SK372001A3 - Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain - Google Patents

Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain Download PDF

Info

Publication number: SK372001A3
Authority: SK; Slovakia
Prior art keywords: butyl; tetrahydropyridyl; phenyl; hydroxy; piperidyl
Prior art date: 1998-07-10

Application number

SK37-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Ramon Merce-Vidal

Jordi Frigola-Constansa

Original Assignee

Esteve Labor Dr

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-07-10

Filing date

1999-07-09

Publication date

2001-10-08

1999-07-09 Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr

2001-10-08 Publication of SK372001A3 publication Critical patent/SK372001A3/sk

Links

125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 36
208000002193 Pain Diseases 0.000 claims description 19
230000000202 analgesic effect Effects 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 13
208000004296 neuralgia Diseases 0.000 claims description 12
208000021722 neuropathic pain Diseases 0.000 claims description 12
208000001294 Nociceptive Pain Diseases 0.000 claims description 11
208000005298 acute pain Diseases 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
241000282412 Homo Species 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
-1 alkoxy radical Chemical class 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
230000036407 pain Effects 0.000 claims description 8
150000003254 radicals Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
OTZWITHPRWRMMX-UHFFFAOYSA-N 2-butyl-1h-pyrrole Chemical class CCCCC1=CC=CN1 OTZWITHPRWRMMX-UHFFFAOYSA-N 0.000 claims description 3
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 2
125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims 67
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 18
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 14
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
IQEFJLZCCQULED-UHFFFAOYSA-N 1-[4-(4,5-diphenylimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IQEFJLZCCQULED-UHFFFAOYSA-N 0.000 claims 2
RRLIHVYOHXQZNB-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCCN1C=C(Cl)C=N1 RRLIHVYOHXQZNB-UHFFFAOYSA-N 0.000 claims 2
ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 claims 2
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
LBCUSCPNGDWLSX-UHFFFAOYSA-N 1-(4-indazol-2-ylbutyl)-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2N=C3C=CC=CC3=C2)CCC1(O)C1=CC=CC=C1 LBCUSCPNGDWLSX-UHFFFAOYSA-N 0.000 claims 1
TZTYVWIHVWABMX-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(F)=CC=2)CC1 TZTYVWIHVWABMX-UHFFFAOYSA-N 0.000 claims 1
DWLLHISUEJCRET-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(C)=CC=2)CC1 DWLLHISUEJCRET-UHFFFAOYSA-N 0.000 claims 1
BPRIVJYXNGZFOZ-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=C(C=CC=2)C(F)(F)F)CC1 BPRIVJYXNGZFOZ-UHFFFAOYSA-N 0.000 claims 1
BKPCCBJZYMDFDI-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC=CC=2)CC1 BKPCCBJZYMDFDI-UHFFFAOYSA-N 0.000 claims 1
ZJDHFMQZTGLTLM-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CCCCN2N=CC(Cl)=C2)CC1 ZJDHFMQZTGLTLM-UHFFFAOYSA-N 0.000 claims 1
WHDQDXIMDQOROY-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-naphthalen-1-ylpiperidin-4-ol Chemical compound C1CC(O)(C=2C3=CC=CC=C3C=CC=2)CCN1CCCCN1C=C(Cl)C=N1 WHDQDXIMDQOROY-UHFFFAOYSA-N 0.000 claims 1
YXFWAEHLJYPYHN-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-naphthalen-2-ylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=C3C=CC=CC3=CC=2)CCN1CCCCN1C=C(Cl)C=N1 YXFWAEHLJYPYHN-UHFFFAOYSA-N 0.000 claims 1
RGRYAKLFIRPFCR-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=C(Cl)C=N1 RGRYAKLFIRPFCR-UHFFFAOYSA-N 0.000 claims 1
YNPOBHOYLBLMMF-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=C2)CCC1(O)C1=CC=C(F)C=C1 YNPOBHOYLBLMMF-UHFFFAOYSA-N 0.000 claims 1
PUJHXTDMPCWZES-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CCCCN2C3=CC=CC=C3N=C2)CC1 PUJHXTDMPCWZES-UHFFFAOYSA-N 0.000 claims 1
CQPOTRWYHMDELP-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=C2)CCC1(O)C1=CC=CC=C1 CQPOTRWYHMDELP-UHFFFAOYSA-N 0.000 claims 1
JURXEPPWCAMPQT-UHFFFAOYSA-N 1-[4-(benzotriazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=N2)CCC1(O)C1=CC=C(F)C=C1 JURXEPPWCAMPQT-UHFFFAOYSA-N 0.000 claims 1
ZOLFUYXXKMOHMI-UHFFFAOYSA-N 1-[4-(benzotriazol-2-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2N=C3C=CC=CC3=N2)CCC1(O)C1=CC=C(F)C=C1 ZOLFUYXXKMOHMI-UHFFFAOYSA-N 0.000 claims 1
GBOMGWIDQVYPSD-UHFFFAOYSA-N 1-[4-[4-(4-chlorophenyl)pyrazol-1-yl]butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN(N=C1)C=C1C1=CC=C(Cl)C=C1 GBOMGWIDQVYPSD-UHFFFAOYSA-N 0.000 claims 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
BDMFEFZOOOYCKN-UHFFFAOYSA-N 1-propylpyrazole Chemical compound CCCN1C=CC=N1 BDMFEFZOOOYCKN-UHFFFAOYSA-N 0.000 claims 1
SIQHSJOKAUDDLN-UHFFFAOYSA-N 2-methyl-1-propylimidazole Chemical compound CCCN1C=CN=C1C SIQHSJOKAUDDLN-UHFFFAOYSA-N 0.000 claims 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
HSFXDMSGPROVRE-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(Cl)=CC=2)CC1 HSFXDMSGPROVRE-UHFFFAOYSA-N 0.000 claims 1
LDDHWPCVVUARIS-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4-chloropyrazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCCN1C=C(Cl)C=N1 LDDHWPCVVUARIS-UHFFFAOYSA-N 0.000 claims 1
NCSUPLXPBOEGCC-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(triazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCCN1C=CN=N1 NCSUPLXPBOEGCC-UHFFFAOYSA-N 0.000 claims 1
ABKAYOFKLFOUTI-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-(4-indazol-1-ylbutyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3C=N2)CCC1(O)C1=CC=C(F)C=C1 ABKAYOFKLFOUTI-UHFFFAOYSA-N 0.000 claims 1
GJMZEQAGUIAFDM-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-(4-indazol-2-ylbutyl)piperidin-4-ol Chemical compound C1CN(CCCCN2N=C3C=CC=CC3=C2)CCC1(O)C1=CC=C(F)C=C1 GJMZEQAGUIAFDM-UHFFFAOYSA-N 0.000 claims 1
PRVLZGBHJIWNAK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-[4-(triazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(F)=CC=2)CCN1CCCCN1C=CN=N1 PRVLZGBHJIWNAK-UHFFFAOYSA-N 0.000 claims 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
QPDUNGVMKHTKOD-UHFFFAOYSA-N 4-phenyl-1-(4-pyrazol-1-ylbutyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=CC=N1 QPDUNGVMKHTKOD-UHFFFAOYSA-N 0.000 claims 1
JFHHUMHVYLZACW-UHFFFAOYSA-N 4-phenyl-1-[4-(1,2,4-triazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=NC=N1 JFHHUMHVYLZACW-UHFFFAOYSA-N 0.000 claims 1
CDQRJAXVBKJQLT-UHFFFAOYSA-N 4-phenyl-1-[4-(2-phenylimidazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=CN=C1C1=CC=CC=C1 CDQRJAXVBKJQLT-UHFFFAOYSA-N 0.000 claims 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
229940035676 analgesics Drugs 0.000 description 9
239000000730 antalgic agent Substances 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
238000003556 assay Methods 0.000 description 8
238000007920 subcutaneous administration Methods 0.000 description 7
229960005181 morphine Drugs 0.000 description 6
150000001721 carbon Chemical group 0.000 description 5
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 5
229960005301 pentazocine Drugs 0.000 description 5
239000002904 solvent Substances 0.000 description 5
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229960001138 acetylsalicylic acid Drugs 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 3
208000004550 Postoperative Pain Diseases 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
102000035038 5-HT1 receptors Human genes 0.000 description 1
108091005478 5-HT1 receptors Proteins 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
206010049589 Afterbirth pain Diseases 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
208000008035 Back Pain Diseases 0.000 description 1
206010058019 Cancer Pain Diseases 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000723347 Cinnamomum Species 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
208000007914 Labor Pain Diseases 0.000 description 1
208000035945 Labour pain Diseases 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
206010049816 Muscle tightness Diseases 0.000 description 1
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
101000941356 Nostoc ellipsosporum Cyanovirin-N Proteins 0.000 description 1
241001494479 Pecora Species 0.000 description 1
208000004983 Phantom Limb Diseases 0.000 description 1
206010056238 Phantom pain Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
206010039966 Senile dementia Diseases 0.000 description 1
102100028656 Sigma non-opioid intracellular receptor 1 Human genes 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000006986 amnesia Effects 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
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239000004927 clay Substances 0.000 description 1
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231100000869 headache Toxicity 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
108010080097 sigma-1 receptor Proteins 0.000 description 1
239000000243 solution Substances 0.000 description 1
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229910052717 sulfur Inorganic materials 0.000 description 1
239000011885 synergistic combination Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect

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Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)

SK37-2001A 1998-07-10 1999-07-09 Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain SK372001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES009801467A ES2151828B1 (es)	1998-07-10	1998-07-10	Empleo de derivados de tetrahidropiridinas (ohidroxi-piperidinas)-b utilazoles en la elaboracion de un medicamento para el tratamiento del dolor.
PCT/ES1999/000222 WO2000002519A2 (es)	1998-07-10	1999-07-09	Empleo de derivados de tetrahidropiridinas (o 4-hidroxipiperidinas)-butilazoles en la elaboracion de un medicamento para el tratamiento del dolor

Publications (1)

Publication Number	Publication Date
SK372001A3 true SK372001A3 (en)	2001-10-08

Family

ID=8304473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK37-2001A SK372001A3 (en)	1998-07-10	1999-07-09	Utilization of derivatives of tetrahydropyridines (or 4-hydroxypiperidines)-butylazols in the preparation of a medicament for the treatment of pain

Country Status (31)

Country	Link
US (2)	USRE39113E1 (uk)
EP (1)	EP1097698B1 (uk)
JP (1)	JP2002520261A (uk)
KR (1)	KR100758740B1 (uk)
CN (1)	CN1134259C (uk)
AR (1)	AR019894A1 (uk)
AT (1)	ATE239476T1 (uk)
AU (1)	AU747073C (uk)
BG (1)	BG64725B1 (uk)
BR (1)	BR9912000A (uk)
CA (1)	CA2336784A1 (uk)
CO (1)	CO5060468A1 (uk)
CZ (1)	CZ292015B6 (uk)
DE (1)	DE69907685T2 (uk)
DK (1)	DK1097698T3 (uk)
ES (2)	ES2151828B1 (uk)
HU (1)	HUP0102868A3 (uk)
ID (1)	ID28817A (uk)
IL (1)	IL140854A (uk)
MX (1)	MXPA01000369A (uk)
NO (1)	NO20010147L (uk)
NZ (1)	NZ509556A (uk)
PL (1)	PL194721B1 (uk)
PT (1)	PT1097698E (uk)
RU (1)	RU2202347C2 (uk)
SK (1)	SK372001A3 (uk)
TR (1)	TR200100043T2 (uk)
TW (1)	TW589317B (uk)
UA (1)	UA57149C2 (uk)
WO (1)	WO2000002519A2 (uk)
ZA (1)	ZA200100240B (uk)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6995144B2 (en) *	2002-03-14	2006-02-07	Eisai Co., Ltd.	Nitrogen containing heterocyclic compounds and medicines containing the same
EP1481680A1 (en) *	2003-05-30	2004-12-01	Aventis Pharma Deutschland GmbH	Use of S1P
DE602004017316D1 (de)	2003-07-24	2008-12-04	Euro Celtique Sa	Heteroaryl-tetrahydropyridylverbindungen, die sich für die behandlung bzw. die prävention von schmerzen eignen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1833618A3 (ru) *	1991-01-28	1995-07-09	Институт химических наук АН Республики Казахстан	1-(3-бутоксипропил)-4-оксопиперидин в качестве промежуточного соединения в синтезе гидрохлорида 1-(3-бутоксипропил)-4-фенил-4-пропионилоксипиперидина, обладающего анальгетической активностью
JPH084287A (ja) *	1994-06-16	1996-01-09	Tateyama Alum Ind Co Ltd	柱体のコンクリート床面立設方法及びこれに用いる治具
FR2723091B1 (fr) *	1994-07-29	1996-11-08	Esteve Labor Dr	Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles
EP0906104A4 (en) *	1996-03-25	2003-12-10	Lilly Co Eli	PAIN TREATMENT PROCESS

1998
- 1998-07-10 ES ES009801467A patent/ES2151828B1/es not_active Expired - Fee Related
1999
- 1999-07-01 CO CO99041288A patent/CO5060468A1/es unknown
- 1999-07-07 AR ARP990103289A patent/AR019894A1/es unknown
- 1999-07-09 WO PCT/ES1999/000222 patent/WO2000002519A2/es not_active Ceased
- 1999-07-09 MX MXPA01000369A patent/MXPA01000369A/es active IP Right Grant
- 1999-07-09 CA CA002336784A patent/CA2336784A1/en not_active Abandoned
- 1999-07-09 BR BR9912000-3A patent/BR9912000A/pt not_active Application Discontinuation
- 1999-07-09 JP JP2000558783A patent/JP2002520261A/ja not_active Ceased
- 1999-07-09 PT PT99929333T patent/PT1097698E/pt unknown
- 1999-07-09 US US10/355,216 patent/USRE39113E1/en not_active Expired - Fee Related
- 1999-07-09 KR KR1020017000391A patent/KR100758740B1/ko not_active Expired - Fee Related
- 1999-07-09 HU HU0102868A patent/HUP0102868A3/hu unknown
- 1999-07-09 CN CNB998102083A patent/CN1134259C/zh not_active Expired - Fee Related
- 1999-07-09 TR TR2001/00043T patent/TR200100043T2/xx unknown
- 1999-07-09 EP EP99929333A patent/EP1097698B1/en not_active Expired - Lifetime
- 1999-07-09 AT AT99929333T patent/ATE239476T1/de not_active IP Right Cessation
- 1999-07-09 DE DE69907685T patent/DE69907685T2/de not_active Expired - Lifetime
- 1999-07-09 US US09/743,085 patent/US6384055B1/en not_active Ceased
- 1999-07-09 DK DK99929333T patent/DK1097698T3/da active
- 1999-07-09 IL IL140854A patent/IL140854A/en not_active IP Right Cessation
- 1999-07-09 ES ES99929333T patent/ES2198136T3/es not_active Expired - Lifetime
- 1999-07-09 AU AU46171/99A patent/AU747073C/en not_active Ceased
- 1999-07-09 NZ NZ509556A patent/NZ509556A/xx unknown
- 1999-07-09 PL PL99345781A patent/PL194721B1/pl not_active IP Right Cessation
- 1999-07-09 SK SK37-2001A patent/SK372001A3/sk unknown
- 1999-07-09 ID IDW20010066A patent/ID28817A/id unknown
- 1999-07-09 CZ CZ200175A patent/CZ292015B6/cs not_active IP Right Cessation
- 1999-07-09 RU RU2001103738/14A patent/RU2202347C2/ru not_active IP Right Cessation
- 1999-08-10 TW TW088112508A patent/TW589317B/zh not_active IP Right Cessation
- 1999-09-07 UA UA2001010210A patent/UA57149C2/uk unknown
2001
- 2001-01-09 ZA ZA200100240A patent/ZA200100240B/en unknown
- 2001-01-09 NO NO20010147A patent/NO20010147L/no not_active Application Discontinuation
- 2001-01-10 BG BG105141A patent/BG64725B1/bg unknown

Also Published As

Publication number	Publication date
BG105141A (en)	2001-10-31
DK1097698T3 (da)	2003-09-01
PL345781A1 (en)	2002-01-02
US6384055B1 (en)	2002-05-07
AR019894A1 (es)	2002-03-20
PT1097698E (pt)	2003-09-30
PL194721B1 (pl)	2007-06-29
NZ509556A (en)	2002-08-28
JP2002520261A (ja)	2002-07-09
USRE39113E1 (en)	2006-05-30
UA57149C2 (uk)	2003-06-16
AU747073C (en)	2003-06-19
CN1314814A (zh)	2001-09-26
ES2198136T3 (es)	2004-01-16
WO2000002519A3 (es)	2000-04-20
ATE239476T1 (de)	2003-05-15
ES2151828A1 (es)	2001-01-01
RU2202347C2 (ru)	2003-04-20
NO20010147D0 (no)	2001-01-09
EP1097698A2 (en)	2001-05-09
AU747073B2 (en)	2002-05-09
DE69907685T2 (de)	2004-03-11
CO5060468A1 (es)	2001-07-30
DE69907685D1 (de)	2003-06-12
WO2000002519A2 (es)	2000-01-20
BG64725B1 (bg)	2006-01-31
TW589317B (en)	2004-06-01
IL140854A (en)	2006-12-31
ZA200100240B (en)	2001-09-03
ID28817A (id)	2001-07-05
CZ292015B6 (cs)	2003-07-16
ES2151828B1 (es)	2001-08-16
CZ200175A3 (cs)	2001-07-11
CN1134259C (zh)	2004-01-14
HUP0102868A2 (hu)	2001-12-28
MXPA01000369A (es)	2003-06-19
TR200100043T2 (tr)	2001-09-21
EP1097698B1 (en)	2003-05-07
HUP0102868A3 (en)	2003-01-28
KR100758740B1 (ko)	2007-09-14
IL140854A0 (en)	2003-09-17
BR9912000A (pt)	2001-05-29
AU4617199A (en)	2000-02-01
KR20010071824A (ko)	2001-07-31
CA2336784A1 (en)	2000-01-20
NO20010147L (no)	2001-01-09

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