ES420325A1 - Substituted 16,17,18,19,20-pentanorprostaglandins - Google Patents
Substituted 16,17,18,19,20-pentanorprostaglandinsInfo
- Publication number
- ES420325A1 ES420325A1 ES420325A ES420325A ES420325A1 ES 420325 A1 ES420325 A1 ES 420325A1 ES 420325 A ES420325 A ES 420325A ES 420325 A ES420325 A ES 420325A ES 420325 A1 ES420325 A1 ES 420325A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- phenyl
- see formula
- ligation
- substituent
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- -1 3,4-methylenedioxyphenyl Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004391 aryl sulfonyl 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 150000003180 prostaglandins 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
- 229930194542 Keto Natural products 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000006184 cosolvent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 125000003831 tetrazolyl 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
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- 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
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- 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
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (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)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A procedure to prepare a prostaglandin of structure: **(See formula)** and its epimer C15; wherein: Ar is phenyl, 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl, 3,4,5-trimethoxyphenyl; alpha- or beta-naphthyl or monosubstituted phenyl whose substituent is halo, trifluoromethyl, phenyl, lower alkyl or lower alkoxy; R is hydrogen or lower alkyl; n and m are each integers between 0 and 3, provided that the sum of n and m does not exceed 3; W is a single ligation or a double trans ligation; Z is a single ligation or a double trans ligation; M is keto, (see formula) or (see formula); X is selected from: (see formula), where R'is hydrogen, an alkyl of 1 to 10 carbon atoms; an aralkyl of 7 to 9 carbon atoms; a cycloalkyl of 3 to 8 carbon atoms; alpha- or beta-naphthyl; phenyl or monosubstituted phenyl, the substituent of which is halo, lower alkyl, lower alkoxy or phenyl; tetrazolyl; or (see formula), where R'' is an alkanoyl having from 2 to 10 carbon atoms or a cycloalkanoyl having from 4 to 8 carbon atoms; aryl or substituted arioyl having from 7 to 11 carbon atoms and in which the substituent is methyl, halogen or methoxy; an alkylsulfonyl having 1 to 7 carbon atoms; arylsulfonyl or substituted arylsulfonyl whose substituent is methyl, halogen, or methoxy; and in which: L, M and N are selected to complete the structure of a prostaglandin from series A, E or F, the lower alkanoyl, formyl or benzoyl esters of any free hydroxyl groups at positions C9-, C11 - and C15, and the pharmaceutically acceptable bases of the compounds, in which X is COOH, characterized in that said compound is prepared by treating the 11- and 15-tetrahydropyranide ethers of a compound of formula I above, with an aqueous acid at a pH of 2-5 in the presence or absence of a solubilizing co-solvent at a temperature of 25-50ºC for 2-4 hours and when required to convert the compound thus produced into the lower alkanoyl, formyl or benzoyl esters of any hydroxyl groups free at the C9-, C11- and C15 positions and the pharmaceutically acceptable salts of the compounds where X is COOH. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481372A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES420325A1 true ES420325A1 (en) | 1976-04-16 |
Family
ID=23178133
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES420325A Expired ES420325A1 (en) | 1972-11-08 | 1973-11-07 | Substituted 16,17,18,19,20-pentanorprostaglandins |
| ES433046A Expired ES433046A1 (en) | 1972-11-08 | 1974-12-18 | Substituted 16,17,18,19,20-pentanorprostaglandins |
| ES433047A Expired ES433047A1 (en) | 1972-11-08 | 1974-12-18 | Substituted 16,17,18,19,20-pentanorprostaglandins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES433046A Expired ES433046A1 (en) | 1972-11-08 | 1974-12-18 | Substituted 16,17,18,19,20-pentanorprostaglandins |
| ES433047A Expired ES433047A1 (en) | 1972-11-08 | 1974-12-18 | Substituted 16,17,18,19,20-pentanorprostaglandins |
Country Status (29)
| Country | Link |
|---|---|
| JP (3) | JPS5416491B2 (en) |
| AR (3) | AR200585A1 (en) |
| AT (3) | AT367034B (en) |
| AU (1) | AU470375B2 (en) |
| BE (1) | BE806995A (en) |
| CA (3) | CA1085831A (en) |
| CH (1) | CH597176A5 (en) |
| CS (3) | CS182794B2 (en) |
| DD (4) | DD118856A5 (en) |
| DE (1) | DE2355540C2 (en) |
| DK (1) | DK144247C (en) |
| ES (3) | ES420325A1 (en) |
| FI (1) | FI60389C (en) |
| FR (3) | FR2205335B1 (en) |
| GB (3) | GB1456512A (en) |
| HK (3) | HK27979A (en) |
| HU (3) | HU173507B (en) |
| IE (1) | IE39537B1 (en) |
| IL (1) | IL43589A (en) |
| IN (1) | IN139384B (en) |
| KE (3) | KE2930A (en) |
| MY (3) | MY7900245A (en) |
| NL (1) | NL164273C (en) |
| NO (3) | NO147836C (en) |
| PH (3) | PH13272A (en) |
| SE (4) | SE448992B (en) |
| SU (4) | SU584766A3 (en) |
| YU (3) | YU39715B (en) |
| ZA (1) | ZA738554B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929862A (en) * | 1974-01-08 | 1975-12-30 | Upjohn Co | Substituted tolylesters of PGF{HD 2{B {60 |
| GB1506816A (en) * | 1975-03-31 | 1978-04-12 | Upjohn Co | Prostaglandins |
| US3986764A (en) * | 1975-03-31 | 1976-10-19 | Gte Automatic Electric Laboratories Incorporated | Panel for supporting a pair of elongated mating connectors and selectively locking them together |
| ES449162A1 (en) * | 1975-06-23 | 1977-12-16 | Syntex Inc | 16-Phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
| GB1516414A (en) * | 1975-08-22 | 1978-07-05 | Ici Ltd | Prostane derivatives |
| SE7809008L (en) * | 1977-12-12 | 1979-06-13 | Upjohn Co | USE OF PROSTAGLAND TYPE AMIDES TO CONTROL OR REGULATE THE REPRODUCTION CYCLE IN INDIVIDUALS OF MAMMALS |
| DK523378A (en) * | 1978-01-16 | 1979-07-17 | Pfizer | PROCEDURE FOR THE PREPARATION OF N- (TETRAZOL-5-YL) PROSTAGLANDIN CARBOXAMIDES OR SALTS THEREOF |
| ID24845A (en) * | 1997-09-09 | 2000-08-24 | Procter & Gamble | AROMATIC C16-C20 SUBSTITUTED PROSTAGLANDIN PROSTAGLANDIN USED AS A FP AGONIST |
| WO2000051980A1 (en) | 1999-03-05 | 2000-09-08 | The Procter & Gamble Company | C16 unsaturated fp-selective prostaglandins analogs |
| US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| JP2002329615A (en) * | 2001-05-02 | 2002-11-15 | Ohira Denshi Kk | Toroidal coil |
| US6476064B1 (en) * | 2001-06-13 | 2002-11-05 | Allergan, Inc. | Cyclopentane heptan(ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents |
| WO2006047466A2 (en) | 2004-10-21 | 2006-05-04 | Duke University | Ophthamological drugs |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1324737A (en) * | 1970-11-02 | 1973-07-25 | Upjohn Co | Prostaglandins and the preparation thereof |
| IE37602B1 (en) * | 1971-05-11 | 1977-08-31 | Ici Ltd | Cyclopentane derivatives |
-
1972
- 1972-11-07 DD DD182498*A patent/DD118856A5/xx unknown
-
1973
- 1973-10-29 SE SE7314686A patent/SE448992B/en unknown
- 1973-11-07 FI FI3443/73A patent/FI60389C/en active
- 1973-11-07 NO NO4288/73A patent/NO147836C/en unknown
- 1973-11-07 DK DK601073A patent/DK144247C/en not_active IP Right Cessation
- 1973-11-07 IN IN2448/CAL/73A patent/IN139384B/en unknown
- 1973-11-07 DD DD174504A patent/DD109212A5/xx unknown
- 1973-11-07 BE BE1005485A patent/BE806995A/en not_active IP Right Cessation
- 1973-11-07 GB GB5175873A patent/GB1456512A/en not_active Expired
- 1973-11-07 AT AT0936973A patent/AT367034B/en not_active IP Right Cessation
- 1973-11-07 IE IE2002/73A patent/IE39537B1/en unknown
- 1973-11-07 NL NL7315263.A patent/NL164273C/en not_active IP Right Cessation
- 1973-11-07 CA CA185,274A patent/CA1085831A/en not_active Expired
- 1973-11-07 IL IL43589A patent/IL43589A/en unknown
- 1973-11-07 JP JP12527273A patent/JPS5416491B2/ja not_active Expired
- 1973-11-07 DE DE2355540A patent/DE2355540C2/en not_active Expired
- 1973-11-07 AR AR250885A patent/AR200585A1/en active
- 1973-11-07 CH CH1563973A patent/CH597176A5/xx not_active IP Right Cessation
- 1973-11-07 ZA ZA738554A patent/ZA738554B/en unknown
- 1973-11-07 PH PH15191A patent/PH13272A/en unknown
- 1973-11-07 FR FR7339544A patent/FR2205335B1/fr not_active Expired
- 1973-11-07 AU AU62247/73A patent/AU470375B2/en not_active Expired
- 1973-11-07 GB GB2395076A patent/GB1456513A/en not_active Expired
- 1973-11-07 DD DD182499*A patent/DD119411A5/xx unknown
- 1973-11-07 DD DD182497*A patent/DD117233A5/xx unknown
- 1973-11-07 ES ES420325A patent/ES420325A1/en not_active Expired
- 1973-11-07 YU YU2880/73A patent/YU39715B/en unknown
- 1973-11-07 GB GB2285876A patent/GB1456514A/en not_active Expired
- 1973-11-08 CS CS7500006066A patent/CS182794B2/en unknown
- 1973-11-08 CS CS7500006065A patent/CS182793B2/en unknown
- 1973-11-08 HU HU73PI451A patent/HU173507B/en unknown
- 1973-11-08 HU HU73PI00000452A patent/HU171819B/en unknown
- 1973-11-08 HU HU72PI00000399A patent/HU172703B/en unknown
- 1973-11-08 CS CS7300007669A patent/CS182791B2/en unknown
- 1973-11-11 SU SU7301971722A patent/SU584766A3/en active
-
1974
- 1974-06-06 AR AR254091A patent/AR199966A1/en active
- 1974-06-06 AR AR254090A patent/AR202931A1/en active
- 1974-09-26 NO NO743493A patent/NO148998C/en unknown
- 1974-12-18 ES ES433046A patent/ES433046A1/en not_active Expired
- 1974-12-18 ES ES433047A patent/ES433047A1/en not_active Expired
-
1975
- 1975-02-18 SU SU752106791A patent/SU667141A3/en active
- 1975-02-18 NO NO750535A patent/NO149139C/en unknown
- 1975-02-19 SU SU752106125A patent/SU893130A3/en active
- 1975-07-24 PH PH17410A patent/PH13110A/en unknown
- 1975-07-24 PH PH17409A patent/PH13325A/en unknown
- 1975-08-22 FR FR7526059A patent/FR2279729A1/en active Granted
- 1975-08-22 FR FR7526060A patent/FR2283146A1/en active Granted
-
1976
- 1976-07-23 AT AT544576A patent/AT360672B/en not_active IP Right Cessation
- 1976-07-23 AT AT544676A patent/AT353285B/en active
- 1976-10-15 JP JP51123738A patent/JPS5257147A/en active Pending
- 1976-10-15 JP JP51123737A patent/JPS5253841A/en active Pending
-
1977
- 1977-01-24 SE SE7700717A patent/SE436278B/en not_active IP Right Cessation
- 1977-01-24 SE SE7700718A patent/SE431756B/en not_active IP Right Cessation
- 1977-01-24 SE SE7700716A patent/SE445111B/en not_active IP Right Cessation
- 1977-07-11 CA CA341,898A patent/CA1088931A/en not_active Expired
- 1977-07-11 CA CA341,897A patent/CA1088930A/en not_active Expired
-
1978
- 1978-07-27 SU SU782629453A patent/SU745362A3/en active
-
1979
- 1979-03-15 KE KE2930A patent/KE2930A/en unknown
- 1979-03-15 KE KE2931A patent/KE2931A/en unknown
- 1979-03-15 KE KE2932A patent/KE2932A/en unknown
- 1979-05-03 HK HK279/79A patent/HK27979A/en unknown
- 1979-05-03 HK HK281/79A patent/HK28179A/en unknown
- 1979-05-03 HK HK280/79A patent/HK28079A/en unknown
- 1979-12-30 MY MY245/79A patent/MY7900245A/en unknown
- 1979-12-30 MY MY243/79A patent/MY7900243A/en unknown
- 1979-12-30 MY MY246/79A patent/MY7900246A/en unknown
-
1980
- 1980-10-23 YU YU2707/80A patent/YU36975B/en unknown
- 1980-10-23 YU YU2706/80A patent/YU37316B/en unknown
Also Published As
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