IE32344L - Steroids - Google Patents
SteroidsInfo
- Publication number
- IE32344L IE32344L IE680949A IE94968A IE32344L IE 32344 L IE32344 L IE 32344L IE 680949 A IE680949 A IE 680949A IE 94968 A IE94968 A IE 94968A IE 32344 L IE32344 L IE 32344L
- Authority
- IE
- Ireland
- Prior art keywords
- acetoxy
- chloro
- trione
- pregna
- diene
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000004423 acyloxy group Chemical group 0.000 abstract 4
- 239000004593 Epoxy Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000005660 chlorination reaction Methods 0.000 abstract 3
- NBIIDNCPASZGOS-UCCCNAJCSA-N (8S,9S,10R,13S,14S)-6-chloro-17-(2-hydroxyacetyl)-10,13-dimethyl-2,8,9,12,14,15-hexahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound OCC(C1=CC[C@H]2[C@@H]3C=C(C4=CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)Cl)=O NBIIDNCPASZGOS-UCCCNAJCSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- JEZSSAUCCFAPNQ-MKIHCWSVSA-N [2-[(8S,9S,10R,13S,14S,17R)-6-chloro-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC([C@]1(CC[C@H]2[C@@H]3C=C(C4=CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)Cl)O)=O JEZSSAUCCFAPNQ-MKIHCWSVSA-N 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 2
- -1 dihydrogen phosphate ester Chemical class 0.000 abstract 2
- 150000007659 semicarbazones Chemical class 0.000 abstract 2
- YEYJDQPFEHWBKV-HAPMCFBCSA-N C(C)(=O)OC=C[C@]1([C@@H](C[C@H]2[C@@H]3C=C(C4=C=CCC[C@]4(C)[C@H]3C=C[C@]12C)F)CF)O Chemical compound C(C)(=O)OC=C[C@]1([C@@H](C[C@H]2[C@@H]3C=C(C4=C=CCC[C@]4(C)[C@H]3C=C[C@]12C)F)CF)O YEYJDQPFEHWBKV-HAPMCFBCSA-N 0.000 abstract 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 abstract 1
- XMJUTQWHACHVRR-GLWIGQELSA-N [(8R,9S,10R,13S,14S,16R,17R)-17-acetyl-6-chloro-16-(chloromethyl)-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound ClC1=C[C@H]2[C@@H]3C[C@H]([C@](C(C)=O)([C@]3(CC[C@@H]2[C@]2(CCC(C=C12)=O)C)C)OC(C)=O)CCl XMJUTQWHACHVRR-GLWIGQELSA-N 0.000 abstract 1
- AXFXBVQPNHNICP-VGPXMGFGSA-N [2-[(8S,9S,10R,13S,14S)-6-chloro-10,13,16-trimethyl-3,11-dioxo-2,8,9,12,14,15-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound ClC1=C[C@H]2[C@@H]3CC(=C(C(COC(C)=O)=O)[C@]3(CC([C@@H]2[C@]2(CCC(C=C12)=O)C)=O)C)C AXFXBVQPNHNICP-VGPXMGFGSA-N 0.000 abstract 1
- JHVFTLQVFMTCKO-JSVZATNISA-N [2-[(8S,9S,10R,13S,14S)-6-chloro-10,13-dimethyl-3,11-dioxo-2,8,9,12,14,15-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC(C1=CC[C@H]2[C@@H]3C=C(C4=CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)Cl)=O JHVFTLQVFMTCKO-JSVZATNISA-N 0.000 abstract 1
- BTYUIKXUKULDOY-ODUXPPJNSA-N [2-[(8S,9S,10R,13S,14S,17R)-3-ethoxy-17-hydroxy-10,13-dimethyl-16-methylidene-11-oxo-1,2,7,8,9,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC([C@]1(C(C[C@H]2[C@@H]3CC=C4C=C(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)OCC)=C)O)=O BTYUIKXUKULDOY-ODUXPPJNSA-N 0.000 abstract 1
- YIBHQVQKOWQRFO-RFCNLIAHSA-N [2-[(8S,9S,10R,13S,14S,17R)-6-chloro-17-hydroxy-10,13-dimethyl-16-methylidene-3,11-dioxo-2,8,9,12,14,15-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C(C)(=O)OCC([C@]1(C(C[C@H]2[C@@H]3C=C(C4=CC(CC[C@]4(C)[C@H]3C(C[C@]12C)=O)=O)Cl)=C)O)=O YIBHQVQKOWQRFO-RFCNLIAHSA-N 0.000 abstract 1
- CFTDFUCXFLEWOX-FCUGKPCYSA-N [2-[(8s,9s,10r,13s,14s,17r)-17-hydroxy-10,13-dimethyl-16-methylidene-3,11-dioxo-2,6,7,8,9,12,14,15-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O CFTDFUCXFLEWOX-FCUGKPCYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- RZRPTBIGEANTGU-IRIMSJTPSA-N adrenosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RZRPTBIGEANTGU-IRIMSJTPSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000003862 glucocorticoid Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000002395 mineralocorticoid Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 230000003096 thymolvtic effect Effects 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
1,215,752. 4-Chloro-steroids. F. HOFFMANNLA ROCHE & CO. A.G. 6 Aug., 1968 [7 Aug., 1967], No. 37510/68. Heading C2U. The invention comprises steroids of formula wherein R<SP>1</SP> is F, Cl, Br or C 1-8 alkyl, and A represents one of the following entities wherein R<SP>2</SP> is H or F; R<SP>3</SP> is H, OH, C 1-8 alkoxy, C 1-8 alkanoyloxy, COCHF 2 , COCHCl 2 or C 1-8 alkyl; R<SP>4</SP> is C 1-7 alkylidene or α-CH 2 Cl, (the latter, only when n is 0 or 1, X is a #<SP>1</SP>-unsaturation or 2-chloro group, R<SP>2</SP> is H and R<SP>3</SP> is OH or C 1-8 alkanoyloxy); or R<SP>3</SP> + R<SP>4</SP> together form a 1<SP>1</SP>-alkyl-alkylidenedioxy group; R<SP>5</SP> is H or C 1-8 alkanoyl; R<SP>6</SP> is H, C 1-8 alkyl or optionally halo-substituted C 2-7 monounsaturated aliphatic hydrocarbyl; R<SP>7</SP> is H or CH 3 ; R<SP>8</SP> is α-H, α-F, α-Cl or α-Br; R<SP>9</SP> is H, a hydroxy group, the dihydrogen phosphate ester thereof or an alkali metal salt thereof, or a C 1-8 alkanoyloxy group; R<SP>10</SP> is C 1-7 alkylidene, α-CH 2 Cl, α-CH 2 F, α-Cl or α-F; R<SP>11</SP> is OH or C 1-8 alkanoyloxy; or, when R<SP>9</SP> is H, R<SP>10</SP> + R<SP>11</SP> together form a 1<SP>1</SP>-alkylalkylidenedioxy group; or R<SP>9</SP> + R<SP>11</SP> together form a 1<SP>1</SP>-alkoxy-alkylidenedioxy group; n is 0 or 1; X is a #<SP>1</SP>-unsaturation or a 2-chloro or 1α,2α-methylene group; X<SP>1</SP> is a #<SP>1</SP>-unsaturation or a 2-chloro group; Y is CH 2 , CHOH or CO; Z is CHOH, CO, α-(alkyl- or aryl-sulphonyloxy) - methylene or, (when R<SP>8</SP> is α-H and R<SP>9</SP> is other than H), methylene, or, (when R<SP>8</SP> = Cl), #-chloromethylene; or x + R<SP>8</SP> together represent a #<SP>9</SP>(<SP>11</SP>)-unsaturation or a 9#, 11#-epoxy group. The above compounds are prepared (i) by chlorination of the corresponding 4-unsubstituted compounds; and (ii) the action of a strong acid on a steroid of formula to obtain the corresponding 16-methylene-17α- hydroxy-steroid. Product interconversions described are 2-chlorination; 1,2-dehydrogenation; oxidation of 11-OH to 11-OXO; sulphonation of 11α-OH; dehydration of a 9α-H-11#-OH compound or desulphonation of a 9α-H-11α- sulphonyloxy compound to yield a #<SP>9</SP>(<SP>11</SP>)- compound; treatment of #<SP>9</SP>(<SP>11</SP>)-compounds with HOCl or HOBr to give 9α-(Cl or Br)-11-OH compounds; dehydrohalogenating 9α-(Cl or Br)-11-OH compounds to 9#,11#-epoxy compounds; treatment of 9#,11#-epoxy compounds with HF, HCl, HBr or a chlorinating agent to give 9α-halo-11-OH or 9α,11#-dichloro compounds; esterification of 17- and/or 21-hydroxy groups; and saponification of 17- and/or 21-alkanoyloxy groups. 6 - Fluoro - 16α,17α - isopropylidenedioxypregna - 4,6 - diene - 3,11,20 - trione, 21 - acetoxy - 6 - fluoro - 16α - fluoromethyl - 17α - hydroxy - pregna - 4,6 - diene 3,11,20 - triene and 21 - acetoxy - 6,16α - difluoro - 17α - hydroxypregna - 4,6 - diene - 3,11,20 - trione are prepared by 6,7-dehydrogenation of the corresponding pregn-4-enes. 6 - Chloro - 16α - chloromethyl - 17α - acetoxypregna - 4,6 - diene - 3,20 - dione is prepared from 16α - chloromethyl - 17α - acetoxy - pregn- 4 - ene - 3,20 - dione via 17α - acetoxy - 16α chloromethyl - 3 - ethoxy - pregna - 3,5 - dien - 20- one and 6# - chloro - 16α - chloromethyl - 17α- acetoxy - pregn - 4 - ene - 3,20 - dione. 21 - Acetoxy - 6 - chloro - 17α - hydroxy - 16- methylene - pregna - 4,6 - diene - 3,11,20 - trione is prepared from 21-acetoxy-17α-hydroxy-16- methylene - pregn - 4 - ene - 3,11,20 - trione via 21 - acetoxy - 3 - ethoxy - 17α - hydroxy - 16- methylene - pregna - 3,5 - diene - 11,20 - dione and 21 - acetoxy - 6# - chloro - 17α - hydroxy - 16- methylene - pregn - 4 - ene - 3,11,20 - trione. 4,6 - Dichloro - 21 - acetoxy - 16α,17α - epoxy- 16# - methyl - pregna - 4,6 - diene - 3,11,20- trione (X) is prepared by the sequence: 21- acetoxy - 6 - chloro - 17α - hydroxy - pregna - 4,6- diene - 3,11,20 - trione (XI) # the 3,20 - bis- (semicarbazone) of XI # 21 - acetoxy - 6- chloro - pregna - 4,6,16 - triene - 3,11,20 - trione 3,20 - bis(semicarbazone) # 21 - hydroxy - 6- chloro - pregna - 4,6,16 - triene - 3,11,20 - trione (XII) # the 21-acetate of XII # 6-chloro-21- acetoxy - 16α,17α - methyleneazo - pregna - 4,6- diene - 3,11,20 - trione # 6 - chloro - 21 - acetoxy - 16 - methyl - pregna - 4,6,16 - triene- 3,11,20 - trione # an unidentified trichloro intermediate (by treatment with Cl 2 /CCl 4 ) # an unidentified oil (by treatment with Na 2 HPO 4 / CF 3 CO 3 H) # X (by treatment with pyridine). 2#,4,6 - Trichloro - 21 - acetoxy - 16α,17α- epoxy - 16# - methyl - pregna - 4,6 - diene- 3,11,20-trione is prepared by chlorination of the corresponding 2-dechloro compound. The compounds of Formula I are stated to possess progestational, glucocorticoid, mineralocorticoid, anti inflammatory and thymolytic activities, and may be made up with carriers into pharmaceutical compositions for oral, parenteral and topical administration.
[GB1215752A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65860267A | 1967-08-07 | 1967-08-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32344L true IE32344L (en) | 1969-02-07 |
| IE32344B1 IE32344B1 (en) | 1973-06-27 |
Family
ID=24641922
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE950/68A IE32397B1 (en) | 1967-08-07 | 1968-08-06 | Halogenated steroids and process for the manufacture thereof |
| IE949/68A IE32344B1 (en) | 1967-08-07 | 1968-08-06 | Halogenated steroids and process for the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE950/68A IE32397B1 (en) | 1967-08-07 | 1968-08-06 | Halogenated steroids and process for the manufacture thereof |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS5021474B1 (en) |
| AT (4) | AT290031B (en) |
| BE (2) | BE719050A (en) |
| CH (10) | CH544081A (en) |
| DE (1) | DE1793063A1 (en) |
| DK (2) | DK126187B (en) |
| ES (2) | ES356957A1 (en) |
| FI (2) | FI45322C (en) |
| FR (4) | FR8417M (en) |
| GB (2) | GB1217530A (en) |
| IE (2) | IE32397B1 (en) |
| IL (2) | IL30492A (en) |
| MY (1) | MY7100216A (en) |
| NL (2) | NL6811218A (en) |
| NO (2) | NO128765B (en) |
| SE (2) | SE351633B (en) |
| YU (2) | YU33190B (en) |
-
1968
- 1968-07-17 CH CH419171A patent/CH544081A/en not_active IP Right Cessation
- 1968-07-17 CH CH418571A patent/CH541549A/en not_active IP Right Cessation
- 1968-07-17 CH CH419071A patent/CH541550A/en not_active IP Right Cessation
- 1968-07-17 CH CH418771A patent/CH544073A/en not_active IP Right Cessation
- 1968-07-17 CH CH419271A patent/CH544076A/en not_active IP Right Cessation
- 1968-07-17 CH CH418871A patent/CH544072A/en not_active IP Right Cessation
- 1968-07-17 CH CH1070668A patent/CH555329A/en not_active IP Right Cessation
- 1968-07-17 CH CH418671A patent/CH544075A/en not_active IP Right Cessation
- 1968-07-17 CH CH1070568A patent/CH565198A5/xx not_active IP Right Cessation
- 1968-07-17 CH CH418971A patent/CH544074A/en not_active IP Right Cessation
- 1968-07-30 DE DE19681793063 patent/DE1793063A1/en active Pending
- 1968-08-05 IL IL30492A patent/IL30492A/en unknown
- 1968-08-05 AT AT08882/69A patent/AT290031B/en not_active IP Right Cessation
- 1968-08-05 AT AT888169A patent/AT290030B/en not_active IP Right Cessation
- 1968-08-05 BE BE719050D patent/BE719050A/xx unknown
- 1968-08-05 YU YU1858/68A patent/YU33190B/en unknown
- 1968-08-05 IL IL6830491A patent/IL30491A/en unknown
- 1968-08-05 BE BE719049D patent/BE719049A/xx unknown
- 1968-08-05 AT AT760368A patent/AT285832B/en not_active IP Right Cessation
- 1968-08-05 YU YU01857/68A patent/YU185768A/en unknown
- 1968-08-05 AT AT760468A patent/AT285833B/en not_active IP Right Cessation
- 1968-08-06 ES ES356957A patent/ES356957A1/en not_active Expired
- 1968-08-06 JP JP43055307A patent/JPS5021474B1/ja active Pending
- 1968-08-06 FR FR162043A patent/FR8417M/fr not_active Expired
- 1968-08-06 FR FR162042A patent/FR7921M/fr not_active Expired
- 1968-08-06 GB GB37509/68A patent/GB1217530A/en not_active Expired
- 1968-08-06 ES ES356956A patent/ES356956A1/en not_active Expired
- 1968-08-06 FR FR1588547D patent/FR1588547A/fr not_active Expired
- 1968-08-06 IE IE950/68A patent/IE32397B1/en unknown
- 1968-08-06 NO NO03087/68A patent/NO128765B/no unknown
- 1968-08-06 NO NO03088/68A patent/NO128766B/no unknown
- 1968-08-06 GB GB37510/68A patent/GB1215752A/en not_active Expired
- 1968-08-06 DK DK379168AA patent/DK126187B/en unknown
- 1968-08-06 DK DK379268AA patent/DK122606B/en unknown
- 1968-08-06 FR FR1588548D patent/FR1588548A/fr not_active Expired
- 1968-08-06 IE IE949/68A patent/IE32344B1/en unknown
- 1968-08-07 JP JP43055539A patent/JPS5010859B1/ja active Pending
- 1968-08-07 SE SE10631/68A patent/SE351633B/xx unknown
- 1968-08-07 SE SE10630/68A patent/SE351632B/xx unknown
- 1968-08-07 FI FI682234A patent/FI45322C/en active
- 1968-08-07 FI FI682233A patent/FI45321C/en active
- 1968-08-07 NL NL6811218A patent/NL6811218A/xx unknown
- 1968-08-07 NL NL6811217A patent/NL6811217A/xx unknown
-
1971
- 1971-12-30 MY MY216/71A patent/MY7100216A/en unknown
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