CH616667A5 - - Google Patents

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Info

Publication number: CH616667A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; tolyl; hydrogen; optically active
Prior art date: 1972-12-23

Application number

CH1516877A

Other languages

German (de)

English (en)

Inventor

Ernst-Otto Dr Renth

Anton Dr Mentrup

Kurt Dr Schromm

Peter Dr Danneberg

Original Assignee

Boehringer Sohn Ingelheim

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.)

1972-12-23

Filing date

1977-12-09

Publication date

1980-04-15

1977-12-09 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1978-11-16 Priority to NLAANVRAGE7811322,A priority Critical patent/NL175545C/xx

1978-11-20 Priority to DE2850264A priority patent/DE2850264C2/de

1978-11-20 Priority to AT0824378A priority patent/AT374270B/de

1978-11-21 Priority to ES475272A priority patent/ES475272A1/es

1978-11-30 Priority to SE7812346A priority patent/SE443865B/sv

1978-12-05 Priority to IT30544/78A priority patent/IT1101382B/it

1978-12-06 Priority to GB7847432A priority patent/GB2009919B/en

1978-12-06 Priority to US05/967,026 priority patent/US4265225A/en

1978-12-07 Priority to FR7834469A priority patent/FR2411377A1/fr

1980-04-15 Publication of CH616667A5 publication Critical patent/CH616667A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
150000004885 piperazines Chemical class 0.000 claims 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
-1 2,3-xylyl Chemical group 0.000 description 18
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
238000000576 coating method Methods 0.000 description 3
239000008298 dragée Substances 0.000 description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
239000000243 solution Substances 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000003001 depressive effect Effects 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
XOPUORAQCYGJPT-UHFFFAOYSA-N methanesulfonic acid;hydrochloride Chemical compound Cl.CS(O)(=O)=O XOPUORAQCYGJPT-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
NSFIAKFOCAEBER-QZTJIDSGSA-N (2s,3s)-2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1[C@@](O)(C(O)=O)[C@](O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-QZTJIDSGSA-N 0.000 description 1
WICKLEOONJPMEQ-UHFFFAOYSA-N 1-(2-methylphenyl)piperazine Chemical compound CC1=CC=CC=C1N1CCNCC1 WICKLEOONJPMEQ-UHFFFAOYSA-N 0.000 description 1
RQAVSDINDRNIKL-UHFFFAOYSA-N 1-chloro-3-isocyanatopropane Chemical compound ClCCCN=C=O RQAVSDINDRNIKL-UHFFFAOYSA-N 0.000 description 1
XEMCRISYVYTOOF-UHFFFAOYSA-N 3-[4-[2-[4-(2-chlorophenyl)piperazin-1-yl]ethyl]phenyl]imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1N1CCN(CCC=2C=CC(=CC=2)N2C(NCC2=O)=O)CC1 XEMCRISYVYTOOF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003627 anti-cholesterol Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000572 bronchospasmolytic effect Effects 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
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 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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
- 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Obesity (AREA)
Rheumatology (AREA)
Anesthesiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH1516877A 1972-12-23 1977-12-09 CH616667A5 (es)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
NLAANVRAGE7811322,A NL175545C (nl)	1977-12-09	1978-11-16	Element voor het opnemen van zonne-energie.
DE2850264A DE2850264C2 (de)	1977-12-09	1978-11-20	Sonnenkollektor aus einzelnen Bauteilen als Dacheindeckung
AT0824378A AT374270B (de)	1977-12-09	1978-11-20	Element zur aufnahme von sonnenenergie
ES475272A ES475272A1 (es)	1977-12-09	1978-11-21	Perfeccionamientos en los elementos para la absorcion de energia solar.
SE7812346A SE443865B (sv)	1977-12-09	1978-11-30	Element for upptagning av solenergi
IT30544/78A IT1101382B (it)	1977-12-09	1978-12-05	Elemento per l'assorbimento di energia solare
GB7847432A GB2009919B (en)	1977-12-09	1978-12-06	Solar collector element
US05/967,026 US4265225A (en)	1977-12-09	1978-12-06	Solar collector element
FR7834469A FR2411377A1 (fr)	1977-12-09	1978-12-07	Element de captation d'energie solaire

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2263211A DE2263211A1 (de)	1972-12-23	1972-12-23	Neue arylpiperazine und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CH616667A5 true CH616667A5 (es)	1980-04-15

Family

ID=5865328

Family Applications (10)

Application Number	Title	Priority Date
CH1790773A CH605872A5 (es)	1972-12-23	1973-12-20
CH1517077A CH616669A5 (es)	1972-12-23	1977-12-09
CH1517477A CH616676A5 (es)	1972-12-23	1977-12-09
CH1516977A CH616668A5 (es)	1972-12-23	1977-12-09
CH1517577A CH616677A5 (es)	1972-12-23	1977-12-09
CH1516877A CH616667A5 (es)	1972-12-23	1977-12-09
CH1517277A CH616674A5 (es)	1972-12-23	1977-12-09
CH1516777A CH616673A5 (es)	1972-12-23	1977-12-09
CH1517177A CH616670A5 (es)	1972-12-23	1977-12-09
CH1517377A CH616675A5 (es)	1972-12-23	1977-12-09

Family Applications Before (5)

Application Number	Title	Priority Date
CH1790773A CH605872A5 (es)	1972-12-23	1973-12-20
CH1517077A CH616669A5 (es)	1972-12-23	1977-12-09
CH1517477A CH616676A5 (es)	1972-12-23	1977-12-09
CH1516977A CH616668A5 (es)	1972-12-23	1977-12-09
CH1517577A CH616677A5 (es)	1972-12-23	1977-12-09

Family Applications After (4)

Application Number	Title	Priority Date
CH1517277A CH616674A5 (es)	1972-12-23	1977-12-09
CH1516777A CH616673A5 (es)	1972-12-23	1977-12-09
CH1517177A CH616670A5 (es)	1972-12-23	1977-12-09
CH1517377A CH616675A5 (es)	1972-12-23	1977-12-09

Country Status (15)

Country	Link
US (1)	US3941789A (es)
JP (4)	JPS4994688A (es)
AT (1)	AT338271B (es)
BE (1)	BE809041A (es)
CH (10)	CH605872A5 (es)
DE (1)	DE2263211A1 (es)
ES (10)	ES421751A1 (es)
FI (1)	FI59990C (es)
FR (1)	FR2211252B1 (es)
GB (1)	GB1456253A (es)
IE (1)	IE38679B1 (es)
LU (1)	LU69064A1 (es)
NL (1)	NL7317469A (es)
NO (1)	NO140381C (es)
SE (1)	SE417516B (es)

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DE2834114A1 (de) *	1978-08-01	1980-02-14	Schering Ag	Polyalkoxyphenylpyrrolidone iii, verfahren zu ihrer herstellung und ihre verwendung
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GB8603120D0 (en) *	1986-02-07	1986-03-12	Pfizer Ltd	Anti-dysrhythmia agents
US4732895A (en) *	1986-05-02	1988-03-22	American Cyanamid Company	α-[5-methyl-2-(pyridinyl)-1H-imidazol-4-yl]substituted-1-piperazineethanols useful for treating hypertension
JPH0788357B2 (ja) *	1986-10-27	1995-09-27	吉富製薬株式会社	ピペラジン化合物
DE3803860A1 (de) *	1988-02-09	1989-08-17	Basf Ag	N,n'-disubstituierte piperazine
US5382583A (en) *	1989-04-22	1995-01-17	John Wyeth & Brother, Limited	Piperazine derivatives
US5364849A (en) *	1989-04-22	1994-11-15	John Wyeth & Brother, Limited	1-[3 or 4-[1-[4-piperazinyl]]-2 arylpropionyl or butryl]-heterocyclic derivatives
US5166148A (en) *	1990-07-09	1992-11-24	The Du Pont Merck Pharmaceutical Company	2-amino-1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity
SK283420B6 (sk) *	1992-05-08	2003-07-01	Pharmacia & Upjohn Company	Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny
DK148392D0 (da) *	1992-12-09	1992-12-09	Lundbeck & Co As H	Heterocykliske forbindelser
WO1994018172A1 (en) *	1993-02-01	1994-08-18	Yoshitomi Pharmaceutical Industries, Ltd.	Imidazolylbenzene compound and use thereof as medicine
IL114027A (en) *	1994-06-08	1999-11-30	Lundbeck & Co As H	4-Phenyl piperazine (piperidine or tetrahydropyridine) derivatives serotinin 5-HT1A and dopamin D2 receptor ligand pharmaceutical compositions containing them
WO1996014297A1 (fr) *	1994-11-04	1996-05-17	Sumitomo Pharmaceuticals Company, Limited	Nouveaux derives de lactame
CA2250347C (en) *	1996-03-29	2006-02-21	Duphar International Research B.V.	Piperazine and piperidine compounds with high affinity for dopamine-d2 and serotonin-5ht1a receptors
JP4349320B2 (ja)	2005-05-12	2009-10-21	パナソニック株式会社	マニピュレータ型ロボット
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CN114634479B (zh) *	2020-12-16	2025-02-07	北京盈科瑞创新药物研究有限公司	一种派嗪衍生物、其制备方法及应用

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BE788280A (fr) *	1971-09-04	1973-02-28	Pfizer	Nouvelles 1-(3-trifluoro-methyl-phenyl)-4-((amido cyclique)- alkyl) piperazines et composition pharmaceutique les contenant

1972
- 1972-12-23 DE DE2263211A patent/DE2263211A1/de not_active Withdrawn
1973
- 1973-12-20 NL NL7317469A patent/NL7317469A/xx not_active Application Discontinuation
- 1973-12-20 CH CH1790773A patent/CH605872A5/xx not_active IP Right Cessation
- 1973-12-20 FI FI3940/73A patent/FI59990C/fi active
- 1973-12-20 GB GB5919473A patent/GB1456253A/en not_active Expired
- 1973-12-21 BE BE139227A patent/BE809041A/xx not_active IP Right Cessation
- 1973-12-21 LU LU69064A patent/LU69064A1/xx unknown
- 1973-12-21 AT AT1072773A patent/AT338271B/de not_active IP Right Cessation
- 1973-12-21 NO NO4936/73A patent/NO140381C/no unknown
- 1973-12-21 JP JP49004699A patent/JPS4994688A/ja active Pending
- 1973-12-21 FR FR7346112A patent/FR2211252B1/fr not_active Expired
- 1973-12-21 SE SE7317423A patent/SE417516B/xx unknown
- 1973-12-21 US US05/427,367 patent/US3941789A/en not_active Expired - Lifetime
- 1973-12-22 ES ES421751A patent/ES421751A1/es not_active Expired
- 1973-12-28 IE IE2338/73A patent/IE38679B1/xx unknown
1976
- 1976-01-29 ES ES444730A patent/ES444730A1/es not_active Expired
- 1976-01-29 ES ES444735A patent/ES444735A1/es not_active Expired
- 1976-01-29 ES ES444737A patent/ES444737A1/es not_active Expired
- 1976-01-29 ES ES444731A patent/ES444731A1/es not_active Expired
- 1976-01-29 ES ES444734A patent/ES444734A1/es not_active Expired
- 1976-01-29 ES ES444733A patent/ES444733A1/es not_active Expired
- 1976-01-29 ES ES444738A patent/ES444738A1/es not_active Expired
- 1976-01-29 ES ES444736A patent/ES444736A1/es not_active Expired
- 1976-01-29 ES ES444732A patent/ES444732A1/es not_active Expired
1977
- 1977-12-09 CH CH1517077A patent/CH616669A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1517477A patent/CH616676A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1516977A patent/CH616668A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1517577A patent/CH616677A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1516877A patent/CH616667A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1517277A patent/CH616674A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1516777A patent/CH616673A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1517177A patent/CH616670A5/de not_active IP Right Cessation
- 1977-12-09 CH CH1517377A patent/CH616675A5/de not_active IP Right Cessation
1983
- 1983-07-15 JP JP58129263A patent/JPS5976074A/ja active Pending
- 1983-07-15 JP JP58129261A patent/JPS5976070A/ja active Pending
- 1983-07-15 JP JP58129262A patent/JPS5976067A/ja active Pending

Also Published As

Publication number	Publication date
AT338271B (de)	1977-08-10
GB1456253A (en)	1976-11-24
CH616677A5 (es)	1980-04-15
FR2211252B1 (es)	1977-01-28
JPS4994688A (es)	1974-09-09
BE809041A (fr)	1974-06-21
NL7317469A (es)	1974-06-25
CH616673A5 (es)	1980-04-15
FR2211252A1 (es)	1974-07-19
ES444736A1 (es)	1977-05-16
NO140381C (no)	1979-08-22
ES421751A1 (es)	1976-12-16
JPS5976070A (ja)	1984-04-28
CH605872A5 (es)	1978-10-13
CH616669A5 (es)	1980-04-15
ES444738A1 (es)	1977-05-16
CH616675A5 (es)	1980-04-15
JPS5976074A (ja)	1984-04-28
ES444737A1 (es)	1977-05-16
NO140381B (no)	1979-05-14
AU6397773A (en)	1975-07-03
IE38679L (en)	1974-06-23
US3941789A (en)	1976-03-02
ATA1072773A (de)	1976-12-15
DE2263211A1 (de)	1974-07-04
CH616670A5 (es)	1980-04-15
ES444734A1 (es)	1977-05-16
SE417516B (sv)	1981-03-23
IE38679B1 (en)	1978-05-10
FI59990B (fi)	1981-07-31
LU69064A1 (es)	1975-08-20
CH616668A5 (es)	1980-04-15
CH616674A5 (es)	1980-04-15
ES444733A1 (es)	1977-05-16
ES444731A1 (es)	1977-05-16
ES444730A1 (es)	1977-05-16
ES444735A1 (es)	1977-05-16
FI59990C (fi)	1981-11-10
ES444732A1 (es)	1977-05-16
JPS5976067A (ja)	1984-04-28
CH616676A5 (es)	1980-04-15

Publication	Publication Date	Title
CH616667A5 (es)	1980-04-15
DE69613240T2 (de)	2002-04-25	N-aminoalkylfluorencarboxamide, neue klasse von dopaminerezeptor subtype spezifische liganden
CH626057A5 (es)	1981-10-30
DD203045A5 (de)	1983-10-12	Verfahren zur herstellung von cis-4-phenyl-1,2,3,4-tetra-hydro-1-napthalinamin-derivaten
DE3888778T2 (de)	1994-07-14	Polyamin-Derivate als antineoplastische Wirkstoffe.
CH616146A5 (es)	1980-03-14
DE2408476C2 (es)	1990-12-06
EP0271013B1 (de)	1993-06-09	Basisch substituierte Phenylacetonitrile, ihre Herstellung und diese enthaltende Arzneimittel
DE69817557T2 (de)	2004-06-17	Piperidine derivate als inhibitoren der neurotransmitter-wiederaufbaunahme
DE3900028A1 (de)	1989-07-13	Gegebenenfalls am phenylrest halogen- und/oder alkyl- und/oder alkoxy- oder methylendioxysubstituierte, 5,5-di-(methyl)-3-(phenylvinyl)-1-(substituiert amino-alkoxy-imino)-cyclohex-2-enderivate, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
DE2708110A1 (de)	1977-09-08	Pyrrolbenzoxaaza-alkane
DE1670622A1 (de)	1971-02-25	Verfahren zur Herstellung von Aminoalkyl-pyrrol-2-yl-ketonen
DE69024385T2 (de)	1996-05-30	Verbindung zur Behandlung von Störungen des Neurotransmittersystems im Gehirn
AT338802B (de)	1977-09-12	Verfahren zur herstellung von neuen piperazinderivaten und ihren salzen
AT338807B (de)	1977-09-12	Verfahren zur herstellung von neuen piperazinderivaten und ihren salzen
CH615177A5 (en)	1980-01-15	Process for the preparation of novel substituted N-[1-(3,4-methylenedioxyphenyl)-propyl-(2)]-N'-phenylpiperazines
CH615174A5 (en)	1980-01-15	Process for the preparation of novel substituted N-[1-(3,4-methylenedioxyphenyl)-propyl-(2)]-N'-phenylpiperazines
EP1497256B1 (de)	2010-06-09	Substituierte 1,5-diaminopentan-3-ol-verbindungen
DE69211773T2 (de)	1997-02-13	Amidderivate von 1-Amino-Octahydropyrido[2,1-c][1,4]oxazin, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2421549A1 (de)	1974-11-21	Naphthalinderivate, verfahren zu ihrer herstellung und arzneimittel
AT338806B (de)	1977-09-12	Verfahren zur herstellung von neuen piperazinderivaten und ihren salzen
AT338803B (de)	1977-09-12	Verfahren zur herstellung von neuen piperazinderivaten und ihren salzen
DE2951235A1 (de)	1980-11-06	Cyclododecanderivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel
AT344708B (de)	1978-08-10	Verfahren zur herstellung neuer substituierter n- (1-(3,4-methylendioxyphenyl)-propyl(2))-n'-substituierter phenylpiperazine und deren salzen und optisch aktiven formen
DE2934450C2 (de)	1984-09-06	N-(Trimethoxybenzyl)-piperazinderivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel

Legal Events

Date	Code	Title	Description
1984-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased