NZ190628A - Therapeutic compositions containing cyclopentyl aldehyde derivatives - Google Patents
Therapeutic compositions containing cyclopentyl aldehyde derivativesInfo
- Publication number
- NZ190628A NZ190628A NZ190628A NZ19062879A NZ190628A NZ 190628 A NZ190628 A NZ 190628A NZ 190628 A NZ190628 A NZ 190628A NZ 19062879 A NZ19062879 A NZ 19062879A NZ 190628 A NZ190628 A NZ 190628A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cyclopentyl
- cis
- aldehyde
- trans
- methyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/12—Alcohols containing rings other than six-membered aromatic rings containing five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial 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
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/27—Polyhydroxylic alcohols containing saturated rings
- C07C31/272—Monocyclic
- C07C31/274—Monocyclic with a three to five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/30—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings with a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/45—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/06—Saturated compounds having a carboxyl group bound to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/35—Unsaturated compounds having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Cyclopentyl-aldehyde derivatives of the general formula <IMAGE> wherein X and Y, which can be the same or different represent CHO, CH2OH or COOH; Z represents a C1-C3 alkyl group; A represents -CH2-, <IMAGE> or <IMAGE> including their geometrical isomers are of value in therapy and may be formulated as therapeutical compositions.
Description
New Zealand Paient Spedficaiion for Paient Number 1 90628
Patents Form No. 5
NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION
a new drug containing a cyclopentyl-aldehyde derivative and composition containing same vwegociete a re g p oil cadility limited dite : institut de
RECHERCHES CHIMIQUES ET BIOLOGIQUES ilPPLIQUEES (I.R.C.E.B.A.), /t/nt-tcaf /'<£>&'/'fa/
a French^company, of 28, rue de Teheran, 75008 Paris, France hereby declare the invention, for which 3/we pray that a patent may be granted to we/us, and the method by which it is to be performed, to be particularly described in and by the following statement
- 1 - (Mfem4 ty P«f« 'A ^
- 1 ft -
A new drug containing a cyclopentylaldehyde derivative and composition containing same.
This invention is concerned with a "new drug which belongs to the family of the cyclo-5 pentyl-aldehyde derivative, and with a therapeutical composition containing a cyclopentylaldehyde derivative as active ingredient.
More precisely the invention relates to a cyclopentyl-aldehyde derivative useful in therapy, 10 which is selected from the group consisting of a)compounds of the general formula
A-X
(I)
$ ^
;r i zr y wherein X and Y, which can be the same or different represent CHO, CH^OH or COOH; Z represents a C^-C^ 15 alkyl group; A represents -CH^-, ^ CcrCH^ or ^CH(CH^);
and b) their geometrical isomers.
Compounds of formula I are known compounds which can be prepared either by synthesis or 20 by extraction from a plant belonging to the Labiatae family such as the Teucrium marum , Teucrium polium aild Teucrium montanum species. For instance they can be extracted from Teucrium marum according to the method disclosed by PAGNONI et al., in Aust, J. Chem, (1976), 25 29, pages 1375-1381, article wherein their pharmaceutical properties are not described •
Now it has been surprisingly found that cyclopentyl-aldehyde derivatives according to formula I are (i) active as bacteriostatic, bacteri-30 cide, antispasmodic, antianaphylactic and antiphlogistic agents, and (ii) useful in particular in the treatment of human beings and warm-blooded animals suffering
2
190628
from infections diseases induced by"Gram(+)and Gram (-)" germs,and allergies such as hay fever.
aldehyde derivatives of formula I are more interesting, from a pharmaceutical point .of view, than the Teucrium marum extracts according to US patent No. k 151 278.
the definition of the general formula I, can be cited the following ones:
- Ex. 1: cK -( 2-f ormyl-3-niethyl-cyclopentyl)-acetaldehyde (X = Y=CHO; A = CH2; Z = CH^) ,
- Ex. 2: 2-( 2-hycLroxymethyl-3-methyl-cyclopentyl) -ethanol ( X = Y = CH2OH;A = CH2; Z = CH^) ,
- Ex. 3^ °C~( 2-carboxy-3-methyl-cyclopentyl)- acetic acid (X = Y = COOH; A = CH2; Z = CH ) ,
- Ex. 4: Q<( -(2-formyl-3-niethyl-cyclopentyl)-acrylaldehyde (X = Y = CHO; A = )C = CH2; Z = CH^) ,
- Ex. 5 • 2- ( 2-hydr oxymethyl-3-methyl-cyclopentyl)-2-
propen-1-ol (X = Y = CH0OH; A =>C = CHn; Z = CH,) ,
d, ^ 3
- Ex. 6: p< - ( 2-carboxy-3-methyl-cyclopentyl) - acrylic acid (X = Y = COOH; A =, C = CH2; Z = CH^) , and
- Ex. 7' 2- ( 2-hydroxymethyl-3-me thyl-cyclopentyl) -propan-l-ol ££ = Y = CH OH; A =^CH(CH_); Z = CH 7,
which all correspond to the following formula:
(wherein A and X are defined as above) , and present mainly two isomers:
On the other hand cyclopentyl-
Amongst the compounds included within
(II)
X
(A)
(B)
PAT&r
1 9
/7
vO
the"cis~trans" isomer being, in a general manner, more active than the "trans-cis"one.
The preferred compounds are those of examples 1 and 4. The most interesting one, from a 5 therapeutical point of view, is the compound of example
4.
The best mode for preparing the "acryl" compounds (A=^ C = CH^) consists in (i)
extracting o<-(2-formyl-3- methyl-cyclopentyl)-acrylal-10 dehyde from a Teucrium species such as Teucrium marum, Teucrium polium, Teucrium montanum, and (ii) transforming CHO into CH^OH by reduction or into COOH by oxidation. The compounds wherein A is CH(CH_)
such as example 7 are obtained by catalytic hydrogenation 15 of C =CH2* The compounds wherein A is CH2 are in particular prepared by synthesis according to a method known .per se.
PREPARATION I
obtention of -(2-formyl-3-methyl-ayclopentyl)-acr^l-20 aldehyde (Example 4)
1210 g of dried and ground Teucrium polium (entire plant) were extracted in a column successively with 7*35 1 of hexane and 7-25 1 of chloroform. The chloroform extract was evaporated to dryness 25 under vacuum and the residue thus obtained (47 g)
was steam distilled. The distillate was saturated with sodium chloride then extracted with chloroform. After drying on Na^SO^ the chloroform was distilled off under reduced pressure (0.3 mm Hg) to give 7.3 g (yield 0.
2 5 0 C
of a yellow oil (n^ = 1.4842) comprising a CfcHJ-CH0
89% by weight of '
H^C # CHO
('"Qis-trans")
and
1 906 28
4
11% by weight of c(=ch2)-cho
CHO
("trans-cis")
PREPARATION II
Obtention of ( 2-formyl-3-methyl-cyclopentyl) -acryl-aldehyde (example 4)
kg of dried and ground Teucrium marum (entire plant) were extracted by lixiviation in a
glass column (height: 2m; diameter: 0.225 m) fed in solvent by means of a pomp having a delivery of 10 1/h.
Two solvents were successively used: hexane (170 1)
then chloroform (170 1} . The hexane extract was discarded.
The chloroform extract was evaporated to dryness
under vacuum in order to obtain a brown oily residue
(640g) which was steam distilled. The distillate was saturated with NaCl when extracted with chloroform.
The chloroform phase was dried over NaSO^, the solvent was evaporated and the remaining oil was distilled
(under 1 mm Hg at 60-78°C) to give 42 g of a yellow 25° C
oil (n^ = 1.4842) which comprised:
- 87% by weight of the "cis-trans" isomer , and
- 13% by weight of the "trans-cis" isomer.
PREPARATION III
Obtention of 2- (2-hydroxymethyl-3-methyl-cyclopentyl) -2-propen-l-ol (example 5)
By reduction of the "cis-trans"
isomer of example 4 (1.4g) in solution in CH OH (25ml)
/ \ U
with NaBH^ (1.7 g) , the cis-trans isomer of example 5 30 (1019 g) is obtained in the form of an oil. According to the same method the trans-cis isomer of example 5 is
4> //
prepared from the trans-cis isomer of example 4.
1906 2 8
PREPARATION IV
Obtention of 2-(2-hydroxymethyl-3-methyl-cyclopentyl)-propan-l-ol (example 7)
The"cis-trans" and respectively "trans-5 cis" isomers of example 7 were obtained by hydrogenation on PtOg of the "cis-trans" and respectively "trans-cis" isomers of example 5 according to the method disclosed by PAGNONI et al.
The pharmaceutical assays which 10 have been carried out with examples 1 and k are summed up hereinafter.
1°) Assays with example 1 a) Bacteriostatic activity.
c< -(2-formyl-3-methyl-cyclopentyl)-acetaldehyde 15 inhibits Gram (+) and Gram (-) bacteriae. Its MIC
values are: 0.75 mg/ml on Staphylococcus aureus London,
1.2 mg/ml on Escherichia coli, and 1.5 mg/ml on Proteus 20 b) Antispasmodic activity
The ED-50 values ofoC-(2-formyl-3-methyl-cyclopentyl)-acetaldehyde have been determined
(i) in vitro on isolated ileum of guinea-pig against histamine: 25 ED - 50 = 50 If/ml;
(ii) in vivo on the entire animal according to the method of K0NZETT and R0ESLLER: ED - 50 = 2.6 mg/kg by i.v. route, c) Antianaphylactic activity 30 Male guinea-pigs are sensitized by two injections at the interval of two days of 0.5 ml of a 2g/l albumen solution. Four weeks after the lethal anaphylactic shock is provoked by i.v.
injection of 0.2 ml of a 2g/l ovalbumen solution. The 35 products to be tested are administered 30 minutes before (by i.p. route) or at the time (by i.v.route)
%
1 906 2 8
of the provoking injection. The results are given in table 1 for example 1 and Promethazine, a reference product.
TABLE I
Compound (dose)
mortality
%
protection
°/°
control
CO O
SO
%
Promethazine (20 mg/kg i.p.)
0%
100%
Example I
(10 mg/kg i.p.)
50%
50%
Example I (2mg/kg i.v.)
0%
100%
2°) Assays with Example 4 (consisting of a mixture 15 of 87% by weight of the "cis-trans" isomer and 13%
by weight of the "trans-cis" isomer).
a) Bacteriostatic activity
Example 4 inhibits Gram (+) and Gram (-) bacteriae. Its MIC values are:
1.5 mg/m on Staphylococcus aureus, London
1 mg/ml on Escherichia coli (strain 548),
lo75 mg/ml on Proteus vulgaris (strain 1557)*
2.5 mg/ml on Klebsiella pneumoniae (strain 433)«
1 mg/ml on Salmonella typhi murium (strain IP), 25 1.5 mg/ml on Staphylococcus aureus (strain 634),
1.25 mg/ml on Streptococcus (strain II78),
1.25 mg/ml on Bacillus substilis,
(strains 548, 1557, 433, 634 and 1178 belonging to the catalogue of the collection of the "Centre 30 International de Distribution de Souches et d'Information surles Types Microbiens" of Lausanne, and the "IP"
strain being provided from the Institut
7
I 90628
Pasteur" of Paris)
b) Bactericide activity
Example 4 kills Gram (+) and Gram (-) bacteriae. Its MBC (minimal bactericide concentration) values determined on solid medium (when less than 0.01 % of the germs survives) are:
1.75 mg/ml on Staphylococcus aureus London,
1.5 mg/ml on Escherichia coli (strain 548) ,
2 mg/ml on Proteus vulgaris (strain 1557) t
3 mg/ml on Klebsiella pneumoniae (strain 433)»
1.25 mg/ml on Salmonella typhi murium (strain I.P.), 1.75 mg/ml on Staphylococcus aureus (strain 634) , 2 mg/ml on Streptococcus (strain H78) ,
2.5 mg/ml on Bacillus substilis.
c) Antibronchospasmic activity
Guinea pigs (20 animals (weighing 300 - 500 g) per dose and per product to be tested) are preliminary subjected to an aerosol of Example 4 (50 g/1 in a water-ethanol solution) or Promethazine (a reference product) for 10 minutes. Then the animals are subjected individually to an histamine aerosol (3g/l of histamine in an aqueous medium containing 200g/l of glycerin)„ The time comprised between the beginning of the exposure to the histamine aerosol and the apnea with fall of the animal is measured.The control batch received only the histamine aerosol. The results given in table II show that Example 4 exhibits a bronchodilating effect which opposed the broncho-constrictor effect of histamine.
TABLE II
Product (dose)
Apparition of ; :apnea
(in seconds)
Variation with respect to control
Control Promethazine (0.1 mg/kg
108 + 18 > 600
- 13 MAR 1981
taPMwa*"*'
p;\ RECSVED ^
8
190628
TABLE II cont.
Product (dose) ^
Apparition of apnea
(in seconds)
Variation with respect to control
Ex 4 (1 mg/kg) Ex 4 (10 mg/kg)
130 + 23 * I69 + 32 *
t
+ 20% + 56%
Note:
* statistically significant (p< 0.05)
d) Antianaphylactic activity in vitro
Male guinea pigs are sensitized by an i.p. injection of lOO mg/kg of ovalbumen in an equal volume of Freund's adjuvant. Four weeks after the animals are slaughtered, each ileum is recovered and placed at 33°C in a Thyrode medium. Constriction is.obtained by addition of 200 jig of albumen to the liquid of surviving. The amplitude of the constrictions of the control ileum is compared with the amplitude of the constrictions after putting into contact example 4 for 2 minutes. The results given in Table III show that example 4 reduces the constriction amplitude of isolated guinea pig ileum, said reduction being statistically signifipant.
in vivo
Guinea pigs (male or female) are sensitized as indicated above with ovalbumen four weeks before the beginning of the experiment. Each animal is subjected to an oyalbumen aerbsol (obtained from an aqueous medium containing 50g/l of ovalbumen).
The anaphylactic shock comes out. by apparition
JMZ PATgMT ajfetCg-
" 13 MAR 1981 \
9
\ 906 21
of intense dyspnea. The apparition times of said dyspnea are compared between control animals and treated animal preliminary treated with an aerosol of example 4 (50 g/1 in a water-ethanol solution). The 5 results given in Table IV show that example 4 increases the time of apparition of respiratory troubles induced by ovalbumen aerosol.
TABLE III
Product (dose)
number of animals constriction amplitude amplitude variation with respect to control animals control
147 + 32
Ex 4
91 + 37*
38°/0
Ex 4
(10 jig/ml) 20
52 + 16*
65%
Note * statistically significant (p< 0.05)
.1 906X
TABLE IV
Product
Number of
Dyspnea
(dose)
animals time of time varia
apparition tion with
(seconds)
respect to
control
animals control
94 + 39
- •
Ex 4
(1 mg/kg
120 + 52
+ 28%
Ex 4
(10 mg/kg)
130 + 54
+ 38%
e) Antiphlogistic activity
The antiphlogistic activity of example 4 was studied on female rats (weighing 100 g) according to the 15 carrageen oedema test. The results are given in table V in which Indometacine is used as a reference product.
TABLE V
Product
Number dose inhibition with
of
(per rat)
respect to control
animal
animal
Ex 4
/ig
26%
Ex 4
50 jLlg
%
Ex 4
200 jag
41%
Indome t ac ine
200 jig
57%
f) Antispasmodic activity
The antispasmodic activity of example 4 was studied on isolated rat duodenum against acetylcholine and baryum chloride„ The ED-50 values of example 4 are: 30 (i) 13 jug/ml against acetylcholine (0.2 jag/ml), and (ii) 10 p.g/ml against BaClg (0.3 jig/ml)
11
1 906 2
Toxicity.
The LD - 50 values on mice of example 4 are
LD-50 i.p = 18 + 3 mg/kg
LD-50 i.v, = 20 + 3 mg/kg
LD-50 p.o.= 282+ 3 mg/kg
LD-50 s.c. >1000 mg/kg
LD-50 aerosol = 22 + 3 nig/kg
The invention includes within its scope a therapeutic composition comprising, in association with a physiologically acceptable excipient, a pharmaceutically effective amount of a cyclopentyl-aldehyde derivative of formula I
Such-a composition can be administered orally in the form of tablets, dragees, syrups and potable ampoules, by injection, and by spray.
The best mode for carrying out the invention consists in administering to human beings and warm-blooded animals the compound of example 4 or its "cis-trans" isomer, preferably in the form of spray or aerosol (in solution in carbitol or in suspension in freon or in a freon-alcohol mixture). When a spray or an aerosol is used it will contain from 0.1 to 10% of example 4 or its "cis-trans" isomer.
Example 4 and its "cis-trans"isomer can also be administered per os in the form of soft capsules (in oily solution) gelules (with a viscous or solid excipient), the preferred exipient being polyoxy-ethylenated oleic glycerides obtained by alcoholysis of a natural vegetal oil and which are sold under the name of LABRAFIL.
The corpounds of Formula I, in particular Example 4 and its "cis-trans" isomer, are useful in the treatment of infectious diseases, allergies such as hay fever and asthma (taking into account their antianaphylactic activity), inflammations and algiae.
12
. 1<)0G28
Claims (4)
- (I) wherein X and Y, which can be the same or different, represent CHO, CH2OH or COOH; Z represent a cx-^3 alkyl group; A represents -C^-, ^C = CH2 or ^CHfCH^); and b) their geometrical isomers.
- 2) A therapeutic composition according to claim 1 characterised in that the cyclopentyl-aldehyde derivative is a-(2-formyl-3-methyl-cyclopentyl)-acrylaldehyde.
- 3) A therapeutic composition according to claim 2 characterised in that the cyclopentyl-aldehyde derivative is a-(2-formyl-3-methyl-cyclopentyl)-acrylaldehyde in the form of the cis-trans isomer.
- 4) A method for the treatment of infectious diseases and allergies in a non-human animal comprising administering to the non-human animal an effective amount of a cyclopentyl-aldehyde of the formula las defined in claim! or one of_its geometrical isomers. \\ /> ir-'n.-j-BALDWIN, SON & CAREY ^ attorneys for the applicants
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7826316 | 1978-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ190628A true NZ190628A (en) | 1984-11-09 |
Family
ID=10497850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ190628A NZ190628A (en) | 1978-06-03 | 1979-06-01 | Therapeutic compositions containing cyclopentyl aldehyde derivatives |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0006061B1 (en) |
| JP (1) | JPS5513269A (en) |
| AT (1) | ATE715T1 (en) |
| AU (1) | AU4760079A (en) |
| BE (1) | BE876713A (en) |
| CA (1) | CA1107761A (en) |
| CH (1) | CH639929A5 (en) |
| DE (1) | DE2962180D1 (en) |
| FR (1) | FR2427094B1 (en) |
| GB (1) | GB2022413B (en) |
| IE (1) | IE48343B1 (en) |
| IL (1) | IL57433A (en) |
| IT (1) | IT1120984B (en) |
| LU (1) | LU81352A1 (en) |
| NZ (1) | NZ190628A (en) |
| ZA (1) | ZA792678B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0505572A4 (en) * | 1990-10-09 | 1993-03-10 | Tsumura & Co. | Iridoide derivative and its use as medicine |
| CN102942605B (en) * | 2012-11-30 | 2016-06-15 | 沈阳药科大学 | The preparation method of iridoid and application thereof in Jasminum lanceolarium Roxb. |
| US20230159426A1 (en) * | 2020-04-14 | 2023-05-25 | Firmenich Sa | Lily of the valley odorant |
-
1979
- 1979-05-29 AT AT79400340T patent/ATE715T1/en not_active IP Right Cessation
- 1979-05-29 IL IL57433A patent/IL57433A/en unknown
- 1979-05-29 CH CH500979A patent/CH639929A5/en not_active IP Right Cessation
- 1979-05-29 DE DE7979400340T patent/DE2962180D1/en not_active Expired
- 1979-05-29 EP EP79400340A patent/EP0006061B1/en not_active Expired
- 1979-05-30 CA CA328,873A patent/CA1107761A/en not_active Expired
- 1979-05-30 AU AU47600/79A patent/AU4760079A/en not_active Abandoned
- 1979-05-30 ZA ZA792678A patent/ZA792678B/en unknown
- 1979-05-31 FR FR7914041A patent/FR2427094B1/en not_active Expired
- 1979-06-01 BE BE2/57846A patent/BE876713A/en not_active IP Right Cessation
- 1979-06-01 LU LU81352A patent/LU81352A1/en unknown
- 1979-06-01 NZ NZ190628A patent/NZ190628A/en unknown
- 1979-06-01 IT IT68189/79A patent/IT1120984B/en active
- 1979-06-04 JP JP6980179A patent/JPS5513269A/en active Pending
- 1979-06-04 GB GB7919435A patent/GB2022413B/en not_active Expired
- 1979-08-08 IE IE1087/79A patent/IE48343B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2962180D1 (en) | 1982-03-25 |
| IT1120984B (en) | 1986-03-26 |
| FR2427094A1 (en) | 1979-12-28 |
| JPS5513269A (en) | 1980-01-30 |
| EP0006061A1 (en) | 1979-12-12 |
| AU4760079A (en) | 1979-12-13 |
| EP0006061B1 (en) | 1982-02-24 |
| IT7968189A0 (en) | 1979-06-01 |
| GB2022413A (en) | 1979-12-19 |
| BE876713A (en) | 1979-12-03 |
| ATE715T1 (en) | 1982-03-15 |
| IL57433A (en) | 1982-08-31 |
| CH639929A5 (en) | 1983-12-15 |
| CA1107761A (en) | 1981-08-25 |
| FR2427094B1 (en) | 1986-07-25 |
| GB2022413B (en) | 1983-02-16 |
| IL57433A0 (en) | 1979-09-30 |
| IE791087L (en) | 1979-12-03 |
| LU81352A1 (en) | 1980-01-22 |
| ZA792678B (en) | 1980-08-27 |
| IE48343B1 (en) | 1984-12-12 |
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