GB1428480A - Heterocyclic spiro compounds and processes for their production - Google Patents
Heterocyclic spiro compounds and processes for their productionInfo
- Publication number
- GB1428480A GB1428480A GB2045473A GB2045473A GB1428480A GB 1428480 A GB1428480 A GB 1428480A GB 2045473 A GB2045473 A GB 2045473A GB 2045473 A GB2045473 A GB 2045473A GB 1428480 A GB1428480 A GB 1428480A
- Authority
- GB
- United Kingdom
- Prior art keywords
- spiro
- bicyclo
- piperidine
- formula
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 Heterocyclic spiro compounds Chemical class 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 15
- 238000006243 chemical reaction Methods 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- VRQDPNKOUPEWOC-UHFFFAOYSA-N spiro[bicyclo[2.2.2]octane-3,3'-piperidine] Chemical compound C1CCNCC21C(CC1)CCC1C2 VRQDPNKOUPEWOC-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract 2
- 150000004678 hydrides Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- ZICFHDLZULVMMB-UHFFFAOYSA-N 3-(2-cyanoethyl)bicyclo[2.2.2]octane-3-carbonitrile Chemical compound C1CC2C(CCC#N)(C#N)CC1CC2 ZICFHDLZULVMMB-UHFFFAOYSA-N 0.000 abstract 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- SXQNXEMGIGVBQJ-UHFFFAOYSA-N 5-(2-cyanoethyl)bicyclo[2.2.2]oct-2-ene-5-carbonitrile Chemical compound C1CC2C(CCC#N)(C#N)CC1C=C2 SXQNXEMGIGVBQJ-UHFFFAOYSA-N 0.000 abstract 1
- UGWKKYZTZPIIEE-UHFFFAOYSA-N 5-(2-ethoxy-2-oxoethyl)bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(CC(=O)OCC)(C(O)=O)CC1C=C2 UGWKKYZTZPIIEE-UHFFFAOYSA-N 0.000 abstract 1
- YZGFGXBZXHCJPU-UHFFFAOYSA-N 5-(carboxymethyl)bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(CC(=O)O)(C(O)=O)CC1C=C2 YZGFGXBZXHCJPU-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 abstract 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003235 pyrrolidines Chemical class 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 150000003413 spiro compounds Chemical class 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH661372A CH582143A5 (OSRAM) | 1972-05-04 | 1972-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428480A true GB1428480A (en) | 1976-03-17 |
Family
ID=4312312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2045473A Expired GB1428480A (en) | 1972-05-04 | 1973-04-30 | Heterocyclic spiro compounds and processes for their production |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3914222A (OSRAM) |
| JP (1) | JPS4961160A (OSRAM) |
| AR (3) | AR203267A1 (OSRAM) |
| AT (1) | AT328446B (OSRAM) |
| AU (1) | AU5510673A (OSRAM) |
| BE (1) | BE799023A (OSRAM) |
| CH (1) | CH582143A5 (OSRAM) |
| DD (1) | DD107032A5 (OSRAM) |
| DE (1) | DE2321057A1 (OSRAM) |
| ES (1) | ES414277A1 (OSRAM) |
| FR (1) | FR2183204B1 (OSRAM) |
| GB (1) | GB1428480A (OSRAM) |
| HU (1) | HU169463B (OSRAM) |
| IE (1) | IE37560B1 (OSRAM) |
| IL (1) | IL42104A (OSRAM) |
| NL (1) | NL7306276A (OSRAM) |
| PL (2) | PL94194B1 (OSRAM) |
| SU (4) | SU506292A3 (OSRAM) |
| ZA (1) | ZA732804B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931805A (en) * | 1958-11-10 | 1960-04-05 | Smith Kline French Lab | Spiro [bicyclo [2. 2. 1] heptane-2, 2'-alkylenimines] |
-
1972
- 1972-05-04 CH CH661372A patent/CH582143A5/xx not_active IP Right Cessation
-
1973
- 1973-04-25 IL IL42104A patent/IL42104A/en unknown
- 1973-04-25 IE IE644/73A patent/IE37560B1/xx unknown
- 1973-04-25 ZA ZA732804A patent/ZA732804B/xx unknown
- 1973-04-26 DE DE2321057A patent/DE2321057A1/de active Pending
- 1973-04-30 GB GB2045473A patent/GB1428480A/en not_active Expired
- 1973-05-02 AU AU55106/73A patent/AU5510673A/en not_active Expired
- 1973-05-02 US US356545A patent/US3914222A/en not_active Expired - Lifetime
- 1973-05-02 JP JP48049647A patent/JPS4961160A/ja active Pending
- 1973-05-02 ES ES414277A patent/ES414277A1/es not_active Expired
- 1973-05-02 DD DD170569A patent/DD107032A5/xx unknown
- 1973-05-03 AT AT390373A patent/AT328446B/de not_active IP Right Cessation
- 1973-05-03 FR FR7315859A patent/FR2183204B1/fr not_active Expired
- 1973-05-03 SU SU1921901A patent/SU506292A3/ru active
- 1973-05-03 BE BE130678A patent/BE799023A/xx unknown
- 1973-05-03 PL PL1973183139A patent/PL94194B1/pl unknown
- 1973-05-03 HU HUCI1369A patent/HU169463B/hu unknown
- 1973-05-03 PL PL1973162293A patent/PL89236B1/pl unknown
- 1973-05-04 AR AR247860A patent/AR203267A1/es active
- 1973-05-04 NL NL7306276A patent/NL7306276A/xx unknown
-
1974
- 1974-01-01 AR AR253541A patent/AR207446A1/es active
- 1974-01-01 AR AR253540A patent/AR207634A1/es active
- 1974-07-12 SU SU2043836A patent/SU508191A3/ru active
- 1974-07-12 SU SU2043773A patent/SU521841A3/ru active
- 1974-07-12 SU SU2043837A patent/SU514568A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU514568A3 (ru) | 1976-05-15 |
| IE37560L (en) | 1973-11-04 |
| HU169463B (OSRAM) | 1976-11-28 |
| JPS4961160A (OSRAM) | 1974-06-13 |
| DD107032A5 (OSRAM) | 1974-07-12 |
| AR203267A1 (es) | 1975-08-29 |
| ZA732804B (en) | 1974-04-24 |
| IL42104A (en) | 1976-12-31 |
| AR207634A1 (es) | 1976-10-22 |
| SU506292A3 (ru) | 1976-03-05 |
| IL42104A0 (en) | 1973-07-30 |
| FR2183204B1 (OSRAM) | 1976-05-14 |
| AU5510673A (en) | 1974-11-07 |
| IE37560B1 (en) | 1977-08-17 |
| AT328446B (de) | 1976-03-25 |
| AR207446A1 (es) | 1976-10-08 |
| SU508191A3 (ru) | 1976-03-25 |
| DE2321057A1 (de) | 1973-11-22 |
| SU521841A3 (ru) | 1976-07-15 |
| BE799023A (fr) | 1973-11-05 |
| US3914222A (en) | 1975-10-21 |
| ES414277A1 (es) | 1976-01-16 |
| ATA390373A (de) | 1975-06-15 |
| NL7306276A (OSRAM) | 1973-11-06 |
| PL89236B1 (OSRAM) | 1976-11-30 |
| PL94194B1 (OSRAM) | 1977-07-30 |
| FR2183204A1 (OSRAM) | 1973-12-14 |
| CH582143A5 (OSRAM) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |