FI105270B - Menetelmä terapeuttisesti käyttökelpoisten oktahydro-1H-1-pyrindiini-4,5,6,7-terolien valmistamiseksi - Google Patents

Menetelmä terapeuttisesti käyttökelpoisten oktahydro-1H-1-pyrindiini-4,5,6,7-terolien valmistamiseksi Download PDF

Info

Publication number: FI105270B
Authority: FI; Finland
Prior art keywords: formula; compound; octahydro; hydrogen; phenylmethoxy
Prior art date: 1991-09-18

Application number

FI941259A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI941259A0 (fi

FI941259L (fi

Inventor

Norton P Peet

Robert A Farr

Mohinder S Kang

Sai P Sunkara

Original Assignee

Merrell Pharma Inc

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.)

1991-09-18

Filing date

1994-03-17

Publication date

2000-07-14

1994-03-17 Application filed by Merrell Pharma Inc filed Critical Merrell Pharma Inc

1994-03-17 Publication of FI941259A0 publication Critical patent/FI941259A0/fi

1994-03-17 Publication of FI941259L publication Critical patent/FI941259L/fi

2000-07-14 Application granted granted Critical

2000-07-14 Publication of FI105270B publication Critical patent/FI105270B/fi

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 14
230000008569 process Effects 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 83
-1 lithium aluminum hydride Chemical compound 0.000 claims description 67
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
230000003197 catalytic effect Effects 0.000 claims description 10
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001350 alkyl halides Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 4
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235000008390 olive oil Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920005606 polypropylene copolymer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000004224 protection Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000001950 radioprotection Effects 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
CXEMWUYNUIKMNF-UHFFFAOYSA-N tert-butyl 4-chlorosulfonylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(S(Cl)(=O)=O)CC1 CXEMWUYNUIKMNF-UHFFFAOYSA-N 0.000 description 1
OVAFZCTWIMXZLF-UHFFFAOYSA-N tert-butyl n-[(4-methoxyphenyl)methyl]carbamate Chemical compound COC1=CC=C(CNC(=O)OC(C)(C)C)C=C1 OVAFZCTWIMXZLF-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Hematology (AREA)
Diabetes (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Enzymes And Modification Thereof (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Indole Compounds (AREA)

FI941259A 1991-09-18 1994-03-17 Menetelmä terapeuttisesti käyttökelpoisten oktahydro-1H-1-pyrindiini-4,5,6,7-terolien valmistamiseksi FI105270B (fi)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US76157991A	1991-09-18	1991-09-18
US76157991		1991-09-18
US89317192		1992-06-03
US07/893,171 US5262425A (en)	1991-09-18	1992-06-03	α-mannosidase inhibitors
PCT/US1992/006707 WO1993005781A1 (en)	1991-09-18	1992-08-10	Novel alpha-mannosidase inhibitors
US9206707		1992-08-10

Publications (3)

Publication Number	Publication Date
FI941259A0 FI941259A0 (fi)	1994-03-17
FI941259L FI941259L (fi)	1994-03-17
FI105270B true FI105270B (fi)	2000-07-14

Family

ID=27117010

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI941259A FI105270B (fi)	1991-09-18	1994-03-17	Menetelmä terapeuttisesti käyttökelpoisten oktahydro-1H-1-pyrindiini-4,5,6,7-terolien valmistamiseksi

Country Status (15)

Country	Link
US (1)	US5262425A (da)
EP (1)	EP0641327B1 (da)
JP (1)	JP3226173B2 (da)
KR (1)	KR100244012B1 (da)
AT (1)	ATE175960T1 (da)
AU (1)	AU659486B2 (da)
CA (1)	CA2116224C (da)
DE (1)	DE69228259T2 (da)
DK (1)	DK0641327T3 (da)
ES (1)	ES2127758T3 (da)
FI (1)	FI105270B (da)
GR (1)	GR3029745T3 (da)
HU (1)	HU216789B (da)
NO (1)	NO300372B1 (da)
WO (1)	WO1993005781A1 (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5773239A (en) *	1993-10-19	1998-06-30	Mount Sinai Hospital Corporation.	Mannosidase inhibitors, process for their preparation and their use as therapeutic agents
US5650413A (en) *	1995-06-07	1997-07-22	Glycodesign Inc.	Derivatives of swainsonine, processes for their preparation and their use as therapeutic agents
US6048870A (en) *	1996-10-01	2000-04-11	Glycodesign	3, 5, and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents
CA2286766A1 (en)	1997-04-15	1998-10-22	Glycodesign Inc.	Alkaloid halide salts of swainsonine and methods of use
US6245316B1 (en)	1997-10-08	2001-06-12	David Platt	Enhancement of delivery of radioimaging and radioprotective agents
WO1999021858A1 (en) *	1997-10-24	1999-05-06	Glycodesign Inc.	Synthesis of swainsonine salts

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4031102A (en) *	1972-10-21	1977-06-21	John Wyeth & Brother Limited	Cyclopenteno[b]pyridine derivatives
GB2088860B (en) *	1980-12-09	1984-05-23	Wyeth John & Brother Ltd	Process for preparing ring-fused pyridine derivatives

1992
- 1992-06-03 US US07/893,171 patent/US5262425A/en not_active Expired - Fee Related
- 1992-08-10 AT AT92918131T patent/ATE175960T1/de not_active IP Right Cessation
- 1992-08-10 AU AU24771/92A patent/AU659486B2/en not_active Ceased
- 1992-08-10 DE DE69228259T patent/DE69228259T2/de not_active Expired - Fee Related
- 1992-08-10 HU HU9400787A patent/HU216789B/hu not_active IP Right Cessation
- 1992-08-10 JP JP50602793A patent/JP3226173B2/ja not_active Expired - Fee Related
- 1992-08-10 WO PCT/US1992/006707 patent/WO1993005781A1/en not_active Ceased
- 1992-08-10 KR KR1019940700863A patent/KR100244012B1/ko not_active Expired - Fee Related
- 1992-08-10 DK DK92918131T patent/DK0641327T3/da active
- 1992-08-10 EP EP92918131A patent/EP0641327B1/en not_active Expired - Lifetime
- 1992-08-10 ES ES92918131T patent/ES2127758T3/es not_active Expired - Lifetime
- 1992-08-10 CA CA002116224A patent/CA2116224C/en not_active Expired - Fee Related
1994
- 1994-03-17 NO NO940972A patent/NO300372B1/no unknown
- 1994-03-17 FI FI941259A patent/FI105270B/fi active
1999
- 1999-03-19 GR GR990400830T patent/GR3029745T3/el unknown

Also Published As

Publication number	Publication date
FI941259A0 (fi)	1994-03-17
AU659486B2 (en)	1995-05-18
CA2116224C (en)	2003-06-03
NO940972L (no)	1994-03-17
HUT70527A (en)	1995-10-30
DE69228259D1 (de)	1999-03-04
DK0641327T3 (da)	1999-09-13
EP0641327A4 (en)	1994-06-01
GR3029745T3 (en)	1999-06-30
ES2127758T3 (es)	1999-05-01
DE69228259T2 (de)	1999-06-02
NO300372B1 (no)	1997-05-20
JP3226173B2 (ja)	2001-11-05
FI941259L (fi)	1994-03-17
HU9400787D0 (en)	1994-06-28
JPH06510785A (ja)	1994-12-01
NO940972D0 (no)	1994-03-17
ATE175960T1 (de)	1999-02-15
CA2116224A1 (en)	1993-04-01
EP0641327A1 (en)	1995-03-08
WO1993005781A1 (en)	1993-04-01
HU216789B (hu)	1999-08-30
KR100244012B1 (ko)	2000-03-02
US5262425A (en)	1993-11-16
AU2477192A (en)	1993-04-27
EP0641327B1 (en)	1999-01-20

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