CN1114880A - Novel treatment - Google Patents
Novel treatment Download PDFInfo
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- CN1114880A CN1114880A CN93116874A CN93116874A CN1114880A CN 1114880 A CN1114880 A CN 1114880A CN 93116874 A CN93116874 A CN 93116874A CN 93116874 A CN93116874 A CN 93116874A CN 1114880 A CN1114880 A CN 1114880A
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- Prior art keywords
- chemical compound
- treatment
- administration
- day
- diabetes
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Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A method for the treatment and/or prophylaxis of obesity or for the treatment of Type II diabetes in mammals, such as humans, which comprises administering to the mammal in need of such treatment and/or prophylaxis an effective and/or prophylactic, non-toxic amount of Compound 1 (1,3-dicyclopropymethyl-8-amino-xanthine).
Description
The chemical compound that the present invention relates to treat and/or prevent the method for obesity or treatment type ii diabetes and be used for this method.
European patent application publication No. 0389282 has been described formula (A) chemical compound:
Or its pharmaceutically acceptable salt that is fit to, wherein R
1And R
2Represent alkyl or formula (a) part respectively:
-(CH
2)
mA (a) wherein m represents 0 or integer 1,2, or 3, the A representative replaces or unsubstituted cyclic hydrocarbon radical, condition is to work as R
1R during represent methylidene
2It or not methyl; With
R3a represents halogen atom, nitro, or group-NR
4R
5R wherein
4And R
5Represent hydrogen respectively, alkyl or alkyl-carbonyl or R
4And R
5Form a heterocyclic radical that replaces arbitrarily with the ammonia that is connected them.
The example 9 of EP903030930.0 is 1, the amino xanthine (after this preferably as chemical compound 1) of 3-bicyclic methyl propyl-8-.
Chemical compound with treatment cerebrovascular and neuronal degeneration disease activity has been described especially and as the phosphodiesterase inhibitor that improves ring AMP level in European application numbers 90303093.0.
We are surprised to find the absorption that chemical compound 1 can increase the consumption of energy and also can reduce food now, so it comprises that for the treatment mammal people's obesity is of great use.
It is that effectively therefore to treat type ii diabetes be effective that Compound I also demonstrates for improving insulin sensitivity.
Therefore, the invention provides a kind of mammal that treats and/or prevents, as the method for people's obesity or treatment type ii diabetes, this method comprises that the mammal that needs is given in chemical compound 1 administration of nontoxic amount with treatment and prevention effective dose and/or prevention.
The present invention also is provided for treating and/or preventing the chemical compound 1 of obesity or treatment type ii diabetes.
Another aspect of the present invention provide a kind of be used for the treatment of and/or prevent obesity or the treatment type ii diabetes pharmaceutical composition, said composition comprises chemical compound 1 and pharmaceutically acceptable carrier.
The present invention also on the one hand provides chemical compound 1 to be used to prepare to treat and/or prevent the purposes of the sick medicine of obesity or treatment II type sugar.
Mammal is given in administration can pass through oral or parenterai administration.
The effective dose of treatment of obesity or type ii diabetes is according to general factor such as mammiferous person's character, and the order of severity and the body weight of the state of an illness decide.Then, unit dose contains 0.1 to 200mg usually for example 5 to 50mg or 1 to the chemical compound 1 of 20mg.Unit dose is usually with once a day or more than single administration, every day 1,2,3 for example, 4,5 or 6 times, more generally every day 1-4 times, therefore be generally 0.5 to 500mg for the total daily dose of 70Kg adult, for example 50 to 250mg or 10 arrive 150mg, be that its scope is about 0.001 to 10mg/Kg/ days, more generally 1 to 3mg/Kg/ days or 0.2 to 2.5mg/Kg/ days, for example 0.7 to 2mg/Kg/ days.
Preferably, chemical compound 1 is with the units dosage composition form administration, as the oral or non-intestinal compositions of unit dose.
By being mixed with this compositions and adopting suitable oral or parenterai administration, as being tablet, capsule, oral liquid, powder, granule, lozenge, recombinant powder, but injection and infusion solution or suspension emulsion.Orally administered composition is preferred, and molding port oral compositions particularly is because they are more convenient for common use.
Oral tablet and capsule exist with unit dose usually, and contain conventional excipients such as binding agent, filler, and diluent becomes tablet, lubricant, disintegrating agent, coloring agent, flavoring agent and wetting agent.Tablet can carry out coating according to known method of the prior art.
Available suitable filler comprises cellulose, mannitol, lactose and other similar filler.The disintegrating agent that is fit to comprises starch, polyvinylpyrrolidone and starch derivatives such as Explotab.The lubricant that is fit to comprises for example magnesium stearate.The pharmaceutically acceptable wetting agent that is fit to comprises sodium laurylsulfate.
Methods such as these solid oral compositions can mix by conventional, fill, and are in blocks prepare.Can use the remix operation to utilize a large amount of filleies to disperse the activating agent of whole compositions.Certainly, this operation is a routine techniques.
For example, oral liquid can be aqueous solution or oily suspension, solution, and emulsion, the form of syrup or elixir, or exist with dryed product, before use with water or other appropriate excipients remix.This liquid preparation can contain conventional additives such as suspending agent, for example Sorbitol, syrup, methylcellulose, gelatin, hydroxyethyl-cellulose, carboxymethyl cellulose, stearic acid aluminium glue or hydrogenation edible fat.Emulsifying agent, lecithin for example, single oleic acid sorbitan ester, or Radix Acaciae senegalis; Non-water excipient (can comprise edible oil), almond oil for example, fractionated coconut oil, grease such as glyceride, propylene glycol, or ethanol; Antiseptic, for example right-methyl hydroxybenzoate or propyl ester or sorbic acid; And to contain conventional flavoring agent or coloring agent if desired.
Oral formulations also comprises conventional extended release preparation such as tablet or contains the granule of enteric coating.
For parenterai administration, can prepare the liquid unit doses form that contains chemical compound 1 and sterilization excipient.According to excipient and concentration, the chemical compound 1 also solubilized that both can suspend.Non-intestinal solution usually by with compound dissolution in excipient and be filled into suitable bottle or ampoule bottle and sealing preceding filtration sterilization.With adjuvant such as local anesthetic, it also is favourable in the excipient that antiseptic and buffer agent are dissolved in.In order to improve stability, compositions freezing and vacuum after being filled into bottle can be removed and anhydrate.
The also available essentially identical method preparation of non-intestinal suspension is except being suspended in chemical compound in the excipient rather than dissolving and sterilize by being exposed in the oxirane before in being suspended in the sterilization excipient.Advantageously, in compositions, also comprise surfactant or wetting agent, so that the uniform distribution of favourable chemical compound.
Following pharmacological datum has proved the in test activity of chemical compound 1, and this test explanation chemical compound is for the potential purposes of treatment of obesity.The pharmacological datum test procedure
Experimental animal is 12 male and 12 female Sprague-Dawley Mus (body weight 200-270g, about 8-10 age in week).
Mus is fed SQC Mus and mice and is kept diet number 1; Diet and water can at will obtain.
Temperature and relative humidity are remained on 21 ± 2 ℃ and 55 ± 10% respectively, and 12 hours lights were given in brilliance control at per 24 hours.
After adaptation in 6 days, animal is divided into two groups (matched group and treatment groups) by stratified random, to obtain the group that average weight approximately equates.Every group contains 6 male Mus and 6 female Mus.Mus is stayed in together for 3 one group.
After benchmark was observed in 4 days, all animals are being begun administration on the same day.With all animals administers once a day, totally 10 days.
Test compound is organized oral administration with the suspending agent of 1% methylcellulose of 1mg/Kg/ days dosage levels to treatment by gavage.
Animal is carried out administration with the constant dosage volume of 1ml/100g body weight.The same dose volume of control animals is given excipient separately.
Absorption record every day of food and water.Body weight between 1. groups (g) compares the sky as a result
Male treatment of control group group 1 average 269.3 266.8NS
% poor--1
S.D. 9.6 4.1
(N) (6) (6) 11 meansigma methodss 318.3 268.5
*
% poor--16
S.D. 13.7 12.0
(N) (6) (6)
Female 1 meansigma methods, 210.3 206.8NS
% poor--2
S.D. 5.4 3.0
(N) (6) (6) 11 meansigma methodss 227.8 211.2
*
% poor--7
S.D. 12.4 8.5
(N) % difference in (6) (6) is calculated on the data basis that does not round up.For Student " t "-test (the 2-tail) significant level:
*P＜0.05
*The inapparent NT of P＜0.01NS not between 2. groups of test body weight increase (g) relatively
Treatment of control group group sky
Male 1-11 meansigma methods 49.0 1.7
*
% poor--97
S.D. 10.1 9.4
(N) (6) (6)
Female 1-11 meansigma methods 17.5 4.3
*
% poor--75
S.D 9.5 7.5
(N) % difference in (6) (6) is to calculate on the data basis that does not round up.For Student " t "-test (the 2-tail) significant level:
*P＜0.05
*Food consumption relatively between＜0.013. group
(g/ animal/sky)
Treatment of control group group sky
Male 1-10 meansigma methods 28.7 22.1
% poor--23
(N) (2) (2)
Female 1-10 meansigma methods 21.5 19.9
% poor--7
(N) % difference in (2) (2) is calculated on the data basis that does not round up.4. water consumption is compared between the group
(g/ animal/sky)
Treatment of control group group sky
Male 1-10 meansigma methods 30.6 27.5
% poor--10
(N) (2) (2)
Female 1-10 meansigma methods 25.6 30.0
% poor-+17
(N) % difference in (2) (2) is calculated on the data basis that does not round up.1. food intake in 19 of Mus hours
Arbitrarily feed ball shape food and single being placed in the illumination circulation with male Sprague-Dawley Mus (420-550g), lamp is closed from 6pm-6am.With chemical compound 1 or excipient in the 2.30pm administration and from this moment measuring the absorption of food and the change of body weight to second day 10am.The result is meansigma methods ± SEM (n=6).Chemical compound 1 dosage 015 (mg/Kg p.o.) food intake (g) 25.0 ± 2.3 11.0 ± 3.5
13.8 ± 2.8
1Body weight loss (g) 1.0 ± 1.9 27.0 ± 1.2
132.0 ± 3.4
1
1P＜0.001 comparative control is worth the food intake in 20 hours of 2. mices
Arbitrarily feed ball shape food with female GFLP mice (29-37g) and also be placed in pairs in the illumination circulation, lamp is closed from 6pm-6am from 6pm.Chemical compound 1 or excipient are measured food intake and body weight change in the 2pm administration and in following 20 hours.The result is meansigma methods ± SEM5 (food intake) or meansigma methods ± SEM10 (body weight).12.1 ± 10.5 ± 6.5 ± 5.4 ± 4.2 ± every couple (g) 1.2 1.1 1.5 of chemical compound 1 dosage 0 0.3 135 (mg/Kgp.o) food intake
*1.0
*0.8
* *Body weight loss (g) 0.94 ± 1.50 ± 2.71 ± 3.77 ± 4.45 ±
0.25 0.32 0.71
*0.29
* *0.57
*P＜0.05;
*P＜0.01,
* *P＜0.001 comparative control
Value.3. mice food intake in 4 hours
Female GFLP mice (22-34g) is placed and feeds ball shape food in pairs.Make them in 1 all endoadaptation illumination circulations, 12 from 12 noon to night on this lamp is closed.Between 11.30am to 12.15pm with chemical compound 1 or excipient administration and (3.30pm to 4.15pm) food intake after estimating 4 hours.The result is meansigma methods ± SEM (n=5).5.83 ± 5.14 ± 4.88 ± 3.80 ± 3.06 ± 2.74 ± every couple (g) 0.25 0.39 0.25 of chemical compound 10 0.03 0.1 0.3 1.0 3.0 dosage (mg/Kg p.o) food intake
*0.36
*0.17
* *0.31
* *Toxicity
Do not produce unfavorable toxicology effect in the above in the test of mentioning.The physical qualification of experimental animal discloses for treatment and does not show any side reaction.
Claims (9)
1. one kind treats and/or prevents mammal, as people's the obesity or the method for treatment type ii diabetes, this method comprises and will treat and/or prevent effective dose and/or prevent 1 of nontoxic amount that the mammal that needs is given in amino xanthine (chemical compound 1) administration of 3-two-cyclopropyl methyl-8-.
2. according to the process of claim 1 wherein that the administration of chemical compound 1 is by oral or parenterai administration.
3. according to the process of claim 1 wherein that chemical compound 1 is with the units dosage composition form administration.
4. according to the method for claim 3, wherein unit dose contains 0.1 to 200mg chemical compound 1.
5. according to the method for claim 3, wherein unit dose contains 5 to 50mg or 1 to 20mg chemical compound 1.
6. according to the process of claim 1 wherein that the administration scope of chemical compound 1 is about 0.001 to 10mg/Kg/ day.
7. according to the process of claim 1 wherein that chemical compound 1 administration scope is 1 to 3mg/Kg/ day, 0.2 to 2.5mg/Kg/ day or 0.7 to 2mg/Kg/ day.
8. 1, the purposes of the amino xanthine of 3-two-cyclopropyl methyl-8-(chemical compound 1) comprises being used for the treatment of and/or the manufacturing of the medicine of prevent obesity or treatment type ii diabetes.
9. one kind is used for the treatment of and/or the pharmaceutical composition of prevent obesity or treatment type ii diabetes, and said composition comprises 1, amino xanthine (chemical compound 1) of 3-two-cyclopropyl methyl-8-and pharmaceutically acceptable carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9215633.0 | 1992-07-23 | ||
| GB929215633A GB9215633D0 (en) | 1992-07-23 | 1992-07-23 | Novel treatment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1114880A true CN1114880A (en) | 1996-01-17 |
| CN1043610C CN1043610C (en) | 1999-06-16 |
Family
ID=10719151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93116874A Expired - Lifetime CN1043610C (en) | 1992-07-23 | 1993-07-22 | Novel treatment |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0651642A1 (en) |
| JP (1) | JPH07509456A (en) |
| CN (1) | CN1043610C (en) |
| AU (1) | AU4714393A (en) |
| GB (1) | GB9215633D0 (en) |
| MX (1) | MX9304435A (en) |
| TW (1) | TW258663B (en) |
| WO (1) | WO1994002150A1 (en) |
| ZA (1) | ZA935339B (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5783408A (en) * | 1995-06-07 | 1998-07-21 | Hamilton; Bradford S. | Method for screening potential anti-obesity agents |
| ATE353900T1 (en) * | 2001-02-24 | 2007-03-15 | Boehringer Ingelheim Pharma | XANTHINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS MEDICINAL PRODUCTS |
| ATE388951T1 (en) * | 2001-07-03 | 2008-03-15 | Novo Nordisk As | DPP-IV INHIBITING PURINE DERIVATIVES FOR THE TREATMENT OF DIABETES |
| US6869947B2 (en) | 2001-07-03 | 2005-03-22 | Novo Nordisk A/S | Heterocyclic compounds that are inhibitors of the enzyme DPP-IV |
| JP2005509603A (en) * | 2001-09-19 | 2005-04-14 | ノボ ノルディスク アクティーゼルスカブ | Heterocyclic compounds that are inhibitors of the DPP-IV enzyme |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| DE10254304A1 (en) * | 2002-11-21 | 2004-06-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New xanthine derivatives, their production and their use as medicines |
| MXPA06002521A (en) | 2003-09-05 | 2006-06-20 | Altana Pharma Ag | Use of pde4 inhibitors for the treatment of diabetes mellitus. |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004030502A1 (en) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel imidazoles and triazoles, their preparation and use as medicines |
| DE102004054054A1 (en) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Process for preparing chiral 8- (3-amino-piperidin-1-yl) -xanthines |
| EA015382B1 (en) | 2005-03-08 | 2011-08-30 | Никомед Гмбх | Use of roflumilast for the treatment of diabetes mellitus type 2 |
| DE102005035891A1 (en) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8- (3-amino-piperidin-1-yl) -xanthines, their preparation and their use as pharmaceuticals |
| PE20080251A1 (en) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | USES OF DPP IV INHIBITORS |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| CN102838599A (en) | 2006-05-04 | 2012-12-26 | 贝林格尔.英格海姆国际有限公司 | Polymorphs |
| PE20140960A1 (en) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | FORMULATIONS INVOLVING A DPP4 INHIBITOR |
| UY32030A (en) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "TREATMENT FOR DIABETES IN INAPPROPRIATE PATIENTS FOR THERAPY WITH METFORMIN" |
| BRPI0916997A2 (en) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | DPP-4 INHIBITOR AND ITS USE |
| AU2009290911A1 (en) | 2008-09-10 | 2010-03-18 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| AU2009331471B2 (en) | 2008-12-23 | 2015-09-03 | Boehringer Ingelheim International Gmbh | Salt forms of organic compound |
| AR074990A1 (en) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | TREATMENT OF DIABETES IN PATIENTS WITH AN INAPPROPRIATE GLUCEMIC CONTROL THROUGH METFORMIN THERAPY |
| KR102668834B1 (en) | 2009-11-27 | 2024-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | Treatment of genotyped diabetic patients with dpp-iv inhibitors such as linagliptin |
| ES2935300T3 (en) | 2010-05-05 | 2023-03-03 | Boehringer Ingelheim Int | combitherapy |
| KR20230051307A (en) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | Diabetes therapy |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| EA030121B1 (en) | 2011-07-15 | 2018-06-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| WO2013171167A1 (en) | 2012-05-14 | 2013-11-21 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in the treatment of podocytes related disorders and/or nephrotic syndrome |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| ES2950384T3 (en) | 2014-02-28 | 2023-10-09 | Boehringer Ingelheim Int | Medical use of a DPP-4 inhibitor |
| EP4233840A3 (en) | 2016-06-10 | 2023-10-18 | Boehringer Ingelheim International GmbH | Combinations of linagliptin and metformin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8906792D0 (en) * | 1989-03-23 | 1989-05-10 | Beecham Wuelfing Gmbh & Co Kg | Treatment and compounds |
-
1992
- 1992-07-23 GB GB929215633A patent/GB9215633D0/en active Pending
-
1993
- 1993-07-21 WO PCT/GB1993/001539 patent/WO1994002150A1/en not_active Application Discontinuation
- 1993-07-21 JP JP6504294A patent/JPH07509456A/en active Pending
- 1993-07-21 EP EP93917883A patent/EP0651642A1/en not_active Withdrawn
- 1993-07-21 AU AU47143/93A patent/AU4714393A/en not_active Abandoned
- 1993-07-22 CN CN93116874A patent/CN1043610C/en not_active Expired - Lifetime
- 1993-07-22 MX MX9304435A patent/MX9304435A/en unknown
- 1993-07-23 ZA ZA935339A patent/ZA935339B/en unknown
- 1993-07-27 TW TW082105967A patent/TW258663B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX9304435A (en) | 1994-04-29 |
| CN1043610C (en) | 1999-06-16 |
| JPH07509456A (en) | 1995-10-19 |
| WO1994002150A1 (en) | 1994-02-03 |
| AU4714393A (en) | 1994-02-14 |
| EP0651642A1 (en) | 1995-05-10 |
| GB9215633D0 (en) | 1992-09-09 |
| ZA935339B (en) | 1995-01-18 |
| TW258663B (en) | 1995-10-01 |
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