SU424349A3 - - Google Patents

Info

Publication number: SU424349A3
Authority: SU; USSR - Soviet Union
Prior art keywords: hydroxy; aminoethane; phenyl; hydrochloride; hydroxyphenyl
Prior art date: 1970-02-25

Application number

SU1752085A

Other languages

Priority date (The priority date 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 date listed.)

1970-02-25

Filing date

1971-02-17

Publication date

1974-04-15

1971-02-17 Application filed filed Critical

1974-04-15 Application granted granted Critical

1974-04-15 Publication of SU424349A3 publication Critical patent/SU424349A3/ru

Links

PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
-1 nlatinic Chemical compound 0.000 description 8
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000034 method Methods 0.000 description 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 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 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229920003776 Reny® Polymers 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
LXWZZBDWWCCJDU-UHFFFAOYSA-N benzoic acid;ethane Chemical compound CC.OC(=O)C1=CC=CC=C1 LXWZZBDWWCCJDU-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
NARWYSCMDPLCIQ-UHFFFAOYSA-N ethane;hydrochloride Chemical compound Cl.CC NARWYSCMDPLCIQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C217/48—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 unsaturated and containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
- 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)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Emergency Medicine (AREA)
Otolaryngology (AREA)
Pulmonology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

(72) Авторы изобретени Антон Ментруп, Курт (71) За витель Иностранцы Шромм, Эрнст-Отто Рент и Рудольф Кадац Иностранна фирма «К. X. Берингер Зон

(54) СПОСОБ ПОЛУЧКНИЯ ПРОИЗВОДНЫХ ЛЛ ИНОЭТА1ЮЛЛ

;ir (iriu)i;..iii ИИ 11,411 UOAl Б соль.

в случае, когда В формулы IV обозначает атом кислорода, то восстановление идет ип двул карОонильиым группам, имеюии мс м исходном сырье.

В данном ироцессе берут такие катализаторы , как никелевый, нлатиновый, палладиевьп или ко.милексные гидриды металлов.

Соединени формулы ill могут быть нолучены как в виде рацематов, так и оитически активных антиподов.

11олученные нроизводные аминоэтаиола об„чадаюг ины.ми свойства.ми, но сравиению с и: нестными ироиззодными амииоэтанола.

Ири.мер 1. 1-(4-гидроксифенил)-Ьглдрокси-2/ (3-фенил-З-гидрокси) - нроннл/аминоЭтан. /,2 г и оензилокси, ш-бромацетофенона с 12 гш-беизиламиионрониофенона иреврагцают и ацетоиитрил, удал ют ы-бензиламино1фоннофенон гидробромид и иолученный 1-1 4-бензилокси )-1-оксо-2-/ЧЗ-фенил - 3-оксо) - аронил/аминоэтан гидрируют в метаноле с никелем i-енне до тех нор, нока обе карбонильные груины ие будут восстановлены, бензнловы радикал отгценлен и нолучен 1-(4-гидрокснфеиил}ч - гидрокси-2-,/(3 - феннл-3 - гидрокси)лронил-/-а .мнноэтан.

1 азделением диастереомеров )1ым приемом получают форму X; т. нл. 158С; (юрму : т. нл. 1120-С.

Пример 2. Эритро-1-(4-гидрокснфенил)-1гидрокси-2-метил - 2-/(3 - феиил-3-гндроксн)иронил/-аД1иноэтан . 26,U г 1-(4-бензилоксифенил )-1-гндрокси-2-аминонронана в ацетонитриле в ирисутствии соды с 15,8 г ш-хлорнроинофенона нревращают в 1-(4-бензилоксифенил ) - 1-гидрокси-2-метил-2-/(3-фенил-3-оксо) 11ронил/-аминоэтан , затем с никелем Рени гидрируют в эритро-1-(4 - гидрокснфенил)- гидрокси-2-метил-2-/ (3-фенил-З-гидрокси)- иронил/-аминоэтан . Его гидрохлорид нлавитс нри 186°С.

Соответствующим образом нолучают следуюндие соединени :

эритро-1-(4-гидрокеифенил) - 1-гидрокси-2метил-2-/ (3-фенил-3 - гидрокси) -иропил/-аминоэтан , т. нл. 186°С;

бензоат 1-(3-гидроксифенил)-1-гидрокси-2-/ (3-фенил-З - гидрокси) - иронил/-аминоэтана, т. нл. 28°С;

гидрохлорид 1-(4-гидроксифенил) -1-гидрокСИ-2-/ (3-фенил-З - гидрокси-1,1-диметил)-нро11ил/-аминоэтана , т. нл. 212°С;

гндрохлорид трео-1-(4-гндроксифенил)- 1гидрокси-2-метил-2-/ (3 - фенил - 3-гидроксн)ироннл/-амнноэтана , т. ил. 160-С;

1-(4-гидрокси-3-метоксифенил) - Ьгидрокси2- .(3-фенил-З - гндроксн)-нроиил/-амииоэтана, форма X: основание т. ил. 162°С, сульфат т. ил. 163°С; форма Y: основание т. ил. 133°С, гидрохлорид т. нл. 125°С;

1-(3,5-дигидрокснфеннл) - 1-гидрокси-2-/(3фенил-3-гидрокси ) - ироиил/-аминоэтан, форма X: т. нл. 187°С, форма Y: т. нл.

феиил-а-Г11Д)Окси-1,1 дпдиггил)- нропнл/-амииоэтан-бензоат . форма X: т. нл. , форма : т. пл. 142ч; (гидрат);

шдро.хлорнд I (3-,5-Д11Г11дро и-||фе1111.) i i ||Дрокси-2-/(3-иафтил-3 - гидрокси - 1,1-дп.11. тил)-иро11нл/-амииоэтаи, форма X: ч. ii.i. , форма ; т. нл. 149 С;

беизоат 1- (4-гидрокси-2-метилфенил)- l-ni.i,рокси-2-/ (3-о - метнлфенил - 3-гндрокси)-нроиил/-аминоэтана , т. н;). HilC ;

1-(4-гидроксн-2 - метнлфеинл) -1мидрокси2-/ (3- -метоксифеиил-3 - гидроксн) - пронил/г .миноэтана, т. нл. 161 °С;

Ь (4-гидрокси-2 - метилфеннл) - 1-гидрокси2-/ (3 - л-гидрокси-лг-.хлорфеиил - 3-гндроксн)нроиил/-аминоэтаи , форма X: т. нл. 161 С (гидрохлорид), форма Y: т. нл. 8Г-С (бензоат );

1- (4-гидрокси-З-бугокснфеннл) - 1 -гпдрокси2-/ (3-.1г,л-днэтоксифеинл-3-гидрокс11)- лронил/амниоэтан , основание, т. нл. 108°С, бензоат. т. нл. 128°С, гидрохлорид, т. ил. , сульфат , т. нл. 72°С;

бензоат 1 - (4-гидроксн-З-бутоксифенил) -1 -гидрокси-2-/ (3-.U,/2 - дибутоксифеннл - З-гндрокси )-иронилу-аминоэтана, т. нл. 10ГС.

11 р (; д л; с т i з о б р е т е н .и

С HOH-CI-iR NH-CIRj),,- СНггСНОВ.гА

110

RI ато. водорода, низпип алкпл- n.ui ;;л чокснрадикал;

- атом во.чорода, метил или этил;

аюм иодорода или мстил;

R,i - атом водорода или низнп-п алкил;

Rr, - ато.1 водорода или окогрунна.

Л - фе);нл, заменденный галогеном, низнлгм алкнлом, ннзн1ей алкокснгрунной н/или оксифеннл . или кондеиснрованиьп бнниклнческн радикал, в котором кольцо, иеносредственно несоединенное е алифатическо ценыо, вл етс изоциклн-iccKHM, насыщенным гетероцик.шческнм или аро.матнческим, о т л и ч а ю щ н iiс тем, что соединение форлгулы

-CliRj-NH-CfK.

где RI. R2, R:i, R:. А имеют вышеуказашг.ле лиачени ;

/Н В - О )означает ч или -О,

ОМ ю.твергают к.ИП.штичсскому иосстаиоиленню. 5 Yr..;-r. При 51ОМ иродукт Быдел ют Е виде оспоьани или перевод т известным спосоиом и соль, 6 2. CiiOLOO ПО И. 1, О Г Л И Ч а ю щ И И С Я тем, что восстановление ведут на никелевом или платиновом, или палладиевом катализаторе.

SU1752085A 1970-02-25 1971-02-17 SU424349A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19702008654 DE2008654A1 (de)	1970-02-25	1970-02-25	Ammoathanoldenvate

Publications (1)

Publication Number	Publication Date
SU424349A3 true SU424349A3 (ru)	1974-04-15

Family

ID=5763256

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1752085A SU424349A3 (ru)	1970-02-25	1971-02-17
SU1752084A SU421181A3 (ru)	1970-02-25	1971-02-17

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU1752084A SU421181A3 (ru)	1970-02-25	1971-02-17

Country Status (18)

Country	Link
AT (3)	AT306707B (ru)
BE (1)	BE763408A (ru)
BG (3)	BG18855A3 (ru)
CH (4)	CH568269A5 (ru)
CS (3)	CS166749B2 (ru)
DE (1)	DE2008654A1 (ru)
ES (3)	ES388561A1 (ru)
FR (1)	FR2081541B1 (ru)
GB (1)	GB1340407A (ru)
IE (1)	IE34970B1 (ru)
IL (1)	IL36269A (ru)
NL (1)	NL7102432A (ru)
NO (1)	NO131983C (ru)
PL (3)	PL84395B1 (ru)
RO (3)	RO58559A (ru)
SE (1)	SE377561B (ru)
SU (2)	SU424349A3 (ru)
ZA (1)	ZA711204B (ru)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA791403B (en) *	1978-04-10	1980-05-28	Draco Ab	Composition of matter
FI70205C (fi) *	1978-05-17	1986-09-15	Degussa	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara l-/3-hydroxi-3-fenylpropyl-(2)/-/3-oxo-propyl/aminer
US4853381A (en) *	1984-04-17	1989-08-01	Glaxo Group Limited	Ethanolamine compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE630296A (ru) *	1962-03-31

1970
- 1970-02-25 DE DE19702008654 patent/DE2008654A1/de active Pending
1971
- 1971-01-22 AT AT204672A patent/AT306707B/de not_active IP Right Cessation
- 1971-01-22 AT AT54671A patent/AT305250B/de not_active IP Right Cessation
- 1971-01-22 AT AT204572A patent/AT306706B/de not_active IP Right Cessation
- 1971-02-10 RO RO68598A patent/RO58559A/ro unknown
- 1971-02-10 CS CS3275*A patent/CS166749B2/cs unknown
- 1971-02-10 CS CS3276*A patent/CS166750B2/cs unknown
- 1971-02-10 RO RO65888A patent/RO60182A/ro unknown
- 1971-02-10 CS CS982A patent/CS166748B2/cs unknown
- 1971-02-10 RO RO68599A patent/RO62244A/ro unknown
- 1971-02-17 SU SU1752085A patent/SU424349A3/ru active
- 1971-02-17 SU SU1752084A patent/SU421181A3/ru active
- 1971-02-23 CH CH875475A patent/CH568269A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875575A patent/CH568270A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH875675A patent/CH568271A5/xx not_active IP Right Cessation
- 1971-02-23 CH CH258671A patent/CH568268A5/xx not_active IP Right Cessation
- 1971-02-23 IL IL36269A patent/IL36269A/xx unknown
- 1971-02-24 BG BG018286A patent/BG18855A3/xx unknown
- 1971-02-24 PL PL1971174914A patent/PL84395B1/pl unknown
- 1971-02-24 BE BE763408A patent/BE763408A/xx unknown
- 1971-02-24 NL NL7102432A patent/NL7102432A/xx unknown
- 1971-02-24 PL PL1971174913A patent/PL84268B1/pl unknown
- 1971-02-24 ZA ZA711204A patent/ZA711204B/xx unknown
- 1971-02-24 NO NO679/71A patent/NO131983C/no unknown
- 1971-02-24 BG BG016892A patent/BG19130A3/xx unknown
- 1971-02-24 ES ES388561A patent/ES388561A1/es not_active Expired
- 1971-02-24 BG BG018287A patent/BG18856A3/xx unknown
- 1971-02-24 PL PL1971146464A patent/PL82843B1/pl unknown
- 1971-02-25 FR FR7106442A patent/FR2081541B1/fr not_active Expired
- 1971-02-25 SE SE7102409A patent/SE377561B/xx unknown
- 1971-02-25 IE IE239/71A patent/IE34970B1/xx unknown
- 1971-04-19 GB GB2245571A patent/GB1340407A/en not_active Expired
- 1971-10-20 ES ES396174A patent/ES396174A1/es not_active Expired
- 1971-10-20 ES ES396175A patent/ES396175A1/es not_active Expired

Also Published As

Publication number	Publication date
ES396175A1 (es)	1974-04-01
RO62244A (ru)	1977-08-15
ES396174A1 (es)	1974-04-01
BE763408A (fr)	1971-08-24
IE34970L (en)	1971-08-25
AT306707B (de)	1973-04-25
SE377561B (ru)	1975-07-14
CH568270A5 (ru)	1975-10-31
SU421181A3 (ru)	1974-03-25
AT306706B (de)	1973-04-25
RO58559A (ru)	1975-09-15
CH568269A5 (ru)	1975-10-31
PL82843B1 (ru)	1975-10-31
IL36269A0 (en)	1971-04-28
PL84395B1 (ru)	1976-03-31
PL84268B1 (ru)	1976-03-31
ES388561A1 (es)	1973-05-16
GB1340407A (en)	1973-12-12
DE2008654A1 (de)	1971-09-09
BG18856A3 (bg)	1975-03-20
CH568268A5 (ru)	1975-10-31
CS166748B2 (ru)	1976-03-29
NO131983B (ru)	1975-05-26
IE34970B1 (en)	1975-10-01
FR2081541A1 (ru)	1971-12-03
NO131983C (ru)	1975-09-03
CH568271A5 (ru)	1975-10-31
AT305250B (de)	1973-02-12
NL7102432A (ru)	1971-08-27
IL36269A (en)	1974-01-14
FR2081541B1 (ru)	1975-01-17
CS166750B2 (ru)	1976-03-29
BG18855A3 (bg)	1975-03-20
ZA711204B (en)	1972-10-25
SU404229A3 (ru)	1973-10-26
CS166749B2 (ru)	1976-03-29
RO60182A (ru)	1976-08-15
BG19130A3 (bg)	1975-04-30

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