CN1135974C - Antimalarial compound dihydroartemisinin - Google Patents
Antimalarial compound dihydroartemisinin Download PDFInfo
- Publication number
- CN1135974C CN1135974C CNB001131346A CN00113134A CN1135974C CN 1135974 C CN1135974 C CN 1135974C CN B001131346 A CNB001131346 A CN B001131346A CN 00113134 A CN00113134 A CN 00113134A CN 1135974 C CN1135974 C CN 1135974C
- Authority
- CN
- China
- Prior art keywords
- medicine
- dihydroartemisinin
- piperaquine
- present
- dihydroarteannuin
- Prior art date
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 10
- 239000003430 antimalarial agent Substances 0.000 title claims description 8
- 229960002521 artenimol Drugs 0.000 title abstract description 9
- BJDCWCLMFKKGEE-ISOSDAIHSA-N artenimol Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-ISOSDAIHSA-N 0.000 title abstract description 9
- 229930016266 dihydroartemisinin Natural products 0.000 title abstract description 9
- 230000000078 anti-malarial effect Effects 0.000 title description 5
- 239000003814 drug Substances 0.000 claims abstract description 25
- UCRHFBCYFMIWHC-UHFFFAOYSA-N piperaquine Chemical compound ClC1=CC=C2C(N3CCN(CC3)CCCN3CCN(CC3)C=3C4=CC=C(C=C4N=CC=3)Cl)=CC=NC2=C1 UCRHFBCYFMIWHC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229950006717 piperaquine Drugs 0.000 claims abstract description 12
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960001082 trimethoprim Drugs 0.000 claims abstract description 7
- 229930187998 Dihydroarteannuin Natural products 0.000 claims description 14
- SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 claims description 5
- 229930191701 arteannuin Natural products 0.000 claims description 4
- 229960000981 artemether Drugs 0.000 claims description 4
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 claims description 4
- 229960004191 artemisinin Drugs 0.000 claims description 4
- 229960002970 artemotil Drugs 0.000 claims description 3
- NLYNIRQVMRLPIQ-XQLAAWPRSA-N artemotil Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OCC)O[C@H]4[C@]32OO[C@@]1(C)O4 NLYNIRQVMRLPIQ-XQLAAWPRSA-N 0.000 claims description 3
- FIHJKUPKCHIPAT-AHIGJZGOSA-N artesunate Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@@H](OC(=O)CCC(O)=O)[C@@H]4C FIHJKUPKCHIPAT-AHIGJZGOSA-N 0.000 claims description 3
- 229960004991 artesunate Drugs 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 201000004792 malaria Diseases 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 11
- 231100000053 low toxicity Toxicity 0.000 abstract description 5
- 230000000505 pernicious effect Effects 0.000 abstract description 4
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- VHBABGAFHUKREU-ICKLFXEKSA-N duo-cotecxin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C.ClC1=CC=C2C(N3CCN(CC3)CCCN3CCN(CC3)C=3C4=CC=C(C=C4N=CC=3)Cl)=CC=NC2=C1 VHBABGAFHUKREU-ICKLFXEKSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HQWQVBJUIIJTRE-LKRNKTNVSA-N 4-amino-n-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide;(s)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2r)-piperidin-2-yl]methanol;5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine;hydron;chloride Chemical compound Cl.CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1.COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC.C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 HQWQVBJUIIJTRE-LKRNKTNVSA-N 0.000 description 2
- 206010048723 Multiple-drug resistance Diseases 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- 208000035999 Recurrence Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960001962 mefloquine Drugs 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 208000002476 Falciparum Malaria Diseases 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 206010035500 Plasmodium falciparum infection Diseases 0.000 description 1
- 201000011336 Plasmodium falciparum malaria Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940098333 coartem Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- QMNFFXRFOJIOKZ-UHFFFAOYSA-N cycloguanil Chemical compound CC1(C)N=C(N)N=C(N)N1C1=CC=C(Cl)C=C1 QMNFFXRFOJIOKZ-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- -1 hydroxypropyl Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960004985 lumefantrine Drugs 0.000 description 1
- DYLGFOYVTXJFJP-MYYYXRDXSA-N lumefantrine Chemical compound C12=CC(Cl)=CC=C2C=2C(C(O)CN(CCCC)CCCC)=CC(Cl)=CC=2\C1=C/C1=CC=C(Cl)C=C1 DYLGFOYVTXJFJP-MYYYXRDXSA-N 0.000 description 1
- 229940001645 malarone Drugs 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002423 protozoacide Substances 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4706—4-Aminoquinolines; 8-Aminoquinolines, e.g. chloroquine, primaquine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The present invention provides a new medicine compound dihydroartemisinin for treating the pernicious malaria with multiple medicine resistance, which is prepared from components of dihydroartemisinin, piperaquine and trimethoprim. The medicine indicates that the medicine has the characteristics of immediate effect, high efficiency, low toxicity and short course of treatment by an animal experiment and clinical tryout; a therapeutic effect and a low-toxicity side effect are obviously superior to that of the current native and foreign medicine in the same class. Because of the match of two main components such as dihydroartemisinin and piperaquine of the present invention, the effect is good; the dihydroartemisinin and the piperaquine are important component parts of the patent of the present invention.
Description
The present invention relates to be used for the treatment of and prevent the compound dihydroartemisinin of pernicious malaria and other types malaria.
The multiple drug resistance pernicious malaria whole world spreads, and Southeast Asia is particularly serious.World Health Organization (WHO) has listed one of essential planning of 21 century to " containment malaria " in.Former mefloquine (Mefloquine) and compound recipe Fa Ximi (Fansimef) thereof are expressed very big hope, but because its drug-fast rapid appearance, at first in Thailand, then it is very poor to be in curative effect in Vietnam, and (Li Guoqiao etc. treat subtertian malaria in Vietnam Xuan Loc hospital with Fansimef in toxicity no small condition, cure rate 55%, unpublished data 1995).Arteannuin of having developed since China's the seventies and derivant artesunate thereof, Artemether, arteether, dihydroarteannuin etc. have efficient, quick-acting advantages, just can reach high curative rate in 7 days but must take medicine, otherwise the recrudescence rate height is unfavorable for the control of the malaria source of infection.
Switzerland NORVATIS drugmaker might be better than existing antimalarial from the technology Coartem (being made up of Artemether and benflumetol) that China buys, but still needs 3 days its course of treatment, and cost is higher.The Malarone that Britain Glaxo Wellcome company is developing, by how quinone (Naphthoquinone) and cyclochloroguanidum are formed, and do not have active remedy in its prescription, 3 days courses of treatment, take medicine every day 2 times.If with every day dose change into once and taking, then feel sick, the vomiting side effect is serious.
The object of the present invention is to provide the compound dihydroartemisinin of a kind of quick-acting, efficient, low toxicity, the pernicious Malaria of treatment multiple drug resistance of the short course of treatment.
Above-mentioned purpose of the present invention is to realize that by such technical scheme promptly a kind of antimalarial compound dihydroartemisinin is characterized in that: it is the medicament made from following weight (part) proportion raw material:
1 part of dihydroarteannuin (Dihydroartemisinin) or its similar medicine
3～7 parts of piperaquine (piperaquine)
0～5 part of trimethoprim (Trimethoprim)
The similar medicine of dihydroarteannuin is arteannuin and derivant thereof in the medicine of the present invention, as arteannuin, artesunate, Artemether, arteether.This type of medicine finally is converted into dihydroarteannuin and brings into play it and kill the protozoacide effect in body.
Above-mentioned solution of the present invention is based on pathogenetic understanding and the Therapeutic Principle of motherland's medical science to Malaria, draw with reference to the modern pharmacological research achievement, be that the principle that the present invention fills a prescription is: dihydroarteannuin has quick-acting, low toxicity, can kill the drug resistant falciparum malaria protozoon rapidly in a large number, but if discontinuous taking medicine 7 days, then relapse rate height; Piperaquine has long-acting characteristics, can make to shorten to 2 days the course of treatment; Can mend the deficiency of dihydroarteannuin; Trimethoprim is a kind of synergist, helps to improve cure rate and reduces recrudescence rate.Dihydroarteannuin can delay the drug-fast appearance of piperaquine and trimethoprim again.
The optimum weight of medicine of the present invention (part) proportioning is:
1 part of dihydroarteannuin
5 parts of piperaquine
2.5 parts of trimethoprims
Medicine of the present invention also can be the compatibility agent of dihydroarteannuin and piperaquine, and its optimum weight (part) proportioning is:
1 part of dihydroarteannuin
6 parts of piperaquine
Medicine of the present invention is through pharmacodynamics, toxicology, general pharmacology test and clinical research and researchs such as preparation technology, quality testing and study on the stability, and, the curative effect of subtertian malaria is tested in China Hainan Province and Vietnam, Thailand, the popular area of Cambodia's resistant malaria.Result of study proves that its curative effect to subtertian malaria is better than existing any antimalarial, can be used for treating subtertian malaria, ask day malaria and other types malaria, be in the world subtertian malaria to be had the cure rate height so far for this reason, parasite killing speed is fast and toxicity is low, and safety is big, and technology is simple, maturation, the new drug of good stability.Wherein one of main component piperaquine is without its phosphate, reduces dosage, alleviates side effect, reduced cost, and its maximum characteristics are to take simple and conveniently, only need take medicine and can cure for one day 2 times.Actual application value is very big.
Preparation of the present invention is that said medicine is combined with multiple pharmaceutically acceptable excipient or carrier; adopt mixing, dissolving, granulation, in flakes, known methods such as sweet tablet or film coating are prepared into the preparation of solid-state or liquid form, as tablet, capsule, suppository, granule and injection etc.
Above-mentioned each component is made medicine production method of the present invention is:
Earlier supplementary material is detected,, cross 100 mesh sieves, accurately take by weighing raw material and adjuvant by recipe quantity then qualified raw material pulverize separately.With each component mix homogeneously tabletting, packing is finished product.
For example: 1000 of production medicines of the present invention are by the following prescription amount of getting:
Dihydroarteannuin or its similar medicine 75g
Piperaquine 375g
Trimethoprim 1875g
Adjuvant (its cellulose of hydroxypropyl) is an amount of.
The taking dose of medicine of the present invention: adult consumption be 2 days, 4 of total dose of curative course, promptly 0 hour, 8 hours, 24 constantly with 32 hours, obey 1 at every turn.By 500 these medical instruments of many cases clinical trial certificate have immediate effect, efficiently, low toxicity, characteristics, its curative effect of the short course of treatment obviously be better than similar medicine both domestic and external at present.
Claims (3)
1, a kind of compound recipe new antimalarial agent that contains dihydroarteannuin is characterized in that the active component of this medicine is:
1 part of dihydroarteannuin
Piperaquine or its phosphate 3-7 part
Trimethoprim 0-5 part.
2, compound recipe new antimalarial agent as claimed in claim 1 is characterized in that dihydroarteannuin can use arteannuin, artesunate, Artemether, arteether to substitute.
3, compound recipe new antimalarial agent as claimed in claim 1 is characterized in that pharmaceutical dosage form is tablet, capsule, suppository, granule and injection.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001131346A CN1135974C (en) | 2000-08-23 | 2000-08-23 | Antimalarial compound dihydroartemisinin |
| AU2001289506A AU2001289506A1 (en) | 2000-08-23 | 2001-05-31 | Pharmaceutical composition of dihydroartemisinin for treating malaria |
| PCT/CN2001/000884 WO2002026226A1 (en) | 2000-08-23 | 2001-05-31 | Pharmaceutical composition of dihydroartemisinin for treating malaria |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001131346A CN1135974C (en) | 2000-08-23 | 2000-08-23 | Antimalarial compound dihydroartemisinin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1305810A CN1305810A (en) | 2001-08-01 |
| CN1135974C true CN1135974C (en) | 2004-01-28 |
Family
ID=4582950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB001131346A Ceased CN1135974C (en) | 2000-08-23 | 2000-08-23 | Antimalarial compound dihydroartemisinin |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN1135974C (en) |
| AU (1) | AU2001289506A1 (en) |
| WO (1) | WO2002026226A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7842719B2 (en) | 2002-10-31 | 2010-11-30 | Kemin Foods, L.C. | Use of endoperoxides for the treatment of infections caused by flaviviridae, including hepatitis C, bovine viral diarrhea and classical swine fever virus |
| CN1255106C (en) * | 2003-09-26 | 2006-05-10 | 李国桥 | Complex artemisia apiacea extract |
| CN1833644B (en) * | 2005-03-18 | 2010-07-21 | 中国人民解放军第三军医大学 | Application of artemisinin and its derivatives dihydroartemisinin, artemether, artether and artesunate in pharmaceuticals |
| WO2007132438A2 (en) * | 2006-05-17 | 2007-11-22 | Ranbaxy Laboratories Limited | Antimalarial therapy using a combination of synthetic artemisinin derivative and bisquinoline derivative |
| CN107929240A (en) * | 2017-12-13 | 2018-04-20 | 桂林南药股份有限公司 | Piperaquine phosphate oral liquid and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5219865A (en) * | 1987-05-08 | 1993-06-15 | Hoechst Aktiengesellschaft | Pharmaceutical combination for the prophylaxis and therapy of malaria |
| CN1081035C (en) * | 1997-11-18 | 2002-03-20 | 广州市健桥医药科技发展有限公司 | Antimalarial compound naphtholquine |
| CN1092048C (en) * | 1998-06-02 | 2002-10-09 | 广州市健桥医药科技发展有限公司 | Compound piperaquine tablet |
-
2000
- 2000-08-23 CN CNB001131346A patent/CN1135974C/en not_active Ceased
-
2001
- 2001-05-31 AU AU2001289506A patent/AU2001289506A1/en not_active Abandoned
- 2001-05-31 WO PCT/CN2001/000884 patent/WO2002026226A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN1305810A (en) | 2001-08-01 |
| AU2001289506A1 (en) | 2002-04-08 |
| WO2002026226A1 (en) | 2002-04-04 |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
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| DD01 | Delivery of document by public notice |
Addressee: Cheng Wanlian Document name: Notice of acceptance of the petition for invalidation Addressee: Cheng Wanlian Document name: Request for invalidation is deemed not to have been made |
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Granted publication date: 20040128 Termination date: 20100823 |
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