US 2003/0149020 A1Published application

New compounds

AssigneeBiovitrum AB

InventorsUlf Bremberg, Patrizia Caldirola, Annika J. Jensen, Gary Johansson, Andrew Mott, Lori Sutin, Jan Tejbrant

Life of this patent

Estimating the term…

Abstract

The present invention relates to substituted bis-arylsulfonamide and arylsulfonamide compounds of the general formula (I) or the formula (II), which compounds are potentially useful for the prophylaxis and treatment of medical conditions relating to obesity, type II diabetes and/or disorders of the central nervous system. 1

Claims22

Dependent claims

A compound of the formula (I)

273
or a pharmaceutically acceptable salt thereof, wherein
X is
274
R1 and R3 are independently
(a) H
(b) C1-6 alkyl,
(c) C1-6 alkoxy,
(d) straight or branched C1-6 hydroxyalkyl,
(e) straight or branched C1-6 alkylhalides;
or
(f) a group Ar;
Ar is
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or
(g) a bicyclic ring system consisting of two heterocyclic rings as defined under (f), or a bicyclic ring system consisting of one benzene ring and one heterocyclic ring as defined under (f);
alternatively, R1 and R3 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 (Ib);
optionally, the group Ar is substituted with
(a) Y, or
(b) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
Y is
(a) H,
(b) halogen,
(c) C1-6 alkyl,
(d) CF3,
(e) hydroxy,
(f) C1-6 alkoxy,
(g) C1-4 alkenyl;
(h) phenyl;
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) OCF3,
(m) CN,
(n) straight or branched C1-6 hydroxyalkyl,
(o) straight or branched C1-6 alkylhalides,
(p) NH2,
(q) NHR6,
(r) NR6R7,
(s) NO2,
(t) —CONR6R7,
(u) NHSO2R6,
(v) NR6COR7,
(x) SO2NRR7,
(z) —C(═O)R6,
(aa) —CO2R6, or
(ab) S(O)NR6;
wherein n is 0, 1, 2 or 3;
R2 and R4 are independently:
(a) —SO2R1,
(b) H,
(c) C1-6 alkyl,
(d) C1-C3 alkenyl,
(e) C1-C3 alkylaryl,
(f) Ar as defined above for R1,
(g) —C(═O)R6,
(h) —C(O)NR6R7,
(i) —C(S)NR6R7,
9t) —CO2R6;
(k) —C(S)R;
(l) straight or branched C1-6 hydroxyalkyl, or
(m) straight or branched C1-6 alkylhalides;
alternatively, R2 and R4 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 in formula (Ia);
R5 is selected from the group consisting of the following chemical groups:
275
R6 and R7 are independently
(a) H,
(b) C1-6 alkyl,
(c) C3-7 cycloalkyl, or
(d) Ar, as defined above for R1;
alternatively, R6 and R7 are linked to form a group (CH2)2O, (CH2)4O or (CH2)3-5;
R8 is
(a) H, or
(b) C1-6 alkyl.

75 more elements

A compound of the formula (II)

278
or a pharmaceutically acceptable salt thereof, wherein
RK9, R2 and R4 are H;
or
two of R9, R12 and R14 are H;
and the remaining of R9, R12 and R14 is
(a) —NH2,
(b) —NHR6,
(c) NR6R7,
(d) —N(CO)R6,
(e) —N(CS)R6, or
(f)-NO2;
R10 is a group R3;
R11 is a group R1;
in which each of R1 and R3, independently, is:
(a) H
(b) C1-6alkyl,
(c) C1-6alkoxy,
(d) straight or branched C1-6 hydroxyalkyl,
(e) straight or branched C1-6 alkylhalides;
or
(f) a group Ar;
Ar is
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or
(g) a bicyclic ring system consisting of two heterocyclic rings as defined under (f), or a bicyclic ring system consisting of one benzene ring and one heterocyclic ring as defined under (f);
alternatively, R1 and R3 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 in formula (Ib);
optionally, the group Ar is substituted with
(a) Y, or
(b) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
Y is
(a) H,
(b) halogen,
(c) C1-6 alkyl,
(d) CF3,
(e) hydroxy,
(f) C1-6 alkoxy,
(g) C1-4 alkenyl;
(h) phenyl;
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) OCF3,
(m) CN,
(n) straight or branched C1-6 hydroxyalkyl,
(o) straight or branched C1-6 alkylhalides,
(P) NH2,
(q) NHR6,
(r) NR6R7,
(s) NO2,
(t) —CONR6R7,
(u) NHSO2R6,
(v) NR6COR7,
(x) SO2NR6R7,
(z) C(═O)R6,
(aa) —CO2R6, or
(ab) S(O)nR6;
wherein n is 0, 1, 2 or 3;
R13 is
(a) homopiperazine,
(b) methylhomopiperazine, or
(c) a group R5;
and
R5 is selected from the group consisting of the following chemical groups:
279
R6 and R7 are independently
(a) H,
(b) C1-6 alkyl,
(C) C3-7 cycloalkyl, or
(d) Ar, as defined above for R1;
alternatively, R6 and R7 are linked to form a group (CH2)2O, (CH2)4O or (CH2)3-5;
R8 is
(a) H, or
(b) C1-6 alkyl.

75 more elements

A compound of the formula (I)

281
or a pharmaceutically acceptable salt thereof, wherein
X is
282
R1 and R3 are independently
(a) H
(b) C1-6 alkyl,
(c) C1 6 alkoxy,
(d) straight or branched C1-6 hydroxyalkyl,
(e) straight or branched C1-6 alkylhalides;
or
(f) a group Ar;
Ar is
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, aromatic, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or
(g) a bicyclic ring system consisting of two heterocyclic rings as defined under (f), or a bicyclic ring system consisting of one benzene ring and one heterocyclic ring as defined under (f);
alternatively, R1 and R3 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 (Ib);
optionally, the group Ar is substituted with
(a) Y, or
(b) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
Y is
(a) H,
(b) halogen,
(c) C1-6 alkyl,
(d) CF3,
(e) hydroxy,
(f) C1-6 alkoxy,
(g) C1-4 alkenyl;
(h) phenyl;
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) OCF3,
(m) CN,
(n) straight or branched C1-6 hydroxyalkyl,
(o) straight or branched C1-6 alkylhalides,
(p) NH2,
(q) NHR6,
(r) NR6R7,
(s) NO2,
(t) —CONR6R7,
(u) NHSO2R6,
(v) NR6COR7,
(x) SO2NR6R7,
(z) —C(═O)R6,
(aa) —CO2R6, or
(ab) S(O)nR6;
wherein n is 0, 1, 2 or 3;
R2 and R4 are independently:
(a) —SO2R1,
(b) H,
(C) C1-6 alkyl,
(d) C1-C3 alkenyl,
(e) C1-C3 alkylaryl,
(f) Ar as defined above for R1,
(g) —C(═O)R6,
(h) —C(O)NR6R7,
(i) —C(S)NR6R7,
(j) —CO2R6;
(k) —C(S)R6;
(l) straight or branched C1-6 hydroxyalkyl, or
(m) straight or branched C1-6 alkylhalides;
alternatively, R2 and R4 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 in formula (Ia);
R5 is selected from the group consisting of the following chemical groups:
283
R6 and R7 are independently
(a) H,
(b) C1-6 alkyl,
(c) C3-7 cycloalkyl, or
(d) Ar, as defined above for R1;
alternatively, R6 and R7 are linked to form a group (CH2)2O, (CH2)4O or (CH2)3-5;
R8 is
(a) H, or
(b) C1-6 alkyl.

75 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/144,677Filed 13 May 2002
Priority: SE 0101659-111 May 2001
Published: 7 Aug 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07D 261/10
Having two or more double bonds between ring members or between ring members and non-ring members: with hetero atoms or with carbon atoms having…
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 25/00
Drugs for disorders of the nervous system

Family

Application60/294,102Us provisional application · filed 29 May 2001
Application60/294,132Us provisional application · filed 29 May 2001
US 6,969,710 B2Related patent
US 2003/0149020 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of the formula (I)

273
or a pharmaceutically acceptable salt thereof, wherein
X is
274
R1 and R3 are independently
(a) H
(b) C1-6 alkyl,
(c) C1-6 alkoxy,
(d) straight or branched C1-6 hydroxyalkyl,
(e) straight or branched C1-6 alkylhalides;
or
(f) a group Ar;
Ar is
(a) phenyl,
(b) 1-naphthyl,
(c) 2-naphthyl,
(d) benzyl,
(e) cinnamoyl,
(f) a 5 to 7-membered, partially or completely saturated, heterocyclic ring containing 1 to 4 heteroatoms, selected from oxygen, nitrogen and sulfur, or
(g) a bicyclic ring system consisting of two heterocyclic rings as defined under (f), or a bicyclic ring system consisting of one benzene ring and one heterocyclic ring as defined under (f);
alternatively, R1 and R3 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 (Ib);
optionally, the group Ar is substituted with
(a) Y, or
(b) a 5 to 7-membered, partially or completely saturated, heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur;
Y is
(a) H,
(b) halogen,
(c) C1-6 alkyl,
(d) CF3,
(e) hydroxy,
(f) C1-6 alkoxy,
(g) C1-4 alkenyl;
(h) phenyl;
(i) phenoxy,
(j) benzyloxy,
(k) benzoyl,
(l) OCF3,
(m) CN,
(n) straight or branched C1-6 hydroxyalkyl,
(o) straight or branched C1-6 alkylhalides,
(p) NH2,
(q) NHR6,
(r) NR6R7,
(s) NO2,
(t) —CONR6R7,
(u) NHSO2R6,
(v) NR6COR7,
(x) SO2NRR7,
(z) —C(═O)R6,
(aa) —CO2R6, or
(ab) S(O)NR6;
wherein n is 0, 1, 2 or 3;
R2 and R4 are independently:
(a) —SO2R1,
(b) H,
(c) C1-6 alkyl,
(d) C1-C3 alkenyl,
(e) C1-C3 alkylaryl,
(f) Ar as defined above for R1,
(g) —C(═O)R6,
(h) —C(O)NR6R7,
(i) —C(S)NR6R7,
9t) —CO2R6;
(k) —C(S)R;
(l) straight or branched C1-6 hydroxyalkyl, or
(m) straight or branched C1-6 alkylhalides;
alternatively, R2 and R4 are linked to form a group (CH2)2O, (CH2)4O, or (CH2)3-5 in formula (Ia);
R5 is selected from the group consisting of the following chemical groups:
275
R6 and R7 are independently
(a) H,
(b) C1-6 alkyl,
(c) C3-7 cycloalkyl, or
(d) Ar, as defined above for R1;
alternatively, R6 and R7 are linked to form a group (CH2)2O, (CH2)4O or (CH2)3-5;
R8 is
(a) H, or
(b) C1-6 alkyl.

75 more elements

Facts

Application

10/144,677Filed 13 May 2002

Priority

SE 0101659-111 May 2001

Published

7 Aug 2003

Term ends

Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07D 261/10
Having two or more double bonds between ring members or between ring members and non-ring members: with hetero atoms or with carbon atoms having…
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 25/00
Drugs for disorders of the nervous system