CY1231A - N-cyano-n'-alkynyl-s-substituted isothioureas - Google Patents
N-cyano-n'-alkynyl-s-substituted isothioureas Download PDFInfo
- Publication number
- CY1231A CY1231A CY1231A CY123178A CY1231A CY 1231 A CY1231 A CY 1231A CY 1231 A CY1231 A CY 1231A CY 123178 A CY123178 A CY 123178A CY 1231 A CY1231 A CY 1231A
- Authority
- CY
- Cyprus
- Prior art keywords
- cyano
- butyn
- compound
- methyl
- alkynyl
- Prior art date
Links
- 150000002541 isothioureas Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- -1 4 - methyl - 5 - imidazolyl Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 4
- YLBIBZCIFHPPKA-UHFFFAOYSA-N but-2-yn-1-amine Chemical compound CC#CCN YLBIBZCIFHPPKA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- AOQBTOKIEVBYSK-UHFFFAOYSA-N methyl n-cyano-n'-prop-2-ynylcarbamimidothioate Chemical compound N#CNC(SC)=NCC#C AOQBTOKIEVBYSK-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XSBPYGDBXQXSCU-UHFFFAOYSA-N but-3-yn-1-amine Chemical compound NCCC#C XSBPYGDBXQXSCU-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Chemical group 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MWSSYOOKGBJZFI-UHFFFAOYSA-N methyl n'-but-2-ynyl-n-cyanocarbamimidothioate Chemical compound N#CN=C(SC)NCC#CC MWSSYOOKGBJZFI-UHFFFAOYSA-N 0.000 description 1
- GWIZVIJRZWIPIK-UHFFFAOYSA-N methyl n'-but-3-yn-2-yl-n-cyanocarbamimidothioate Chemical compound N#CNC(SC)=NC(C)C#C GWIZVIJRZWIPIK-UHFFFAOYSA-N 0.000 description 1
- QLZLYDDNEKLGBF-UHFFFAOYSA-N methyl n'-but-3-ynyl-n-cyanocarbamimidothioate Chemical compound N#CNC(SC)=NCCC#C QLZLYDDNEKLGBF-UHFFFAOYSA-N 0.000 description 1
- BUXPBJUGIAOFFS-UHFFFAOYSA-N methyl n-cyano-n'-(2-methylbut-3-yn-2-yl)carbamimidothioate Chemical compound N#CNC(SC)=NC(C)(C)C#C BUXPBJUGIAOFFS-UHFFFAOYSA-N 0.000 description 1
- LSXKPNRVECVYHT-UHFFFAOYSA-N methyl n-cyano-n'-pent-4-ynylcarbamimidothioate Chemical compound N#CNC(SC)=NCCCC#C LSXKPNRVECVYHT-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- LMDDPGHBJXJGAC-UHFFFAOYSA-N pent-4-yn-1-amine Chemical compound NCCCC#C LMDDPGHBJXJGAC-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENT SPECIFICATION
Oi (21) Application No. 27637/79 (22) Filed 26 May 1978 (62) Divided out of No. 1598628 (31) Convention Application No. 803009 0© (32) Filed 3 June 1977
(31) Convention Application No. 826796
(32) Filed 22 Aug. 1977 ^ (31) Convention Application No. 848959
(32) Filed 7 Nov. 1977 in
(33) United States of America (US)
(44) Complete Specification published 23 Sept. 1981
(51) INT CL3 C07C 157/14
(52) Index at acceptance
C2C 202 20Y 30Y 320 326 373 37Y 746 758 AA RH
(54) N-CYANO-N'-ALKYNYL-S-SUBSTITUTED ISOTHIOUREAS
(71) We, BRISTOL-MYERS COMPANY, a Corporation organised and existing under the laws of the State of Delaware United States of America, of 345 Park Avenue, State of New York, 10022, United States of America, do hereby declare the invention for which we pray that a patent may be granted to us and the 5 method by which it is to be performed to be particularly described in and by the 5
following statement:—
The present invention relates to certain N-cyano-N'-alkynyl-S-substituted isothioureas which are intermediates useful in the preparation of certain N-cyano-N'-{2 - [(4 - methyl - 5 - imidazolyl)methylthio] - ethyl}-N"-alkynylguanidines 10 which are H2 receptor blocking agents, which inhibit gastric acid secretion and 10 which are useful in the treatment of ulcers.
Accordingly, the present invention provides a compound of the formula
NCN
II
R2S—CNH—R1 III
wherein R1 is a straight or branched chain alkynyl group containing from 3 to 9 15 carbon atoms and R2 is C,_9alkyl, aryl, substituted aryl, aralkyl, —CH2CN, 15 —CH,COOH or —CH2COOR' wherein R' is C,_9 lower alkyl.
"In a preferred embodiment, R1 of the compound of formula III is
—CHOCR4
I
ch3
in which R* is hydrogen or methyl; in another preferred embodiment R' is ;20 —<CH2)nC=CR4 20 ;in which n is an integer of from 1 to 6 and R4 is hydrogen or methyl; in another preferred embodiment R1 is ;CH3 ! ;—C—OCR4 ;I ;ch3 ;in which R4 is hydrogen or methyl. ;25 In a more preferred embodiment, R1 is a propargyl, 2-butyn-l-yl, 3-butyn-l-yl, 25 ;2-methyl-3-butyn-2-yl, or 4-pentyn-l-yl group. ;<"> 1 598 629 ;BNSDOCID: <GB 1598629A L> ;1,598,629 ;The compounds of the present invention are intermediates in the preparation of compounds of the formula ;N y^°H3 ;OL ;ncn ;1 ;n ch2sch2ch2nhcnh-r h ;10 ;wherein R1 is a straight or branched chain alkynyl group containing from 3 to 9 carbon atoms, or non-toxic pharmaceutically acceptable acid addition salts thereof. _ . ;The compounds of formula I are described and claimed in our copending patent application No. 23611/7*8. Serial No. 1,598,628.
The compounds of formula I and salts thereof may be prepared by reacting a compound of the formula
10
a i
H
ch.
ch2sch2ch2nh2
ii or an acid addition salt thereof, with a compound of the formula
NCN
II
R2S—CNH—R1
III
wherein R1 and R2 are as above defined, and, if desired, converting the resulting 15 compound of formula I in basic form or an acid addition salt thereof to the corresponding non-toxic pharmaceutically acceptable acid addition salt or free base form.
This process is illustrated by way of example by the following reaction scheme: ch-,
H2sch2CH2NH2 +
ncn
2. n rs-cnhch2c3ch
15
rT
^N-^C
ch.
ncn
H
ch2sch2ch 2nhcnhch 2csch
20 wherein R2 is as above defined
The compounds of the present invention may be prepared by the reaction of an appropriately substituted cyanodithioiminocarbonate with an alkynylamine having from 3 to 9 carbon atoms. The general reaction scheme is given below:—
20
BNSDQCID: <GB 1598629A_I_>
3
5
10
15
20
25
30
35
40
45
50
_3
5
10
15
20
25
30
35
40
45
50
1,598,629
NCN
II
(R2S)2G=NCN+ H2NR'-»R2S—CNHR'+R2SH
The present invention will be further described with reference to the following Examples.
EXAMPLE 1 N-Cyano-N'-propargyl-S-methylisothiourea A solution of dimethyl cyanodithioiminocarbonate (16.00 g, 0.109 mole) and propargylamine (6.03 g, 0.109 mole) in acetonitrile (320 ml) was stirred at reflux for 4 hours, and then at 25°C for 12 hours. Workup gave the title compound (13.58 g, 81%), mp 160—164°C.
EXAMPLE 2 N-(2-Butyn-l-yl)-N'-cyano-S-methylisothiourea A solution of dimethyl cyanodithioiminocarbonate (10.00 g, 0.684 mole) and 2-butyn-l-yl-amine (4.73 g, 0.684 mole) in acetonitrile (200 ml) was stirred at reflux for 2.5 hours. The mixture was cooled, then filtered to yield the title compound, mp 180—183°C.
EXAMPLE 3
N-( 1,1 -Dimethylpropargyl)-N'-cyano-S-methylisothiourea The general procedure of Example 2 is repeated except that the 2-butyn-l-yl-amine utilized therein is replaced by an equimolar amount of 1,1-dimethylpropargylamine, and the title product is thereby produced.
EXAMPLE 4 N-( 1 -Methylpropargyl)-N'-cyano-S-methylisothiourea The general procedure of Example 2 is repeated except that the 2-butyn-l-yl-amine utilized therein is replaced by an equimolar amount of 1-methylpropargylamine, and the title product is thereby produced.
EXAMPLE 5 N-Cyano-N'-propargyl-S-methylisothiourea A solution of dimethyl cyanodithioiminocarbonate (16.00 g, 0.109 mole) and propargylamine (6.03 g, 0.109 mole) in acetonitrile (320 ml) was stirred at reflux for 4 hours, and then at 25 °C for 12 hours. The mixture was cooled and filtered to yield the title compound (13.58 g, 81%), mp 160—164°C.
EXAMPLE 6 N-Cyano-N'-(2-butyn-l-yl-S-methylisothiourea A solution of dimethyl cyanodithioiminocarbonate (10.00 g, 0.0684 mole) and 2-butyn-l-yl-amine (4.73 g, 0.0684 mole) in acetonitrile (200 ml) was stirred at 25°C for 0.5 hour, and then at reflux for 2.5 hours. The mixture was cooled, then filtered to yield the title compound, mp 180—183°C.
EXAMPLE 7 N-Cyano-N'-(3-butyn-1 -yl)-S-methylisothiourea The general procedure of Example 5 is repeated, except that the propargylamine utilized therein is replaced by an equimolar amount of 3-butyn-l-yl-amine, and the title compound is thereby produced.
EXAMPLE 8 N-Cyano-N'-(4-pentyn-1 -yl)-S-methylisothiourea The general procedure of Example 5 is repeated, except that the propargylamine utilzed therein is replaced by an equimolar amount of 4-pentyn-l-yl-amine, and the title compound is thereby produced.
EXAMPLE 9
N-Cyano-N'-(2-methyl-3-butyn-2-yl)-S-methylisothiourea The general procedure of Example 5 is repeated, except that the propargylamine utilized therein is replaced by an equimolar amount of 1,1-dimethylpropargylamine, and the title compound is thereby produced.
1,598,629
EXAMPLE 10 N-Cyano-N'-(3-butyn-2-yl)-S-methylisothiourea The general procedure of Example 5 is repeated, except that the propargylamine utilized therein is replaced an equimolar amount of 1-methyl-5 propargylamine, and the title compound is thereby produced. 5
WHAT WE CLAIM IS:—
1. A compound of the formula
NCN
li
RZS—CNH—R1
wherein R1 is a straight or branched chain alkvnyl group containing from 3 to 9 10 carbon atoms, inclusive, and R2 is C,_9alkyl, aryl, substituted aryl, aralkyl, 10 —CH2CN, —CN,COOH or —CH2COOR' where R' is C,_9alkyl.
2. A compound as claimed in claim 1 in which R1 is
—(ch2)n=cr4
wherein n is an integer of from 1 to 6, inclusive, and R4 is hydrogen or methyl. 15 3. A compound as claimed in claim 1 in which R1 is 15
—CHC=CR4
I
ch3
wherein R4 is hydrogen or methyl.
4. A compound as claimed in claim 1 in which R1 is ch3
I
—C—OCR4
I
ch3
20 wherein R4 is hydrogen or methyl. 20
5. A compound as claimed in claim 1 wherein R1 is a propargyl, 2-butyn-l-yl, 3-butyn-l-yl, 2-methyl-3-butyn-2-yl, or 4-pentyn-I-yI group.
6. A process for preparing a compound as claimed in claim I substantially as hereinbefore described with reference to any one of the Examples.
25 7. A compound as claimed in claim 1 whenever prepared by a process as 25
Claims (1)
- claimed in claim 6.BOULT, WADE & TENNANT,27 Furnival Street,London EC4A 1PQ.Printed for Her Majesty's Stationery Office, by the Courier Press, Leamington Spa, 1981 Published by The Patent Office, 25 Southampton Buildings, London, WC2A 1AY, from which copies may be obtained.BNSDOCID: <GB 1598629A_L>
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80300977A | 1977-06-03 | 1977-06-03 | |
| US82679677A | 1977-08-22 | 1977-08-22 | |
| US05/848,959 US4112234A (en) | 1977-08-22 | 1977-11-07 | Imidazolylmethylthioethyl alkynyl guanidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1231A true CY1231A (en) | 1984-06-29 |
Family
ID=27419995
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1230A CY1230A (en) | 1977-06-03 | 1978-05-26 | N-cyano-n'-alkynyl-n''-(2-mercaptoethyl)-guanidines |
| CY1229A CY1229A (en) | 1977-06-03 | 1978-05-26 | Guanidine derivatives |
| CY1231A CY1231A (en) | 1977-06-03 | 1978-05-26 | N-cyano-n'-alkynyl-s-substituted isothioureas |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1230A CY1230A (en) | 1977-06-03 | 1978-05-26 | N-cyano-n'-alkynyl-n''-(2-mercaptoethyl)-guanidines |
| CY1229A CY1229A (en) | 1977-06-03 | 1978-05-26 | Guanidine derivatives |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS543067A (en) |
| AR (2) | AR222797A1 (en) |
| CA (1) | CA1110251A (en) |
| CH (2) | CH641167A5 (en) |
| CY (3) | CY1230A (en) |
| DD (1) | DD140038A5 (en) |
| DE (1) | DE2824066A1 (en) |
| DK (1) | DK243178A (en) |
| ES (3) | ES470474A1 (en) |
| FI (1) | FI69069C (en) |
| FR (2) | FR2401143A1 (en) |
| GB (3) | GB1598628A (en) |
| GR (1) | GR73860B (en) |
| HK (3) | HK38084A (en) |
| HU (1) | HU186766B (en) |
| IE (1) | IE47543B1 (en) |
| IL (1) | IL54819A (en) |
| KE (1) | KE3373A (en) |
| LU (1) | LU79725A1 (en) |
| MY (3) | MY8500453A (en) |
| NL (1) | NL7805935A (en) |
| NO (3) | NO152214C (en) |
| NZ (1) | NZ187376A (en) |
| SE (3) | SE443784B (en) |
| SG (1) | SG8584G (en) |
| YU (4) | YU129778A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS568352A (en) * | 1979-07-03 | 1981-01-28 | Shionogi & Co Ltd | Aminoalkylvenzene derivative |
| US4339439A (en) * | 1981-01-19 | 1982-07-13 | Bristol-Myers Company | Pharmaceutical methods and compositions |
| JPS6018010U (en) * | 1983-07-18 | 1985-02-07 | 日産自動車株式会社 | Temperature adjustment mechanism of vehicle air conditioner |
| JPS60113211U (en) * | 1984-01-06 | 1985-07-31 | 松下電器産業株式会社 | Automotive air conditioner |
| ES2007948A6 (en) * | 1988-07-06 | 1989-07-01 | Vinas Lab | Propargylguanidine derivatives and process for the preparation thereof. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024271A (en) * | 1971-03-09 | 1977-05-17 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1531221A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for preparing guanidine derivatives |
| GB1531231A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for the production of cyanoguanidine derivatives |
| GB1533380A (en) * | 1974-09-02 | 1978-11-22 | Smith Kline French Lab | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
-
1978
- 1978-05-25 NZ NZ187376A patent/NZ187376A/en unknown
- 1978-05-25 CA CA304,045A patent/CA1110251A/en not_active Expired
- 1978-05-26 GB GB23611/78A patent/GB1598628A/en not_active Expired
- 1978-05-26 CY CY1230A patent/CY1230A/en unknown
- 1978-05-26 CY CY1229A patent/CY1229A/en unknown
- 1978-05-26 GB GB27637/79A patent/GB1598629A/en not_active Expired
- 1978-05-26 GB GB18923/80A patent/GB1598630A/en not_active Expired
- 1978-05-26 CY CY1231A patent/CY1231A/en unknown
- 1978-05-29 LU LU79725A patent/LU79725A1/en unknown
- 1978-05-29 GR GR56374A patent/GR73860B/el unknown
- 1978-05-31 NL NL7805935A patent/NL7805935A/en not_active Application Discontinuation
- 1978-05-31 DK DK243178A patent/DK243178A/en not_active Application Discontinuation
- 1978-05-31 AR AR272401A patent/AR222797A1/en active
- 1978-05-31 IL IL54819A patent/IL54819A/en unknown
- 1978-05-31 FI FI781737A patent/FI69069C/en not_active IP Right Cessation
- 1978-05-31 YU YU01297/78A patent/YU129778A/en unknown
- 1978-06-01 DE DE19782824066 patent/DE2824066A1/en not_active Withdrawn
- 1978-06-02 HU HU811135A patent/HU186766B/en unknown
- 1978-06-02 NO NO781928A patent/NO152214C/en unknown
- 1978-06-02 ES ES470474A patent/ES470474A1/en not_active Expired
- 1978-06-02 SE SE7806525A patent/SE443784B/en unknown
- 1978-06-02 JP JP6590078A patent/JPS543067A/en active Granted
- 1978-06-02 CH CH609278A patent/CH641167A5/en not_active IP Right Cessation
- 1978-06-02 IE IE1112/78A patent/IE47543B1/en unknown
- 1978-06-02 FR FR7816601A patent/FR2401143A1/en active Granted
- 1978-06-05 DD DD78205794A patent/DD140038A5/en unknown
-
1979
- 1979-03-01 ES ES478203A patent/ES478203A1/en not_active Expired
- 1979-03-01 ES ES478202A patent/ES478202A1/en not_active Expired
- 1979-03-05 YU YU530/79A patent/YU41620B/en unknown
- 1979-05-16 NO NO791637A patent/NO791637L/en unknown
- 1979-10-26 AR AR278645A patent/AR222503A1/en active
- 1979-11-23 FR FR7928943A patent/FR2436138A1/en active Granted
-
1982
- 1982-09-27 YU YU2154/82A patent/YU40624B/en unknown
- 1982-09-27 YU YU2155/82A patent/YU40625B/en unknown
-
1983
- 1983-09-12 NO NO833255A patent/NO151824C/en unknown
- 1983-10-07 CH CH549283A patent/CH644591A5/en not_active IP Right Cessation
-
1984
- 1984-01-30 SG SG85/84A patent/SG8584G/en unknown
- 1984-02-10 KE KE3373A patent/KE3373A/en unknown
- 1984-03-16 SE SE8401491A patent/SE8401491D0/en not_active Application Discontinuation
- 1984-03-16 SE SE8401492A patent/SE8401492L/en not_active Application Discontinuation
- 1984-05-03 HK HK380/84A patent/HK38084A/en unknown
- 1984-05-03 HK HK381/84A patent/HK38184A/en unknown
- 1984-05-03 HK HK382/84A patent/HK38284A/en unknown
-
1985
- 1985-12-30 MY MY453/85A patent/MY8500453A/en unknown
- 1985-12-30 MY MY451/85A patent/MY8500451A/en unknown
- 1985-12-30 MY MY452/85A patent/MY8500452A/en unknown
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