BG60436B2 - 1-окса-2-оксо-8-азаспиро(4,5)декани,фармацевтични състави, които ги съдържат,и метод за получаването им - Google Patents

1-окса-2-оксо-8-азаспиро(4,5)декани,фармацевтични състави, които ги съдържат,и метод за получаването им Download PDF

Info

Publication number: BG60436B2
Authority: BG; Bulgaria
Prior art keywords: oxo; oxa; fluorophenyl; decane; butyl
Prior art date: 1989-08-10

Application number

BG098261A

Other languages

Bulgarian (bg)

English (en)

Inventor

Edit Toth

Jozsef Toerley

Laszlo Szporny

Bela Kiss

Egon Karpati

Eva Palosi

Dora Groo

Istvan Laszlovszky

Zsolt Szombathelyi

Adam Sarkadi

Aniko Gere

Katalin Csomor

Mihaly Bodo

Judit Laszy

Zsolt Szentirmay

Original Assignee

Richter Gedeon Vegyeszeti Gyar Rt.

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.)

1989-08-10

Filing date

1993-12-02

Publication date

1995-03-31

1993-12-02 Application filed by Richter Gedeon Vegyeszeti Gyar Rt. filed Critical Richter Gedeon Vegyeszeti Gyar Rt.

1995-03-31 Publication of BG60436B2 publication Critical patent/BG60436B2/bg

Links

238000000034 method Methods 0.000 title claims description 31
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 29
150000001875 compounds Chemical class 0.000 claims abstract description 70
150000003839 salts Chemical class 0.000 claims abstract description 32
239000002253 acid Substances 0.000 claims abstract description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
150000002431 hydrogen Chemical class 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
-1 1-Oxa-2-oxo-3-cyclohexyl-4-methylene- [4,4-bis (4-fluorophenyl) butyl] -3,8-diazaspiro (4,5) decane Chemical compound 0.000 claims description 38
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 14
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
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230000000141 anti-hypoxic effect Effects 0.000 claims description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
WYZZNMWIWHRXRM-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decane Chemical compound C1NCCC21CCNCC2 WYZZNMWIWHRXRM-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
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DXZFOANBRHMEGN-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-4-methylidene-3-phenyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C(N(C(=O)O2)C=2C=CC=CC=2)=C)CC1 DXZFOANBRHMEGN-UHFFFAOYSA-N 0.000 claims description 4
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208000029028 brain injury Diseases 0.000 claims description 4
VRQDXCMKHWFAFO-UHFFFAOYSA-N 3-ethyl-8-[2-(4-fluorophenyl)ethyl]-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(CC)C(=O)OC11CCN(CCC=2C=CC(F)=CC=2)CC1 VRQDXCMKHWFAFO-UHFFFAOYSA-N 0.000 claims description 3
GOCCZEHUQUMBMB-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-3-butyl-4-methylidene-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(CCCC)C(=O)OC11CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 GOCCZEHUQUMBMB-UHFFFAOYSA-N 0.000 claims description 3
OFRYIDMZALXALS-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-3-tert-butyl-4-methylidene-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=C1N(C(C)(C)C)C(=O)OC11CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 OFRYIDMZALXALS-UHFFFAOYSA-N 0.000 claims description 3
RINGGRQYDNFYMI-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-4-methylidene-1,3-dioxa-8-azaspiro[4.5]decan-2-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C(OC(=O)O2)=C)CC1 RINGGRQYDNFYMI-UHFFFAOYSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
UGXBRFVWHZKUSR-UHFFFAOYSA-N 8-[2-(4-fluorophenyl)ethyl]-4-hydroxy-3,4-dimethyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(C)C(=O)OC11CCN(CCC=2C=CC(F)=CC=2)CC1 UGXBRFVWHZKUSR-UHFFFAOYSA-N 0.000 claims description 2
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230000006931 brain damage Effects 0.000 claims 2
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YMANQWHUUFJQOW-UHFFFAOYSA-N 1,2-diazaspiro[4.5]decane Chemical compound N1NCCC11CCCCC1 YMANQWHUUFJQOW-UHFFFAOYSA-N 0.000 claims 1
KWYZAOLBJXZIQM-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-3-butyl-4-hydroxy-4-methyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1(O)N(CCCC)C(=O)OC11CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 KWYZAOLBJXZIQM-UHFFFAOYSA-N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
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125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
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238000004458 analytical method Methods 0.000 description 19
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235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
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229910000029 sodium carbonate Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical group C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
239000012089 stop solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
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YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
210000004885 white matter Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Cardiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Psychiatry (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)

BG098261A 1989-08-10 1993-12-02 1-окса-2-оксо-8-азаспиро(4,5)декани,фармацевтични състави, които ги съдържат,и метод за получаването им BG60436B2 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU894095A HU204530B (en)	1989-08-10	1989-08-10	Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them
SG96294A SG96294G (en)	1989-08-10	1994-07-16	1-oxa-2-oxo-8-azaspiro[4,5] decane derivatives, processes for their preparation and pharmaceutical compositions thereof

Publications (1)

Publication Number	Publication Date
BG60436B2 true BG60436B2 (bg)	1995-03-31

Family

ID=26317733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG098261A BG60436B2 (bg)	1989-08-10	1993-12-02	1-окса-2-оксо-8-азаспиро(4,5)декани,фармацевтични състави, които ги съдържат,и метод за получаването им

Country Status (23)

Country	Link
US (1)	US5118687A (hu)
EP (1)	EP0414421B1 (hu)
JP (1)	JPH0749431B2 (hu)
KR (1)	KR940006635B1 (hu)
AT (1)	ATE103920T1 (hu)
AU (1)	AU622039B2 (hu)
BG (1)	BG60436B2 (hu)
DD (1)	DD299429A5 (hu)
DE (1)	DE69007904T2 (hu)
DK (1)	DK0414421T3 (hu)
ES (1)	ES2052180T3 (hu)
FI (1)	FI93455C (hu)
HK (1)	HK145994A (hu)
HR (1)	HRP920778A2 (hu)
HU (2)	HU204530B (hu)
IE (1)	IE64911B1 (hu)
IL (1)	IL95320A (hu)
NO (1)	NO177962C (hu)
NZ (1)	NZ234848A (hu)
PL (3)	PL163593B1 (hu)
SG (1)	SG96294G (hu)
SI (1)	SI9011538A (hu)
ZA (1)	ZA906302B (hu)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU150489A (sh) *	1989-08-10	1992-12-21	W.L. Gore & Co. Gmbh.	Uređaj za ispitivanje odevnih predmeta na nepromočivost
WO2001028602A1 (en) *	1999-10-15	2001-04-26	Genetics Institute, Inc.	Formulations of hyaluronic acid for delivery of osteogenic proteins
KR20020091462A (ko) *	2001-05-30	2002-12-06	삼성광주전자 주식회사	원료 굳음 방지기능을 갖는 자동판매기 및 그 제어방법
GB201416346D0 (en) *	2014-09-16	2014-10-29	Shire Internat Gmbh	Spirocyclic derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR96352E (fr) *	1967-12-29	1972-06-16	Science Union & Cie	Nouveaux dérives du spiro (4,5) decane et leur procédé de préparation.
BE790675A (fr) *	1971-10-29	1973-04-27	Science Union & Cie	Nouveaux derives de l'oxa-1 diaza-3,8 spiro (4,5) decane
EP0189370A3 (de) *	1985-01-16	1988-01-27	Sandoz Ag	Spiro-dioxolane, -dithiolane und -oxothiolane
KR940003491B1 (ko) *	1989-08-10	1994-04-23	리히터 게데온 베기에스제티 기아르 알.티	4,4-이중 치환된 피페리딘 유도체와 그 제조방법 및 상기 화합물을 함유하는 약제학적 조성물
HU204529B (en) *	1989-08-10	1992-01-28	Richter Gedeon Vegyeszet	Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them

1989
- 1989-08-10 HU HU894095A patent/HU204530B/hu not_active IP Right Cessation
1990
- 1990-08-09 JP JP2209358A patent/JPH0749431B2/ja not_active Expired - Lifetime
- 1990-08-09 AT AT90308784T patent/ATE103920T1/de not_active IP Right Cessation
- 1990-08-09 DK DK90308784.9T patent/DK0414421T3/da active
- 1990-08-09 SI SI9011538A patent/SI9011538A/sl unknown
- 1990-08-09 KR KR1019900012256A patent/KR940006635B1/ko not_active IP Right Cessation
- 1990-08-09 DD DD90343361A patent/DD299429A5/de not_active IP Right Cessation
- 1990-08-09 EP EP90308784A patent/EP0414421B1/en not_active Expired - Lifetime
- 1990-08-09 ZA ZA906302A patent/ZA906302B/xx unknown
- 1990-08-09 NZ NZ234848A patent/NZ234848A/en unknown
- 1990-08-09 IL IL9532090A patent/IL95320A/en not_active IP Right Cessation
- 1990-08-09 DE DE69007904T patent/DE69007904T2/de not_active Expired - Fee Related
- 1990-08-09 IE IE288490A patent/IE64911B1/en not_active IP Right Cessation
- 1990-08-09 NO NO903512A patent/NO177962C/no unknown
- 1990-08-09 ES ES90308784T patent/ES2052180T3/es not_active Expired - Lifetime
- 1990-08-09 AU AU60807/90A patent/AU622039B2/en not_active Ceased
- 1990-08-10 PL PL90291702A patent/PL163593B1/pl unknown
- 1990-08-10 PL PL90286440A patent/PL163370B1/pl unknown
- 1990-08-10 PL PL90291701A patent/PL163431B1/pl unknown
- 1990-08-10 FI FI903972A patent/FI93455C/fi not_active IP Right Cessation
- 1990-08-10 US US07/566,275 patent/US5118687A/en not_active Expired - Fee Related
1992
- 1992-10-01 HR HRP-1538/90A patent/HRP920778A2/hr not_active Application Discontinuation
1993
- 1993-12-02 BG BG098261A patent/BG60436B2/bg unknown
1994
- 1994-07-16 SG SG96294A patent/SG96294G/en unknown
- 1994-10-12 HU HU94P/P00036P patent/HU210072A9/hu unknown
- 1994-12-22 HK HK145994A patent/HK145994A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU210072A9 (en)	1995-02-28
JPH0377884A (ja)	1991-04-03
IE64911B1 (en)	1995-09-20
NO177962B (no)	1995-09-18
HK145994A (en)	1994-12-30
NO903512D0 (no)	1990-08-09
IE902884A1 (en)	1991-02-27
HUT55786A (en)	1991-06-28
SI9011538A (sl)	1998-08-31
PL291702A1 (en)	1992-05-04
ATE103920T1 (de)	1994-04-15
IL95320A0 (en)	1991-06-30
NO903512L (no)	1991-02-11
DK0414421T3 (da)	1994-05-16
ES2052180T3 (es)	1994-07-01
AU622039B2 (en)	1992-03-26
HU204530B (en)	1992-01-28
NO177962C (no)	1995-12-27
DD299429A5 (de)	1992-04-16
PL163593B1 (en)	1994-04-29
FI903972A0 (fi)	1990-08-10
JPH0749431B2 (ja)	1995-05-31
DE69007904T2 (de)	1994-07-21
ZA906302B (en)	1991-06-26
PL163370B1 (pl)	1994-03-31
PL163431B1 (pl)	1994-03-31
KR940006635B1 (ko)	1994-07-23
DE69007904D1 (de)	1994-05-11
EP0414421A3 (en)	1991-07-24
AU6080790A (en)	1991-02-14
US5118687A (en)	1992-06-02
IL95320A (en)	1994-01-25
NZ234848A (en)	1992-03-26
EP0414421A2 (en)	1991-02-27
PL291701A1 (en)	1992-05-04
EP0414421B1 (en)	1994-04-06
FI93455C (fi)	1995-04-10
SG96294G (en)	1994-10-28
PL286440A1 (en)	1992-01-27
HRP920778A2 (en)	1998-02-28
FI93455B (fi)	1994-12-30
KR910004632A (ko)	1991-03-29

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