04-24	2000-05-23	2-Deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja ja niiden käyttö antiviraalisina aineina

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
FI20001231A FI20001231L (fi)	1990-04-24	2000-05-23	2-Deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja ja niiden käyttö antiviraalisina aineina

Country Status (37)

Country	Link
US (2)	US5360817A (da)
EP (2)	EP0786458B1 (da)
JP (1)	JP2944750B2 (da)
KR (1)	KR0169496B1 (da)
CN (3)	CN1143853C (da)
AP (1)	AP249A (da)
AT (2)	ATE161253T1 (da)
AU (2)	AU654815B2 (da)
BG (1)	BG62092B1 (da)
CA (2)	CA2081356C (da)
CY (1)	CY2186B1 (da)
CZ (1)	CZ288492B6 (da)
DE (3)	DE69133604D1 (da)
DK (1)	DK0526543T3 (da)
ES (2)	ES2113881T3 (da)
FI (2)	FI105478B (da)
GR (1)	GR3026225T3 (da)
HK (2)	HK1003834A1 (da)
HU (2)	HU219355B (da)
IE (2)	IE911372A1 (da)
IL (1)	IL97936A (da)
LU (1)	LU90468I2 (da)
MY (1)	MY107843A (da)
NL (1)	NL990030I2 (da)
NO (3)	NO302751B1 (da)
NZ (1)	NZ237936A (da)
OA (1)	OA09679A (da)
PL (3)	PL167630B1 (da)
PT (1)	PT97460B (da)
RU (1)	RU2119487C1 (da)
SG (1)	SG43170A1 (da)
SI (1)	SI9110745B (da)
SK (1)	SK282950B6 (da)
UA (1)	UA41252C2 (da)
WO (1)	WO1991016320A1 (da)
YU (1)	YU48741B (da)
ZA (1)	ZA913086B (da)

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1991
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Also Published As

Publication number	Publication date
ZA913086B (en)	1992-12-30
DE19975068I1 (de)	2000-01-13
CA2291994A1 (en)	1991-10-25
PL167192B1 (pl)	1995-08-31
NO974670D0 (no)	1997-10-09
MY107843A (en)	1996-06-29
CN1143853C (zh)	2004-03-31
HK1003834A1 (en)	1998-11-06
PT97460A (pt)	1992-01-31
CN1091594C (zh)	2002-10-02
IL97936A (en)	1995-12-08
AU654815B2 (en)	1994-11-24
NO923944L (no)	1992-12-18
GR3026225T3 (en)	1998-05-29
FI924790A0 (fi)	1992-10-22
PT97460B (pt)	1999-01-29
NO923944D0 (no)	1992-10-09
EP0526543A1 (en)	1993-02-10
US5360817A (en)	1994-11-01
BG96978A (bg)	1993-12-24
NO1999021I1 (no)	1999-09-17
ATE406358T1 (de)	2008-09-15
ES2313730T3 (es)	2009-03-01
HUT61989A (en)	1993-03-29
JPH05507068A (ja)	1993-10-14
NL990030I2 (nl)	2000-02-01
YU48741B (sh)	1999-09-27
CA2291994C (en)	2003-10-14
NZ237936A (en)	1997-08-22
WO1991016320A1 (en)	1991-10-31
OA09679A (en)	1993-05-15
DK0526543T3 (da)	1998-08-24
DE69133604D1 (de)	2008-10-09
BG62092B1 (bg)	1999-02-26
EP0526543B1 (en)	1997-12-17
HU210717A9 (en)	1995-06-28
ES2113881T3 (es)	1998-05-16
KR0169496B1 (ko)	1999-01-15
EP0786458A2 (en)	1997-07-30
SK282950B6 (sk)	2003-01-09
HK1010191A1 (en)	1999-06-17
RU2119487C1 (ru)	1998-09-27
NO302751B1 (no)	1998-04-20
SI9110745B (en)	2001-06-30
AU7759091A (en)	1991-11-11
ATE161253T1 (de)	1998-01-15
NL990030I1 (nl)	1999-12-01
LU90468I2 (fr)	2000-01-03
AU7533891A (en)	1991-12-12
PL166918B1 (pl)	1995-07-31
US5648379A (en)	1997-07-15
AP249A (en)	1993-03-17
CS114591A3 (en)	1991-12-17
AP9100253A0 (en)	1991-04-30
EP0526543A4 (en)	1993-04-21
DE69128469T2 (de)	1998-06-04
EP0786458A3 (en)	1999-10-13
YU74591A (sh)	1994-06-24
SG43170A1 (en)	1997-10-17
UA41252C2 (uk)	2001-09-17
SI9110745A (en)	1997-04-30
CA2081356C (en)	2000-02-22
IE911372A1 (en)	1991-11-06
CY2186B1 (en)	2002-11-08
JP2944750B2 (ja)	1999-09-06
CN1150020A (zh)	1997-05-21
CN1184108A (zh)	1998-06-10
DE19975068I2 (de)	2002-10-10
IE980526A1 (en)	2003-10-15
FI20001231L (fi)	2000-05-23
CN1036849C (zh)	1997-12-31
NO974670L (no)	1992-12-18
EP0786458B1 (en)	2008-08-27
FI924790L (fi)	1992-10-22
CN1057260A (zh)	1991-12-25
DE69128469D1 (de)	1998-01-29
CA2081356A1 (en)	1991-10-25
PL167630B1 (pl)	1995-10-31
CZ288492B6 (en)	2001-06-13
HU9203180D0 (en)	1992-12-28
HU219355B (en)	2001-03-28

Publication	Publication Date	Title
FI105478B (fi)	2000-08-31	Menetelmä valmistaa terapeuttisesti vaikuttavaa 2-deoksi-2,3-didehydro-N-asetyylineuramiinihapon johdannaisia ja niiden analogeja
US5919819A (en)	1999-07-06	Dihydropyran derivatives as viral neuraminidase inhibitors
WO1995020583A1 (en)	1995-08-03	Derivatives of 2-deoxy-2,3-dehydro-n-acetylneuraminic acid (dana)
JPH0625209A (ja)	1994-02-01	α−Ｄ−ノイラミン酸の抗ウイルス性４−置換−２−デオキシ−２，３−ジデヒドロ誘導体
US5990156A (en)	1999-11-23	6-Carboxamido dihydropyran derivatives
WO1995018800A1 (en)	1995-07-13	Derivatives of 2-deoxy-2,3-dehydro-n-acetylneuraminic acid (dana)
US5639786A (en)	1997-06-17	Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of α-D-neuraninic acid
WO1996004265A1 (en)	1996-02-15	2,6-DIDEOXY-2,3-DIDEHYDRO-6-THIO DERIVATIVES OF α-D-NEURAMINIC ACID
US7157494B2 (en)	2007-01-02	Dimeric compounds and their use as anti-viral agents
US7230028B2 (en)	2007-06-12	Dimeric compounds and their use as anti-viral agents
JP3923081B6 (ja)	2007-08-22	ウイルスノイラミニダーゼ阻害剤としてのジヒドロピラン誘導体

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