ES416865A1 - 15-substituted-omega-pentanorprostaglandins - Google Patents
15-substituted-omega-pentanorprostaglandinsInfo
- Publication number
- ES416865A1 ES416865A1 ES416865A ES416865A ES416865A1 ES 416865 A1 ES416865 A1 ES 416865A1 ES 416865 A ES416865 A ES 416865A ES 416865 A ES416865 A ES 416865A ES 416865 A1 ES416865 A1 ES 416865A1
- Authority
- ES
- Spain
- Prior art keywords
- alpha
- compound
- represent
- indicated above
- hydrogen
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 229930194542 Keto Natural products 0.000 abstract 3
- -1 beta-naphthyl Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000000468 ketone group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B2211/00—Applications
- B63B2211/02—Oceanography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
A process for preparing ω -pentanorprostaglandins substituted at position 15 having the following structure: **(See formula)** in which: Ar is alpha- or beta-furyl; alpha- or beta-thienyl; alpha- or beta-naphthyl; phenyl; 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl; 3,4,5-trimethoxyphenyl or monosubstituted phenyl in which the substituent is halo, trifluoromethyl, phenyl, lower alkyl or lower alkoxy; n is an integer from 0 to 5, provided that when Ar is phenyl, substituted phenyl, or naphthyl, n is 0 or 1; R is hydrogen or lower alkyl; W is a single tie or a double cis tie; Z is a single or double trans ligature when n is an integer from 1 to 5, and Z is a single ligature when n is zero; M is keto, (see formula); N and L together form a single bond or N is alpha-hydroxyl when L is hydrogen and in which: L, M, and N are selected to complete the structure of a series A, E, or F prostaglandin, the lower alkanoyl, formyl, or benzoyl esters of any free hydroxyl groups at positions C9-, C11, and C15 and their salts pharmaceutically acceptable, characterized by the fact that: a) when N is alpha-hydroxy and L is hydrogen and Ar, n, M, W and Z represent what is indicated above, said compound is prepared by treating the 11-, and 11- and 15-tetrahydropyranyl ethers of a compound of formula I, with an appropriate acid; b) when N and L, together, form a single bond, M is keto and Ar, n, R, W and Z represent what is indicated above, said compound is prepared by the reaction of a compound of formula I, in the which N is alpha-hydroxy and L is hydrogen, M is keto and Ar, n, R, W and Z represent as indicated above, with an appropriate dehydration agent; c) when N is alpha-hydroxy and L is hydrogen, M is (see formula) and Ar, n, R, W and Z represent what is indicated above, said compound is prepared by the reaction of a compound of formula I, in which N is alpha-hydroxy and L is hydrogen, M is Keto, Ar, n, R, W and Z represent as indicated above with a suitable reducing agent and, if appropriate, the 9alpha- and 9beta- isomers are separated. d) when N is alpha-hydroxy, L is hydrogen, Ar, R, n and M represent what is indicated above, and W and Z are simple bonds, said compound is prepared by the catalytic reduction of a compound of formula I, in which Ar, R, n and M represent what is indicated above, W is a single ligature or a double cis ligature when Z is a double trans ligature, and Z is a single ligature when W is a cis double ligature; e) when N is alpha-hydroxy, L is hydrogen, Ar, R, n and M represent what is indicated above, W is a single ligation and Z is a trans double ligation, said compound is prepared by the selective reduction of a compound of formula I, in which Ar, R, n and M represent what is indicated above and W and Z are double bonds; and, if appropriate, 9alpha-, 11alpha-, and 15alpha-alkanoyl, formyl, or benzoyl esters of any free hydroxyl groups are prepared by the reaction of said compounds with the appropriate acylating agents and, if desired, prepared the pharmaceutically acceptable salts of these compounds. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27122072A | 1972-07-13 | 1972-07-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES416865A1 true ES416865A1 (en) | 1976-03-01 |
Family
ID=23034697
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES416865A Expired ES416865A1 (en) | 1972-07-13 | 1973-07-03 | 15-substituted-omega-pentanorprostaglandins |
ES437038A Expired ES437038A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
ES437039A Expired ES437039A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
ES437037A Expired ES437037A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES437038A Expired ES437038A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
ES437039A Expired ES437039A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
ES437037A Expired ES437037A1 (en) | 1972-07-13 | 1975-04-26 | 15-substituted-omega-pentanorprostaglandins |
Country Status (25)
Country | Link |
---|---|
JP (4) | JPS5241257B2 (en) |
AR (2) | AR209064A1 (en) |
AT (1) | AT367033B (en) |
BE (1) | BE802231A (en) |
CA (1) | CA1041495A (en) |
CH (1) | CH593254A5 (en) |
CS (1) | CS201027B2 (en) |
DD (2) | DD109210A5 (en) |
DE (1) | DE2334945A1 (en) |
ES (4) | ES416865A1 (en) |
FI (1) | FI57583C (en) |
FR (1) | FR2192834B1 (en) |
GB (1) | GB1446341A (en) |
HU (4) | HU171946B (en) |
IE (1) | IE37909B1 (en) |
IL (2) | IL42691A (en) |
IN (1) | IN138789B (en) |
LU (1) | LU68015A1 (en) |
NL (1) | NL7309792A (en) |
NO (2) | NO143741C (en) |
PH (1) | PH11461A (en) |
SE (3) | SE7705945L (en) |
SU (4) | SU644384A3 (en) |
YU (1) | YU187773A (en) |
ZA (1) | ZA734769B (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1386146A (en) * | 1972-05-03 | 1975-03-05 | Ici Ltd | Cyclopentane derivatives |
DE2463432C2 (en) * | 1974-04-03 | 1987-06-19 | Hoechst Ag, 6230 Frankfurt, De | |
DE2416193C2 (en) | 1974-04-03 | 1985-08-14 | Hoechst Ag, 6230 Frankfurt | Prostaglandin analogs, processes for their preparation and their use as cytoprotective agents |
ZA747723B (en) * | 1974-12-11 | 1976-11-24 | Pfizer | 11-desoxy-15-substituted-omega-pentanor prostaglandins |
US4149006A (en) * | 1977-01-24 | 1979-04-10 | G. D. Searle & Co. | Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain |
GB8329559D0 (en) * | 1983-11-04 | 1983-12-07 | Erba Farmitalia | Furyl derivatives of 16-substituted prostaglandins preparations |
SE9002596D0 (en) * | 1990-08-08 | 1990-08-08 | Pharmacia Ab | A METHOD OF SYNTHESIS OF PROSTAGLANDIN DERIVATIVES |
US5972991A (en) * | 1992-09-21 | 1999-10-26 | Allergan | Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
US6602900B2 (en) | 1992-09-21 | 2003-08-05 | Allergan, Inc. | Cyclopentane heptan(ENE)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
KR100578616B1 (en) * | 2004-07-23 | 2006-05-10 | 한미약품 주식회사 | Method for the preparation of d-erythro-2,2-difluoro-2-deoxy-1-oxoribose |
BR112016013594A8 (en) * | 2013-12-13 | 2020-05-19 | Allergan Inc | crystalline forms of a dihydroxy cyclopentyl alpha compound, omega-disubstituted, pharmaceutical composition, methods for preparing and using them |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1324737A (en) * | 1970-11-02 | 1973-07-25 | Upjohn Co | Prostaglandins and the preparation thereof |
GB1386146A (en) * | 1972-05-03 | 1975-03-05 | Ici Ltd | Cyclopentane derivatives |
IL42373A (en) * | 1972-06-02 | 1977-08-31 | Pfizer | Oxaprostagliandins and their preparation |
-
1973
- 1973-07-03 ES ES416865A patent/ES416865A1/en not_active Expired
- 1973-07-03 NO NO2724/73A patent/NO143741C/en unknown
- 1973-07-05 FI FI2162/73A patent/FI57583C/en active
- 1973-07-06 IN IN1575/CAL/73A patent/IN138789B/en unknown
- 1973-07-09 IL IL42691A patent/IL42691A/en unknown
- 1973-07-09 PH PH14802A patent/PH11461A/en unknown
- 1973-07-10 DE DE19732334945 patent/DE2334945A1/en not_active Withdrawn
- 1973-07-11 CS CS734994A patent/CS201027B2/en unknown
- 1973-07-12 HU HU73PI00000481A patent/HU171946B/en unknown
- 1973-07-12 DD DD172243A patent/DD109210A5/xx unknown
- 1973-07-12 CA CA176,270A patent/CA1041495A/en not_active Expired
- 1973-07-12 HU HU73PI00000480A patent/HU171158B/en unknown
- 1973-07-12 HU HU73PI00000387A patent/HU171156B/en unknown
- 1973-07-12 SU SU731948945A patent/SU644384A3/en active
- 1973-07-12 HU HU73PI00000482A patent/HU172058B/en unknown
- 1973-07-12 DD DD180811*A patent/DD116459A5/xx unknown
- 1973-07-12 CH CH1020673A patent/CH593254A5/xx not_active IP Right Cessation
- 1973-07-12 BE BE1005234A patent/BE802231A/en unknown
- 1973-07-13 FR FR7325835A patent/FR2192834B1/fr not_active Expired
- 1973-07-13 ZA ZA734769A patent/ZA734769B/en unknown
- 1973-07-13 LU LU68015A patent/LU68015A1/xx unknown
- 1973-07-13 GB GB3121773A patent/GB1446341A/en not_active Expired
- 1973-07-13 AR AR249095A patent/AR209064A1/en active
- 1973-07-13 AT AT0620773A patent/AT367033B/en not_active IP Right Cessation
- 1973-07-13 JP JP48079214A patent/JPS5241257B2/ja not_active Expired
- 1973-07-13 NL NL7309792A patent/NL7309792A/xx not_active Application Discontinuation
- 1973-07-13 IE IE1186/73A patent/IE37909B1/en unknown
- 1973-11-07 YU YU01877/73A patent/YU187773A/en unknown
-
1974
- 1974-05-06 AR AR253775A patent/AR214383A1/en active
- 1974-09-26 NO NO743492A patent/NO144830C/en unknown
-
1975
- 1975-04-26 ES ES437038A patent/ES437038A1/en not_active Expired
- 1975-04-26 ES ES437039A patent/ES437039A1/en not_active Expired
- 1975-04-26 ES ES437037A patent/ES437037A1/en not_active Expired
- 1975-09-05 SU SU752169008A patent/SU645563A3/en active
- 1975-09-09 SU SU7502170659A patent/SU584791A3/en active
- 1975-09-11 SU SU752171155A patent/SU645564A3/en active
-
1976
- 1976-08-19 IL IL50308A patent/IL50308A0/en unknown
- 1976-11-22 JP JP14060676A patent/JPS52122349A/en active Pending
- 1976-11-22 JP JP14060776A patent/JPS5293753A/en active Pending
- 1976-11-22 JP JP14060576A patent/JPS5297958A/en active Pending
-
1977
- 1977-05-20 SE SE7705945A patent/SE7705945L/en not_active Application Discontinuation
- 1977-05-20 SE SE7705947A patent/SE7705947L/en not_active Application Discontinuation
- 1977-05-20 SE SE7705946A patent/SE7705946L/en unknown
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