KR920021492A - 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세트산 및 그것의 생물학적 전구체 화합물 - Google Patents
4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세트산 및 그것의 생물학적 전구체 화합물 Download PDFInfo
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- KR920021492A KR920021492A KR1019920008405A KR920008405A KR920021492A KR 920021492 A KR920021492 A KR 920021492A KR 1019920008405 A KR1019920008405 A KR 1019920008405A KR 920008405 A KR920008405 A KR 920008405A KR 920021492 A KR920021492 A KR 920021492A
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- ethoxy
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- 150000001875 compounds Chemical class 0.000 title claims 28
- 239000002243 precursor Substances 0.000 title claims 10
- SRBPKVWITYPHQR-UHFFFAOYSA-N 2-[4-[2-[(2-hydroxy-2-phenylethyl)azaniumyl]ethoxy]phenyl]acetate Chemical compound C=1C=CC=CC=1C(O)CNCCOC1=CC=C(CC(O)=O)C=C1 SRBPKVWITYPHQR-UHFFFAOYSA-N 0.000 title claims 6
- 150000003839 salts Chemical class 0.000 claims 11
- -1 4- [2- (2-hydroxy-2-phenylethylamino) ethoxy] phenyl Chemical group 0.000 claims 2
- SRBPKVWITYPHQR-KRWDZBQOSA-N 2-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]acetic acid Chemical compound C([C@H](O)C=1C=CC=CC=1)NCCOC1=CC=C(CC(O)=O)C=C1 SRBPKVWITYPHQR-KRWDZBQOSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 230000035800 maturation Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229940049953 phenylacetate Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
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- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
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- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
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Abstract
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Description
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Claims (14)
- 하기 구조식(Ⅰ)의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염:
- 제1항에 있어서, 상기 화합물의 카르복실산 형태이거나 그것의 약학적 허용염인 것을 특징으로 하는 화합물.
- 제2항에 있어서, 상기 화합물이 염산염으로 형성된 염 형태인 것을 특징으로 하는 화합물.
- 제1항에 있어서, 하기 구조식(Ⅱ)의 화합물 또는 그것의 약학적 허용염인 것을 특징으로 하는 화합물:상기식에서 R4는 C1-6알콕시이다.
- 제4항에 있어서, R4가 메톡시인 것을 특징으로 하는 화합물.
- 제1항에있어서, (R)-4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐아세트산, (R)-4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐아세트아미드, (R)-메틸-4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐아세테이트, 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐아세트산, 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세트 아미드, 또는 메틸 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세테이트나 그것의 약학적 허용염인 것을 특징으로 하는 화합물.
- 제1항의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염 및 약학적 허용 담체를 포함하는 약학적 조성물.
- 제1항의 화합물을 제조하기 위한 방법으로서, (a) 하기 구조식(Ⅲ) 또는 (Ⅳ)의 화합물과 하기 구조식(Ⅴ)의 화합물을 반응시키거나, (b) 하기 구조식(Ⅵ)의 화합물을 가수분해 하거나, (c) 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세트산의 경우 하기 구조식(Ⅶ)의 화합물을 가수분해하거나, (d) 하기 구조식(Ⅷ)의 화합물을 하기 구조식(IX)의 화합물과 반응시키거나, (e) 하기 구조식(X)의 화합물의 보호기를 제거하거나, (f) 4-[2-(2-히드록시-2-페닐 에틸 아미노)에톡시]페닐 아세트산을 생물학적 전구체로 전환시키거나, 역으로, 4-[2-(2-히드록시-2-페닐 에틸 아미노)에톡시]페닐 아세트산의 생물학적 전구체를 4-[2-(2-히드록시-2-페닐 에틸 아미노)에톡시]페닐 아세트산의 또다른 생물학적 전구체로 전환시키거나, (g) 하기 구조식(XI)의 화합물을 환원시키거나, (h) 하기 구조식(XII)의 화합물을 환원시키거나, (i) 하기 구조식(XIII)의 화합물을 환원시키며, 여기에서 임의의 작용기를 선택적으로 보호하고 그후 필요하다면 (ⅰ) 임의의 작용기를 제거하고, (ⅱ) 약학적 허용염을 형성하는 것을 포함하는 방법:상기식에서,-COR4는 카르복시 또는 그겻의 생물학적 전구체이며, L와 L'은 이탈기이고, R5는 가수분해성기이며, R6는 -COR4기의 보호된 유도체이다.
- 제8항에서 규정 구조식(Ⅵ), (Ⅹ), (XI), (XII) 또는 (XIII)의 화합물.
- 하기 구조식의 화합물;
- 제1항의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염을 β3-아드레날린성 수용체를 통해 매개되는 질병을 치료하기 위해 사용하는 방법.
- 제1항의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염을 발열촉진 및/또는 글루코오즈 내성을 향상시키는데 사용하는 방법.
- 제1항의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염을 비만증, 성숙기 개시 당뇨병, NIDDM, 고혈압 및/또는 과유지질혈증을 치료하는데 사용하는 방법.
- 제1항의 화합물 또는 그것의 생물학적 전구체 또는 그것의 약학적 허용염을 과트리글리세라이드 혈증, 콜레스테롤과잉 혈증, 아테롬성 동맥경화증 및 HDL 저레벨증을 치료하는데 사용하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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Application Number | Priority Date | Filing Date | Title |
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GB919111426A GB9111426D0 (en) | 1991-05-28 | 1991-05-28 | Chemical compounds |
GB9111426.4 | 1991-05-28 |
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KR920021492A true KR920021492A (ko) | 1992-12-18 |
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KR1019920008405A KR920021492A (ko) | 1991-05-28 | 1992-05-19 | 4-[2-(2-히드록시-2-페닐에틸아미노)에톡시]페닐 아세트산 및 그것의 생물학적 전구체 화합물 |
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US (3) | US5393779A (ko) |
EP (1) | EP0516349B1 (ko) |
JP (1) | JP3232337B2 (ko) |
KR (1) | KR920021492A (ko) |
CN (1) | CN1031564C (ko) |
AP (1) | AP301A (ko) |
AT (1) | ATE128115T1 (ko) |
AU (1) | AU652826B2 (ko) |
BG (1) | BG96392A (ko) |
BR (1) | BR9202002A (ko) |
CA (1) | CA2068377A1 (ko) |
CS (1) | CS159292A3 (ko) |
DE (1) | DE69204906T2 (ko) |
DK (1) | DK0516349T3 (ko) |
ES (1) | ES2076688T3 (ko) |
FI (1) | FI922424A (ko) |
GB (2) | GB9111426D0 (ko) |
GR (1) | GR3017462T3 (ko) |
HU (2) | HU211401B (ko) |
IE (1) | IE69043B1 (ko) |
IL (1) | IL101821A0 (ko) |
MY (1) | MY136249A (ko) |
NO (1) | NO922113L (ko) |
NZ (1) | NZ242643A (ko) |
OA (1) | OA10077A (ko) |
PL (1) | PL294704A1 (ko) |
RO (1) | RO111569B1 (ko) |
RU (1) | RU2073666C1 (ko) |
SI (1) | SI9200093A (ko) |
TW (1) | TW198709B (ko) |
YU (1) | YU54592A (ko) |
ZA (1) | ZA923356B (ko) |
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US5662934A (en) * | 1993-01-05 | 1997-09-02 | Najarian; Thomas | Compositions and methods for lowering cholesterol while maintaining antioxidant levels |
GB9313574D0 (en) * | 1993-07-01 | 1993-08-18 | Glaxo Group Ltd | Medicaments |
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US5563171A (en) * | 1993-11-05 | 1996-10-08 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3-adrenergic agonists |
US5578638A (en) * | 1993-11-05 | 1996-11-26 | American Cyanamid Company | Treatment of glaucoma and ocular hypertension with β3 -adrenergic agonists |
US5541197A (en) * | 1994-04-26 | 1996-07-30 | Merck & Co., Inc. | Substituted sulfonamides as selective β3 agonists for the treatment of diabetes and obesity |
US5561142A (en) * | 1994-04-26 | 1996-10-01 | Merck & Co., Inc. | Substituted sulfonamides as selective β3 agonists for the treatment of diabetes and obesity |
US5627200A (en) * | 1994-09-26 | 1997-05-06 | Pfizer Inc | β3 -Adrenoceptor agonists and antagonists for the treatment of intestinal motility disorders, depression, prostate disease and dyslipidemia |
US6090836A (en) * | 1996-02-02 | 2000-07-18 | Merck & Co., Inc. | Benzisoxazole-derived antidiabetic compounds |
US6020382A (en) * | 1996-02-02 | 2000-02-01 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
US5847008A (en) * | 1996-02-02 | 1998-12-08 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
US5859051A (en) * | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
US6090839A (en) * | 1996-12-23 | 2000-07-18 | Merck & Co., Inc. | Antidiabetic agents |
US6160000A (en) * | 1996-12-23 | 2000-12-12 | Merck & Co., Inc. | Antidiabetic agents based on aryl and heteroarylacetic acids |
ID27415A (id) | 1998-06-30 | 2001-04-05 | Takeda Chemical Industries Ltd | Komposisi farmaseutik |
CA2398199A1 (en) * | 2000-01-28 | 2001-08-02 | Asahi Kasei Kabushiki Kaisha | Novel therapeutic agents that use a .beta.3 agonist |
US6987131B1 (en) | 2000-06-26 | 2006-01-17 | Burzynski Stanislaw R | Phenylacetic acid compositions for treating or preventing hypercholesterolemia |
CA2495537C (en) | 2000-08-29 | 2010-03-30 | Nobex Corporation | Immunoregulatory compounds and derivatives and methods of treating diseases therewith |
GB0102407D0 (en) | 2001-01-31 | 2001-03-14 | Glaxo Group Ltd | Process |
US7709677B2 (en) | 2001-01-31 | 2010-05-04 | Glaxosmithkline Llc | Process of preparing arylethanoldiamines |
JP2004331500A (ja) * | 2001-02-16 | 2004-11-25 | Dainippon Pharmaceut Co Ltd | 血中濃度制御製剤 |
EP1236723A1 (en) | 2001-03-01 | 2002-09-04 | Pfizer Products Inc. | Sulfamide derivatives useful as beta3 agonists and pharmaceutical uses thereof |
US8048924B2 (en) * | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
US6864268B2 (en) | 2002-02-27 | 2005-03-08 | Pfizer Inc. | β3 adrenergic receptor agonists |
AU2003209527A1 (en) | 2002-02-27 | 2003-09-09 | Pfizer Products Inc. | Crystal forms of (r)-2-(2-(4-oxazol-4-yl-phenoxy)-ethylamino)-1-pyridin-3-yl-ethanol |
EP1478625A1 (en) * | 2002-02-27 | 2004-11-24 | Pfizer Products Inc. | Processes and intermediates useful in preparing beta-3-adrenergic receptor agonists |
DK1773767T3 (en) | 2004-07-07 | 2016-03-21 | Biocon Ltd | Synthesis of azo bound in immune regulatory relations |
TWI478712B (zh) | 2008-09-30 | 2015-04-01 | Astellas Pharma Inc | 釋控性醫藥組成物 |
US8476227B2 (en) | 2010-01-22 | 2013-07-02 | Ethicon Endo-Surgery, Inc. | Methods of activating a melanocortin-4 receptor pathway in obese subjects |
US9044606B2 (en) | 2010-01-22 | 2015-06-02 | Ethicon Endo-Surgery, Inc. | Methods and devices for activating brown adipose tissue using electrical energy |
CN102633637A (zh) * | 2012-03-30 | 2012-08-15 | 吉林大学 | 有效缓解和治疗便秘的药用配方 |
US10092738B2 (en) | 2014-12-29 | 2018-10-09 | Ethicon Llc | Methods and devices for inhibiting nerves when activating brown adipose tissue |
US10080884B2 (en) | 2014-12-29 | 2018-09-25 | Ethicon Llc | Methods and devices for activating brown adipose tissue using electrical energy |
US11766419B2 (en) * | 2021-01-08 | 2023-09-26 | Banasthali Vidyapith | Mebeverine as soluble epoxide hydrolase inhibitor |
US12097189B1 (en) | 2024-02-09 | 2024-09-24 | Astellas Pharma Inc. | Pharmaceutical composition for modified release |
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GB1245148A (en) * | 1968-11-18 | 1971-09-08 | Pfizer Ltd | Propanolamine derivatives |
GB1301134A (en) * | 1970-07-18 | 1972-12-29 | Pfizer Ltd | SUBSTITUTED 1-PHENYL-2-ALLYLAMINO-ALKANOLS, 1-PHENYL-2-ALLYLAMINO-ALKANES AND alpha-AMINOALKYLPHENYL KETONES |
EP0006735B1 (en) * | 1978-06-28 | 1983-06-15 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
DE3061205D1 (en) * | 1979-06-16 | 1983-01-05 | Beecham Group Plc | Secondary amines, their preparation and use in pharmaceutical compositions |
US4338333A (en) * | 1979-06-16 | 1982-07-06 | Beecham Group Limited | Ethanamine derivatives their preparation and use in pharmaceutical compositions |
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GB2212801A (en) * | 1987-11-26 | 1989-08-02 | Resolution Chemicals Limited | Preparation of an alkanolamine derivatives |
GB8801306D0 (en) * | 1988-01-21 | 1988-02-17 | Ici Plc | Chemical compounds |
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-
1991
- 1991-05-28 GB GB919111426A patent/GB9111426D0/en active Pending
-
1992
- 1992-05-07 NZ NZ242643A patent/NZ242643A/en unknown
- 1992-05-08 ZA ZA923356A patent/ZA923356B/xx unknown
- 1992-05-10 IL IL101821A patent/IL101821A0/xx unknown
- 1992-05-11 CA CA002068377A patent/CA2068377A1/en not_active Abandoned
- 1992-05-15 HU HU9201609A patent/HU211401B/hu not_active IP Right Cessation
- 1992-05-18 AP APAP/P/1992/000385A patent/AP301A/en active
- 1992-05-19 KR KR1019920008405A patent/KR920021492A/ko not_active Application Discontinuation
- 1992-05-20 RU SU925011728A patent/RU2073666C1/ru active
- 1992-05-21 AU AU17044/92A patent/AU652826B2/en not_active Ceased
- 1992-05-22 AT AT92304653T patent/ATE128115T1/de not_active IP Right Cessation
- 1992-05-22 DK DK92304653.6T patent/DK0516349T3/da active
- 1992-05-22 ES ES92304653T patent/ES2076688T3/es not_active Expired - Lifetime
- 1992-05-22 DE DE69204906T patent/DE69204906T2/de not_active Expired - Fee Related
- 1992-05-22 GB GB929210919A patent/GB9210919D0/en active Pending
- 1992-05-22 EP EP92304653A patent/EP0516349B1/en not_active Expired - Lifetime
- 1992-05-25 YU YU54592A patent/YU54592A/sh unknown
- 1992-05-25 MY MYPI92000893A patent/MY136249A/en unknown
- 1992-05-26 CS CS921592A patent/CS159292A3/cs unknown
- 1992-05-26 CN CN92103977A patent/CN1031564C/zh not_active Expired - Fee Related
- 1992-05-27 SI SI19929200093A patent/SI9200093A/sl unknown
- 1992-05-27 FI FI922424A patent/FI922424A/fi not_active Application Discontinuation
- 1992-05-27 PL PL29470492A patent/PL294704A1/xx unknown
- 1992-05-27 OA OA60218A patent/OA10077A/en unknown
- 1992-05-27 BR BR929202002A patent/BR9202002A/pt not_active Application Discontinuation
- 1992-05-27 NO NO92922113A patent/NO922113L/no unknown
- 1992-05-27 JP JP13484692A patent/JP3232337B2/ja not_active Expired - Fee Related
- 1992-05-28 BG BG096392A patent/BG96392A/bg unknown
- 1992-05-28 US US07/889,196 patent/US5393779A/en not_active Expired - Lifetime
- 1992-05-28 RO RO92-200738A patent/RO111569B1/ro unknown
- 1992-06-02 TW TW081104319A patent/TW198709B/zh active
- 1992-07-01 IE IE921447A patent/IE69043B1/en not_active IP Right Cessation
-
1994
- 1994-11-18 US US08/344,708 patent/US5434184A/en not_active Expired - Lifetime
-
1995
- 1995-03-06 HU HU95P/P00087P patent/HU210799A9/hu unknown
- 1995-05-10 US US08/437,988 patent/US5480910A/en not_active Expired - Lifetime
- 1995-09-21 GR GR950402415T patent/GR3017462T3/el unknown
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