Patent EP0049779A1 successfully refreshed from Google Patents.
EP0049779A1
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3-Aminoindazole derivatives and process for preparation thereof
Assignee: Asahi Kasei Corp
•
Filing: 1981-09-17
•
Granted: —
•
Expires: 2001-09-17
Abstract
Abstract A compound of the formula (I): wherein W, is a hydrogen atom or a group wherein Y is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R, and R 2 each independently is a hydrogen atom or a C 1-6 alkyl group and R,, R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; W 2 is a hydrogen atom or a group wherein Z is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R 3 and R 4 each independently is a hydrogen atom or a C 1-6 alkyl group and R 3 , R 4 and the adjacent nitrogen atom may form a C 4-6 hetercyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; when W, is a hydrogen atom, W 2 is the group; and when W 2 is a hydrogen atom, W, is the group; and the pharmaceutically acceptable acid addition salt thereof.
Inventors
- 👤 Tadayuki Ibuki
- 👤 Taisuke Sugihara
- 👤 Hiromu Kawakubo
- 👤 Takanori Sone
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 05:39
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/54; C07D231/56; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088
Claims Analysis
Total Claims: 71
Claim 1
Independent Claim
233 words
A compound of the formula (I) : wherein W 1 is a hydrogen atom or a group wherein Y is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R 1 and R 2 each independently is a hydrogen atom or a C 1-6 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; W 2 is a hydrogen atom or a group wherein Z is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R 3 and R 4 each independently is a hydrogen atom or a C 1-6 alkyl group and R3, R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; when W 1 is a hydrogen atom, W 2 is the group; and when W 2 is a hydrogen atom, W 1 is the group; and the pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
233 words
A compound of the formula (I) : wherein W 1 is a hydrogen atom or a group wherein Y is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R 1 and R 2 each independently is a hydrogen atom or a C 1-6 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; W 2 is a hydrogen atom or a group wherein Z is a C 1-6 alkylene group or a C 1-6 alkylene group having a C 1-6 alkyl group substituent; and R 3 and R 4 each independently is a hydrogen atom or a C 1-6 alkyl group and R3, R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one C 1-6 alkyl group, hydroxyl group or halogen atom; when W 1 is a hydrogen atom, W 2 is the group; and when W 2 is a hydrogen atom, W 1 is the group; and the pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
12 words
The compound of Claim 1, wherein W 1 is a hydrogen atom.
Claim 4
Dependent Claim
93 words
The compound of Claim 2 of the formula (II): Asahi-P080981EU wherein Z is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; and R 3 and R 4 each independently is a C 1-6 alkyl group and R 3 , R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyalic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom.
Claim 5
Dependent Claim
19 words
The compound of Claim 3, wherein Z is ethylene group, n-propylene group, n-hexylene group, 3-methylpropylene group or 3-(2-methylpropyl)propylene group.
Claim 6
Dependent Claim
17 words
The compound of Claim 4, wherein R 3 and R 4 are both C 1-4 alkyl groups.
Claim 7
Dependent Claim
55 words
The compound of Claim 4, wherein R 3 , R 4 and the adjacent nitrogen atom form a C4 -6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom.
Claim 8
Dependent Claim
9 words
The compound of Claim 4, wherein is piperidino group.
Claim 9
Dependent Claim
30 words
The compound of Claim 3, wherein Z is n-propylene group; and is a pyrrolidino group, homopiperidino group, piperazino group, 2-methylpiperidino group, 2,6-dimethylpiperidino group, 4-hydroxypiperidino group, 4-chloropiperidino group or 4-methylpiperazino group.
Claim 10
Dependent Claim
12 words
The compound of Claim 1, wherein W 2 is a hydrogen atom.
Claim 11
Dependent Claim
92 words
The compound of Claim 9 of the formula (III): wherein Y is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; and R 1 and R 2 each independently is a C 1-6 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom.
Claim 12
Dependent Claim
19 words
The compound of Claim 10, wherein Y is ethylene group, n-propylene group, n-hexylene group, 3-methylpropylene group or 3-(2-methylpropyl)propylene group.
Claim 13
Dependent Claim
17 words
The compound of Claim 11, wherein R 1 and R 2 are both C 1-4 alkyl groups.
Claim 14
Dependent Claim
55 words
The compound of Claim 11, wherein R 1 , R 2 and the adjacent nitrogen atom form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom.
Claim 15
Dependent Claim
8 words
The compound of Claim 11 wherein is piperidino
Claim 16
Dependent Claim
29 words
The compound of Claim 10, wherein Y is n-propylene group, and is pyrrolidino group, homopiperidino group, piperazino group, 2-methylpiperidino group, 2,6-dimethylpiperidino group, 4-hydroxypiperidino group, 4-chloropiperidino group or 4-methylpiperazino group,
Claim 17
Dependent Claim
17 words
The compound of Claim 1, wherein W 1 is the group and W 2 is the group.
Claim 18
Dependent Claim
127 words
The compound of Claim 16 of the formula (IV): wherein Y is a C 1-4 alkylene group or propylene group having a C 1-4 alkyl group substituent; R 1 and R 2 each independently is a C 1-4 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom; Z is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; and R3 and R4 each independently is a C 1-4 alkyl group and R 3 , R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom.
Claim 19
Dependent Claim
69 words
The compound of Claim 17, wherein Y is ethylene group, n - propylene group, 3-methylpropylene group or 3-(2-methylpropyl)propylene group; is dimethylamino group, diethylamino group, di-n-propylamino group, di-n-butylamino group, pyrrolidino group, piperidino group, homopieridino group or piperazino group; Z is ethylene group, n-propylene group, n-hexylene group, 3-methylpropylene group or 3-(2-methylpropyl)propylene group; and is dimethylamino group, diethylamino group, di-n-propylamino group, di-n-butylamino group, pyrrolidino group, piperidino group, homopiperidino group or piperazino group.
Claim 20
Dependent Claim
38 words
The compound of Claim 17, wherein Y is n-propylene group; is diethylamino group or piperidino group; Z is n-propylene group, n-hexylene group or 3-methylpropylene group; and is dimethylamino group, diethylamino group, di-n-propylamino group, di-n-butylamino group or piperidino group.
Claim 21
Dependent Claim
34 words
The compound of Claim 17, wherein Y is 3-methylpropylene group; is dimethylamino group or piperidino group; Z is n-propylene group, 3-methylpropylene group or 3-(2-methylpropyl)propylene group; and is dimethylamino group, diethylamino group or piperidino group.
Claim 22
Dependent Claim
134 words
A process for preparing the compound of Claim 3 of the formula (II) which comprises reacting 3-aminoindazole with a ω-halogenoalkylamine of the general formula (V): wherein Z, R 3 and R 4 have a meaning according to Claim 1 or Z is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; R 3 and R 4 each independently is a C 1-6 alkyl group and R 3 , R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom; and X is a chlorine atom, a bromine atom or an iodine atom.
Claim 23
Dependent Claim
24 words
The process of Claim 21, wherein the amount of the compound of the formula (V) is about 1 mol per mol of the 3-aminoindazole.
Claim 24
Dependent Claim
18 words
The process of Claim 21, wherein the reaction is carried out in the presence of an acid acceptor.
Claim 25
Dependent Claim
18 words
The process of Claim 23, wherein the acid acceptor Asahi-P08098lEU is tertiary amine or an alkali metal compound.
Claim 26
Dependent Claim
25 words
2 5 - The process of Claim 24, wherein the alkali metal compound is a carbonate, a bicarbonate or a hydroxide of an alkali metal.
Claim 27
Dependent Claim
21 words
The process of Claim 23, wherein the amount of the acid acceptor is about 2 mol per mol of the 3-aminoindazole.
Claim 28
Dependent Claim
18 words
The process of Claim 21, wherein the reaction is carried out in the presence of a reaction medium.
Claim 29
Dependent Claim
40 words
The process of Claim 27, wherein the reaction medium is a non-proton polar solvent such as acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, an alcohol such as methyl alcohol, ethyl alcohol, propyl alcohol, or a glycol such as ethylene glycol or propylene glycol.
Claim 30
Dependent Claim
15 words
The process of Claim 21, wherein the reaction temperature is about 10°C to about 200°C.
Claim 31
Dependent Claim
155 words
A process for preparing the compound of Claim 10 of the formula (III) which comprises reacting 3-aminoindazole with phthalic anhydride to obtain 3-phthalimidoindazole, reacting the 3-phthalimidoindazole with an ω-halogenoalkylamine of the formula (VIII): wherein Y, R 1 and R 2 have a meaning according to Claim 1 or Y is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; R 1 and R 2 each independently is a C 1-6 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and the C 4-6 heterocyclic rings may have at least one methyl group, hydroxyl group, chlorine atom, bromine atom or iodine atom; and X is a chlorine atom, a bromine atom or an iodine atom; to give a l-(aminoalkyl)-3-phthalimidoindazole, and then treating the l-(aminoalkyl)-3-phthalimidoindazole with hydrazine hydrate. Asahi-P08098lEU
Claim 32
Dependent Claim
25 words
The process of Claim 30, wherein the reaction between the 3-aminoindazole and the phthalic anhydride is carried out in the presence of a reaction medium.
Claim 33
Dependent Claim
29 words
The process of Claim 31, wherein the reaction medium is a polar organic solvent such as dioxane, diethyl ether, tetrahydrofuran, ethyl alcohol, ethylene glycol, acetonitrile, dimethyl sulfoxide or N,N-dimethylformamide.
Claim 34
Dependent Claim
15 words
The process of Claim 31, wherein the reaction temperature is about 10°C to about 200°C.
Claim 35
Dependent Claim
28 words
The process of Claim 30, wherein the reaction between the 3-phthalimidoindazole and the compound of the formula (VIII) is carried out in the presence of a reaction medium.
Claim 36
Dependent Claim
40 words
The process of Claim 34, wherein the reaction medium is a non-proton polar solvent such as acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, an alcohol such as methyl alcohol, ethyl alcohol, propyl alcohol, or a glycol such as ethylene glycol or propylene glycol.
Claim 37
Dependent Claim
18 words
The process of Claim 34, wherein the reaction is carried out in the presence of an acid acceptor.
Claim 38
Dependent Claim
18 words
The process of Claim 36, wherein the acid acceptor is a tertiary amine or an alkali metal compound.
Claim 39
Dependent Claim
21 words
The process of Claim 37, wherein'the alkali metal compound is a carbonate, a bicarbonate or a hydroxide of an alkali metal.
Claim 40
Dependent Claim
21 words
The process of Claim 36, wherein the amount of the acid acceptor is about 2 mol per mol of the 3-phthalimidoindazole.
Claim 41
Dependent Claim
16 words
The process of Claim 34, wherein the reaction temperature is about 10°C to about 200 °C.
Claim 42
Dependent Claim
24 words
The process of Claim 30, wherein the reaction between the 1-(aminoalkyl)-3-phthalimidoindazole and hydrazine hydrate is carried out in the presence of a reaction medium.
Claim 43
Dependent Claim
29 words
The process of Claim 41, wherein the reaction medium is an alcohol such as methyl alcohol, ethyl alcohol, a glycol such as ethylene glycol, propylene glycol, diglyme or triethanolamine.
Claim 44
Dependent Claim
15 words
The process of Claim 41, wherein the reaction is carried out under cooling with ice.
Claim 45
Dependent Claim
198 words
A process for preparing the compound of Claim 17 of the formula (IV) which comprises reacting an 1-aminoalkyl-3-aminoindazole of the formula (III): wherein Y, R 1 and R 2 have a meaning according to Claim 1 or Y is a C 1-4 alkylene group or propylene group having a C 1-4 alkyl group substituent; and R 1 and R 2 each independently is a C 1-4 alkyl group and R 1 , R 2 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom with a ω-halogenoalkylamine or the formula (V): wherein Z, R 3 and R 4 have a meaning according to Claim 1 or Z is a C 1-6 alkylene group or propylene group having a C 1-4 alkyl group substituent; R 3 and R 4 each independently is a C 1-4 alkyl group and R 3 , R 4 and the adjacent nitrogen atom may form a C 4-6 heterocyclic ring or a C 4-6 heterocyclic ring containing an additional nitrogen atom and X is a chlorine atom, a bromine atom or an iodine atom; in the presence of an acid acceptor.
Claim 46
Dependent Claim
28 words
The process of Claim 44, wherein the amount of the compound of the formula (V) is about 1 mol per mol of the compound of the formula (III).
Claim 47
Dependent Claim
18 words
The process of Claim 44, wherein the acid acceptor is a tertiary amine or an alkali metal compound.
Claim 48
Dependent Claim
22 words
The process of Claim 46, wherein the alkali metal compound is a carbonate, a bicarbonate or a hydroxide of an alkali metal.
Claim 49
Dependent Claim
25 words
The process of Claim 44, wherein the amount of the acid acceptor is about 2 mol per mol of the compound of the formula (III).
Claim 50
Dependent Claim
18 words
The process of Claim 44, wherein the reaction is carried out in the presence of a reaction medium.
Claim 51
Dependent Claim
40 words
The process of Claim 49, wherein the reaction medium is a non-proton polar solvent such as acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, an alcohol such as methyl alcohol, ethyl alcohol, propyl alcohol, or a glycol such as ethylene glycol or propylene glycol.
Claim 52
Dependent Claim
17 words
The process of Claim 44, wherein the reaction temperature is about 10°C to about 200 0 C.
Claim 53
Dependent Claim
26 words
A therapeutical agent, characterized by a compound of formula I, II, II or IV according to Claims 1 to 20 as active ingredient and usual excipients.
Claim 54
Dependent Claim
8 words
Anti-inflammatory and analgesic agent according to Claim 52.
Claim 55
Dependent Claim
44 words
Original page 80, line 2 = page 94, line 20: "I,II,II,IV" should be corrected to "I,II,III,IV " ; attention is drawn to the fact that claim 52 in question refers to claims 1 to 20 including claims 10 to 16 directed to compound III.
Claim 56
Dependent Claim
17 words
Pages 13 and 45 of December 7, 1981 should be replaced by new pages 13 and 45.
Claim 57
Dependent Claim
17 words
Pages 13 and 45 of December 7, 1981 should be replaced by new pages 13 and 45.
Claim 58
Dependent Claim
31 words
II. Auxiliary reouest. You are kindly requested to replace pages 13, 21, 28, 29, 34, 45, 45 and 94 by new pages 13, 21, 28, 29, 34, 45, 46 and 94.
Claim 59
Dependent Claim
31 words
II. Auxiliary reouest. You are kindly requested to replace pages 13, 21, 28, 29, 34, 45, 45 and 94 by new pages 13, 21, 28, 29, 34, 45, 46 and 94.
Claim 60
Dependent Claim
11 words
I. Main request. You are kindly requested to act as follows:
Claim 61
Dependent Claim
11 words
I. Main request. You are kindly requested to act as follows:
Claim 62
Dependent Claim
24 words
Original page 19, line 2 = page 21, line 21, of December 7, 1981: "at the temperature" should be corrected to "at a temperature".
Claim 63
Dependent Claim
24 words
Original page 19, line 2 = page 21, line 21, of December 7, 1981: "at the temperature" should be corrected to "at a temperature".
Claim 64
Dependent Claim
20 words
Original page 25, line 27 = page 28, line 25, of December 7, 1981: "inflammatory" should be corrected to "inflammation".
Claim 65
Dependent Claim
20 words
Original page 25, line 27 = page 28, line 25, of December 7, 1981: "inflammatory" should be corrected to "inflammation".
Claim 66
Dependent Claim
20 words
Original page 26, line 24 = page 29, line 20, of December 7, 1981: "according" should be corrected to "accordance".
Claim 67
Dependent Claim
20 words
Original page 26, line 24 = page 29, line 20, of December 7, 1981: "according" should be corrected to "accordance".
Claim 68
Dependent Claim
26 words
Original page 31, lines 24 to 25 = page 34, line 37, of December 7, 1981: "was not occurred" should be corrected to "did not occur".
Claim 69
Dependent Claim
26 words
Original page 31, lines 24 to 25 = page 34, line 37, of December 7, 1981: "was not occurred" should be corrected to "did not occur".
Claim 70
Dependent Claim
28 words
Original page 40, line 10 = page 46, line 22, of December 7, 1981: "almina-column" should be corrected to "alumina-column"; cf. original page 39, line 5 (for example).
Claim 71
Dependent Claim
28 words
Original page 40, line 10 = page 46, line 22, of December 7, 1981: "almina-column" should be corrected to "alumina-column"; cf. original page 39, line 5 (for example).
References Cited (Backward Citations)
GB1411938A
Cited
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