CS256366B2 - Method of new 3-(1-piperidinylalkyl)-4h-pyridol(1,2-pyrimidine-4-on derivatives production - Google Patents

Method of new 3-(1-piperidinylalkyl)-4h-pyridol(1,2-pyrimidine-4-on derivatives production Download PDF

Info

Publication number: CS256366B2
Authority: CS; Czechoslovakia
Prior art keywords: parts; piperidinyl; methyl; pyrido; pyrimidin
Prior art date: 1980-03-28

Application number

CS812134A

Other languages

Czech (cs)

English (en)

Inventor

Ludo E J Kennis

Josephus C Mertens

Original Assignee

Janssen Pharmaceutica Nv

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.)

1980-03-28

Filing date

1981-03-24

Publication date

1988-04-15

1981-03-24 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1988-04-15 Publication of CS256366B2 publication Critical patent/CS256366B2/cs

Links

238000000034 method Methods 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 36
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
-1 C 1 -C 4 alkyl Chemical group 0.000 claims description 48
239000011541 reaction mixture Substances 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 1
229940082988 antihypertensives serotonin antagonists Drugs 0.000 abstract description 3
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230000003389 potentiating effect Effects 0.000 abstract 1
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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239000002585 base Substances 0.000 description 22
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239000000047 product Substances 0.000 description 16
239000004480 active ingredient Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 9
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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150000001298 alcohols Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 3
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
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QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 3
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BHWNQRHBJTYLBS-UHFFFAOYSA-N (3-methylphenyl)-(1-methylpiperidin-4-yl)methanone Chemical compound C1CN(C)CCC1C(=O)C1=CC=CC(C)=C1 BHWNQRHBJTYLBS-UHFFFAOYSA-N 0.000 description 2
AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 2
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125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
229960004650 metergoline Drugs 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
229960003955 mianserin Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
WHLAAOUBNDBWLA-UHFFFAOYSA-N phenyl(piperidin-4-yl)methanone;hydrobromide Chemical compound Br.C=1C=CC=CC=1C(=O)C1CCNCC1 WHLAAOUBNDBWLA-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
JUOYGTQAFOURCO-UHFFFAOYSA-N piperidin-4-yl(thiophen-2-yl)methanone;hydrobromide Chemical compound Br.C=1C=CSC=1C(=O)C1CCNCC1 JUOYGTQAFOURCO-UHFFFAOYSA-N 0.000 description 1
FIADGNVRKBPQEU-UHFFFAOYSA-N pizotifen Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCC2=C1C=CS2 FIADGNVRKBPQEU-UHFFFAOYSA-N 0.000 description 1
229960004572 pizotifen Drugs 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
CSIGAEASXSGNKS-UHFFFAOYSA-N propane-1,1,3-triol Chemical compound OCCC(O)O CSIGAEASXSGNKS-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000028327 secretion Effects 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
208000027185 varicose disease Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

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

CS812134A 1980-03-28 1981-03-24 Method of new 3-(1-piperidinylalkyl)-4h-pyridol(1,2-pyrimidine-4-on derivatives production CS256366B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13484580A	1980-03-28	1980-03-28
US06/191,632 US4342870A (en)	1980-03-28	1980-09-29	Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives

Publications (1)

Publication Number	Publication Date
CS256366B2 true CS256366B2 (en)	1988-04-15

Family

ID=26832744

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS812134A CS256366B2 (en)	1980-03-28	1981-03-24	Method of new 3-(1-piperidinylalkyl)-4h-pyridol(1,2-pyrimidine-4-on derivatives production

Country Status (22)

Country	Link
US (1)	US4342870A (fr)
EP (1)	EP0037265B1 (fr)
AU (1)	AU537700B2 (fr)
BG (1)	BG36199A3 (fr)
CA (1)	CA1163994A (fr)
CS (1)	CS256366B2 (fr)
DE (1)	DE3168433D1 (fr)
DK (1)	DK159390C (fr)
ES (1)	ES500814A0 (fr)
FI (1)	FI71737C (fr)
GR (1)	GR72488B (fr)
HU (1)	HU187329B (fr)
IE (1)	IE51319B1 (fr)
IL (1)	IL62494A (fr)
MA (1)	MA19107A1 (fr)
NO (1)	NO156752C (fr)
NZ (1)	NZ196522A (fr)
PH (1)	PH16530A (fr)
PT (1)	PT72740B (fr)
RO (1)	RO82508A (fr)
SU (1)	SU1068037A3 (fr)
YU (1)	YU43010B (fr)

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US4443451A (en) *	1981-07-15	1984-04-17	Janssen Pharmaceutica N.V.	Bicyclic pyrimidin-5-one derivatives
US4548938A (en) *	1981-07-15	1985-10-22	Janssen Pharmaceutica N.V.	5-H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one compounds
US4355037A (en) *	1981-11-12	1982-10-19	Hoechst-Roussel Pharmaceuticals	3-(4-Piperidyl)-1,2-benzisoxales
US4485107A (en) *	1982-11-01	1984-11-27	Janssen Pharmaceutica N.V.	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones
US4581171A (en) *	1983-07-27	1986-04-08	Janssen Pharmaceutica, N.V.	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders
US4695569A (en) *	1983-11-30	1987-09-22	Janssen Pharmaceutica N.V.	Bicyclic heterocyclyl containing N-(bicyclic heterocyclyl)-4-piperidinamines
US4888426A (en) *	1983-11-30	1989-12-19	Janssen Pharmaceutica N.V.	1-(5-methyl-furan-2-ylmethyl)-N-(4-piperidinyl)imidazo [4,5-6]pyridine-2-amine
PH23995A (en) *	1984-01-09	1990-02-09	Janssen Pharmaceutica Nv	4((bicycle heterocyclyl)-methyl and hetero)piperidines
US4548939A (en) *	1984-10-01	1985-10-22	Janssen Pharmaceutica N. V.	1H-Indol-3-yl containing 1,3-dimethyl-1H-purine-2,6-diones
US4804663A (en) *	1985-03-27	1989-02-14	Janssen Pharmaceutica N.V.	3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles
SG47757A1 (en) *	1986-09-22	1998-04-17	Janssen Pharmaceutica Nv	Serotonin antagonists for treating wounds
IL90879A0 (en) *	1988-09-02	1990-02-09	Janssen Pharmaceutica Nv	3-piperidinyl-indazole derivatives,their preparation and antihypertensive compositions containing them
CA2000786C (fr) *	1988-11-07	1999-01-26	Cornelus G. M. Janssen	3-piperidinyl-1,2-benzisoxazoles
US5153206A (en) *	1988-12-02	1992-10-06	Pfizer Inc.	Arylpiperidine derivatives
EP0460118A1 (fr) *	1989-03-23	1991-12-11	Mallinckrodt International Corporation	Compose de piperidine marque a l'iode ou au brome radioactif, son procede de preparation et composition comprenant ledit compose
DE4138756A1 (de) *	1991-11-26	1993-05-27	Troponwerke Gmbh & Co Kg	Kombination mit neuroprotektiver wirkung
US5266571A (en) *	1992-01-09	1993-11-30	Amer Moh Samir	Treatment of hemorrhoids with 5-HT2 antagonists
EP0626968B1 (fr) *	1992-02-13	2001-09-26	Merrell Pharmaceuticals Inc.	Derives piperidinyles thiacycliques
JPH07508741A (ja)	1992-07-13	1995-09-28	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	新規４−（３−ベンゾフラニル）ピペリジニル及び４−（３−ベンゾチエニル）ピペリジニル誘導体，ならびにそれらを含む製薬学的組成物
RU2178695C2 (ru) *	1993-11-19	2002-01-27	Жансен Фармасетика Н.В.	Микрокапсулы, содержащие рисперидон, фармацевтическая композиция и способы их получения
ES2085234B1 (es) *	1994-02-24	1997-01-16	Vita Invest Sa	Agente activo sobre el sistema nervioso central, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen.
TW421649B (en) *	1995-01-31	2001-02-11	Janssen Pharmaceutica Nv	4-(1H-indol-1yl)-1-piperidinyl derivatives
US5753664A (en) *	1995-03-16	1998-05-19	Takeda Chemical Industries, Ltd.	Heterocyclic compounds, their production and use
WO2004043923A1 (fr) *	2002-11-13	2004-05-27	Synthon B.V.	Procede de fabrication de la risperidone et des intermediaires associes
WO2004094414A1 (fr) *	2003-04-22	2004-11-04	Synthon B.V.	Sels hydrosolubles de risperidone
CN101970427A (zh) *	2008-02-29	2011-02-09	Vm生物医药公司	治疗疼痛症状及其它失调的方法
EP2812004B1 (fr) *	2012-02-10	2018-06-27	PTC Therapeutics, Inc.	Composés destinés au traitement de l'amyotrophie spinale
EA029155B1 (ru)	2012-03-01	2018-02-28	ПиТиСи ТЕРАПЬЮТИКС, ИНК.	Соединения для лечения спинальной мышечной атрофии
MX358514B (es)	2012-03-23	2018-08-24	Ptc Therapeutics Inc	Compuestos para tratar la atrofia muscular espinal.
WO2014143915A1 (fr) *	2013-03-15	2014-09-18	Vm Therapeutics Llc	Nouvelles formes cristallines
WO2015105657A1 (fr)	2013-12-19	2015-07-16	Ptc Therapeutics, Inc.	Procédés pour moduler la quantité de transcrits d'arn
EP4249472A3 (fr)	2015-05-30	2023-12-13	PTC Therapeutics, Inc.	Procédés de modulation de l'épissage de l'arn
ES2879995T3 (es)	2015-12-10	2021-11-23	Ptc Therapeutics Inc	Métodos para el tratamiento de la enfermedad de Huntington
EA201991309A1 (ru)	2016-11-28	2019-11-29		Способы модуляции сплайсинга рнк
EP4151627A1 (fr)	2017-06-05	2023-03-22	PTC Therapeutics, Inc.	Composés permettant de traiter la maladie de huntington
AU2018284853A1 (en)	2017-06-14	2019-12-19	Ptc Therapeutics, Inc.	Methods for modifying RNA splicing
CN111163838B (zh)	2017-06-28	2023-03-28	Ptc医疗公司	用于治疗亨廷顿氏病的方法
MX2019015578A (es)	2017-06-28	2020-07-28	Ptc Therapeutics Inc	Metodos para tratar la enfermedad de huntington.
MX2020009957A (es)	2018-03-27	2021-01-15	Ptc Therapeutics Inc	Compuestos para el tratamiento de enfermedad de hungtinton.
SG11202012674PA (en)	2018-06-27	2021-01-28	Ptc Therapeutics Inc	Heterocyclic and heteroaryl compounds for treating huntington's disease
WO2020005882A1 (fr)	2018-06-27	2020-01-02	Ptc Therapeutics, Inc.	Composés hétéroaryles pour le traitement de la maladie de huntington
EA202092899A1 (ru)	2018-06-27	2021-05-14	ПиТиСи ТЕРАПЬЮТИКС, ИНК.	Гетероарильные соединения для лечения болезни гентингтона

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US3412094A (en) *	1967-06-21	1968-11-19	Searle & Co	5-alkyl-2-amino-4-azido-6-phenylpyrimidines and congeners
US3960863A (en) *	1974-06-25	1976-06-01	Sankyo Company Limited	Pyrido[1,2-a]pyrimidinone derivatives
JPS5146497A (en) *	1974-10-19	1976-04-20	Masato Aiura	Hobuban
JPS525795A (en) *	1975-06-28	1977-01-17	Sankyo Co Ltd	Preparation of tetrahydro pyridopyrimidinone derivatives
HU173438B (hu) *	1975-11-27	1979-05-28	Chinoin Gyogyszer Es Vegyeszet	Sposob poluchenija novykh proizvodnykh 4-okso-1,6,7,8-/tetragidro-4h-pirido/1,2/pirimidina s zaderzhivajuhhejj vozgoranie aktivnot'ju i protivosvertivajuhhem effektom

1980
- 1980-09-29 US US06/191,632 patent/US4342870A/en not_active Expired - Lifetime
1981
- 1981-03-03 GR GR64291A patent/GR72488B/el unknown
- 1981-03-04 CA CA000372258A patent/CA1163994A/fr not_active Expired
- 1981-03-17 AU AU68429/81A patent/AU537700B2/en not_active Ceased
- 1981-03-17 NZ NZ196522A patent/NZ196522A/en unknown
- 1981-03-21 MA MA19313A patent/MA19107A1/fr unknown
- 1981-03-24 SU SU813261927A patent/SU1068037A3/ru active
- 1981-03-24 CS CS812134A patent/CS256366B2/cs unknown
- 1981-03-26 PT PT72740A patent/PT72740B/pt not_active IP Right Cessation
- 1981-03-26 DK DK138281A patent/DK159390C/da not_active IP Right Cessation
- 1981-03-26 IL IL62494A patent/IL62494A/xx unknown
- 1981-03-26 PH PH25429A patent/PH16530A/en unknown
- 1981-03-27 ES ES500814A patent/ES500814A0/es active Granted
- 1981-03-27 FI FI810956A patent/FI71737C/fi not_active IP Right Cessation
- 1981-03-27 IE IE706/81A patent/IE51319B1/en not_active IP Right Cessation
- 1981-03-27 BG BG051433A patent/BG36199A3/xx unknown
- 1981-03-27 HU HU81783A patent/HU187329B/hu not_active IP Right Cessation
- 1981-03-27 DE DE8181301335T patent/DE3168433D1/de not_active Expired
- 1981-03-27 YU YU810/81A patent/YU43010B/xx unknown
- 1981-03-27 EP EP81301335A patent/EP0037265B1/fr not_active Expired
- 1981-03-27 NO NO811058A patent/NO156752C/no unknown
- 1981-03-28 RO RO81103848A patent/RO82508A/fr unknown

Also Published As

Publication number	Publication date
AU6842981A (en)	1981-10-01
GR72488B (fr)	1983-11-14
PT72740A (en)	1981-04-01
FI810956L (fi)	1981-09-29
NO156752C (no)	1987-11-18
YU43010B (en)	1989-02-28
PT72740B (en)	1982-11-16
RO82508B (ro)	1983-08-30
US4342870A (en)	1982-08-03
HU187329B (en)	1985-12-28
IL62494A0 (en)	1981-05-20
YU81081A (en)	1983-12-31
IE810706L (en)	1981-09-28
IL62494A (en)	1984-08-31
AU537700B2 (en)	1984-07-05
RO82508A (fr)	1983-09-26
ES8300763A1 (es)	1982-11-01
EP0037265B1 (fr)	1985-01-23
DE3168433D1 (de)	1985-03-07
CA1163994A (fr)	1984-03-20
DK159390B (da)	1990-10-08
MA19107A1 (fr)	1981-10-01
PH16530A (en)	1983-11-10
FI71737B (fi)	1986-10-31
DK138281A (da)	1981-09-29
DK159390C (da)	1991-03-04
ES500814A0 (es)	1982-11-01
BG36199A3 (en)	1984-09-14
NO811058L (no)	1981-09-29
EP0037265A1 (fr)	1981-10-07
IE51319B1 (en)	1986-12-10
NO156752B (no)	1987-08-10
NZ196522A (en)	1985-10-11
FI71737C (fi)	1987-02-09
SU1068037A3 (ru)	1984-01-15

Publication	Publication Date	Title
CS256366B2 (en)	1988-04-15	Method of new 3-(1-piperidinylalkyl)-4h-pyridol(1,2-pyrimidine-4-on derivatives production
EP0110435B1 (fr)	1989-01-04	((Bis(aryl)méthylène)-1-pipéridinyl)alcoyl-pyrimidinones
EP0196132B1 (fr)	1992-08-12	Dérivés de 1,2-benzisoxazol-3-yle et 1,2-benzisothiazol-3-yle
EP0070053B1 (fr)	1986-04-16	Dérivés bicycliques de pyrimidin-5-one
US4581171A (en)	1986-04-08	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders
EP0453042B1 (fr)	1999-11-03	4H-pyrido-(1,2-a)pyrimidin-4-ones substituées sur les positiones 2 et 9
CZ279903B6 (cs)	1995-08-16	Nové substituované thiazolylderiváty a substituované pyridinylderiváty, způsob jejich výroby a antialergické přípravky na jejich bázi
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JPH0215550B2 (fr)	1990-04-12
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