KR830006217A - 9-아미노-1-하이드록시옥타하이드로벤조[c] 퀴놀린의 제조방법 - Google Patents
9-아미노-1-하이드록시옥타하이드로벤조[c] 퀴놀린의 제조방법 Download PDFInfo
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- KR830006217A KR830006217A KR1019810002717A KR810002717A KR830006217A KR 830006217 A KR830006217 A KR 830006217A KR 1019810002717 A KR1019810002717 A KR 1019810002717A KR 810002717 A KR810002717 A KR 810002717A KR 830006217 A KR830006217 A KR 830006217A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- hydrogen
- formula
- alkyl
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- HNHKDLPYCCYYJX-UHFFFAOYSA-N 9-amino-1,2,3,4,4a,5,6,6a-octahydrophenanthridin-1-ol Chemical compound OC1CCCC2NCC(C=CC(N)=C3)C3=C21 HNHKDLPYCCYYJX-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 150000002923 oximes Chemical class 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- -1 pyrrolo Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000002779 inactivation Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- (a) 구조식(Ⅱ)의 화합물을 암모니아 또는 암모니아의 산부가염 및 환원제와 반응 불활성용매 존재하에 반응시켜 R이 수소인 구조식(Ⅰ)의 화합물을 제조하고, R이 COR7또는 SO2R8인 구조식(Ⅰ) 화합물을 목적으로 하는 경우에는 이를 구조식 R7CORa(Ra는 OH, 탄소원자 1 내지 4개의 알콕시, C1 또는 Br) 또는 (R7CO)2O의 화합물로 아실화하거나 구조식 R8CO2Rb(Rb는 OH, C1 또는 Br)의 화합물로 설폰화시키며, (b) 구조식(Ⅱ)의 화합물을 포름산과 암모늄 포르메이트 또는 그의 산부가염과 반응시킨후 옥심을 반응 불활성 용매 존재하에 촉매적 수소화시킴으로써 R이 수소인 구조식(Ⅰ)의 화합물을 제조하고 경우에 따라 상기와 같이 아실화 또는 설포닐화시키며 (d) Z가 후에 정의되는 알킬렌 또는 -(alk1)m-O-(alk2)n-이며, R4가 베타-치환제인 구조식(Ⅱ)의 에논을 하이드록실아민 또는 그의 산부가염과 용매, 바람직하게는 피리딘 존재하에 반응시켜 구조식(Ⅳ)의 옥심 중간물질을 제조하고 이 옥심 중간물질을 팔라륨, 바람직하게는 팔라륨/탄소 촉매 존재하에 수소화시키며, 경우에 따라 상기와 같이 아실화 또는 설포닐화시켜 구조식(IA)의 6a, 10a,-트랜스-9-베타-아미노 화합물을 제조함을 특징으로하는 구조식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.상기 구조식중 R은 수소, CO2R8이며 이때 R7은 수소, 탄소원자 1 내지 5개의 알킬, 각기 탄소원자 2 내지 6개의 알케닐 및 알키닐, 트리플루오로메틸, 벤질, 푸릴, 티에닐, 피리딜 또는 R9C6H4이며 이중 R9은 H, NH2, F, CI, Br, CH3또는 OCH3이고 R8는 탄소원자 1 내지 5개의 알킬 또는 R9C6H4이며 특히 바람직한 R7은 탄소원자 1 내지 5개의 알킬 및 트리플루오로메틸이다.R1은 수소, 벤질, 벤조일, 탄소원자 1 내지 5개의 알킬노일 또는 -CO-(CH2)P-NR2R3이고 이때 P는 0 또는 1 내지 4의 정수이고, R2및 R3는 각기 독립적으로 수소 또는 탄소원자 1 내지 4의 알킬이고, R2및 R3가 이들이 부탁되어 있는 질소와 함께 피페리디노, 피롤로, 피롤리디노, 모르폴리노 또는 알킬그룹이 탄소원자 1 내지 4인 N-알킬피페라지노중에서 선택되는 5- 또는 6-원 헤레로사이클환을 형성한다. 바람직한 R1은 수소 및 탄소원자 1 내지 6개의 알킬이다.R5는 수소, 메틸 또는 에틸이고 특히 바람직한 R5는 수소 및 메틸이다.R6는 수소, 알콕시그룹이 탄소원자 1 내지 4인 -(CH2)y- 카르알콕시이며, 이때 Y는 0 또는 1 내지 4의 정수, 카보벤질옥시, 포르밀, 탄소원자 2 내지 5개의 알카노일, 탄소원자 1 내지 6개의 알킬, -(CH2)Z-C6H5, 이때 X는 1 내지 4의 정수, 또는 COCCH2)X-1-C6H5이고, 특히 바람직한 R6는 수소 및 탄소원자 1 내지 6개의 알킬이다.Z는 (a) 탄소원자 1 내지 9의 알킬렌, (b) -(alk1)m-X-(al2)n-이때 (alk1)과 (alk2)는 각기 탄소원자 1 내지 9의 알릴켄이고 단, (alk1)과 (alk2) 중의 탄소원자의 합계가 9 이상은 아니며, m과 n은 각기 0 또는 1이고, X는 O, S, SO 및 SO2이며 특히 바람직한 X는 0이다.W는 수소, 메틸, 피리딜, 피페리딜,이때 W1은 수소, 플루오로 및 클로로로 구성되는 그룹중에서 선택됨 및이때 W2는 수소 또는이고 a는 1 내지 5의 정수이며 b는 0 또는 1 내지 5의 정수이고, 단, a와 b의 합은 5를 넘지 않으며 특히 바람직한 w는 수소 및 페닐이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/173,207 US4309545A (en) | 1980-07-28 | 1980-07-28 | Oximino-1-hydroxyoctahydrobenzo[c]quinolines and derivatives thereof |
| US173,207 | 1980-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830006217A true KR830006217A (ko) | 1983-09-20 |
| KR850000273B1 KR850000273B1 (ko) | 1985-03-15 |
Family
ID=22630983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810002717A KR850000273B1 (ko) | 1980-07-28 | 1981-07-27 | 9-아미노-1-하이드록 시옥타하이드로 벤조[c] 퀴놀린의 제조 방법 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4309545A (ko) |
| EP (1) | EP0045171B1 (ko) |
| JP (1) | JPS57112372A (ko) |
| KR (1) | KR850000273B1 (ko) |
| AR (1) | AR230988A1 (ko) |
| AT (1) | ATE11775T1 (ko) |
| AU (1) | AU525944B2 (ko) |
| CA (1) | CA1178274A (ko) |
| CS (1) | CS228515B2 (ko) |
| DD (1) | DD202012A5 (ko) |
| DE (1) | DE3168891D1 (ko) |
| DK (1) | DK334581A (ko) |
| EG (1) | EG15535A (ko) |
| ES (1) | ES504323A0 (ko) |
| FI (1) | FI812338L (ko) |
| GR (1) | GR75283B (ko) |
| GT (1) | GT198170557A (ko) |
| HU (1) | HU185133B (ko) |
| IE (1) | IE51426B1 (ko) |
| IL (1) | IL63423A0 (ko) |
| IN (1) | IN158867B (ko) |
| NO (2) | NO812557L (ko) |
| NZ (1) | NZ197856A (ko) |
| PH (1) | PH17281A (ko) |
| PL (1) | PL133928B1 (ko) |
| PT (1) | PT73440B (ko) |
| SU (1) | SU1217254A3 (ko) |
| YU (1) | YU185181A (ko) |
| ZA (1) | ZA815128B (ko) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920221A (en) * | 1982-03-16 | 1990-04-24 | Pfizer Inc. | Substituted decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines |
| US4642373A (en) * | 1982-03-16 | 1987-02-10 | Pfizer Inc. | Substituted dodecahydrotripheylenes, and decahydropyrrolo[1,2-f]phenanthridines as CNS agents |
| US4473704A (en) * | 1982-03-16 | 1984-09-25 | Pfizer Inc. | Substituted dodecahydrotriphenylenes, decahydro-1H-cyclopenta[1]phenanthrenes, decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines as CNS agents |
| US5605906A (en) * | 1995-03-24 | 1997-02-25 | Merck Frosst Canada, Inc. | Cannabinoid receptor agonists |
| SI0882021T1 (en) * | 1996-01-31 | 2003-10-31 | Altana Pharma Ag | New phenanthridines |
| SI0889886T1 (en) * | 1996-03-26 | 2003-02-28 | Altana Pharma Ag | Novel phenanthridines substituted in the 6 position |
| US6127378A (en) * | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| US5776482A (en) * | 1996-03-29 | 1998-07-07 | University Of Iowa Research Foundation | Tetrahydroquinoline analogues for use in glaucoma treatment |
| IL133825A (en) * | 1997-07-25 | 2005-12-18 | Altana Pharma Ag | Substituted 6-phenylphenanthridines, medicaments containing same and use thereof in the production of medicaments |
| WO1999005112A1 (en) * | 1997-07-25 | 1999-02-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted 6-alkylphenanthridines |
| US6566560B2 (en) | 1999-03-22 | 2003-05-20 | Immugen Pharmaceuticals, Inc. | Resorcinolic compounds |
| US6274635B1 (en) | 1999-03-22 | 2001-08-14 | Immugen Pharmaceuticals Inc. | Alkylated resorcinol derivatives for the treatment of immune diseases |
| US20060084021A1 (en) * | 2004-09-10 | 2006-04-20 | Kubicek Chris A | Wick holder |
| AU2001296402A1 (en) * | 2000-09-28 | 2002-04-08 | Immugen Pharmaceuticals, Inc. | Methods and compounds for inhibiting eicosanoid metabolism and platelet aggregation |
| AU2002213429A1 (en) * | 2000-09-28 | 2002-04-08 | Immugen Pharmaceuticals, Inc. | Antiviral methods and compounds |
| AU2003214226A1 (en) * | 2002-03-18 | 2003-10-08 | Immugen Pharmaceuticals, Inc. | Topical formulations of resorcinols and cannibinoids and methods of use |
| WO2005115375A1 (en) * | 2004-05-25 | 2005-12-08 | Othera Pharmaceuticals, Inc. | Oculoselective drugs and prodrugs |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839441A (en) * | 1969-10-27 | 1974-10-01 | Hoffmann La Roche | Intermediates for partially hydrogenated phenanthridines |
| US3878219A (en) * | 1973-07-13 | 1975-04-15 | Abbott Lab | 5H-{8 1{9 benzopyrano{8 3,4-d{9 pyridines |
| US3928598A (en) * | 1973-11-05 | 1975-12-23 | Lilly Co Eli | Hexahydro-dibenzo{8 b,d{9 pyran-9-ones as an anti-anxiety drug |
| US4087545A (en) * | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as antiemetic drugs |
| HU180917B (hu) | 1976-05-17 | 1983-05-30 | Pfizer | Eljárás 5, 6, 6a, 7-tetrahidro-benzo [c] kinolin-9(8H)-on-származékok előállítására |
| SE7704749L (sv) * | 1976-05-17 | 1977-12-05 | Pfizer | Kinoliner och forfarande och mellanprodukter for framstellning derav |
| US4152450A (en) * | 1978-02-17 | 1979-05-01 | Eli Lilly And Company | 9-Amino-dibenzopyrans |
-
1980
- 1980-07-28 US US06/173,207 patent/US4309545A/en not_active Expired - Lifetime
-
1981
- 1981-07-03 IN IN429/DEL/81A patent/IN158867B/en unknown
- 1981-07-21 AT AT81303339T patent/ATE11775T1/de not_active IP Right Cessation
- 1981-07-21 GT GT198170557A patent/GT198170557A/es unknown
- 1981-07-21 DE DE8181303339T patent/DE3168891D1/de not_active Expired
- 1981-07-21 EP EP81303339A patent/EP0045171B1/en not_active Expired
- 1981-07-22 SU SU813317052A patent/SU1217254A3/ru active
- 1981-07-22 HU HU812141A patent/HU185133B/hu not_active IP Right Cessation
- 1981-07-23 CS CS815647A patent/CS228515B2/cs unknown
- 1981-07-23 PL PL1981232331A patent/PL133928B1/pl unknown
- 1981-07-24 AR AR286204A patent/AR230988A1/es active
- 1981-07-24 IE IE1686/81A patent/IE51426B1/en unknown
- 1981-07-24 DD DD81232067A patent/DD202012A5/de unknown
- 1981-07-24 CA CA000382558A patent/CA1178274A/en not_active Expired
- 1981-07-24 GR GR65624A patent/GR75283B/el unknown
- 1981-07-27 DK DK334581A patent/DK334581A/da not_active Application Discontinuation
- 1981-07-27 AU AU73434/81A patent/AU525944B2/en not_active Ceased
- 1981-07-27 PH PH25968A patent/PH17281A/en unknown
- 1981-07-27 ZA ZA815128A patent/ZA815128B/xx unknown
- 1981-07-27 FI FI812338A patent/FI812338L/fi not_active Application Discontinuation
- 1981-07-27 NZ NZ197856A patent/NZ197856A/en unknown
- 1981-07-27 EG EG431/81A patent/EG15535A/xx active
- 1981-07-27 KR KR1019810002717A patent/KR850000273B1/ko active
- 1981-07-27 NO NO812557A patent/NO812557L/no unknown
- 1981-07-27 JP JP56117571A patent/JPS57112372A/ja active Pending
- 1981-07-27 ES ES504323A patent/ES504323A0/es active Granted
- 1981-07-27 IL IL63423A patent/IL63423A0/xx unknown
- 1981-07-27 YU YU01851/81A patent/YU185181A/xx unknown
- 1981-07-28 PT PT73440A patent/PT73440B/pt not_active IP Right Cessation
-
1985
- 1985-11-08 NO NO854454A patent/NO854454L/no unknown
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