# US 10,118,930 B2 · Piperidinylpyrazolopyrimidinones and their use

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- Number: US 10,118,930 B2
- Document ID: US10118930B2
- Status: Granted
- Kind: B2
- Application number: 15/523,954
- Filed: 2015-10-30
- Published: 2017-11-23
- Granted: 2018-11-06
- Earliest claimed: 2015-04-30
- Assignees: Bayer Pharma Aktiengesellschaft
- Applicants: Bayer Pharma Aktiengesellschaft
- Inventors: Manuel Ellermann; Gaelle Valot; Yolanda Cancho Grande; Jorma Haßfeld; Tom Kinzel; Johannes Köbberling; Kristin Beyer; Susanne Röhrig; Michael Sperzel; Jan Stampfuß; Imke Meyer; Maria Köllnberger; Nils Burkhardt; Karl-Heinz Schlemmer; Christian Stegmann; Joachim Schuhmacher; Matthias Werner; Jörg Heiermann; Willem Jan Hengeveld
- Web page: https://patentgrep.com/patent/US10118930B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 211/06: having no double bonds between ring members or between ring members and non-ring members
- C07D 231/00: Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D 247/02: having the nitrogen atoms in positions 1 and 3
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 271/10: 1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D 403/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present application relates to novel substituted piperidinylpyrazolopyrimidinones, to processes for their preparation, the compounds for use alone or in combinations in a method for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of acute and recurrent bleeding in patients with or without underlying hereditary or acquired hemostatic disorders, wherein the bleeding is associated with a disease or medical intervention selected from the group consisting of heavy menstrual bleeding, postpartum hemorrhage, hemorrhagic shock, hemorrhagic cystitis, gastrointestinal hemorrhage, trauma, surgery, transplantation, stroke, liver diseases, hereditary angioedema, nosebleed, and synovitis and cartilage damage following hemarthrosis.

## Claims

### Claim 1

Compound of formula (I-A)
in which
R1 is selected from the group consisting of hydrogen and C1-C5 alkyl;
R2 is selected from the group consisting of hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, carboxyl, C1-C4 alkylester, C1-C4 alkoxy-C1-C4 alkyl, halogen, methylsulfanyl, phenyl, the phenyl being optionally substituted with halogen, and 5 membered heteroaryl;
R3 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, the alkyl being optionally substituted with di-C1-C4 alkylamino, C1-C4 alkenyl, C1-C4 alkylester, the C1-C4 alkylester being optionally substituted with one, two, three, four, or five halogen substituents, C3-C4 cycloalkylester, C3-C4 cycloalkyl, carboxyl, carboxamide, benzylester, —NH—CO-phenyl, —CS—NH2,
phenylsulfonyl, the phenylsulfonyl being optionally substituted with one, two, or three halogen substituents,
phenyl,
the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of halogen and C1-C4 alkoxy, where two adjacent methoxy groups may optionally form a dioxane ring,
or the phenyl being optionally substituted with one or two substituents selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, benzyloxy, methylsulfonyl, and phenyl, the phenyl being optionally substituted with C1-C4 haloalkyl,
5-6 membered heterocyclyl-C1-C4 alkyl, the 5-6 membered heterocyclyl-moiety being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl and oxo,
5-6 membered heteroaryl,
the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C1-C6 haloalkyl, C1-C4 aminoalkyl, C1-C4 alkylester, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy-C1-C4 alkyl, cyano, hydroxyl, carboxyl, C1-C4 alkyl-SO2—C1-C4 alkyl, and —CO—NH2,
or the 5-6 membered heteroaryl being optionally substituted with one C3-C6 cycloalkyl substituent, the C3-C6 cycloalkyl optionally being substituted with one, two, or three halogen or methyl substituents, or with phenyl, the phenyl being optionally substituted with C1-C4 alkoxy or halogen,
or the 5-6 membered heteroaryl being optionally substituted with one substituent selected from the group consisting of fused or bridged C5-C12 bi- or tricycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkyl-C1-C4 alkenyl,
phenyl, the phenyl optionally being substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4-alkylester, nitro, amino, di-C1-C4 alkylamine, and cyano,
phenyl-C1-C4 alkyl,
the phenyl moiety optionally being substituted with one, two, or three substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, and hydroxyl,
the alkyl moiety optionally being substituted with one or two substituents selected from the group consisting of C1-C4 alkyl and hydroxyl,
5-6 membered heterocycloalkyl, the 5-6 membered heterocycloalkyl being optionally substituted with C3-C6 cycloalkyl or C1-C4 alkyl,
5-6 membered heterocycloalkyl-C1-C4 alkyl,
the 5-6 membered heterocycloalkyl moiety being optionally substituted with C1-C4 alkyl or oxo,
the C1-C4 alkyl moiety being optionally substituted with C1-C4 alkyl,
5-6 membered heteroaryl, the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of halogen, C1-C4 alkyl, and C1-C4 haloalkyl,
and 5-6 membered heteroaryl-C1-C4 alkyl,
the 5-6 membered heteroaryl-moiety being optionally substituted with one or two substituents selected from the group consisting of C1-C4 alkoxy and C1-C4 alkyl,
the C1-C4 alkyl-moiety being optionally substituted with one or two methyl substituents,
—CO—R4, with R4 being selected from the group consisting of C1-C4 alkyl, wherein the C1-C4 alkyl is optionally substituted with one or two methyl, and C3-C6 cycloalkyl,
—CO—N(R5R7), with
R5 being selected from the group consisting of hydrogen and C1-C4 alkyl,
R7 being selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4-alkoxy-C1-C4 alkyl, amino-oxo-C1-C4 alkyl, naphthyl,
C3-C6 cycloalkyl, the C3-C6 cycloalkyl being optionally substituted with one or two C1-C4 alkyl substituents,
C3-C6 cycloalkyl-C1-C4 alkyl,
5-6 membered heterocyclyl,
oxazolidinyl-C1-C4 alkyl,
benzyl,
the phenyl moiety of the benzyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
the methyl moiety of the benzyl optionally being substituted with C1-C4 alkyl,
benzyl-C3-C6 cycloalkyl,
imidazolyl-C1-C4 alkyl, the imidazolyl-C1-C4 alkyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
oxazolyl-C1-C4 alkyl, the oxazolyl-C1-C4 alkyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
oxazolidinone-C1-C4 alkyl,
pyridinyl-C1-C4 alkyl,
and phenyl, the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, halogen, and C1-C4 alkoxy,
or —N(R5R7) being selected from the group consisting of 5-7 membered cyclic amines which contain one or two ring nitrogen atoms, zero or one ring oxygen atom, and zero or one ring sulfur atom, and are attached via a ring nitrogen atom, the 5 to 7 membered cyclic amines being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkyl, oxo, hydroxyl, halogen, and C1-C4 alkyl,
or —N(R5R7) being selected from the group consisting of two annelated, aromatic, partially saturated or saturated rings which are each 5-7 membered and each contain one or two ring nitrogen atoms and are attached via a ring nitrogen atom,
and —N(R5R7) being selected from the group consisting of bicyclic azaspiro compounds, the azaspiro compounds being optionally substituted with oxo;
or R2 and R3 together form a C5-C6 cycloalkyl ring;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 2

Compound of formula (I-B)
in which
R1 is selected from the group consisting of hydrogen, and C1-C5 alkyl;
R2 is selected from the group consisting of hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, carboxyl, C1-C4 alkylester, C1-C4 alkoxy-C1-C4 alkyl, halogen, methylsulfanyl, phenyl, the phenyl being optionally substituted with halogen, and 5 membered heteroaryl;
R3 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4 alkyl, the alkyl being optionally substituted with di-C1-C4 alkylamino, C1-C4 alkenyl, C1-C4 alkylester, the C1-C4 alkylester being optionally substituted with one, two, three, four, or five halogen substituents, C3-C4 cycloalkylester, C3-C4 cycloalkyl, carboxyl, carboxamide, benzylester, —NH—CO-phenyl, —CS—NH2,
phenylsulfonyl, the phenylsulfonyl being optionally substituted with one, two, or three halogen substituents,
phenyl,
the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of halogen and C1-C4 alkoxy, where two adjacent methoxy groups may optionally form a dioxane ring,
or the phenyl being optionally substituted with one or two substituents selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, cyano, benzyloxy, methylsulfonyl, and phenyl, the phenyl being optionally substituted with C1-C4 haloalkyl,
5-6 membered heterocyclyl-C1-C4 alkyl, the 5-6 membered heterocyclyl-moiety being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl and oxo,
5-6 membered heteroaryl,
the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C1-C6 haloalkyl, C1-C4 aminoalkyl, C1-C4 alkylester, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy-C1-C4 alkyl, cyano, hydroxyl, carboxyl, C1-C4 alkyl-SO2—C1-C4 alkyl, and —CO—NH2,
or the 5-6 membered heteroaryl being optionally substituted with one C3-C6 cycloalkyl substituent, the C3-C6 cycloalkyl optionally being substituted with one, two, or three halogen or methyl substituents, or with phenyl, the phenyl being optionally substituted with C1-C4 alkoxy or halogen,
or the 5-6 membered heteroaryl being optionally substituted with one substituent selected from the group consisting of fused or bridged C5-C12 bi- or tricycloalkyl, C3-C6 cycloalkyl-C1-C4 alkyl, C3-C6 cycloalkyl-C1-C4 alkenyl, phenyl, the phenyl optionally being substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4-alkylester, nitro, amino, di-C1-C4 alkylamine, and cyano,
phenyl-C1-C4 alkyl,
the phenyl moiety optionally being substituted with one, two, or three substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, and hydroxyl,
the alkyl moiety optionally being substituted with one or two substituents selected from the group consisting of C1-C4 alkyl and hydroxyl,
5-6 membered heterocycloalkyl, the 5-6 membered heterocycloalkyl being optionally substituted with C3-C6 cycloalkyl or C1-C4 alkyl,
5-6 membered heterocycloalkyl-C1-C4 alkyl,
the 5-6 membered heterocycloalkyl moiety being optionally substituted with C1-C4 alkyl or oxo,
the C1-C4 alkyl moiety being optionally substituted with C1-C4 alkyl,
5-6 membered heteroaryl, the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of halogen, C1-C4 alkyl, and C1-C4 haloalkyl,
and 5-6 membered heteroaryl-C1-C4 alkyl,
the 5-6 membered heteroaryl-moiety being optionally substituted with one or two substituents selected from the group consisting of C1-C4 alkoxy and C1-C4 alkyl,
the C1-C4 alkyl-moiety being optionally substituted with one or two methyl substituents,
—CO—R4, with R4 being selected from the group consisting of C1-C4 alkyl, wherein the C1-C4 alkyl is optionally substituted with one or two methyl, and C3-C6 cycloalkyl,
—CO—N(R5R7), with
R5 being selected from the group consisting of hydrogen and C1-C4 alkyl,
R7 being selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4-alkoxy-C1-C4 alkyl, amino-oxo-C1-C4 alkyl, naphthyl,
C3-C6 cycloalkyl, the C3-C6 cycloalkyl being optionally substituted with one or two C1-C4 alkyl substituents,
C3-C6 cycloalkyl-C1-C4 alkyl,
5-6 membered heterocyclyl,
oxazolidinyl-C1-C4 alkyl,
benzyl,
the phenyl moiety of the benzyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
the methyl moiety of the benzyl optionally being substituted with C1-C4 alkyl,
benzyl-C3-C6 cycloalkyl,
imidazolyl-C1-C4 alkyl, the imidazolyl-C1-C4 alkyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
oxazolyl-C1-C4 alkyl, the oxazolyl-C1-C4 alkyl being optionally substituted with one, two, or three C1-C4 alkyl substituents,
oxazolidinone-C1-C4 alkyl,
pyridinyl-C1-C4 alkyl,
and phenyl, the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, halogen, and C1-C4 alkoxy,
or —N(R5R7) being selected from the group consisting of 5-7 membered cyclic amines which contain one or two ring nitrogen atoms, zero or one ring oxygen atom, and zero or one ring sulfur atom, and are attached via a ring nitrogen atom, the 5 to 7 membered cyclic amines being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkyl, oxo, hydroxyl, halogen, and C1-C4 alkyl,
or —N(R5R7) being selected from the group consisting of two annelated, aromatic, partially saturated or saturated rings which are each 5-7 membered and each contain one or two ring nitrogen atoms and are attached via a ring nitrogen atom,
and —N(R5R7) being selected from the group consisting of bicyclic azaspiro compounds, the azaspiro compounds being optionally substituted with oxo;
or R2 and R3 together form a C5-C6 cycloalkyl ring;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 3 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is selected from the group consisting of hydrogen and C1-C5 alkyl;
R2 is selected from the group consisting of hydrogen, C1-C2 alkyl, C3-C4 cycloalkyl, C1-C2 haloalkyl, carboxyl, C1-C2 alkylester, C1-C2 alkoxy-C1-C2 alkyl, halogen, methylsulfanyl, phenyl, the phenyl being optionally substituted with a substituent selected from the group consisting of fluorine and chlorine, and 5-6 membered heteroaryl;
R3 is selected from the group consisting of hydrogen, bromine, chlorine, cyano, methyl, the methyl being optionally substituted with di-C1-C4 alkylamino, ethyl, C1-C4 alkenyl, C1-C4 alkylester, the C1-C4 alkylester being optionally substituted with one, two, or three fluorine substituents, C3-C4 cycloalkylester, C3-C4 cycloalkyl, carboxyl, carboxamide, benzylester, —NH—CO-phenyl, —CS—NH2,
phenylsulfonyl, the phenylsulfonyl being optionally substituted with one or two substituents selected from the group consisting of chlorine and fluorine,
phenyl,
the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of bromine, chlorine, fluorine, ethoxy, and methoxy, where two adjacent methoxy groups may optionally form a dioxane ring,
or the phenyl being optionally substituted with one or two substituents selected from the group consisting of C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 fluoroalkoxy, and cyano,
or the phenyl being optionally substituted with one substituent selected from the group consisting of benzyloxy, methylsulfonyl, and phenyl, the phenyl being optionally substituted with C1-C2 fluoroalkyl,
5-6 membered heterocyclyl-C1-C2 alkyl, the 5-6 membered heterocyclyl-moiety being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C2 alkyl and oxo,
5-6 membered heteroaryl,
the 5-6 membered heteroaryl being optionally substituted with one or two substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C1-C4 haloalkyl, C1-C2 aminoalkyl, C1-C2 alkylester, C1-C2 alkoxy, C1-C2 haloalkoxy, C1-C2 alkoxy-C1-C4 alkyl, cyano, hydroxyl, carboxyl, C1-C2 alkyl-SO2—C1-C2 alkyl, and —CO—NH2,
or the 5-6 membered heteroaryl being optionally substituted with one C3-C6 cycloalkyl substituent, the C3-C6 cycloalkyl optionally being substituted with one, two, or three chlorine, fluorine, or methyl substituents, or with phenyl, the phenyl being optionally substituted with C1-C2 alkoxy, chlorine, or fluorine,
bridged bi- or tricycloalkyl C3-C6 cycloalkyl-C1-C2 alkyl, C3-C6 cycloalkyl-C1-C4 alkenyl,
phenyl, the phenyl optionally being substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, chlorine, fluorine, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, C1-C2-alkylester, nitro, amino, di-C1-C2 alkylamino, and cyano,
phenyl-C1-C2 alkyl,
the phenyl moiety optionally being substituted with one, two, or three substituents selected from the group consisting of fluorine, chlorine, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, and hydroxyl,
the alkyl moiety optionally being substituted with one or two substituents selected from the group consisting of C1-C2 alkyl and hydroxyl,
5-6 membered heterocycloalkyl, the 5-6 membered heterocycloalkyl being optionally substituted with C3-C5 cycloalkyl or C1-C3 alkyl,
5-6 membered heterocycloalkyl-C1-C2 alkyl,
the 5-6 membered heterocycloalkyl moiety being optionally substituted with C1-C2 alkyl or oxo,
the C1-C2 alkyl moiety being optionally substituted with C1-C2 alkyl,
5-6 membered heteroaryl, the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of fluorine, chlorine, C1-C3 alkyl, and C1-C2 fluoroalkyl,
and 5-6 membered heteroaryl-C1-C4 alkyl,
the 5-6 membered heteroaryl-moiety being optionally substituted with one or two substituents selected from the group consisting of C1-C2 alkoxy and C1-C2 alkyl,
the C1-C2 alkyl-moiety being optionally substituted with one or two methyl substituents,
CO—R4, with R4 being selected from the group consisting of C1-C4 alkyl, wherein the C1-C4 alkyl is optionally substituted with one or two methyl substituents, and C3-C6 cycloalkyl,
and CO—N(R5R7), with
R5 being selected from the group consisting of hydrogen and C1-C4 alkyl,
R7 being selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, C1-C2-alkoxy-C1-C4 alkyl, amino-oxo-C1-C4 alkyl, naphthyl,
C3-C6 cycloalkyl, the C3-C6 cycloalkyl being optionally substituted with one or two C1-C2 alkyl substituents,
C3-C6 cycloalkyl-C1-C2 alkyl,
5-6 membered heterocyclyl,
oxazolidinyl-C1-C2 alkyl,
benzyl,
the phenyl moiety of the benzyl being optionally substituted with one, two, or three C1-C2 alkyl substituents,
the methyl moiety of the benzyl being optionally substituted with C1-C2 alkyl,
benzyl-C3-C4 cycloalkyl,
imidazolyl-C1-C2 alkyl, the imidazolyl-C1-C2 alkyl being optionally substituted with one, two, or three C1-C2 alkyl substituents,
oxazolyl-C1-C2 alkyl, the oxazolyl-C1-C2 alkyl being optionally substituted with one, two, or three C1-C2 alkyl substituents,
pyridinyl-C1-C2 alkyl,
and phenyl, the phenyl being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C2 alkyl, halogen, and C1-C2 alkoxy,
or —N(R5R7) being selected from the group consisting of 5 to 7 membered cyclic amines which contain one or two ring nitrogen atoms, zero or one ring oxygen atom, and zero or one ring sulfur atom, and are attached via a ring nitrogen atom, the 5 to 7 membered cyclic amines being optionally substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkoxy, C1-C2 alkoxy C1-C2 alkyl, oxo, hydroxyl, halogen, and C1-C3 alkyl,
or —N(R5R7) being selected from the group consisting of two annelated, aromatic, partially saturated or saturated rings which are each 5-7 membered and each contain one or two ring nitrogen atoms and are attached via a ring nitrogen atom,
or —N(R5R7) being selected from the group consisting of azaspiro[2.5] oct-5-yl and oxa-azaspiro[3.5] non-1-yl, the azaspiro compounds being optionally substituted with oxo;
or R2 and R3 together form a C5-C6 cycloalkyl ring;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 4 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is selected from the group consisting of hydrogen and C1-C5 alkyl;
R2 is selected from the group consisting of hydrogen, methyl, ethyl, trifluoromethyl, and methylsulfanyl;
R3 is selected from the group consisting of C1-C4 alkylester, the alkylester being optionally substituted with one, two, or three fluorine substituents, C3-C4 cycloalkylester, C3-C4 cycloalkyl,
5 membered heteroaryl,
the 5 membered heteroaryl being optionally substituted with one or two substituents selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C1-C4 haloalkyl, C1-C2 aminoalkyl, C1-C2 alkylester, C1-C2 alkoxy, C1-C2 haloalkoxy, C1-C2 alkoxy-C1-C4 alkyl, cyano, hydroxyl, carboxyl, C1-C2 alkyl-SO2—C1-C2 alkyl, and —CO—NH2,
or the 5 membered heteroaryl being optionally substituted with one C3-C6 cycloalkyl, the C3-C6 cycloalkyl optionally being substituted with one, two, or three chlorine, fluorine, or methyl substituents, or one or two methyl substituents, or with phenyl, the phenyl being optionally substituted with C1-C2 alkoxy, chlorine, or fluorine,
bridged bi- or tricycloalkyl,
C3-C6 cycloalkyl-C1-C2 alkyl,
C3-C6 cycloalkyl-C1-C4 alkenyl,
phenyl, the phenyl optionally being substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, chlorine, fluorine, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, C1-C2-alkylester, nitro, amino, di-C1-C2 alkylamino, and cyano,
phenyl-C1-C2 alkyl,
the phenyl moiety optionally being substituted with one, two, or three substituents selected from the group consisting of fluorine, chlorine, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy, and hydroxyl,
the alkyl moiety optionally being substituted with one or two substituents selected from the group consisting of C1-C2 alkyl and hydroxyl,
5-6 membered heterocycloalkyl, the 5-6 membered heterocycloalkyl being optionally substituted with C3-C5 cycloalkyl or C1-C3 alkyl,
5-6 membered heterocycloalkyl-C1-C2 alkyl,
the 5-6 membered heterocycloalkyl moiety being optionally substituted with C1-C2 alkyl or oxo,
the C1-C2 alkyl moiety being optionally substituted with C1-C2 alkyl,
5-6 membered heteroaryl, the 5-6 membered heteroaryl being optionally substituted with one, two, or three substituents selected from the group consisting of fluorine, chlorine, C1-C3 alkyl, and C1-C2 fluoroalkyl,
and 5-6 membered heteroaryl-C1-C4 alkyl,
the 5-6 membered heteroaryl-moiety being optionally substituted with one or two substituents selected from the group consisting of C1-C2 alkoxy and C1-C2 alkyl,
the C1-C2 alkyl-moiety being optionally substituted with one or two methyl substituents;
or R2 and R3 together form a C5-C6 cycloalkyl ring;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 5 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is selected from the group consisting of 1,2,4 oxadiazol-5-yl of formula
1,3,4 oxadiazol-5-yl of formula
and 1,2,4 oxadiazol-3-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # denotes the optional binding to a further substituent, the oxadiazolyl being substituted with a substituent selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C1-C4 fluoroalkyl, C1-C2 fluoroalkoxy, methoxy-C1-C4 alkyl, tert-butoxy-ethyl, C1-C2 alkylester,
C3-C6 cycloalkyl, the C3-C6 cycloalkyl optionally being substituted with chlorine, fluorine, methyl, or phenyl, the phenyl optionally being substituted with chlorine or methoxy,
oxanyl,
oxopyrrolidinyl-methyl,
piperidinyl, the piperidinyl being substituted with cyclopropyl or iso-propyl,
piperidinyl-methyl, the piperidinylmethyl being optionally substituted with methyl,
morpholinyl-ethyl, the ethyl moiety being optionally substituted with methyl,
tetrahydrofuranyl,
phenyl, the phenyl optionally being substituted with one, two, or three substituents selected from the group consisting of C1-C4 alkyl, fluorine, chlorine, trifluoromethyl, methoxy, trifluoromethoxy, methylester, nitro, amino, di-methylamino, and cyano,
and benzyl,
the phenyl moiety of the benzyl being optionally substituted with one or two fluorine or one methoxy substituent,
or the phenyl moiety of the benzyl being optionally substituted with one or two substituents selected from the group consisting of fluorine, chlorine, methoxy, and hydroxyl,
or the phenyl moiety being optionally substituted with one substituent selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, methoxy, isopropyloxy, trifluoromethoxy, and difluoromethoxy,
the methyl moiety of the benzyl being optionally substituted with hydroxyl, ethyl, or one or two methyl substituents,
1,2 oxazolyl, the 1,2 oxazolyl being substituted with phenyl,
thiophen-yl, the thiophen-yl being optionally substituted with a substituent selected from the group consisting of methyl and cyano,
1,3 thiazolyl,
the 1,3 thiazolyl being optionally substituted with one substituent selected from the group consisting of C1-C5 alkyl, C1-C4 haloalkyl, cyclopropyl, and phenyl, the phenyl being optionally substituted with one or two substituents selected from the group consisting of fluorine, chlorine, methyl, and trifluoromethyl,
or the 1,3 thiazolyl being optionally substituted with two substituents selected from the group consisting of methyl, ethyl, and iso-propyl substituents, or the thiazolyl being optionally substituted with phenyl and methyl,
and pyridinyl, the pyridinyl being optionally substituted with one or two substituents selected from the group consisting of fluorine, chlorine, methyl, and trifluoromethyl;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 6 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is selected from the group consisting of 1,2,4 oxadiazol-5-yl of formula
1,3,4 oxadiazol-5-yl of formula
and 1,2,4 oxadiazol-3-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # denotes the optional binding to a further substituent, the oxadiazolyl being optionally substituted with one substituent selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, hexyl, trifluoromethyl, trifluoroethyl, trifluorobutyl, methoxymethyl, methoxypropyl, methoxyisobutyl, ethylester, C3-C6 cycloalkyl,
benzyl, the phenyl moiety of the benzyl being optionally substituted with one or two substituents selected from the group consisting of methyl, methoxy, isopropyloxy, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, and difluoromethoxy,
and pyridinyl, the pyridinyl being optionally substituted with chlorine, fluorine, methyl, or trifluoromethyl;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 7 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4-oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # denotes the optional binding to a further substituent, the oxadiazolyl being substituted with tert-butyl;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 8 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is methyl;
R3 is selected from the group consisting of 1,2,4 oxadiazol-5-yl of formula
1,3,4 oxadiazol-5-yl of formula
and 1,2,4 oxadiazol-3-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # denotes the optional binding to a further substituent, the oxadiazolyl being optionally substituted with one substituent selected from the group consisting of methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxyethyl, tert-butoxyethyl,
C3-C6 cycloalkyl, the C3-C6 cycloalkyl being optionally substituted with one or two methyl substituents,
cyclobutyl,
benzyl, the phenyl moiety of the benzyl being optionally substituted with a substituent selected from the group consisting of fluorine, chlorine, and hydroxyl,
and phenyl, the phenyl being optionally substituted with a substituent selected from the group consisting of methyl, fluorine, chlorine, methoxy, trifluoromethyl, and trifluoromethoxy;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 9 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is selected from the group consisting of methylester, ethylester, propylester, isopropylester, the ethylester and the propylester being optionally substituted with one, two, or three fluorine substituents, and cyclobutylester;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 10 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is methyl;
R3 is selected from the group consisting of ethylester, propylester, isopropylester, tert-butylester, the ethylester and the propylester being optionally substituted with one, two, or three fluorine substituents, and cyclobutylester;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 11 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is methyl;
R3 is ethylester;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 12 (depends on 1, 2)

Compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is selected from the group consisting of trifluoromethyl, ethyl, and methylsulfanyl;
R3 is selected from the group consisting of C1-C4 alkylester, the C4 alkylester being optionally substituted with one, two, or three fluorine substituents, and C3-C4 cycloalkylester;
or a salt of the compound, or a solvate of the compound, or a solvate of the salt thereof.

### Claim 13 (depends on 2)

Compound of formula (I-B) as defined in claim 2 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4 oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # indicates the position of binding to a phenyl substituent, the phenyl being optionally substituted with a substituent selected from the group consisting of methyl, trifluoromethyl, chloro, and fluoro;
wherein the acid is hydrochloric acid.

### Claim 14 (depends on 13)

Compound of formula (I-B) as defined in claim 13 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4 oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # indicates the position of binding to a phenyl substituent;
wherein the acid is hydrochloric acid.

### Claim 15 (depends on 13)

Compound of formula (I-B) as defined in claim 13 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4 oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # indicates the position of binding to a phenyl substituent, the phenyl being substituted by methyl in para position;
wherein the acid is hydrochloric acid.

### Claim 16 (depends on 13)

Compound of formula (I-B) as defined in claim 13 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4 oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # indicates the position of binding to a phenyl substituent, the phenyl being substituted by trifluoromethyl in para position;
wherein the acid is hydrochloric acid.

### Claim 17 (depends on 13)

Compound of formula (I-B) as defined in claim 13 in which
R1 is hydrogen;
R2 is hydrogen;
R3 is 1,2,4 oxadiazol-5-yl of formula
wherein * indicates the position of binding to the pyrazolopyrimidone and # indicates the position of binding to a phenyl substituent, the phenyl being substituted by chloro in meta position;
wherein the acid is hydrochloric acid.

### Claim 18 (depends on 1, 2)

Medicament, comprising a compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2; in combination with an inert, non-toxic, pharmaceutically suitable auxiliary.

### Claim 19 (depends on 1, 2)

Medicament, comprising a compound of formula (I-A) as defined in claim 1 or formula (I-B) as defined in claim 2; in combination with a further active compound selected from the group consisting of Factor VIII, Factor IX, Factor VIIa, activated prothrombin complex concentrates (aPCC) or prothrombin complex concentrates (PCCs), ε-aminocaproic acid, ethamsylate, paraaminobutyl benzoic acid, tranexamic acid, desmopressin, danazol, combined oral contraceptive pills (COCPs), progestin intrauterine system, glucocorticoid receptor agonists, analgesics, and nonsteroidal anti-inflammatory drugs (NSAIDs).