前苏联专利SU1364240A3 Method of obtaining derivatives of 4,5,6,7-tetrahydrothiazolo-(5,4-c)-pyridine or pharmaceutically a

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专利摘要:
A compound of formula I: <IMAGE> wherein either (i) each of R1 and R2 independently represents a hydrogen atom or an organic group, or (ii) R1 and R2 linked together form a heterocyclic ring or (iii) R2 is hydrogen and R1 is <IMAGE> wherein each of R6 and R7 independently represents hydrogen or an organic group, n is 0-3, X is O, S, NH, NR8, CHNO2 or CHSO2R4, wherein R8 and R4 are organic groups and R3 represents an organic group. The compound of formula I is effective as an anti-ulcer agent and is highly effective as a histamine H2-receptor antagonist.
公开号:SU1364240A3
申请号:SU843824691
申请日:1984-12-14
公开日:1987-12-30
发明作者:Мария Ладзарини Анна；Скарпони Уго；де Кастильоне Роберто；Чезерани Роберто；Кастелло Ренато；Ваги Фабрицио；Тоти Даниэла
申请人:Фармиталия Карло Эрба С.П.А. (Фирма)；
IPC主号:

专利说明:

113642402
. The invention relates to the preparation of Analogously to Example 1, however, the iso-derivatives of 4,5,6,7-tetrahydrothiazo-phenyl isothiocyanate instead of the melo (5,4-c) -pyridine of the general formula Itilisothiocyanate, in 40% yield
N-receive specified in the title Compounds 1, V GoT 1G-G-MW-H fr nenie (so pl.).
K-tCHzln- S 5 BN Kz (I) —P r and m e r 4. 2-Amino-5- (benzo-2Xyl-thiocarbamoyl) -4,5,6,7-tetrahydrogde n 0 or 1; thiazolo- (5,4-c) -pyridine (p O, R
R and R, each independently hydrogen 10 з COR4; X S; ) or methyl, or H water is analogous to example 1, but isrod, R is a group of R, -NH-C NR ,, favor of benzoyl isothiocyanate instead of
where is R; and R, -.metstisothiocyanate, obtained with
hydrogen or cyclohexnyl — the yield indicated in the title
. connection (m.p. 158-160 C).
/
X - oxygen, sulfur or imino-t 5 2-Amino-5- (methyl-group-carbamoyl) -4,5,6,7-tetrahydrothiazolo D - (T-G - PCP (G-H H peak-5 (5 , 4-c) -pyridine (n O, R, R, H;
Kj t.L, -L4; alkyl. Be (,) dick R CH X - o)
loalkyl, phenyl, benzyl s t
p-toluenesulfonyl 20 Analogously to example 1, however, ist. lgtgtopruz of methyl isocyanate instead of methyl iJtltd at
or their pharmaceutically acceptable co-isothiocyanate, get with 54%
anti-ulcer, anti-release, titled compound secretory and antihistamine deist- ™ 02 C with decomposition), gjjg 2-Amino-5- (The purpose of the invention is decomp-1-carbamoyl) -4,5,6 , 7-tetrahydro-trial of a process for the preparation of novel pro-azolo- (5,4-c) -pyridine (n 0; R, aqueous tetrahydrothiazolo- (5,4-с) -pi-2 H; R - CH (CH3) 2 X - 0). Ridine, exhibiting valuable pharmacolo-analogous to Example 1, however, has isgicic properties. isopropshthisocyanate instead
Example 1. 2-AMINO-5- (methyl methylisothiocyanate, get the specified hyocarbamoyl) -4,5,6,7-tetrahydrothy- “°” title compound (t.pl.190 gold- (5,4-s) -pyridine (p 0; R, R, C with decomposition) with 54% of all H; Cs CH3; XS). , 55 g (10 mmol) of 2-amino-4,5,6,7- Example 7. 2-Lmio-5- (phenyltetrahydrothiazolo- (5,4-c) -pyridinecarbamoyl) -4,5,6,7- tetrahydrotase is dissolved in 25 ml of dimethylformamido- (5,4-c) -pyridine (n 0; R, R
and the resulting solution is cooled in a bath H; Rj С / Н; X 0). with icy water. Then, add analogously to example 1, but is 88 g (12 mmol) of methylisothiocyanate. 40 using phenyl isocyanate instead of methyl sput 7.5 h, the solvent is evaporated with thiocyanate to obtain indicated in
and the residue (about 2.2 g) crystallizes the title compound (mp. 204-206 ° C
from acetonitrile. This is 1.25 (53% yield),
55%) of the pure product indicated in Example 8. 2-Amino-5- (K-ben
Titles (mp. 188-190 C5 with decomposed gzilcarbamoyl) -4,5,6,7-tetrahydrodiagelment. gold- (5,4-с) -pyridine (n O, R R
Example 2. 2-Amino-5- (isopropanol; R X 0). psh1-thiocarbamoyl) -, 4,5,6,7-tetrahydro- Analogously to example 1, but using thiazolo- (5,4-c) -pyridine (n O, R favor benzyl isocyanate instead of meth R R; RJ CH (CH 3 ) 2 XS). g lysothiocyanate, get specified in
Analogously to example 1, but the title is the compound (so pl. 197-20b C)
benefit of isopropyl isothioate. Together with a yield of 47%.
Methyl isothiocyanate, with 75% yield. P p memer 9. 2-Amino-5- (K-ben-get the title of compound-soyl-amylino) -4,5,6,7-tetrahydronium (m.p. 179-180 C). thiazolo- (5,4-s) -pyridine (p O, R,
Example 3. 2-Amino-5- (fen SH1- R H; R X,
thiocarbamoyl) -4,5,6,7-tetrahydrothia-R). 2.33 g (15 mmol) 2-am.,
ash- (5,4-c) -pyridine (p O, R, 5,6,7-tetrahydrothiazolo- (5,4-c) Rj H; Rj X S). pyridine is dissolved in 30 ml of dimethyl 31 134 264
ormamide and add 2.63 g (18 mmol) of enzoyl cyanamide. Reaction mixture
5y bezp chzci ci da ra os 2 me na pa xr ge et chi ch
2 2
incubated at 70 ° C for 1 hour, and then for an additional 1 hour at. The solvent is evaporated, and the residue (about 5 g) is crystallized from acetonitrile. Obtain 3.5 g (87%) of the pure title compound (y.p. 180-181 C).
Example 10. 2-Guanidino-5- (isopropyl-thiocarbamoyl) -4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (n 0; R, Hj NC - NH, Rj CH (CH3) 2; XS).
To a solution of 0.986 g (5 mmol) of 2-guanidino-4,5,6,7-tetrahydro-thiazolo- (5,4-c) -pyridine in 15 ml of dimethyl form of the amide, after cooling, 0.606 g (6 mmol) of isopropyl isothiocyanate are added. . After 7 hours, the solvent is evaporated and the residue (about 1.6 g) is crystallized from acetonitrile. 1.24 g (yield: 83%) of the pure compound indicated in the title are obtained (m.p., 238 ° C with decomposition).
Example 11. 2-Guanidino-5- (isopropyl-carbamoyl) -4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (n 0; Rf H2N — C NH; Rj H; X 0).
Analogously to example 10, however, using isopropyl isocyanate instead of isopropyl isothiocyanate, the title compound is obtained in 70% yield (mp 210-213 ° C with decomposition).
Example 12. 2-Guanidido-5- (H-benzosch-1-amidino) -4,5,6,7-tetrahyd rothiazo- (5,4-c) -pyridine (N 0; R HjN — C NH; R H; R -
X nr
eight
R "
H; R + CtHj).
Rj CE (CEUU
To a solution of 2.96 g (15 mmol) of 2-guanidino-4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine in 30 ml of dimethylformamide was added 2.74 g (18.75 mmol) of benzoyl cyanamide . The reaction mixture is maintained at 110 ° C for 2 h, and then the solvent is evaporated. The residue (about 6 g) is crystallized from acetonitride. Obtain 2.06 g (yield 40%) of the pure compound indicated in the title (so pl. 243-246 C).
Example 13. 2- (N, N-dicyclohexylguanidino - (- 5) -isopropyl-carba MOSH1-4,5,6,7-tetrahydrothiazolo (5,4-c) -pyridine (n 0; Rj-O liH s-to-o
Rz
62% indicated in the title Comm.
H; Rj H3oCjH ;; X 0). | (msh 1 with decomposition).
0
To a solution of 2.4 g (10 mml) of 2-amino-5isopropylcarbamoyl-4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine in 20 ml of anhydrous dimethylformamide is added at room temperature under a nitrogen atmosphere. 0.337 g (3 mmol) pyridine hydrochloride and 3.09 g (15 mmol) S, K-dicyclohexylcarbodiimide, dissolved in 5 ml of anhydrous dimethylformamide. After standing for 4 days, the solvent is evaporated in vacuo, and the residue is dissolved in ice water. The aqueous solution is strongly basified with 2 N sodium hydroxide and extracted with methylene dichloride. The extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residue (about 5 g) is chromatographed on a silica gel column using ethyl acetate as eluent. 2.2 g (yield 50%) of the pure compound indicated in the title are obtained in the form of a white foam.
H-NMR indicated in the title of soy-5 dinene (CDCl, 200 MHz): 1.15 / (d, 6H, CH (CH3) 2.
1.1-2.06 / 20N, 2x1sng Sh-nn
five
0
0
five
0
five
O
five
CHj- CHj
Example 14. 2-Guanidino-5- (cyclopropsh-1-carba: moyl) -4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (n 0; R HjN-C-NH; R H; Rj-cyclopropyl; X and).
Analogously to Example 10, however, using cyclopropyl isocyanate instead of isopropylisothiocyanate, the title compound is obtained with a yield of 50% (mp 215-216 ° C).
Example 15. 2-Guanidino-5- (cyclopentyl-carbamoyl) -4,5,6,7-tetrahydro-thiazolo- (5,4-c) -pyridine (n 0; RH, jN-C-NH; R М ; Rz-cyclopentenyl; X 6).
Analogously to Example 10, however, using cyclopentyl isocyanate instead of isopropyl isothiocyanate, the title compound is obtained in a 60% yield. Disinfection (mp. 229 С with decomposition).
Example 16. 2-Guanidino-5-methyl-carbamoyl- (4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (n 0; R, - HjN-C-NH; Rj Н ; RJ Me; X 0).
Analogously to Example 10, however, using methyl isocyanate instead of isopropylisothiocyanate, is obtained with
62% indicated in the title compound o
| (msh 1 with decomposition).
., HjN-C-NH; Rj H; K, cyclohec. HjN-C-NH; Rj H; EZ-TOZIL,
Example 17. 2-Guanidino-5- (cyclohexyl-carbamoyl) -4,5,6,7-tetrahydro-thiazolo- (5,4-c) -pyridine (n 0 R, HjN-C-NH; R, strength ; X 0).
Analogously to example 10, but using cyclohexyl isocyanate instead of isopropylisothiocyanate, the title compound is obtained with a yield of 49% (m, pl. 225 ° C. with decomposition).
Example 18. 2-Guanidino-5- (tosyl-carbamoyl) -4,5,6,7-tetrahydro-thiazolo- (5,4-c) -pyridine (n 0;
R,).
Analogously to example 10, however, using tosyl isocyanate instead of isopropylisothiocyanate, the title compound is obtained with a yield of 16% (m, 227-228 ° C),
Example 19. 2-Guanidino-5- (ethyl-carbamoyl) -4,5,6,7-tetrahydrothiazolo- (554-c) -pyridine (n 0; R, - H2N – C NH; Rj – H; Rz-ztil; X 0).
Analogously to Example 10, however, using ethyl isocyanate instead of isopropyl isothiocyanate, the title compound is obtained with a yield of 53% (mp 244-245 C with decomposition).
Example 20, 2-Guanidino-5- (and. Propyl-carbamoyl) -4,5,6,7-tetrahydro-imidazolo- (55,4-c) -pyridine (n 0; R, HjN-C-NH; R H; R-propyl, X 0) „
Analogously to example 10, however, using n-propyl isocyanate instead of isopropyl isothio-dianate, the title compound is obtained with a yield of 64% (mp. 201-202 ° C with decomposition).
Example 21 2-Guanidino-4- (n-butyl-carbamoyl) -4,5,6,7-tetrahyd rothiazolo- (5,4-c) -pyridine (n 0; R -HjN-C-NH; R2 H; R -H-ayTKn; X 0) FCE 24028.. . .
Analogously to example 10, but using e-butyl isocyanate instead of isopropyl isothiocyanate, the title compound is obtained with a yield of 50% (mp 220 ° C).
EXAMPLE 22 2- (L., L-dimesh1-aminomethyl) -5- (K-isopropylthiocarbamoyl) -4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (n 1; R. Rj CHe Rz-isopropsh; XS),
To a solution of 2- (K, K-dimethylaminomethyl) -4 J 5 S, 6,7-tetrahydrothiazolo- (5,4-c) -pyridine (1.97 g 10 mmol) in acetonitrile (15 ml) at room temperature topics0
five
0
five
0
five
0
five
0
five
Isopropylisothiocyanate (1.01 g, 10 mmol) was added to the mixture and the reaction mixture was heated under reflux for 30 minutes. The solvent is evaporated to dryness and the residue (about
3g) is crystallized from diisopropyl ether. 1.91 g (yield 64%) of the pure title compound (mp) is obtained.
Example 23. 2- (S, M-dimethylaminomethyl) -5- (N-isopropylcarbamos I) - 4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine (r 1, R RJ СНз; Rz-iso-propyl; X 0).
Analogously to example 22, however, using isopropyl isocyanate, the title compound is obtained with a yield of 46% (mp. 150 ° C).
P p and m, e p 24. 2-Guanidino-5- (isopropylcarbamoyl) -4,5,6,7-tetrahydrothiazolo- (5,4-c) -pyridine hydrochloride.
2-guanidino-5- (isopropylcarbamoyl) - 4,5,6,7-tetrahydropyazole- (5,4-c) -. Pyridine (prepared according to Example 16, 141 mg) is dissolved in a stoichiometric amount of an aqueous 1N solution of HC1 and the solution is evaporated in vacuo at room temperature. A solid pale yellow residue crystallized from acetonitrile to give the pure title compound indicated (156 mg, mp 226-228 ° C, decomposition).
Anti-ulcer activity of compounds I is proved by activity in the test for inhibition of gastric ulcers in rats induced by acetylsalicylic acid (ASA). Male rats weighing 190 + 10 g, which were not given food for 15 hours, but were given any amount of water, were administered ASA (100 mg / kg orally in 0.2 ml / 100 g of boiled water) 60 minutes after oral administration. maintain a test compound. The formation of gastric ulcers was assessed after
4h after administration of the ASC. Inhibition of gastric ulcer formation was estimated as the percentage of inhibition of ulcers (the sum of ulcers in millimeters), expressed in Eflj, (a dose that reduces stomach formation by 50% compared with control rats). The results are shown in the table in column 1.,
Anti-ulcer activity of compound I was also shown in stress stress inhibition test.
rats (kept in water for 4 hours). Test compounds were administered orally one hour before: compress. In each experimental group, 6 male rats were used (140 + 10 g by weight), which were not allowed to eat for 16 hours. After stress, the rats were killed and ulcers of the stomach were evaluated by counting. Inhibition of sonoria was estimated as the percent inhibition of the indicator of sv (number of sv) and expressed as EDU. The results are shown in the table. Inhibition of duodenal ulcers caused by cysteamine in rats was evaluated for test compounds as a percentage of inhibition of ulcer (sum of lesions per rat / mm) and expressed as U. The results are shown in the table.
The gastric anti-secretory activity of compounds I was evaluated in rats by the method of pylorus ligature. In each group, 6 male rats were used (110-130 g in weight). 24 hours before the test, the rats were deprived of food, but water was given. On the day of surgery, the pylorus was sutured under light anesthesia.
Four hours after the operation, the rats died with QA nerve activation caused by OKV, collected gastric juice, centrifuged at 3500 rpm for 10 minutes, and determined the volume without digestion. The amount of free hydrochloric acid in the gastric juice was determined by titration on O, 1 n sodium hydroxide to an end point of pH 7.0. All compounds were administered intraduodenally during the ligature. Received35
by treminorin, assessed by salivation and tearing, and the degree of central cholinergic activation by pulse rate and hepothermia, Anthropinsulfate suppressed both peripheral and central effects caused by oxotremorine. The results are shown in the table. The approximate acute toxicity (LD) of the proposed compounds was determined in mice and rats by a single oral administration of increasing doses and evaluation on the seventh day. after processing. The results are shown in the table.
50
Significant results expressed as AU are shown in the table.
Compounds I were assessed for antagonistic activity to the histamine Hj receptor in vitro in the right atrium of guinea pigs. Male guinea pigs were killed by a blow to the head, the heart was quickly dissected and placed in an oxygenated Ringer-Locke solution of the following composition, g / l: NaCl 9; KC1 0.42; CaClj 0.24; 0.5; glucose 1.
The atrium was separated from the rest of the heart, placed in a 20-mm vessel containing Ringer-Locke solution, thermoregulated at and 95% Oj and 5% CQ, j were carboxygenated. Spontaneous atrial contractions adapted to condition the vessel for at least 30 minutes.
NaHCO
before experience. Histamine portions were added to the vessel, starting with 3x 10 M to 1 X Yu. Pyshennya histamine contractions caused by histamine were allowed to set before administration of the next concentration. After washing and waiting for the reduction of the atrial contraction rate, the compounds were added 5 minutes before repeating the response curve to cumulative doses of histamine. The compound was considered to be the Hj receptor antagonist if it moved the histamine dose response to the right, npji concentrations of IxlO M. The results are shown in the table.
Considering that some anti-ulcer agents possess, like atropine, noticeable, but undesirable anticholinergic activity, the compounds obtained by the proposed method were also evaluated for their antagonism against the syndrome caused by 5 intraperitoneal (sr) administration of oxotremorine to mice. Test compounds were administered to a group of male mice weighing 20-25 g at a dose of 100 mg / kg orally. The degree of peripheral {; oli;
five
0
35

40
45
50
by treminorin, assessed by salivation and tearing, and the degree of central cholinergic activation by pulse rate and hepothermia, Anthropinsulfate suppressed both peripheral and central effects caused by oxotremorine. The results are shown in the table. The approximate acute toxicity (LD) of the proposed compounds was determined in mice and rats by a single oral administration of increasing doses and evaluation on the seventh day. after processing. The results are shown in the table.

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining derivatives of 4,5, 6,7-tetrahydrothiazolo- (5,4-c) -pyridine of the general formula I
- (sn2).
X
RI
Rz
where n is 0 or 1;
RJ is each independently hydrogen or a methyl group, or Rj is hydrogen, R, is a group
Rfr - NH - C
NR
7. where Kg
and R is each hydrogen or a cyclohexyl group; X - oxygen, sulfur or iminog-ruppa;
Rj is C, -C alk1, Cz-C-cycloalkyl, phenyl, benzyl or p-toluenesulfonyl group,
or their pharmaceutically acceptable salts, characterized in that the compound of the general formula II
.
.Mlv
H
where p O or 1;
Biology activity
R is hydrogen, methyl or a group H2N-C NH;
R is hydrogen, methyl, is reacted with a compound of general formula III
Rj - N С X,
where RJ and X are the indicated values, in dimethylformamide at O-100 ° C and the target product is given in free form or in the form of pharmaceutically acceptable salts, or, if necessary, treated with dicyclohexylcarbodiimide in the presence of pyridine hydrochloride to obtain the compound total I, where is r,
OMI-C IJ-;) |
(A) 6-methyl-7-trans- (2-fencl-ethyl) -5-oxo-5H-thiazopo-13,2-a1-pyrindymic-2-carboxylic acid.
(B) K-methylcaro-amoyl-2-isothiazolo - (5, A-b) -pyridin-3-o.
Editor M. Tsitkina
Compiled by And, Bocharova
Tehred L. Serdyukova Proofreader V. But ha
Order 6387/58 Circulation 372Subscription
VNIIPI USSR State Committee
for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5
,, vi, "" sh.v.-.-. "- --------- -" - "-----
Production and printing company, Uzhgorod, st. Project, 4

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引用文献:

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CU22676A1|1996-06-21|2001-11-16|Univ Las Villas|MICROCIDE COMPOSITION FOR CONTROLLING POLLUTANTS IN VITROPLANT PRODUCTION PROCESSES|

US5718151A|1996-10-01|1998-02-17|Breed Automotive Technology, Inc.|Steering wheel mounting|

PE20040693A1|2002-11-14|2004-11-23|Novartis Ag|N-SULFONYLAMINOTIAZOLE AS MEDIATORS OF STEROID SULFATASE|

CL2004000553A1|2003-03-20|2005-02-04|Actelion Pharmaceuticals Ltd|USE OF GUANIDINE DERIVATIVE COMPOUNDS AS ANTAGONISTS OF THE FF NEUROPEPTIDE RECEIVER; COMPOUNDS DERIVED FROM GUANIDINA; PREPARATION PROCEDURES; AND PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS THEM.|

法律状态:

优先权:

申请号 | 申请日 | 专利标题

GB838333514A|GB8333514D0|1983-12-16|1983-12-16|Tetrahydrothiazolopyridine derivatives|

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