GB1058675A – New spiroalkane derivatives
– Google Patents
GB1058675A – New spiroalkane derivatives
– Google Patents
New spiroalkane derivatives
Info
Publication number
GB1058675A
GB1058675A
GB21780/64A
GB2178064A
GB1058675A
GB 1058675 A
GB1058675 A
GB 1058675A
GB 21780/64 A
GB21780/64 A
GB 21780/64A
GB 2178064 A
GB2178064 A
GB 2178064A
GB 1058675 A
GB1058675 A
GB 1058675A
Authority
GB
United Kingdom
Prior art keywords
formula
integer
aza
hal
spiroalkane
Prior art date
1963-05-27
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
Application number
GB21780/64A
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.)
DAUSSE LAB
Original Assignee
DAUSSE LAB
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.)
1963-05-27
Filing date
1964-05-26
Publication date
1967-02-15
1964-05-26
Application filed by DAUSSE LAB
filed
Critical
DAUSSE LAB
1967-02-15
Publication of GB1058675A
publication
Critical
patent/GB1058675A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
150000001875
compounds
Chemical class
0.000
abstract
6
239000002253
acid
Substances
0.000
abstract
3
125000001453
quaternary ammonium group
Chemical group
0.000
abstract
3
150000003839
salts
Chemical class
0.000
abstract
3
-1
C1- 6 alkylene radical
Chemical class
0.000
abstract
2
229930013930
alkaloid
Natural products
0.000
abstract
2
239000000203
mixture
Substances
0.000
abstract
2
230000000054
salidiuretic effect
Effects
0.000
abstract
2
DNXIKVLOVZVMQF-UHFFFAOYSA-N
(3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester
Natural products
C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1
DNXIKVLOVZVMQF-UHFFFAOYSA-N
0.000
abstract
1
SZLZWPPUNLXJEA-UHFFFAOYSA-N
11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester
Natural products
C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1
SZLZWPPUNLXJEA-UHFFFAOYSA-N
0.000
abstract
1
CJDRUOGAGYHKKD-RQBLFBSQSA-N
1pon08459r
Chemical compound
CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O
CJDRUOGAGYHKKD-RQBLFBSQSA-N
0.000
abstract
1
URZHJTCEXXIFLG-UHFFFAOYSA-N
6-chloro-3-(4-fluorophenyl)-3-methyl-1,1-dioxo-2,4-dihydro-1lambda6,2,4-benzothiadiazine-7-sulfonamide
Chemical compound
FC1=CC=C(C=C1)C1(NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O)C
URZHJTCEXXIFLG-UHFFFAOYSA-N
0.000
abstract
1
CJDRUOGAGYHKKD-UHFFFAOYSA-N
Iso-ajmalin
Natural products
CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2
CJDRUOGAGYHKKD-UHFFFAOYSA-N
0.000
abstract
1
LCGISIDBXHGCDW-VKHMYHEASA-N
L-glutamine amide
Chemical compound
NC(=O)[C@@H](N)CCC(N)=O
LCGISIDBXHGCDW-VKHMYHEASA-N
0.000
abstract
1
244000061121
Rauvolfia serpentina
Species
0.000
abstract
1
SZLZWPPUNLXJEA-FMCDHCOASA-N
Rescinnamine
Natural products
O=C(O[C@H]1[C@@H](OC)[C@@H](C(=O)OC)[C@@H]2[C@H](C1)CN1[C@@H](c3[nH]c4c(c3CC1)ccc(OC)c4)C2)/C=C/c1cc(OC)c(OC)c(OC)c1
SZLZWPPUNLXJEA-FMCDHCOASA-N
0.000
abstract
1
LCQMZZCPPSWADO-UHFFFAOYSA-N
Reserpilin
Natural products
COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12
LCQMZZCPPSWADO-UHFFFAOYSA-N
0.000
abstract
1
QEVHRUUCFGRFIF-SFWBKIHZSA-N
Reserpine
Natural products
O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3
QEVHRUUCFGRFIF-SFWBKIHZSA-N
0.000
abstract
1
VTVQHYQGTTVKDE-FXBSTXGRSA-N
Sarpagine
Natural products
CC=C1CN2[C@H]3Cc4c([nH]c5ccc(O)cc45)[C@@H]2C[C@@H]1[C@H]3CO
VTVQHYQGTTVKDE-FXBSTXGRSA-N
0.000
abstract
1
229960004332
ajmaline
Drugs
0.000
abstract
1
150000003797
alkaloid derivatives
Chemical class
0.000
abstract
1
125000000217
alkyl group
Chemical group
0.000
abstract
1
239000002775
capsule
Substances
0.000
abstract
1
125000002915
carbonyl group
Chemical group
[*:2]C([*:1])=O
0.000
abstract
1
239000008298
dragée
Substances
0.000
abstract
1
239000003937
drug carrier
Substances
0.000
abstract
1
239000012458
free base
Substances
0.000
abstract
1
125000005843
halogen group
Chemical group
0.000
abstract
1
230000001077
hypotensive effect
Effects
0.000
abstract
1
125000002496
methyl group
Chemical group
[H]C([H])([H])*
0.000
abstract
1
125000001570
methylene group
Chemical group
[H]C([H])([*:1])[*:2]
0.000
abstract
1
ADFKWOUMZCHRTD-QDHOPYFXSA-O
raupine
Chemical compound
C1=C(O)C=C2C(C[C@@H]3[N+]4=C/C([C@@H](C[C@H]44)[C@H]3CO)=C/C)=C4NC2=C1
ADFKWOUMZCHRTD-QDHOPYFXSA-O
0.000
abstract
1
SMSAPZICLFYVJS-QEGASFHISA-N
rescinnamine
Chemical compound
O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1
SMSAPZICLFYVJS-QEGASFHISA-N
0.000
abstract
1
229960001965
rescinnamine
Drugs
0.000
abstract
1
BJOIZNZVOZKDIG-MDEJGZGSSA-N
reserpine
Chemical compound
O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1
BJOIZNZVOZKDIG-MDEJGZGSSA-N
0.000
abstract
1
229960003147
reserpine
Drugs
0.000
abstract
1
MDMGHDFNKNZPAU-UHFFFAOYSA-N
roserpine
Natural products
C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1
MDMGHDFNKNZPAU-UHFFFAOYSA-N
0.000
abstract
1
239000003826
tablet
Substances
0.000
abstract
1
230000001225
therapeutic effect
Effects
0.000
abstract
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
C07D221/20—Spiro-condensed ring systems
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
A61K31/00—Medicinal preparations containing organic active ingredients
Abstract
Novel compounds of the Formula I wherein k represents an integer from 1 to 7, m represents 0 or an integer from 1 to 3 and n represents an integer from 1 to 4, the sum of k, m and n being at least 3 and at most 8, and A is a straight or branched C1- 6 alkylene radical, and acid addition salts and quaternary ammonium derivatives thereof, are prepared by reacting compounds of the Formula II with a compound of the formula Q-NH2, where Q represents a group of the formula R-S-C(: NH)-, R-O-C(: NH)- or NC- where R represents an alkyl group, or by reacting a compound of the Formula III with a compound of the formula Hal-A-NH-C(: NH)-NH2 or Hal-A1-CO-NH-C(: NH)-NH2, where Hal represents a halogen atom and A1 is such that -A1-CH2- is the same as A, and where appropriate converting a carbonyl group to a methylene group and if desired, converting a free base into an acid addition salt or quaternary ammonium derivative thereof.
GB21780/64A
1963-05-27
1964-05-26
New spiroalkane derivatives
Expired
GB1058675A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
FR936120A
FR1426082A
(en)
1963-05-27
1963-05-27
New n- (omega-guanidinoalcoyl) azaspiroalkanes
FR936591A
FR3013M
(en)
1963-05-27
1963-05-30
New n- (ω-guanidinoalcoyl) azaspiroalkanes and their salts.
Publications (1)
Publication Number
Publication Date
GB1058675A
true
GB1058675A
(en)
1967-02-15
Family
ID=26201526
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB21780/64A
Expired
GB1058675A
(en)
1963-05-27
1964-05-26
New spiroalkane derivatives
Country Status (12)
Country
Link
US
(1)
US3326925A
(en)
BE
(1)
BE648317A
(en)
BR
(1)
BR6459494D0
(en)
CH
(1)
CH441329A
(en)
DE
(1)
DE1470010B1
(en)
DK
(1)
DK122886B
(en)
FR
(2)
FR1426082A
(en)
GB
(1)
GB1058675A
(en)
LU
(1)
LU46155A1
(en)
NL
(2)
NL6405907A
(en)
OA
(1)
OA00117A
(en)
SE
(1)
SE301651B
(en)
Cited By (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US5939450A
(en)
*
1995-07-13
1999-08-17
Anormed Inc.
N,N-dimethyl-8,8-dipropyl-2-azaspiro 4.5!decane-2-propanamine dimaleate
Families Citing this family (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4963557A
(en)
*
1987-09-28
1990-10-16
Smithkline Beecham Corporation
Immunomodulatory azaspiranes
CA1336090C
(en)
*
1988-08-31
1995-06-27
Isao Hayakawa
Spiro-substituted cyclic amines of quinolone derivatives
US5591748A
(en)
*
1991-06-07
1997-01-07
Smithkline Beecham Corporation
Immunomodulatory azaspiranes
Family Cites Families (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3078272A
(en)
*
1963-02-19
N-aza-bicyclo-alkylene-imino
DE1100637B
(en)
*
1958-06-10
1961-03-02
Ciba Geigy
Process for the preparation of alkyleniminoalkylguanidines, their acyl compounds, salts and quaternary ammonium compounds
US3106552A
(en)
*
1960-07-19
1963-10-08
Geschickter Fund Med Res
Nu-substituted azaspiranes and azaspirane-diones and processes for their preparation
US3200118A
(en)
*
1961-10-31
1965-08-10
Geschickter Fund Med Res
Spirocyclic hydrazine imides
US3189601A
(en)
*
1964-01-10
1965-06-15
Ciba Geigy Corp
N, n-alkylene-imino-lower alkanoamidine compounds
0
BE
BE648317D
patent/BE648317A/xx
unknown
NL
NL124128D
patent/NL124128C/xx
active
1963
1963-05-27
FR
FR936120A
patent/FR1426082A/en
not_active
Expired
1963-05-30
FR
FR936591A
patent/FR3013M/en
not_active
Expired
1964
1964-05-25
LU
LU46155D
patent/LU46155A1/xx
unknown
1964-05-26
CH
CH683264A
patent/CH441329A/en
unknown
1964-05-26
GB
GB21780/64A
patent/GB1058675A/en
not_active
Expired
1964-05-26
DE
DE19641470010
patent/DE1470010B1/en
active
Pending
1964-05-26
US
US370343A
patent/US3326925A/en
not_active
Expired – Lifetime
1964-05-27
SE
SE6448/64A
patent/SE301651B/xx
unknown
1964-05-27
DK
DK264364AA
patent/DK122886B/en
unknown
1964-05-27
NL
NL6405907A
patent/NL6405907A/xx
unknown
1964-05-27
BR
BR159494/64A
patent/BR6459494D0/en
unknown
1964-05-28
OA
OA50127A
patent/OA00117A/en
unknown
Cited By (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US5939450A
(en)
*
1995-07-13
1999-08-17
Anormed Inc.
N,N-dimethyl-8,8-dipropyl-2-azaspiro 4.5!decane-2-propanamine dimaleate
Also Published As
Publication number
Publication date
BE648317A
(en)
FR3013M
(en)
1964-12-21
NL6405907A
(en)
1964-11-30
DE1470010B1
(en)
1969-12-18
US3326925A
(en)
1967-06-20
BR6459494D0
(en)
1973-08-02
SE301651B
(en)
1968-06-17
OA00117A
(en)
1966-01-15
FR1426082A
(en)
1966-01-28
DK122886B
(en)
1972-04-24
NL124128C
(en)
LU46155A1
(en)
1972-01-01
CH441329A
(en)
1967-08-15
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