AP311A - HIV-Inhibiting benzeneacetamide derivatives. - Google Patents
HIV-Inhibiting benzeneacetamide derivatives. Download PDFInfo
- Publication number
- AP311A AP311A APAP/P/1991/000288A AP9100288A AP311A AP 311 A AP311 A AP 311A AP 9100288 A AP9100288 A AP 9100288A AP 311 A AP311 A AP 311A
- Authority
- AP
- ARIPO
- Prior art keywords
- hydrogen
- formula
- halo
- parts
- nitro
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 45
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
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- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 150000003839 salts Chemical group 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000590 phytopharmaceutical Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/44—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP90201857 | 1990-07-10 | ||
| EP91200646 | 1991-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9100288A0 AP9100288A0 (en) | 1991-07-31 |
| AP311A true AP311A (en) | 1994-02-01 |
Family
ID=26125946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1991/000288A AP311A (en) | 1990-07-10 | 1991-06-26 | HIV-Inhibiting benzeneacetamide derivatives. |
Country Status (42)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI943120L (fi) * | 1991-12-30 | 1994-06-29 | Janssen Pharmaceutica Nv | Alfa-substituoituja bentseenimetanamiinijohdannaisia |
| US6177435B1 (en) | 1992-05-13 | 2001-01-23 | Glaxo Wellcome Inc. | Therapeutic combinations |
| ATE141254T1 (de) * | 1992-07-06 | 1996-08-15 | American Cyanamid Co | O-nitrophenyl cyclopropyl keton, herbizides zwischenprodukt und verfahren zu seiner herstellung |
| WO1994018963A1 (en) * | 1993-02-22 | 1994-09-01 | Janssen Pharmaceutica N.V. | Method of reversing resistance of hiv-1 strains to zidovudine |
| US5767310A (en) * | 1993-03-19 | 1998-06-16 | Merck & Co., Inc. | Phenoxyphenylacetic acid derivatives |
| US5686478A (en) * | 1993-07-20 | 1997-11-11 | Merck & Co. Inc. | Endothelin antagonists |
| GB9403449D0 (en) * | 1994-02-23 | 1994-04-13 | Wellcome Found | Therapeutic benzonitriles |
| GB9403408D0 (en) * | 1994-02-23 | 1994-04-13 | Wellcome Found | Therapeutic benzonitriles |
| IL112739A0 (en) * | 1994-02-23 | 1995-05-26 | Wellcome Found | Ayrlthiobenzonitrile compounds, their preparation and pharmaceutical compositions containing them |
| US5538991A (en) * | 1994-09-14 | 1996-07-23 | Merck & Co., Inc. | Endothelin antagonists bearing 5-membered heterocyclic amides |
| US5559135A (en) * | 1994-09-14 | 1996-09-24 | Merck & Co., Inc. | Endothelin antagonists bearing pyridyl amides |
| EP0872233A1 (en) * | 1997-04-14 | 1998-10-21 | Janssen Pharmaceutica N.V. | Antiretroviral compositions with improved bioavailability |
| RU2220950C2 (ru) * | 1997-08-22 | 2004-01-10 | Ф.Хоффманн-Ля Рош Аг | N-алканоилфенилаланиновые производные |
| DE69932820D1 (de) * | 1998-06-19 | 2006-09-28 | Us Health | Thiolester und ihre anwendungen |
| ES2258018T3 (es) | 1999-09-24 | 2006-08-16 | Janssen Pharmaceutica N.V. | Dispersiones solidas antivirales. |
| AU2001277752A1 (en) | 2000-08-11 | 2002-02-25 | Japan Tobacco Inc. | Calcium receptor antagonists |
| US7625949B2 (en) | 2004-04-23 | 2009-12-01 | Roche Palo Alto Llc | Methods for treating retroviral infections |
| AU2005235692B2 (en) * | 2004-04-23 | 2011-11-10 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| CN101500993A (zh) * | 2006-06-08 | 2009-08-05 | 百时美施贵宝公司 | 作为凝血因子Ⅶa抑制剂用作抗凝血药的2-氨基羰基苯基氨基-2-苯基乙酰胺 |
| RU2449985C2 (ru) * | 2010-03-31 | 2012-05-10 | Федеральное государственное унитарное предприятие "Российский научный центр "Прикладная химия" | Способ получения n,n-диметилацетамида |
| CN102675212B (zh) * | 2012-05-09 | 2014-11-05 | 昆明理工大学 | N-取代苯基-2-((1h-苯并咪唑-2-基)巯基)乙酰胺类衍生物及其用途 |
| CN104000807B (zh) * | 2014-05-28 | 2016-05-18 | 中山大学 | 苯基-酰胺类化合物在制备抗hiv-1病毒药物中的应用 |
| CN105367437B (zh) * | 2015-10-12 | 2017-08-01 | 湖北文理学院 | 一种2‑芳氨基乙酰胺类化合物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1423430A (en) * | 1973-03-29 | 1976-02-04 | Wyeth John & Brother Ltd | Thioamides |
| US4246429A (en) * | 1978-06-23 | 1981-01-20 | Janssen Pharmaceutica, N.V. | Novel α-amino-phenylacetic acid derivatives |
| CH637828A5 (en) * | 1978-11-15 | 1983-08-31 | Koehler Franz Dr Chemie Kg | Cytostatics |
| FI943120L (fi) * | 1991-12-30 | 1994-06-29 | Janssen Pharmaceutica Nv | Alfa-substituoituja bentseenimetanamiinijohdannaisia |
-
1991
- 1991-06-25 IE IE220891A patent/IE75693B1/en not_active IP Right Cessation
- 1991-06-26 AP APAP/P/1991/000288A patent/AP311A/en active
- 1991-06-27 NZ NZ238763A patent/NZ238763A/xx unknown
- 1991-07-02 MY MYPI91001206A patent/MY108580A/en unknown
- 1991-07-02 PH PH42728A patent/PH30977A/en unknown
- 1991-07-04 AU AU82120/91A patent/AU643056B2/en not_active Ceased
- 1991-07-04 CA CA002084508A patent/CA2084508A1/en not_active Abandoned
- 1991-07-04 DE DE69122963T patent/DE69122963T2/de not_active Expired - Fee Related
- 1991-07-04 AT AT91912334T patent/ATE144765T1/de not_active IP Right Cessation
- 1991-07-04 PL PL91297608A patent/PL167076B1/pl unknown
- 1991-07-04 WO PCT/EP1991/001254 patent/WO1992000952A1/en active IP Right Grant
- 1991-07-04 DK DK91912334.9T patent/DK0538301T3/da active
- 1991-07-04 SG SG1996002190A patent/SG48829A1/en unknown
- 1991-07-04 JP JP3511631A patent/JPH0819068B2/ja not_active Expired - Fee Related
- 1991-07-04 ES ES91912334T patent/ES2095942T3/es not_active Expired - Lifetime
- 1991-07-04 RU RU9192016592A patent/RU2087465C1/ru active
- 1991-07-04 HU HU9332A patent/HUT64013A/hu unknown
- 1991-07-04 RO RO93-00015A patent/RO112855B1/ro unknown
- 1991-07-04 KR KR1019930700032A patent/KR0183446B1/ko not_active Expired - Fee Related
- 1991-07-04 EP EP91912334A patent/EP0538301B1/en not_active Expired - Lifetime
- 1991-07-05 MX MX9100100A patent/MX9100100A/es not_active IP Right Cessation
- 1991-07-08 SI SI9111204A patent/SI9111204A/sl unknown
- 1991-07-08 IL IL11192491A patent/IL111924A/en not_active IP Right Cessation
- 1991-07-08 MA MA22481A patent/MA22208A1/fr unknown
- 1991-07-08 SK SK2102-91A patent/SK279639B6/sk unknown
- 1991-07-08 IL IL9875691A patent/IL98756A/en active IP Right Grant
- 1991-07-08 CZ CS912102A patent/CZ279901B6/cs not_active IP Right Cessation
- 1991-07-08 YU YU120491A patent/YU120491A/sh unknown
- 1991-07-09 DZ DZ910091A patent/DZ1514A1/fr active
- 1991-07-09 ZA ZA915334A patent/ZA915334B/xx unknown
- 1991-07-09 PT PT98259A patent/PT98259B/pt not_active IP Right Cessation
- 1991-07-10 CN CN91105305A patent/CN1028990C/zh not_active Expired - Fee Related
- 1991-07-10 TN TNTNSN91056A patent/TNSN91056A1/fr unknown
- 1991-08-09 TW TW080106282A patent/TW204337B/zh active
-
1992
- 1992-11-27 LV LVP-92-231A patent/LV10086B/en unknown
-
1993
- 1993-01-06 BG BG97265A patent/BG61809B1/bg unknown
- 1993-01-07 NO NO930047A patent/NO303777B1/no not_active IP Right Cessation
- 1993-01-08 OA OA60329A patent/OA09770A/fr unknown
- 1993-01-08 FI FI930070A patent/FI930070A0/fi unknown
- 1993-03-23 HR HR930485A patent/HRP930485A2/xx not_active Application Discontinuation
- 1993-08-10 LT LTIP848A patent/LT3602B/lt not_active IP Right Cessation
-
1994
- 1994-10-25 CN CN94117208A patent/CN1033142C/zh not_active Expired - Fee Related
- 1994-12-07 IL IL11192494A patent/IL111924A0/xx unknown
-
1995
- 1995-03-27 US US08/411,118 patent/US5684049A/en not_active Expired - Fee Related
- 1995-03-27 US US08/411,039 patent/US5556886A/en not_active Expired - Fee Related
- 1995-06-29 HU HU95P/P00536P patent/HU211873A9/hu unknown
-
1996
- 1996-11-28 GR GR960403220T patent/GR3021829T3/el unknown
Non-Patent Citations (2)
| Title |
|---|
| Pharmazie 38, H7, 1983 pp 449-452 * |
| Pharmazie 38, H7, 1983 pp 456-459 * |
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